DE2655094A1 - ISOXAZOLE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND THE PRODUCTS CONTAINING THE SAME - Google Patents
ISOXAZOLE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND THE PRODUCTS CONTAINING THE SAMEInfo
- Publication number
- DE2655094A1 DE2655094A1 DE19762655094 DE2655094A DE2655094A1 DE 2655094 A1 DE2655094 A1 DE 2655094A1 DE 19762655094 DE19762655094 DE 19762655094 DE 2655094 A DE2655094 A DE 2655094A DE 2655094 A1 DE2655094 A1 DE 2655094A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- carbon atoms
- bromine
- chlorine
- 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.)
- Withdrawn
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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)
Description
Isoxazolderivate, Verfahren zu ihrer Herstellung und diese Verbindungen
enthaltende Mittel
Zusatz zu Patentanmeldung P 25 24 959.5 (HOE 75/F 149)Isoxazole derivatives, processes for their preparation and compositions containing these compounds
Addition to patent application P 25 24 959.5 (HOE 75 / F 149)
Gegenstand der Hauptanmeldung P 25 24 959.5 (HOE 75/F 149jsind 5-Methyl-isoxazol-4-carbonsäureanilide der Formel IThe subject of the main application P 25 24 959.5 (HOE 75 / F 149jsind 5-methyl-isoxazole-4-carboxylic acid anilides of the formula I
(D(D
worin R1, R2 und R3 gleich oder verschieden sein können und Alkyl mit 1, 2 oder 3 C-Atomen, Alkoxy mit 1, 2 oder 3 C-Atomen, Alkylthio mit 1, 2 oder 3 C-Atomen, welche Gruppen jeweils vollständig oder teilweise durch gleiche oder verschiedene Halogenatome, wie Fluor, Chlor, Brom oder Jod, substituiert sein können, Halogen, wie Fluor, Chlor, Brom oder Jod, Nitro, Cyan, Carbalk-wherein R 1 , R 2 and R 3 can be identical or different and alkyl with 1, 2 or 3 carbon atoms, alkoxy with 1, 2 or 3 carbon atoms, alkylthio with 1, 2 or 3 carbon atoms, which groups each completely or partially by identical or different halogen atoms, such as fluorine, chlorine, bromine or iodine, can be substituted, halogen, such as fluorine, chlorine, bromine or iodine, nitro, cyano, carbalk-
80 9 824/0044 /2 80 9 824/0044 / 2
oxy mit 1, 2 oder 3 C-Atomen in der Alkylgruppe, bedeuten, worinoxy with 1, 2 or 3 carbon atoms in the alkyl group, mean in which
" 1 2"1 2
R und R weiterhin Wasserstoff bedeuten, in welchem Fall jedochR and R continue to represent hydrogen, but in which case
3 33 3
R nicht Methyl sein kann, in welchem Fall jedoch R zusätzlich Phenyl, das gegebenenfalls jeweils einfach oder zweifach durch Fluor, Chlor, Brom, Jod, Alkyl mit 1, 2 oder 3 C-Atomen oder Alkoxy mit 1,2 oder 3 C-Atomen substituiert sein kann, oder Phenoxy, das gegebenenfalls jeweils einfach oder zweifach durch Fluor,. Chlor, Brom, Jod, Alkyl mit 1, 2 oder 3 C-Atomen oder Alkoxy rait 1, 2 oder 3 C-Atomen substituiert sein kann, bedeutet,R cannot be methyl, but in which case R can also be phenyl, which is optionally single or double Fluorine, chlorine, bromine, iodine, alkyl with 1, 2 or 3 carbon atoms or Alkoxy can be substituted by 1,2 or 3 carbon atoms, or Phenoxy, which is optionally in each case once or twice by fluorine ,. Chlorine, bromine, iodine, alkyl with 1, 2 or 3 carbon atoms or Alkoxy may be substituted with 1, 2 or 3 carbon atoms, means
1 7 31 7 3
oder worin R Wasserstoff bedeutet und R und R gemeinsam eine Methylendioxy-Gr-uppe oder gemeinsam mit dem sie tragenden Phenylring einen Naphthalinring bedeuten.or in which R is hydrogen and R and R together are one Methylenedioxy group or together with the phenyl ring carrying them mean a naphthalene ring.
