US4686231A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Inhibition of 5-lipoxygenase products
Assignee: SmithKline Beecham Corp
•
Filing: 1986-04-28
•
Granted: 1987-08-11
•
Expires: 2006-04-28
Abstract
Abstract Novel compounds, compositions and pharmaceutical a method of inhibiting the 5-lipoxygenase pathway in an animal in need thereof which comprising administering an effective, 5-lipoxygenase pathway inhibiting amount of a 4,5-diaryl-2(substituted)-imidazole or a pharmaceutically acceptable salt thereof.
Inventors
- 👤 Paul E. Bender
- 👤 Don E. Griswold
- 👤 Nabil Hanna
- 👤 Henry M. Sarau
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 16:07
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D233/00; C07D233/54; C07D233/66; C07D233/88
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
73 words
A compound of the formula ##STR32## wherein: X 1 is NHCN or NH 2 ; R 1 and R are independently selected from 4-pyridyl or monosubstituted phenyl wherein said substituent is selected from halo or C 1-4 alkoxy; and Y 1 is H or CN provided that when X 1 is NH 2 , Y 1 is CN when X 1 is NHCN, Y 1 is H; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
73 words
A compound of the formula ##STR32## wherein: X 1 is NHCN or NH 2 ; R 1 and R are independently selected from 4-pyridyl or monosubstituted phenyl wherein said substituent is selected from halo or C 1-4 alkoxy; and Y 1 is H or CN provided that when X 1 is NH 2 , Y 1 is CN when X 1 is NHCN, Y 1 is H; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
22 words
The compound of claim 1 wherein Y 1 is H, X 1 is NHCN and R and R 1 are both 4-methoxyphenyl.
Claim 4
Dependent Claim
41 words
The compound of claim 1 wherein Y 1 is H, X 1 is NHCN and R and R 1 are both 4-fluorophenyl; or wherein Y 1 is CN, X 1 is NH 2 and R and R 1 are both 4-fluorophenyl.
Claim 5
Dependent Claim
98 words
A pharmaceutical composition having 5-lipoxygenase inhibitory activity comprising an effective, non-toxic 5-lipoxygenase pathway inhibiting amount of a compound of the formula ##STR33## wherein: X 1 is NHCN or NH 2 ; R 1 and R are independently selected from 4-pyridyl or monosubstituted phenyl wherein said substituent is selected from halo or C 1-4 alkoxy; and Y 1 is H or CN provided that when X 1 is NH 2 , Y 1 is CN and when X 1 is NHCN, Y 1 is H; or a pharmaceutically acceptable salt or thereof, and a pharmaceutically acceptable carrier or diluent.
Claim 6
Dependent Claim
98 words
A pharmaceutical composition having 5-lipoxygenase inhibitory activity comprising an effective, non-toxic 5-lipoxygenase pathway inhibiting amount of a compound of the formula ##STR33## wherein: X 1 is NHCN or NH 2 ; R 1 and R are independently selected from 4-pyridyl or monosubstituted phenyl wherein said substituent is selected from halo or C 1-4 alkoxy; and Y 1 is H or CN provided that when X 1 is NH 2 , Y 1 is CN and when X 1 is NHCN, Y 1 is H; or a pharmaceutically acceptable salt or thereof, and a pharmaceutically acceptable carrier or diluent.
Claim 7
Dependent Claim
22 words
The composition of claim 4 wherein Y 1 is H, X 1 is NHCN and R and R 1 are both 4-methoxyphenyl.
Claim 8
Dependent Claim
40 words
The composition of claim 4 wherein Y 1 is H, X 1 is NHCN and R and R 1 are 4-fluorophenyl; or wherein Y 1 is CN, X 1 is NH 2 and R and R 1 are both 4-fluorophenyl.
Claim 9
Dependent Claim
18 words
The composition of claim 4 wherein the composition is in a dosage unit form adapted for parenteral administration.
