US4497827A
Expired / Lapsed
US
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Arachidonic acid analogues as anti-inflammatory and anti-allergic agents
Assignee: Syntex USA LLC
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Filing: 1982-08-30
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Granted: 1985-02-05
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Expires: 2002-08-30
Abstract
Abstract Novel compounds of this invention are tetrazole, acylhydroxylamine, hydroxymethylketone and amide derivatives of unsaturated fatty acids which are selective inhibitors of the enzymes lipoxygenase and cyclooxygenase involved in the production of pain, inflammation, bronchoconstriction and allergic reactions. These compounds are beneficial in the treatment of a number of inflammatory and/or painful conditions and allergic reactions.
Inventors
- 👤 Peter H. Nelson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 21:39
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00; A61P37/00; A61P37/08; A61P7/00; A61P7/02; C07C; C07C255/00; C07C29/00; C07C29/09; C07C29/10; C07C33/00; C07C33/04; C07C33/048; C07C45/00; C07C45/61; C07C45/64; C07C49/00; C07C49/20; C07C49/24; C07C57/00; C07C57/18; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12
Claims Analysis
Total Claims: 62
Claim 1
Independent Claim
75 words
A compound chosen from those represented by the formulas ##STR12## and their pharmaceutically acceptable, non-toxic salts wherein A is C═C or C.tbd.C; B is C═C or C.tbd.C; D is C--C, C═C, or C.tbd.C; E is C--C, C═C, or C.tbd.C; F is C--C, C═C, or C.tbd.C; Z is CH 3 , CH 2 CH 3 , --CH 2 CH 2 CH 3 ; CH 2 CH 2 CH 2 CH 3 ; and X is C(O)NHOH.
Claim 2
Dependent Claim
75 words
A compound chosen from those represented by the formulas ##STR12## and their pharmaceutically acceptable, non-toxic salts wherein A is C═C or C.tbd.C; B is C═C or C.tbd.C; D is C--C, C═C, or C.tbd.C; E is C--C, C═C, or C.tbd.C; F is C--C, C═C, or C.tbd.C; Z is CH 3 , CH 2 CH 3 , --CH 2 CH 2 CH 3 ; CH 2 CH 2 CH 2 CH 3 ; and X is C(O)NHOH.
Claim 3
Dependent Claim
20 words
The compound of claim 1 and the pharmaceutically acceptable, non-toxic salts thereof, wherein the compound is represented by formula (1).
Claim 4
Dependent Claim
20 words
The compound of claim 2 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 3 .
Claim 5
Dependent Claim
19 words
The compound of claim 3 and the pharmaceutically acceptable, non-toxic salts thereof, wherein X is C(O)NHOH, namely eicosa-5(Z),8(Z), 11(Z),14(Z)-tetraenoylhydroxylamine.
Claim 6
Dependent Claim
18 words
The compound of claim 3 and the pharmaceutically acceptable, non-toxic salts thereof, wherein X is C(O)NHOH, namely eicosa-5,8,11,14-tetraynoylhydroxylamine.
Claim 7
Dependent Claim
22 words
The compound of claim 2 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 2 CH 3 .
Claim 8
Dependent Claim
18 words
The compound of claim 6 and the pharmaceutically acceptable, non-toxic salts thereof, wherein X is C(O)NHOH, namely heneicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoylhydroxylamine.
Claim 9
Dependent Claim
18 words
The compound of claim 6 and the pharmaceutically acceptable, non-toxic salts thereof, wherein X is C(O)NHOH, namely heneicosa-5,8,11,14-tetraynoylhydroxylamine.
Claim 10
Dependent Claim
18 words
The compound of claim 2 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 3 .
Claim 11
Dependent Claim
24 words
The compound of claim 9 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D, and F are C═C and E is C--C.
Claim 12
Dependent Claim
18 words
The compound of claim 9 and the pharmaceutically acceptable, non-toxic salts thereof, wherein X is C(O)NHOH, namely nonadeca-5,8,11,14-tetraynoylhydroxylamine.
Claim 13
Dependent Claim
23 words
The compound of claim 2 and the pharmaceutically acceptable, non-toxic salts wherein Z is --CH 2 CH 2 CH 2 CH 3 .
Claim 14
Dependent Claim
24 words
The compound of claim 12 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D, and F are C═C and E is C--C.
Claim 15
Dependent Claim
17 words
The compound of claim 12 and the pharmaceutically acceptable, non-toxic salts, wherein X is C(O)NHOH, namely docosa-5,8,11,14-tetraynoylhydroxylamine.
Claim 16
Dependent Claim
20 words
The compound of claim 1 and the pharmaceutically acceptable, non-toxic salts thereof, wherein the compound is represented by formula (2).
