Title of Invention

AN IMPROVED PROCESS FOR PREPARING RIMONABANT HYDROCHLORIDE

Abstract Disclosed in the present invention is an improved process for preparing 5-(4-chlorophenyl)-l- (2,4-dichlorophenyl)-4-methyl-N-(piperidin-l-yl) pyrazole-3-carboxamide, namely Rimonabant of formula 1 and pharmaceutical compositions containing the same.
Full Text FORM 2
THE PATENTS ACT, 19
(39 of 1970)
&
The Patent Rules, 2003

COMPLETE SPECIFICATION
(See section 10 and rule 13)

TITLE OF THE INVENTION
"AN IMPROVED PROCESS FOR PREPARING RIMONABANT"
We, CADILA HEALTHCARE LTD., a company incorporated under the Companies Act, 1956, of Zydus Tower, Satellite Cross Roads, Ahmedabad - 380 015, Gujarat, India.
The following specification particularly describes the nature of the invention and the manner
In which it is to he performed:-

ZRC-PD-022
FIELD OF INVENTION
The present invention relates to an improved process for preparing 5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-l-yl) pyrazole-3-carboxamide, namely Rimonabant of formula 1 and pharmaceutical compositions containing the same. BACKGROUND ART
This invention relates to an improved process for the preparation of 5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-l-yl) pyrazole-3-carboxamide, namely Rimonabant of formula 1.

1
Obese patients are at higher risk for coronary artery disease, hypertension, hyperlipidemia, and diabetes mellitus, among other diseases and thus their risk of morbidity and mortality increases. Due to many complex pathophysiological components which lead to obesity, the disease remains a challenging and significant clinical problem. Cannabinoides acting via cannabinoid receptors stimulate food intake and a particularly attractive antiobesity target is the cannabinoid CB1 receptor, which has also been shown to play a role in reinforcing reward. (LA. Sorbera et al., Drugs of Future 2005; 30(2): 128-137). Rimonabant in the form of its hydrochloride salt is a promising CB1 receptor antagonist that has shown to inhibit motivational and consummatory aspects of feeding, as well as alcohol and nicotine intake in animal models. Rimonabant has recently received its first approval in UK for the treatment of obesity. The agent also exhibited efficacy in phase III clinical trials and hold promise in the treatment of smoking cessation.
Rimonabant hydrochloride has been disclosed in EP 0576357, EP 0656354, EP 0658546, US 5624941 and US 5462960. The processes disclosed for the preparation of Rimonabant hydrochloride in these applications comprises Claisen condensation of 4-chloropropiophenone 2 with diethyl oxalate in the presence of lithium hexamethyl disilazide to give 4-(4-chlorophenyl)-3 methyl-2,4-dioxybutyric acid ethyl ester lithium salt 3. Condensation of compound 3 with 2,4-dichlorophenyl hydrazine 4 in refluxing ethanol
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affords corresponding hydrazone 5, which is further cyclised to pyrazole 6 in refluxing AcOH. Hydrolysis of the ethyl ester 6 with KOH in refluxing H2O/MeOH yields carboxylic acid 7, which is then activated as acid chloride 8 by treatment with thionyl chloride. The acid chloride 8 is reacted with 1-aminopiperidine 9 in the presence of triethyl amine in CH2CI2 to obtain the final compound, Rimonabant I. Rimonabant may be further treated with HC1 in ethyl ether to form its hydrochloride salt.
Following is the synthetic scheme depicting the above mentioned process (scheme 1):
Scheme 1











However, this process involves certain technical difficulties. Use of somewhat expensive lithium hexamethyl disilazide in the reaction process poses risk in handling,
3

