823817-58-9

Upstream product

• 486460-32-6 sitagliptin 
• 823817-57-8 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine phosphate 
• 823817-56-7 (R/S)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine 

Downstream Products

• 486460-32-6 sitagliptin 
• 486459-71-6 Sitagliptin hydrochloride 
• 1240038-78-1 c 

Relevant academic research and scientific papers

SITAGLIPTIN, SALTS AND POLYMORPHS THEREOF

The present invention relates to an improved process for preparation of Sitagliptin or pharmaceutically acceptable salts thereof. The present invention further relates to novel polymorphs of Sitagliptin salts and process for preparation thereof.

IMPROVED PROCESS FOR PREPARATION OF (2R)-4-OXO-4-[3- (TRIFLUOROMETHYL)-5,6-DIHYDRO [1,2,4]-TRIAZOLO[4,3-A]PYRAZIN- 7(8H)-YL]-L-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINE and NEW IMPURITIES IN PREPARATION THEREOF

The present invention relates to synthesis of β-amino acid derivatives of formula (I) and its salts of formula (Ia) by a novel process. The process comprises the reduction of a protected or unprotected prochiral β-amino acrylic acid or derivative there of, by using borane containing reducing agents at atmospheric pressure. The resulting racemic β-amino compound is resolved to a pure stereoisomer of formula (I), specifically to (2R)-4-oxo-4- [3-Ctrifluoromethyl)-5, 6-dihydrol [1,2,4]triazolo [4,3-alpyrazin-7(8H)-yl]-1-(2,4,4-trifluorophenyl)butan-2-amine. In an embodiment the invention disclosed polymorphic forms of formula (I), phosphate salt of formula (I) and also a Dibenzoyl-L-tartaric acid salt of formula (I).

CRYSTALLINE FORMS OF SITAGLIPTIN PHOSPHATE

A Sitagliptin phosphate characterized by data selected from the group consisting of: a powder XRD pattern with peaks at 4.7, 13.5, 17.7, 18.3, and 23.7 ±0.2 degrees two theta; a powder XRD pattern with peaks at about 4.7, 13.5, and 15.5 ±0.2 degrees two theta and at least another two peaks selected from the following list: 14.0, 14.4, 18.3, 19.2, 19.5 and 23.7 ±0.2 degrees two theta; and a powder XRD pattern with peaks at about 13.5, 19.2, and 19.5 ±0.2 degrees two theta and at least another two peaks selected from the following list: 4.7, 14.0, 15.1, 15.5, 18.3, and 18.7 ±0.2 degrees two theta; a powder XRD pattern with peaks at about 13.5, 15.5, 19.2, 23.7, and 24.4 ±0.2 degrees two theta; and a powder XRD pattern with peaks at about 4.65, 13.46, 17.63, 18.30, and 23.66 ±0.10 degrees two theta, processes for preparing said Sitagliptin crystalline form, and pharmaceutical compositions thereof, are provided.