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US 4,400,395 AGranted
Allylsulfoxide enzyme inhibitors
AssigneeMerck & Co., Inc.
InventorRaymond A. Firestone
Life of this patent
Estimating the term…
Abstract
Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
Claims6
A compound of structural formula:
- ##STR61## or a pharmaceutically acceptable salt thereof wherein X is hydrogen, fluoro, chloro, bromo, iodo, C.sub.2-4 alkanoyloxy, toluenesulfonyloxy, benzenesulfonyloxy, C.sub.1-3 alkanesulfonyloxy, p-nitrobenzoyloxy, or ##STR62## Y is hydrogen or ##STR63## and Z is fluoro, chloro, bromo, iodo, C.sub.2-4 alkanoyloxy, toluenesulfonyloxy, benzenesulfonyloxy, C.sub.1-3 alkanesulfonyloxy, p-nitrobenzoyloxy, or ##STR64## or Y and Z taken together form .dbd.CH.sub.2 ;
- with the proviso that one and only one of X, Y and Z is a sulfoxide, and one and only one of X and Z is halo;
- wherein
- R is
- (1) phenyl,
- (2) nitrophenyl,
- (3) cyanophenyl,
- (4) C.sub.1-3 alkylsulfonylphenyl,
- (5) C.sub.1-3 alkoxycarbonylphenyl,
- (6) di(trifluoromethyl)phenyl,
- (7) o-C.sub.1-3 alkylphenyl, or
- (8) o,o-di(C.sub.1-3 alkyl)phenyl;
- and
- R.sup.1 is
- (1) 3,4-dihydroxyphenyl, or
- (2) 4-hydroxyphenyl.
13 more elements
A pharmaceutical enzyme inhibiting composition comprising a pharmaceutical carrier and an effective enzyme inhibiting amount of a compound of structural formula:
- ##STR65## or a pharmaceutically acceptable salt thereof wherein X is hydrogen, fluoro, chloro, bromo, iodo, C.sub.2-4 alkanoyloxy, toluenesulfonyloxy, benzenesulfonyloxy, C.sub.1-3 alkanesulfonyloxy, p-nitrobenzoyloxy, or ##STR66## Y is hydrogen or ##STR67## and Z is fluoro, chloro, bromo, iodo, C.sub.2-4 alkanoyloxy, toluenesulfonyloxy, benzenesulfonyloxy, C.sub.1-3 alkanesulfonyloxy, p-nitrobenzoyloxy, or ##STR68## or Y and Z taken together form .dbd.CH.sub.2 ;
- with the proviso that one and only one of X, Y and Z is a sulfoxide, and one and only one of X and Z is halo;
- wherein
- R is
- (1) phenyl,
- (2) nitrophenyl,
- (3) cyanophenyl,
- (4) C.sub.1-3 alkylsulfonylphenyl,
- (5) C.sub.1-3 alkoxycarbonylphenyl,
- (6) di(trifluoromethyl)phenyl,
- (7) o-C.sub.1-3 alkylphenyl, or
- (8) o,o-di(C.sub.1-3 alkyl)phenyl;
- and
- R.sup.1 is
- (1) 3,4-dihydroxyphenyl, or
- (2) 4-hydroxyphenyl.
13 more elements
A method of inhibiting enzymes in a patient in need of such treatment which comprises the administration of an enzyme inhibitory amount of a compound of structural formula:
- ##STR69## or a pharmaceutically acceptable salt thereof wherein X is hydrogen, fluoro, chloro, bromo, iodo, C.sub.2-4 alkanoyloxy, toluenesulfonyloxy, benzenesulfonyloxy, C.sub.1-3 alkanesulfonyloxy, p-nitrobenzoyloxy, or ##STR70## Y is hydrogen or ##STR71## and Z is fluoro, chloro, bromo, iodo, C.sub.2-4 alkanoyloxy, toluenesulfonyloxy, benzenesulfonyloxy, C.sub.1-3 alkanesulfonyloxy, p-nitrobenzoyloxy, or ##STR72## or Y and Z taken together form .dbd.CH.sub.2 ;
- with the proviso that one and only one of X, Y and Z is a sulfoxide, and one and only one of X and Z is halo;
- wherein
- R is
- (1) phenyl,
- (2) nitrophenyl,
- (3) cyanophenyl,
- (4) C.sub.1-3 alkylsulfonylphenyl,
- (5) C.sub.1-3 alkoxycarbonylphenyl,
- (6) di(trifluoromethyl)phenyl,
- (7) o-C.sub.1-3 alkylphenyl, or
- (8) o,o-di(C.sub.1-3 alkyl)phenyl;
- and
- R.sup.1 is
- (1) 3,4-dihydroxyphenyl, or
- (2) 4-hydroxyphenyl.
13 more elements
Dependencies are inferred from the claim text.