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thereby leading to safety as well as reproducibility problems for producing intermediate compound 5. While refluxing compound 5 in acetic acid to obtain 6, the reaction tends to remain incomplete even after 24 hours of refluxing, thereby leading to cumbersome and a less viable process for commercial use. Also, in this process, the overall time to prepare cyclic ester compound 6 from 4-chloropropiophenone 2 takes almost 20 to 24 hours.
Thus, there is still a need for an improved process which is commercially viable and cost effective as well as environmental friendly giving reproducible and better yields.
Therefore, we directed our research work to develop a process for the preparation of the said compound of formula 1. with the objective of developing an efficient, economical and commercially more viable process employing cheaper and easily available raw materials, involving simple reaction steps and mild reaction conditions.
The present invention discloses an improved process for preparING of Rimonabant 1. EMBODIMENT(S) OF THE INVENTION:
In one aspect, the present invention provides an improved process to prepare 5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-l-yl)pyrazole-3-carboxamide, namely Rimonabant 1_.
In another embodiment of the invention describes a process, which overcomes some of the above stated disadvantages in the prior art.
A further embodiment of the present invention is directed towards pharmaceutical compositions and dosage forms of Rimonabant hydrochloride prepared according to the process of present invention.
SUMMARY OF THE INVENTION:
The present invention describes an improved process for the preparation of 5-(4-chlorophenyl)-1 -(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1 -yl) pyrazole-3-carboxamide, namely Rimonabant of formula I.
The route of synthesis is disclosed in scheme 2:
4