In weiterer Ausbildung des Gegenstandes der Hauptanmeldung wurden nun neue pharmakologisch wirksame 5-Methyl-isoxazol-4-carbonsäureanilide der Formel I gefunden, bei denen einer,, zwei oderIn a further development of the subject matter of the main application, new pharmacologically active 5-methyl-isoxazole-4-carboxylic acid anilides were now used of the formula I found in which one ,, two or
1 3
drei der Reste R bis R neben der oben angegebenen Bedeutung für die übrigen Gruppen nunmehr auch Carboxyl- und /oder Hydroxyl-Gruppen
darstellen.1 3
three of the radicals R to R now also represent carboxyl and / or hydroxyl groups in addition to the meaning given above for the other groups.
Bevorzugt sind Verbindungen der Formel I, worin entweder RPreference is given to compounds of the formula I in which either R
wie
Wasserstoff, Halogen, Fluor, Chlor, Brom oder Jod oder Trifluor-how
Hydrogen, halogen, fluorine, chlorine , bromine or iodine or trifluorine
2 1 22 1 2
methyl und R Carboxyl, oder R Hydroxyl und R Halogen wie Fluor, Chlor, Brom oder Jod, Trifluormethyl oder Carboxyl sind, und R jeweils Wasserstoff bedeutet.methyl and R carboxyl, or R hydroxyl and R halogen such as Are fluorine, chlorine, bromine or iodine, trifluoromethyl or carboxyl, and each R is hydrogen.
Das Verfahren zur Herstellung der erfindungsgemäßen Verbindungen der Formel I ist dadurch gekennzeichnet, daß man ein 5-Methylisoxazol-4-carbonsäure-Derivat der Formel IIThe process for making the compounds of the invention of the formula I is characterized in that a 5-methylisoxazole-4-carboxylic acid derivative is used of formula II
CU)CU)
in der X ein Balogenatom, vorzugsweise Chlor oder Brom, eine YO- oder ZO-CO-O-Gruppe bedeutet; wobei Y für gegebenenfalls durchin which X is a balogen atom, preferably chlorine or bromine, a YO- or ZO-CO-O- group; where Y for optionally through
809824/00 4 4809824/00 4 4
Fluor, Chlor, Brom, Jod, Methyl, Äthyl, Methoxy, Äthoxy, Trifluormethyl, Nitro oder Cyan"einfach, zweifach oder dreifach substituiertes Phenyl oder für den Äcylrest entsprechend der Formel II und Z für (C1-C4I-AIlCyI, Phenyl oder Benzyl stehen, mit einem Anilin der Formel IIIFluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, nitro or cyano "single, double or triple substituted phenyl or for the acyl radical according to formula II and Z for (C 1 -C 4 I-AIlCyI, Phenyl or benzyl, with an aniline of the formula III
(III)(III)
12 312 3
worin R , R und R die vorgenannten Bedeutungen haben, umsetzt.wherein R, R and R have the meanings given above.
Die Reaktion wird zweckmäßig in einem Verteilungs- oder Lösungsmittel durchgeführt, das sich gegenüber den Reaktionspartnern indifferent verhält. Hierfür kommen beispielsweise Nitrile, wie Acetonitril, Äther, wie Diäthyiäther, Tetrahydrofuran oder Dioxan und Alkohole, wie Methanol, Äthanol, Propanol oder Isopropanol infrage.The reaction is conveniently carried out in a partition or solvent carried out, which behaves indifferently towards the reaction partners. For example, nitriles such as Acetonitrile, ethers, such as diethyl ether, tetrahydrofuran or Dioxane and alcohols such as methanol, ethanol, propanol or isopropanol in question.
