US 7,482,339 B2
2-Naphthylimino-1,3-thiazine derivative
Hiroyuki Kai, Osaka (Japan); Yasuhide Morioka, Toyonaka (Japan); and Katsumi Koike, Koka (Japan)
Assigned to Shionogi and Co., Ltd., Osaka (Japan)
Appl. No. 10/568,963
PCT Filed Aug. 24, 2004, PCT No. PCT/JP2004/012086
§ 371(c)(1), (2), (4) Date Feb. 21, 2006,
PCT Pub. No. WO2005/026138, PCT Pub. Date Mar. 24, 2005.
Claims priority of application No. 2003-300952 (JP), filed on Aug. 26, 2003.
Prior Publication US 2006/0281738 A1, Dec. 14, 2006
Int. Cl. C07D 417/02 (2006.01); A61K 31/541 (2006.01)
U.S. Cl. 514—227.2  [544/6; 544/55; 514/226.8] 16 Claims
 
1. A compound represented by the formula (I):

OG Complex Work Unit Drawing
wherein R2 and R3 are the same or different and each is C2-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxyC1-C4 alkyl, optionally substituted aminoC1-C4 alkyl, or C3-C6 cycloalkylC1-C4 alkyl; or
R2 and R3 are taken together with the adjacent carbon atom to form an optionally substituted 5 to 8 membered non-aromatic carbocyclic ring or an optionally substituted 5 to 8 membered non-aromatic heterocyclic ring;
R4 is C1-C6 alkyl, hydroxyC1-C6alkyl, optionally substituted aminoC1-C6alkyl, or C1-C6 alkoxyC1-C6 alkyl;
X is an oxygen atom or a sulfur atom;
A is a group of the formula:

OG Complex Work Unit Drawing
wherein R1 is, same or different, alkyl, alkoxy, alkylthio, optionally substituted amino, optionally substituted aryl, optionally substituted aryloxy, optionally substituted aralkyloxy, cycloalkyl, a halogen atom, hydroxy, nitro, haloalkyl, haloalkoxy, optionally substituted carbamoyl, carboxy, alkoxycarbonyl, alkylsulfinyl, alkylsulfonyl, alkoxylalkyl, alkylthioalkyl, optionally substituted aminoalkyl, alkoxyiminoalkyl, alkoxyalkoxy, alkylthioalkoxy, alkoxycarbonylalkoxy, carboxyalkoxy, alkylsulfonyloxy, optionally substituted heteroaryl, an optionally substituted non-aromatic heterocyclic group, cyano, cyanoalkoxy, or a group of the formula: —C(═O)—RH wherein RH is a hydrogen atom, alkyl, optionally substituted aryl, or an optionally substituted non-aromatic heterocyclic group;
W is —CH2CH2CH2—, —CH2CH2CH2CH2—, —OCH2O—, —OCH2CH2O—, —N(CH3)CH2CH2CH2—, or —CH═CH—CH═CH—;
n is an integer of 0 to 7;
wherein the optionally substituted amino is non-substituted amino, C1-C4 alkylamino, (C1-C4 alkyl)carbonylamino, aryl carbonylamino, N—(C1-C4 alkyl)carbonyl-C1-C4 alkylamino, aralkylamino, C1-C4 alkylsulfonylamino, C2-C4 alkenyloxycarbonylamino, (C1-C4 alkoxy)carbonylamino, C2-C4 alkenylamino, arylcarbonylamino, or heteroarylcarbonylamino,
the substituent of optionally substituted carbamoyl is selected from the group consisting of alkyl and acyl, and,
the substituent of non-aromatic carbocyclic ring, non-aromatic heterocyclic ring, aryl, aryloxy, aralkyloxy, heteroaryl, and a non-aromatic heterocyclic group is selected from the group consisting of hydroxy, carboxy, a halogen atom, haloalkyl, haloalkoxy, alkyl, alkenyl, formyl, acyl, alkynyl, cycloalkyl, alkoxy, alkoxycarbonyl, nitro, nitroso, oxo, optionally substituted amino, azido, aryl, aryloxy, cyano, isocyano, isocyanato, thiocyanato, isothiocyanato, mercapto, alkylthio, alkylsulfonyl, arylsulfonyl, optionally substituted carbamoyl, sulfamoyl, formyloxy, haloformyl, oxalo, thioformyl, thiocarboxy, dithiocarboxy, thiocarbamoyl, sulfino, sulfo, sulfoamino, hydrazino, ureido, amidino, guanidino, formyloxy, thioxo, alkoxyalkoxy, and alkylthioalkoxy,
a pharmaceutically acceptable salt thereof.