Title of Invention	ANTIVIRAL PYRIMIDINEDIONE DERIVATIVES AND BPROCESS FOR THE PREPARATION THEREOF
Abstract	The present invention relates to pyrimidinedione derivatives of the following formula (I) which are useful as antiviral agents, especially as agents for treatment of AIDS, pharmaceutically acceptable salts thereof, process for the preparation thereof and pharmaceutical compositions containing the same. wherein R represents cyclopropyl; cyclobutyl; cyclohexyl; unsubstituted or mono-, di- or tri-substituted phenyl with a group selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, halogen, trifluoromethyl, cyano and amino; 1- or 2-naphthyl; 9-anthracenyl; 2-anthraquinonyl; unsubstituted or substituted pyridyl with a group selected from C1-C4 alkyl, C1-C4 alkoxy, cyano and halogen; 2~, 3- or 4-quinolinyl; oxiranyl; 1-benzotriazolyl; 2-benzoxazolyl; furanyl substituted with C1-C4 alkoxycarbonyl; C1-C4 alkylcarbonyl; or benzoyl, R1 represents halogen or C1-C4 alkyl, R2 and R3 represent independently hydrogen or C1-C4alkyl, X represents oxygen atom, and Y represents oxygen atom, sulfur atom or carbonyl.

Title of Invention

ANTIVIRAL PYRIMIDINEDIONE DERIVATIVES AND BPROCESS FOR THE PREPARATION THEREOF

Abstract

The present invention relates to pyrimidinedione derivatives of the following formula (I) which are useful as antiviral agents, especially as agents for treatment of AIDS, pharmaceutically acceptable salts thereof, process for the preparation thereof and pharmaceutical compositions containing the same. wherein R represents cyclopropyl; cyclobutyl; cyclohexyl; unsubstituted or mono-, di- or tri-substituted phenyl with a group selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, halogen, trifluoromethyl, cyano and amino; 1- or 2-naphthyl; 9-anthracenyl; 2-anthraquinonyl; unsubstituted or substituted pyridyl with a group selected from C1-C4 alkyl, C1-C4 alkoxy, cyano and halogen; 2~, 3- or 4-quinolinyl; oxiranyl; 1-benzotriazolyl; 2-benzoxazolyl; furanyl substituted with C1-C4 alkoxycarbonyl; C1-C4 alkylcarbonyl; or benzoyl, R1 represents halogen or C1-C4 alkyl, R2 and R3 represent independently hydrogen or C1-C4alkyl, X represents oxygen atom, and Y represents oxygen atom, sulfur atom or carbonyl.

