US 7,459,553 B2
Process for the preparation of carboxamide compounds
Bobba Venkata Sivakumar, Navi Mumbai (India); Shekhar Bhaskar Bhirud, Navi Mumbai (India); Chandrasekhar Batchu, Navi Mumbai (India); and Sanjay Anantha Kale, Navi Mumbai (India)
Assigned to Glenmark Generics Ltd., Mumbai (India)
Filed on Mar. 11, 2005, as Appl. No. 11/77,723.
Claims priority of provisional application 60/552146, filed on Mar. 11, 2004.
Prior Publication US 2005/0203297 A1, Sep. 15, 2005
Int. Cl. C07D 223/18 (2006.01)
U.S. Cl. 540—589 34 Claims
 
1. A process for preparing a 5H-dibenz[b,f]azepine-5-carboxamide of the formula:

OG Complex Work Unit Drawing
wherein R1, R2, R3 and R4 are the same or different and can be hydrogen, halogen, nitro, cyano, carboxyl, R, —CO(R), —OCO(R), —O(R), —N(R)2, —CON(R)2, and —COO(R), wherein R is selected from the group consisting of C1-C10 alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C5-C10 cycloalkenyl, C2-C10 alkynyl, and C6-C20 aryl, and wherein the two R groups of —N(R)2 and —CON(R)2 can be the same or different, and wherein R2 and R3 can together form a bond; the process comprising reacting a 5H-dibenz[b,f]azepine of the formula

OG Complex Work Unit Drawing
wherein R1, R2, R3 and R4 have the aforementioned meanings, with one or more alkali or alkaline-earth cyanates and in the presence of one or more unsaturated dicarboxylic acid.