Title of Invention

PROCESS FOR MANUFACTURE OF 2-(2-FLUOROBIPHENYL) PROPIONIC ACID (FLURBIPROFEN)

Abstract A process for preparation of Flurbiprofen,which comprises alkylation of 2,4 difluronitrobenzene with dimethy1 ethy1 malonate and subsequent reduction with a hydrogenation catalyst to yield amino-diester followed by Gomberg reaction with benzene to obtain Flurbiprofen crude.Flurbiprofen (crude) is purified through sodium salt and re-precipitation to obtain pure Flurbiprofen.
Full Text FORM 2
THE PATENT ACT 1970
(39 of 1970)&The Patents Rules, 2003
COMPLETE SPECIFICATION
(See section 10 and rulel3)
1. TITLE OF THE INVENTION:
Process For Manufacture Of 2-(2-FluorobiphenyI)Propionic Acid (Flurbiprofen)
2. APPLICANT (S)
(a) NAME: FDC Limited
(b) NATIONALITY: Indian company incorporated under the Companies
Act 1956
(c) ADDRESS: 142-48, Swami Vivekananda Road, Jogeshwari (W), Mumbai - 400 102, Maharashtra, India.
3. PREAMBLE TO THE DESCRIPTION
The following specification particularly describes the invention and the manner in
which it is to be performed.

Field of Invention:
The present invention relates to the process for manufacture of 2-(2-fluorobiphenyl) propionic acid (Flurbiprofen) of formula -1.

Background of Invention:
Flurbiprofen is a non-steroidal - anti-inflammatory, analgesic agent. The compound efficiently works in pain management and has, therefore, gained wide use in the preparation of anti-inflammatory medicines. Its anti-inflammatory activity is about 240 times that of aspirin and analgesic activity, is about 180 times that of aspirin in standard laboratory tests. However despite this high activity, the toxicity (LD50) is only 1.2 to 2.4 times greater than that of aspirin in standard laboratory tests.
Diethyl 2-(3-chloro-4-nitrophenyl)-2-methylmalonate and Diethyl 2-(3-chloro-4-aminophenyl)-2-methylmalonate are known as intermediates for the preparation of tertiary amino acid derivatives of 2-(3-chloro-4-aminophenyl)-2-propionic acid having anti-inflammatory properties. Carney, et al, disclosed in Experientia 29/8, p 938 (Aug. 15,1973)"A Potent Non-Steroidal Anti-inflammatory Agent: 2-[3-chloro-4- (3-pyrrolinyl)phenyl] propionic acid"; British Pat. No. 1,316,312 partially corresponding to Swiss pat. Nos.574,921-2, 574,924-6; Example 1 of Swiss Pat. No.574, 924 and further Makosza, et al discussed in "Reaction of Organic Anions", Part LVII. The problem of Competitive Nucleophilic Substitution of Ortho- and Para-Halogens in 2,4-Dihalo Nitrobenzene by some Carbanions," discussed by Roczniki Chemii in Ann. Soc. Chim. Polonorum 50, p. 1850 (1976).
2

It is well known in the art that base catalysed condensation of methyl malonic ester with 2,4-difluronitrobenzene gives substituted methyl malonic esters which are useful intermediates for making aryl propionic acids having pharmaceutical applications.
US 3,755,427 and US 3,793,457 discloses multi-step synthesis of flurbiprofen starting from 4-bromoacetophenone. Other processes as disclosed in US 3,784,705; 3,901,906; 3,959,364; 2,533,397; Japan Kokai No. 75,40,540 (1975); and German Pat. No. 2,613,812, provides a number of intermediates for manufacturing flurbiprofen which involves potentially hazardous reactants (i.e., the Schiemann reaction for introduction of fluorine).
US 4,266,069, US 4,398,035 and US 4,324,904 teaches preparation of compounds viz., dialkyl 2-(3-fluro-4-nitrophenyl)-2-methylmalonate and dialkyl 2-(3-fluoro-4-aminophenyl)-2-methylmalonate useful as intermediates for preparaing 2-(2-fluoro-4-biphenyl)propionic acid, known as Flurbiprofen as the formula -1 and esters thereof.

