ES464553A2 - 5-methyliso-oxazole-4-carboxylic acid anilides having pharmaceutical activity - Google Patents
5-methyliso-oxazole-4-carboxylic acid anilides having pharmaceutical activityInfo
- Publication number
- ES464553A2 ES464553A2 ES464553A ES464553A ES464553A2 ES 464553 A2 ES464553 A2 ES 464553A2 ES 464553 A ES464553 A ES 464553A ES 464553 A ES464553 A ES 464553A ES 464553 A2 ES464553 A2 ES 464553A2
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- carboxylic acid
- denote
- methyliso
- oxazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical class CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 abstract 1
- ZYEWRBNSDKQNSJ-UHFFFAOYSA-N 5-methyl-n-phenyl-1,2-oxazole-4-carboxamide Chemical class O1N=CC(C(=O)NC=2C=CC=CC=2)=C1C ZYEWRBNSDKQNSJ-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel 5-methyl-isoxazole-4-carboxylic acid anilides of the formula I < IMAGE > wherein one, two or three of the radicals R1, R2 and R3 denote a carboxyl group and/or a hydroxyl group and the remaining radicals R1, R2 and R3, which may be identical or different, denote alkyl having 1, 2 or 3 carbon atoms, alkoxy having 1, 2 and 3 carbon atoms or alkylthio having 1, 2 or 3 carbon atoms, which groups may each be completely or partially substituted by identical or different halogen atoms, or denote hydrogen, halogen, nitro, cyano or carbalkoxy having 1, 2 or 3 carbon atoms in the alkyl group, are prepared by reacting a 5-methyl-isoxazole-4-carboxylic acid derivative with an appropriately substituted aniline. The compounds of the formula I are pharmacologically active. They exhibit a powerful antiphlogistic, antipyretic and analgesic action. Their toxicity is low and their gastric toleration is good.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655094 DE2655094A1 (en) | 1976-12-04 | 1976-12-04 | ISOXAZOLE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND THE PRODUCTS CONTAINING THE SAME |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES464553A2 true ES464553A2 (en) | 1979-08-01 |
Family
ID=5994722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES464553A Expired ES464553A2 (en) | 1976-12-04 | 1977-11-29 | 5-methyliso-oxazole-4-carboxylic acid anilides having pharmaceutical activity |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5371069A (en) |
| AT (1) | AT362788B (en) |
| BE (1) | BE861502R (en) |
| CA (1) | CA1094564A (en) |
| CH (1) | CH614945A5 (en) |
| DE (1) | DE2655094A1 (en) |
| DK (1) | DK538577A (en) |
| ES (1) | ES464553A2 (en) |
| FR (1) | FR2372813A2 (en) |
| GB (1) | GB1595467A (en) |
| IE (1) | IE46102B1 (en) |
| IT (1) | IT1113801B (en) |
| LU (1) | LU78626A1 (en) |
| NL (1) | NL7713148A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035285A3 (en) * | 1979-08-17 | 1981-10-14 | American Cyanamid Company | Novel isoxazole carboxylic acid phenyl esters, pharmaceutical compositions containing certain of said esters, and process for preparing said esters |
| WO1980000964A1 (en) * | 1978-11-03 | 1980-05-15 | American Cyanamid Co | Anti-inflammatory agents including 2-carbonyl-3-hydroxy-2-alkenonitriles |
| DE3247454A1 (en) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituted 3-phenyl-5-methylisoxazole-4-carboxanilides, process for their preparation and pharmaceutical compositions containing these compounds |
| FR2538806B1 (en) * | 1982-12-30 | 1986-02-21 | Bago Sa Labor | PHENYL-3 METHYL ISOXAZOLE-5 CARBOXY-4 COMPOUNDS SUBSTITUTED ANILIDES, THERAPEUTICALLY ACTIVE INFLAMMATION AND PAIN |
| US20040110802A1 (en) * | 2002-08-23 | 2004-06-10 | Atli Thorarensen | Antibacterial benzoic acid derivatives |
| WO2026057018A1 (en) * | 2024-09-12 | 2026-03-19 | Fulcrum Therapeutics, Inc. | Nox inhibitors and methods of use thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2126329A (en) * | 1936-03-20 | 1938-08-09 | Hoffmann La Roche | Amide derivatives of isoxazole carboxylic acids |
| US2288863A (en) * | 1940-02-27 | 1942-07-07 | Hoffmann La Roche | Process for the manufacture of substituted amides of 3,5-dimethylisoxazole-4-carboxylic acid |
-
1976
- 1976-12-04 DE DE19762655094 patent/DE2655094A1/en not_active Withdrawn
-
1977
- 1977-11-15 CH CH1393377A patent/CH614945A5/en not_active IP Right Cessation
- 1977-11-29 NL NL7713148A patent/NL7713148A/en not_active Application Discontinuation
- 1977-11-29 ES ES464553A patent/ES464553A2/en not_active Expired
- 1977-12-02 AT AT0866277A patent/AT362788B/en not_active IP Right Cessation
- 1977-12-02 DK DK538577A patent/DK538577A/en unknown
- 1977-12-02 GB GB5034677A patent/GB1595467A/en not_active Expired
- 1977-12-02 IT IT3035177A patent/IT1113801B/en active
- 1977-12-02 LU LU78626A patent/LU78626A1/xx unknown
- 1977-12-02 IE IE245177A patent/IE46102B1/en unknown
- 1977-12-02 CA CA292,276A patent/CA1094564A/en not_active Expired
- 1977-12-03 JP JP14562177A patent/JPS5371069A/en active Pending
- 1977-12-05 FR FR7736546A patent/FR2372813A2/en active Granted
- 1977-12-05 BE BE183169A patent/BE861502R/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1595467A (en) | 1981-08-12 |
| CA1094564A (en) | 1981-01-27 |
| IT1113801B (en) | 1986-01-27 |
| FR2372813B2 (en) | 1980-06-20 |
| CH614945A5 (en) | 1979-12-28 |
| BE861502R (en) | 1978-06-05 |
| JPS5371069A (en) | 1978-06-24 |
| DE2655094A1 (en) | 1978-06-15 |
| IE46102B1 (en) | 1983-02-23 |
| IE46102L (en) | 1978-06-04 |
| AT362788B (en) | 1981-06-10 |
| LU78626A1 (en) | 1978-07-11 |
| ATA866277A (en) | 1980-11-15 |
| FR2372813A2 (en) | 1978-06-30 |
| NL7713148A (en) | 1978-06-06 |
| DK538577A (en) | 1978-06-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 20100616 |