Claim 17
Dependent Claim
20 words
The compound of claim 15 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D, and F are C.tbd.C.
Claim 18
Dependent Claim
20 words
The compound of claim 16 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 3 .
Claim 19
Dependent Claim
24 words
The compound of claim 16 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 2 CH 2 CH 3 .
Claim 20
Dependent Claim
20 words
The compound of claim 1 and the pharmaceutically acceptable, non-toxic salts thereof, wherein the compound is represented by formula (3).
Claim 21
Dependent Claim
20 words
The compound of claim 19 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 3 .
Claim 22
Dependent Claim
24 words
The compound of claim 19 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 2 CH 2 CH 3 .
Claim 23
Dependent Claim
18 words
The compound of claim 21 and the pharmaceutically acceptable, non-toxic salts thereof, wherein X is C(O)NHOH, namely docosa-4,7,10,13-tetraynoylhydroxylamine.
Claim 24
Dependent Claim
35 words
The compound of claim 19 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D, and E are C.tbd.C; F is C--C, and Z is --CH 2 CH 2 CH 2 CH 3 .
Claim 25
Dependent Claim
24 words
The compound of claim 6 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D and E are C.tbd.C and F is C--C.
Claim 26
Dependent Claim
25 words
The compound of claim 3 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B and F are C.tbd.C and D and E are C--C.
Claim 27
Dependent Claim
18 words
The compound of claim 25 and the pharmaceutically acceptable, non-toxic salts thereof, wherein X is C(O)NHOH, namely eicosa-5,8,11-triynoylhydroxylamine.
Claim 28
Dependent Claim
43 words
The compound of claim 2, wherein A and D are C═C; B and F are C.tbd.C; E is C--C; and Z is CH 2 CH 3 ; CH 2 CH 2 CH 3 or CH 2 CH 2 CH 2 CH 3 .
Claim 29
Dependent Claim
21 words
The compound of claim 27 wherein X is C(O)NHOH and Z is CH 2 CH 2 CH 3 , namely heneicosa-8(Z),14(Z)-diene-5,11-diynoylhydroxylamine.
Claim 30
Dependent Claim
42 words
The compound of claim 2, wherein A, B and D are C═C, E is C--C, F is C.tbd.C and Z is CH 2 CH 3 , CH 2 CH 2 CH 3 or CH 2 CH 2 CH 2 CH 3 .
Claim 31
Dependent Claim
21 words
The compound of claim 29, wherein X is C(O)NHOH and Z is CH 2 CH 2 CH 3 , namely heneicosa-8(Z),11(Z),14(Z)-triene-5-ynoylhydroxylamine.
Claim 32
Dependent Claim
42 words
The compound of claim 2, wherein A, D and F are C═C, B is C.tbd.C, E is C--C and Z is CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 .
Claim 33
Dependent Claim
21 words
The compound of claim 31, wherein X is C(O)NHOH and Z is CH 2 CH 2 CH 3 , namely heneicosa-5(Z),8(Z),14(Z)-trien-11-ynoylhydroxylamine.
Claim 34
Dependent Claim
39 words
A pharmaceutical composition for preventing or treating inflammation and/or pain and allergic reactions in mammals which composition comprises a compound of claim 1 or a pharmaceutically acceptable, non-toxic salt thereof in admixture with at least one pharmaceutically acceptable excipient.
Claim 35
Dependent Claim
43 words
A method for preventing or treating inflammation and/or pain and allergic reactions in mammals which method comprises administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable, non-toxic salt thereof.
Claim 36
Dependent Claim
87 words
A compound chosen from those represented by the formulas ##STR13## and their pharmaceutically acceptable, non-toxic salts wherein A is C═C or C.tbd.C; B is C═C or C.tbd.C; D is C--C, C═C, or C.tbd.C; E is C--C, C═C, or C.tbd.C; F is C--C, C═C, or C.tbd.C; Z is CH 3 , CH 2 CH 3 , --CH 2 CH 2 CH 3 ; CH 2 CH 2 CH 2 CH 3 ; X is CONH 2 and at least one of A, B, D, or F is C.tbd.C.
Claim 37
Dependent Claim
87 words
A compound chosen from those represented by the formulas ##STR13## and their pharmaceutically acceptable, non-toxic salts wherein A is C═C or C.tbd.C; B is C═C or C.tbd.C; D is C--C, C═C, or C.tbd.C; E is C--C, C═C, or C.tbd.C; F is C--C, C═C, or C.tbd.C; Z is CH 3 , CH 2 CH 3 , --CH 2 CH 2 CH 3 ; CH 2 CH 2 CH 2 CH 3 ; X is CONH 2 and at least one of A, B, D, or F is C.tbd.C.