Full Text	Field of the invention The present invention relates to novel pyrimidinedione derivatives or pharmaceutically acceptable salts thereof which are useful as antiviral agents, especially for treatment of AIDS, and process for the preparation thereof. Description of the prior art Nowadays, there are about 15 chemotherapeutic agents for AIDS which were approved by the FDA. It has been known that such chemotherapeutic agents have medical action mechanisms to inhibit replication of AIDS virus. However, they also have drug tolerance and undesirable side effects due to their toxicity. In order to solve these problems, many researches have been carried out to develope new antiviral chemotherapeutic agents with strong antiviral activity as well as lower toxicity. Much researches to develop new antiviral agents for treatment of AIDS have been focused on pyrimidinedione derivatives, and thus the present inventors have synthesized various new pyrimidinedione derivatives by introducing homocarbocyclic groups to the N-1 position of pyrimidinedione derivatives, which compounds were applied for patent (see, WO97/30979, US patent 5,922,727), and they continued synthesis and evaluation of new derivatives prepared by introducing new homocarbocyclic groups, aryl and heteroaryl substituents, alkyl and aryl carbonylmethyl groups to the pyrimidinedione derivatives and studied their pharmacological effects. As the result, the inventors have found that the newly synthesized derivatives by the present invention have unexpectedly strong anti-HIV (Human Immunodeficiency Virus) activity as well as very low toxicity. Summary of the invention Accordingly, an object of the present invention is to provide new pyrimidinedione derivatives of the following formula (I) or pharmaceutically acceptable salts thereof which have strong antiviral activity against HIV. (Formula Removed) wherein R represents cyclopropyl; cyclobutyl; cyclohexyl; unsubstituted or mono-, di- or tri-substituted phenyl with a group selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, halogen, trifluoromethyl, cyano and amino; 1- or 2-naphthyl; 9-anthracenyl; 2-anthraquinonyl; unsubstituted or substituted pyridyl with a group selected from C1-C4 alkyl, C1-C4 alkoxy, cyano and halogen; 2-, 3- or 4-quinolinyl; oxiranyl; 1-benzotriazolyl; 2-benzoxazolyl; furanyl substituted with C1-C4 alkoxycarbonyl; C1-C4 alkylcarbonyl; or benzoyl, R1 represents halogen or C1-C4 alkyl, R2 and R3 represent independently hydrogen orC1-C4 alkyl, X represents oxygen atom, and Y represents oxygen atom, sulfur atom or carbonyl. Another object of the invention is to provide a process for the preparation of the compounds of the general formula (I) or pharmaceutically acceptable salts thereof. The other object of the invention is to provide pharmaceutical preparations having antiviral activity which contains the compound of the general formula (I) or a pharmaceutically acceptable salt thereof as the active ingredient. Detailed description of the invention The compounds of the general formula (I) according to the present invention may be prepared by the following reaction scheme 1. Scheme 1 (Scheme Removed) wherein R, R1, R2, R3, X and Y are as defined above, and Lie represents a conventional leaving group such as halogen, alkylsulfonyl and arylsulfonyl. The compounds of the general formula (I) may be prepared by reacting a compound of the general formula (II) with a compound of the general formula (III) in a conventional organic solvent and in the presence of a base. The base used in the above reaction may include anhydrous sodium bicarbonate, anhydrous sodium carbonate, sodium hydride and anhydrous potassium carbonate. The organic solvent used in the reaction may include an organic polar solvent such as dimethylformamide, acetonitrile and dimethylsulfoxide. In addition, a catalyst such as potassium iodide, lithium iodide or the like may be used. The reaction may be carried out preferably at the temperature of 10 — 100°C for 1-48 hours. 6-substituted pyrimidinedione derivatives of the formula (II) used in the present invention may be prepared as described in WO 93/02044 and WO 95/18109, or by using a similar method thereto. The compounds of the formula (I) may form an addition salt with a pharmaceutically acceptable inorganic or organic acid or base; for example, bases such as salts of alkali metal and alkaline earth metal including sodium, potassium, magnesium and calcium; inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid and nitric acid; organic acids such as formic acid, acetic acid, propionic acid, succinic acid, citric acid, maleic acid, glycolic aicd, lactic acid and malonic acid; amino acids such as serine, cysteine, cystine, asparagine, glutamine, lysine, arginine, leucine and proline; sulfonic acids such as methane sulfonate, ethane sulfonate, benzene sulfonate and toluene sulfonate. The compounds of the general formula (I) or pharmaceutically acceptable salts thereof may be formulated into conventional pharmaceutical preparations in combination with pharmaceutically acceptable vehicles or carriers, whereby the preparations may be used for treatment or prevention of various viral diseases. Examples The compounds of the general formula (I) defined in the following table were prepared in the following examples. (Table Removed) Example 1: l-(Cyclopropyl)methyl-5-ethyl-6-(3,5-dimethylphenyl)- thio-2,4-pyrimidinedione To a solution of 5-ethyl-6-(3,5~dimethylphenyl)thio-2,4-pyrimidinedione ( 276mg, l.Ommol ) and bromomethyl cyclopropane ( 160mg, l.Ommol, 85% ) dissolved in dimethylformamide ( 5ml ), sodium bicarbonate ( 126mg, 1.50mmol ) and lithium iodide ( 13.0mg, 0.l0mmol ) were added. The resulting mixture was stirred at 90°C for 24 hrs, distilled under the reduced pressure to remove dimethylformamide and purified with column chromatography to obtain the titled compound as a white solid ( 152 mg, yield : 46.0%). Example 2'- l-(Cyclopropyl)methyl-5-isopropyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and bromomethyl cyclopropane were reacted by the same way with the example 1 to obtain the titled compound ( 170mg, yield : 49.4%). Example 3: l-(Cyclopropyl)methyl-5-ethyl-6-(3,5-dimethylphenoxy)"2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and bromomethyl cyclopropane were reacted by the same way with the example 1 to obtain the titled compound ( 146mg, yield : 46.4%). Example 4: 1 - (Cyclopropyl)methyl-5-isopropyl-6- (3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5~dimethylphenoxy )-2,4-pyrimidinedione and bromomethyl cyclopropane were reacted by the same way with the example 1 to obtain the titled compound ( 132mg, yield : 40.2%). Example 5: l-(Cyclopropyl)methyl-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and bromomethyl cyclopropane were reacted by the same way with the example 1 tc obtain the titled compound ( 165mg, yield : 50.6%). Example 6: l-(Cyclopropyl)methyl-5-isopropyl-6-(3,5-dimethylbenzoyI)-2,4 - py rimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and bromomethyl cyclopropane were reacted by the same way with the example 1 to obtain the titled compound ( 158mg, yield : 46.4%). Example 7: l-(Cyclobutyl)methyl-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and (cyclobutyl) methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 150mg, yield : 43.5%). Example 8: l-(Cyclobutyl)methyl-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5~Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and (cyclobutyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 147mg, yield : 41.0%). Example 9: l-(Cyclobutyl)methyl-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and (cyclobutyl)-methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 192mg, yield : 58.5%). Example 10: 1 - (Cyclobutyl)methyl-5-isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and (cyclobutyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 164mg, yield : 47.9%). Example 11: l-(Cyclobutyl)methyl-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ehtyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and (cyclobutyl)-methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 179mg, yield : 52.6%). Example 12: l-(Cyclobutyl)methyl-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and (cyclobutyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 182mg, yield : 51.3%). Example 13: l-(Cyclohexyl)methyl-5-ethyl-6-(3,5-dimethylphenyl)thio- 2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and (cyclohexyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 195mg, yield •' 52.3%). Example 14: l-(Cyclohexyl)methyl-5-isopropyl-6-(3,5-dimethylphenyl)- thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and (cyclohexyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 210mg, yield •' 54.3%). Example 15: l-(Cydohexyl)methyl-5-ethyl-6-(3,5~dimethylphenoxy)-2,4- pyrimidinedione 5-Ethyl-6~(3,5-dimethylphenoxy)-2,4-pyrimidinedione and (cyclohexyl) -methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 185mg, yield : 51.9%). Example 16: 1 - (Cyclohexyl)methyl-5-isopropyl -6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione 5-Isopropyl -6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and (cyclohexyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 201mg, yield : 54.3%). Example 17: l-(Cyclohexyl)methyl-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and (cyclohexyl)- methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 233mg, yield : 63.2%). Example 18: l-(Cyclohexyl)methyl-5-isopropyl-6-(3,5-dimethylbenzoyl)- 2,4- pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and (cyclohexyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 212mg, yield : 55.4%). Example 19: l-Benzyl-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidine dione 5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 275mg, yield : 75.0%). Example 20: l-Benzyl-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4- pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 300mg, yield : 79.0%). Example 21: l-Benzyl-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidine-dione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 285mg, yield : 72.5%). Example 22: l-Benzyl-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4- pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4_pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 264mg, yield : 72.5%). Example 23: l-Benzyl-5-ethyl-6- (3,5-dimethylbenzoyl)-2,4-pyrimidine-dione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 289mg, yield : 79.8%). Example 24: l-Benzyl-5-isopropyl-6-(3,5-dimethylbenzoyl)~2,4- pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)~2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 293mg, yield : 78.0%). Example 25: l-(3-Methoxybenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3-methoxylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 175mg, yield : 44.1%). Example 26: l-(3-Methoxybenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3-methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 203mg, yield : 49.4%). Example 27: l-(3-Methoxybenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3-methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 213mg, yield : 56.0%) Example 28: 1 -(3-Methoxybenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4"Pyrimidinedione and 3-methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 217mg, yield : 55.0%). Example 29: l-(3-Methoxybenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)~2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 3-methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 252mg, yield : 64.2%). Example 30: l-(3-Methoxybenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3-methpoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 235mg, yield : 57.8%). Example 31: l-(4-Trifluoromethoxybenzyl)-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4~pyrimidinedione and 4-trifluoro- methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 195mg, yield : 43.3%). Example 32: l-(4-Trifluoromethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-pheny 1) thio - 2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 208mg, yield : 44.8%). Example 33: l-(4-Trifluoromethoxybenzyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione 5~Ethyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and 4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 233mg, yield : 53.6%). Example 34: l-(4-Trifluoromethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy)~2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and 4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 212mg, yield : 47.3%). Example 35: l-(4-Trifluoromethoxybenzyl)-5-ethyl-6-(3,5-dimethyl-benzoyl) - 2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 285mg, yield : 63.8%). Example 36: l-(4-Trifluoromethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 304mg, yield : 66.0%). Example 37: l-(2-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio~2,4-pyrimidinedione and 2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 162mg, yield : 41.3%). Example 38: l-(2-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)- thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 188mg, yield : 46.4%). Example 39: l-(2-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 201mg, yield : 53.5%). Example 40: l-(2-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 154mg, yield : 39.5%). Example 41". l-(2-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 199mg, yield : 51.4%). Example 42: l-(2-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 231mg, yield : 57.5%). Example 43: l-(3-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 185mg, yield : 47.3%) Example 44: l-(3-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 176mg, yield : 43.4%). Example 45: l-(3-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 216mg, yield : 57.5%). Example 46: l-(3-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4~ pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 193mg, yield : 49.6%). Example 47: 1- (3-Cyanobenzyl)-5-ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione 5~Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 207mg, yield : 53.4%). Example 48: l-(3-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 222mg, yield : 55.3%). Example 49: l-(3,5-Dimethylbenzyl)-5-ethyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 265mg, yield : 67.2%). Example 50: l-(3,5-Dimethylbenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethy lphenyl)thio-2,4-pyrimidinedione and 3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (230mg, yield : 56.3%). Example 51: l-(3,5-Dimethylbenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5~climethylphenoxy)-2,4-pyrimidinedione and 3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (217mg, yield : 57.3%). Example 52: l-(3,5-Dimethylbenzyl)-5-isopropyl-6-(3,5-dimethyl- phenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (260mg, yield : 66.2%). Example 53: l-(3,5-Dimethylbenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (288mg, yield : 73.8%). Example 54: 1- (3,5-Dimethylbenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (322mg, yield : 79.5%). Example 55: l-(3,5-Dimethoxybenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (252mg, yield : 59.1%). Example 56: l-(3,5-Dimethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (234mg, yield '• 53.1%). Example 57: l-(3,5-Dimethoxybenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (279mg, yield : 68.0%). Example 58: l-(3,5-Dimethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy) -2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (275mg, yield : 64.8%). Example 59: l-(3,5-Dimethoxybenzyl)-5-ethyl-6-(3,5-dimethyl- benzoyl)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (212mg, yield : 50.2%). Example 60: l-(3,5-Dimethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (296mg, yield : 67.8%). Example 61: l-[3,5-Bis(trifluoromethyl)benzyl]-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (226mg, yield : 45.0%). Example 62: l-[3,5-Bis(trifluoromethyl)benzyl]-5-isopropyl-6-(3,5- dimethylphenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (195mg, yield : 37.8%). Example 63: l-[3,5-Bis(Trifluoromethyl)benzyl]-5-ethyl-6-(3,5-dimethyl-phenoxy) - 2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (240mg, yield : 49.4%). Example 64: l-[3,5-Bis(Trifluoromethyl)benzyl]-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (266mg, yield : 53.2%) Example 65: l-[3,5-Bis(Trifluoromethyl)benzyl]-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Ethyl~6- (3,5-dimethylbenzoyl) - 2,4-pyrimidinedione and 3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (280mg, yield : 56.2%). Example 66: l-[3,5-Bis(Trifluoromethyl)benzyl]-5-isopropyl~6- (3,5-dimethylbenzoyl ) -2,4- pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (255mg, yield '• 49.8%) Example 67: l-(2,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5~Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (170mg, yield : 42.2%). Example 68: l-(2,5-Difluorobenzyl)-5-isopropyl~6-(3,5~dimethylphenyl)-thio-2,4-pyrimidinedione 5-Isopropy 1 -6 - (3,5-dimethy lpheny 1) thio - 2,4 - pyrimidinedione and 2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (205mg, yield : 49.2%). Example 69: l-(2,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy )-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (185mg, yield : 47.9%). Example 70: l-(2,5-Difluorobenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl~6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and 2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (165mg, yield : 41.2%). Example 71: 1 - (2,5-Difluorobenzyl)-5-ethyl-6- (3,5-dimethylbenzoyl) -2,4- pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (214mg, yield '■ 53.7%). Example 72: 1 -(2,5-Difluorobenzyl)-5-isopropyl-6- (3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimetriylbenzoyl)-2,4-pyrimidinedione and 2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (200mg, yield : 48.5%). Example 73: l-(3,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (196mg, yield : 48.7%). Example 74: 1 - (3,5-Difluorobenzyl) -5~isopropyl-6- (3,5-dimethylphenyl) -thio-2,4-pyrimidinedione 5-Isopropyl~6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (205mg, yield : 49.2%). Example 75: l-(3,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (195mg, yield : 50.5%). Example 76: l-(3,5-Difluorobenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (180mg, yield : 45.0%). Example 77: l-(3,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (236mg, yield : 59.2%). Example 78: l-(3,5-Difluorobenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (220mg, yield : 53.3%). Example 79: 1- (3,5-Dichlorobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (292mg, yield "• 67.1%). Example 80: 1 - (3,5-Dichlorobenzyl)-5-isopropyl-6- (3,5-dimethylphenyl) -thio-2,4-pyrimidinedione 