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Scheme 2

COOEt
COOEt
COOEt
I
COOEt

DISCLOSURE OF THE INVENTION:
The present invention provides an improved process for the preparation of 5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-l-yl) pyrazole-3-carboxamide, namely Rimonabant of formula 1 comprising of the following steps:
Step 1:
Preparation of diketo ester (10)
4-chloropropiophenone 2 is reacted with diethyl oxalate in the presence of sodium ethoxide to form diketo ester compound 10 which is used in the next step. The reaction may
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be carried out in suitable solvents such as ethanol, methyl tertiary butyl ether and the like or
mixtures thereof. Temperature in the range of 20 to 60 °C may be used. Inert atmosphere may
be maintained using N2, Ar, He gas but not critical.
Step 2:
Preparation of cyclic ester compound (6):
This diketo ester compound 10 is then reacted with 4-chloro phenyl hydrazine hydrochloride 4 in solvent and HC1 in presence of IPA.HC1 solution to give cyclic ester 6. Suitable solvent may be selected from ethanol, ethanolic HC1, methanolic HC1, diisopropyl ether and the like or mixtures thereof. Temperature in the range of 78 to 80 °C to reflux may be used.
Step 3:
Preparation of acid (7):
The cyclic ester compound 6 is converted into cyclic acid compound 7 by hydrolyzing with an alkali and an alcohol. Alkali such as LiOH, NaOH, KOH, t-BuOH may be used. Suitable alcohol may be methanol, ethanol, propanol, isobutanol, isopropyl alcohol and the like or mixtures thereof. KOH/Methanol is a preferred combination. Temperature in the range of 80 to 85 °C to reflux may be used.
Step 4:
Preparation of acid chloride (8):
The cyclic acid compound 7 is reacted with thionyl chloride to give acid chloride 8 by techniques known in the art. Catalytic DMF helps the reaction. Solvent is not critical and essential. But when solvent is used, preferred solvents are benzene, toluene and the like or mixtures thereof.
Step 5:
Preparation of Rimonabant (1):
The acid chloride 8 formed is finally reacted with 1-amino piperidine 9 in presence of a suitable amine such as triethyl amine to give Rimonabant 1 by processes known in the art.
Rimonabant 1 so obtained may be further treated with etheral HC1 solution to give Rimonabant hydrochloride salt by processes known in the art, which may be further used in preparing pharmaceutical preparations.
The following non-limiting examples illustrate the inventor's improved process for the preparation of 5-(4-chlorophenyl)-l-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-l-yl)
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pyrazole-3-carboxamide, namely Rimonabant of formula 1. discussed in the invention and
should not be construed to limit the scope of the invention in any way.
EXAMPLE 1
Preparation of Diketo Ester Compound (10)
Na metal (7 g) was added to ethanol under nitrogen atmosphere at room temperature with stirring. The reaction mass was concentrated below 60 °C and cooled and to this was added 4-chloropropiophenone (25 g) in ethanol. The reaction mixture was cooled and to this diethyl oxalate (35 g) was added dropwise and the reaction mixture was stirred for at least an hour. The reaction mixture was poured into water containing sulfuric acid at room temperature and extracted with methyl tertiary butyl ether. The organic layer was separated and the aqueous layer was extracted with methyl tertiary butyl ether. The organic layers were mixed, washed with brine, separated and dried, filtered and concentrated under reduced pressure to obtain diketo ester compound 10, which was taken up in the next step. Preparation of Cyclic Ester compound (6)
Addition of diketoester compound 10 to ethanol was carried out under nitrogen atmosphere. The reaction mixture was cooled and to this was added 2,4-dichlorophenyl hydrazine hydrochloride salt (29 g) at 10-12 °C with stirring. To the suspension was added IPA.HC1 solution and heated to reflux temperature for at least 1 h. The reaction mixture was cooled and concentrated under reduced pressure to dryness. To the solid obtained was added water and ethyl acetate. The organic layer was separated and washed with brine, dried (Na2S04), filtered and dried under reduced pressure. The solid so obtained was purified by triturating with diisopropyl ether to get 24.5 g of 6. (yield = 40.3 %, purity by HPLC = 96.8 %).
EXAMPLE 2
Preparation of Diketo Ester Compound (10)
Na metal (1.5 g) was added to ethanol under nitrogen atmosphere at room temperature with stirring. The reaction mass was concentrated below 60 °C, cooled and to this was added 4-chloropropiophenone (5 g) in ethanol. The reaction mixture was cooled and to this diethyl oxalate (7 g) was added dropwise and the reaction mixture was stirred for at least an hour. The reaction mixture was poured into water containing sulfuric acid at room temperature and extracted with methyl tertiary butyl ether. The organic layer was separated and the aqueous layer was extracted with methyl tertiary butyl ether. The organic layers were mixed, washed
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with brine, separated and dried, filtered and concentrated under reduced pressure to obtain diketo ester compound 10 (8 g), which was taken up in the next step.
Preparation of Cyclic Ester compound (6)
Addition of diketoester compound IJ) (8 g) to ethanol was carried out under nitrogen atmosphere. The reaction mixture was cooled and to this was added 2,4-dichlorophenyl hydrazine hydrochloride salt (6 g) at 10-12 °C with stirring. To the suspension was added IPA.HC1 solution and heated to reflux temperature for at least 1 h. The reaction mixture was cooled and concentrated under reduced pressure to dryness. To the solid obtained was added water and ethyl acetate. The organic layer was separated and washed with brine, dried, filtered and dried under reduced pressure. The solid so obtained was purified by triturating with diisopropyl ether to get 3.5 g of 6. (yield = 28.8 %, purity by HPLC = 92 %). EXAMPLE 3
Preparation of Diketo Ester Compound (10)
Na metal (0.75 g) was added to ethanol under nitrogen atmosphere at room temperature with stirring. The reaction mass was concentrated below 60 °C, cooled and to this was added 4-chloropropiophenone (2.5 g) in ethanol. The reaction mixture was cooled and to this diethyl oxalate (3.5 g) was added dropwise and the mixture was stirred for at least an hour. The reaction mixture was poured into water containing sulfuric acid at room temperature and extracted with methyl tertiary butyl ether. The organic layer was separated and the aqueous layer was extracted with methyl tertiary butyl ether. The organic layers were mixed, washed with brine, separated and dried, filtered and concentrated under reduced pressure to obtain diketo ester compound 10 (4 g), which was taken up in the next step.
Preparation of Cyclic Ester compound (6)
Addition of diketoester compound 10 (4 g) to ethanol was carried out under nitrogen atmosphere. The reaction mixture was cooled and to this was added 2,4-dichlorophenyl hydrazine hydrochloride salt (3 g) at 10-12 °C with stirring. To the suspension was added IPA.HC1 solution and heated to reflux temperature for at least 1 h. The reaction mixture was cooled and concentrated under reduced pressure to dryness. To the solid obtained was added water and diisopropyl ether. The organic layer was separated and washed with brine, dried, filtered and dried under reduced pressure. The solid so obtained was purified by triturating with diisopropyl ether to get 3.2 g of 6. (yield = 50 %, purity by HPLC = 89.7 % ). EXAMPLE 4
Preparation of Diketo Ester Compound (10)
8

