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US 4,536,507 AGranted
Prostaglandin antagonists
AssigneesMerck & Co., Inc., Merck Frosst Canada, Inc.
InventorsJoshua Rokach, Clarence S. Rooney, Edward J. Cragoe, Jr.
Life of this patent
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Abstract
Prostaglandin antagonists are disclosed which are 7- and 8-substituted-dizenzo[b,f]thiepins of the structural formula: ##STR1##
Claims26
A compound of the formula:
- ##STR58## wherein n is 0;
- Z is thio, sulfinyl, or sulfonyl;
- R is hydrogen, halogen including chloro, bromo, fluoro and iodo, amino, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkanoyl, hydroxyl, C.sub.1 to C.sub.4 alkoxy, thiol, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 alkylsulfinyl, C.sub.1 to C.sub.4 alkylsulfonyl, trifluoromethyl, trifluoromethylthio, cyano, carboxy, nitro and C.sub.1 to C.sub.4 alkyl or dialkylamino;
- A is 5-tetrazolyl, 3-hydroxy-1,2,5-thiadiazol-4-yl, 4-hydroxy-.DELTA..sup.3 -pyrroline-3-yl-2,5-dione or ##STR59## wherein R.sub.2 is hydroxy, lower alkoxy, N,N-diloweralkylaminoloweralkoxy, hydroxyloweralkoxy, carboxyloweralkoxy, amino, N-loweralkylamino, N,N-diloweralkylamino, loweralkylsulfonylamino, carboxyloweralkylamino, carboxamidoloweralkylamino and 2-imino-3-methylthioazolidine;
- and the dotted line indicates either an olefinic bond or saturation at the 10,11-position;
- and the broken double bonds indicating that a 10-oxo substituent can be present when the 10,11-position is saturated.
3 more elements
A composition for treating undesirable contractile activity of prostaglandins consisting essentially of a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of the formula ##STR61## wherein n is 0;
- Z is thio, sulfinyl, or sulfonyl;
- R is hydrogen, halogen including chloro, bromo, fluoro and iodo, amino C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkanoyl, hydroxyl, C.sub.1 C.sub.4 alkoxy, thiol, C.sub.1 to C.sub.4 alkylthio, C.sub.1 to C.sub.4 alkylsulfinyl, C.sub.1 to C.sub.4 alkylsulfinyl, trifluoromethyl, trifluoromethylthio, cyano, carboxy, nitro and C.sub.1 to C.sub.4 alkyl or dialkylamino;
- A is 5-tetrazolyl, 3-hydroxy-1,2,5-thiadiazol-4-yl, 4-hydroxy-.DELTA..sup.3 -pyrroline-3-yl-2,5-dione or ##STR62## wherein R.sub.2 is hydroxy, lower alkoxy, N,N-diloweralkylaminoloweralkoxy, hydroxyloweralkoxy, carboxyloweralkoxy, amino, N-loweralkylamino, N,N-diloweralkylamino, loweralkylsulfonylamino, carboxyloweralkylamino, carboxamidoloweralkylamino and 2-imino-3-methylthiazolidine;
- and the dotted line indicates either an olefinic except (+) (7 or 8) fluorodibenzo[b,f]thiepin-3-carboxylic acid-5-oxides;
- bond or saturation at the 10-, 11-position;
- and the pharmaceutically acceptable salts thereof.
3 more elements
Dependencies are inferred from the claim text.