US3933840A
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Azole derivatives
Assignee: Merck Patent GmbH
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Filing: 1972-06-06
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Granted: 1976-01-20
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Expires: 1992-06-06
Abstract
Abstract Azole derivatives of the formula ##SPC1## Wherein R 1 is free or esterified carboxyl or other functionally modified carboxyl group, R 2 and R 3 each are aryl; A is C n H 2n in which n is an integer from 1 to 10, inclusive; and Z is O or S; and the physiologically acceptable salts thereof, possess, with good compatibility, excellent antiphlogistic activity and, in particular, influence favorably the chronic progressive diseases of the joints, e.g., arthritis. They can be prepared from compounds of the formula ##SPC2## Wherein X 1 is a group convertible into the group --S--A--R 1 , and R 2 and R 3 have the values given above.
Inventors
- 👤 Johann Dahm
- 👤 Joachim Borck
- 👤 Albrecht Wild
- 👤 Jan Willem Hovy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 16:51
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/36; C07D263/00; C07D263/02; C07D263/30; C07D263/34; C07D263/46
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
113 words
An antiphlogistic compound of the formula ##SPC5## wherein R 1 is carboxyl, a physiologically acceptable C 1-12 alkyl ester thereof, --CONH 2 or --CN; R 2 and R 3 each are phenyl or phenyl mono- or di- substituted by at least one member selected from the group consisting of alkyl, alkoxy, alkylmercapto, monoalkylamino, dialkylamino or alkanoylamino wherein the alkyl, alkoxy and alkanoyl each are of up to 4 carbon atoms; F, Cl, Br, I, CF 3 , OH, methylenedioxy, NH 2 and NO 2 ; A is C n H 2n wherein n is an integer from 1 to 10 inclusive; and Z is O or S, and the physiologically acceptable salts thereof.
Claim 2
Dependent Claim
113 words
An antiphlogistic compound of the formula ##SPC5## wherein R 1 is carboxyl, a physiologically acceptable C 1-12 alkyl ester thereof, --CONH 2 or --CN; R 2 and R 3 each are phenyl or phenyl mono- or di- substituted by at least one member selected from the group consisting of alkyl, alkoxy, alkylmercapto, monoalkylamino, dialkylamino or alkanoylamino wherein the alkyl, alkoxy and alkanoyl each are of up to 4 carbon atoms; F, Cl, Br, I, CF 3 , OH, methylenedioxy, NH 2 and NO 2 ; A is C n H 2n wherein n is an integer from 1 to 10 inclusive; and Z is O or S, and the physiologically acceptable salts thereof.
Claim 3
Dependent Claim
18 words
A compound of claim 1, wherein R 1 is --COOH, --COOCH 3 or --COOC 2 H 5 .
Claim 4
Dependent Claim
20 words
A compound of claim 1, wherein A is --CH 2 --, --CH(CH 3 ) or --CH(C 2 H 5 )--.
Claim 5
Dependent Claim
27 words
A compound of claim 1, wherein R 2 and R 3 are phenyl or phenyl monosubstituted by methyl, methoxy, methylmercapto, F, Cl, Br or CF 3 .
Claim 6
Dependent Claim
32 words
A compound of claim 4, wherein R 1 is --COOH, --COOCH 3 or --COOC 2 H 5 and A is --CH 2 --, --CH(CH 3 )-- or --CH(C 2 H 5 )--.
Claim 7
Dependent Claim
15 words
A compound of claim 4, wherein R 2 and R 3 are phenyl or p-chlorophenyl.
Claim 8
Dependent Claim
32 words
A compound of claim 6, wherein R 1 is --COOH, --COOCH 3 or --COOC 2 H 5 and A is --CH 2 --, --CH(CH 3 )-- or --CH(C 2 H 5 )--.
Claim 9
Dependent Claim
7 words
A compound of claim 1, 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid.
Claim 10
Dependent Claim
9 words
A compound of claim 1, 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid ethyl ester.
Claim 11
Dependent Claim
7 words
A compound of claim 1, 4,5-bis-p-chlorophenyl-2-oxazolyl-mercaptoacetic acid.
Claim 12
Dependent Claim
22 words
A compound of claim 1 selected from the group consisting of 4,5-bis-p-chlorophenyl-2-oxazolylmercaptoacetic acid methyl ester; 4,5-bis-p-chlorophenyl-2-oxazolyl-mercaptoacetic acid ethyl ester; 4,5-bis-p-chlorophenyl-2-oxazolyl-mercaptoacetamide; and 4,5-bis-p-chlorophenyl-2-oxazolyl-mercaptoacetonitrile.
Claim 13
Dependent Claim
7 words
A compound of claim 1, 2-(4,5-bis-p-chlorophenyl-2-oxazolyl-mercapto)-propionic acid.
Claim 14
Dependent Claim
9 words
A compound of claim 1, 2-(4,5-bis-p-chlorophenyl-2-oxazolyl-mercapto)-propionic acid ethyl ester.
Claim 15
Dependent Claim
7 words
A compound of claim 1, 2-(4,5-bis-p-chlorophenyl-2-oxazolyl-mercapto)-butyric acid.
Claim 16
Dependent Claim
9 words
A compound of claim 1, 2-(4,5-bis-p-chlorophenyl-2-oxazolyl-mercapto)-butyric acid ethyl ester.
