US 7,321,041 B2
1,6 Naphthyridines useful as inhibitors of SYK kinase
Charles L. Cywin, Bethel, Conn. (US); Scott E. Jakes, Southbury, Conn. (US); Joachim Heider, Warthausen (Germany); Mark A. Bobko, Exton, Pa. (US); Renee L. Des Jarlais, St. Davids, Pa. (US); Mark Player, Phoenixville, Pa. (US); James Rinker, Reading, Pa. (US); Michael Winters, Lancaster, Pa. (US); and Bao-ping Zhao, West Windsor, N.J. (US)
Assigned to Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Conn. (US)
Filed on Apr. 15, 2003, as Appl. No. 10/413,980.
Application 10/413980 is a continuation of application No. 10/029714, filed on Dec. 21, 2001, abandoned.
Prior Publication US 2003/0229090 A1, Dec. 11, 2003
Int. Cl. C07D 471/02 (2006.01)
U.S. Cl. 546—122 6 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Drawing
wherein:
R3 is H, C1-3alkyl, halogen or phenyl;
R5 is N(R9)(R10) or OR11 wherein
R9 is H or C1-3alkyl,
R10 is aminoC2-6alkyl, C1-4alkylaminoC2-6alkyl, diC1-4alkylaminoC2-6alkyl, C1-4alkoxyC2-6alkyl or hydroxyC2-6alkyl, wherein one methylene group in said C2-6alkyl is optionally replaced with an oxygen, sulfur, NH, or NCH3, and wherein each methylene group in said C2-6alkyl is optionally substituted with a cyano or hydroxy group, or R10 is C3-7cycloalkyl, heterocycloalkyl, heteroaryl, except indazole, C3-7cycloalkylC1-4alkyl, heterocycloalkylC1-4alkyl, arylC1-4alkyl or heteroarylC1-4alkyl each optionally substituted with one or more C1-4alkyl, amino, C1-4alkylamino, diC1-4alkylamino, aminoC1-3alkyl, C1-4alkylaminoC1-3alkyl, diC1-4alkylaminoC1-3alkyl, halogen, hydroxy, aminocarboxy or benzyl groups, or R9 and R10 together with the nitrogen they are bonded to may form a heterocycloalkyl group containing one or more heteroatoms which is optionally substituted with one or more C1-4alkyl, amino, C1-4alkylamino, diC1-4alkylamino, aminoC1-3alkyl, C1-4alkylaminoC1-3alkyl, diC1-4alkylaminoC1-3alkyl, halogen, hydroxy, aminocarboxy or benzyl groups, and
R11 is aminoC2-6alkyl, C1-4alkylaminoC2-6alkyl, diC1-4alkylaminoC2-6alkyl, C1-4alkoxyC2-6alkyl or hydroxyC2-6alkyl, wherein one methylene group in said C2-6alkyl is optionally replaced with an oxygen, sulfur, NH, or NCH3, and wherein each methylene group in said C2-6alkyl is optionally substituted with a halogen, cyano or hydroxy group, or R11 is C3-7cycloalkyl, heterocycloalkyl, heteroaryl, C3-7cycloalkylC1-4alkyl, heterocycloalkylC1-4alkyl, arylC1-4alkyl or heteroarylC1-4alkyl each optionally substituted with one or more C1-4alkyl, amino, C1-4alkylamino, diC1-4alkylamino, aminoC1-3alkyl, C1-4alkylaminoC1-3alkyl, diC1-4alkylaminoC1-3alkyl, halogen, hydroxy, aminocarboxy or benzyl groups;
R7 is phenyl, naphthyl, thienyl, or 5-indolyl, optionally substituted with one or more C1-3alkoxy, halogen, CF3, CF3O, hydroxy, C1-3alkyl, amino, C1-3alkylamino, diC1-3alkylamino, C1-3alkylaminoC1-3alkyl, diC1-3alkylaminoC1-3alkyl, (C1-3alkylaminoC1-3alkyl)(C0-3alkyl)amino, (diC1-3alkylaminoC1-3alkyl)(C0-3alkyl)amino, C1-3alkylthio, aminocarboxy, C1-3alkylcarbonyl, ureido optionally substituted with C1-3alkyl, C(O)OC1-4alkyl, C(O)OH, acetamido or heterocycloaklyl groups, or with a phenyl group which is optionally substituted with one or more C1-3alkoxy, halogen, CF3, CF3O, hydroxy, C1-3alkyl, amino, C1-3alkylamino, diC1-3alkylamino, C1-3alkylaminoC1-3alkyl, diC1-3alkylaminoC1-3alkyl, C1-3alkylthio, aminocarboxy, C1-3alkylcarbonyl, ureido optionally substituted with C1-3alkyl, C(O)OC1-4alkyl, C(O)OH, acetamido, heteroaryl or heterocycloalkyl groups; and
R8 is H;
with the proviso that R3 is not hydrogen when R7 is methoxy-substituted phenyl and R5 is

OG Complex Work Unit Drawing
or a pharmaceutically acceptable salt thereof.