Bevorzugtes Verfahren zur Darstellung der erfindungsgemäßen Verbindungen der Formel I ist die Umsetzung des Carbonsäurechlorids der Formel II mit einem Anilin der Formel III. Dabei erweist es sich als vorteilhaft, die Umsetzung in Gegenwart von säurebindenden Mitteln, wie Kalium- oder Natriumcarbonat, Alkalioder Erdalkalihydroxiden oder -alkoholaten, organischen Basen, beispielsweise Triäthylaminf Pyridin, Picolin oder Chinolin oäer dem jeweiligen im Überschuß eingesetzten Anilin bei Temperaturen zwischen 0 und 1600C, vorzugsweise zwischen 20 und 8O0C durchzuführen. Die Reaktionszeiten können von wenigen Minuten bis zu zwei Stunden betragen.The preferred method for preparing the compounds of the formula I according to the invention is the reaction of the carboxylic acid chloride of the formula II with an aniline of the formula III. It proves to be advantageous to carry out the reaction in the presence of acid-binding agents, such as potassium or sodium carbonate, alkali or alkaline earth metal hydroxides or alcoholates, organic bases, for example triethylamine f pyridine, picoline or quinoline or the respective aniline used in excess at temperatures between 0 and preferably perform 160 0 C between 20 and 8O 0 C. The reaction times can range from a few minutes to two hours.
Die als Ausgangsstoffe benötigten 5~Methyl-isoxazol-4-carbonsäure-Derivate der Formel II werden entsprechend DRP 634 286 durch Umsetzung von Athoxymethylidenacetessigester mit Hydroxylamin zum 5-Methylisoxasol-4-carbonsäureesteri. saures Verseifen des soThe 5-methyl-isoxazole-4-carboxylic acid derivatives required as starting materials of formula II are according to DRP 634 286 by reacting Athoxymethylidenacetoessigester with hydroxylamine to 5-methylisoxasol-4-carboxylic acid ester i. acid saponification of the so
809824/0044 /4 809824/0044 / 4
erhaltenen Esters, vorzugsweise einem Gemisch aus Eisessig und
konzentrierter Salzsäure im Verhältnis 1:1, zur 5-Methylisoxazol-4-carbonsäure
und überführen dieser Carbonsäure nach üblichen Methoden in die Carbonsäurehalogenide, Ester oder gemischten Anhydride,
erhalten.obtained ester, preferably a mixture of glacial acetic acid and
concentrated hydrochloric acid in a ratio of 1: 1 to 5-methylisoxazole-4-carboxylic acid and convert this carboxylic acid into the carboxylic acid halides, esters or mixed anhydrides by customary methods.
Als Carbonsäure-Derivate der Formel II kommen in Betracht:
5-Methylisoxazol-4-carbonsäurephenylester, insbesondere der 2,4-Dichlorphenylester
oder der 2,4,6-Trichlorphenylester, weiterhin
5-Methylisoxazol-4-carbonsäureanhydride, insbesondere solche in denen X den Methoxycarbonyloxyrest, den Äthoxycarbonyloxyrest,
den Phenoxycarbonyloxyrest oder den Benzyloxycarbonyloxyrest bedeuten .Possible carboxylic acid derivatives of the formula II are:
5-methylisoxazole-4-carboxylic acid phenyl ester, in particular the 2,4-dichlorophenyl ester or the 2,4,6-trichlorophenyl ester, furthermore 5-methylisoxazole-4-carboxylic acid anhydrides, especially those in which X is the methoxycarbonyloxy radical, the ethoxycarbonyloxy radical, the phenoxycarbonyloxy radical or the phenoxycarbonyloxy radical mean .
80 98 2 k /004 U-. 80 98 2 k / 004 U-.
