Title:
DERIVATIVES OF CYCLIC PHENOLIC THIOETHERS AS INHIBITORS OR STIMULATORS OF SUPEROXIDE GENERATION
Document Type and Number:
WIPO Patent Application WO/1993/010087
Kind Code:
A1
Abstract:
The present invention relates to compounds of formula (I) and the pharmaceutically acceptable salts thereof wherein R1, R2 and R10 are the same or different and independently represent alkyl, alkoxy, hydroxy, phenyl, halogen, trifluoromethyl, cyano, or hydrogen; q is 0 or 1; R3 represents hydrogen, alkyl, alkoxy, or hydroxy; X represents O, S or (CH2)m wherein m is an integer from 0 to 4; A represents O or S(O)n wherein n is 0, 1, or 2; Alk1 is straight or branched chain alkyl having 1 to 6 carbon atoms; p is 0 or 1; and R represents: (a) alkyl; (b) OH; (c) OR4 wherein R4 is alkyl of 1 to 6 carbon atoms; (d) NR5R6 wherein R5 is hydrogen or alkyl, and R6 is hydrogen, alkyl, alkoxyalkyl, heterocyclealkyl, substituted heterocyclealkyl, cycloalkyl, substituted cycloalkyl, phenyl, substituted phenyl, phenylalkyl, substituted phenylalkyl, or Alk-NR8R9 wherein Alk is alkyl of 1 to 10 carbon atoms and R8 and R9 each independently are hydrogen or alkyl; or NR5R6 together form a heterocyclic ring which may optionally be substituted; or (e) (CH2)tCOOR7 wherein t is an integer from 1 to 4 and r7 is hydrogen or alkyl of 1 to 4 carbon atoms. The compounds are inhibitors or stimulators of superoxide generation.
Inventors:
MUELLER RICHARD AUGUST (US)
PARTIS RICHARD ALLEN (US)
PARTIS RICHARD ALLEN (US)
Application Number:
PCT/US1992/009560
Publication Date:
May 27, 1993
Filing Date:
November 17, 1992
Export Citation:
Assignee:
SEARLE & CO (US)
International Classes:
C07D333/34; A61K31/34; A61K31/341; A61K31/38; A61K31/381; A61K31/44; A61K31/4402; A61K31/4406; A61K31/4409; A61K31/4418; A61K31/445; A61K31/451; A61P9/12; A61P11/08; A61P29/00; A61P37/08; A61P43/00; C07C317/20; C07C317/44; C07C323/17; C07C323/20; C07C323/22; C07C323/52; C07C323/60; C07C323/65; C07D211/14; C07D213/40; C07D213/56; C07D307/18; C07D307/20; C07D307/32; C07D493/04; (IPC1-7): A61K31/10; C07C323/17; C07C323/22; C07C323/52; C07C323/60; C07D213/40; C07D307/20
Foreign References:
| US5064860A | 1991-11-12 | |||
| EP0512559A1 | 1992-11-11 |
Other References:
JOURNAL OF ORGANIC CHEMISTRY. vol. 39, no. 6, 22 May 1974, EASTON US pages 807 - 811 F.A. DAVIS ET AL. 'Chemistry of the Sulfur-Nitrogen Bond. VII. Rearrangementof Sulenimines (S-Aryl Thiooximes) to B-Ketosulfides. Attempted Synthesis of Benzo[b]thiophenes'
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. vol. 100, no. 22, 25 October 1978, GASTON, PA US pages 7103 - 7106 B.M. TROST ET AL. 'Hydroxysulfenylation of Olefins. An Olefin Cleavage with Functional Group Differentiation'
SYNTHESIS. no. 2, February 1987, STUTTGART DE pages 159 - 161 J.-H. YOUN ET AL. 'Synthesis of Enantiomerically Enriched a-Sulfenylated Ketones and Aldehydes'
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. vol. 100, no. 22, 25 October 1978, GASTON, PA US pages 7103 - 7106 B.M. TROST ET AL. 'Hydroxysulfenylation of Olefins. An Olefin Cleavage with Functional Group Differentiation'
SYNTHESIS. no. 2, February 1987, STUTTGART DE pages 159 - 161 J.-H. YOUN ET AL. 'Synthesis of Enantiomerically Enriched a-Sulfenylated Ketones and Aldehydes'
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