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Na metal (13.6 g) was added to ethanol under nitrogen atmosphere at room temperature with stirring. The reaction mass was concentrated below 60 °C, cooled and to this was added 4-chloropropiophenone (50 g) in ethanol. The reaction mixture was cooled and to this diethyl oxalate (70 g) was added dropwise and the mixture was stirred for at least an hour. The reaction mixture was poured into water containing acetic acid at room temperature and extracted with methyl tertiary butyl ether. The organic layer was separated and the aqueous layer was extracted with methyl tertiary butyl ether. The organic layers were mixed, washed with brine, separated and dried, filtered and concentrated under reduced pressure to obtain diketo ester compound 10_(86 g), which was taken up in the next step.
Preparation of Cyclic Ester compound (6)
Addition of diketoester compound 10 (86 g) to ethanol was carried out under nitrogen atmosphere. The reaction mixture was cooled and to this was added 2,4-dichlorophenyl hydrazine hydrochloride salt (63.3 g) at 10-12 °C with stirring. To the suspension was added IPA.HC1 solution and heated to reflux temperature for at least 1 h. The reaction mixture was cooled and concentrated under reduced pressure to dryness. To the solid obtained was added water and diisopropyl ether. The organic layer was separated and washed with brine, dried, filtered and dried under reduced pressure. The solid so obtained was purified by triturating with diisopropyl ether to get 48 g of 6. (yield = 39.5 %, purity by HPLC = 90.2 %). EXAMPLE 5
Preparation of Diketo Ester Compound (10)
Na metal (20.4 g) was added to ethanol under nitrogen atmosphere at room temperature with stirring. The reaction mass was concentrated below 60 °C, cooled and to this was added 4-chloropropiophenone (75 g) in ethanol. The reaction mixture was cooled and to this diethyl oxalate (105 g) was added dropwise and the mixture was stirred for at least an hour. The reaction mixture was poured into water containing acetic acid at room temperature and extracted with methyl tertiary butyl ether. The organic layer was separated and the aqueous layer was extracted with methyl tertiary butyl ether. The organic layers were mixed, washed with brine, separated and dried, filtered and concentrated under reduced pressure to obtain diketo ester compound 10 (120 g), which was taken up in the next step.
Preparation of Cyclic Ester compound (6)
Addition of diketoester compound 10 (119.4 g) to ethanol was carried out under nitrogen atmosphere. The reaction mixture was cooled and to this was added 2,4-dichlorophenyl hydrazine hydrochloride salt (94.9 g) at 10-12 °C with stirring. To the
9

ZRC-PD-022
suspension was added IPA.HC1 solution and heated to reflux temperature for at least 1 h. The reaction mixture was cooled and concentrated under reduced pressure to dryness. To the solid obtained was added water and diisopropyl ether. The organic layer was separated and washed with brine, dried, filtered and dried under reduced pressure. The solid so obtained was purified by triturating with diisopropyl ether to get 77 g of 6. (yield = 42.2 %, purity by HPLC = 93.2 %).
Compounds 7 to 1 as described in below examples were prepared according to general process described in EP 0656354 with suitable modifications and/ or alterations all of which are within the scope of persons skilled in the art.
EXAMPLE 6
Preparation of acid (7)
Cyclic ester compound 6 (30 g) prepared above was added to methanol, followed by KOH pellets in methanol. The solution was stirred and heated to reflux temperature for 2 h, cooled and to it was added 10 % HC1 solution at 5 to 10 °C up to pH ~1, stirred and the solid was filtered, washed with 10 % HC1 solution and dried. To the material was added acetone followed by charcoal. The mixture was stirred, filtered, washed with acetone, solvent was evaporated, and the solid was dried to obtain the acid 7.
EXAMPLE 7
Preparation of acid chloride (8)
The cyclic acid 7 (25 g) obtained above was added to toluene, followed by SOCl2 (31 g). The reaction mixture was stirred and refluxed for at least 3 hours. The mixture was cooled, solvent distilled off to obtain acid chloride 8 to be used in next step.
EXAMPLE 8
Preparation of Rimonabant hydrochloride (1)
Cyclic acid chloride compound 8 (26.2 g) dissolved in dichloromethane was added to a stirred and cooled mixture of triethyl amine (9.86 g) and 1-amino piperidine (9.83 g) in dichloromethane and was further reluxed for 3 hours. The reaction mixture was poured into water and stirred. The layers were separated and the aqueous layer was extracted with dichloromethane. The organic layer was washed with brine, dried over Na2S04, distilled to obtain Rimonabant 1 as crude solid.
To the crude solid obtained was added diethyl ether and the mixture cooled. To this was added ethereal HC1 solution and stirred. The solid obtained was filtered, washed with diethyl ether and dried to obtain hydrochloride salt of Rimonabant (30 g).
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(yield = 91 %, purity by HPLC = 96 %).
Rimonabant 1 as prepared according to the present invention can be formulated into suitable pharmaceutical ly acceptable formulations for e.g. tablets, capsules, granules and the like by combination with suitable excipients by processes, methods and amounts as are known. The improved process of the present invention has the following advantages:
• The present invention uses sodium ethoxide in place of lithium hexamethyldisilazide in the conversion of 2 to 10 that is more safe in handling during the step.
• It also reduces the number of steps, viz. conversion of 2 to 3 and then 5 to 6 as has been reported in the earlier processes, whereas in our process, we have directly converted 4-chloropropiophenone 2 to cyclic ester compound 6 without any need to isolate and characterize the intermediate.
• The improved process is scalable at plant level and so industrially applicable on account of use of safer solvents in the reaction process.
• High yield of the final product (91 % yield).
• Substantial reduction in time for converting 2 to 6 from about 20-24 hours as reported in prior art, to 8 hours as is described in the present invention, leads to reduction in the time required for the overall process.
• The improved process disclosed in the present invention has been found to be very cost effective on account of using less expensive chemicals (sodium ethoxide instead of lithium hexamethyl disiilazide) during the process and substantially reducing the overall time for the reaction process.
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We claim:
1. A process of:

