Ethenyl and ethynyl mercaptoalkyl pyridines
AssigneeMerck & Co., Inc.
InventorsTsung-Ying Shen, Howard Jones, Conrad P. Dorn
Life of this patent
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Abstract
Mercaptoalkylpyridines carrying an ethenyl or ethynyl substituent are prepared from known pyridine compounds, principally pyridoxine, by known chemical procedures, and are useful in the treatment of rheumatoid arthritis and related inflammatory diseases.
Claims21
A compound of structural formula:
- ##STR24## or pharmaceutically acceptable salt thereof wherein m is 0 or 1;
- R" is H or C.sub.2 -.sub.6 alkanoyl;
- A is ##STR25## or --C.tbd.C-- where R.sup.7 is hydrogen, chloro or fluoro;
- R is C.sub.1 -.sub.3 alkyl, hydroxy, C.sub.2 -.sub.6 alkanoyloxy, or hydroxy - C.sub.1 -.sub.3 alkyl;
- R.sup.1 and R.sup.2 are hydrogen or C.sub.1 - .sub.3 alkyl;
- and
- R.sup.4 is hydrogen, C.sub.1 -.sub.3 alkyl, phenyl, chloro, fluoro, or carboxyl.
2-Methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine or pharmaceutically acceptable salt thereof.
2-Methyl-3-hydroxy-4-mercaptomethylpyridine-5-acrylic acid or a pharmaceutically acceptable salt thereof.
2-Methyl-3-hydroxy-4-mercaptomethyl-5-(1-propenyl)pyridine or a pharmaceutically acceptable salt thereof.
2-Methyl-3-hydroxy-4-mercaptomethyl-5-ethynylpyridine or a pharmaceutically acceptable salt thereof.
2-Methyl-3-hydroxy-4-mercaptomethyl-5-styrylpyridine or pharmaceutically acceptable salt thereof.
An anti-inflammatory composition in unit dosage form comprising a pharmaceutically acceptable inert carrier and from 5 mg. to 5 gm. of a compound of structural formual:
- ##STR27## or pharmaceutically acceptable salt thereof wherein m is 0 or 1;
- R" is H or C.sub.2 -.sub.6 alkanoyl;
- A is ##STR28## or --C.tbd.C-- where R.sup.7 is hydrogen, chloro or fluoro;
- R is C.sub.1 -.sub.3 alkyl, hydroxy, C.sub.2 -.sub.6 alkanoyloxy, or hydroxy - C.sub.1 -.sub.3 alkyl;
- R.sup.1 and R.sup.2 are hydrogen or C.sub.1 -.sub.3 alkyl;
- and
- R.sup.4 is hydrogen, C.sub.1 -.sub.3 alkyl, phenyl, chloro, fluoro, or carboxyl.
A method of treating rheumatoid arthritis which comprises the administration, to a warm-blooded animal or human in need of such treatment, an effective amount of a compound of structural formula:
- ##STR30## or pharmaceutically acceptable salt thereof wherein m is 0 or 1;
- R" is H or C.sub.2 -.sub.6 alkanoyl;
- A is ##STR31## or -- C.dbd.C-- where R.sup.7 is hydrogen, chloro or fluoro;
- R is C.sub.1 -.sub.3 alkyl, hydroxy, C.sub.2-6 alkanoyloxy, or hydroxy - C.sub.1 -.sub.3 alkyl;
- R.sup.1 and R.sup.2 are hydrogen as C.sub.1 -.sub.3 alkyl;
- and
- R.sup.4 is hydrogen, C.sub.1 -.sub.3 alkyl, phenyl, chloro, fluoro, or carboxyl.
Dependencies are inferred from the claim text.