DE2655009C2 - - Google Patents
Info
- Publication number
- DE2655009C2 DE2655009C2 DE19762655009 DE2655009A DE2655009C2 DE 2655009 C2 DE2655009 C2 DE 2655009C2 DE 19762655009 DE19762655009 DE 19762655009 DE 2655009 A DE2655009 A DE 2655009A DE 2655009 C2 DE2655009 C2 DE 2655009C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- general formula
- compounds
- methyl
- methylisoxazole
- 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 - Lifetime
Links
- -1 methoxy, ethoxy Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- RRGRQQFUASVDPO-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxamide Chemical class CC=1ON=CC=1C(N)=O RRGRQQFUASVDPO-UHFFFAOYSA-N 0.000 claims description 4
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical class CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZKAQPVQEYCFRTK-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC=1ON=CC=1C(Cl)=O ZKAQPVQEYCFRTK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ZINWLWNICFZQQO-UHFFFAOYSA-N n-(5-bromopyridin-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2N=CC(Br)=CC=2)=C1C ZINWLWNICFZQQO-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- LGVXPSMGABFXST-UHFFFAOYSA-N phenyl 5-methyl-1,2-oxazole-4-carboxylate Chemical compound C1(=CC=CC=C1)OC(=O)C=1C=NOC=1C LGVXPSMGABFXST-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZSOSULCXAHAKEN-UHFFFAOYSA-N (5-methyl-1,2-oxazole-4-carbonyl) 5-methyl-1,2-oxazole-4-carboxylate Chemical class O1N=CC(C(=O)OC(=O)C2=C(ON=C2)C)=C1C ZSOSULCXAHAKEN-UHFFFAOYSA-N 0.000 description 1
- QBPXGTUBZXXKJO-UHFFFAOYSA-N 1,2-oxazole-4-carboxamide Chemical compound NC(=O)C=1C=NOC=1 QBPXGTUBZXXKJO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- QFQKEBLRMHMHAT-UHFFFAOYSA-N 5-methyl-3-phenylmethoxycarbonyl-1,2-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=C(C)ON=C1C(=O)OCC1=CC=CC=C1 QFQKEBLRMHMHAT-UHFFFAOYSA-N 0.000 description 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 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- QHDXHVAUPGUMRX-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2N=CC(Cl)=CC=2)=C1C QHDXHVAUPGUMRX-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655009 DE2655009A1 (de) | 1976-12-04 | 1976-12-04 | Isoxazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| CH1393477A CH608498A5 (en) | 1976-12-04 | 1977-11-15 | Process for the preparation of novel 5-methylisoxazole- 4-carboxamides |
| NL7713151A NL7713151A (nl) | 1976-12-04 | 1977-11-29 | Isoxazoolderivaten, hun bereiding en geneesmid- delen met deze stoffen. |
| IT3035277A IT1126219B (it) | 1976-12-04 | 1977-12-02 | Derivati isossazolici,processo per la loro preparazione e mezzi contenenti tali composti |
| LU78628A LU78628A1 (pt) | 1976-12-04 | 1977-12-02 | |
| DK538677A DK538677A (da) | 1976-12-04 | 1977-12-02 | Isoxazolderivater fremgangsmaade til deres fremstilling og midler indeholdende disse forbindelser |
| GB5034777A GB1596383A (en) | 1976-12-04 | 1977-12-02 | Isoxazole derivatives process for their manufacture and preparations containing these compounds |
| IE245277A IE46269B1 (en) | 1976-12-04 | 1977-12-02 | Isoxazole derivatives,process for their manufacture and preparations containing these compounds |
| AT866377A AT362366B (de) | 1976-12-04 | 1977-12-02 | Verfahren zur herstellung von neuen 5-methyl- -isoxazol-4-carbonsaeureamiden sowie deren salzen |
| CA292,302A CA1102341A (en) | 1976-12-04 | 1977-12-02 | Isoxazole derivatives, process for their manufacture and agents containing these compounds |
| JP14562277A JPS5371070A (en) | 1976-12-04 | 1977-12-03 | Isooxazole derivative and process for preparing same |
| BE183170A BE861503R (fr) | 1976-12-04 | 1977-12-05 | Nouveaux derives d'isoxazoles, leur procede de preparation et leurs applications |
| FR7736547A FR2372830A2 (fr) | 1976-12-04 | 1977-12-05 | Derives d'isoxazole, leur procede de preparation et leur application en therapeutique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655009 DE2655009A1 (de) | 1976-12-04 | 1976-12-04 | Isoxazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2655009A1 DE2655009A1 (de) | 1978-06-15 |
| DE2655009C2 true DE2655009C2 (pt) | 1990-03-29 |
Family
ID=5994666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762655009 Granted DE2655009A1 (de) | 1976-12-04 | 1976-12-04 | Isoxazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5371070A (pt) |
| AT (1) | AT362366B (pt) |
| BE (1) | BE861503R (pt) |
| CA (1) | CA1102341A (pt) |
| CH (1) | CH608498A5 (pt) |
| DE (1) | DE2655009A1 (pt) |
| DK (1) | DK538677A (pt) |
| FR (1) | FR2372830A2 (pt) |
| GB (1) | GB1596383A (pt) |
| IE (1) | IE46269B1 (pt) |
| IT (1) | IT1126219B (pt) |
| LU (1) | LU78628A1 (pt) |
| NL (1) | NL7713151A (pt) |
Families Citing this family (15)
| 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 |
| DE2854438A1 (de) * | 1978-12-16 | 1980-07-03 | Hoechst Ag | Isoxazolderivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende mittel und ihre verwendung |
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| GB8619432D0 (en) * | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| GB8619433D0 (en) * | 1986-08-08 | 1986-09-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| US4935434A (en) * | 1988-01-26 | 1990-06-19 | Bristol-Myers Company | Antiarthritic isoxazole-4-carboxamides |
| IT1228288B (it) * | 1989-01-09 | 1991-06-07 | Zambon Spa | Composti ad attivita' antiserotoninica |
| US5001124A (en) * | 1990-02-02 | 1991-03-19 | Syntex (U.S.A.) Inc. | 4-isoxazolecarboxamide derivatives |
| EP0527736B1 (de) * | 1990-05-18 | 1997-04-16 | Hoechst Aktiengesellschaft | Isoxazol-4-carbonsäureamide und hydroxyalkyliden-cyanessigsäureamide, diese verbindungen enthaltende arzneimittel und deren verwendung |
| ZA913762B (en) | 1990-05-18 | 1992-01-29 | Hoechst Ag | Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides,pharmaceuticals containing these compounds and their use |
| US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| CN103772376B (zh) * | 2012-10-24 | 2017-01-11 | 中国医学科学院医药生物技术研究所 | 取代的苯并-1,3-杂唑类化合物、其制备方法及用途 |
| US20170088545A1 (en) * | 2014-05-14 | 2017-03-30 | Novartis Ag | Carboxamide inhibitors |
| US9403810B2 (en) * | 2014-05-14 | 2016-08-02 | Novartis Ag | Carboxamide derivatives |
-
1976
- 1976-12-04 DE DE19762655009 patent/DE2655009A1/de active Granted
-
1977
- 1977-11-15 CH CH1393477A patent/CH608498A5/xx not_active IP Right Cessation
- 1977-11-29 NL NL7713151A patent/NL7713151A/xx not_active Application Discontinuation
- 1977-12-02 LU LU78628A patent/LU78628A1/xx unknown
- 1977-12-02 IT IT3035277A patent/IT1126219B/it active
- 1977-12-02 CA CA292,302A patent/CA1102341A/en not_active Expired
- 1977-12-02 DK DK538677A patent/DK538677A/da unknown
- 1977-12-02 AT AT866377A patent/AT362366B/de not_active IP Right Cessation
- 1977-12-02 IE IE245277A patent/IE46269B1/en unknown
- 1977-12-02 GB GB5034777A patent/GB1596383A/en not_active Expired
- 1977-12-03 JP JP14562277A patent/JPS5371070A/ja active Pending
- 1977-12-05 BE BE183170A patent/BE861503R/xx not_active IP Right Cessation
- 1977-12-05 FR FR7736547A patent/FR2372830A2/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2372830A2 (fr) | 1978-06-30 |
| AT362366B (de) | 1981-05-11 |
| CA1102341A (en) | 1981-06-02 |
| DE2655009A1 (de) | 1978-06-15 |
| CH608498A5 (en) | 1979-01-15 |
| IE46269L (en) | 1978-06-04 |
| IE46269B1 (en) | 1983-04-20 |
| JPS5371070A (en) | 1978-06-24 |
| GB1596383A (en) | 1981-08-26 |
| DK538677A (da) | 1978-06-05 |
| LU78628A1 (pt) | 1978-07-11 |
| BE861503R (fr) | 1978-06-05 |
| FR2372830B2 (pt) | 1980-06-20 |
| ATA866377A (de) | 1980-10-15 |
| NL7713151A (nl) | 1978-06-06 |
| IT1126219B (it) | 1986-05-14 |
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