Claim 17
Dependent Claim
87 words
A compound of claim 1 selected from the group consisting of 2-(4,5-diphenyl-2-oxazolyl-mercapto)-propionic acid, 2-(4,5-diphenyl-2-oxazolyl-mercapto)-butyric acid, 2-(4,5-diphenyl-2-oxazolyl-mercapto)-2-methylpropionic acid, 3-(4,5-diphenyl-2-oxazolylmercapto)-propionic acid, 4-(4,5-diphenyl-2-oxazolylmercapto)-butyric acid, 7-(4,5-diphenyl-2-oxazolylmercapto)-heptanoic acid, 4,5-bis-p-tolyl-2-oxazolylmercaptoacetic acid, 2-(4,5-bis-p-tolyl-2-oxazolylmercapto)-propionic acid, 2-(4,5-bis-p-tolyl-2-oxazolylmercapto)-butyric acid, 4,5-bis-p-isopropylphenyl-2-oxazolyl-mercaptoacetic acid, 2-(4,5-bis-p-isopropylphenyl-2-oxazolyl-mercapto)-propionic acid, 4,5-bis-o-chlorophenyl-2-oxazolyl-mercaptoacetic acid, 3-(4,5-bis-p-chlorophenyl-2-oxazolyl-mercapto)-propionic acid, 4-p-methoxyphenyl-5-phenyl-2-oxazolyl-mercaptoacetic acid, 4,5-bis-m-methoxyphenyl-2-oxazolyl-mercaptoacetic acid, 4,5-bis-m-methoxyphenyl-2-oxazolyl-mercaptoacetic acid, 2-(4,5-bis-p-methoxyphenyl-2-oxazolyl-mercapto)-propionic acid, 2-(4,5-bis-p-methoxyphenyl-2-oxazolylmercapto)-butyric acid, 4-p-methoxyphenyl-5-o-chlorophenyl-2-oxazolyl-mercaptoacetic acid, 4,5-bis-(3,4-dimethoxyphenyl)-2-oxazolyl-mercaptoacetic acid, 4,5-bis-(3,4-methylenedioxyphenyl)-2-oxazolyl-mercaptoacetic acid, 2-[4,5-bis-(3,4-methylenedioxyphenyl)-2-oxazolylmercapto]-propionic acid, 4-(3,4-methylenedioxyphenyl)-5-p-chlorophenyl-2-oxazolyl-mercaptoacetic acid, 4-p-dimethylaminophenyl-5-phenyl-2-oxazolyl-mercaptoacetic acid, 4-p-dimethylaminophenyl-5-o-chlorophenyl-2-oxazolylmercaptoacetic acid, 4-p-dimethylaminophenyl-5-p-chlorophenyl-2-oxazolyl-mercaptoacetic acid, 4,5-diphenyl-2-thiazolyl-mercaptoacetic acid, 2-(4,5-diphenyl-2-thiazolyl-mercapto)-2-methylpropionic acid, 4-(4,5-diphenyl-2-thiazolyl-mercapto)-butyric acid, 7-(4,5-diphenyl-2-thiazolyl-mercapto)-heptanoic acid, 4-p-tolyl-5-phenyl-2-thiazolyl-mercaptoacetic acid, 4-fluorophenyl-5-phenyl-2-thiazolyl-mercaptoacetic acid, 4,5,bis-p-chlorophenyl-2-thiazolyl-mercaptoacetic acid, and the ethyl ester of each of the above compounds.
Claim 18
Dependent Claim
9 words
A compound of claim 1 wherein Z is O.
Claim 19
Dependent Claim
47 words
A compound of claim 17 wherein R 1 is COOH or --COO--alkyl of 1-6 carbon atoms, R 2 and R 3 each are phenyl or phenyl monosubstituted by methyl, methoxy, methylmercapto, F, Cl, Br or CF 3 and A is alkylene of 1 to 6 carbon atoms.
Claim 20
Dependent Claim
107 words
An antiphlogistic compound of the formula ##SPC6## wherein R 6 is dialkylaminoalkyl of up to 10 carbon atoms; R 2 and R 3 each are phenyl or phenyl mono- or di- substituted by at least one member selected from the group consisting of alkyl, alkoxy, alkylmercapto, monoalkylamino, dialkylamino or alkanoylamino wherein the alkyl, alkoxy and alkanoyl each are of up to 4 carbon atoms, F, Cl, Br, I, CF 3 , OH, methylenedioxy, NH 2 and NO 2 ; A is C n H 2n wherein n is an integer from 1 to 10 inclusive; and Z is O or S, and the physiologically acceptable salts thereof.
Claim 21
Dependent Claim
107 words
An antiphlogistic compound of the formula ##SPC6## wherein R 6 is dialkylaminoalkyl of up to 10 carbon atoms; R 2 and R 3 each are phenyl or phenyl mono- or di- substituted by at least one member selected from the group consisting of alkyl, alkoxy, alkylmercapto, monoalkylamino, dialkylamino or alkanoylamino wherein the alkyl, alkoxy and alkanoyl each are of up to 4 carbon atoms, F, Cl, Br, I, CF 3 , OH, methylenedioxy, NH 2 and NO 2 ; A is C n H 2n wherein n is an integer from 1 to 10 inclusive; and Z is O or S, and the physiologically acceptable salts thereof.
References Cited (Backward Citations)
US2513923A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-19 | 1979-07-21 | 1980-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-19 | 1983-07-21 | 1984-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-19 | 1987-07-21 | 1988-01-20 | $7700.00 | Window Closed / Lapsed |