CA1094564A - Isoxazole derivatives and process for their manufacture - Google Patents
Isoxazole derivatives and process for their manufactureInfo
- Publication number
- CA1094564A CA1094564A CA292,276A CA292276A CA1094564A CA 1094564 A CA1094564 A CA 1094564A CA 292276 A CA292276 A CA 292276A CA 1094564 A CA1094564 A CA 1094564A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- group
- carbon atoms
- formula
- carboxylic acid
- 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
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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
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- 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
Abstract of the Disclosure:
5-Methylisoxazcle-4-carboxylic acid anilides of the general formula
5-Methylisoxazcle-4-carboxylic acid anilides of the general formula
Description
10~4S6~
The subject matter of our co-pending Canadian patent application Serial Number 254,134 is 5-methylisoxazole-4-carboxy-lic acid anilides of the general formula S ~ CON11~
in which any two or more of Rl, R2 and R3 may be the same or different and each represents an alkyl radical having l, 2 or 3 carbon atoms, an alkoxy radical having l, 2 or 3 carbon atoms, or an alkylthio radical having l,
The subject matter of our co-pending Canadian patent application Serial Number 254,134 is 5-methylisoxazole-4-carboxy-lic acid anilides of the general formula S ~ CON11~
in which any two or more of Rl, R2 and R3 may be the same or different and each represents an alkyl radical having l, 2 or 3 carbon atoms, an alkoxy radical having l, 2 or 3 carbon atoms, or an alkylthio radical having l,
2 or 3 carbon atoms, each of which radicals may be unsubstituted or completely or partially substituted by the same or different halogen atoms, such as fluorine, chlorine, bromine or iodine atoms;
a halogen atom, such as a fluorine, chlorine, bromine or iodine atom;
a nitro group;
a cyano group; or an alkoxycarbonyl radical having l, 2 or 3 carbon atoms in the alky moiety;
and in which R and R may furthermore represent hydrogen atoms, in which case R3 cannot represent a methyl group, but addition-ally may represent a phenyl radical which may be unsubstituted or substituted in each case once or twice by a fluorine, chlorine, bromine or iodine atom, by an alkyl radical having l, 2 or 3 carbon atoms, or by an alkoxy radical having l, 2 or 3 carbon atoms, or may represent a phenoxy radical which may be unsubstituted or substituted in each case once or twice by a ~k 10'34S6~
fluorine, chlorine, bromine or iodine atom, by an alkyl radical having 1, 2 or 3 carbon atoms or by an alkoxy radical having 1, 2 or 3 carbon atoms;
or in which Rl represents a hydrogen atom and R2 and R3 together represent a methylenedioxy group or, together with the phenyl ring carrying them, a naphthalene ring.
In a further development on the subject of the afore-said specification, new pharmacologically active 5-methylisoxa-zole-4-carboxylic acid anilides of the general formula I have been found in which one, two or all of the radicals Rl to R3 now represent a carboxy and/or hydroxy group or groups and the re-maining group or groups, if any, have the meanings given above.
Preferred compounds are those of the general formula I, in which either Rl represents a hydrogen atom or a halogen atom, such as a fluQrine, chlorine, bromine or iodine atom, or a tri-fluoromethyl group, and R3 represents a carboxy group, or represents a hydroxy group and R3 a halogen atom such as a flo~urine, chlorine, bromine or iodine atom, a trifluoromethyl or carboxy group, and R2 in each case represents a hydrogen atom.
The process for the manufacture ofthe compounds accord-ing to ~he invention of the general formula I comprises reacting a 5-methylisoxazole-4-carboxylic acid derivative of the general formula ,~0 2 5 N~(~ C \X I I
`O CH 3 in which X represents a) a halogen atom, preferably a chlorine or bromine atom;
b) a YO- group in which Y represents 109'~5fi4 (i~ a phenyl radical which is unsubstituted or substituted once, twice or three times by a fluorine, chlorine, bromine or iodine atom, or by a methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro or cyano group, or (ii) the acyl radical corresponding to the formula II; or c) a ZO-CO-O- group in which Z represents a (Cl-C4)-alkyl radical or a phenyl or benzyl radical;
with an aniline of the general formula 2 ~ R2 III
in which Rl, R2 and R3 have the meanings given above.
