US4171365A
Expired / Lapsed
US
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Antiviral aryloxyalkylpyrazoles
Assignee: STWB Inc
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Filing: 1977-08-05
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Granted: 1979-10-16
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Expires: 1997-08-05
Abstract
Abstract 4-(Aryloxyalkyl)pyrazoles of the formula ##STR1## useful as antiviral agents, are prepared by reacting the corresponding diketones of the formula Ar--O--Alk--CH(COR')COR" with hydrazine or a substituted hydrazine H 2 NNHR. Mono- or bis-pyrazoles are similarly obtained from bis-diketones of the formula ##STR2##
Inventors
- 👤 Guy D. Diana
- 👤 Philip M. Carabateas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 01:36
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A61; A61P; A61P31/00; A61P31/12; C07C; C07C317/00; C07C43/00; C07C43/02; C07C43/20; C07C43/225; C07C45/00; C07C45/61; C07C45/67; C07C45/68
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
151 words
A compound of the formula ##STR8## wherein R is hydrogen, alkyl of 1 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms, carboalkoxyalkyl of 3 to 6 carbon atoms, or phenyl; R' is alkyl of 1 to 4 carbon atoms or phenyl; R" is alkyl of 1 to 4 carbon atoms, phenyl or hydroxy; Alk is alkylene of 3 to 10 carbon atoms optionally interrupted by an oxygen atom separated by at least two carbon atoms from the terminal bonds of Alk; and Ar is phenyl or phenyl substituted by from 1 to 3 substituents selected from the group consisting of halo, hydroxy, nitro, alkyl of 1 to 4 carbon atoms, lower-alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, hydroxyalkyl of 2 to 4 carbon atoms, benzyloxy and trifluoromethyl; or a pharmaceutically acceptable acid-addition salt thereof.
Claim 2
Dependent Claim
151 words
A compound of the formula ##STR8## wherein R is hydrogen, alkyl of 1 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms, carboalkoxyalkyl of 3 to 6 carbon atoms, or phenyl; R' is alkyl of 1 to 4 carbon atoms or phenyl; R" is alkyl of 1 to 4 carbon atoms, phenyl or hydroxy; Alk is alkylene of 3 to 10 carbon atoms optionally interrupted by an oxygen atom separated by at least two carbon atoms from the terminal bonds of Alk; and Ar is phenyl or phenyl substituted by from 1 to 3 substituents selected from the group consisting of halo, hydroxy, nitro, alkyl of 1 to 4 carbon atoms, lower-alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, hydroxyalkyl of 2 to 4 carbon atoms, benzyloxy and trifluoromethyl; or a pharmaceutically acceptable acid-addition salt thereof.
Claim 3
Dependent Claim
22 words
A compound according to claim 1 wherein R is hydrogen, and R' and R" are alkyl of 1 to 4 carbon atoms.
Claim 4
Dependent Claim
25 words
A compound according to claim 1 wherein R is hydrogen, R' and R" are alkyl of 1 to 4 carbon atoms, and Ar is 2-chloro-4-methoxyphenyl.
Claim 5
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1H-pyrazole, according to claim 3.
Claim 6
Dependent Claim
5 words
4-[6-(4-Methoxy-2-nitrophenoxy)hexyl]-3,5-diethyl-1H-pyrazole, according to claim 2.
Claim 7
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-dimethyl-1H-pyrazole, according to claim 3.
Claim 8
Dependent Claim
5 words
4-{2-[2-(2-Chloro-4-methoxyphenoxy)ethoxy]ethyl}-3,5-diethyl-1H-pyrazole, according to claim 3.
Claim 9
Dependent Claim
5 words
4-[6-(2-Chloro-4-hydroxyphenoxy)hexyl]-3,5-diethyl-1H-pyrazole, according to claim 2.
Claim 10
Dependent Claim
5 words
4-[5-(2-Chloro-4-methoxyphenoxy)pentyl]-3,5-diethyl-1H-pyrazole, according to claim 3.