US 4,266,069 (Eq. 4398035, 4324904, EP 0032620) discloses a process for preparation of dialkyl 2-(3-fluoro-4-nitrophenyl)-2-methylmalonate and a four step synthesis of dialkyl 2-(3-fluoro-4-aminophenyl)-2-methylmalonate as useful for preparing 2-(2-fluoro-4-biphenylyl)propionic (flurbiprofen) wherein multiple solvents were used in the reaction steps and reduction is followed by using reducing agent such as iron or tin in an aqueous acidic medium with sodium dithionate or with zinc in acetic acid.
3

US 4,107,439 also describes process for preparing 2-aryl-substituted C3 to C6 -alkanoate esters by reacting enol ether derivative of an aryl C2 to C5 -alkyl ketone with a trivalent thallium salt in an organic liquid medium containing alcohol, water or other nucleophile.
Flurbiprofen was produced by (i) reacting 2-fluoronitrobenzene with an alpha-substituted propionitrile in aprotic solvent and in the presence of a base to form 2-(3-fluoro-4-nitrobenzene)propionitrile (ii) reducing 2-(3-fluoro-4-nitrobenzene)propionitrile to 2-(4-amino-3-fluorobenzene)propionitrile (iii) converting 2-(4-amino-3-fluorobenzene) propionitrile into 2-(2-fluoro-4-biphenylyl)propionitrile by Gomberg-Bachmann reaction with benzene, and (iv) converting 2-(2-fluoro-4-biphenylyl)propionitrile into 2-(2-fluoro-4-biphenylyl)propionic acid (flurbiprofen) as disclosed in patent US 4,370,278.
In US 4,371,473 preparation of 2-(2-fluoro-4-biphenyl)propionic acid by converting 2-amino-4-methyl-biphenyl into 2-fluoro-4-methylbiphenyl followed by bromination of methyl group to form 2-fluoro-4-monobromomethylbiphenyl which was further transformed into 2-(2-fluoro-4-biphenylyl)acetonitrile and further converted to flurbiprofen via the corresponding propionitrile is disclosed.
US 4,518,799 claims process for preparation of the intermediate 4-bromo-2-fluoroaniline by bromination of flouro aniline which was coupled with benzene to make the arylmagnesium bromide and further reacted with ethylene in presence of a catalyst to make Grignard compound and subsequently conversion into desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.
US 4,540,795 discloses process for preparing 2-(3-fluoro-4-nitrobenzene)ethyl-4,4-dimethyloxazoline by reacting fluoronitro aromatic compound with alpha-substituted 2-alkyloxazoline in inert solvent and in the presence of base which was further hydrogenated to 2-(4-amino-3-fluorobenzene)ethyl-4,4-dimethyloxazoline and further converted to 2-(2-fluoro-4-biphenylyl)ethyl-4,4-dimethyloxazoline by Gomberg-Bachmann reaction and subsequently converted to 2-(2-fluoro-4-biphenylyl)propionic acid.
4

US 4,544,509 describes coupling of 2-(4-amino-3-fluorobenzene)propionitrile with benzene in the presence of water and inorganic nitrite such as sodium nitrite to biary compound intermediates which were further used to prepare flurbiprofen.
DE3247215 claims the process of preparation of 4-Cyano-2-fluorobiphenyl by reacting the bromine compound with copper cyanide or by reacting 4-amino-3-fluorobenzonitrile with benzene in the presence of nitrite which was used for further synthesis of flurbiprofen.
GB2087886 describes process for preparing a biphenyl compound comprises coupling an aniline compound and a benzene compound. In a first aspect, the reaction is conducted in the presence of a metal nitrite. In a second aspect, the reaction is conducted in the presence of an alkyl nitrite.
Our Indian granted patent INI 86920 describes an improved process for the manufacture of substituted malonic esters using esters as solvent of choice for condensation reaction. This application is a continuation of our study in improving the overall manufacturing process for the Flurbiprofen.
The reduction procedure employed in most of the prior art patents involves use of costly noble metal catalysts such as palladium, platinum, iron, zinc or tin hydrochloride as reagent of choice, for reduction of nitro groups to corresponding amino group. These catalysts are expensive thereby making the process not economically viable.
The use of these reagents leads to the formation of huge amount of sludge, thus increasing environmental load of effluent. The prior art processes are thus industrially hazardous, difficult to carry out, and have lead to huge amount of industrial waste.
Aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide used to perform the reaction as disclosed in US 4,266,069 and US 4,398,904 are (i) highly toxic, (ii) difficultly recoverable, (iii) difficulty biodegradable and (iv) pose major problem for effluent treatment.
5