for the preparation of Rimonabant of formula 1, comprising at least the steps





a) reacting 4-chloropropiophenone 2 with diethyl oxalate in presence of sodium ethoxide in suitable solvent (s) to form diketo ester 10, followed by reaction of 10 with 4-chlorophenyl hydrazine hydrochloride 4 in suitable solvent (s) and HC1 in suitable solvent(s) preferably IPA.HC1 solution to give cyclic ester 6.









b) converting cyclic ester compound 6 into cyclic acid compound 7 in presence of KOH/methanol.
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COOH
COOEt
KOH MeOH

c) reacting cyclic acid compound 7 with thionyl chloride to give acid chloride 8.



COOH
COCI
TOLUENE SOC12

d) reacting acid chloride 8 with 1-amino piperidine 9 in presence of triethyl amine to give Rimonabant 1.



COCI

N NH2
(9)
NEt3, CH2CI2

2. A process as claimed in claim 1 wherein the process of step (a) involving the conversion of 2 to 10 is carried out in the presence of suitable solvents selected from alcohols such as ethanol, ethers such as methyl tertiary butyl ether or mixtures thereof.
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3. A process as claimed in claim 1 wherein the process of step (a) involving the conversion of 10 to 6 is carried out in suitable solvents selected from ethanol, methanol, isopropyl alcohol, diisopropyl ether or mixtures thereof.
4. A process as claimed in claim 1 wherein the process of step (a) is carried out in the temperature range of 20 to 60 °C.
5. A process as claimed in claim 1 wherein the process of step (a) is carried out in an inert atmosphere, in the presence of inert gas selected from N2, Ar, He.
6. A process for the preparation of cyclic ester compound 6 as claimed in claim 1 which comprises of reacting 4-chloropropiophenone 2 with diethyl oxalate in presence of sodium ethoxide in suitable solvent (s) to form diketo ester 10, followed by reaction with 4-chlorophenyl hydrazine hydrochloride 4 in suitable solvent(s) and HC1 in suitable solvent (s) preferably IPA.HC1 solution to give cyclic ester 6.

COOEt
COOEt COOEt



COOEt
COOEt
NHNH2.HCI ,CI

CI (4)
ETHANOL/ IPA.HCI Soln. REFLUX

7. A process as claimed in claim 6 wherein the process involving the conversion of 2 to 10 is carried out in the presence of suitable solvents selected from alcohols such as ethanol, ethers such as methyl tertiary butyl ether or mixtures thereof.
8. A process as claimed in claim 6 wherein the process involving the conversion of 10 to 6 is carried out in the presence of suitable solvents selected from ethanol, methanol, isopropyl alcohol, diisopropyl ether or mixtures thereof.
9. A process as claimed in claim 6 wherein the process is carried out in the temperature range of 20 to 60°C.
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10. A process as claimed in claim 6 wherein the process is carried out in the presence of inert gas selected from N2, Ar, He.
11. A pharmaceutical composition comprising the compound of the formula/1 prepared according to the present invention.
Dated this the 18th day of August 2006
H.SUBRAMANIAM Of Subramaniam, Nataraj & Associates Attorneys for the Applicants
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Title:

An improved process for preparing Rimonabant

Abstract:
Disclosed in the present invention is an improved process for preparing 5-(4-chlorophenyl)-l-
(2,4-dichlorophenyl)-4-methyl-N-(piperidin-l-yl) pyrazole-3-carboxamide, namely
Rimonabant of formula 1 and pharmaceutical compositions containing the same.

