Title of Invention

A NOVEL SYNTHETIC PLANT GROWTH REGULATOR COMPOUND, METHANONE-(3,4,5-TRIMETHOXY) PHENYL, 1-NAPHTHYL, 2-O-4-ETHYL BUT-2-ENOATE

Abstract

This invention provides a novel synthetic plant growth regulatory compound Methanone- (3', 4', 5'-trimethoxy) phenyl, 1-naphthyl, 2-O-4"-ethyl but-2"-enoate. More particularly, the invention relates to the potent plant growth promoting activity of a gallic acid derivative and molecular formulae C26H26O7. This invention also provides a novel process for preparation of a said molecule from a naturally occurring compound and testing it for growth regulating activity using Bacopa test system.

Full Text

A NOVEL SYNTHETIC PLANT GROWTH REGULATOR COMPOUND, METHANONE- (3,4,5 -TRIMETHOXY) PHENYL, 1-NAPHTHYL, 2-O-4 -ETHYL BUT-2 -ENOATE TECHNICAL FIELD This invention provides a novel synthetic plant growth regulator compound Methanone- (3', 4', 5'-trimethoxy) phenyl, 1-naphthyl, 2-0-4"-ethyl but-2"-enoate. More particularly, the invention relates to the potent plant growth promoting activity of a gallic acid derivative having the structural formulae 1 and molecular formulae C26H26O7. This invention also provides a novel process for preparation of a said molecule from a naturally occurring compound and testing it for growth regulating activity using Bacopa test system developed at CIMAP (Khanuja et al 2001). (Formula Removed) BACKGROUND AND PRIOR ARTS Plant growth substances occupy an important place in the growth and developmental processes of all plant species. The pioneers in plant growth substances, Charles Darwin, Boycen-Jensen, and others, recognized that plant growth phenomenon was under control of some chemical substances produced by the plants and in 1928 F. W. Went successfully demonstrated the existence of growth-regulating substances in plants. These compounds are useful for altering a plant's life processes or structure in some beneficial way so as to enhance yield, improve quality or facilitate harvesting. The plant growth hormones, auxins from oat seedlings, and gibberellins from a fungus, and several secondary plant products such as phenolics, lipids, steroids and terpenoids were shown to be responsible for plant growth and development. One class of plant hormone, auxins, and their synthetic mimics are of particular interest. Auxinlike activity is known to affect a number of plant processes, such as cell division, rooting at the basal end of shoots, shoot elongation, apical dominance, phototropic responses and control of abscission of organs such as buds, flowers, fruits, leaves and This invention provides a novel biologically active synthetic compound, Methanone- (3,4,5-trimethoxy) phenyl, 1-naphthyl, 2-O-4 "-ethyl but-2-enoate. More particularly, the invention relates to the development of a new synthetic molecule with potent plant growth regulator activity having the structural formulae 1.This invention also provides a process for preparation of the said molecule from a naturally occurring compound. The molecule in question is a light yellow oil, having molecular formulae C26H26O7 Further the invention provides plant growth promoting activity of a gallic acid derivative using a plant biosensor system 'Bacopa test'. This invention also provides efficient and economical process for the production of the said molecule. OBJECTS OF THE INVENTION The main object of the present invention is to provides a novel gallic acid derivative, Methanone- (3',4',5'-trimethoxy) phenyl, 1-naphthyl, 2-0-4"-ethyl but-2"-enoate, C26H26O7 having structural formula (1). One more object of the present invention provides a novel gallic acid derivative, Methanone- (3',4',5'-trimethoxy) phenyl, 1-naphthyl, 2-0-4"-ethyl but-2"-enoate, C26H26O7, represented by structural formulae (1), useful as a plant growth regulator. Another object of the present invention provides a novel gallic acid derivative, 2-0- naphthyl , 3 ,4,5 -Trimethoxy benzoate, having structural formula 4 and molecular formulae C20H18O5, and its usefulness as