In the present invention benzene is used as a solvent for process of preparation of substituted methyl malonic ester which does not have the disadvantages of the prior art solvents retaining the other advantageous properties.
In the preferred embodiment of the present invention Raney Nickel which is inexpensive catalyst, is used for hydrogenating the nitro diester compound to corresponding amido diester compound.
The catalyst and solvent used in the present invention are routinely recycled, reused and suitable for industrial scale-up, thereby making the process economically viable.
The Gomberg reaction is next processed in situ, employing Cupric chloride and Isobutyl nitrite yielding propanedioic acid, (2-fluoro[l,l'-biphenyl]-4-yl)methyl-, diethyl ester which is isolated by vacuum distillation by a "short path distillation unit". The distilled ester is saponified, decarboxylated to Flurbiprofen crude. Purification of the crude product is effected by formation of sodium salt and re-precipitation by treatment with acid to obtain pure Flurbiprofen.
Objects of the Invention:
An object of the present invention is to provide an economical, and efficient green process for preparation of 2-(2-fluorobiphenyl)propionic acid (Flurbiprofen) with high yields which employs single solvent such as benzene thus making the process convenient to carry out in one pot thereby reducing substantially the chemical waste.
Yet another object of the invention is to provide a process for preparation of 2-(2-fluorobiphenyl)propionic acid (Flurbiprofen), which employs single solvent such as benzene and an inexpensive Raney Nickel catalyst, avoiding the use of costly noble metal catalyst like Pd/c, Pt/c. The catalyst and solvent used in the invention are routinely recycled, reused and suitable for industrial scale-up.
Another objective of the invention is to provide a process for preparation of 2-(2-fluorobiphenyl)propionic acid (Flurbiprofen), wherein the high vacuum distillation is carried out using "short path distillation unit".
6

Further, it is an object of the present invention to use solvent which can be easily recovered, recycled and affords facile reaction for process of preparation of substituted methyl malonic esters eliminating the limitations of the prior art solvents while retaining the other advantageous properties.
It is an another object of the present invention is to carry out subsequent reduction and Gomberg reaction without isolating product of first and second stage and thus making overall process facile and operated like one-pot.
Summary of Invention:
An economical, and efficient green process for preparation of 2-(2-fluorobiphenyl)propionic acid (Flurbiprofen) with high yields employing single solvent thus making the process convenient to carry out in one pot is disclosed.
The process of the present invention for preparation 2-(2-fluorobiphenyl)propionic acid (Flurbiprofen) of formula-1, comprising the steps of;
a) alkylating 2,4-Difluronitrobenzene with diethyl methyl malonate (formula III) in an aromatic hydrocarbon solvent in presence of base to yield nitrodiester ( formula II),
b) reducing of nitrodiester to aminodiester using suitable hydrogenation catalyst in an organic solvent ( formula - IV ),
c) subjecting the aminoester (formula IV) to Gomberg reaction with benzene in presence of alkyl nitrite and cupric chloride to yield propanediol acid, (2-fluoro[l,r-biphenyi]-4-yl)methyl-, diethyl ester (formula V),
d) treating biaryl diester (formula V) with alkali to form sodium salt of flurbiprofen dihydrate and
e) converting sodium salt of flurbiprofen to flurbiprofen (formula I) by acid treatment.
Detailed Description of Invention:
Making Active Pharmaceutical Ingredients (APIs) requires long chain of chemical reactions and a large quantity of solvent, in order to achieve overall process efficiency. It is mandatory to involve reactions, which are more efficient and
7

environment friendly. Pharmaceutical companies do produce huge amounts of hazardous waste, per year. Green manufacturing program's undertaken in many industries, center around efficient waste management and making the entire process green from the start. The present invention describes a process for preparation of 2-(2-fluorobiphenyOpropionic acid (Flurbiprofen) of formula -1.