5-isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (250mg, yield : 55.6%). Example 81: 1 - (3,5-Dichlorobenzyl)-5-ethyl-6- (3,5-dimethylphenoxy)-2,4-pyrimidinedione 5~Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (220mg, yield •' 52.7%). Example 82'- l-(3,5-Dichlorobenzyl)-5-isopropyl-6-(3,5-dimethyl- phenoxy)-2,4-pyrimidinedione 5-isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (235mg, yield : 54.2%). Example 83: l-(3,5~Dichlorobenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzol)-2,4-pyrimidinedione and 3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (287mg, yield : 66.5%). Example 84: 1- (3,5-Dichlorobenzyl) ~5-isopropyl-6~ (3,5-dimethylbenzoyl) -2,4-pyrimidinedione 5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (283mg, yield : 63.6%). Example 85: l-(3,5-Dibromobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl~6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (356mg, yield : 67.9%). Example 86: l-(3,5-Dibromobenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (380mg, yield : 70.6%). Example 87: l-(3,5-Dibromobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl~6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (375mg, yield : 73.9%). Example 88: l-(3,5-Dibromobenzyl)-5-isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and 3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (395mg, yield : 75.6%). Example 89: l-(3,5-Dibromobenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (387mg, yield : 74.4%). Example 90: 1- (3,5-Dibromobenzyl) -5-isopropyl~6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione ana 3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (402mg, yield : 75.2%). Example 91: l-(2-Naphthalenemethyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (265mg, yield : 63.6%). Example 92: l-(2-Naphthalenemethyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (298mg, yield : 69.2%). Example 93: l- (2-Naphthalenemethyl)-5-ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (272mg, yield : 67.9%). Example 94: l-(2-Naphthalenemethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy) -2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (274mg, yield : 66.1%). Example 95: l-(2-Naphthalenemethyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (251mg, yield : 60.9%). Example 96: l-(2-Naphthalenemethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (274mg, yield : 64.2%). Example 97: l-(Anthracen-9-ylmethyl)-5-ethyl-6-(3,5-dimethylphenyl)- thio-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound (195mg, yield : 41.8%). Example 98: l-(Anthracen-9-ylmethyl)-5-isopropyl-6-(3,5-dimethyl~ phenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound (215mg, yield : 44.7%). Example 99: l-(Anthracen-9-ylmethyl)-5-ethyl-6-(3,5-dimethyl- phenoxy) -2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound (187mg, yield : 41.5%). Example 100: l-(Anthracen-9-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy) - 2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound (205mg, yield : 44.1%). Example 101 : l-(Anthracen-9-ylmethyl)-5-ethyl-6-(3,5-dimethyl- benzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound ( 216mg, yield : 46.7%). Example 102 : l-(Anthracen-9-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl) -2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound ( 192mg, yield '■ 40.3%). Example 103 : l-(Anthraquinon-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 175mg, yield : 35.1%). Example 104 : l-(Anthraquinon-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl- pheny 1) thio - 2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 165mg, yield : 32.2%). Example 105 : l-(Anthraquinon-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 175mg, yield : 36.3%). Example 106 : l-(Anthraquinon-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 155mg, yield : 31.2%). Example 107 : l-(Anthraquinon-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 178mg, yield : 36.0%). Example 108 : l-(Anthraquinon-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 193mg, yield : 38.0%). Example 109 : l-(Pyridin-2-ylmethyl)-5-ethyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 98mg, yield : 26.7%). Example 110 : l-(Pyridin-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 112mg, yield : 29.4%). Example 111 : l-(Pyridin-2-ylmethyl)-5-ethyl-6-(3,5-dimethylphenoxy)- 2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 125mg, yield : 35.6%). Example 112 : l-(Pyridin-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 136mg, yield : 37.2%). Example 113 : l-(Pyridin-2-ylmethyl)-5-ethyl-6~(3,5-dimethyl-benzoyl) -2,4-pyrimidinedione 5-Ethyl~6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 145mg, yield •' 39.9%). Example 114 : l-(Pyridm-2-2ylmethyl)-5-isopropyl-6-(3,5-dirnethyl-benzoyl) -2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 135mg, yield : 35.8%). Example 115 : l-(Pyridm-3-ylmethyl)-5-etiiyl-6-(3,5-dimethyl-phenyl) thio - 2,4 - py rimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 95mg, yield : 25.9%). Example 116 •' l-(Pyridin-3-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Isopropyl~6- (3,5-dimethylphenyl)thio-2,4~pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 88mg, yield : 23.1%). Example 117 : l-(Pyridin-3-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)~2,4-pyrimidinedione 5-ethyl-6-(3,5-dimethylphenoxy)-2,4~pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( lOlmg, yield : 28.7%). Example 118 : l-(Pyridin-3-ylmethyl)-5-isopropyl-6-(3,5-dimethyl~ phenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 122mg, yield : 33.4%). Example 119 : l~(Pyridin-3-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 120mg, yield '• 33.0%). Example 120 : l-(Pyridin-3-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl) -2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 152mg, yield '• 40.3%). Example 121 "• l-(2-Chloropyridin-6-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 122mg, yield : 30.4%). Example 122 : l-(2-Chloropyridin-6-ylmethyl)-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 130mg, yield : 31.3%). Example 123 : l-(2-Chloropyridin-6-ylmethyl)-5-ethyl-6-(3,5- dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione ana 2-chloro-6~picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 126mg, yield : 32.7%). Example 124 : l-(2-Chloropyridin-6-ylmethyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 135mg, yield : 33.8%). Example 125 : l-(2-Chloropyridin-6-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl) -2,4-pyrimidinedione 5-Ethyl-6- (3,5-climethylbenzoyl) -2,4-pyrimidinedione and 2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 145mg, yield : 36.4%). Example 126 : l-(2-Chloropyridin-6-ylmethyl)-5-isopropyl-6-(3,5~ dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 155mg, yield : 37.6%). Example 127 : l-(2-Bromopyridin-6-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 2-bromo-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 143mg, yield : 33.2%). Example 128 : l-(2-Bromopyridin-6-ylmethyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-bromo-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 167mg, yield : 37.6%). Example 129 : l-(2-Bromopyridib-6-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2-bromo-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 149mg, yield : 35.3%). Example 130 : l-(2-Bromopyridin-6-ylmethyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-bromo-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 148mg, yield : 32.4%). Example 131 : l-(Quinolin-2-ylmethyl)-5~ethyl-6-(3,5-dimemylphenyl)-thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 138mg, yield : 33.1%). Example 132 : l-(Quinolin-2-ylmemyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound { 125mg, yield : 29.0%). Example 133 : l-(Quinolin-2~ylmethyl)-5-ethyl-6-{3,5-dimethyl-phenoxy)-2,4-pyrimidinedione 5-Ethyl-6~ (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 130mg, yield : 32.4%). Example 134 : l-(Quinolin-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 139mg, yield •' 33.5%). Example 135 : l-(Quinolin-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4~pyrimidinedione and 2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 159mg, yield : 38.5%). Example 136 : l-(Qumolin-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoy 1) - 2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 170mg, yield : 39.8%). Example 137 '■ l-(2,3~Epoxypropyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4- pyrimidinedione 1) l-Allyl-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione To a solution of 5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione (258mg, l.Ommol) and allyl bromide(121mg, l.Ommol) dissolved in dimethylformamide(5ml), sodium bicarbonate (126mg, 1.50mmol) and lithium iodide(13.0mg, O.lOmmol) were added and stirred at 90 °C for 24 hours. The resulting product was distilled under the reduced pressure to remove dimethylformamide and purified by column chromatography to obtain the titled compound as a white solid ( 157mg, yield : 52.3%). 2) l-(2,3-Epoxypropyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4- pyrimidinedione l-Allyl-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione ( 157mg, 0.52mmol ) was dissolved in dichloromethane ( 10ml ), and thereto chloro perbenzoic acid ( 385mg, 1.56mmol ) was added. The resulting solution was refluxed for 24 hours, washed with a saturated solution of sodium bicarbonate, distilled under the reduced pressure to remove the used solvent and purified with column chromatography to obtain the titled compound as white solid ( 57 mg, yield : 35.0%). Example 138 : l-(2,3-Epoxypropyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 1) l-Allyl-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and allyl bromide were reacted by the same way with the example 45-1 to obtain the titled compound ( 225mg, yield : 75.1%). 2) l-(2,3-Epoxypropyl)-5-isopropyl-6-(3,5-dimethylphenoxy)- 2,4-pyrimidinedione l-Allyl-5-isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione was reacted by the same way with the example 45-2 to obtain the titled compound ( 80mg, yield : 37.2%). Example 139 : l-(2,3~Epoxypropyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 1) l-Allyl-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5~Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and allyl bromide were reacted by the same way with the example 45-1 to obtain the titled compound ( 190mg, yield : 60.8%). 2) 1 - (2,3-Epoxypropyl) -5-ethyl-6- (3,5-dimethylbenzoyl) -2,4- pyrimidinedione 1-Allyl-5-ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione was reacted by the same way with the example 45-2 to obtain the titled compound ( 73mg, yield : 40.3%). Example 140 : l-(2,3-Epoxypropyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 1) l-AUyl-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and allyl bromide were reacted by the same way with the example 45-1 to obtain the titled compound ( 211mg, yield : 64.3%). 2) l-(2,3~Epoxypropyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4- pyrimidinedione l-Allyl-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione was reacted by the same way with the example 45-2 to obtain the titled compound ( 86mg, yield : 39.0%). Example 141 : l-(lH-benzotriazol-l-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 1-chloromethyl-lH-benzotriazole were reacted by the same way with the example 1 to obtain the titled compound ( 112mg, yield : 28.6%). Example 142 : l-(lH-benzotriazol-l-ylmethyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and 1-chloromethyl-lH-benzotriazole were reacted by the same way with the example 1 to obtain the titled compound ( 108mg, yield : 26.6%). Example 143 : l-(lH-benzotriazol-l-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 1-chloromethyl-lH-benzotriazole were reacted by the same way with the example 1 to obtain the titled compound ( 135mg, yield : 33.5%). Example 144 : l-(lH-benzotriazol-l-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 1-chloromethyl-lH-benzotriazole were reacted by the same way with the example 1 to obtain the titled compound ( 152mg, yield : 36.4%). Example 145 : l-(Benzoxazol-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5~dimethylphenyl)thio-2,4-pyrimidinedione and 2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 176mg, yield : 43.2%). Example 146 : l-(Benzoxazol-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 189mg, yield : 44.8%). Example 147 : l-(Benzoxazol-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy) -2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 215mg, yield : 54.9%). Example 148 '■ l-(Benzoxazol-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy) -2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 207mg, yield : 51.1%). Example 149 : l-(Benzoxazol-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 241mg, yield : 59.7%). Example 150 : l-(Benzoxazol-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 236mg, yield : 56.5%). Example 151 : l-(3-Methoxycarbonyl-2-mranylmethyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 125mg, yield : 31.4%). Example 152 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4~pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrirnidinedione and 2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 139mg, yield : 33.7%). Example 153 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 139mg, yield : 36.4%). Example 154 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4~pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 133mg, yield : 33.5%). Example 155 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 150mg, yield : 38.0%). Example 156 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 162mg, yield : 39.7%). Example 157 : l-(Acetonyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4~ pyrimidinedione 5~Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and chloroacetone were reacted by the same way with the example 1 to obtain the titled compound ( 172mg, yield : 54%). Example 158 : l-(Acetonyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and chloroacetone were reacted by the same way with the example 1 to obtain the titled compound ( 155mg, yield : 45%). Example 159 : l-(Acetonyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and chloroacetone were reacted by the same way with the example 1 to obtain the titled compound ( 145mg, yield : 44%). Example 160 : l-(Acetonyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and chloroacetone were reacted by the same way with the example 1 to obtain the titled compound ( 155mg, yield : 45%). Example 161 '• l-(2-Butanon-l-yl)^5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and l-bromo-2-butanone were reacted by the same way with the example 1 to obtain the titled compound ( 185mg, yield : 56%). Example 162 : l-(2-Butanon-l-yl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and l-bromo-2-butanone were reacted by the same way with the example 1 to obtain the titled compound ( 179mg, yield : 49%). Example 163 : l-(2-Butanon-l-yl)-5-ethyl-6-(3,5-climethylbenzoyl)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and l-bromo-2-butanone were reacted by the same way with the example 1 to obtain the titled compound ( 182mg, yield •' 53%). Example 164 : l-(2-Butanon-l-yl)-5-isopropyl-6-(3,5-dimethylbenzoyl)~ 2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and l-bromo-2-butanone were reacted by the same way with the example 1 to obtain the titled compound ( 196mg, yield : 55%). Example 165 : l-(Phenacyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and 2-chloroacetophenone were reacted by the same way with the example 1 to obtain the titled compound ( 164mg, yield : 43%). Example 166 : l-(Phenacyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione 5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and 2-chloroacetophenone were reacted by the same way with the example 1 to obtain the titled compound ( 181mg, yield : 46%). Example 167 : l-(Phenacyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4~ pyrimidinedione 5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2-chloroacetophenone were reacted by the same way with the example 1 to obtain the titled compound ( 210mg, yield : 54%). Example 168 : l-(Phenacyl)-5-isopropyl-6-(3,5-dimethylbenzoyI)-2,4-pyrimidinedione 5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-chloroacetophenone were reacted by the same way with the example 1 to obtain the titled compound ( 164mg, yield : 43%). Physical properties of the compounds prepared by the above examples are as follows: (Table Removed) Activity and Toxicity Anti-HIV activity tests in vitro of the compounds according to the present invention were performed as described in J. Med. Chem, 34, 357, 1991. Inhibition by the compounds of virus-induced cytotoxic effect in MT-4 cells was measured as follows. MT-4 cells were suspended in culture media at 2.5xl05 cells/ml and infected with 1000 CCID50 ( 50% cell culture infective dose ) of HIV. Immediately after virus infection, 100//# of cell suspension was brought into each well of a flat-bottomed microtitray containing various concentrations of the test compounds. After 4 or 5 days incubation at 37°C, efficacy of the compounds was determined by the MTT method. Cytotoxicity of the compounds was assessed in parallel with their antiviral activity, based on viability of mock-infected host cells as determined by the MTT method. The results are shown in the following table. (Table Removed) Usefulness of the invention The present compounds have strong anti-HIV activity as well as very low toxicity, and thus they are expected to be used as potent antiviral agents. We claim: 1. A pyrimidinedione compound of general formula (I) (Formula Removed) wherein Rl represents C1-C4 alkyl, R2 and R3 represent independently hydrogen or C1-C4 alkyl and Y represents oxygen atom, sulfur atom or carbonyl, or a pharmaceutically acceptable salt thereof. 2. The compound of the general formula (I) as claimed in claim 1, wherein Rl is ethyl or isopropyl, and R2 and R3 are methyl. 3. A process for the preparation of a compound of the general formula (I) by reacting a compound of the formula (II) and a compound of the formula (III). (Formula Removed) wherein, Rl, R2, R3 and Y are as defined in claim 1, and Lie represents a conventional leaving group. 4. The process as claimed in claim 3, wherein the reaction is performed in a polar organic solvent in the presence of a base, at the temperature of 10 -100° C, for 1- 48 hours, and with the ratio of 1:0.8 -1:3 of the compound of the formula (II) and the compound of the formula (III). 5. The Compound as claimed in claim 1, as and when used for preparation of pharmaceutical compositions containing an antiviral compound of the general formula I or pharmaceutically acceptable salts thereof and pharmaceutically acceptable vehicles.

