Process for preparing a benzoate salt of a 1-(3-aminopyrrolidine-1-carbonyl)-3,4-diphenylbenzene compound
AssigneesAstex Pharmaceuticals, Inc., Taiho Pharmaceutical Co., Ltd.
InventorsNipun Davar, Matthew Johnson, Suresh Manthati
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Abstract
A process for preparation of benzoate salt of 4-[5-[(3S)-3-aminopyrrolidine-1-carbonyl]-2-[2-fluoro-4-(2-hydroxy-2-methyl-propyl)phenyl]phenyl]-2-fluoro-benzonitrile, designated herein as Compound (A), and methods of using Compound (A) are provided. (I)
Claims23
A process for preparing benzoate salt of Compound (A):
- comprising:
- (i) extracting Compound (A):
- into 2-methyl tetrahydrofuran (2-Me THF) from a reaction mixture comprising Compound (A) to obtain a solution of Compound (A) in 2-Me THF;
- (ii) conducting a solvent exchange from 2-Me THF to isopropyl alcohol (IPA) to obtain a solution of Compound (A) in IPA;
- and
- (iii) adding benzoic acid to the solution of Compound (A) in IPA under conditions sufficient to obtain the benzoate salt of Compound (A).
A process for preparing benzoate salt of Compound (A):
- comprising
- (i) contacting Compound (B):
- with aqueous hydrochloric acid to obtain Compound (A):
- (ii) extracting Compound (A) into 2-methyl tetrahydrofuran (2-Me THF) to obtain a solution of Compound (A) in 2-Me THF;
- (iii) conducting a solvent exchange from 2-Me THF to isopropyl alcohol (IPA);
- (iv) adding benzoic acid to the mixture comprising IPA under conditions sufficient to obtain benzoate salt of Compound (A);
- and
- (v) recrystallizing the benzoate salt of Compound (A).
A benzoate salt of Compound (A) comprising no more than 0.7% a/a, total, of any of the following compounds or a combination thereof:
A pharmaceutical composition comprising benzoate salt of Compound (A) and comprising no more than 0.7% a/a total, of any of the following compounds or a combination thereof:
Dependencies are inferred from the claim text.