Formula -I
More specifically the present invention provides process for preparation of substituted methyl malonic ester (formula II)



(Formula - II)
where R1 and R are the same or different selected from the group consisting of hydrogen and alkyl of from Q to C6 carbon atoms, comprises reacting compound of formula -HI,

(Formula - III) 8

wherein R & R1 are as defined above, with 2,4-Difluoronitrobenzene in presence of a base selected from the group consisting of alkali metal hydroxides, or carbonates and mixtures thereof more preferably potassium carbonate in a suitable solvent.
According to the present invention, there is provided a process for preparation of 2-(2-fluorobiphenyl)propionic acid (Flurbiprofen), (formula - I), comprising alkylation of 2,4-Difluronitro benzene using dimethyl ethyl malonate (formula III) in an aromatic hydrocarbon solvent at 50°- 100°C to form Nitro-diester (formula - II). The aromatic hydrocarbon solvent used for alkylation reaction may be toluene, benzene, xylene or combination thereof, more preferably benzene.
The compound of formula-II is then reduced with suitable hydrogenation catalyst in an organic solvent at 20° - 70°C and 5.0 - 55.0 psi gauge pressure preferably 35° - 45°C and 25 - 50 psi gauge pressure to form amino-diester (formula - IV).The hydrogenation catalyst used may be selected from Raney Nickel, Palladium, Platinum or Platinum Oxide, more preferably Raney Nickel. The organic solvent used in hydrogenation of compound (formula-II) may be selected from benzene, methanol, ethanol, tetrahydrofuran, acetic acid, or combination thereof, more preferably benzene.

(Formula - IV)
The compound (formula- IV) is further subjected to Gomberg reaction in an aromatic hydrocarbon solvent to yield Propanediol acid, (2-fluoro[l,r-biphenyl]-4-yl)methyl-, diethyl ester (formula V) which is purified by short path distillation. The solvent used in Gomberg reaction of compound of formula- IV, is benzene which is already present in the reaction mass right from stage I being carried forward without getting contaminated.
9


(Formula - V)
Biaryl diester (formula-V) is further subjected to saponification on treatment with alkali, decarboxylation and subsequently treated with alkali to form sodium salt of flurbiprofen dihydrate which is further processed to flurbiprofen (formula I) upon acidification.
The process of the present invention substantially reduces formation of by-products and gives high yield of the product. It employs cheaper and easily available raw materials and eliminates use of hazardous reagents. It is, therefore, efficient, economical and convenient to carry out. More importantly the solvent used for the first three steps is same and hence the process is operated as one pot without isolation of intermediates in first two steps.
The invention is further described and exemplified by the detailed examples which follow but they are not intended to limit the scope of the invention.
Examples 1
Preparation of 2-(3-fluro-4-nitrophenyl)malonic acid, diethyl ester (Formula - II): In clean and dry 2KL reactor was charged successively with 1000L benzene and (1.8 KMole) 250 kg potassium carbonate. The temperature of the reaction mass was raised to 40°- 45°C and 330 kg diethyl methyl malonate (1.8 Kmole) was next added maintaining temperature at 45°- 50°C. Difluronitrobenzene 250 kg (1.6 Kmole) was then added ensuring temperature does not exceeding to 60° - 65 °C. Resulting reaction mass was digested at 60° - 65°C for four hours and then cooled to 30° - 35°C. Reaction mass was washed with water 3 x 250L till to obtain neutral pH. Organic and aqueous layer were separated. Organic layer contains 2-methyl -2-(3-fluro-4-nitrophenyl)malonic acid, diethyl ester (formula-II).
10