Full Text

Field of the invention
The present invention relates to novel pyrimidinedione derivatives or pharmaceutically acceptable salts thereof which are useful as antiviral agents, especially for treatment of AIDS, and process for the preparation thereof. Description of the prior art
Nowadays, there are about 15 chemotherapeutic agents for AIDS which were approved by the FDA. It has been known that such chemotherapeutic agents have medical action mechanisms to inhibit replication of AIDS virus.
However, they also have drug tolerance and undesirable side effects due to their toxicity. In order to solve these problems, many researches have been carried out to develope new antiviral chemotherapeutic agents with strong antiviral activity as well as lower toxicity.
Much researches to develop new antiviral agents for treatment of AIDS have been focused on pyrimidinedione derivatives, and thus the present inventors have synthesized various new pyrimidinedione derivatives by introducing homocarbocyclic groups to the N-1 position of pyrimidinedione derivatives, which compounds were applied for patent (see, WO97/30979, US patent 5,922,727), and they continued synthesis and evaluation of new derivatives prepared by introducing new homocarbocyclic groups, aryl and heteroaryl substituents, alkyl and aryl carbonylmethyl groups to the pyrimidinedione derivatives and studied their pharmacological effects. As the result, the inventors have found that the newly synthesized derivatives by the present invention have unexpectedly strong anti-HIV (Human Immunodeficiency Virus) activity as well as very low toxicity.
Summary of the invention Accordingly, an object of the present invention is to provide new

pyrimidinedione derivatives of the following formula (I) or pharmaceutically acceptable salts thereof which have strong antiviral activity against HIV.
(Formula Removed)
wherein R represents cyclopropyl; cyclobutyl; cyclohexyl; unsubstituted or mono-, di- or tri-substituted phenyl with a group selected from hydroxy, C1-C4 alkyl, C1-C4 alkoxy, halogen, trifluoromethyl, cyano and amino; 1- or 2-naphthyl; 9-anthracenyl; 2-anthraquinonyl; unsubstituted or substituted pyridyl with a group selected from C1-C4 alkyl, C1-C4 alkoxy, cyano and halogen; 2-, 3- or 4-quinolinyl; oxiranyl; 1-benzotriazolyl; 2-benzoxazolyl; furanyl substituted with C1-C4 alkoxycarbonyl; C1-C4 alkylcarbonyl; or benzoyl, R1 represents halogen or C1-C4 alkyl,
R2 and R3 represent independently hydrogen orC1-C4 alkyl, X represents oxygen atom, and Y represents oxygen atom, sulfur atom or carbonyl.
Another object of the invention is to provide a process for the preparation of the compounds of the general formula (I) or pharmaceutically acceptable salts thereof.
The other object of the invention is to provide pharmaceutical preparations having antiviral activity which contains the compound of the general formula (I) or a pharmaceutically acceptable salt thereof as the active ingredient.
Detailed description of the invention
The compounds of the general formula (I) according to the present invention may be prepared by the following reaction scheme 1.