HerstellungsbeispieleManufacturing examples
1. 5-Methylisoxazol-4-carbonsäure-(2-carboxy-4-chlor)-anilid der Formel I1. 5-Methylisoxazole-4-carboxylic acid (2-carboxy-4-chloro) anilide der Formula I.
a) 0,1 Mol 2-Amino-5-chlorbenzoesäure der Formel III (17,2 g) gelöst in 200 ml Tetrahydrofuran, werden bei Raumtemperatur tropfenweise mit einer Lösung von 0,05 Mol 5-Methylisoxazol-4-carbonsäurechlorid der Formel II (7,3 g) in 20 ml Tetrahydrofuran unter Rühren versetzt. Nach 20 Minuten weiteren Rührens wird der ausgefallene Niederschlag abgesaugt und mit 200 ml 2 η Salzsäure ausgekocht. Der zurückbleibende Niederschlag wird abgesaugt, mit Wasser neutral gewaschen und getrocknet. Man erhält so 13,1 g (S3 % der Theorie) eines kristallinen farblosen Pulvers; Schmelzpunkt nach Umkristalisieren aus Äthanol: 240 bis 243°C (Zers.).a) 0.1 mol of 2-amino-5-chlorobenzoic acid of the formula III (17.2 g) dissolved in 200 ml of tetrahydrofuran are at room temperature dropwise with a solution of 0.05 mol of 5-methylisoxazole-4-carboxylic acid chloride of the formula II (7.3 g) in 20 ml of tetrahydrofuran are added with stirring. After another 20 minutes While stirring, the precipitate is filtered off and boiled with 200 ml of 2 η hydrochloric acid. The remaining precipitate is filtered off with suction, washed neutral with water and dried. 13.1 g (S3% of theory) are obtained in this way crystalline colorless powder; Melting point after recrystallization from ethanol: 240 to 243 ° C (decomp.).
b) 0,1 Mol 2-Amino-5-chlorbenzoesäure der Formel III (17,2 g) und 0,1 Mol (4-Fluor)phenyl 5-Methylisoxazol-4-carboxylat der Formel II (22,1 g) gelöst in 100 ml Tetrahydrofuran werden 80 Minuten unter Rückfluß erhitzt. Danach wird der Niederschlag abgesaugt und mit 200 ml 2 η Salzsäure ausgekocht. Der zurückbleibende Niederschlag wird abgesaugt, mit Wasser neutral gewaschen und getrocknet. Man erhält so 19,4 g (69 % der Theorie) kristallines Pulver vom Schmelzpunkt (nach Umkristallisieren aus Äthanol) 240 bis 243°C (Zers.).b) 0.1 mol of 2-amino-5-chlorobenzoic acid of the formula III (17.2 g) and 0.1 mole (4-fluoro) phenyl 5-methylisoxazole-4-carboxylate of formula II (22.1 g) dissolved in 100 ml of tetrahydrofuran are refluxed for 80 minutes. After that, the Sucked off precipitate and boiled with 200 ml of 2 η hydrochloric acid. The remaining precipitate is filtered off with suction Washed with water until neutral and dried. 19.4 g (69% of theory) of crystalline powder with a melting point are obtained in this way (after recrystallization from ethanol) 240 to 243 ° C (decomp.).
c) 0,1 Mol 2-Amino-5-chlorbenzoesäure der Formel III (17,2 g) und 0,1 Mol (Methoxycarbonyl)-5-Methylisoxazol-4-carboxylat der Formel II (18,5 g) gelöst in 150 ml Tetrahydrofuran wird 70 Minuten unter Rückfluß erhitzt. Anschließend wird der ausgefallene Niederschlag abgesaugt und mit 200 ml 2 η Salzsäure ausgekocht. Der zurückbleibende Niederschlag wird abgesaugt, mit Wasser neutral gewaschen und getrocknet. Man erhält so 20,2 g (72 % der Theorie) eines kristallinen Pulveis vom Schmelzpunkt (nach Umkristallisieren aus Äthanol) 240 bis 243°C (Zers.).c) 0.1 mol of 2-amino-5-chlorobenzoic acid of the formula III (17.2 g) and 0.1 mol (methoxycarbonyl) -5-methylisoxazole-4-carboxylate of formula II (18.5 g) is dissolved in 150 ml of tetrahydrofuran Heated under reflux for 70 minutes. The precipitate which has separated out is then filtered off with suction and treated with 200 ml of 2η hydrochloric acid boiled out. The remaining precipitate is filtered off with suction, washed neutral with water and dried. Man thus receives 20.2 g (72% of theory) of a crystalline powder with a melting point (after recrystallization from ethanol) 240 to 243 ° C (dec.).
