Sulindac derivatives
AssigneeKing Saud University
InventorsMashooq Ahmad Bhat, Mohamed A. Al-Omar, Nawaf Abdulaziz Alsaif, Syed Hidayathulla
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Abstract
The sulindac derivatives are compounds of the formula: wherein R is one of twenty-five substituted or unsubstituted phenyl substituents; and pharmaceutically acceptable salts thereof. The sulindac derivatives are synthesized by refluxing sulindac hydrazide with appropriately substituted benzaldehydes in the presence of ethanol and catalytic amounts of glacial acetic acid. The sulindac derivatives may be used as active ingredients in pharmaceutical compositions for the treatment of inflammation or inflammatory diseases. The sulindac derivatives may also be used as analgesic and/or gastric sparing agents.
Claims7
A sulindac derivative, comprising a compound having the formula:
- wherein R is selected from the group consisting of 2-nitrophenyl;
- 4-nitrophenyl;
- phenyl;
- 4-chlorophenyl;
- 3-hydroxyphenyl;
- 3-methoxyphenyl;
- 3-nitrophenyl;
- 4-dimethylaminophenyl;
- 2,4,5-trimethoxyphenyl;
- 3,4,5-trimethoxyphenyl;
- 4-hydroxyphenyl;
- 2-methoxyphenyl;
- 2,4-dimethoxyphenyl;
- 2,3-dimethoxyphenyl;
- 3,4-dimethoxyphenyl;
- 2,4,6-trimethoxyphenyl;
- 2,3,4-trimethoxyphenyl;
- 3-methoxy-4-ethoxyphenyl;
- 3,5-dimethoxy-4-hydroxyphenyl;
- 3-ethoxy-4-hydroxyphenyl;
- 2,5-dihydroxyphenyl;
- 3-hydroxy-4-methoxyphenyl;
- 2,3-dihydroxyphenyl;
- 2-hydroxy-3-methoxyphenyl;
- and 2,3,4-trihydroxyphenyl;
- or a pharmaceutically acceptable salt thereof.
A method of making sulindac derivatives, comprising the steps of:
- refluxing a methyl ester of sulindac and hydrazine hydrate in the presence of absolute ethanol to yield 2-[(1 Z)-5-fluoro-1-{[4-(methanesulfinyl) phenyl]methylidene}-2-methyl-1H-inden-3-yl]acetohydrazide;
- and
- refluxing a solution including the 2-[(1 Z)-5-fluoro-1-{[4-(methanesulfinyl) phenyl]methylidene}-2-methyl-1H-inden-3-yl]acetohydrazide and a substituted benzaldehyde in the presence of ethanol and glacial acetic acid to yield a 2-(5-methoxy-2-methyl-1-indol-3yl)-N-[(E)-substituted phenyl methylidine] acetohydrazide derivative, having the structure:
- wherein R is selected from the group consisting of 2-nitrophenyl;
- 4-nitrophenyl;
- phenyl;
- 4-chlorophenyl;
- 3-hydroxyphenyl;
- 3-methoxyphenyl;
- 3-nitrophenyl;
- 4-dimethylaminophenyl;
- 2,4,5-trimethoxyphenyl;
- 3,4,5-trimethoxyphenyl;
- 4-hydroxyphenyl;
- 2-methoxyphenyl;
- 2,4-dimethoxyphenyl;
- 2,3-dimethoxyphenyl;
- 3,4-dimethoxyphenyl;
- 2,4,6-trimethoxyphenyl;
- 2,3,4-trimethoxyphenyl;
- 3-methoxy-4-ethoxyphenyl;
- 3,5-dimethoxy-4-hydroxyphenyl;
- 3-ethoxy-4-hydroxyphenyl;
- 2,5-dihydroxyphenyl;
- 3-hydroxy-4-methoxyphenyl;
- 2,3-dihydroxyphenyl;
- 2-hydroxy-3-methoxyphenyl;
- and 2,3,4-trihydroxyphenyl.
Dependencies are inferred from the claim text.