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US 6,472,530 B1Granted
Benzo-fused dithiepino[6,5-b]pyridines, and related compositions and methods
AssigneeOrtho-McNeil Pharmaceutical, Inc.
InventorsJohn H. Dodd, Kenneth C. Rupert, James L. Bullington, Daniel A. Hall
Life of this patent
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Abstract
This invention provides novel dithiepino[6,5-b]pyridines of the following formulae: These compounds are useful as calcium channel antagonists with cardiovascular, antiasthmatic and antibronchoconstriction activity. Thus, this invention also provides pharmaceutical compositions, as well as methods, for preventing and treating disorders such as hypersensitivity, allergy, asthma, bronchospasm, dysmenorrhea, esophageal spasm, glaucoma, premature labor, urinary tract disorders, gastrointestinal motility disorders and cardiovascular disorders.
Claims42
A compound of Formula I,
- or a pharmaceutically acceptable salt thereof, wherein
- (a) R1, R2, R3, R4 and R5 are independently selected from the group consisting of H, OH, halogen, cyano, NO2, alkyl, C1-8 alkoxy, C1-8 alkylsulfonyl, C1-4 carboalkoxy, C1-8 alkylthio, difluoromethoxy, difluoromethylthio, trifluoromethyl and oxadiazole (formed by R1 and R2);
- (b) R6 is selected from the group consisting of H, C1-5 straight or branched alkyl, aryl, 3-piperidyl, N-substituted 3-piperidyl, N-substituted 2-pyrrolidinyl methylene and substituted alkyl, wherein said N-substituted 3-piperidyl and said N-substituted 2-pyrrolidinyl methylene may be substituted with C1-8 straight or branched chain alkyl or benzyl, and said substituted alkyl may be substituted with C1-8 alkoxy, C2-8 alkanoyloxy, phenylacetyloxy, benzoyloxy, hydroxy, halogen, p-tosyloxy, mesyloxy, amino, carboalkoxy or NR′R″, wherein
- (i) R′ and R″ are independently selected from the group consisting of H, C1-8 straight or branched alkyl, C3-7 cycloalkyl, phenyl, benzyl and phenethyl, or (ii) R′ and R″ together form a heterocyclic ring selected from the group consisting of piperidino, pyrrolidino, morpholino, thiomorpholino, piperazino, 2-thieno, 3-thieno and an N-substituted derivative of said heterocyclic rings, said N-substituted derivative being substituted with H, C1-8 straight or branched alkyl, benzyl, benzhydryl, phenyl and/or substituted phenyl (substituted with NO2, halogen, C1-8 straight or branched chain alkyl, C1-8 alkoxy and/or trifluoromethyl);
- (c) R7 is selected from the group consisting of H, amino, alkyl, aryl, trifluoromethyl, alkoxymethyl, 2-thieno and 3-thieno;
- and
- (d) R is SO or SO2.
4 more elements
A compound of Formula II,
- or a pharmaceutically acceptable salt thereof, wherein
- (a) R1, R2, R3, R4 and R5 are independently selected from the group consisting of H, OH, halogen, cyano, NO2, alkyl, C1-8 alkoxy, C1-8 alkylsulfonyl, C1-4 carboalkoxy, C1-8 alkylthio, difluoromethoxy, difluoromethylthio, trifluoromethyl and oxadiazole (formed by R1 and R2);
- (b) R7 is selected from the group consisting of H, amino, alkyl, aryl, trifluoromethyl, alkoxymethyl, 2-thieno and 3-thieno;
- (c) R8 is selected from the group consisting of -alkyl-OH, alkylamine, lactone, cyclic carbonate, alkyl-substituted cyclic carbonate, aryl-substituted cyclic carbonate, -aryl-C(O)OR′″, -alkyl-aryl-C(O)OR′″, -alkyl-OC(O)R′″, -alkyl-C(O)R′″, -alkyl-C(O)OR′″, -alkyl-N(R″″)C(O)R′″ and -alkyl-N(R″″)C(O)OR′″, wherein R′″ and R″″ are independently selected from the group consisting of hydrogen, amino, alkyl, aryl, aryl-fused cycloalkyl and the amino, alkyl, aryl, aryl-fused cycloalkyl heterocyclyl being optionally substituted with halogen, cyano, NO2, lactone, amino, alkylamino, aryl-substituted alkylamino, amide, carbamate, carbamoyl, cyclic carbonate, alkyl, halogen-substituted alkyl, arylalkyl, alkoxy, and/or aryl (the aryl being optionally substituted with OH, halogen, cyano, NO2, alkyl, amino, dimethylamino, alkoxy, alkylsulfonyl, C1-4 carboalkoxy, alkylthio and/or trifluoromethyl);
- and
- (d) R is SO or SO2.
3 more elements
Dependencies are inferred from the claim text.