Scheme 1

(Scheme Removed)

wherein R, R1, R2, R3, X and Y are as defined above, and Lie represents a conventional leaving group such as halogen, alkylsulfonyl and arylsulfonyl.
The compounds of the general formula (I) may be prepared by reacting a compound of the general formula (II) with a compound of the general formula (III) in a conventional organic solvent and in the presence of a base.
The base used in the above reaction may include anhydrous sodium bicarbonate, anhydrous sodium carbonate, sodium hydride and anhydrous potassium carbonate.
The organic solvent used in the reaction may include an organic polar solvent such as dimethylformamide, acetonitrile and dimethylsulfoxide.
In addition, a catalyst such as potassium iodide, lithium iodide or the like may be used.
The reaction may be carried out preferably at the temperature of 10 — 100°C for 1-48 hours.
6-substituted pyrimidinedione derivatives of the formula (II) used in the present invention may be prepared as described in WO 93/02044 and WO 95/18109, or by using a similar method thereto.
The compounds of the formula (I) may form an addition salt with a pharmaceutically acceptable inorganic or organic acid or base; for example, bases such as salts of alkali metal and alkaline earth metal including sodium, potassium, magnesium and calcium; inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid and nitric acid; organic acids such as formic acid, acetic acid, propionic

acid, succinic acid, citric acid, maleic acid, glycolic aicd, lactic acid and malonic acid; amino acids such as serine, cysteine, cystine, asparagine, glutamine, lysine, arginine, leucine and proline; sulfonic acids such as methane sulfonate, ethane sulfonate, benzene sulfonate and toluene sulfonate.
The compounds of the general formula (I) or pharmaceutically acceptable salts thereof may be formulated into conventional pharmaceutical preparations in combination with pharmaceutically acceptable vehicles or carriers, whereby the preparations may be used for treatment or prevention of various viral diseases.
Examples
The compounds of the general formula (I) defined in the following table were prepared in the following examples.
(Table Removed)

Example 1: l-(Cyclopropyl)methyl-5-ethyl-6-(3,5-dimethylphenyl)-
thio-2,4-pyrimidinedione
To a solution of 5-ethyl-6-(3,5~dimethylphenyl)thio-2,4-pyrimidinedione ( 276mg, l.Ommol ) and bromomethyl cyclopropane ( 160mg, l.Ommol, 85% ) dissolved in dimethylformamide ( 5ml ), sodium bicarbonate ( 126mg, 1.50mmol ) and lithium iodide ( 13.0mg, 0.l0mmol ) were added. The resulting mixture was stirred at 90°C for 24 hrs, distilled under the reduced pressure to remove dimethylformamide and purified with column chromatography to obtain the titled compound as a white solid ( 152 mg, yield : 46.0%).
Example 2'- l-(Cyclopropyl)methyl-5-isopropyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
bromomethyl cyclopropane were reacted by the same way with the example 1 to obtain the titled compound ( 170mg, yield : 49.4%). Example 3: l-(Cyclopropyl)methyl-5-ethyl-6-(3,5-dimethylphenoxy)"2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and bromomethyl cyclopropane were reacted by the same way with the example 1 to obtain the titled compound ( 146mg, yield : 46.4%).
Example 4: 1 - (Cyclopropyl)methyl-5-isopropyl-6- (3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5~dimethylphenoxy )-2,4-pyrimidinedione and
bromomethyl cyclopropane were reacted by the same way with the example 1 to obtain the titled compound ( 132mg, yield : 40.2%). Example 5: l-(Cyclopropyl)methyl-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and bromomethyl cyclopropane were reacted by the same way with the example 1 tc obtain the titled compound ( 165mg, yield : 50.6%).
Example 6: l-(Cyclopropyl)methyl-5-isopropyl-6-(3,5-dimethylbenzoyI)-2,4 - py rimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
bromomethyl cyclopropane were reacted by the same way with the example 1 to obtain the titled compound ( 158mg, yield : 46.4%).
Example 7: l-(Cyclobutyl)methyl-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and (cyclobutyl) methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 150mg, yield : 43.5%). Example 8: l-(Cyclobutyl)methyl-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5~Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
(cyclobutyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 147mg, yield : 41.0%).
Example 9: l-(Cyclobutyl)methyl-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and (cyclobutyl)-methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 192mg, yield : 58.5%). Example 10: 1 - (Cyclobutyl)methyl-5-isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
(cyclobutyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 164mg, yield : 47.9%).
Example 11: l-(Cyclobutyl)methyl-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ehtyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and (cyclobutyl)-methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 179mg, yield : 52.6%). Example 12: l-(Cyclobutyl)methyl-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
(cyclobutyl)methyl para-toluenesulfonate were reacted by the same way
with the example 1 to obtain the titled compound ( 182mg, yield : 51.3%).
Example 13: l-(Cyclohexyl)methyl-5-ethyl-6-(3,5-dimethylphenyl)thio-
2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
(cyclohexyl)methyl para-toluenesulfonate were reacted by the same way
with the example 1 to obtain the titled compound ( 195mg, yield •'
52.3%).
Example 14: l-(Cyclohexyl)methyl-5-isopropyl-6-(3,5-dimethylphenyl)-
thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
(cyclohexyl)methyl para-toluenesulfonate were reacted by the same way
with the example 1 to obtain the titled compound ( 210mg, yield •'
54.3%).
Example 15: l-(Cydohexyl)methyl-5-ethyl-6-(3,5~dimethylphenoxy)-2,4-
pyrimidinedione
5-Ethyl-6~(3,5-dimethylphenoxy)-2,4-pyrimidinedione and (cyclohexyl) -methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 185mg, yield : 51.9%). Example 16: 1 - (Cyclohexyl)methyl-5-isopropyl -6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione
5-Isopropyl -6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
(cyclohexyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 201mg, yield : 54.3%).
Example 17: l-(Cyclohexyl)methyl-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and (cyclohexyl)-
methyl para-toluenesulfonate were reacted by the same way with the
example 1 to obtain the titled compound ( 233mg, yield : 63.2%).
Example 18: l-(Cyclohexyl)methyl-5-isopropyl-6-(3,5-dimethylbenzoyl)-
2,4- pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and

(cyclohexyl)methyl para-toluenesulfonate were reacted by the same way with the example 1 to obtain the titled compound ( 212mg, yield : 55.4%).
Example 19: l-Benzyl-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidine dione
5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 275mg, yield : 75.0%).
Example 20: l-Benzyl-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4-
pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 300mg, yield : 79.0%).
Example 21: l-Benzyl-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidine-dione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 285mg, yield : 72.5%).
Example 22: l-Benzyl-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-
pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4_pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 264mg, yield : 72.5%).
Example 23: l-Benzyl-5-ethyl-6- (3,5-dimethylbenzoyl)-2,4-pyrimidine-dione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and benzyl
bromide were reacted by the same way with the example 1 to obtain the titled compound ( 289mg, yield : 79.8%).
Example 24: l-Benzyl-5-isopropyl-6-(3,5-dimethylbenzoyl)~2,4-
pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)~2,4-pyrimidinedione and benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 293mg, yield : 78.0%).

