Substituted cinnamic acid amides for treating pain
AssigneeNippon Zoki Pharmaceutical Co., Ltd.
InventorsTomohiro Ookubo, Ko Nakamura, Yoshitaka Nakazawa, Hiroyoshi Nanba, Hiroyuki Yoshida
Life of this patent
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Abstract
A cinnamic acid amide derivative having an excellent analgesic action is disclosed herein. The cinnamic acid amide derivative shows excellent analgesic actions to not only a nociceptive pain model animal, but also a neuropathic pain model animal, which is very useful as an agent for treating various pain diseases showing acute or chronic pains or neuropathic pains. The cinnamic acid amide derivative may be a compound represented by formula (I).
Claims19
A compound of formula (I):
- or a pharmaceutically acceptable salt or hydrate thereof,
- where:
- n is 1, 2, 3, or 4;
- each of X1 and X2 is independently selected from the group consisting of hydrogen, fluoro, trifluoromethyl, and carboxy, with the proviso that one of X1 and X2 is selected from the group consisting of fluoro, trifluoromethyl, and carboxy;
- R1 is selected from the group consisting of:
- (1) imidazolyl, substituted with alkyl having 3 to 6 carbon atoms or phenyl;
- (2) pyrrolyl, optionally substituted with alkyl having 1 to 4 carbon atoms;
- (3) phenyl, substituted with amino, isoxazolyl, or morpholino;
- (4) phenyl, substituted with thiomorpholino, optionally substituted with oxo;
- (5) piperazine, substituted with alkyl having 1 to 4 carbon atoms or cyclohexyl;
- (6) thiomorpholino, optionally substituted with one or two oxos;
- (7) indazolyl;
- and
- (8) cyclohexylamino;
- and
- R2 is selected from the group consisting of hydrogen, cyano, and alkyl having 1 to 4 carbon atoms.
A pharmaceutical agent comprising, as an active ingredient, a compound of formula (I):
- or a pharmaceutically acceptable salt or hydrate thereof, and a pharmaceutically acceptable carrier,
- where:
- n is 1, 2, 3, or 4;
- each of X1 and X2 is independently selected from the group consisting of hydrogen, fluoro, trifluoromethyl, and carboxy, with the proviso that one of X1 and X2 is selected from the group consisting of fluoro, trifluoromethyl, and carboxy;
- R1 is selected from the group consisting of:
- (1) imidazolyl, substituted with alkyl having 1 to 6 carbon atoms or phenyl;
- (2) pyrrolyl, optionally substituted with alkyl having 1 to 4 carbon atoms;
- (3) phenyl, substituted with amino, isoxazolyl, or morpholino;
- (4) phenyl, substituted with thiomorpholino, optionally substituted with oxo;
- (5) piperazino, substituted with alkyl having 1 to 4 carbon atoms or cyclohexyl;
- (6) thiomorpholino, optionally substituted with one or two oxos;
- and
- (7) benzoimidazolyl;
- (8) indazolyl;
- (9) pyrazolyl;
- (10) triazolyl;
- (11) pyrrolidinyl;
- (12) piperidine;
- (13) azepanyl;
- (14) morpholino;
- and
- (15) cyclohexylamino;
- and
- R2 is selected from the group consisting of hydrogen, cyano, and alkyl having 1 to 4 carbon atoms.
A compound, which is (E)-3-(2-fluorophenyl)-N-[3-(isoxazol-5-yl)phenyl]-2-propenamide.
Dependencies are inferred from the claim text.