US4978757A
Expired / Lapsed
US
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1,2,8,8a-tetrahydrocyclopropa (C) pyrrolo [3,2-e)]-indol-4(5H)-ones and related compounds
Assignee: Pharmacia and Upjohn Co
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Filing: 1989-11-30
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Granted: 1990-12-18
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Expires: 2009-11-30
Abstract
Abstract 1,2,8,8a-Tetrahydrocyclopropa[3]pyrrolo(3,2-e)indol-4(5H)-ones, and related compounds of formulas I and intermediate therefor II ##STR1## wherein R 2 , R 2 ', R 3 , R 5 , R 50 and X are as defined in the specification, e.g., (7bR,8aS)-1,2,8,8a -tetrahydro-7-methyl-2-[[5-(((1H-indol-2-yl)carbonyl)amino)-1H-indol-2-yl]carbonyl]cyclopropa[pyrrolo[3,2-e]indol-4(5H)-one (U-71,184), as purified, and its racemic form (U-68,415), and related compounds, are useful as ultraviolet light absorbers and as antibacterials. The lead compounds are useful as antitumor drug compounds in standard laboratory animal tests.
Inventors
- 👤 Robert C. Kelly
- 👤 Martha A. Warpehoski
- 👤 Wendell Wierenga
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 16:42
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/02; C07D498/04; C07D498/10; C07D519/00
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
230 words
A compound selected from the group consisting of wherein R 1 is CH 3 --, --CH 2 Ph, CH 2 --CHCH 2 --, --CH 2 SCH 3 , --CH 2 OCH 3 , --CH 2 OCH 2 CH 2 OCH 3 , --CH 2 CCl 3 , --CH 2 CH 2 Si(R 2 ) 3 , or H, where Ph is phenyl; R 2 is alkyl(C 1 -C 5 ), phenyl, or H; R 2 ' is alkyl(C 1 -C 5 ), phenyl, or H; R 2 ' is alkyl(C 1 -C 5 ), phenyl, or H; R 3 is alkyl(C 1 -C 5 ), phenyl, or H; X is Cl, Br, or I; or OSO 2 R 40 where R 40 is alkyl(C 1 -C 5 ), phenyl, tolyl, bromophenyl, nitrophenyl, or trifluoromethyl; R 50 is hydrogen or the same as R 5 ; R 5 is a carbonyl acyl group selected from the group consisting of ##STR35## where R 6 is H, -alkyl(C 1 -C 20 ), --CCl 3 , CF 3 , or NH 2 ; ##STR36## where X 1 and/or X 2 is H, CH 3 , OH, OCH 3 , NO 2 , NH 2 , NNHAc, NHBz, or halogen; ##STR37## wherein n 1 =2-12; ##STR38## where X 7 =--O-- or --NH--; R 11 =--CH 2 CH 2 -- or --CH═CH-- and n 4 =1-4.
Claim 2
Dependent Claim
230 words
A compound selected from the group consisting of wherein R 1 is CH 3 --, --CH 2 Ph, CH 2 --CHCH 2 --, --CH 2 SCH 3 , --CH 2 OCH 3 , --CH 2 OCH 2 CH 2 OCH 3 , --CH 2 CCl 3 , --CH 2 CH 2 Si(R 2 ) 3 , or H, where Ph is phenyl; R 2 is alkyl(C 1 -C 5 ), phenyl, or H; R 2 ' is alkyl(C 1 -C 5 ), phenyl, or H; R 2 ' is alkyl(C 1 -C 5 ), phenyl, or H; R 3 is alkyl(C 1 -C 5 ), phenyl, or H; X is Cl, Br, or I; or OSO 2 R 40 where R 40 is alkyl(C 1 -C 5 ), phenyl, tolyl, bromophenyl, nitrophenyl, or trifluoromethyl; R 50 is hydrogen or the same as R 5 ; R 5 is a carbonyl acyl group selected from the group consisting of ##STR35## where R 6 is H, -alkyl(C 1 -C 20 ), --CCl 3 , CF 3 , or NH 2 ; ##STR36## where X 1 and/or X 2 is H, CH 3 , OH, OCH 3 , NO 2 , NH 2 , NNHAc, NHBz, or halogen; ##STR37## wherein n 1 =2-12; ##STR38## where X 7 =--O-- or --NH--; R 11 =--CH 2 CH 2 -- or --CH═CH-- and n 4 =1-4.
Claim 3
Dependent Claim
10 words
A compound of the formula ##STR39## according to claim 1.
Claim 4
Dependent Claim
10 words
A compound of the formula ##STR40## according to claim 1.
Claim 5
Dependent Claim
13 words
A compound according to claim 1 selected from the group consisting of ##STR41##
References Cited (Backward Citations)
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