Claim 10
Dependent Claim
23 words
The composition of claim 7 wherein the composition comprises the compound in an amount of from about 25 mg to about 200 mg.
Claim 11
Dependent Claim
19 words
The composition of claim 4 wherein the composition is in a dosage unit form adapted for administration of inhalation.
Claim 12
Dependent Claim
18 words
The composition of claim 4 wherein the composition is in a dosage unit form adapted for topical administration.
Claim 13
Independent Claim
100 words
A method for treating rheumatoid arthritis in an animal in need thereof which comprises administering to such animal an effective, non-toxic 5-lipoxygenase pathway inhibiting amount of a compound of the formula ##STR34## wherein: X 1 is NHCN or NH 2 ; R 1 and R are independently selected from 4-pyridyl or monosubstituted phenyl wherein said substituent is selected from halo or C 1-4 alkoxy; and Y 1 is H or CN provided that when X 1 is NH 2 , Y 1 is CN and when X 1 is NHCN, Y 1 is H; or a pharmaceutically acceptable salt thereof.
Claim 14
Independent Claim
100 words
A method for treating rheumatoid arthritis in an animal in need thereof which comprises administering to such animal an effective, non-toxic 5-lipoxygenase pathway inhibiting amount of a compound of the formula ##STR34## wherein: X 1 is NHCN or NH 2 ; R 1 and R are independently selected from 4-pyridyl or monosubstituted phenyl wherein said substituent is selected from halo or C 1-4 alkoxy; and Y 1 is H or CN provided that when X 1 is NH 2 , Y 1 is CN and when X 1 is NHCN, Y 1 is H; or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
22 words
The method of claim 11 wherein Y 1 is H, X 1 is NHCN and R and R 1 are both 4-methoxyphenyl.
Claim 16
Dependent Claim
39 words
The method of claim 11 wherein Y 1 is H, X 1 is NHCN and R and R 1 are both 4-fluorophenyl; or wherein Y is CN, X is NH 2 and R and R 1 are both 4-fluorophenyl.
Claim 17
Dependent Claim
11 words
The method of claim 11 wherein the compound is administered parenterally.
Claim 18
Dependent Claim
24 words
The method of claim 14 wherein the amount of compound administered in a dosage unit is from about 25 mg to about 200 mg.
Claim 19
Dependent Claim
22 words
The method of claim 14 wherein the amount of compound administered per day is from about 50 mg to about 1000 mg.
Claim 20
Dependent Claim
12 words
The method of claim 14 wherein the compound is administered by inhalation.
Claim 21
Dependent Claim
22 words
The method of claim 17 wherein the amount of compound administered is from about 10 mg to about 200 mg per day.
Claim 22
Dependent Claim
11 words
The method of claim 14 wherein the compound is administered topically.
Claim 23
Dependent Claim
19 words
The method of claim 19 wherein the amount of compound administered per dose is 1 μg to 1000 μg.
Claim 24
Independent Claim
179 words
A method of treating a 5-lipoxygenase pathway mediated disease in an animal in need thereof, provided that such animal is in need of treatment of a 5-lipoxygenase pathway mediated disease other than, or in addition to, rheumatoid arthritis, which comprises administering to such animal an effective, non-toxic 5-lipoxygenase pathway inhibiting amount of a compound of the formula, ##STR35## wherein: X is S, S(0) n R 2 , NHCN, NH 2 , polyhalo C 1-4 alkyl, or 4-halophenyl; n is 0, 1 or 2; R 2 is selected from H, C 1-6 alkyl, or mono- or polyhalo C 1-4 alkyl; R and R 1 are independently selected from pyridyl or mono substituted phenyl wherein said substituent is selected from halo or C 1-4 alkoxy; provided that when R and/or R 1 are pyridyl, R 2 is other than C 1-6 alkyl, tetrahaloethyl or C 1-4 perhaloalkyl; and Y is H, CN, or C 1-4 alkyl provided that when X is NH 2 , Y is CN and when X is NHCN, Y is H; or a pharmaceutically acceptable salt thereof.