809824/0044 /6·809824/0044 / 6
Nach den vorstehend angegebenen Verfahren wurden die in Tabelle aufgeführten Verbindungen hergestellt.Following the procedures given above, those in Table listed compounds.
Tabelle 1: 5-Methylisoxazol-4-carbonsäureanilide der Formel ITable 1: 5-methylisoxazole-4-carboxylic acid anilides of the formula I.
Nr. R1 R2 R3 Schmelzpunkt 0CNo. R 1 R 2 R 3 melting point 0 C
1 H H 4-OH 160-1631 H H 4-OH 160-163
2 H H 4-COOH 128 - 1302 H H 4-COOH 128-130
3 H 3-OH 4-COOH 228 - 2313 H 3 -OH 4-COOH 228-231
4 H 3-COOH H 242 - 2454 H 3-COOH H 242-245
5 H 2-COOH H 208 - 2115 H 2-COOH H 208-211
6 H 2-OH 5-COOH 231 - 234 (Zers.)6 H 2-OH 5-COOH 231-234 (dec.)
7 H 2-OH 3-COOH 198 - 201 (Zers.)7 H 2-OH 3-COOH 198 - 201 (decomp.)
8 H 3-COOH 4-OH 247-251 (Zers.)8 H 3-COOH 4-OH 247-251 (dec.)
9 H 2-COOH 4-OH 228 - 231 (Zers.)9 H 2-COOH 4-OH 228-231 (decomp.)
H 2-COOH 4-Cl 240 - 243 (Zers.)H 2-COOH 4-Cl 240-243 (dec.)
H 2-OH 4-Cl 186-188H 2-OH 4-Cl 186-188
H 2-COOH 5-Br >300 (Zers.)H 2-COOH 5-Br> 300 (decomp.)
H 2-OH 5-Cl 84 - 86H 2-OH 5-Cl 84-86
1. S-Methylisoxazol^-carbonsäure- (4-hydroxy) -anilid1. S-methylisoxazole ^ -carboxylic acid (4-hydroxy) anilide
2. 5-Methylisoxazol-4-carbonsäure-(4-carboxy)-anilid2. 5-methylisoxazole-4-carboxylic acid (4-carboxy) anilide
3. 5-Methylisoxazol-4-carbonsäure-(4-carboxy-3-hydroxy)-anilid3. 5-methylisoxazole-4-carboxylic acid (4-carboxy-3-hydroxy) anilide
4. 5-Methylisoxazol-4-carbonsäure- (3-carboxy)-anilid4. 5-methylisoxazole-4-carboxylic acid (3-carboxy) anilide
5. 5-Methylisoxazol-4-carbonsäure-(2-carboxy)-anilid5. 5-methylisoxazole-4-carboxylic acid (2-carboxy) anilide
6. S-Methylisoxazol-4-carbonsäure-(5-carboxy-2-hydroxy)-anilid6. S-methylisoxazole-4-carboxylic acid (5-carboxy-2-hydroxy) anilide
7. S-Methylisoxazol^-carbonsäure-(3-carboxy-2-hydroxy)-anilid7. S-methylisoxazole ^ carboxylic acid (3-carboxy-2-hydroxy) anilide
8. S-Methylisoxazol^-carbonsäure- (3-carboxy-4-hydroxy) -anilid8. S-methylisoxazole ^ carboxylic acid (3-carboxy-4-hydroxy) anilide