Example 25: l-(3-Methoxybenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3-methoxylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 175mg, yield : 44.1%). Example 26: l-(3-Methoxybenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3-methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 203mg, yield : 49.4%). Example 27: l-(3-Methoxybenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
3-methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 213mg, yield : 56.0%) Example 28: 1 -(3-Methoxybenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4"Pyrimidinedione and
3-methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 217mg, yield : 55.0%). Example 29: l-(3-Methoxybenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)~2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
3-methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 252mg, yield : 64.2%). Example 30: l-(3-Methoxybenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
3-methpoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 235mg, yield : 57.8%). Example 31: l-(4-Trifluoromethoxybenzyl)-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4~pyrimidinedione and 4-trifluoro-

methoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 195mg, yield : 43.3%). Example 32: l-(4-Trifluoromethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-pheny 1) thio - 2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 208mg, yield : 44.8%). Example 33: l-(4-Trifluoromethoxybenzyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione
5~Ethyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and
4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 233mg, yield : 53.6%). Example 34: l-(4-Trifluoromethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy)~2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and
4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 212mg, yield : 47.3%). Example 35: l-(4-Trifluoromethoxybenzyl)-5-ethyl-6-(3,5-dimethyl-benzoyl) - 2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 285mg, yield : 63.8%). Example 36: l-(4-Trifluoromethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
4-trifluoromethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 304mg, yield : 66.0%). Example 37: l-(2-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio~2,4-pyrimidinedione and
2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 162mg, yield : 41.3%). Example 38: l-(2-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)-

thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 188mg, yield : 46.4%). Example 39: l-(2-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 201mg, yield : 53.5%). Example 40: l-(2-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 154mg, yield : 39.5%). Example 41". l-(2-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 199mg, yield : 51.4%).
Example 42: l-(2-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 231mg, yield : 57.5%). Example 43: l-(3-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 185mg, yield : 47.3%) Example 44: l-(3-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3-cyanobenzyl bromide were reacted by the same way with the example

1 to obtain the titled compound ( 176mg, yield : 43.4%).
Example 45: l-(3-Cyanobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 216mg, yield : 57.5%). Example 46: l-(3-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4~ pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 193mg, yield : 49.6%). Example 47: 1- (3-Cyanobenzyl)-5-ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione
5~Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 207mg, yield : 53.4%).
Example 48: l-(3-Cyanobenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
3-cyanobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 222mg, yield : 55.3%). Example 49: l-(3,5-Dimethylbenzyl)-5-ethyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 265mg, yield : 67.2%). Example 50: l-(3,5-Dimethylbenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethy lphenyl)thio-2,4-pyrimidinedione and
3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (230mg, yield : 56.3%). Example 51: l-(3,5-Dimethylbenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione

5-Ethyl-6-(3,5~climethylphenoxy)-2,4-pyrimidinedione and
3,5-dimethylbenzyl bromide were reacted by the same way with the
example 1 to obtain the titled compound (217mg, yield : 57.3%).
Example 52: l-(3,5-Dimethylbenzyl)-5-isopropyl-6-(3,5-dimethyl-
phenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (260mg, yield : 66.2%). Example 53: l-(3,5-Dimethylbenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (288mg, yield : 73.8%). Example 54: 1- (3,5-Dimethylbenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
3,5-dimethylbenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (322mg, yield : 79.5%). Example 55: l-(3,5-Dimethoxybenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (252mg, yield : 59.1%). Example 56: l-(3,5-Dimethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (234mg, yield '• 53.1%). Example 57: l-(3,5-Dimethoxybenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (279mg, yield : 68.0%).

Example 58: l-(3,5-Dimethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy) -2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
3,5-dimethoxybenzyl bromide were reacted by the same way with the
example 1 to obtain the titled compound (275mg, yield : 64.8%).
Example 59: l-(3,5-Dimethoxybenzyl)-5-ethyl-6-(3,5-dimethyl-
benzoyl)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (212mg, yield : 50.2%). Example 60: l-(3,5-Dimethoxybenzyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
3,5-dimethoxybenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (296mg, yield : 67.8%). Example 61: l-[3,5-Bis(trifluoromethyl)benzyl]-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way
with the example 1 to obtain the titled compound (226mg, yield : 45.0%).
Example 62: l-[3,5-Bis(trifluoromethyl)benzyl]-5-isopropyl-6-(3,5-
dimethylphenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (195mg, yield : 37.8%). Example 63: l-[3,5-Bis(Trifluoromethyl)benzyl]-5-ethyl-6-(3,5-dimethyl-phenoxy) - 2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (240mg, yield : 49.4%). Example 64: l-[3,5-Bis(Trifluoromethyl)benzyl]-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and

3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (266mg, yield : 53.2%) Example 65: l-[3,5-Bis(Trifluoromethyl)benzyl]-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Ethyl~6- (3,5-dimethylbenzoyl) - 2,4-pyrimidinedione and
3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (280mg, yield : 56.2%). Example 66: l-[3,5-Bis(Trifluoromethyl)benzyl]-5-isopropyl~6- (3,5-dimethylbenzoyl ) -2,4- pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
3,5-bis(trifluoromethyl)benzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (255mg, yield '• 49.8%) Example 67: l-(2,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5~Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (170mg, yield : 42.2%). Example 68: l-(2,5-Difluorobenzyl)-5-isopropyl~6-(3,5~dimethylphenyl)-thio-2,4-pyrimidinedione
5-Isopropy 1 -6 - (3,5-dimethy lpheny 1) thio - 2,4 - pyrimidinedione and
2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (205mg, yield : 49.2%). Example 69: l-(2,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy )-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (185mg, yield : 47.9%). Example 70: l-(2,5-Difluorobenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl~6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and
2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (165mg, yield : 41.2%). Example 71: 1 - (2,5-Difluorobenzyl)-5-ethyl-6- (3,5-dimethylbenzoyl) -2,4-

pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (214mg, yield '■ 53.7%). Example 72: 1 -(2,5-Difluorobenzyl)-5-isopropyl-6- (3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimetriylbenzoyl)-2,4-pyrimidinedione and
2,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (200mg, yield : 48.5%). Example 73: l-(3,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (196mg, yield : 48.7%). Example 74: 1 - (3,5-Difluorobenzyl) -5~isopropyl-6- (3,5-dimethylphenyl) -thio-2,4-pyrimidinedione
5-Isopropyl~6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (205mg, yield : 49.2%). Example 75: l-(3,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (195mg, yield : 50.5%). Example 76: l-(3,5-Difluorobenzyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (180mg, yield : 45.0%). Example 77: l-(3,5-Difluorobenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
3,5-difluorobenzyl bromide were reacted by the same way with the

example 1 to obtain the titled compound (236mg, yield : 59.2%). Example 78: l-(3,5-Difluorobenzyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
3,5-difluorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (220mg, yield : 53.3%). Example 79: 1- (3,5-Dichlorobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (292mg, yield "• 67.1%). Example 80: 1 - (3,5-Dichlorobenzyl)-5-isopropyl-6- (3,5-dimethylphenyl) -thio-2,4-pyrimidinedione
5-isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (250mg, yield : 55.6%). Example 81: 1 - (3,5-Dichlorobenzyl)-5-ethyl-6- (3,5-dimethylphenoxy)-2,4-pyrimidinedione
5~Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
3,5-dichlorobenzyl bromide were reacted by the same way with the
example 1 to obtain the titled compound (220mg, yield •' 52.7%).
Example 82'- l-(3,5-Dichlorobenzyl)-5-isopropyl-6-(3,5-dimethyl-
phenoxy)-2,4-pyrimidinedione
5-isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (235mg, yield : 54.2%). Example 83: l-(3,5~Dichlorobenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzol)-2,4-pyrimidinedione and
3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (287mg, yield : 66.5%). Example 84: 1- (3,5-Dichlorobenzyl) ~5-isopropyl-6~ (3,5-dimethylbenzoyl) -2,4-pyrimidinedione

5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
3,5-dichlorobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (283mg, yield : 63.6%). Example 85: l-(3,5-Dibromobenzyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl~6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (356mg, yield : 67.9%). Example 86: l-(3,5-Dibromobenzyl)-5-isopropyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (380mg, yield : 70.6%). Example 87: l-(3,5-Dibromobenzyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl~6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (375mg, yield : 73.9%). Example 88: l-(3,5-Dibromobenzyl)-5-isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and
3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (395mg, yield : 75.6%). Example 89: l-(3,5-Dibromobenzyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (387mg, yield : 74.4%). Example 90: 1- (3,5-Dibromobenzyl) -5-isopropyl~6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione ana
3,5-dibromobenzyl bromide were reacted by the same way with the example 1 to obtain the titled compound (402mg, yield : 75.2%).