plant growth regulator in development of plants. Yet another object of the present invention provides a novel gallic acid derivative Methanone- (3 ,4,5 -Trimethoxy) phenyl, 1-naphthyl, 2-ol, having structural formula 5 and molecular formulae C17H18O5, capable of plant growth regulation compound, obtained during synthesis of compound 1 Still another object of the present invention provides an efficient and economical process for the preparation of this biologically active compound represented by structural formula (1) with higher yields from a readily available starting material. DETAILED DESCRIPTION OF THE INVENTION Accordingly, the present invention relates to a novel synthetic plant growth regulator compound, Methanone- (3 ,4,5-Trimethoxy) phenyl, 1-naphthyl, 2-0-4-ethyl but-2 -enoate having structural formula 1 and having molecular formulae C26H26O7, (Formula Removed) and a process for the preparing the above said compound comprises: (a) methylating gallic acid by treating it with a methylating agent and alkali in a suitable solvent in the range of in the reaction medium to obtain intermediate having a structural formula formula 3 i.e 3,4,5-trimethoxy benzoic acid, (b) reacting 3,4,5-Trimethoxy Benzoic acid obtained in step (a) with 2-naphthol in presence of carboxylic acid activator in presence of suitable base and an organic solvent ml to obtain an intermediate compound having structural formula 4 and molecular formula C20H18O5, (c) purifying the compound having structural formula 4 obtained in the step (b) by column chromatography, (d) subjecting the compound having structural formula 4 of step (c) to Fries rearrangement in presence of appropriate lewis acid at a temperature in the range of about of 50-150°C and followed by purification by column chromatography to get an intermediate having a structural formula 5 and molecular formula C17H18O5 in the range of about 15-40 %, and (e) reacting intermediate having a structural formula 5 from step (d) with alkyl halo crotonate in a suitable reaction medium consisting of base and suitable organic solvent to get methanone- (3,4,5 -trimethoxy) phenyl, 1-naphthyl, 2-O-4-ethyl but-2"-enoate, having structural formula 1 and molecular formula C26H26O7 in the range of 45 to 75%. Another embodiment of the present invention relates a novel compound, Methanone- (3,4,5-Trimethoxy) phenyl, 1-naphthyl, 2-ol, having structural formula 5 and molecular formulae C17H18O5, capable of plant growth regulation compound, obtained during synthesis of compound 1, (Formula Removed) Still another embodiment of the present invention relates to the said compound having formula 1 wherein the compound having formula 1 has auxin like plant growth regulatory activity. Yet another embodiment of the present invention relates to the compound of formula 1 wherein the said compound enhances the shoot elongation by about 2 cm within 15 days. Another embodiment of the present invention relates to compound of formula 1 wherein the said compound enhances the shoot elongation by about 1.6 cm within 15 days One more embodiment of the present invention relates to compound of formula 1 wherein the said compound produces about 2 to 5 shoots within three weeks in medium A3. Still embodiment of the present invention relates to compound of formula 1 wherein the said compound produces about 3 to 4 shoots within three weeks in medium A3. Another embodiment of the present invention relates to compound of formula 1 wherein the said compound is more effective at low concentrations in enhancing the callus formation and shoot differentiation. Yet another embodiment of the present invention relates to a process for the preparing the compound having structural formula 1 i.e. Methanone- (3 ,4 ,5 -Trimethoxy) phenyl, 1 -naphthyl, 2-O-4"-ethyl but-2 -enoate and having molecular formulae C26H26O? said process comprising the steps of: (a) methylating gallic acid by treating it with a methylating agent and alkali in a suitable solvent in the reaction medium to obtain