Esters and amides of non-steroidal anti-inflammatory carboxylic acids which may be used as anti-oxidants, 5-lipoxygenase inhibitors and non-steroidal anti-inflammatory products

US5811438A · kind A · utility

Assignee

• Alcon Laboratories, Inc. · US

Inventors

• Mark R. Hellberg · Arlington, US
• Gustav Graff · Cleburne, US
• Daniel A. Gamache · Arlington, US
• Jon C. Nixon · Fort Worth, US
• William H. Garner · Houston, US

Key dates

• Filing date: Jun 4, 1997
• Grant date: Sep 22, 1998
• Expiry date: Jun 4, 2017

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/72
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The compounds of the present invention are of the formula (I): A--X--(CH.sub.2).sub.n --Y--(CH.sub.3).sub.m --Z wherein: A is an non-steroidal anti-inflammatory agent (NSAIA); A--X is an ester or amide linkage derived from the carboxylic acid moiety of the NSAIA, wherein X is O or NR; R is H, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl; Y, if present, is O, NR, C(R).sub.2, CH(OH) or S(O).sub.n' ; n is 2 to 4 and m is 1 to 4 when Y is O, NR, or S(O).sub.n' ; n is 0 to 4 and m is 0 to 4 when Y is C(R).sub.2 or is not present; n is 1 to 4 and m is 0 to 4 when Y is CH(OH); n' is 0 to 2; and Z is (a), (b), (c), (d) or (e) wherein: R' and R.sup.3 are H, C(O)R, C(O)N(R).sub.2, PO.sub.3.sup.-, or SO.sub.3.sup.- ; R" is H or C.sub.1 -C.sub.6 alkyl; and R' and R.sup.3 together may form a ring having structure: (1) or (2); and provided that when Z is (e), X is not O. The compounds of the present invention also include pharmaceutically acceptable salts of the compounds of formula (I). Methods for treating inflammatory pathologies are disclosed. Particularly, the methods utilize pharmaceutical compositions containing certain compounds having an inti-inflammatory and anti-oxidant moiet…