Patent US3938609A successfully refreshed from Google Patents.
Patent US4061767A successfully refreshed from Google Patents.
US4061767A
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Cyano acetic acid anilide derivatives, process for their manufacture and compositions containing these compounds
Assignee: Hoechst AG
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Filing: 1976-06-03
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Granted: 1977-12-06
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Expires: 1996-06-03
Abstract
Abstract A 2-hydroxyethylidene-cyano acetic acid anilide is prepared by heating an acetoacetic acid anilide with an orthoformic acid ester and acetic anhydride, isolating the resulting 2-alkoxymethylene-acetoacetic acid anilide and treating it with hydroxylamine and the isoxazole so obtained with a base, and optionally reacting the resulting alkali metal or ammonium salt with a mineral acid or a strong organic acid. The compounds of the invention have anti-inflammatory and analgesic activity.
Inventors
- 👤 Hartmut Ertel
- 👤 Gunther Heubach
- 👤 Erhard Wolf
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:04
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/62; C07D317/66; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00; C07C; C07C255/00; C07D261/00; C07D261/02; C07D261/06; C07D261/10; C07D261/18
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
202 words
A 2-hydroxyethylidene-cyano acetic acid aniline of the formula ##STR20## wherein each of R 1 , R 2 and R 3 , is alkyl of from 1 to 3 carbon atoms, alkoxy of from 1 to 3 carbon atoms, alkylthio of from 1 to 3 carbon atoms; said alkyl, alkoxy or alkylthio substituted in the alkyl moiety by halogen; halogen; nitro; cyano or alkoxycarbonyl of 1 to 3 carbon atoms in the alkyl moiety; also wherein either or both of R 1 and R 2 are hydrogen, and R 3 additionally is phenyl; phenyl substituted by one or two fluorine, chlorine, bromine or iodine atoms, alkyl of from 1 to 3 carbon atoms or alkoxy of from 1 to 3 carbon atoms; phenoxy; or phenoxy substituted by one or two fluorine, chlorine, bromine or iodine atoms, alkyl of from 1 to 3 carbon atoms or alkoxy of from 1 to 3 carbon atoms; but R 3 is not methyl when both R 1 and R 2 are hydrogen; or R 1 is hydrogen, and R 2 and R 3 together are methylene-dioxy or, together with the phenyl ring to which they are linked, naphthalene; and M is hydrogen, an alkali metal or ammonium.
Claim 2
Dependent Claim
202 words
A 2-hydroxyethylidene-cyano acetic acid aniline of the formula ##STR20## wherein each of R 1 , R 2 and R 3 , is alkyl of from 1 to 3 carbon atoms, alkoxy of from 1 to 3 carbon atoms, alkylthio of from 1 to 3 carbon atoms; said alkyl, alkoxy or alkylthio substituted in the alkyl moiety by halogen; halogen; nitro; cyano or alkoxycarbonyl of 1 to 3 carbon atoms in the alkyl moiety; also wherein either or both of R 1 and R 2 are hydrogen, and R 3 additionally is phenyl; phenyl substituted by one or two fluorine, chlorine, bromine or iodine atoms, alkyl of from 1 to 3 carbon atoms or alkoxy of from 1 to 3 carbon atoms; phenoxy; or phenoxy substituted by one or two fluorine, chlorine, bromine or iodine atoms, alkyl of from 1 to 3 carbon atoms or alkoxy of from 1 to 3 carbon atoms; but R 3 is not methyl when both R 1 and R 2 are hydrogen; or R 1 is hydrogen, and R 2 and R 3 together are methylene-dioxy or, together with the phenyl ring to which they are linked, naphthalene; and M is hydrogen, an alkali metal or ammonium.
Claim 3
Dependent Claim
22 words
A compound defined in claim 1, wherein R 1 is hydrogen, and R 2 and R 3 each is halogen or trifluoro-methyl.
Claim 4
Dependent Claim
26 words
A compound defined in claim 1, wherein R 1 is hydrogen, R 2 is alkyl of 1 to 2 carbon atoms and R 3 is halogen.
Claim 5
Dependent Claim
20 words
A compound defined in claim 1, wherein R 1 is hydrogen and R 2 and R 3 together are 3,4-methylene-dioxy.
Claim 6
Dependent Claim
65 words
A process for the manufacture of a compound as defined in claim 1, which comprises treating an isoxazole of the formula ##STR21## wherein R 1 , R 2 and R 3 have the meaning assigned in claim 1, with a base and optionally reacting the resulting alkali metal or ammonium compound as defined in claim 1 with a mineral acid or a strong organic acid.
Claim 7
Dependent Claim
23 words
The process defined in claim 5, wherein said isoxazole is treated with the base at a temperature of from -10° to +100° C.
Claim 8
Dependent Claim
28 words
A pharmaceutical composition consisting essentially of an effective amount of a compound as defined in claim 1 in admixture or conjunction with a pharmaceutically acceptable carrier and/or constituent.
Claim 9
Dependent Claim
24 words
A method of combatting pains and/or inflammations which comprises administering to a patient an effective amount of a compound as defined in claim 1.
References Cited (Backward Citations)
US2288863A
Cited
US2721799A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-05 | 1981-06-06 | 1981-12-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-05 | 1985-06-06 | 1985-12-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-05 | 1989-06-06 | 1989-12-06 | $7700.00 | Window Closed / Lapsed |