9. S-Methylisoxazol^-carbonsäure- (2-carboxy-4-hydroxy) -anilid9. S-methylisoxazole ^ -carboxylic acid (2-carboxy-4-hydroxy) anilide
10. S-Methylisoxazol^-carbonsäure- (2-carboxy-4-chlor) -anilid10. S-methylisoxazole ^ carboxylic acid (2-carboxy-4-chloro) anilide
11. 5-Methylisoxazol-4-carbonsäure-(4-chlor-2-hydroxy)-anilid11. 5-Methylisoxazole-4-carboxylic acid (4-chloro-2-hydroxy) anilide
12. 5-Methylisoxazol-4-carbonsäure-(5-Brom-2-carboxy)-anilid12. 5-Methylisoxazole-4-carboxylic acid (5-bromo-2-carboxy) anilide
13. 5-Methylisoxazol-4-carbonsäure-(5-chlor-2-hydroxy)-anilid13. 5-Methylisoxazole-4-carboxylic acid (5-chloro-2-hydroxy) anilide
809824/0044809824/0044
Claims (6)
bedeuten, worin R und R weiterhin Wasserstoff bedeuten, in welchem Fall jedoch RJ nicht Methyl sein kann, in welchem Fall jedoch R zusätzlich Phenyl, das gegebenenfalls jeweils einfach öder zweifach durch Fluor7 Chlor, Brom, Jod, Alkyl mit 1,2 oder 3 C-Atomen oder Alkoxy mit Τ, 2 oder 3 C-Atomen substituiert sein kann, oder Phenoxy, das gegebenenfalls jeweils einfach oder zweifach durch Fluor, Chlor, Brom, Jod, Alkyl mit 1, 2 oder 3 C-Atomen oder Alkoxy mit 1, 2 oder 3 C-Atomen substituiert sein kann, bedeutet, oder worin R12th
mean, in which R and R still mean hydrogen, in which case, however, R J cannot be methyl, in which case, however, R additionally phenyl, which is optionally in each case once or twice by fluorine 7 chlorine, bromine, iodine, alkyl with 1,2 or 3 carbon atoms or alkoxy can be substituted with Τ, 2 or 3 carbon atoms, or phenoxy, which can optionally be substituted once or twice by fluorine, chlorine, bromine, iodine, alkyl with 1, 2 or 3 carbon atoms or alkoxy with 1, 2 or 3 carbon atoms can be substituted, or in which R
zwei oder drei der Reste R bis R neben der oben angegebenen Bedeutung für die übrigen Gruppen eine Carboxyl-Hydroxylgruppe darstellen.13th
two or three of the radicals R to R represent a carboxyl-hydroxyl group in addition to the meaning given above for the other groups.
