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EP0279263A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Indole, benzofuran, benzothiophene containing lipoxygenase inhibiting compounds

Assignee: Abbott Laboratories
•
Filing: 1988-02-01
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Granted: —
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Expires: 2008-02-01
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Abstract

Abstract Compounds of the formula: wherein R₁ is (1) hydrogen, (2) C₁ to C₄ alkyl, (3) C₂ to C₄ alkenyl, or (4) NR₂R₃, wherein R₂ and R₃ are independently selected from (1) hydrogen, (2) C₁ to C₄ alkyl and (3) hydroxyl, but R₂ and R₃ are not simultaneously hydroxyl; wherein X is oxygen, sulfur, SO₂, or NR₄, wherein R₄ is (1) hydrogen, (2) C₁ to C₆ alkyl, (3) C₁ to C₆ alkoyl, (4) aroyl, or (5) alkylsulfonyl; A is selected from C₁ to C₆ alkylene and C₂ to C₆ 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) C₁ to C₁₂ alkyl, (7) C₂ to C₁₂ alkenyl, (8) C₁ to C₁₂ alkoxy, (9) C₃ to C₈ cycloalkyl, (10) C₁-C₈ thioalkyl, (11) aryl, (12) aryloxy, (13) aroyl, (14) C₁ to C₁₂ arylalkyl, (15) C₂ to C₁₂ arylalkenyl, (16) C₁ to C₁₂ arylalkoxy, (17) C₁ to C₁₂ arylthioalkoxy, and substituted derivatives of (18) aryl, (19) aryloxy, (20) aroyl, (21) C₁ to C₁₂ arylalkyl, (22) C₂ to C₁₂ arylalkenyl, (23) C₁ to C₁₂ arylalkoxy, or (24) C₁ to C₁₂ arylthioalkoxy, wherein substituents are selected from halo, nitro, cyano, C₁ to C₁₂ alkyl, alkoxy, and halosubstituted alkyl; Z is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C₁ to C₁₂ 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 EP
Data Source google_patents
Last Synchronized 2026-11-05 09:04
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/14; A; A61; A61P; A61P11/00; A61P11/16; A61P29/00; A61P37/00; A61P37/08; A61P43/00; C07D307/00; C07D307/77; C07D307/78; C07D307/79; C07D307/81; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/58

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 227 words
A compound of the formula: wherein R₁ is (1) hydrogen, (2) C₁ to C₄ alkyl, (3) C₂ to C₄ alkenyl, or (4) NR₂R₃, wherein R₂ and R₃ are independently selected from (1) hydrogen, (2) C₁ to C₄ alkyl and (3) hydroxyl, but R₂ and R₃ are not simultaneously hydroxyl; wherein X is oxygen, sulfur, SO₂, or NR₄, wherein R₄ is (1) hydrogen, (2) C₁ to C₆ alkyl, (3) C₁ to C₆ alkoyl, (4) aroyl, or (5) alkylsulfonyl; A is selected from C₁ to C₆ alkylene and C₂ to C₆ 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) C₁ to C₁₂ alkyl, (7) C₂ to C₁₂ alkenyl, (8) C₁ to C₁₂ alkoxy, (9) C₃ to C₈ cycloalkyl, (10) C₁-C₈ thioalkyl, (11) aryl, (12) aryloxy, (13) aroyl, (14) C₁ to C₁₂ arylalkyl, (15) C₂ to C₁₂ arylalkenyl, (16) C₁ to C₁₂ arylalkoxy, (17) C₁ to C₁₂ arylthioalkoxy, and substituted derivatives of (18) aryl, (19) aryloxy, (20) aroyl, (21) C₁ to C₁₂ arylalkyl, (22) C₂ to C₁₂ arylalkenyl, (23) C₁ to C₁₂ arylalkoxy, or (24) C₁ to C₁₂ arylthioalkoxy, wherein substituents are selected from halo, nitro, cyano, C₁ to C₁₂ alkyl, alkoxy, and halosubstituted alkyl; Z is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C₁ to C₁₂ alkoyl.
Claim 2
Dependent Claim 227 words
A compound of the formula: wherein R₁ is (1) hydrogen, (2) C₁ to C₄ alkyl, (3) C₂ to C₄ alkenyl, or (4) NR₂R₃, wherein R₂ and R₃ are independently selected from (1) hydrogen, (2) C₁ to C₄ alkyl and (3) hydroxyl, but R₂ and R₃ are not simultaneously hydroxyl; wherein X is oxygen, sulfur, SO₂, or NR₄, wherein R₄ is (1) hydrogen, (2) C₁ to C₆ alkyl, (3) C₁ to C₆ alkoyl, (4) aroyl, or (5) alkylsulfonyl; A is selected from C₁ to C₆ alkylene and C₂ to C₆ 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) C₁ to C₁₂ alkyl, (7) C₂ to C₁₂ alkenyl, (8) C₁ to C₁₂ alkoxy, (9) C₃ to C₈ cycloalkyl, (10) C₁-C₈ thioalkyl, (11) aryl, (12) aryloxy, (13) aroyl, (14) C₁ to C₁₂ arylalkyl, (15) C₂ to C₁₂ arylalkenyl, (16) C₁ to C₁₂ arylalkoxy, (17) C₁ to C₁₂ arylthioalkoxy, and substituted derivatives of (18) aryl, (19) aryloxy, (20) aroyl, (21) C₁ to C₁₂ arylalkyl, (22) C₂ to C₁₂ arylalkenyl, (23) C₁ to C₁₂ arylalkoxy, or (24) C₁ to C₁₂ arylthioalkoxy, wherein substituents are selected from halo, nitro, cyano, C₁ to C₁₂ alkyl, alkoxy, and halosubstituted alkyl; Z is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C₁ to C₁₂ alkoyl.
Claim 3
Dependent Claim 55 words
A compound of claim 1 having the formula: wherein R₅ is C₁ or C₂ alkyl, or NR₆R₇ where R₆ and R₇ are independently selected from hydrogen and C₁ or C₂ alkyl; B is CH₂ or CHCH₃; W is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C₁ to C₁₂ alkoyl.
Claim 4
Dependent Claim 8 words
The compound of claim 1 having the formula:
Claim 5
Dependent Claim 8 words
The compound of claim 1 having the formula:
Claim 6
Dependent Claim 26 words
Use of a compound of claim 1 for preparing a drug useful for inhibiting 5- and/or 12-lipoxygenase activity in a mammal in need of such treatment.
Claim 7
Dependent Claim 57 words
Use of claim 5 wherein the compound has the formula: wherein R₅ is C₁ or C₂ alkyl, or NR₆R₇ where R₆ and R₇ are independently selected from hydrogen and C₁ or C₂ alkyl; B is CH₂ or CHCH₃; W is oxygen or sulfur; and M is hydrogen, a pharmaceutically acceptable cation, aroyl, or C₁ to C₁₂ alkoyl.
Claim 8
Dependent Claim 10 words
Use of claim 5 wherein the compound has the formula
Claim 9
Dependent Claim 10 words
Use of claim 5 wherein the compound has the formula:
Claim 10
Dependent Claim 40 words
Use of a compound of claim 1 for preparing a drug useful for treating asthma, rheumatoid arthritis, gout, psoriasis, allergic rhinitis, adult respiratory distress syndrome, Crohn's disease, endotoxin shock, inflammatory bowel disease and/or ischemia induced myocardial or brain injury .
Claim 11
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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