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“Improved Process For The Preparation Of Propane 1,2,3 Triyl Tris(4 Phenylbutanoate) (Glycerol Phenyl Butyrate)”

Abstract: The present invention relates to an improved process for the preparation of substantially pure propane-1,2,3 -triyl tris(4-phenylbutanoate) (Glycerol phenylbutyrate) (1) with purity greater than 99%.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
16 July 2019
Publication Number
04/2021
Publication Type
INA
Invention Field
CHEMICAL
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, Telangana India-500033

Inventors

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

Specification

We claim:
1. A process for the preparation of Glycerol phenylbutyrate (1) having purity
greater than 99.0% comprising:
a) reacting glycerol (2) with 4- phenylbutyric acid (3) in the presence of a base and a coupling agent; and
b) isolating Glycerol phenylbutyrate (1).

2. The process according to claim 1, wherein the base used in step a) is selected from triethyl amine, imidazole, pyridine, and picoline.
3. The process according to claim 1, wherein the solvent used in step a) is selected from dimethylformamide (DMF), and dimethylsulfoxide (DMSO).
4. The process according to claim 1, wherein the coupling agent used in step a) is selected form Diisopropylcarbodiimide (DIC), Dicyclohexyl carbodiimide (DCC), N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC.HC1), U'-Carbonyldiimidazole (CDI), and 1-Hydroxybenzotriazole (HOBt).

5. The process according to claim 1, wherein the base used is catalytic amount of 4-Dimethylaminopyridine (DMAP).
6. A process for the purification of Glycerol phenylbutyrate (1), comprising

a) providing a solution of Glycerol phenylbutyrate (1) in a protic solvent;
b) heating the reaction mixture to a suitable temperature;
c) separating organic layer;
d) adding an aprotic solvent to the product layer;
e) adding activated carbon and filtering; and
f) isolating pure Glycerol phenylbutyrate (1).
7. The process according to claim 6, wherein the protic solvent used in step a)
is selected form methanol, ethanol, isopropyl alcohol and water.
8. The process according to claim 6, wherein the aprotic solvent used in step
d) is selected form dichloromethane, n-hexane, n-heptane, cyclohexane, and
acetonitrile.

9. The process according to claim 6, wherein the suitable temperature employed in step b) is 50-60 °C.
10. The process according to claim 6, wherein the Glycerol phenylbutyrate (1) having purity greater than 99.0% and one more of the following

a) less than 0.05% of Impurity B;
b) less than 0.05% of impurity C; and
c) less than 0.05% of impurity D.

Documents

Application Documents

# Name Date
1 201941028552-PROVISIONAL SPECIFICATION [16-07-2019(online)].pdf 2019-07-16
2 201941028552-FORM 1 [16-07-2019(online)].pdf 2019-07-16
3 Correspondence by Agent_Form 1_16-08-2019.pdf 2019-08-16
4 201941028552-FORM 3 [15-07-2020(online)].pdf 2020-07-15
5 201941028552-ENDORSEMENT BY INVENTORS [15-07-2020(online)].pdf 2020-07-15
6 201941028552-COMPLETE SPECIFICATION [15-07-2020(online)].pdf 2020-07-15
7 201941028552-Correspondence_Form2-Form-Form5 and Specification_03-09-2020.pdf 2020-09-03