The reaction is advantageously carried out in a dispers-ing agent or solvent that is inert towards the reactants, for example in a nitrile, such as acetonitrile; and ether, such as diethyl ether, tetrahydrofuran or dioxan; or an alcohol, such as methanol, ethanol, propanol or isopropanol.
A preferred process for the preparation ofthe compounds according to theinvention of the general formula I is the reaction of the carboxylic acid chloride ofthe formula II with an aniline of the general formula III. It has proved advantageous in this case for the reaction to be carried out in the presence ofan acid binding agent, such as potassium or sodium carbonate, an alkali metal hydroxide or alcoholate, an alkaline earth metal hydroxide or alcoholate, an organic base, for example triethylamine, pyridine, picoline or quinoline, or the aniline reactant used in excess, at temperatures of from 0 to 160C, preferably from 20 to 80C. The reaction time may be from a few minutes to two hours.
A 5-methylisoxazole-4-carboxylic acid derivative of the lO9 ~S64 general formula II requlred as starting material may be obtained in accordance with German Patent 634 286 by reacting ethoxymethyli-deneacetoacetic ester with hydroxylamine to form the 5-methyliso-xazole-4-carboxylic acid ester, by acid hydrolysis of the ester so obtained, preferably with a mixture of glacial acetic acid and concentrated hydrochloric acid in the ratio l : 1 to form 5-methylisoxazole-4-carboxylic acid, and converting this carboxylic acid according to customary methods into a carboxylic acid halide, ester or mixed anhydride.
The following are examples of carboxylic acid deriva-tives of the general formula II:
5-methylisoxazole-4-carboxylic acid phenyl esters, especially the 2,4-dichlorophenyl ester or the 2,4,6-trichlorophenyl ester; and 5-methylisoxazole-4-carboxylic acid anhydrides, especially those in which X represents the methoxycarbonyloxy radical, the ethoxy-carbonyloxy radical, the phenoxycarbonyloxy radical or the benzyloxycarbonyloxy radical.
The following Examples illustrate the invention:
Manufacturing Examples l. 5~methylisoxazole-4-carboxylic acid 2-carboxy-4-chloroanilide of the general formula I
a) A solution of 0.05 mole of 5-methylisoxazole-4-carboxylic acid chloride of the formula II (7.3 g) in 20 ml of tetrahydro-furan is added dropwise at room temperature, while stirring, to 0.1 mole of 2-amino-5-chlorobenzoic acid of the formula III
(17.2 g) dissolved in 200 ml of tetrahydrofuran. After stirring for a further 20 minutes the precipitate that has formed is suction-filtered off and extracted by boiling with 200 ml of 2N
hydrochloric acid. The remaining precipitate is suction-filtered .
lO~ S64 off, washed with water until neutral, and dried. In this manner 13.1 g (93 % of the theoretical yield) of a colorless crystalline powder are obtained; melting point after recrystallization from ethanol: 240 to 243C (with decomposition).
b) 0.1 mole of 2-amino~5-chlorobenzoic acid of the formula III (17.2 g) and 0.1 mole of 4-fluorophenyl 5-methylisoxazole-4-carboxylate of the formula II (22.1 g) dissolved in 100 ml of tetrahydrofuran are refluxed for 80 minutes. Subsequently the precipitate is suction-filtered off and extracted by boiling with 200 ml of 2N hydrochloric acid. The remaining precipitate is suction-filtered off, washed with water until neutral and dried. In this manner 19.4 g (69 % of the theoretical yield) of crystalline powder having a melting point (after recrystalliza-tion from ethanol) of 240 to 243C (with decomposition) are lS obtained.
c) 0.1 mole of 2-amino-5-chlorobenzoic acid of the formula III (17.2 g) and 0.1 mole of methoxycarbonyl-5-methylisoxazole-4-carboxylate ofthe formula II (18.5 g) dissolved in 150 ml of tetrahydrofuran are refluxed for 70 minutes. Subsequently the precipitate that has formed is suction-filtered off and extracted by boiling with 200 ml of 2N hydrochloric acid. The remaining precipitate is suction-filtered off, washed with water until neutral and dried. In this manner 20.2 g (72 % of the theoreti-cal yield) of a crystalline powder having a melting point (after recrystallization from ethanol) of 240 to 243~C are obtained.
