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“Improved Process For The Preparation Of 4 Amino 5 Hexenoic Acid (Vigabatrin)”

Abstract: ABSTRACT The present invention relates to an improved process for the preparation of 4-amino-5-hexenoic acid (1) with purity greater than 99.0% by HPLC.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
30 October 2018
Publication Number
18/2020
Publication Type
INA
Invention Field
POLYMER TECHNOLOGY
Status
Email
radha@biophore.com
Parent Application

Applicants

Biophore India Pharmaceuticals Pvt. Ltd
Plot#92; 1-98/2/92, Kavuri Hills – Phase II, Jubilee Hills, Hyderabad

Inventors

1. Manik Reddy Pullagurla
Plot#92; 1-98/2/92, Kavuri Hills – Phase II, Jubilee Hills, Hyderabad - 500033.
2. Jagadeesh Babu Rangisetty
Plot#92; 1-98/2/92, Kavuri Hills – Phase II, Jubilee Hills, Hyderabad - 500033.

Specification

We claim:
1. A process for the preparation of Vigabatrin (1) having purity greater
than 99.0% comprising:
a) reaction of l,4-dichlorobut-2-ene (2) with diethyl malonate (3) in the presence of a base to form diethyl 2-vinylcyclo propane-1,1-dicarboxylate (4);
b) ammonolysis of 2-vinylcyclo propane-1,1-dicarboxylate (4) in an organic solvent to form 2-oxo-5-vinylpyrrolidine-3-carboxamide (5); and
c) hydrolysis of 2-oxo-5-vinylpyrrolidine-3-carboxamide (5) in the presence of acid to form Vigabatrin (1).

2. The process according to claim 1, wherein the base used in step a) is selected from tri ethylamine, sodium methoxide and sodium ethoxide.
3. The process according to claim 1, wherein the organic solvent used in step b) is selected from methanol, ethanol, isopropanol, dimethyl formamide, formamide, N-methyl formamide or mixtures thereof.
4. The process according to claim 1, wherein the acid used in step c) is selected from hydrochloric acid, hydrobromic acid, methane sulfonic acid, toluene sulfonic acid and trifluoro acetic acid.
5. A process for the purification of Vigabatrin (1), which comprising:

a) providing a solution of Vigabatrin (1) in a solvent or mixture of solvents;
b) heating the reaction mixture to a suitable temperature;
c) optionally, treating with neutral charcoal;
d) adding a protic solvent; and
e) isolating pure Vigabatrin (1).
6. The process according to claim 5, wherein solvent used is selected
from methanol, ethanol, isopropanol, water, dimethyl formamide,
formamide, N-methyl formamide or mixtures thereof.

7. The process according to claim 5, wherein step b) is carried out at a temperature of 40-60 °C and preferably 50-60 °C
8. The process according to claim 1, wherein Vigabatrin obtained is having purity grater than 99% and characterized by one or more of the following;
i. less than 0.10% of 5-vinylpyrrolidin-2-one (impurity A);
and ii. less than 0.10%) of 2-(2-aminobut-3-en-l-yl)malonic
acid (impurity E).

Documents

Application Documents

# Name Date
1 201841040963-PROVISIONAL SPECIFICATION [30-10-2018(online)].pdf 2018-10-30
2 201841040963-FORM 1 [30-10-2018(online)].pdf 2018-10-30
3 201841040963-DRAWINGS [30-10-2018(online)].pdf 2018-10-30
4 201841040963-FORM FOR SMALL ENTITY [29-10-2019(online)].pdf 2019-10-29
5 201841040963-FORM 3 [29-10-2019(online)].pdf 2019-10-29
6 201841040963-EVIDENCE FOR REGISTRATION UNDER SSI [29-10-2019(online)].pdf 2019-10-29
7 201841040963-ENDORSEMENT BY INVENTORS [29-10-2019(online)].pdf 2019-10-29
8 201841040963-ENDORSEMENT BY INVENTORS [29-10-2019(online)]-1.pdf 2019-10-29
9 201841040963-DRAWING [29-10-2019(online)].pdf 2019-10-29
10 201841040963-COMPLETE SPECIFICATION [29-10-2019(online)].pdf 2019-10-29
11 Correspondence by Applicant_Form-2,FORM-5,Form-3_14-11-2019.pdf 2019-11-14
12 201841040963-FORM 18 [17-10-2022(online)].pdf 2022-10-17
13 201841040963-FER.pdf 2022-11-03
14 201841040963-Proof of Right [03-05-2023(online)].pdf 2023-05-03
15 201841040963-FER_SER_REPLY [03-05-2023(online)].pdf 2023-05-03
16 201841040963-CLAIMS [03-05-2023(online)].pdf 2023-05-03
17 201841040963-ABSTRACT [03-05-2023(online)].pdf 2023-05-03
18 201841040963-Form 2(Title Page)-010923.pdf 2023-10-05
19 201841040963 Form 7A Pre-grant opposition 010923.pdf 2024-02-29

Search Strategy

1 SearchStrategy201841040963E_28-10-2022.pdf