Back to results
US 12,709,766 B2Granted
Method for preparation of glycolipid carboxylic acids
AssigneeAnthem Biosciences Private Limited
InventorsGovinda Rajulu Gavara, Sumesh Eswaran, Rajendra Gaikwad, Amresh Kumar, Ganesh Sambasivam
Life of this patent
Estimating the term…
Abstract
The present invention relates to a method of preparation of Glycolipid carboxylic acids of Formula I by selective hydrolysis of corresponding esters by enzymes. The method provides preparation of compounds of Formula I in high yield by an environmentally benign, robust, economical, simple and convenient method.
Claims11
A process for preparing compounds of Formula (I)
- wherein:
- “n” ranges from 1-15;
- A1, A2 and A3 are each independently selected from H or
- Provided that A1, A2 and A3 together are not H;
- G is selected from the following groups:
- X is selected from the following groups:
- Y is selected from the following groups:
- and —NH—;
- Z is selected from the following groups:
- Wherein R2 is selected from alkyl, aryl, alkoxy, aryloxy or arylalkyl groups;
- “l” and “p” each independently ranges from 0-15;
- Comprising the step of:
- (a) Subjecting the compound of Formula (Ia)
- wherein R is selected from alkyl, aryl or aralkyl groups to hydrolysis in the presence of enzyme, selected from lipases, protease, amylase, trypsin, papain or combinations thereof, and water;
- (b). Stirring the reaction mixture of step (a) followed by concentrating, drying and dilution with solvent;
- (c) Removal of the enzyme solid precipitate from the reaction mixture of step (b) followed by purification to obtain compounds of Formula (I).
13 more elements
A process for preparing compounds of Formula (I′):
- Wherein:
- “n” ranges from 1-15;
- Wherein G is selected from the following groups:
- X is selected from the following groups:
- or Y is selected from the following groups:
- and —NH—;
- Z is selected from the following groups:
- Wherein R2 is selected from alkyl, aryl, alkoxy, aryloxy or arylalkyl groups;
- “l”, “m” and “p” each independently ranges from 0-15;
- Comprising the steps of:
- (i). Coupling a reactant selected from Glycolipid carboxylic acid of Formula (z-b)
- or a Glycolipid amine compound of Formula (z-bb) Formula (z-bb)
- with esters of Formula (z-c)
- to form compound of Formula (Ia)
- (ii). Subjecting the ester compound of Formula (Ia)′ to hydrolysis in presence of enzyme selected from lipases, protease, amylase, trypsin, papain or combinations thereof, and water to obtain compounds of Formula (I)′.
12 more elements
A process for preparing a compound of Formula (1-e)
- comprising the steps of:
- (i). Subjecting the Glycolipid carboxylic ester of Formula (1-a) to hydrolysis in presence of enzyme and water;
- to form Glycolipid carboxylic acid of Formula (1-b)
- (ii). Coupling compound of Formula (1-b) with esters of Formula (1-c)
- to form compound of Formula (1-d)
- (iii). Subjecting the ester compound of Formula (1-d) to hydrolysis in presence of enzyme and water to obtain compounds of Formula (1-e).
3 more elements
Dependencies are inferred from the claim text.