Patent US1568838A successfully refreshed from Google Patents.
US4873259A
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Indole, benzofuran, benzothiophene containing lipoxygenase inhibiting compounds
Assignee: Abbott Laboratories
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Filing: 1988-01-11
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Granted: 1989-10-10
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Expires: 2008-01-11
Abstract
Abstract Compounds of the formula: ##STR1## wherein R 1 is (1) hydrogen, (2) C 1 to C 4 alkyl, (3) C 2 to C 4 alkenyl, or (4) NR 2 R 3 , wherein R 2 and R 3 are independently selected from (1) hydrogen, (2) C 1 to C 4 alkyl and (3) hydroxyl, but R 2 and R 3 are not simultaneously hydroxyl; wherein X is oxygen, sulfur, SO 2 , or NR 4 , wherein R 4 is (1) hydrogen, (2) C 1 to C 6 alkyl, (3) C 1 to C 6 alkoyl, (4) aroyl, or (5) alkylsulfonyl; A is selected from C 1 to C 6 alkylene and C 2 to C 6 alkenylene; n is 1-5; Y is selected independently at each occurrence from (1) hydrogen, (2) halogen, (3) hydroxy, (4) cyano, (5) halosubstituted alkyl, (6) C 1 to C 12 alkyl, (7) C 2 to C 12 alkenyl, (8) C 1 to C 12 alkoxy, (9) C 3 to C 8 cycloalkyl, (10) C 1 -C 8 thioalkyl, (11) aryl, (12) aryloxy, (13) aroyl, (14) C 1 to C 12 arylalkyl, (15) C 2 to C 12 arylalkenyl, (16) C 1 to C 12 arylalkoxy, (17) C 1 to C 12 arylthioalkoxy, and substituted derivatives of (18) aryl, (19) aryloxy, (20) aroyl, (21) C 1 to C 12 arylalkyl, (22) C 2 to C 12 arylalkenyl, (23) C 1 to C 12 arylalkoxy, or (24) C 1 to C 12 arylthioalkoxy, wherein substituents are selected from halo, nitro, cyano, C 1 to C 12 alkyl, alkoxy, and halosubstituted alkyl; Z is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C 1 to C 12 alkoyl, are potent inhibitors of 5- and/or 12-lipoxygenase enzymes. Also disclosed are lipoxygenase inhibiting compositions and a method for inhibiting lipoxygenase activity.
Inventors
- 👤 James B. Summers, Jr.
- 👤 Bruce P. Gunn
- 👤 Dee W. Brooks
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 01:18
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/58; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/14; C07D307/00; C07D307/77; C07D307/78; C07D307/79; C07D307/81
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
287 words
A compound of the formula: ##STR11## wherein R 1 is (1) hydrogen, (2) C 1 to C 4 alkyl, (3) C 2 to C 4 alkenyl, or (4) NR 2 R 3 , wherein R 2 and R 3 are independently selected from (1) hydrogen, (2) C 1 to C 4 alkyl and (3) hydroxyl, but R 2 and R 3 are not simultaneously hydroxyl; wherein X is oxygen, sulfur, SO 2 , or NR 4 , wherein R 4 is (1) hydrogen, (2) C 1 to C 6 alkyl, (3) C 1 to C 6 alkoyl, (4) aroyl, or (5) alkylsulfonyl; A is selected from C 1 to C 6 alkylene and C 2 to C 6 alkenylene; n is 1-5; Y is selected independently at each occurrence from (1) hydrogen, (2) halogen, (3) hydroxy, (4) cyano, (5) halosubstituted alkyl, (6) C 1 to C 12 alkyl, (7) C 2 to C 12 alkenyl, (8) C 1 to C 12 alkoxy, (9) C 3 to C 8 cycloalkyl, (10) C 1 -C 8 thioalkyl, (11) aryl, (12) aryloxy, (13) aroyl, (14) C 1 to C 12 arylalkyl, (15) C 2 to C 12 arylalkenyl, (16) C 1 to C 12 arylalkoxy, (17) C 1 to C 12 arylthioalkoxy, and substituted derivatives of (18) aryl, (19) aryloxy, (20) aroyl, (21) C 1 to C 12 arylalkyl, (22) C 2 to C 12 arylalkenyl, (23) C 1 to C 12 arylalkoxy, or (24) C 1 to C 12 arylthioalkoxy, wherein substituents are selected from halo, nitro, cyano, C 1 to C 12 alkyl, alkoxy, and halosubstituted alkyl; Z is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C 1 to C 12 alkoyl.