The above experiment was carried out with different mole ratios of raw materials at different condition the result obtained are shown in the Table-1. Purity was determined by Gas Chromatography (G.C.)
Table-1

Expt. No. Raw Materials G.C. purity of Formula - II
Difluronitrobenzene Diethyl methyl malonate Potassium Carbonate Benzene
A-l 250 kg (1.57 Kmole) 330 kg (1.896 Kmole) 250 kg (1.8 Kmole) 1000 L 75%
A-2 250 kg (1.57 Kmole) 295.8 kg (1.7 Kmole) 250 kg (1.8 Kmole) 1000 L 72%
A-3 250 kg (1.57 Kmole) 348 kg (2 Kmole) 272 kg (2 Kmole) 1000 L 75%
Example 2
Preparation of 2-methyl -2-(3-amino-4-fluro phenyl)malonic acid, diethyl ester. (Formula
-IV):
Clean and dry 1 KL Hydrogenator was successively charged with benzene layer
containing 2-methyl -2-(3-fluro-4-nitrophenyl) malonic acid, diethyl ester prepared in
example 1 and 8.75 kg Raney Nickel catalyst was added. The Hydrogenator was
pressured to 3 kg/cm2 with hydrogen at temperature 35° - 45 °C. After 5 hours, the
resulting mass was cooled to 30° - 32 °C and Raney Nickel catalyst was filtered on hyflo
bed, which was recycled for three consecutive batches. The resulting filtrate contain 2-
methyl -2-(3-amino-4-fluro phenyl)malonic acid, diethyl ester (Formula - IV) which was
used as such in next reaction.
The reaction was monitored by Gas chromatography (G.C.)
The above experiment was carried out with different mole ratios of raw materials at different condition the result obtained are shown in the Table-2. Gas Chromatography
11

G.C determined purity. The reaction using different quantity of catalyst gives G.C. purity 60% - 70%
Table-2

Sr. No. Raney Nickel Quantity G.C. Purity Hydrogen pressure Temperature
B-l 8.75 kg (3.5%) 65% 2 kg/ cm2 60°C
B-2 25 kg (10%) 70% 3 kg/ cm2 70°C
B-3 15 kg (6%) 68% 5 kg/ cm2 50°C
Example-3
Preparation of 2-methyl -2-(3-fluro-4-biphenyl) malonic acid, diethyl ester Isobutyl nitrite
preparation:
A clean and dry 1 KL reactor was charged with 400 L water, 160 kg sodium nitrite and 188
L isobutyl alcohol. Resulting reaction mass was cooled to 5°C and 126 L Hydrochloric
acid at 5° - 10°C was added in lots in 2 hours. Aqueous and organic layers were separated.
Organic layer contain isobutyl nitrite
Another 1KL reactor was charged benzene layer containing 2-methyl -2-(4-amino-3-fluorophenyl) malonic acid, diethyl ester of example -2 and 86 kg cupric chloride. The resulting mass was heated to 80° - 82°C and organic layer of Isobutyl nitrite was added to it slowly. Reaction mass was digested for 1 hour at 80° - 82°C and was next washed with 56 L Sulphuric acid at 45 °C - 50°C. Aqueous and organic layers were separated. Organic layer was washed with 4 x 1000 L water till pH neutral and was subjected to normal distillation to recover benzene, which is recycled. The crude oil (GC puriy 55-60%) obtained was subjected to short path distillation to yield 2-methyl -2-(3-fluro-4-nitrophenyl) malonic acid, diethyl ester (formula-V) of 75 - 80% purity .Yield: 188-195 kg
12