Priority Applications (14)
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 |
CH1393377A CH614945A5 (en) | 1976-12-04 | 1977-11-15 | Process for the preparation of novel 5-methyl-isoxazole-4-carboxylic acid anilides |
ES464553A ES464553A2 (en) | 1976-12-04 | 1977-11-29 | 5-methyliso-oxazole-4-carboxylic acid anilides having pharmaceutical activity |
NL7713148A NL7713148A (en) | 1976-12-04 | 1977-11-29 | ISOXAZOLE DERIVATIVES, THEIR PREPARATION AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS. |
IT3035177A IT1113801B (en) | 1976-12-04 | 1977-12-02 | ISOSSAZOLIC DERIVATIVES, PROCESS FOR THEIR PREPARATION AND MEANS CONTAINING SUCH COMPOUNDS |
LU78626A LU78626A1 (en) | 1976-12-04 | 1977-12-02 | |
DK538577A DK538577A (en) | 1976-12-04 | 1977-12-02 | ISOXAIL DERIVATIVES PROCEDURE FOR THEIR PREPARATION AND MEASURES CONTAINING THESE COMPOUNDS |
CA292,276A CA1094564A (en) | 1976-12-04 | 1977-12-02 | Isoxazole derivatives and process for their manufacture |
AT0866277A AT362788B (en) | 1976-12-04 | 1977-12-02 | METHOD FOR PRODUCING NEW 5-METHYL-ISOXAZOLE-4-CARBONIC ACID ANILIDES |
IE245177A IE46102B1 (en) | 1976-12-04 | 1977-12-02 | 5-methylisoxazole-4-carboxylic acid anilides having pharmaceutical activity |
GB5034677A GB1595467A (en) | 1976-12-04 | 1977-12-02 | 5-methyliso-oxazole-4-carboxylic acid anilides having pharmaceutical activity |
JP14562177A JPS5371069A (en) | 1976-12-04 | 1977-12-03 | Isooxazole derivative and process for preparing same |
FR7736546A FR2372813A2 (en) | 1976-12-04 | 1977-12-05 | ISOXAZOLES DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATION |
BE183169A BE861502R (en) | 1976-12-04 | 1977-12-05 | NEW ISOXAZOLES DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATIONS |
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 |
---|---|
DE2655094A1 true DE2655094A1 (en) | 1978-06-15 |
Family
ID=5994722
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19762655094 Withdrawn DE2655094A1 (en) | 1976-12-04 | 1976-12-04 | ISOXAZOLE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND THE PRODUCTS CONTAINING THE SAME |
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) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0016277A1 (en) * | 1978-11-03 | 1980-10-01 | American Cyanamid Company | 2-Carbonyl-3-hydroxy-alkenonitriles, their use as anti-arthritic agents and processes for their preparation |
EP0035285A2 (en) * | 1979-08-17 | 1981-09-09 | 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 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 ES ES464553A patent/ES464553A2/en not_active Expired
- 1977-11-29 NL NL7713148A patent/NL7713148A/en not_active Application Discontinuation
- 1977-12-02 DK DK538577A patent/DK538577A/en unknown
- 1977-12-02 CA CA292,276A patent/CA1094564A/en not_active Expired
- 1977-12-02 AT AT0866277A patent/AT362788B/en not_active IP Right Cessation
- 1977-12-02 IT IT3035177A patent/IT1113801B/en active
- 1977-12-02 LU LU78626A patent/LU78626A1/xx unknown
- 1977-12-02 GB GB5034677A patent/GB1595467A/en not_active Expired
- 1977-12-02 IE IE245177A patent/IE46102B1/en unknown
- 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
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0016277A1 (en) * | 1978-11-03 | 1980-10-01 | American Cyanamid Company | 2-Carbonyl-3-hydroxy-alkenonitriles, their use as anti-arthritic agents and processes for their preparation |
EP0035285A2 (en) * | 1979-08-17 | 1981-09-09 | American Cyanamid Company | Novel isoxazole carboxylic acid phenyl esters, pharmaceutical compositions containing certain of said esters, and process for preparing said esters |
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 |
Also Published As
Publication number | Publication date |
---|---|
IE46102B1 (en) | 1983-02-23 |
NL7713148A (en) | 1978-06-06 |
GB1595467A (en) | 1981-08-12 |
FR2372813B2 (en) | 1980-06-20 |
DK538577A (en) | 1978-06-05 |
CH614945A5 (en) | 1979-12-28 |
IT1113801B (en) | 1986-01-27 |
IE46102L (en) | 1978-06-04 |
BE861502R (en) | 1978-06-05 |
ES464553A2 (en) | 1979-08-01 |
FR2372813A2 (en) | 1978-06-30 |
LU78626A1 (en) | 1978-07-11 |
ATA866277A (en) | 1980-11-15 |
JPS5371069A (en) | 1978-06-24 |
AT362788B (en) | 1981-06-10 |
CA1094564A (en) | 1981-01-27 |
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