US 7,531,658 B2
Process for the preparation of 17-N-substituted-carbamoyl-4-aza-androst-1-en-3-ones
Zhi-Xian Wang, Brantford (Canada); Alfredo Paul Ceccarelli, Brantford (Canada); Mohammed Abdul Raheem, Brantford (Canada); and Bhaskar Reddy Guntoori, Brantford (Canada)
Assigned to Apotex Pharmachem Inc., Brantford (Canada)
Filed on Jan. 20, 2006, as Appl. No. 11/335,782.
Prior Publication US 2007/0173523 A1, Jul. 26, 2007
Int. Cl. C07D 221/18 (2006.01)
U.S. Cl. 546—77 39 Claims
 
1. A process for the preparation of 17-amido-3-oxo-4-azasteroid of formula 2

OG Complex Work Unit Drawing
comprising the steps of:
a) reacting in the presence of a solvent 17-carboxylic acid-3-oxo-4-azasteroid of formula 3

OG Complex Work Unit Drawing
wherein R is selected from hydrogen, alkyl, aryl and aralkyl groups, and A is
(i) —CH2CH2—, or
(ii) —CH═CH—
with the compound of formula 4

OG Complex Work Unit Drawing
wherein X is C or S, to generate the compound of formula 5

OG Complex Work Unit Drawing
wherein R and A are as defined above; and
b) reacting the compound of formula 5 with an amine of formula R1R2NH, wherein R1 and R2 are individually selected from hydrogen, alkyl, aryl and aralkyl groups, in the presence of a heterocyclic hydroxyl activator compound.