Hydroxamic acid derivatives with tricyclic substitution

Details Hydroxamic acid derivatives with tricyclic substitution Hydroxamic acid derivatives with tricyclic substitution

1996-10-29

1998-03-24

Shah, Mukund J.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548144, 548226, 5482634, 5483171, 548512, 548513, 5483147, 546242, 546 18, 546210, 544 94, 544286, 544 55, 544 56, 544122, 544370, 540450, 540597, 540602, C07D28510, C07D20932, C07D21136, C07D26526

Patent

active

057314411

ABSTRACT:
The invention provides hydroxamic acid derivatives of the general formula ##STR1## wherein R.sup.1 represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; R.sup.2 represents a saturated 5- to 8-membered monocyclic or bridged N-heterocyclic ring, which N-heterocyclic ring is attached via the N atom and when it is monocyclic, optionally contains NR.sup.4, O, S, SO or SO.sub.2 as a ring member and/or is optionally substituted on one or more C atoms by hydroxy, lower alkyl, lower alkoxy, oxo, ketalized oxo, amino, mono(lower alkyl)amino, di(lower alkyl)amino,carboxy, lower alkoxycarbonyl, hydroxy-methyl, lower alkoxymethyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or hydroxyimino; R.sup.3 represents a 5- or 6-membered N-heterocyclic ring which (a) is attached via the N atom, (b) optionally contains N, O and/or S, SO or SO.sub.2 as an additional ring member, (c) is substituted by oxo on one or both C atoms adjacent to the linking N atom and (d) is optionally benz-fused or optionally substituted on one or more other C atoms by lower alkyl or oxo and/or on any additional N atom(s) by lower alkyl or aryl; R.sup.4 represents hydrogen, lower alkyl, aryl, aralkyl or a protecting group; m stands for 1 or 2 and n stands for 1-4, pharmaceutically acceptable salts thereof, intermediates used in the manufacture thereof, and methods of use therefor. Compounds of formula I are collagenase inhibitors useful in the control or prevention of degenerative joint diseases such as rheumatoid arthritis and osteoarthritis or in the treatment of invasive tumours, atherosclerosis or multiple sclerosis.

REFERENCES:
patent: 4611064 (1986-09-01), Schefczik
patent: 5318964 (1994-06-01), Broadhurst et al.
patent: 5536434 (1996-07-01), Venturello et al.
Zanger, et al., "Structure-Activity Relationship and Drug Design", Remington's Pharmaceutical Science, Osol et al. ed., 16th ed., Philadelphia College of Pharmacy and Science, pp. 420-435 (1980).

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