The compounds listed in Table 1 were prepared in accor-dance with the process described above.
10~'15fi4 Table 1: 5-methylisoxazole-4-carboxylic acid anilides of the general formula I
No. R R2 R3 Melting point C
a halogen atom, such as a fluorine, chlorine, bromine or iodine atom;
a nitro group;
a cyano group; or an alkoxycarbonyl radical having l, 2 or 3 carbon atoms in the alky moiety;
and in which R and R may furthermore represent hydrogen atoms, in which case R3 cannot represent a methyl group, but addition-ally may represent a phenyl radical which may be unsubstituted or substituted in each case once or twice by a fluorine, chlorine, bromine or iodine atom, by an alkyl radical having l, 2 or 3 carbon atoms, or by an alkoxy radical having l, 2 or 3 carbon atoms, or may represent a phenoxy radical which may be unsubstituted or substituted in each case once or twice by a ~k 10'34S6~
fluorine, chlorine, bromine or iodine atom, by an alkyl radical having 1, 2 or 3 carbon atoms or by an alkoxy radical having 1, 2 or 3 carbon atoms;
or in which Rl represents a hydrogen atom and R2 and R3 together represent a methylenedioxy group or, together with the phenyl ring carrying them, a naphthalene ring.
In a further development on the subject of the afore-said specification, new pharmacologically active 5-methylisoxa-zole-4-carboxylic acid anilides of the general formula I have been found in which one, two or all of the radicals Rl to R3 now represent a carboxy and/or hydroxy group or groups and the re-maining group or groups, if any, have the meanings given above.
Preferred compounds are those of the general formula I, in which either Rl represents a hydrogen atom or a halogen atom, such as a fluQrine, chlorine, bromine or iodine atom, or a tri-fluoromethyl group, and R3 represents a carboxy group, or represents a hydroxy group and R3 a halogen atom such as a flo~urine, chlorine, bromine or iodine atom, a trifluoromethyl or carboxy group, and R2 in each case represents a hydrogen atom.
The process for the manufacture ofthe compounds accord-ing to ~he invention of the general formula I comprises reacting a 5-methylisoxazole-4-carboxylic acid derivative of the general formula ,~0 2 5 N~(~ C \X I I
`O CH 3 in which X represents a) a halogen atom, preferably a chlorine or bromine atom;
b) a YO- group in which Y represents 109'~5fi4 (i~ a phenyl radical which is unsubstituted or substituted once, twice or three times by a fluorine, chlorine, bromine or iodine atom, or by a methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro or cyano group, or (ii) the acyl radical corresponding to the formula II; or c) a ZO-CO-O- group in which Z represents a (Cl-C4)-alkyl radical or a phenyl or benzyl radical;
with an aniline of the general formula 2 ~ R2 III
in which Rl, R2 and R3 have the meanings given above.
The reaction is advantageously carried out in a dispers-ing agent or solvent that is inert towards the reactants, for example in a nitrile, such as acetonitrile; and ether, such as diethyl ether, tetrahydrofuran or dioxan; or an alcohol, such as methanol, ethanol, propanol or isopropanol.
A preferred process for the preparation ofthe compounds according to theinvention of the general formula I is the reaction of the carboxylic acid chloride ofthe formula II with an aniline of the general formula III. It has proved advantageous in this case for the reaction to be carried out in the presence ofan acid binding agent, such as potassium or sodium carbonate, an alkali metal hydroxide or alcoholate, an alkaline earth metal hydroxide or alcoholate, an organic base, for example triethylamine, pyridine, picoline or quinoline, or the aniline reactant used in excess, at temperatures of from 0 to 160C, preferably from 20 to 80C. The reaction time may be from a few minutes to two hours.
A 5-methylisoxazole-4-carboxylic acid derivative of the lO9 ~S64 general formula II requlred as starting material may be obtained in accordance with German Patent 634 286 by reacting ethoxymethyli-deneacetoacetic ester with hydroxylamine to form the 5-methyliso-xazole-4-carboxylic acid ester, by acid hydrolysis of the ester so obtained, preferably with a mixture of glacial acetic acid and concentrated hydrochloric acid in the ratio l : 1 to form 5-methylisoxazole-4-carboxylic acid, and converting this carboxylic acid according to customary methods into a carboxylic acid halide, ester or mixed anhydride.
