US4654360A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1,2,3-trisubstituted indoles for treatment of inflammation
Assignee: Syntex USA LLC
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Filing: 1984-06-01
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Granted: 1987-03-31
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Expires: 2004-06-01
Abstract
Abstract Disclosed are compounds of the formula ##STR1## wherein the several groups are defined herein. These compounds are useful for treating inflammation.
Inventors
- 👤 Robert J. Greenhouse
- 👤 Joseph M. Muchowski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:16
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/40
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
192 words
A compound of the formula: ##STR5## wherein R is alkyl of 1 to 8 carbon atoms, benzyl or benzyl substituted with one or more groups independently selected from the group consisting of alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 , --SCN, and --OCH 2 O-- attached at adjacent carbon atoms, which is methylenedioxy; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; Y is S, NH, or NR 2 ; n is 2, 3, 4, 5, 6, 7, or 8; m is 0, 1 or 2; X and Z are independently alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 or --SCN; p is 0, 1, 2, 3, 4, or 5; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
192 words
A compound of the formula: ##STR5## wherein R is alkyl of 1 to 8 carbon atoms, benzyl or benzyl substituted with one or more groups independently selected from the group consisting of alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 , --SCN, and --OCH 2 O-- attached at adjacent carbon atoms, which is methylenedioxy; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; Y is S, NH, or NR 2 ; n is 2, 3, 4, 5, 6, 7, or 8; m is 0, 1 or 2; X and Z are independently alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 or --SCN; p is 0, 1, 2, 3, 4, or 5; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein Y is S.
Claim 4
Dependent Claim
16 words
A compound of claim 2 wherein n is 2, m is 2 and Z is hydrogen.
Claim 5
Dependent Claim
13 words
A compound according to claim 3 wherein R is benzyl or substituted benzyl.
Claim 6
Dependent Claim
15 words
A compound according to claim 4 which is 1-benzyl-2-aminoethylthio-3-phenylsulfonylindole or an acid addition salt thereof.
Claim 7
Dependent Claim
15 words
A compound according to claim 4 which is 1-(2-methoxycarbonylbenzyl)-2-aminoethylthio-3-phenylsulfonylindole or an acid addition salt thereof.
Claim 8
Dependent Claim
17 words
A compound according to claim 4 which is 1-(4-chlorobenzyl)-2-aminoethylthio-3-phenylsulfonylindole or a pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
17 words
A compound according to claim 4 which is 1-(-4-methylbenzyl)-2-aminoethylthio-3-phenylsulfonylindole or a pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
17 words
A compound according to claim 4 which is 1-benzyl-2-aminoethylthio-3-(4-methylphenylsulfonyl)indole or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
17 words
A compound according to claim 4 which is 1-benzyl-2-aminoethylthio-3-(4-chlorophenylsulfonyl)indole or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Independent Claim
211 words
A method for treating inflammation, which method comprises administering either alone or in admixture with a pharmaceutically acceptable excipient, a compound of the formula ##STR6## wherein R is alkyl of 1 to 8 carbon atoms, benzyl or benzyl substituted with one or more groups independently selected from the group consisting of alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 , CH 3 --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 , --SCN and --OCH 2 O-- attached at adjacent carbon atoms, which is methylenedioxy; R 1 is independently hydrogen or alkyl of 1 to 4 carbon atoms; Y is SO, NH, or NR 2 ; n is 2, 3, 4, 5, 6, 7, 8; m is 0, 1 or 2; X and Z are independently alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 or --SCN; p is 0, 1, 2, 3, 4 or 5; or a pharmaceutically acceptable salt thereof.
Claim 13
Independent Claim
211 words
A method for treating inflammation, which method comprises administering either alone or in admixture with a pharmaceutically acceptable excipient, a compound of the formula ##STR6## wherein R is alkyl of 1 to 8 carbon atoms, benzyl or benzyl substituted with one or more groups independently selected from the group consisting of alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 , CH 3 --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 , --SCN and --OCH 2 O-- attached at adjacent carbon atoms, which is methylenedioxy; R 1 is independently hydrogen or alkyl of 1 to 4 carbon atoms; Y is SO, NH, or NR 2 ; n is 2, 3, 4, 5, 6, 7, 8; m is 0, 1 or 2; X and Z are independently alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 or --SCN; p is 0, 1, 2, 3, 4 or 5; or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
9 words
The method of claim 11 wherein Y is S.
Claim 15
Dependent Claim
16 words
The method of claim 11 wherein n is 2, m is 2 and Z is hydrogen.
Claim 16
Dependent Claim
12 words
The method of claim 11 wherein R is benzyl or substituted benzyl.
Claim 17
Dependent Claim
20 words
The method of claim 11 in which the compound to be administered is 1-(2-methoxycarbonylbenzyl)-2-aminoethylthio-3-phenylsulfonylindole or an acid addition salt thereof.
Claim 18
Dependent Claim
22 words
The method of claim 11 in which the compound to be administered is 1-(4-chlorobenzyl)-2-aminoethylthio-3-phenylsulfonylindole or a pharmaceutically acceptable acid addition salt thereof.
Claim 19
Dependent Claim
22 words
The method of claim 11 in which the compound to be administered is 1-(-4-methylbenzyl)-2-aminoethylthio-3-phenylsulfonylindole or a pharmaceutically acceptable acid addition salt thereof.
Claim 20
Dependent Claim
22 words
The method of claim 11 in which the compound to be administered is 1-benzyl-2-aminoethylthio-3-(4-methylphenylsulfonyl)indole or a pharmaceutically acceptable acid addition salt thereof.
Claim 21
Dependent Claim
168 words
A compound of the formula: ##STR7## wherein R is alkyl of 1 to 8 carbon atoms, benzyl or benzyl substituted with one or more groups independently selected from the group consisting of alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 , --SCN, and --OCH 2 O-- attached at adjacent carbon atoms, which is methylenedioxy; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms m is 0, 1 or 2; X and Z are independently alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 or --SCN; p is 0, 1, 2, 3, 4, or 5.
Claim 22
Dependent Claim
168 words
A compound of the formula: ##STR7## wherein R is alkyl of 1 to 8 carbon atoms, benzyl or benzyl substituted with one or more groups independently selected from the group consisting of alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 , --SCN, and --OCH 2 O-- attached at adjacent carbon atoms, which is methylenedioxy; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms m is 0, 1 or 2; X and Z are independently alkyl of 1 to 4 carbon atoms, halo, hydroxy, --OR 2 where R 2 is alkyl of 1 to 4 carbon atoms, --OCF 3 , --SO 2 CH 3 , --CO 2 H, --CO 2 R 2 , --CHO, --NO 2 , --CF 3 or --SCN; p is 0, 1, 2, 3, 4, or 5.
Claim 23
Dependent Claim
9 words
A compound according to claim 19 which is 1-benzyl-2-chloro-3-phenylsulfosulfonylindole.
Claim 24
Dependent Claim
9 words
A compound according to claim 19 which is 1-benzyl-2-chloro-3-(4-methylphenylsulfonyl)indole.
Claim 25
Dependent Claim
9 words
A compound according to claim 19 which is 1-benzyl-2-chloro-3-(4-chlorphenylsulfonyl)indole.
Claim 26
Dependent Claim
9 words
A compound according to claim 19 which is 1-(4-chlorobenzyl)-2-chloro-3-phenylsulfonylindole.
Claim 27
Dependent Claim
9 words
A compound according to claim 19 which is 1-(2-methylcarbonylbenzyl)-2-chloro-3-phenylsulfonylindole.
Claim 28
Dependent Claim
9 words
A compound according to claim 19 which is 1-(4-methylbenzyl)-2-chloro-3-phenylsulfonylindole.
Claim 29
Dependent Claim
22 words
The method of claim 11 in which the compound to be administered is 1-benzyl-2-aminoethylthio-3-(4-chlorophenylsulfonyl)indole or a pharmaceutically acceptable acid addition salt thereof.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-03-30 | 1990-09-29 | 1991-03-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-03-30 | 1994-09-29 | 1995-03-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-03-30 | 1998-09-29 | 1999-03-31 | $7700.00 | Window Closed / Lapsed |