	US 7,601,715 B2
	Process for preparing triazole substituted azaindoleoxoacetic piperazine derivatives and novel salt forms produced therein
Nachimuthu Soundararajan, Kendall Park, N.J. (US); Yuping Qiu, Glastonbury, Conn. (US); Wenhao Hu, Princeton, N.J. (US); David R. Kronenthal, Yardley, Pa. (US); Pierre Sirard, St. Jean sur Richelieu (Canada); Jean Lajeunesse, Candiac (Canada); Robert Droghini, Candiac (Canada); Ramakrishnan Chidambaram, Pennington, N.J. (US); Xinhua Qian, Flemington, N.J. (US); Kenneth J. Natalie, Flemington, N.J. (US); Shawn K. Pack, Plainsboro, N.J. (US); Nathan Reising, Evansville, Ind. (US); Erqing Tang, Somerset, N.J. (US); Michael G. Fakes, Belle Mead, N.J. (US); Qi Gao, Wallingford, Conn. (US); Feng Qian, Hillsborough, N.J. (US); Blisse J. Vakkalagadda, North Brunswick, N.J. (US); Chiajen Lai, Kendall Park, N.J. (US); and Shan-Ming Kuang, Florence, S.C. (US)
Assigned to Bristol-Myers Squibb Company, Princeton, N.J. (US)
Filed on Jun. 19, 2006, as Appl. No. 11/455,338.
Claims priority of provisional application 60/693004, filed on Jun. 22, 2005.
Prior Publication US 2006/0293304 A1, Dec. 28, 2006
Int. Cl. A01N 43/58 (2006.01); A61K 31/50 (2006.01); A61K 31/497 (2006.01); C07D 239/00 (2006.01); C07D 239/02 (2006.01); C07D 241/00 (2006.01); C07D 241/02 (2006.01); C07D 295/00 (2006.01)

U.S. Cl. 514—247 [514/252.12; 544/242; 544/336; 544/358]

12 Claims

1. A process for preparing compound IA having the structure

where A is selected from the group consisting of C_1-6alkoxy, aryl and heteroaryl; in which said aryl is phenyl or naphthyl; said heteroaryl is selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, furanyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, quinolinyl, isoquinolinyl, benzofuranyl, benzothienyl, benzoimidazolyl and benzothiazolyl; and said aryl or heteroaryl is optionally substituted with one or two of the same or different members selected from the group consisting of amino, nitro, cyano, hydroxy, C_1-6alkoxy, —C(O)NH₂, C_1-6alkyl, —NHC(O)CH₃, halogen and trifluoromethyl; and

R¹⁸is H or alkyl;

R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵and R¹⁶are each independently H or (C_1-6)alkyl which may be optionally substituted with 1 to 3 same or different halogens;

which comprises reacting compound D having the structure

with a compound of the structure

in the presence of an organometallic base to form compound IA,

wherein the reaction is carried out at a temperature within the range from about −10 to about 30° C. and

where in compounds D and IA, R²is CH₃O, R¹is H and R³is H.