Example - 4
Preparation of sodium salt of Flurbiprofen i.e. 2-(2-fluorobiphenyl)propionic acid, sodium salt:
1 KL reactor was charged with 160 L caustic lye and 2-methyl -2-(2-fluro-4-biphenyl)malonic acid, diethyl ester (formula-V) 188 kg, at 70° -75°C. 700 L water was next added and the reaction mass heated to 80° -85°C to yield a clear solution, which is washed with 2 x 130 L Ethylene dichloride. To aqueous layer was added 160 L acetic acid at 80° -85°C in 2 hours. Resulting reaction mass was digested at 80° - 85°C for 2 hours and then cooled to 10°C ,stirred for l hour and centrifuged. The cake thus obtained was then washed with 100 L chilled water and spins dried. Product was dried at 50 - 60°C for 12 hours to yield sodium salt of flurbiprofen 115-120 kg
Example - 5
Preparation of Flurbiprofen:
1 KL reactor was charged with 650 L distilled water and 115 kg sodium salt of
flurbiprofen. Reaction mass was next heated to 70° -75°C and the clear solution was
filtered. Filtrate was cooled to 30° - 35°C and 37 L hydrochloric acid was next added till
pH is acidic (pH = 2-3) and was digested at 45° - 50°C for 2 hours. Reaction mass was
cooled to 25° - 30°C and stirred for 1 hour, filtered and washed with 3 x 100 L water. The
resultant cake was first spin dried and then dried at temperature 60° - 65°C for 12 hours to
yield flurbiprofen. Yield: 80-88 kg
13

We claim,
1. A process for preparation of 2-(2-fluorobiphenyl)propanoic acid (Flurbiprofen) (formula-I )comprising the steps of:

a) alkylating 2,4-Difluronitrobenzene using diethyl methyl malonate (formula III) in an aromatic hydrocarbon solvent in presence of base to yield nitrodiester (formula II),

14
b) reducing nitrodiester ( formula II) to aminodiester using suitable hydrogenation catalyst in organic solvent (formula - IV),


c) subjecting the said aminoester (formula IV) to Gomberg reaction with organic solvent in presence of alkyl nitrite and cupric chloride to yield propanedioic acid, (2-fluoro[l,r-biphenyl]-4-yl)methyl-, diethyl ester (formula V),

d) treating the biaryl diester (formula V) with alkali to form sodium salt of flurbiprofen dihyrate and
e) converting the sodium salt of flurbiprofen to flurbiprofen by reprecipitating on acidification (formula I).

2. The process as claimed in claim 1, wherein the said aromatic hydrocarbon solvent used for alkylation is selected from toluene, benzene, xylene or combination thereof, more preferably benzene.
3. The process as claimed in claim 1, wherein the said base used in alkylation reaction is selected from the group of sodium hydroxide, potassium hydroxide and potassium carbonate preferably potassium carbonate.
4. The process as claimed in claim 1, wherein the alkylation reaction is carried out at temperature 50-100°C.
5. The process, as claimed in claim 1, wherein the said hydrogenation catalyst is selected from Raney nickel, Palladium, Platinum or Platinum Oxide, more preferably Raney Nickel.
6. The process as claimed in claim 1, wherein the hydrogenation catalyst Raney
Nickel is recycled and reused minimum three times
7. The process as claimed in claim 1, wherein hydrogenation is carried out at
temperature range 20°-70°C and 5-55 psi gauge pressure, preferably 35°-45°C
and 25.0 - 50.0 psi gauge pressure.
15

8. The process as claimed in claim 1, wherein the organic solvent used in hydrogenation reaction is selected from benzene, methanol, ethanol, tetrahydrofuran, acetic acid, or combination thereof, more preferably benzene.
9. The process as claimed in claim 1, wherein the said alkyl nitrite is isobutyl nitrite.
10. The process as claimed in claim 1, wherein the reaction of steps a), b) and c) is carried out in one pot using benzene as solvent.
11. The process as claimed in claim 1 wherein biaryl diester (formula V) of step c) is further purified by short path distillation.
12. A process for preparation of Flubiprofen as substantially described herein with reference to foregoing examples 1 to 11.
Dated this 31st day of July 2006
Dr. Gopakumar G. Nair Agent for the Applicant
16

ABSTRACT:
A process for preparation of Flurbiprofen, which comprises alkylation of 2,4 difluronitrobenzene with dimethyl ethyl malonate and subsequent reduction with a hydrogenation catalyst to yield amino-diester followed by Gomberg reaction with benzene to obtain Flurbiprofen crude. Flurbiprofen (Crude) is purified through sodium salt and re-precipitation to obtain pure Flurbiprofen.
17

