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US4912227A Expired / Lapsed US ⏱️ 0.0 years remaining

1,2,8,8A-tetrahydrocyclopropa(c)pyrrolo(3,2-e)-indol-4-(5H)-ones and related compounds

Assignee: Pharmacia and Upjohn Co
•
Filing: 1986-08-07
•
Granted: 1990-03-27
•
Expires: 2006-08-07
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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 2026-10-31 23:16
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/02; C07D498/10; C07D498/04; C07D519/00

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 329 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 O-- CH 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 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 (vii) ##STR48## where n 2 is 0-3; and R 8 is H, CH 3 or C 2 H 5 ; (Viii) ##STR49## where X 5 is H, OH, OCH 3 , --NO 2 , --NH 2 , ##STR50## --NH--CN and R 8 has the meaning defined above; (ix) ##STR51## where n 3 is 1, 2, or 3; and R 8 , R 5 and X 5 have the meanings defined above; (x) ##STR52## where X 6 is H, NO 2 , NH 2 , ##STR53## (xi) ##STR54## where R 9 is CH 3 or NH 2 (xii) ##STR55## where R 8 and R 9 have the meanings defined above; (xiii) ##STR56## (xvii) ##STR57## where X 8 is --O--, --S--, NH; X 9 is --CH-- and X 5 has the meaning defined above; (xxii) ##STR58## where X 6 and R 8 have the meanings defined above; (xxiii) ##STR59## and when either of X 5 or X 6 is --OH or --NH 2 , then each of the above R 5 groups may be coupled with other groups to denote the following structures: ##STR60##
Claim 2
Dependent Claim 329 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 O-- CH 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 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 (vii) ##STR48## where n 2 is 0-3; and R 8 is H, CH 3 or C 2 H 5 ; (Viii) ##STR49## where X 5 is H, OH, OCH 3 , --NO 2 , --NH 2 , ##STR50## --NH--CN and R 8 has the meaning defined above; (ix) ##STR51## where n 3 is 1, 2, or 3; and R 8 , R 5 and X 5 have the meanings defined above; (x) ##STR52## where X 6 is H, NO 2 , NH 2 , ##STR53## (xi) ##STR54## where R 9 is CH 3 or NH 2 (xii) ##STR55## where R 8 and R 9 have the meanings defined above; (xiii) ##STR56## (xvii) ##STR57## where X 8 is --O--, --S--, NH; X 9 is --CH-- and X 5 has the meaning defined above; (xxii) ##STR58## where X 6 and R 8 have the meanings defined above; (xxiii) ##STR59## and when either of X 5 or X 6 is --OH or --NH 2 , then each of the above R 5 groups may be coupled with other groups to denote the following structures: ##STR60##
Claim 3
Dependent Claim 10 words
A compound of the formula ##STR61## according to claim 1.
Claim 4
Dependent Claim 10 words
A compound of the formula ##STR62## according to claim 1.
Claim 5
Dependent Claim 10 words
A compound of the formula ##STR63## according to claim 1.
Claim 6
Dependent Claim 10 words
A compound of the formula ##STR64## according to claim 1.
Claim 7
Dependent Claim 10 words
A compound of the formula ##STR65## according to claim 1.
Claim 8
Dependent Claim 10 words
A compound of the formula ##STR66## according to claim 1.
Claim 9
Dependent Claim 10 words
A compound of the formula ##STR67## according to claim 1.
Claim 10
Dependent Claim 10 words
A compound of the formula ##STR68## according to claim 1.
Claim 11
Dependent Claim 10 words
A compound of the formula ##STR69## according to claim 1.
Claim 12
Dependent Claim 10 words
A compound of the formula ##STR70## according to claim 1.
Claim 13
Dependent Claim 10 words
A compound of the formula ##STR71## according to claim 1.
Claim 14
Dependent Claim 10 words
A compound of the formula ##STR72## according to claim 1.
Claim 15
Dependent Claim 13 words
A compound according to claim 1 selected from the group consisting of ##STR73##
Claim 16
Dependent Claim 12 words
A compound according to claim 14, formula (h) which is (7bR, 8aS)-1,2,8,8a-tetrahydro-7-methyl-2-[[5-(((2H-indol-2-yl)carbonyl)amino)-1H-indol-2-yl]carbonyl]cyclopropa[pyrrolo[3,2-e]indol-4(5H)-one.
Claim 17
Dependent Claim 45 words
A compound according to claim 1 having the formula wherein R 5 is the dimer combination xvii+xvii bound together with the amide linkage and having the formula ##STR74## and R 2 , R 2 ' and R 3 are the same as in claim 1.
Claim 18
Dependent Claim 25 words
A compound of claim 16 wherein R 2 is (C 1 to C 5 )alkyl, R 2 ' is hydrogen and R 3 is hydrogen.
Claim 19
Dependent Claim 11 words
A compound of claim 17 wherein R 2 is methyl, (7bR,8aS)-1,2,8,8a-tetrahydro-7-methyl-2-[[5-(((2H-benzofuran-2-yl)carbonyl)-amino)-1H-indol-2-yl]carbonyl]-cyclopropra]pyrrolo[3,2-e]indol-4(5H)-one

References Cited (Backward Citations)

US4169888A Cited
US4423229A Cited
US4423230A Cited
US4423228A Cited
US4424365A Cited
US4440518A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-03-26 1993-09-25 1994-03-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-03-26 1997-09-25 1998-03-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-03-26 2001-09-25 2002-03-27 $7700.00 Window Closed / Lapsed

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