Claim 11
Dependent Claim
5 words
4-[4-(2-Chloro-4-methoxyphenoxy)butyl]-3,5-diethyl-1H-pyrazole, according to claim 3.
Claim 12
Dependent Claim
5 words
4-[7-(2-Chloro-4-methoxyphenoxy)heptyl]-3,5-diethyl-1H-pyrazole, according to claim 3.
Claim 13
Dependent Claim
5 words
4-[6-(2-Chloro-4-methylsulfinylphenoxy)hexyl]-3,5-diethyl-1H-pyrazole, according to claim 2.
Claim 14
Dependent Claim
5 words
4-[6-(4-Chlorophenoxy)hexyl]-3,5-diethyl-1H-pyrazole, according to claim 2.
Claim 15
Dependent Claim
16 words
A compound according to claim 1 wherein R is hydrogen, and R' and R" are phenyl.
Claim 16
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-diphenyl-1H-pyrazole, according to claim 14.
Claim 17
Dependent Claim
28 words
A compound according to claim 1 wherein R is loweralkyl of 1 to 6 carbon atoms, and R' and R" are alkyl of 1 to 4 carbon atoms.
Claim 18
Dependent Claim
31 words
A compound according to claim 1 wherein R is loweralkyl of 1 to 6 carbon atoms, R' and R" are alkyl of 1 to 4 carbon atoms and Ar is 2-chloro-4-methoxyphenyl.
Claim 19
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-dimethyl-1-butyl-1H-pyrazole, according to claim 17.
Claim 20
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1-methyl-1H-pyrazole, according to claim 17.
Claim 21
Dependent Claim
5 words
4-[5-(2-Chloro-4-methoxyphenoxy)pentyl]-3,5-diethyl-1-methyl-1H-pyrazole, according to claim 17.
Claim 22
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-1,3,5-trimethyl-1H-pyrazole, according to claim 17.
Claim 23
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-1-ethyl-3,5-dimethyl-1H-pyrazole, according to claim 17.
Claim 24
Dependent Claim
5 words
4-[7-(2-Chloro-4-methoxyphenoxy)heptyl]-1,3,5-trimethyl-1H-pyrazole, according to claim 17.
Claim 25
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-dimethyl-1-propyl-1H-pyrazole, according to claim 17.
Claim 26
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1H-pyrazole-1-ethanol, according to claim 1.
Claim 27
Dependent Claim
6 words
Ethyl 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1H-pyrazol-1-acetate, according to claim 1.
Claim 28
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1-phenyl-1H-pyrazole, according to claim 1.
Claim 29
Dependent Claim
5 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-3-methyl-1H-pyrazole-5-ol, according to claim 1.
Claim 30
Dependent Claim
1 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-1-(2-dimethylaminoethyl)-3,5-diethyl-1H-pyrazole.
Claim 31
Dependent Claim
1 words
4-[6-(2-Chloro-4-methoxyphenoxy)hexyl]-1-(2-dimethylaminoethyl)-3,5-diethyl-1H-pyrazole.
Claim 32
Dependent Claim
28 words
A composition for combatting viruses which comprises an antivirally effective amount of at least one compound according to claim 1 in admixture with a suitable carrier or diluent.
Claim 33
Dependent Claim
20 words
A composition according to claim 30 wherein the antivirally effective compound is 4-[6-(2-chloro-4-methoxyphenoxy)hexyl]-3,5-diethyl-1H-pyrazole or a pharmaceutically acceptable acid-addition salt thereof.
Claim 34
Dependent Claim
27 words
A method for combatting viruses which comprises contacting the locus of said viruses with an antivirally effective amount of at least one compound according to claim 1.
Claim 35
Dependent Claim
20 words
A method according to claim 32 wherein the antivirally effective compound is 4-[6-(2-chloro-4-methoxyphenoxy)-hexyl]-3,5-diethyl-1H-pyrazole or a pharmaceutically acceptable acid-addition salt thereof.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-10-15 | 1983-04-16 | 1983-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-10-15 | 1987-04-16 | 1987-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-10-15 | 1991-04-16 | 1991-10-16 | $7700.00 | Window Closed / Lapsed |