Claim 2
Dependent Claim
287 words
A compound of the formula: ##STR11## wherein R 1 is (1) hydrogen, (2) C 1 to C 4 alkyl, (3) C 2 to C 4 alkenyl, or (4) NR 2 R 3 , wherein R 2 and R 3 are independently selected from (1) hydrogen, (2) C 1 to C 4 alkyl and (3) hydroxyl, but R 2 and R 3 are not simultaneously hydroxyl; wherein X is oxygen, sulfur, SO 2 , or NR 4 , wherein R 4 is (1) hydrogen, (2) C 1 to C 6 alkyl, (3) C 1 to C 6 alkoyl, (4) aroyl, or (5) alkylsulfonyl; A is selected from C 1 to C 6 alkylene and C 2 to C 6 alkenylene; n is 1-5; Y is selected independently at each occurrence from (1) hydrogen, (2) halogen, (3) hydroxy, (4) cyano, (5) halosubstituted alkyl, (6) C 1 to C 12 alkyl, (7) C 2 to C 12 alkenyl, (8) C 1 to C 12 alkoxy, (9) C 3 to C 8 cycloalkyl, (10) C 1 -C 8 thioalkyl, (11) aryl, (12) aryloxy, (13) aroyl, (14) C 1 to C 12 arylalkyl, (15) C 2 to C 12 arylalkenyl, (16) C 1 to C 12 arylalkoxy, (17) C 1 to C 12 arylthioalkoxy, and substituted derivatives of (18) aryl, (19) aryloxy, (20) aroyl, (21) C 1 to C 12 arylalkyl, (22) C 2 to C 12 arylalkenyl, (23) C 1 to C 12 arylalkoxy, or (24) C 1 to C 12 arylthioalkoxy, wherein substituents are selected from halo, nitro, cyano, C 1 to C 12 alkyl, alkoxy, and halosubstituted alkyl; Z is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C 1 to C 12 alkoyl.
Claim 3
Dependent Claim
71 words
A compound of claim 1 having the formula: ##STR12## wherein R 5 is C 1 or C 2 alkyl, or NR 6 R 7 where R 6 and R 7 are independently selected from hydrogen and C 1 or C 2 alkyl; B is CH 2 or CHCH 3 ; W is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C 1 to C 12 alkoyl.
Claim 4
Dependent Claim
13 words
A compound according to claim 1 wherein R 1 is CH 3 .
Claim 5
Dependent Claim
13 words
A compound according to claim 1 wherein R 1 is NH 2 .
Claim 6
Dependent Claim
13 words
A compound according to claim 1 wherein R 1 is NHCH 3 .
Claim 7
Dependent Claim
12 words
A compound according to claim 1 wherein A is --CHCH 3 --.
Claim 8
Dependent Claim
12 words
A compound according to claim 1 wherein A is --CH 2 --.
Claim 9
Dependent Claim
10 words
A compound according to claim 1 wherein X is sulfur.
Claim 10
Dependent Claim
10 words
A compound according to claim 1 wherein X is oxygen.
Claim 11
Dependent Claim
9 words
The compound of claim 1 having the formula: ##STR13##
Claim 12
Dependent Claim
9 words
The compound of claim 1 having the formula: ##STR14##
Claim 13
Dependent Claim
9 words
The compound of claim 1 having the formula: ##STR15##
Claim 14
Dependent Claim
31 words
A method for inhibiting 5- and/or 12-lipoxygenase activity in a mammal in need of such treatment, comprising administering to the mammal a therapeutically effective amount of a compound of claim 1.
Claim 15
Dependent Claim
68 words
The method of claim 13 wherein the compound has the formula: ##STR16## wherein R 5 is C 1 or C 2 alkyl, or NR 6 R 7 are independently selected from hydrogen and C 1 or C 2 alkyl; B is CH 2 or CHCH 3 ; W is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C 1 to C 12 alkoyl.
Claim 16
Dependent Claim
12 words
The method of claim 13 wherein R 1 is CH 3 .
Claim 17
Dependent Claim
12 words
The method of claim 13 wherein R 1 is NH 2 .
Claim 18
Dependent Claim
12 words
The method of claim 13 wherein R 1 is NHCH 3 .
Claim 19
Dependent Claim
11 words
The method of claim 13 wherein A is --CHCH 3 --.
Claim 20
Dependent Claim
11 words
The method of claim 13 wherein A is --CH 2 --.
Claim 21
Dependent Claim
9 words
The method of claim 13 wherein X is sulfur.
Claim 22
Dependent Claim
9 words
The method of claim 13 wherein X is oxygen.
Claim 23
Dependent Claim
12 words
The method of claim 13 wherein the compound has the formula: ##STR17##
Claim 24
Dependent Claim
12 words
The method of claim 13 wherein the compound has the formula: ##STR18##
Claim 25
Dependent Claim
12 words
The method of claim 13 wherein the compound has the formula: ##STR19##
Claim 26
Dependent Claim
23 words
A pharmaceutical composition for inhibiting 5- and/or 12-lipoxygenase, comprising a pharmaceutical carrier and a therapeutically effective amount of a compound of claim 1.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1992-10-09 | 1993-04-10 | 1993-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-10-09 | 1997-04-10 | 1997-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-10-09 | 2001-04-10 | 2001-10-10 | $7700.00 | Window Closed / Lapsed |