The following are examples of carboxylic acid deriva-tives of the general formula II:
5-methylisoxazole-4-carboxylic acid phenyl esters, especially the 2,4-dichlorophenyl ester or the 2,4,6-trichlorophenyl ester; and 5-methylisoxazole-4-carboxylic acid anhydrides, especially those in which X represents the methoxycarbonyloxy radical, the ethoxy-carbonyloxy radical, the phenoxycarbonyloxy radical or the benzyloxycarbonyloxy radical.
The following Examples illustrate the invention:
Manufacturing Examples l. 5~methylisoxazole-4-carboxylic acid 2-carboxy-4-chloroanilide of the general formula I
a) A solution of 0.05 mole of 5-methylisoxazole-4-carboxylic acid chloride of the formula II (7.3 g) in 20 ml of tetrahydro-furan is added dropwise at room temperature, while stirring, to 0.1 mole of 2-amino-5-chlorobenzoic acid of the formula III
(17.2 g) dissolved in 200 ml of tetrahydrofuran. After stirring for a further 20 minutes the precipitate that has formed is suction-filtered off and extracted by boiling with 200 ml of 2N
hydrochloric acid. The remaining precipitate is suction-filtered .
lO~ S64 off, washed with water until neutral, and dried. In this manner 13.1 g (93 % of the theoretical yield) of a colorless crystalline powder are obtained; melting point after recrystallization from ethanol: 240 to 243C (with decomposition).
b) 0.1 mole of 2-amino~5-chlorobenzoic acid of the formula III (17.2 g) and 0.1 mole of 4-fluorophenyl 5-methylisoxazole-4-carboxylate of the formula II (22.1 g) dissolved in 100 ml of tetrahydrofuran are refluxed for 80 minutes. Subsequently the precipitate is suction-filtered off and extracted by boiling with 200 ml of 2N hydrochloric acid. The remaining precipitate is suction-filtered off, washed with water until neutral and dried. In this manner 19.4 g (69 % of the theoretical yield) of crystalline powder having a melting point (after recrystalliza-tion from ethanol) of 240 to 243C (with decomposition) are lS obtained.
c) 0.1 mole of 2-amino-5-chlorobenzoic acid of the formula III (17.2 g) and 0.1 mole of methoxycarbonyl-5-methylisoxazole-4-carboxylate ofthe formula II (18.5 g) dissolved in 150 ml of tetrahydrofuran are refluxed for 70 minutes. Subsequently the precipitate that has formed is suction-filtered off and extracted by boiling with 200 ml of 2N hydrochloric acid. The remaining precipitate is suction-filtered off, washed with water until neutral and dried. In this manner 20.2 g (72 % of the theoreti-cal yield) of a crystalline powder having a melting point (after recrystallization from ethanol) of 240 to 243~C are obtained.
The compounds listed in Table 1 were prepared in accor-dance with the process described above.