intermediate having a structural formula formula 3 i.e 3,4,5-trimethoxy benzoic acid, (b) reacting 3,4,5-Trimethoxy Benzoic acid obtained in step (a) with 2- naphthol in presence of carboxylic acid activator, a suitable base in and an organic solvent to obtain an intermediate compound having structural formula 4 and molecular formula CzoHigOs, (c) purifying the compound having structural formula 4 obtained in the step (b) by column chromatography, (d) subjecting the compound having structural formula 4 of step (c) to Fries rearrangement in presence of appropriate lewis acid at a temperature in the range of about of 50-150°C and followed by purification by column chromatography to get an intermediate having a structural formula 5 and molecular formula CnHigOs in the range of about 15-40 %, and (e) reacting intermediate having a structural formula 5 from step (d) with alkyl halo crotonate in a suitable reaction medium consisting of base and suitable organic solvent to get methanone- (3 ,4,5 -trimethoxy) phenyl, 1-naphthyl, 2- O-4 -ethyl but-2"-enoate, having structural formula 1 and molecular formula CjeHaeO? in the range of about 45 to 75%. Still another embodiment of the present invention relates to methylating agent in step (a) wherein the methylating agent is selected from the group comprising of dimethyl sulphate or methyl iodide. Yet another embodiment of the present invention relates to methylating agent wherein methylating agent used is dimethyl sulphate. One more embodiment of the present invention relates to methylating agent in step (a) wherein the methylating agent is in the range of about 20-30 ml. One more embodiment of the present invention relates to methylating agent in step (a) wherein the methylating agent is in the range of about 21-28 ml. Yet another embodiment of the present invention relates to alkali in step (a) wherein the alkali is selected from the group consisting sodium hydroxide, potassium hydroxide or lithium hydroxide. Another embodiment of the present invention relates to alkali wherein alkali used is sodium hydroxide or potassium hydroxide. Still another embodiment of the present invention relates to the alkali in step (a) wherein alkali is in the range of about 10-25 g. Still another embodiment of the present invention relates to the alkali in step (a) wherein alkali is in the range of about 16- 20 g. One more embodiment of the present invention relates to solvent of step (a) wherein solvent is selected from the group consisting of water, methanol and acetone. Yet another embodiment of the present invention relates to solvent wherein solvent used in the step is water. Another embodiment of the present invention relates to solvent in step (a) wherein solvent is in the range of about 50-120 ml. Another embodiment of the present invention relates to solvent in step (a) wherein solvent is in the range of about 60-100 ml. Still another embodiment of the present invention relates to the 2-naphthol in step (b) wherein 2-naphthol is in the range of about 2 to 5 g. Still another embodiment of the present invention relates to the 2-naphthol in step (b) wherein 2-naphthol is in the range of about 3.6 to 4 g. Yet another embodiment of the present invention relates to activator of step (b) wherein activator is selected from the group consisting of dicyclo hexy carboiimide (DCC) and N' (3- Dimethylaminopropyl)-N-ethyl carboiidmide hydrochloride (EDC). Still another embodiment of the present invention relates to activator wherein the activator used is DCC. One more embodiment of the present invention relates to activator in step (b) wherein the activator is in the range of about 2 to 5 g. One more embodiment of the present invention relates to activator in step (b) wherein the activator is in the range of about 3.6 to 4 g. Another embodiment of the present invention relates to base of step (b) wherein the base is selected from the group consisting Dimethyl amino pyridine (DMAP) or Triethyl amine(TEA). Yet another embodiment of the present