Claim 25
Independent Claim
179 words
A method of treating a 5-lipoxygenase pathway mediated disease in an animal in need thereof, provided that such animal is in need of treatment of a 5-lipoxygenase pathway mediated disease other than, or in addition to, rheumatoid arthritis, which comprises administering to such animal an effective, non-toxic 5-lipoxygenase pathway inhibiting amount of a compound of the formula, ##STR35## wherein: X is S, S(0) n R 2 , NHCN, NH 2 , polyhalo C 1-4 alkyl, or 4-halophenyl; n is 0, 1 or 2; R 2 is selected from H, C 1-6 alkyl, or mono- or polyhalo C 1-4 alkyl; R and R 1 are independently selected from pyridyl or mono substituted phenyl wherein said substituent is selected from halo or C 1-4 alkoxy; provided that when R and/or R 1 are pyridyl, R 2 is other than C 1-6 alkyl, tetrahaloethyl or C 1-4 perhaloalkyl; and Y is H, CN, or C 1-4 alkyl provided that when X is NH 2 , Y is CN and when X is NHCN, Y is H; or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
11 words
The method of claim 21 wherein the compound is administered parenterally.
Claim 27
Dependent Claim
24 words
The method of claim 22 wherein the amount of compound administered in a dosage unit is from amount 50 mg to about 500 mg.
Claim 28
Dependent Claim
22 words
The method of claim 22 wherein the amount of compound administered per day is from about 50 mg to about 1000 mg.
Claim 29
Dependent Claim
12 words
The method of claim 21 wherein the compound is administered by inhalation.
Claim 30
Dependent Claim
22 words
The method of claim 25 wherein the amount of compound administered is from about 10 mg to about 200 mg per day.
Claim 31
Dependent Claim
11 words
The method of claim 21 wherein the compound is administered topically.
Claim 32
Dependent Claim
19 words
The method of claim 27 wherein the amount of compound administered per dose is 1 μg to 1000 μg.
Claim 33
Dependent Claim
23 words
The method of claim 21 wherein R and R 1 are both 4-methoxyphenyl, X is 3--CH 3 and Y is CH 3 .
Claim 34
Dependent Claim
26 words
The method of claim 21 wherein R and R 1 are both 4-fluorophenyl, X is SO 2 CF 2 CF 2 H and Y is H.
Claim 35
Dependent Claim
27 words
The method of claim 21 wherein R and R 1 are both 4-methoxyphenyl, X is 3--CH 2 CH 3 and Y is CH 2 CH 3 .
Claim 36
Dependent Claim
20 words
The method of claim 21 wherein R and R 1 are both 4-methoxyphenyl, X is NHCN and Y is H.
Claim 37
Dependent Claim
37 words
The method of claim 21 wherein R and R 1 are both 4-fluorophenyl, X is NHCN and Y is H; or wherein R and R 1 are both 4-fluorophenyl, X is NH 2 and Y is CN.
Claim 38
Dependent Claim
20 words
The method of claim 21 wherein R and R 1 are both 4-methoxyphenyl, X is trifluoromethyl and Y is H.
Claim 39
Dependent Claim
20 words
The method of claim 21 wherein R and R 1 are both 4-fluorophenyl, X is 4-fluorophenyl and Y is H.
Claim 40
Dependent Claim
20 words
The method of claim 21 wherein R is 4-pyridyl, R 1 is 4-fluorophenyl, X is S and Y is H.
Claim 41
Dependent Claim
24 words
The method of claim 21 wherein R is 4-pyridyl, R 1 is 4-fluorophenyl, X is SCF 2 CF 2 H and Y is H.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-08-10 | 1991-02-09 | 1991-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-10 | 1995-02-09 | 1995-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-10 | 1999-02-09 | 1999-08-11 | $7700.00 | Window Closed / Lapsed |