10~'15fi4 Table 1: 5-methylisoxazole-4-carboxylic acid anilides of the general formula I
No. R R2 R3 Melting point C
3 H 3-OH 4-COOH 228 - 231
4 H H 3-COOH 242 - 245 6 H 2-OH 5-COOH 231 - 234 (with decomposition) 7 H 2-OH 3-COOH 198 - 201 (with decomposition) 8 H 3-COOH 4-OH 247 - 251 (with decomposition) 9 H 2-COOH 4-OH 228 - 231 (with decomposition) H 2-COOH 4-C1 240 - 243 (with decomposition) 15 12 H 2-COOH 5-Br > 300 (with decomposition) 14 H 3-COO~ 4-C1 244 - 250 (with decomposition) 1. 5-Methylisoxazole-4-carboxylic acid 4-hydroxyanilide 2. 5-Methylisoxazole-4-carboxylic acid 4-carboxyanilide 3. 5-Methylisoxazole-4-carboxylic acid 4-carboxy-3-hydroxyanilide 4. 5-Methylisoxazole-4-carboxylic acid 3-carboxyanilide
5. 5-Methylisoxazole-4-carboxylic acid 2-carboxyanilide
6. 5-Methylisoxazole-4-carboxylic acid 5-carboxy-2-hydroxyanilide
7. 5-Methylisoxazole-4-carboxylic acid 3-carboxy-2-hydroxyanilide
8. 5-Methylisoxazole-4-carboxylic acid 3-carboxy-4-hydroxyanilide
9. 5-Methylisoxazole-4-carboxylic acid 2-carboxy-4-hydroxyanilide
10. 5-Methylisoxazole-4-carboxylic acid 2-carboxy-4-chloroanilide
11. 5-Methylisoxazole-4-carboxylic acid 4-chloro-2-hydroxyanilide ~O~S64
12. 5-Methylisoxazole-4-carboxylic acid 5-bromo-2-carboxyanilide
13. 5-Methylisoxazole-4-carboxylic acid 5-chloro-2-hydroxyanilide
14. 5-Methylisoxazole-4-carboxylic acid 3-carboxy-4-chloroanilide
Claims (6)
OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the preparation of a 5-methylisoxazole-4-carboxylic acid anilide of the general formula I
(I) wherein any two or more of R1, R2 and R3 may be the same or different and each represents an alkyl radical having 1, 2 or 3 carbon atoms, an alkoxy radical having 1, 2 or 3 carbon atoms, or an alkylthio radical having 1, 2 or 3 carbon atoms, each of which radicals may be unsubstituted or completely or partially substituted by the same or different halogen atoms;
a halogen atom;
a nitro group;
a cyano group; or an alkoxycarbonyl radical having 1, 2 or 3 carbon atoms in the alkyl moiety;
and wherein R1 and R2 may furthermore represent hydrogen atoms, in which case R3 cannot represent a methyl group, but additionally may represent a phenyl radical which may be unsubstituted or substituted in each case once or twice by a fluorine, chlorine, bromine or iodine atom, by an alkyl radical having 1, 2 or 3 carbon atoms, or by an alkoxy radical having 1, 2 or 3 carbon atoms, or may represent a phenoxy radical which may be unsubstituted or substituted in each case once or twice by a fluorine, chlorine, bromine or iodine atom, by an alkyl radical having 1, 2 or 3 carbon atoms or by an alkoxy radical having 1, 2 or 3 carbon atoms;
or wherein R1 represents a hydrogen atom and R2 and R3 together represent a methylenedioxy group or, together with the phenyl ring carrying them, a naphthalene ring, wherein one, two or all of the radicals R1 to R3 represents a carboxy group, a hydroxy group, or carboxy and hydroxy groups, and the remaining group or groups, if any, have the meanings given above, in which a 5-methylisoxazole-4-carboxylic acid derivative of the general formula II
(II) wherein X represents a) a halogen atom;
b) a YO- group in which Y represents (i) a phenyl radical which is unsubstituted or substituted once, twice or three times by a fluorine, chlorine, bromine, or iodine atom, or by a methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro or cyano group, or (ii) the acyl radical corresponding to the formula II; or c) a ZO-CO-O- group in which Z represents a (C1-C4)-alkyl radical or a phenyl or benzyl radical;
is reacted with an aniline of the general formula III
(III) wherein R1, R2 and R3 have the meanings given above.
(I) wherein any two or more of R1, R2 and R3 may be the same or different and each represents an alkyl radical having 1, 2 or 3 carbon atoms, an alkoxy radical having 1, 2 or 3 carbon atoms, or an alkylthio radical having 1, 2 or 3 carbon atoms, each of which radicals may be unsubstituted or completely or partially substituted by the same or different halogen atoms;
a halogen atom;
a nitro group;
a cyano group; or an alkoxycarbonyl radical having 1, 2 or 3 carbon atoms in the alkyl moiety;
and wherein R1 and R2 may furthermore represent hydrogen atoms, in which case R3 cannot represent a methyl group, but additionally may represent a phenyl radical which may be unsubstituted or substituted in each case once or twice by a fluorine, chlorine, bromine or iodine atom, by an alkyl radical having 1, 2 or 3 carbon atoms, or by an alkoxy radical having 1, 2 or 3 carbon atoms, or may represent a phenoxy radical which may be unsubstituted or substituted in each case once or twice by a fluorine, chlorine, bromine or iodine atom, by an alkyl radical having 1, 2 or 3 carbon atoms or by an alkoxy radical having 1, 2 or 3 carbon atoms;
or wherein R1 represents a hydrogen atom and R2 and R3 together represent a methylenedioxy group or, together with the phenyl ring carrying them, a naphthalene ring, wherein one, two or all of the radicals R1 to R3 represents a carboxy group, a hydroxy group, or carboxy and hydroxy groups, and the remaining group or groups, if any, have the meanings given above, in which a 5-methylisoxazole-4-carboxylic acid derivative of the general formula II
(II) wherein X represents a) a halogen atom;
b) a YO- group in which Y represents (i) a phenyl radical which is unsubstituted or substituted once, twice or three times by a fluorine, chlorine, bromine, or iodine atom, or by a methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro or cyano group, or (ii) the acyl radical corresponding to the formula II; or c) a ZO-CO-O- group in which Z represents a (C1-C4)-alkyl radical or a phenyl or benzyl radical;
is reacted with an aniline of the general formula III
(III) wherein R1, R2 and R3 have the meanings given above.
2. A compound of the formula I as defined in claim 1, whenever obtained according to a process as claimed in claim 1 or by an obvious chemical equivalent thereof.
3. A process as claimed in claim 1 for the preparation of a compound of the formula I wherein R1 represents a hydrogen or halogen atom or a trifluoromethyl group and R3 represents a carboxy group, or R1 represents a hydroxy group and R3 a halogen atom or a trifluoromethyl or carboxy group, while in each instance R2 represents a hydrogen atom.
4. A compound of the formula I as set forth in claim 1 wherein R1, R2 and R3 are as defined in claim 3, whenever obtained according to a process as claimed in claim 3 or by an obvious chemical equivalent thereof.
5. A process as claimed in claim 1 in which the compound of the formula II is 5-methyl-4-carboxylic acid chloride and the reaction is carried out in the presence of an acid binding agent.
6. A compound of the formula I as defined in claim 1, whenever obtained according to a process as claimed in claim 5 or by an obvious chemical equivalent thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2655094.7 | 1976-12-04 | ||
| 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 |
|---|---|
| CA1094564A true CA1094564A (en) | 1981-01-27 |
Family
ID=5994722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA292,276A Expired CA1094564A (en) | 1976-12-04 | 1977-12-02 | Isoxazole derivatives and process for their manufacture |
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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55500866A (en) * | 1978-11-03 | 1980-10-30 | ||
| 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 |
| 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 |
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 DK DK538577A patent/DK538577A/en unknown
- 1977-12-02 GB GB5034677A patent/GB1595467A/en not_active Expired
- 1977-12-02 AT AT0866277A patent/AT362788B/en not_active IP Right Cessation
- 1977-12-02 IE IE245177A patent/IE46102B1/en unknown
- 1977-12-02 CA CA292,276A patent/CA1094564A/en not_active Expired
- 1977-12-02 IT IT3035177A patent/IT1113801B/en active
- 1977-12-02 LU LU78626A patent/LU78626A1/xx unknown
- 1977-12-03 JP JP14562177A patent/JPS5371069A/en active Pending
- 1977-12-05 BE BE183169A patent/BE861502R/en not_active IP Right Cessation
- 1977-12-05 FR FR7736546A patent/FR2372813A2/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1595467A (en) | 1981-08-12 |
| DK538577A (en) | 1978-06-05 |
| JPS5371069A (en) | 1978-06-24 |
| CH614945A5 (en) | 1979-12-28 |
| BE861502R (en) | 1978-06-05 |
| ATA866277A (en) | 1980-11-15 |
| IT1113801B (en) | 1986-01-27 |
| ES464553A2 (en) | 1979-08-01 |
| LU78626A1 (en) | 1978-07-11 |
| IE46102L (en) | 1978-06-04 |
| NL7713148A (en) | 1978-06-06 |
| AT362788B (en) | 1981-06-10 |
| FR2372813A2 (en) | 1978-06-30 |
| FR2372813B2 (en) | 1980-06-20 |
| DE2655094A1 (en) | 1978-06-15 |
| IE46102B1 (en) | 1983-02-23 |
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