Example 91: l-(2-Naphthalenemethyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (265mg, yield : 63.6%). Example 92: l-(2-Naphthalenemethyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (298mg, yield : 69.2%). Example 93: l- (2-Naphthalenemethyl)-5-ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (272mg, yield : 67.9%). Example 94: l-(2-Naphthalenemethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy) -2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (274mg, yield : 66.1%). Example 95: l-(2-Naphthalenemethyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-bromomethyl naphthalene were reacted by the same way with the example 1 to obtain the titled compound (251mg, yield : 60.9%). Example 96: l-(2-Naphthalenemethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-bromomethyl naphthalene were reacted by the same way with the
example 1 to obtain the titled compound (274mg, yield : 64.2%).
Example 97: l-(Anthracen-9-ylmethyl)-5-ethyl-6-(3,5-dimethylphenyl)-
thio-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and

9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound (195mg, yield : 41.8%). Example 98: l-(Anthracen-9-ylmethyl)-5-isopropyl-6-(3,5-dimethyl~ phenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
9-chloromethyl anthracene were reacted by the same way with the
example 1 to obtain the titled compound (215mg, yield : 44.7%).
Example 99: l-(Anthracen-9-ylmethyl)-5-ethyl-6-(3,5-dimethyl-
phenoxy) -2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound (187mg, yield : 41.5%). Example 100: l-(Anthracen-9-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy) - 2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
9-chloromethyl anthracene were reacted by the same way with the
example 1 to obtain the titled compound (205mg, yield : 44.1%).
Example 101 : l-(Anthracen-9-ylmethyl)-5-ethyl-6-(3,5-dimethyl-
benzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound ( 216mg, yield : 46.7%). Example 102 : l-(Anthracen-9-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl) -2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
9-chloromethyl anthracene were reacted by the same way with the example 1 to obtain the titled compound ( 192mg, yield '■ 40.3%). Example 103 : l-(Anthraquinon-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 175mg, yield : 35.1%). Example 104 : l-(Anthraquinon-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-

pheny 1) thio - 2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 165mg, yield : 32.2%). Example 105 : l-(Anthraquinon-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 175mg, yield : 36.3%). Example 106 : l-(Anthraquinon-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 155mg, yield : 31.2%). Example 107 : l-(Anthraquinon-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 178mg, yield : 36.0%). Example 108 : l-(Anthraquinon-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
2-chloromethyl anthraquinone were reacted by the same way with the example 1 to obtain the titled compound ( 193mg, yield : 38.0%). Example 109 : l-(Pyridin-2-ylmethyl)-5-ethyl-6-(3,5-dimethylphenyl)-thio-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 98mg, yield : 26.7%).
Example 110 : l-(Pyridin-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-picolyl chloride were reacted by the same way with the example 1 to

obtain the titled compound ( 112mg, yield : 29.4%).
Example 111 : l-(Pyridin-2-ylmethyl)-5-ethyl-6-(3,5-dimethylphenoxy)-
2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 125mg, yield : 35.6%).
Example 112 : l-(Pyridin-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 136mg, yield : 37.2%).
Example 113 : l-(Pyridin-2-ylmethyl)-5-ethyl-6~(3,5-dimethyl-benzoyl) -2,4-pyrimidinedione
5-Ethyl~6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 145mg, yield •' 39.9%).
Example 114 : l-(Pyridm-2-2ylmethyl)-5-isopropyl-6-(3,5-dirnethyl-benzoyl) -2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 2-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 135mg, yield : 35.8%).
Example 115 : l-(Pyridm-3-ylmethyl)-5-etiiyl-6-(3,5-dimethyl-phenyl) thio - 2,4 - py rimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 95mg, yield : 25.9%).
Example 116 •' l-(Pyridin-3-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Isopropyl~6- (3,5-dimethylphenyl)thio-2,4~pyrimidinedione and
3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 88mg, yield : 23.1%).
Example 117 : l-(Pyridin-3-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)~2,4-pyrimidinedione

5-ethyl-6-(3,5-dimethylphenoxy)-2,4~pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( lOlmg, yield : 28.7%).
Example 118 : l-(Pyridin-3-ylmethyl)-5-isopropyl-6-(3,5-dimethyl~ phenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 122mg, yield : 33.4%).
Example 119 : l~(Pyridin-3-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 120mg, yield '• 33.0%).
Example 120 : l-(Pyridin-3-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl) -2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and 3-picolyl chloride were reacted by the same way with the example 1 to obtain the titled compound ( 152mg, yield '• 40.3%).
Example 121 "• l-(2-Chloropyridin-6-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 122mg, yield : 30.4%). Example 122 : l-(2-Chloropyridin-6-ylmethyl)-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-chloro-6-picolyl bromide were reacted by the same way with the
example 1 to obtain the titled compound ( 130mg, yield : 31.3%).
Example 123 : l-(2-Chloropyridin-6-ylmethyl)-5-ethyl-6-(3,5-
dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione ana
2-chloro-6~picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 126mg, yield : 32.7%).

Example 124 : l-(2-Chloropyridin-6-ylmethyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 135mg, yield : 33.8%). Example 125 : l-(2-Chloropyridin-6-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl) -2,4-pyrimidinedione
5-Ethyl-6- (3,5-climethylbenzoyl) -2,4-pyrimidinedione and
2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 145mg, yield : 36.4%). Example 126 : l-(2-Chloropyridin-6-ylmethyl)-5-isopropyl-6-(3,5~ dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-chloro-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 155mg, yield : 37.6%). Example 127 : l-(2-Bromopyridin-6-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
2-bromo-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 143mg, yield : 33.2%). Example 128 : l-(2-Bromopyridin-6-ylmethyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-bromo-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 167mg, yield : 37.6%). Example 129 : l-(2-Bromopyridib-6-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
2-bromo-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 149mg, yield : 35.3%). Example 130 : l-(2-Bromopyridin-6-ylmethyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and

2-bromo-6-picolyl bromide were reacted by the same way with the example 1 to obtain the titled compound ( 148mg, yield : 32.4%). Example 131 : l-(Quinolin-2-ylmethyl)-5~ethyl-6-(3,5-dimemylphenyl)-thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 138mg, yield : 33.1%). Example 132 : l-(Quinolin-2-ylmemyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound { 125mg, yield : 29.0%). Example 133 : l-(Quinolin-2~ylmethyl)-5-ethyl-6-{3,5-dimethyl-phenoxy)-2,4-pyrimidinedione
5-Ethyl-6~ (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 130mg, yield : 32.4%). Example 134 : l-(Quinolin-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 139mg, yield •' 33.5%). Example 135 : l-(Quinolin-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4~pyrimidinedione and
2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 159mg, yield : 38.5%). Example 136 : l-(Qumolin-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoy 1) - 2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-chloromethyl quinoline were reacted by the same way with the example 1 to obtain the titled compound ( 170mg, yield : 39.8%). Example 137 '■ l-(2,3~Epoxypropyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-

pyrimidinedione
1) l-Allyl-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
To a solution of 5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione (258mg, l.Ommol) and allyl bromide(121mg, l.Ommol) dissolved in dimethylformamide(5ml), sodium bicarbonate (126mg, 1.50mmol) and lithium iodide(13.0mg, O.lOmmol) were added and stirred at 90 °C for 24 hours. The resulting product was distilled under the reduced pressure to remove dimethylformamide and purified by column chromatography to obtain the titled compound as a white solid ( 157mg, yield : 52.3%).
2) l-(2,3-Epoxypropyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-
pyrimidinedione
l-Allyl-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione (
157mg, 0.52mmol ) was dissolved in dichloromethane ( 10ml ), and thereto chloro perbenzoic acid ( 385mg, 1.56mmol ) was added. The resulting solution was refluxed for 24 hours, washed with a saturated solution of sodium bicarbonate, distilled under the reduced pressure to remove the used solvent and purified with column chromatography to obtain the titled compound as white solid ( 57 mg, yield : 35.0%). Example 138 : l-(2,3-Epoxypropyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
1) l-Allyl-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and allyl
bromide were reacted by the same way with the example 45-1 to obtain the titled compound ( 225mg, yield : 75.1%).
2) l-(2,3-Epoxypropyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-
2,4-pyrimidinedione
l-Allyl-5-isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione was reacted by the same way with the example 45-2 to obtain the titled compound ( 80mg, yield : 37.2%).
Example 139 : l-(2,3~Epoxypropyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
1) l-Allyl-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione

5~Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and allyl bromide were reacted by the same way with the example 45-1 to obtain the titled compound ( 190mg, yield : 60.8%).
2) 1 - (2,3-Epoxypropyl) -5-ethyl-6- (3,5-dimethylbenzoyl) -2,4-
pyrimidinedione
1-Allyl-5-ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione was
reacted by the same way with the example 45-2 to obtain the titled compound ( 73mg, yield : 40.3%).
Example 140 : l-(2,3-Epoxypropyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
1) l-AUyl-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and allyl
bromide were reacted by the same way with the example 45-1 to obtain the titled compound ( 211mg, yield : 64.3%).
2) l-(2,3~Epoxypropyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-
pyrimidinedione
l-Allyl-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione was reacted by the same way with the example 45-2 to obtain the titled compound ( 86mg, yield : 39.0%).
Example 141 : l-(lH-benzotriazol-l-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
1-chloromethyl-lH-benzotriazole were reacted by the same way with the example 1 to obtain the titled compound ( 112mg, yield : 28.6%). Example 142 : l-(lH-benzotriazol-l-ylmethyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and
1-chloromethyl-lH-benzotriazole were reacted by the same way with the example 1 to obtain the titled compound ( 108mg, yield : 26.6%). Example 143 : l-(lH-benzotriazol-l-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
1-chloromethyl-lH-benzotriazole were reacted by the same way with the

example 1 to obtain the titled compound ( 135mg, yield : 33.5%). Example 144 : l-(lH-benzotriazol-l-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
1-chloromethyl-lH-benzotriazole were reacted by the same way with the example 1 to obtain the titled compound ( 152mg, yield : 36.4%). Example 145 : l-(Benzoxazol-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5~dimethylphenyl)thio-2,4-pyrimidinedione and
2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 176mg, yield : 43.2%). Example 146 : l-(Benzoxazol-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenyl)thio-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 189mg, yield : 44.8%). Example 147 : l-(Benzoxazol-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-phenoxy) -2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 215mg, yield : 54.9%). Example 148 '■ l-(Benzoxazol-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-phenoxy) -2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 207mg, yield : 51.1%). Example 149 : l-(Benzoxazol-2-ylmethyl)-5-ethyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 241mg, yield : 59.7%). Example 150 : l-(Benzoxazol-2-ylmethyl)-5-isopropyl-6-(3,5-dimethyl-benzoyl)-2,4-pyrimidinedione