Claim 38
Dependent Claim
20 words
The compound of claim 35 and the pharmaceutically acceptable, non-toxic salts thereof, wherein the compound is represented by formula (1).
Claim 39
Dependent Claim
20 words
The compounds of claim 36 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 3 .
Claim 40
Dependent Claim
24 words
The compound of claim 36 and the pharmaceutically acceptable non-toxic salts thereof, wherein A, B, D, and F are C.tbd.C, and E is C--C.
Claim 41
Dependent Claim
22 words
The compound of claim 36 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 2 CH 3 .
Claim 42
Dependent Claim
24 words
The compound of claim 39 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D, and F are C.tbd.C, and E is C--C.
Claim 43
Dependent Claim
18 words
The compound of claim 36 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 3 .
Claim 44
Dependent Claim
23 words
The compound of claim 36 and the pharmaceutically acceptable, non-toxic salts wherein Z is --CH 2 CH 2 CH 2 CH 3 .
Claim 45
Dependent Claim
21 words
The compound of claim 35 and the pharmaceutically acceptable, non-toxic salts thereof, wherein the compound is represented by the formula (2).
Claim 46
Dependent Claim
20 words
The compound of claim 43 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D, and F are C.tbd.C.
Claim 47
Dependent Claim
20 words
The compound of claim 43 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 3 .
Claim 48
Dependent Claim
24 words
The compound of claim 43 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 2 CH 2 CH 3 .
Claim 49
Dependent Claim
21 words
The compound of claim 35 and the pharmaceutically acceptable, non-toxic salts thereof, wherein the compound is represented by the formula (3).
Claim 50
Dependent Claim
24 words
The compound of claim 47 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D, and F are C.tbd.C and E is C--C.
Claim 51
Dependent Claim
20 words
The compound of claim 47 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 3 .
Claim 52
Dependent Claim
24 words
The compound of claim 48 and the pharmaceutically acceptable, non-toxic salts thereof, wherein Z is --CH 2 CH 2 CH 2 CH 3 .
Claim 53
Dependent Claim
32 words
The compound of claim 47 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D, and E are C.tbd.C, and Z is --CH 2 CH 2 CH 2 CH 3 .
Claim 54
Dependent Claim
24 words
The compound of claim 39 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, D and E are C.tbd.C and F is C--C.
Claim 55
Dependent Claim
25 words
The compound of claim 37 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B and F are C.tbd.C and D and E are C--C.
Claim 56
Dependent Claim
25 words
The compound of claim 41 and the pharmaceutically acceptable, non-toxic salts thereof, wherein A, B, and D are C.tbd.C and E and F are C--C.
Claim 57
Dependent Claim
43 words
The compound of claim 36 wherein A and D are C═C; B and F are C.tbd.C; E is C--C; and Z is CH 2 CH 3 ; CH 2 CH 2 CH 3 or CH 2 CH 2 CH 2 CH 3 .
Claim 58
Dependent Claim
42 words
The compound of claim 36 wherein A, B and D are C═C, E is C--C, F is C.tbd.C and Z is CH 2 CH 3 , CH 2 CH 2 CH 3 or CH 2 CH 2 CH 2 CH 3 .
Claim 59
Dependent Claim
42 words
The compound of claim 36 wherein A, D and F are C═C, B is C.tbd.C, E is C--C and Z is CH 2 CH 3 , CH 2 CH 2 CH 3 or CH 2 CH 2 CH 2 CH 3 .
Claim 60
Dependent Claim
43 words
A method for preventing or treating inflammation and/or pain or allergic reactions in mammals which method comprises administering to a subject in need of such treatment a therapeutically effective amount of a compound of claim 35 or a pharmaceutically acceptable, non-toxic salt thereof.
Claim 61
Dependent Claim
20 words
The compound of claim 35, wherein X is CONH 2 and Z is CH 2 CH 3 , namely eicosa-5,8,11,14-tetraynamide.
Claim 62
Dependent Claim
22 words
The compound of claim 35 wherein X is CONH 2 and Z is CH 2 --CH 2 --CH 3 , namely heneicosa-5,8,11,14-tetraynamide.
References Cited (Backward Citations)
NL6604058A
Cited
GB1074693A
Cited
US3427316A
Cited
US3995059A
Cited
FR2140369A1
Cited
GB1373463A
Cited
BE785292A
Cited
FR2264522A1
Cited
US4116955A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-02-05 | 1988-08-06 | 1989-02-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-02-05 | 1992-08-06 | 1993-02-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-02-05 | 1996-08-06 | 1997-02-05 | $7700.00 | Window Closed / Lapsed |