Mercaptoketones and mercaptoalcohols and a process for their pre

Details Mercaptoketones and mercaptoalcohols and a process for their pre Mercaptoketones and mercaptoalcohols and a process for their pre

1997-07-02

1998-12-22

Kumar, Shailendra

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

544335, 546164, 546165, 546175, 546329, 5483044, 5483097, 5483361, 548491, 549 58, 549 76, 549467, 549496, 549483, 549488, 558436, 560147, 562581, 564138, 564139, C07C32112, C07C23102

Patent

active

058522131

ABSTRACT:
This invention relates to matrix metalloproteinase (MMP) inhibiting compounds of the formula: ##STR1## where R.sup.1 is C.sub.1 -C.sub.12 alkyl, straight or branched and optionally substituted by halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, amino, carboxyl, C.sub.1 -C.sub.6 alkoxycarbonyl, carboxamido, nitrile, mono- or di-(C.sub.1 -C.sub.6)alkylamino, thio, C.sub.1 -C.sub.6 alkylthio, aryl, --Oaryl or --OCH.sub.2 aryl where aryl is optionally substituted with C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, carboxy, halogen, cyano, nitro, carboxamido, or hydroxy; and C.sub.1 -C.sub.6 alkanesulfonyloxy. R.sup.2 is .alpha.-OH or .beta.-OH and R.sup.6 is H or R.sup.2 and R.sup.6 together are carbonyl; the chemical intermediates; and processes for the preparation of these compounds and the intermediates thereto.
Matrix metalloproteinases (MMP) are a family of zinc-containing calcium dependent proteinases, including stromelysins, collagenases, and gelatinases. These MMP enzymes are capable of degrading the proteinaceous components of connective tissue and appear to be involved in tissue remodeling, i.e., wound healing and connective tissue turnover. Unexpectedly, the mercaptoalcohols with the S-configuration at the hydroxyl-bearing carbon have been found to be at least 4 times more potent than the analogous (R)-alcohols both in vitro and in vivo in inhibiting the MMP enzyme.

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