5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-chloromethyl benzoxazole were reacted by the same way with the example 1 to obtain the titled compound ( 236mg, yield : 56.5%). Example 151 : l-(3-Methoxycarbonyl-2-mranylmethyl)-5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenyl)thio-2,4-pyrimidinedione and
2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 125mg, yield : 31.4%).
Example 152 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-isopropyl-6-(3,5-dimethylphenyl)thio-2,4~pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenyl)thio-2,4-pyrirnidinedione and
2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 139mg, yield : 33.7%).
Example 153 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 139mg, yield : 36.4%).
Example 154 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4~pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 133mg, yield : 33.5%).
Example 155 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 150mg, yield : 38.0%).

Example 156 : l-(3-Methoxycarbonyl-2-furanylmethyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-bromomethyl-3-methoxycarbonylfurane were reacted by the same way with the example 1 to obtain the titled compound ( 162mg, yield : 39.7%).
Example 157 : l-(Acetonyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4~ pyrimidinedione
5~Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and chloroacetone were reacted by the same way with the example 1 to obtain the titled compound ( 172mg, yield : 54%).
Example 158 : l-(Acetonyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
chloroacetone were reacted by the same way with the example 1 to obtain the titled compound ( 155mg, yield : 45%).
Example 159 : l-(Acetonyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and chloroacetone were reacted by the same way with the example 1 to obtain the titled compound ( 145mg, yield : 44%).
Example 160 : l-(Acetonyl)-5-isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
chloroacetone were reacted by the same way with the example 1 to obtain the titled compound ( 155mg, yield : 45%).
Example 161 '• l-(2-Butanon-l-yl)^5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione and
l-bromo-2-butanone were reacted by the same way with the example 1 to obtain the titled compound ( 185mg, yield : 56%).
Example 162 : l-(2-Butanon-l-yl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione

5-Isopropyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
l-bromo-2-butanone were reacted by the same way with the example 1 to obtain the titled compound ( 179mg, yield : 49%).
Example 163 : l-(2-Butanon-l-yl)-5-ethyl-6-(3,5-climethylbenzoyl)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
l-bromo-2-butanone were reacted by the same way with the example 1 to obtain the titled compound ( 182mg, yield •' 53%).
Example 164 : l-(2-Butanon-l-yl)-5-isopropyl-6-(3,5-dimethylbenzoyl)~ 2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
l-bromo-2-butanone were reacted by the same way with the example 1 to obtain the titled compound ( 196mg, yield : 55%).
Example 165 : l-(Phenacyl)-5-ethyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Ethyl-6- (3,5-dimethylphenoxy) -2,4-pyrimidinedione and
2-chloroacetophenone were reacted by the same way with the example 1 to obtain the titled compound ( 164mg, yield : 43%).
Example 166 : l-(Phenacyl)-5-isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione
5-Isopropyl-6- (3,5-dimethylphenoxy )-2,4-pyrimidinedione and
2-chloroacetophenone were reacted by the same way with the example 1 to obtain the titled compound ( 181mg, yield : 46%).
Example 167 : l-(Phenacyl)-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4~ pyrimidinedione
5-Ethyl-6- (3,5-dimethylbenzoyl) -2,4-pyrimidinedione and
2-chloroacetophenone were reacted by the same way with the example 1 to obtain the titled compound ( 210mg, yield : 54%).
Example 168 : l-(Phenacyl)-5-isopropyl-6-(3,5-dimethylbenzoyI)-2,4-pyrimidinedione
5-Isopropyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidinedione and
2-chloroacetophenone were reacted by the same way with the example 1 to obtain the titled compound ( 164mg, yield : 43%).

Physical properties of the compounds prepared by the above examples are as follows:
(Table Removed)

Activity and Toxicity
Anti-HIV activity tests in vitro of the compounds according to the present invention were performed as described in J. Med. Chem, 34, 357, 1991. Inhibition by the compounds of virus-induced cytotoxic effect in MT-4 cells was measured as follows.
MT-4 cells were suspended in culture media at 2.5xl05 cells/ml and infected with 1000 CCID50 ( 50% cell culture infective dose ) of HIV. Immediately after virus infection, 100//# of cell suspension was brought into each well of a flat-bottomed microtitray containing various concentrations of the test compounds. After 4 or 5 days incubation at 37°C, efficacy of the compounds was determined by the MTT method. Cytotoxicity of the compounds was assessed in parallel with their antiviral activity, based on viability of mock-infected host cells as determined by the MTT method.
The results are shown in the following table.
(Table Removed)

Usefulness of the invention
The present compounds have strong anti-HIV activity as well as very low toxicity, and thus they are expected to be used as potent antiviral agents.

We claim:
1. A pyrimidinedione compound of general formula (I)
(Formula Removed)
wherein
Rl represents C1-C4 alkyl,
R2 and R3 represent independently hydrogen or C1-C4 alkyl and
Y represents oxygen atom, sulfur atom or carbonyl,
or a pharmaceutically acceptable salt thereof.
2. The compound of the general formula (I) as claimed in claim 1, wherein Rl is ethyl or isopropyl, and R2 and R3 are methyl.
3. A process for the preparation of a compound of the general formula (I) by reacting a compound of the formula (II) and a compound of the formula (III).
(Formula Removed)
wherein, Rl, R2, R3 and Y are as defined in claim 1, and Lie represents a conventional leaving group.
4. The process as claimed in claim 3, wherein the reaction is performed in a polar organic
solvent in the presence of a base, at the temperature of 10 -100° C, for 1- 48 hours, and with
the ratio of 1:0.8 -1:3 of the compound of the formula (II) and the compound of the formula
(III).
5. The Compound as claimed in claim 1, as and when used for preparation of pharmaceutical compositions containing an antiviral compound of the general formula I or pharmaceutically acceptable salts thereof and pharmaceutically acceptable vehicles.

Documents:

http://ipindiaonline.gov.in/patentsearch/GrantedSearch/viewdoc.aspx?id=skya81jDe/BSqS81EY5OF28zG2nKpIem7rDGH6yXCFg=&loc=+mN2fYxnTC4l0fUd8W4CAA==

« Previous Patent

Next Patent »

Patent Number

269372

Indian Patent Application Number

IN/PCT/2000/00411/DEL

PG Journal Number

43/2015

Publication Date

23-Oct-2015

Grant Date

18-Oct-2015

Date of Filing

11-Dec-2000

Name of Patentee

SAMJIN PHARMACEUTICAL CO., LTD,

Applicant Address

338-8, SEOKYO-DONG, MAPO-KU, 121-739 SEOUL REPUBLIC OF KOREA

Inventors:

#	Inventor's Name	Inventor's Address
1	CHO, EUI-HWAN	#105-101 HYUNDAL 1-CHA APT. 653 KAEPO 1-DONG, KANGAM-GU, SEOUL 135-241, KOREA
2	LEE SUN-HWAN	#105-403, DAERIM APT., DOKGOK-DONG, PYONGTAEK, KYUNGKI-DO 459-100, KOREA
3	CHUNG, SUN-GAN	#206-1603 LG VILLAGE APT. 530 KEUMGOK-DONG, KWONSON-GU, SUWON, KYUNGKI-DO 441-460 KOREA
4	KWON, HO-SEOK,	#506-1105 SINDONGA APT. 1274 KWONGSON-DONG, SUWON, KYUNGKI-DO 441-390, KOREA
5	LEE, JAE-EUNG,	390-3 SIN-JANG 2-DONG, HANAM, KYUNGKI-DO 465-032, KOREA
6	JOO JEONG-HO	#107-301, BAEKZO APT. SEOKSU 1-DONG, MANAN-GU, ANYANG, KYUNGKI-DO 430041, KOREA.

PCT International Classification Number

C07D 239/54

PCT International Application Number

PCT/KR00/00328

PCT International Filing date

2000-04-08

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	1999-12629	1999-04-10	Republic of Korea