US4803216A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pyrazole-3-amines as anti-inflammatory agents
Assignee: Fisons Ltd
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Filing: 1987-05-05
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Granted: 1989-02-07
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Expires: 2007-05-05
Abstract
Abstract There are described compounds of formula I, ##STR1## in which R 1 represents hydrogen, alkyl, alkanoyl or alkyl substituted by Ar 1 , R 3 , R 4 and R 5 , which may be the same or different, each independently represent hydrogen, alkyl or Ar 3 , Ar 1 , Ar 2 and Ar 3 , which may be the same or different, independently represent phenyl or phenyl substituted by one or more of alkyl, hydroxy, alkoxy, NR 6 R 7 or halogen, R 6 and R 7 , which may be the same or different, independently represent hydrogen or alkyl, and pharmaceutically acceptable acid addition salts thereof. Compositions containing the compounds and methods for their preparation are also described. The compounds are indicated for use as pharmaceutical, e.g. anti-inflammatory, agents.
Inventors
- 👤 Richard A. Appleton
- 👤 John Dixon
- 👤 Sidney C. Burford
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 04:19
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/38
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
221 words
A compound having the formula ##STR9## in which R 1 represents hydrogen, alkyl, alkanoyl or alkyl substituted by Ar 1 , R 3 , R 4 and R 5 , which may be the same or different, each independently represent hydrogen, alkyl or Ar 3 , Ar 1 , Ar 2 and Ar 3 , which may be the same or different, independently represent phenyl or phenyl substituted by one or more of alkyl, hydroxy, alkoxy, NR 6 R 7 or halogen, R 6 and R 7 , which may be the same or different, independently represent hydrogen or alkyl, provided that (i) when R 1 , R 3 and R 4 each represent hydrogen, and R 5 represents methyl, then Ar 2 does not represent phenyl or phenyl substituted by alkyl, alkoxy or halaogen and (ii) when R 1 , R 3 and R 4 each represent hydrogen and AR 2 represents phenyl or phenyl substituted by alkyl, then R 5 does not represent phenyl or phenyl substituted by alkyl, alkoxy or halogen, and (iii) when R 1 and R 3 represent hydrogen, and Ar 2 represents pheyl, then, (a) R 4 and R 5 do not both represent phenyl and (b) R 5 does not represent hydrogen when R 4 represents alkyl, and pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
221 words
A compound having the formula ##STR9## in which R 1 represents hydrogen, alkyl, alkanoyl or alkyl substituted by Ar 1 , R 3 , R 4 and R 5 , which may be the same or different, each independently represent hydrogen, alkyl or Ar 3 , Ar 1 , Ar 2 and Ar 3 , which may be the same or different, independently represent phenyl or phenyl substituted by one or more of alkyl, hydroxy, alkoxy, NR 6 R 7 or halogen, R 6 and R 7 , which may be the same or different, independently represent hydrogen or alkyl, provided that (i) when R 1 , R 3 and R 4 each represent hydrogen, and R 5 represents methyl, then Ar 2 does not represent phenyl or phenyl substituted by alkyl, alkoxy or halaogen and (ii) when R 1 , R 3 and R 4 each represent hydrogen and AR 2 represents phenyl or phenyl substituted by alkyl, then R 5 does not represent phenyl or phenyl substituted by alkyl, alkoxy or halogen, and (iii) when R 1 and R 3 represent hydrogen, and Ar 2 represents pheyl, then, (a) R 4 and R 5 do not both represent phenyl and (b) R 5 does not represent hydrogen when R 4 represents alkyl, and pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
18 words
A compound according to claim 1, in which R 1 represents hydrogen, CH 2 Ar 1 or alkyl.
Claim 4
Dependent Claim
20 words
A compound according to claim 1, in which Ar 2 is phenyl substituted by an OH, alkoxy or dialkylamino group.
Claim 5
Dependent Claim
12 words
A compound according to claim 1, in which Ar 2 represents hydroxyphenyl.
Claim 6
Dependent Claim
16 words
A compound according to claim 1, in which R 5 represents hydrogen or Ar 3 .
Claim 7
Dependent Claim
17 words
A compound according to claim 1, which is 4-(5-Phenyl-1H-pyrazol-3-yl)aminophenol or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
23 words
A compound according to claim 1, which is 4-(1-Phenylmethyl-1H-pyrazol-3-yl) aminophenol, 2-(1H-Pyrazol-3-yl)aminophenol, 2-(1-Methyl-1H-pyrazol-3-yl)aminophenol, or a pharmaceutically acceptable acid addition salt of any one thereof.
Claim 9
Dependent Claim
35 words
A compound according to claim 1, which is: N-(4-methoxyphenyl)-3(5)-phenyl-1H-pyrazol-5(3)-amine, 1-Acetyl-N-[4-methoxyphenyl]-1H-pyrazol-3-amine, N-[4-Methoxyphenyl]-1-phenylmethyl-1H-pyrazol-3-amine, N-[4-Methoxyphenyl]-1-[1-methyl]ethyl-1H-pyrazol-3-amine, N-[4-Methoxyphenyl]-1-methyl-1H-pyrazol-3-amine, 5-Methyl-N-phenyl-1-phenylmethyl-1H-pyrazol-3-amine, N-[4-Methoxyphenyl]-1H-pyrazol-3-amine, 5-Methyl-N-phenyl-1H-pyrazole-3-amine, N-[4-Methoxyphenyl]-5-methyl-1H-pyrazol-3-amine, N-[4-Methoxyphenyl]-1-methyl-5-phenyl-1H-pyrazol-3-amine, N-[4-Methoxyphenyl]-4,5-diphenyl-1H-pyrazol-3-amine, 4-[3-(4-Methoxyphenylamino)-1H-pyrazol-5-yl]phenol, N-(4-Hydroxyphenyl)-1H-pyrazol-3-amine, 4-(1-Methylpyrazol-3-yl)aminophenol, 1-Methyl-N-(4-dimethylaminophenyl)-1H-pyrazol-3-amino, 4-(1-(4-Methoxyphenyl)methylpyrazol-3-yl)aminophenol, or a pharmaceutically acceptable acid addition salt of any one thereof.
Claim 10
Dependent Claim
30 words
A method of treatment of an inflammatory condition, which comprises administration of an effective amount of a compound according to claim 1 to a patient suffering from such a condition.
Claim 11
Dependent Claim
29 words
A pharmaceutical composition for treating an inflammatory condition comprising an effective amount of a compound according to claim 1 in association with a pharmaceutically acceptable carrier, diluent, or adjuvant.
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) | 1992-02-07 | 1992-08-08 | 1993-02-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-02-07 | 1996-08-08 | 1997-02-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-02-07 | 2000-08-08 | 2001-02-07 | $7700.00 | Window Closed / Lapsed |