US 7,494,989 B2
Pyridine compounds useful as N-type calcium channel antagonists
Seiji Ohno, Kawasaki (Japan); Kayo Otani, Kawasaki (Japan); Seiji Niwa, Kawasaki (Japan); Satoshi Iwayama, Kawasaki (Japan); Akira Takahara, Kawasaki (Japan); Hajime Koganei, Kawasaki (Japan); Yukitsugu Ono, Kawasaki (Japan); Shinichi Fujita, Kawasaki (Japan); Tomoko Takeda, Kawasaki (Japan); Masako Hagihara, Kawasaki (Japan); and Akiko Okajima, Kawasaki (Japan)
Assigned to Ajinomoto Co., Inc., Tokyo (Japan)
Filed on Sep. 17, 2007, as Appl. No. 11/856,339.
Application 11/856339 is a division of application No. 10/387543, filed on Mar. 14, 2003, granted, now 7,288,544.
Application 10/387543 is a continuation of application No. PCT/JP01/07841, filed on Sep. 10, 2001.
Claims priority of application No. 2000-280438 (JP), filed on Sep. 14, 2000; and application No. 2001-126832 (JP), filed on Apr. 25, 2001.
Prior Publication US 2008/0070903 A1, Mar. 20, 2008
Int. Cl. C07D 213/82 (2006.01); C07D 213/80 (2006.01); C07D 401/06 (2006.01); A61K 31/455 (2006.01); A61K 31/496 (2006.01)
U.S. Cl. 514—217.04  [514/235.5; 514/253.13; 514/318; 514/343; 514/355; 514/356; 540/597; 544/124; 544/365; 546/194; 546/279.1; 546/316; 546/321] 30 Claims
 
1. A pyridine compound of formula (1″), or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Drawing
wherein A′ represents a group of the following general formula (9):

OG Complex Work Unit Drawing
wherein R16, R17, R18, R19 and R20 may be the same or different from each other and each represents a hydrogen atom, a halogen atom, hydroxyl group, carboxyl group, amino group, cyano group, nitro group, a lower alkyl group, a lower alkoxyl group or a lower alkylamino group, C′ and E′ may be the same or different from each other and each represents a hydrogen atom, a lower alkyl group which may contain a hetero atom in the chain thereof, dimethoxymethyl group, cyano group, an aryl-lower alkyl group, a heteroaryl-lower alkyl group, a hydroxy-lower alkyl group, an amino-lower alkyl group, a halogeno-lower alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or a group of the following general formula (3) or (4):

OG Complex Work Unit Drawing
wherein X2 represents O, S or N—R8, n represents an integer of 1 to 6, K in general formula (3) represents a hydrogen atom, a halogen atom, hydroxyl group, carboxyl group, amino group, cyano group, nitro group, azido group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, G in the general formula (4) represents N or C—H, wherein R6 to R8 may be the same or different from each other, and each represents a hydrogen atom, a linear, branched or cyclic, saturated or unsaturated hydrocarbon group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a hydroxy-lower alkyl group, a hydroxy-lower alkenyl group, an amino-lower alkyl group, an amino-lower alkenyl group, a halogeno-lower alkyl group, a halogeno-lower alkenyl group, an aryl-lower alkyl group, an aryl-lower alkenyl group, a heteroaryl-lower alkyl group, a heteroaryl-lower alkenyl group, a cyano-lower alkyl group or a cyano-lower alkenyl group, and the chains may contain a hetero atom, or R6 and R7 may together form a ring which may contain a hetero atom, B′ represents a hydrogen atom only when Y′ represents the general formula (12) and R26 is a substituted or unsubstituted aryl group, a carboxyl group only when Y′ represents the general formula (12) or Y′ and F′ together form the following general formula (12′-1), (12′-2), (12″-1) or (12″-2), or a group of the following general formula (10):

OG Complex Work Unit Drawing
wherein Z represents a nitrogen atom, an oxygen atom or a carbon atom, p represents an integer of 1 to 3, J is present only when Z is a nitrogen atom or a carbon atom and when present represents a hydrogen atom, a lower alkyl group which may contain a hetero atom in the group thereof, a hydroxy-lower alkyl group, an amino-lower alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryl-lower alkyl group or a substituted or unsubstituted heteroaryl-lower alkyl group, F′ represents the following general formula (11):

OG Complex Work Unit Drawing
wherein R21, R22, R23, R24 and R25 may be the same or different from each other and each represents a hydrogen atom, a halogen atom, hydroxyl group, carboxyl group, amino group, cyano group, nitro group, a lower alkyl group, a lower alkoxyl group, a lower alkylamino group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,X′ represents an oxygen atom or >NH,Y′ represents a saturated or unsaturated linear hydrocarbon group having 1 to 6 carbon atoms, which may contain a hetero atom in the group thereof, or a group of the following general formula (12):

OG Complex Work Unit Drawing
wherein R26 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group and h represents an integer of 0 to 5, Y′ and F′ together form a group of the following general formula (12′-1), (12′-2), (12″-1) or (12″-2):

OG Complex Work Unit Drawing
wherein h represents an integer of 0 to 5, i represents an integer of 2 to 5, R32, R33, R34 and R35 may be the same or different from each other and each represents a hydrogen atom, a halogen atom, hydroxyl group, carboxyl group, amino group, cyano group, nitro group, a lower alkyl group, a lower alkoxyl group, a lower alkylamino group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.