Documents:

1208-MUM-2006-ABSTRACT(25-2-2009).pdf

1208-MUM-2006-ABSTRACT(31-7-2006).pdf

1208-mum-2006-abstract(granted)-(27-5-2009).pdf

1208-mum-2006-abstract.doc

1208-mum-2006-abstract.pdf

1208-MUM-2006-CANCELLED PAGES(25-2-2009).pdf

1208-MUM-2006-CLAIMS(25-2-2009).pdf

1208-MUM-2006-CLAIMS(31-7-2006).pdf

1208-MUM-2006-CLAIMS(AMENDED)-(25-2-2009).pdf

1208-mum-2006-claims(granted)-(27-5-2009).pdf

1208-mum-2006-claims.doc

1208-mum-2006-claims.pdf

1208-mum-2006-correspondence others.pdf

1208-mum-2006-correspondence received-ver-31-07-2006.pdf

1208-mum-2006-correspondence received-ver-4-09-2006.pdf

1208-MUM-2006-CORRESPONDENCE(22-3-2007).pdf

1208-MUM-2006-CORRESPONDENCE(25-2-2009).tif

1208-MUM-2006-CORRESPONDENCE(IPO)-(1-7-2009).pdf

1208-MUM-2006-DESCRIPTION(COMPLETE)-(25-2-2009).pdf

1208-MUM-2006-DESCRIPTION(COMPLETE)-(31-7-2006).pdf

1208-mum-2006-description(granted)-(27-5-2009).pdf

1208-MUM-2006-FORM 1(31-7-2006).pdf

1208-MUM-2006-FORM 1(4-9-2006).pdf

1208-MUM-2006-FORM 18(22-3-2007).pdf

1208-mum-2006-form 2(25-2-2009).pdf

1208-MUM-2006-FORM 2(COMPLETE)-(31-7-2006).pdf

1208-mum-2006-form 2(granted)-(27-5-2009).pdf

1208-MUM-2006-FORM 2(TITLE PAGE)-(25-2-2009).pdf

1208-MUM-2006-FORM 2(TITLE PAGE)-(COMPLETE)-(31-7-2006).pdf

1208-mum-2006-form 2(title page)-(granted)-(27-5-2009).pdf

1208-MUM-2006-FORM 3(25-2-2009).pdf

1208-MUM-2006-FORM 3(31-7-2006).pdf

1208-MUM-2006-FORM 5(25-2-2009).pdf

1208-MUM-2006-FORM 9(4-9-2006).pdf

1208-mum-2006-form-1.pdf

1208-mum-2006-form-2.doc

1208-mum-2006-form-2.pdf

1208-mum-2006-form-26.pdf

1208-mum-2006-form-3.pdf

1208-mum-2006-form-9.pdf


Patent Number 234415
Indian Patent Application Number 1208/MUM/2006
PG Journal Number 28/2009
Publication Date 10-Jul-2009
Grant Date 27-May-2009
Date of Filing 31-Jul-2006
Name of Patentee FDC Limited
Applicant Address 142-48,Swami Vivekananda Road,Jogeshwari(W),Mumbai-400 102
Inventors:
# Inventor's Name Inventor's Address
1 Joshi,Shreerang Vidhyadhar 142-48,Swami Vivekananda Road,Jogeshwari(W),Mumbai-400 102
2 Joshi,Nilesh Chandrakant 142-48,Swami Vivekananda Road,Jogeshwari(W),Mumbai-400 102,
3 Kanekar,Santosh Anant 142-48,Swami Vivekananda Road,Jogeshwari(W),Mumbai-400 102
4 Bhorgay,Dilip Baburao 142-48,Swami Vivekananda Road,Jogeshwari(W),Mumbai-400 102,
5 Chandavarkar Mohan Anand 142-48,Swami Vivekananda Road,Jogeshwari(W),Mumbai-400 102,
PCT International Classification Number C07C51/02
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA