Title of Invention

UREA AMIDE DERIVATIVE

Abstract The present invention relates to novel urea amide derivative. Organic acids which are in its liquid corrosive forms are converted to powder urea amides which are corrosive free and ensuring ease in handling. As the urea amides get converted to urea and organic acids in the gut of the animal, the organic acids perform their role at their best.
Full Text
The present invention relates to novel urea amide derivative. This invention also relates to a process of preparing the same. The present invention also relates to the use of urea amide derivative of the present invention in the animal feed as acidifiers, growth promoters, preservatives, anti-microbial agents and antibacterial agents.
Addition of organic acids like formic acid, acetic acid, propionic acid, butyric acid, pentanoic acid, hexanoic acid, heptanoic acid and octanoic acid and substituted compounds of the above like methionine hydroxy analog in animal feeds has proven to help in improving the health and performance of animals. Organic acids work as acidifiers by vastly reducing the bacterial load in the digestive tract thereby improving the animal's health. The disadvantage of using organic acids is that organic acids being acidic in nature are corrosive. The next disadvantage is that it is difficult to handle the liquids, as most of the used organic acids are liquids. In the present state of art to overcome the above said problems the organic acids are used in their salt form as this enables converting a liquid into a powder form and also reduce corrosion. Though the problems appeared to be solved by this approach but still a lacuna in this procedure was found that the required acidic nature of these acids is vastly curtailed thereby reducing its main role of maintaining the required acidic pH in the animal gut. When the salt form of organic acids are used as feed additives, these salts reacts bv the influence of hydrochloric acid generated insitu in the gut thereby reducing the required acidity needed for digestion. Under this condition the microbial growth such as bacterial growth is not curtailed which defeats the very purpose of adding the organic acids.
Therefore there was a need for continuous research to reap the benefits of the use of organic acids as acidifiers in the animal feed without compromising on any disadvantages. Surprisingly it was found that novel urea amide derivatives as herein described are extremely useful in achieving the objects of the present invention.
The object of the present invention is to provide an animal feed that contains the acidifiers having no corrosive property.
The next object of the invention is to provide on animal feed that contains the acidifiers having no corrosive property.
The next object of the invention is to provide organic acids as one of the additives in the feed in such form which get hydrolvsed back to organic acids in the animal

gut without consuming the hydrochloric acid that is generated insitu in the animal gut
The object of the invention is to provide a novel urea amide derivative used as an acidifier of an animal feed.
The next object of the invention is to provide a process for the preparation of novel urea amide derivates.
According to present invention urea is converted to amide or diamide.triarnide or tetra amide and further optionally comprises an additional nutritionally relevant anion radical(s) bonded through dative bondsr thereby reducing ensuring its main role of maintaining the required acidic pH in the animal gut.
Accordingly the present invention relates to a novel urea amide derivative of formula I

Wherein a.-&-a' b and b' may independently define hydrogen or a lower alkyl group comprising 4-4 1-10 carbon atomsi or R-CO groups wherein^ b & b' may independently define hydrogen or R CO- groups R is a unsubstituted straight or branched alkyl group comprising 1-10 carbon atoms and optionally containing substituents like halogen, oxygen, sulphur, nitrogen etc.. with the proviso that atleast one of the a. a', b and b'%1 is R-CO- group wherein R defines defined-«* alkyl group as above containing contains 1-10 carbon atoms and preferably 1-8 carbon atoms; wherein M1 M+ & M'+ is optionally present in the molecule and M-

M & M' independently defines an ion capable of accepting a lone pair of electrons donated by Nitrogens of Urea molecule; wherein 'X' defines the negatively charged molecular ion; wherein 'p' denotes the total negative charge to neutralize the total positive charge present in the complex ion shown in parenthesis, and wherein the 'z' defines an integer 0 3 preferably 0-2 ;or a 'z' required to neutralize tho total positive charge present in the oomplox ion shown in paranthesis Wherein ' Y' is defined as a divalent element, preferably oxygen or sulphur most preferably oxygen.
According to the present invention the urea amide is formed from the acids like formic acid, acetic acid, propionic acid, butyric acid, pentanoic acid, hexanoic acid, heptanoic acid and-'octanoic acid and substituted compounds thereof like methionine hydroxy analog.
According to present invention the M+ and M,+, the nutritionally relevant anion radicals, is/are selected from the Acetic acid, Ascorbic acid, Biotin, Butyric acid, Citric acid, Folic acid, Formic acid, Fumaric acid, Gluconic acid, Glucoheptanoic acid, Hexanoic acid, Heptanoic acid, Lactic acid, Malic acid, Nicotinic acid, Octanoic acid, Pentanoic acid, Propionic acid, Phosphoric acid, Retinoic acid, Selenious acid and-aTartaric acid and substituted compounds thereof like methionine hydroxy analog.
Accordingly the present invention also relates to a process of preparation of a novel urea amide derivative of formula 1 comprising the steps of
a. adding urea and the organic acids as herein described in 1:1 or 1:2 to 1:4
molecular ratios
b. allowing the reaction mixture of step "a" to react and form the amide in a
known manner
c. optionally adding the nutritionally relevant anion radicals such as described
herein and allowing to stand and form the desire compounds related to
formula 1
d. isolating the desired compound from the reaction mixture in a known
manner
The novel urea amide derivative of the present invention combines the benefits of providing the required acidic pH of organic acids in the animal's stomach and less corrosiveness. When the nutritionally relevant anion radicals are devoided in the formula 1 then the derivates can be manufactured in a powder solid form which can be handled easily. When the derivative of formula 1 comprises the nutritionally relevant anion radicals the compounds generally are in liquid form.

The compounds of the present invention are found to be hydrolysable in the presence of acid as a catalyst or base as a catalyst. This property is the key factor for the acid hydrolysis inside an animal gut as hydrochloric acid generated insitu is not consumed unlike when the salt form of the organic acids are used as explained earlier.
The compounds of the present invention can be used as growth promoters, preservatives, anti-bacterial agents, anti-microbial agents and acidifiers in the animal feed.
The description of the present invention should not be construed as to limit the invention and the changes that can be made by a person skilled in the art should be treated as included in the description.




CLAIMS
I claim
1. The compound of the formula 1

Wherein a.-&-a' b and b' may independently define hydrogen or a lower alkyl group comprising_1-4J1-10 carbon atomsr or R-CO groups wherein, b & b' may independently define hydrogen or R CO groups R is a unsubstituted straight or branched alkyl group comprising 1-10 carbon atoms and optionally containing substituents like halogen, oxygen, sulphur nitrogen etc., with the proviso that atleast one of the a. a', b and b' is R-CO- group wherein R defines defined-an alkyl group as above containing contains 1-10 carbon atoms and preferably 1-8 carbon atoms; wherein M',M+ & M'+ is optionally present in the molecule and M' M+& M'+ independently defines an ion capable of accepting a lone pair of electrons donated by Nitrogens of Urea molecule; wherein 'X' defines the negatively charged molecular ion; wherein 'p' denotes the total negative charge to neutralize the total positive charge present in the complex ion shown in parenthesis, and wherein the V defines an integer 0-3 preferably 0-2

required to neutralize the total positive charge present in the complex ion shown in paranthesis Wherein 'Y' is defined as a divalent element preferably oxygen or sulphur most preferably oxygen,
2. The compound as claimed in claim 1 wherein the formula 1 is devoid of the nutritionally relevant anion radical(s).
3. The compound as claimed in claim 1 wherein the nutritionally relevant acid radicals are bonded to the nitrogen(s) of urea and/or its derivative.
4. The process for the preparation of novel urea amide derivative as claimed in claim 1 comprising the steps of

a) Adding urea and the organic acids herein described in 1:1 or 1:2 to 1:4 molecular rates.
b) Allowing the mixed step 'a' to react and form the amide(s} in a known molecule manner.
c) Optionally adding the nutritionally relevant anion radicals such as described herein and allowing to stand and form the desire compounds related to formula 1.
d) Isolating the desired compound from the reaction mixture in a known manner.

5. The process as claimed in claim 4 wherein the amides are prepared by reacting the urea with the acids such as formic acid, acetic acid, propionic acid, butyric acid, pentanoic acid, hexanoic acid, heptanoic acida-and-pctanoic acid and substituted compounds thereof like methionine hydroxy analog.
6. The process as claimed in claim 4 wherein the nutritionally relevant acid radicals is selected from acids such as Acetic acid, Ascorbic acid, Biotin, Butyric acid, Citric acid, Folic acid, Formic acid, Fumaric acid, Gluconic acid, Glucoheptanoic acid, Hexanoic acid, Heptanoic acid, Lactic acid, Malic acid, Nicotinic acid, Octanoic acid, Pentanoic acid, Propionic acid, Phosphoric acid, Retinoic acid, Selenious acid-and, Tartaric acid and substituted compounds thereof like methionine hydroxy analog.
7. Use of the novel urea amide derivative as growth promoters, acidifiers, preservatives, anti-microbial agents and anti-bacterial agents in the animal nutrition field.
8. Use of novel urea amide(s) in powder solid forms to easen use in handling & reduce corrosion of equipments.
9. An invention as herein above described.

Documents:

0691-che-2005 abstract granted.pdf

0691-che-2005 claims granted.pdf

0691-che-2005 description (complete) granted.pdf

0691-che-2005-abstract.pdf

0691-che-2005-claims.pdf

0691-che-2005-correspondnece-others.pdf

0691-che-2005-correspondnece-po.pdf

0691-che-2005-description(complete).pdf

0691-che-2005-form 1.pdf

0691-che-2005-form 9.pdf

691-che-2005-form 1.pdf


Patent Number 224868
Indian Patent Application Number 691/CHE/2005
PG Journal Number 49/2008
Publication Date 05-Dec-2008
Grant Date 23-Oct-2008
Date of Filing 06-Jun-2005
Name of Patentee KRISHNAN RAMU
Applicant Address 6-G, CENTURY PLAZA, 560-562 ANNA SALAI, TEYNAMPET, CHENNAI 600 018,
Inventors:
# Inventor's Name Inventor's Address
1 KRISHNAN RAMU 6-G, CENTURY PLAZA, 560-562 ANNA SALAI, TEYNAMPET, CHENNAI 600 018,
PCT International Classification Number C07C 273/00
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA