Schering Corporation

Merck Sharp + Dohme Corp.

Schering-Plough Corporation

Knopp Biosciences, LLC

Daw-long Albert Kwok

Anantha R Sudhakar

Tiruvettipuram K Thiruvengadam

George G Wu

Tao Wang

Xiaojing Yang

Mingsheng Huang

Ngiap Kie Lim

Frank Xing Chen

Marc Poirier

Hoa N Nguyen

Jing Liao

Ji Xie

Jian Cui

Vijay Sabesan

Minzhang Chen

Ilia A Zavialov

Jeonghan Park

Michael D Green

George S K Wong

Eugene John Vater

Juergen Weber

Ingyu Jeon

Weidong Tong

Ramani R Raghavan

Maria M Tamarez

Michael J Humora

William F Kiesman

Weirong Chen

Erwin Irdam

Illia Zavialov

Ngiap-Kie Lim

The present invention is related to an improved process for the preparation of amino-substituted 4,5,6,7-tetrahydrobenzothiazole compounds of formula I, such as the compound 2-amino-4,5,6,7-tetrahydro-6-(n-propylamino)benzothiazole. The invention further relates to an improved synthesis of (R)-2-amino-4,5,6,7-tetrahydro-6-(n-propylamino)benzothiazole. The invention also relates to the methods and intermediates associated with the synthetic process.

Synthesis of amine substituted 4,5,6,7-tetrahydrobenzothiazole compounds

This application discloses a novel process for the preparation of himbacine analogs useful as thrombin receptor antagonists. The process is based in part on the use of a base-promoted dynamic epimerization of a chiral nitro center. The chemistry taught herein can be exemplified by the following: 

Exo- and diastereo-selective synthesis of himbacine analogs

Exo- and diastereo- selective synthesis of himbacine analogs

This application discloses a novel process for the synthesis of himbacine analogs, as well as the compounds produced thereby. The synthesis proceeds by alternative routes including the cyclic ketal amide route, the chiral carbamate amide route, and the chiral carbamate ester route. The compounds produced thereby are useful as thrombin receptor antagonists. The chemistry disclosed herein is exemplified in the following synthesis sequence: 

Exo-selective synthesis of himbacine analogs

In one embodiment, the present application relates to a process of making a compound of formula I. and to certain intermediate compounds that are made within the process of making the compound of formula I.

[object Object]

Exo- and diastereo- selective syntheses of himbacine analogs

Process and intermediates for the preparation of (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates for salts thereof

Growing community of inventors

Gillette, NJ, United States of America

Daw-long Albert Kwok