invention relates to the base in step (b) wherein the base is in the range of about 25-60 g. Yet another embodiment of the present invention relates to the base in step (b) wherein the base is in the range of about 30-50 g. Still another embodiment of the present invention relates to organic solvent in step (b) wherein the organic solvent is selected from the group consisting dichloromethane or dimethyl formamide. One more embodiment of the present invention relates to organic solvent wherein organic solvent is dichloromethane. Another embodiment of the present invention relates to the organic solvent in step (b) wherein organic solvent is in the range of about 30-80 ml. Another embodiment of the present invention relates to the organic solvent in step (b) wherein organic solvent is in the range of about 40-70 ml. Still another embodiment of the present invention relates to column chromatography of steps (c) and (d) wherein column chromatography the adsorbent is selected from the group consisting silica gel, silicic acid or fluorosil. One more embodiment of the present invention relates the adsorbent whereinthe adsorbent used is silica gel. Another embodiment of the present invention relates to the temperature in step (d) wherein the temperature is in the range of about 60 to 130°C Yet another embodiment of the present invention relates lewis acid of step (d) wherein the lewis acid is selected from the group consisting aluminium chloride, zinc chloride or polyphosphoric acid. Another embodiment of the present invention relates lewis acid whereinthe lewis acid used is aluminium chloride. One more embodiment of the present invention relates lewis acid in step (d) wherein lewis acid is in the range of about 1-5 g. One more embodiment of the present invention relates lewis acid in step (d) wherein lewis acid is in the range of about 2-3 g. Still another embodiment of the present invention relates yield of Methanone-(3,4,5-Trimethoxy) phenyl, 1-naphthyl, 2-ol intermediate having a structural formula 5 and molecular formula C17H18O5 in step (d) wherein the yield of said compound is in the range of about 20-31.2 %. One more embodiment of the present invention relates alkyl halo crotonate in step (e) wherein the alkyl halo crotonate is selected from the group consisting methyl chloro crotonate, methyl bromo crotonate or ethyl bromo crotonate. Still another embodiment of the present invention relates alkyl halo crotonate wherein alkyl halo crotonate is ethyl bromo crotonate. Another embodiment of the present invention relates alkyl halo crotonate in step (e) wherein the alkyl halo crotonate is in the range of about 0.1 to 1.5 ml. Another embodiment of the present invention relates alkyl halo crotonate in step (e) wherein the alkyl halo crotonate is in the range of about 0.2 to 0.5 ml. One more embodiment of the present invention relates base in step (e) wherein the base is selected from the group consisting potassium hydroxide, sodium hydroxide or potassium carbonate. Still another embodiment of the present invention relates to the base wherein the base used is potassium carbonate. Yet another embodiment of the present invention relates base in step (e) wherein the base is in the range of about 0.5 to 3 g. Yet another embodiment of the present invention relates base in step (e) wherein the base is in the range of about 1 to 2 g. Another embodiment of the present invention relates to the organic solvent in step (e) wherein the organic solvent is selected from the group consisting dimethyl formamide, acetone or methanol. One more embodiment of the present invention relates to the organic solvent wherein the organics solvent used is acetone. Still another embodiment of the present invention relates organic solvent in step (e) wherein organic solvent is in the range of about 5 to 15 ml. Still another embodiment of the present invention relates organic solvent in step (e) wherein organic solvent is in the range of about 6 to 10 ml. One more embodiment of the present invention relates to the yield of methanone- (3 ,4,5 -trimethoxy) phenyl, 1 -naphthyl, 2-O-4 -ethyl but-2 -enoate, having structural formula 1 and molecular formula CaetbeO? in step (e) wherein the yield of the said compound is in the range of about 47 to 70%. The invention is described in detail in the examples given below which are provided to illustrate the invention and therefore should not be construed to limit the scope of the invention. EXAMPLES Example -1: Growth promoting activity of compound 1 using Bacopa sensor system For testing the growth promoting effect of Methanone- (3',4',5'-trimethoxy) phenyl, 1-naphthyl, 2-O-4"-ethyl but-2"-enoate, the compounds was dissolved in DMSO and added into the medium at 1.0 g/ml. Only solvent was used as control in the experiment for comparison. A fast propagating strain of Bacopa monnieri developed as a biosensor system through tissue culture at CIMAP (Khanuja et al 2001, J Environa Pathol, Toxicol and Onco (JEPTO,), 20:15-22) was used in the tests. The MS basal medium (Murashige and Skoog, 1962, Physiol.olanta 15: 473 - 497) supplemented with test compounds was used in the assays. Measured 0.5 to 1.0 ml medium was poured into 1.5 ml graduated microcentrifuge tubes. Twig cuttings of 2.5 cm were inoculated in 10 replicates for each treatment. These inoculated tubes were put into a half transparent dessicator allowing air passage through sterile cotton plugs fixed on opening vent. The tubes were placed such that the medium-containing portion of the tubes where roots would be initiating is inserted in to the holes of the stand made from a thermocol sheet. These dessicators were incubated at normal ambient temperature of 25-28°C with 14 hours light and 10 hours dark cycle. The root initiation, shoot elongation, callus induction, shoot proliferation and wilting was recorded from day 2 to 14 every 24 hours. Table 1: Growth promoting activity of Methanone- (3',4',5'-trimethoxy) phenyl, 1- naphthyl, 2-O-4"-ethyl but-2"-enoate using Bacopa sensor system. (Table Removed) Example -2: Growth promoting activity of compound 1 using aromatic plant species Mentha arvensis To confirm the growth promoting activity of Methanone- (3',4',5'-trimethoxy) phenyl, 1- naphthyl, 2-O-4"-ethyl but-2"-enoate, it was tested with a medicinal and aromatic plant species Mentha arvensis. The explants used were 0.5 cm long pieces of the second and third internodes of the shoots formed from axillary buds and culture. The internode segments were inoculated in MS basal media (Murashige and Skoog, 1962, Physiol.olanta 15: 473 - 497) containing vitamins lOOμg/ml, myo-inositol 3%, w/v, sucrose 1.5% w/v, Agar and different concentrations of auxins and cytokinin. Different concentrations of 1- naphthalene acetic acid (NAA) (0.0, 0.2, 2.0 ng/ml) were used in combination with different concentrations of 6 benzyl amino purine (BAP) (0, 10 & 5 μg/ml). On each kind of media 10 replicates of the explants were inoculated into three petriplates with each plates containing 4 explants. The compound 1 was serially replaced with each concentration of NAA and BAP individually to observe its growth promoting activity. The experiment was arranged in the form of a completely randomized design (CRD). Cultures were maintained at 25 ± 2° C and 400 - 600 lux light intensity with 16 h photoperiod. The response of explants was recorded every 24 h over 4 weeks period. Each explant was observed at 2 weeks interval and sub cultured on same fresh medium. The proportional increase in biomass was recorded by taking the fresh weight of the growing tissue during sub culturing and dividing the increase with the initial weight. At the end of 12 weeks from inoculation the shoots were separated and individually transferred to MS basal media containing vitamins for rooting. The rooted plantlets were subsequently transferred to pods in a green house. Composition of Medium A3: The basal medium for studying the response was MS 0 (Murashige, T., Skoog, F. 1962, Physiol.planta. 15: 473-497) supplemented with 2mg/L IAA (Indole acetic acid) and 10 mg/L BAP (Benzene amino purine). Composition of Medium A2:1962, Phys\o\.p\anta. 15: 473-49 > s •ippfeni'fcrar with 0.2mg/L lAA (Indole acetic acid) and 5mg/L BAP (Benzene amino purine). Table 2: Growth promoting activity of Methanone- (3',4',5'-trimethoxy) phenyl, 1-naphthyl, 2-O-4"-ethyl but-2"-enoate with Mentha arvensis. (Table Removed) Example 3 Synthesis of the bioactive compound Methanone- (3',4',5'-trimethoxy) phenyl, 1- naphthyl, 2-O-4"-ethyl but-2"-enoate (a) Methylating gallic acid [Gallic acid is 3,4,5-trihydroxybenzoic acid , C 6 H 2 (OH) 3 CO 2 H, colorless, odorless, crystalline organic acid found in gallnuts, sumach, tea leaves, oak bark, and many other plants, both in its free state and as part of the tannin molecule (Gallotannin). (Columbia) Encyclopedia, Sixth Edition, Copyright (c) 2003). There are reports on several derivatives of gallic acid having different pharmaceutical activities] by treating it with a methylating agent and alkali in a suitable organic solvent reaction medium to 3,4,5-trimethoxy benzoic acid; (b) Reacting 3,4,5-trimethoxy benzoic acid with 2-naphthol in presence of carboxylic acid activator, suitable base in an appropriate organic solvent medium to condensed product purifying the product through suitable column chromatography; (c) Subjecting the condensed product to Fries rearrangement in presence of appropriate lewis acid at a temperature of 60-130°C and followed by purification by suitable column chromatography of phenolic naphthophenone derivative and finally; (d) Treating the phenolic naphthophenone derivative by alkyl halo crotonate in a suitable reaction medium consisting of base and suitable organic solvent to get methanone- (3 ,4 ,5 -trimethoxy) phenyl, 1-naphthyl, 2-O-4 - ethyl but-2"-enoate. (e) The methylating agent used in step (a) can be dimethyl sulphate and methyl iodide. (f) The alkali used in step (a) is selected from a group consisting of sodium hydroxide, potassium hydroxide and lithium hydroxide. (g) The organic solvent used in step (a) is selected from a group consisting of water, methanol and acetone. (h) The methylating agent in step (a) is in the range of about 21-28 ml. (i) The alkali in step (a) is in the range of about 16- 20 g. (j) The 2-naphthol is in the range of about 3.6 to 4g. (k) The solvent in step (a) is in the range of about 60-100 ml. (1) The activator in step (b) is in the range of about 3.6 to 4 g. (m) The base in step (b) is in the range of about 30-50 g. (n) The organic solvent in step (b) is in the range of about 40-70 ml. (o) The carboxylic acid activator used in step (b) is selected from a group consisting of DCC and EDC. (p) The base used in used in step (b) with carboxylic acid activator is selected from a group consisting of DMAP and TEA. (q) The organic solvent used in step (b) is selected from a group consisting of dichloromethane, dimethyl formamide. (r) The column chromatography adsorbent used in step (b) is selected from a group consisting of silica gel, silicic acid and fluorosil. (s) The lewis acid used in step (c) is selected from a group consisting of aluminium chloride, zinc chloride and polyphosphoric acid, (t) The column chromatography adsorbent used in step (c) is selected from a group consisting of silica gel, silicic acid and fluorosil. (u) The lewis acid in step (d) is in the range of about 2-3 g. (v) The alkyl halo crotonate used in the step (d) to etherify the phenolic naphthophenone is selected from the group consisting of methyl chloro crotonate, methyl bromo crotonate and ethyl bromo crotonate. (w) The base used in the etherification reaction in step (d) is selected from the group consisting of potassium hydroxide, sodium hydroxide and potassium carbonate. (x) The organic solvent used in the reaction (d) is selected from the group consisting of dimethyl formamide, acetone and methanol. (y) The alkyl halo crotonate in step (e) is in the range of about 0.2 to 0.5 ml. (z) The base in step (d) is in the range of about 1 to 2 g and organic solvent in step (d) is in the range of about 6 to 10 ml. The products of the reactions as described in the steps (a) to (d) herein below is represented hereunder; (Formula Removed) C10H12O5 (3,4,5-Trimethoxy benzoic acid, 3) (Formula Removed) C20H18O5 [ 2-O-naphthyl, 3 ,4,5 -Trimethoxy benzoate, 4] (Formula Removed) [ Methanone- (3 ,4,5 -Trimethoxy) phenyl, 1-naphthyl, 2-ol, 5] (Formula Removed) C26H26O7 [Methanone- (3 ,4,5 -Trimethoxy) phenyl, 1-naphthyl, 2-O-4"-ethyl but-2" enoate, 1]. We claim : 1. A novel synthetic plant growth regulator compound, Methanone-(3,4,5-Trimethoxy) phenyl, 1-naphthyl, 2-O-4"-ethyl but-2"-enoate having structural formula 1 and having molecular formulae C26H26O7, (Formula Removed) 2. A process for the preparation of compound of formula 1 of claim 1 comprises: (a) methylating gallic acid by treating it with a methylating agent and alkali in a suitable solvent in the range of in the reaction medium to obtain intermediate having a structural formula formula 3 i.e. 3, 4, 5- trimethoxy benzoic acid, (Formula Removed) (b) reacting 3, 4, 5-trimethoxy benzoic acid obtained in step (a) with 2- naththol in presence of carboxylic acid activator in presence of suitable base and an organic solvent ml to obtain an intermediate compound having structural formula 4 and molecular formula C20H18O5 (Formula Removed) (c) purifying the compound having structural formula 4 obtained in the step (b) by column chromatography, (d) subjecting the compound having structural formula 4 of step (c) to Fries rearrangement in presence of appropriate selected at a temperature in the range of about of 50-150°C and followed by purification by column chromatography to get an intermediate having a structural formula 5 and. molecular formula C17H18O5 in the range of about 15-40%, and (Formula Removed) (e) reacting intermediate having a structural formula 5 from step (d) with alkyl halo crotonate in a suitable reaction medium consisting of base and suitable organic solvent to get methanone - (3,4,5- trimethoxy) phenyl, 1-naphthyl, 2-O-4"-ethyl but-2"-enoate, having structural formula 1 and molecular formula C26H26O7 in the range of 45 to 75% . 3. A method as claimed in claim 2, wherein methylating agent in step (a) is selected from the group comprising of dimethyl sulphate or methyl iodide. 4. A method as claimed in claim 3, wherein methylating agent used is preferably dimethyl sulphate. 5. A method as claimed in claim 2, wherein methylating agent in step (a) is in the range of 20-30 ml. 6. A method as claimed in claim 5, wherein methylating agent in step (a) is preferably in the range of 21-28 ml. 7. A method as claimed in claim 2, wherein alkali in step (a) is selected from the group consisting sodium hydroxide, potassium hydroxide or lithium hydroxide. 8. A method as claimed in claim 7, wherein alkali used is preferably sodium hydroxide or potassium huydroxide. 9. A method as claimed in claim 1, wherein alkali in step (a) is in the range of 10-25g. 10. A method as claimed in claim 9, wherein alkali in step (a) is preferably in the range of 16-20g. 11.A method as claimed in claim 2, wherein solvent of step (a) is selected from the group consisting of water, methanol and acetone. 12.A method as claimed in claim 11, wherein solvent used is preferably water. 13. A method as claimed in claim 2, wherein solvent in step (a) is in the range of about 50-120 ml. 14. A method as claimed in claim 13, wherein solvent in the step (a) is preferably in the range of about 60-100ml. 15.A method as claimed in claim 2, wherein 2-naphthol is in the range of 2 to 5g- 16. A method as claimed in claim 15, wherein 2-naphtho) is preferably in the range 3.6 to 4g. 17. A method as claimed in claim 2, wherein activator of step (b) is sleeted from the group consisting of dicyclo hexy carboiidmide hydrochloride (EDC). 18.A method as claimed in claim 17, wherein activator used is preferably DCC. 19. A method as claimed in claim 2, wherein the activator in step (b) is in the range of 2 to 5g. 20. A method as claimed in claim 19, wherein the activator in step (b) is preferably in the range of 3.6 to 4g. 21. A method as claimed in claim 2, wherein base of step (b) is selected from the group consisting dimethyl amino pyridine (DMAP) and triethyl amine (TEA). 22. A method as claimed in claim 2, wherein the base in step (b) in the range of 25-60g. 23. A method as claimed in claim 22, wherein the base in step (b) is preferably in the range of 30-50g. 24. A method as claimed in claim 23, wherein organic solvent in step (b) is selected from the group consisting dichloromethane or dimethyl formamide. 25. A method as claimed in claim 24, wherein organic solvent is preperably dichloromethane. 26. A method as claimed in claim 2, wherein the organic solvent in step (b) is in the range of 30-80 ml. 27. A method as claimed in claim 26, wherein the organic solvent in step (b) is preferably in the range of 40-70ml. 28. A method as claimed in claim 2, wherein column chromatography of step ( ( c )and (d) the adsorbent is selected from the group consisting silica gel, silicic acid or fluorosil. 29. A method as claimed in claim 28, wherein the adsorbent used is preferably silica gel. 30.A method as claimed in claim 2, wherein the temperature in step (d) is preferably in the range of 60 to 130°C. 31. A method as claimed in claim 2, wherein lewis acid of step (d) is selected from the group consisting aluminium chloride, zinc chloride or polyphosphoric acid. 32 A method as claimed in claim 31, wherein the lewis acid used is preferably aluminium chloride. 33. A method as claimed in claim 2, wherein lewis acid in step (d) is in the range of 1-5 g. 34. A method as claimed in claim 33, wherein lewis acid in step (d) is preferably in the range of 2-3g. 35. A method as claimed in claim 2, wherein alkyl halo crotonate in step (e) is selected from the group consisting methyl chloro crotonate, methyl bromo crotonate or ethyl bromo crotonate. 36. A method as claimed in claim 35, wherein alkyl halo crotonate is preferably ethyl bromo crotonate. 37. A method as claimed in claim 2, wherein alkyl halo crotonate in step (e) is in the range of 0.1 to 1.5 ml. 38. A method as claimed in claim 37, wherein alkyl hao crotonate in step (e) is preferably in the range of 0.2 to 0.5 ml. 39. A method as claimed in claim 1, wherein base in step (e) is selected from the group consisting potassium hydroxide, sodium hydroxide or potassium carbonate. 40. A method as claimed in claim 39, wherein base used is preferably potassium carbonate. 41. A method as claimed in claim 2, wherein base in step (e) is in the range of 0.5 to 3g. 42. A method as claimed in claim 41, wherein base in step (e) is preferably in the range of 1 to 2 g. 43. A method as claimed in claim 1, wherein organic solvent in step (e) is selected from the group consisting dimethyl formamide, acetone or methanol. 44. A method as claimed in claim 43, wherein organic solvent used is preferably acetone. 45. A method as claimed in claim 2, wherein organic solvent in step (e) is in the range of 5 to 15 ml. 46. A method as claimed in claim 45, wherein organic solvent in step (e) is preferably in the range of 6 to 10 ml.

Documents:

504-DELNP-2004-Abstract-(17-03-2010).pdf

504-delnp-2004-abstract.pdf

504-delnp-2004-Claims-(02-08-2011).pdf

504-DELNP-2004-Claims-(17-03-2010).pdf

504-delnp-2004-claims.pdf

504-delnp-2004-Correspondence Others-(02-08-2011).pdf

504-DELNP-2004-Correspondence-Others-(17-03-2010).pdf

504-delnp-2004-correspondence-others.pdf

504-DELNP-2004-Description (Complete)-(17-03-2010).pdf

504-delnp-2004-description (complete).pdf

504-DELNP-2004-Form-1-(17-03-2010).pdf

504-delnp-2004-form-1.pdf

504-delnp-2004-form-18.pdf

504-DELNP-2004-Form-2-(17-03-2010).pdf

504-delnp-2004-form-2.pdf

504-DELNP-2004-Form-3-(17-03-2010).pdf

504-delnp-2004-form-3.pdf

504-delnp-2004-form-5.pdf

504-DELNP-2004-Petition 137-(17-03-2010).pdf

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