16

Documents:

1014-MUM-2005-ABSTRACT(21-8-2006).pdf

1014-MUM-2005-ABSTRACT(GRANTED)-(16-12-2011).pdf

1014-mum-2005-abstract.doc

1014-MUM-2005-CANCELLED PAGES(29-8-2011).pdf

1014-MUM-2005-CLAIMS(21-8-2006).pdf

1014-MUM-2005-CLAIMS(AMENDED)-(23-3-2011).pdf

1014-MUM-2005-CLAIMS(AMENDED)-(29-8-2011).pdf

1014-MUM-2005-CLAIMS(GRANTED)-(16-12-2011).pdf

1014-mum-2005-claims.doc

1014-mum-2005-correspondance-received-ver-120805.pdf

1014-mum-2005-correspondance-received.pdf

1014-MUM-2005-CORRESPONDENCE(03-11-2010).pdf

1014-MUM-2005-CORRESPONDENCE(17-3-2010).pdf

1014-MUM-2005-CORRESPONDENCE(18-4-2012).pdf

1014-MUM-2005-CORRESPONDENCE(18-8-2006).pdf

1014-MUM-2005-CORRESPONDENCE(19-9-2011).pdf

1014-MUM-2005-CORRESPONDENCE(25-07-2008).pdf

1014-MUM-2005-CORRESPONDENCE(29-9-2011).pdf

1014-MUM-2005-CORRESPONDENCE(IPO)-(25-07-2008).pdf

1014-mum-2005-description (complete).pdf

1014-mum-2005-description (provisional).pdf

1014-MUM-2005-DESCRIPTION(COMPLETE)-(21-8-2006).pdf

1014-MUM-2005-DESCRIPTION(GRANTED)-(16-12-2011).pdf

1014-MUM-2005-DESCRIPTION(PROVISIONAL)-(26-8-2005).pdf

1014-MUM-2005-FORM 18(25-07-2008).pdf

1014-MUM-2005-FORM 2(COMPLETE)-(21-8-2006).pdf

1014-MUM-2005-FORM 2(GRANTED)-(16-12-2011).pdf

1014-MUM-2005-FORM 2(PROVISIONAL)-(26-8-2005).pdf

1014-MUM-2005-FORM 2(TITLE PAGE)-(COMPLETE)-(21-8-2006).pdf

1014-MUM-2005-FORM 2(TITLE PAGE)-(GRANTED)-(16-12-2011).pdf

1014-MUM-2005-FORM 2(TITLE PAGE)-(PROVISIONAL)-(26-8-2005).pdf

1014-mum-2005-form-1.pdf

1014-mum-2005-form-2 (complete).doc

1014-mum-2005-form-2 (complete).pdf

1014-mum-2005-form-2 (provisional).doc

1014-mum-2005-form-26.pdf

1014-mum-2005-form-3.pdf

1014-mum-2005-form-5.pdf

1014-MUM-2005-PETITION UNDER RULE-137(18-4-2012).pdf

1014-MUM-2005-REPLY TO EXAMINATION REPORT(23-3-2011).pdf

1014-MUM-2005-REPLY TO EXAMINATION REPORT(29-8-2011).pdf


Patent Number 250214
Indian Patent Application Number 1014/MUM/2005
PG Journal Number 51/2011
Publication Date 23-Dec-2011
Grant Date 16-Dec-2011
Date of Filing 26-Aug-2005
Name of Patentee CADILA HEALTHCARE LIMITED
Applicant Address Zydus Tower, Satellite Cross Road
Inventors:
# Inventor's Name Inventor's Address
1 LOHRAY BRAJ BHUSHAN Cadila Healthcare Limited, Zydus Tower, Satellite Cross Road, Ahmedabad-380015
2 LOHRAY VIDYA BHUSHAN Cadila Healthcare Limited, Zydus Tower, Satellite Cross Road, Ahmedabad-380015
3 PANDEY BIPIN Cadila Healthcare Limited, Zydus Tower, Satellite Cross Road, Ahmedabad-380015
4 DAVE MAYANK GHANSHYAMBHAI Cadila Healthcare Limited, Zydus Tower, Satellite Cross Road, Ahmedabad-380015
PCT International Classification Number C07D231/14
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA