US5284868A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pharmaceutical compounds
Assignee: Lilly Industries Ltd
•
Filing: 1992-09-25
•
Granted: 1994-02-08
•
Expires: 2012-09-25
Abstract
Abstract A pharmaceutical compound of the formula ##STR1## in which n is 0, 1 or 2 and R 1 is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R 1 is halo, trifluoromethyl, C 1-4 alkoxy, hydroxy, nitro, C 1-4 alkyl, C 1-4 alkylthio, hydroxy-C 1-4 alkyl, hydroxy-C 1-4 alkoxy, trifluoromethoxy, carboxy, --COOR 5 where R 5 is an ester group, --CONR 6 R 7 or --NR 6 R 7 where R 6 and R 7 are each hydrogen or C 1-4 alkyl; R 2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R 2 is furanyl optionally substituted with C 1-4 alkyl; R 3 is nitrile, carboxy, --COOR 8 where R 8 is an ester group, --CONR 9 R 10 where R 9 and R 10 are each hydrogen or C 1-4 alkyl, or R 11 SO 2 -- where R 11 is C 1-4 alkyl or optionally substituted phenyl; and R 4 is --NR 12 R 13 , --NHCOR 12 , --N(COR 12 ) 2 or --N═CHOCH 2 R 12 where R 12 and R 13 are each hydrogen or C 1-4 alkyl optionally substituted with carboxy, ##STR2## where X is C 2-4 alkylene, or --NHSO 2 R 14 where R 14 is C 1-4 alkyl or optionally substituted phenyl; provided that when n is 0, R 3 is nitrile and R 4 is --NH 2 , R 2 is not phenyl or phenyl substituted in the para-position with a single chloro, hydroxy or methoxy substituent; and salts thereof.
Inventors
- 👤 Colin P. Dell
- 👤 Jai P. Singh
- 👤 Colin W. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 10:28
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; C07D311/00; C07D311/02; C07D311/78; C07D311/80; A; A61; A61K; A61K31/00; A61K31/33; A61K31/335; A61K31/35; A61P; A61P1/00; A61P1/16; A61P19/00; A61P19/02; A61P29/00; A61P3/00; A61P3/08; A61P3/10; A61P35/00; A61P37/00; A61P37/02; A61P37/06; A61P9/00; A61P9/10; C07D311/92
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
271 words
A compound of the formula ##STR10## in which n is 0, 1 or 2 and R 1 is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R 1 is halo, trifluoromethyl, C 1-4 alkoxy, hydroxy, nitro, C 1-4 alkyl, C 1-4 alkylthio, hydroxy-C 1-4 alkyl, hydroxy-C 1-4 alkoxy, trifluoromethoxy, carboxy, --COOR 5 where R 5 is an ester group, --CONR 6 R 7 or --NR 6 R 7 where R 6 and R 7 are each hydrogen or C 1-4 alkyl; R 2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R 2 is furanyl optionally substituted with C 1-4 alkyl; R 3 is nitrile, carboxy, --COOR 8 where R 8 is an ester group, --CONR 9 R 10 where R 9 and R 10 are each hydrogen or C 1-4 alkyl, or R 11 SO 2 -- where R 11 is C 1-4 alkyl or optionally substituted phenyl; and R 4 is --NR 12 R 13 , --NHCOR 12 , --N(COR 12 ) 2 or --N═CHOR 12 where R 12 and R 13 are each hydrogen or C 1-4 alkyl optionally substituted with carboxy, ##STR11## where X is C 2-4 alkylene, or --NHSO 2 R 14 where R 14 is C 1-4 alkyl or optionally substituted phenyl; provided that when n is 0, R 3 is nitrile and R 4 is --NH 2 , R 2 is not phenyl or phenyl substituted in the para-position with a single chloro, hydroxy or methoxy substituent; or a salt thereof.
Claim 2
Dependent Claim
271 words
A compound of the formula ##STR10## in which n is 0, 1 or 2 and R 1 is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R 1 is halo, trifluoromethyl, C 1-4 alkoxy, hydroxy, nitro, C 1-4 alkyl, C 1-4 alkylthio, hydroxy-C 1-4 alkyl, hydroxy-C 1-4 alkoxy, trifluoromethoxy, carboxy, --COOR 5 where R 5 is an ester group, --CONR 6 R 7 or --NR 6 R 7 where R 6 and R 7 are each hydrogen or C 1-4 alkyl; R 2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R 2 is furanyl optionally substituted with C 1-4 alkyl; R 3 is nitrile, carboxy, --COOR 8 where R 8 is an ester group, --CONR 9 R 10 where R 9 and R 10 are each hydrogen or C 1-4 alkyl, or R 11 SO 2 -- where R 11 is C 1-4 alkyl or optionally substituted phenyl; and R 4 is --NR 12 R 13 , --NHCOR 12 , --N(COR 12 ) 2 or --N═CHOR 12 where R 12 and R 13 are each hydrogen or C 1-4 alkyl optionally substituted with carboxy, ##STR11## where X is C 2-4 alkylene, or --NHSO 2 R 14 where R 14 is C 1-4 alkyl or optionally substituted phenyl; provided that when n is 0, R 3 is nitrile and R 4 is --NH 2 , R 2 is not phenyl or phenyl substituted in the para-position with a single chloro, hydroxy or methoxy substituent; or a salt thereof.
Claim 3
Dependent Claim
210 words
A compound according to claim 1 in which n is 0, 1 or 2 and R 1 is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R 1 is halo, trifluoromethyl or C 1-4 alkoxy, R 2 is phenyl, naphthyl or heteroaryl optionally substituted with one or two substituents each selected from nitro, trifluoromethyl, halo, C 1-4 alkyl and C 1-4 alkoxy or R 2 is furanyl optionally substituted with C 1-4 alkyl, R 3 is nitrile, carboxy, --COOR 8 where R 8 is an ester group, or --CONR 9 R 10 where R 9 and R 10 are each hydrogen or C 1-4 alkyl, and R 4 is --NR 12 R 13 , --NHCOR 12 or --N(COR 12 ) 2 where R 12 and R 13 are each hydrogen or C 1-4 alkyl, or --NHSO 2 R 14 where R 14 is C 1-4 alkyl or phenyl optionally substituted with one to three substituents each selected from C 1-4 alkyl, C 1-4 alkoxy, nitro and halo; provided that when n is 0, R 3 is nitrile and R 4 is --NH 2 , R 2 is not phenyl or phenyl substituted in the para-position with a single chloro, hydroxy or methoxy substituent.
Claim 4
Dependent Claim
22 words
A compound according to claim 1 in which n is 0 or 1 and R 1 is C 1-4 alkoxy or halo.
Claim 5
Dependent Claim
73 words
A compound according to claim 3 in which R 2 is phenyl optionally substituted with one or two substituents selected from halo, trifluoromethyl, C 1-4 alkoxy, hydroxy, nitro, C 1-4 alkyl, C 1-4 alkylthio, hydroxy-C 1-4 alkyl, hydroxy-C 1-4 alkoxy, trifluoromethoxy, carboxy, --COOR 15 where R 15 is an ester group, --CONR 16 R 17 or --NR 16 R 17 where R 16 and R 17 are each hydrogen or C 1-4 alkyl.
Claim 6
Dependent Claim
12 words
A compound according to claim 4 in which R 3 is nitrile.
Claim 7
Dependent Claim
14 words
A compound according to claim 5 in which R 4 is --NH 2 .
Claim 8
Dependent Claim
23 words
A pharmaceutical formulation comprising a compound according to claim 1, or a pharmaceutically-acceptable salt thereof, together with a pharmaceutically-acceptable diluent or carrier therefor.
Claim 9
Dependent Claim
39 words
A method of treating an immune disease or a disease in which excess cell proliferation or enzyme release occur, which comprises administering to a patient in need of treatment a therapeutic dosage of a compound according to claim 1.
Claim 10
Dependent Claim
24 words
A method of treating restenosis, which comprises administering to a patient in need of treatment a therapeutic dosage of a compound of claim 1.
Claim 11
Dependent Claim
12 words
The method of claim 9 wherein said administration is by local delivery.
Claim 12
Dependent Claim
17 words
The method of claim 10 where the local delivery is by means of a local delivery catheter.
Claim 13
Dependent Claim
17 words
The method of claim 10 where the local delivery is by means of a site specific carrier.
Claim 14
Dependent Claim
14 words
The method of claim 10 wherein said administration is by a membrane anchored linker.
Claim 15
Dependent Claim
17 words
The method of use of claim 10 where the local delivery is by means of an implant.
Claim 16
Dependent Claim
28 words
A method of inhibiting vascular smooth muscle cell proliferation, which comprises administering to a patient in need of treatment a therapeutic dosage of a compound of claim 1.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-02-07 | 1997-08-09 | 1998-02-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-02-07 | 2001-08-09 | 2002-02-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-02-07 | 2005-08-09 | 2006-02-08 | $7700.00 | Window Closed / Lapsed |