DE2655094A1 - Isoxazolderivate, verfahren zu ihrer herstellung und diese enthaltende mittel - Google Patents
Isoxazolderivate, verfahren zu ihrer herstellung und diese enthaltende mittelInfo
- 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- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 150000003931 anilides Chemical class 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 methylenedioxy group Chemical group 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- ZKAQPVQEYCFRTK-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC=1ON=CC=1C(Cl)=O ZKAQPVQEYCFRTK-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 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
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 150000002148 esters Chemical class 0.000 description 2
- 238000003756 stirring Methods 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SRUGNAKMXDBSDU-UHFFFAOYSA-N 2-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C(=CC=CC=2)C(O)=O)=C1C SRUGNAKMXDBSDU-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ROGQUCAEHRKRME-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C=C(C=CC=2)C(O)=O)=C1C ROGQUCAEHRKRME-UHFFFAOYSA-N 0.000 description 1
- FWQYYMSCKNQDOS-UHFFFAOYSA-N 3-methoxycarbonyl-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound COC(=O)C1=NOC(C)=C1C(O)=O FWQYYMSCKNQDOS-UHFFFAOYSA-N 0.000 description 1
- LHTADVWQJRLHFV-UHFFFAOYSA-N 4-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=C1C LHTADVWQJRLHFV-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
- 125000004429 atom Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 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 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
- 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
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 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
- 239000007858 starting material Substances 0.000 description 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)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655094 DE2655094A1 (de) | 1976-12-04 | 1976-12-04 | Isoxazolderivate, verfahren zu ihrer herstellung und diese enthaltende mittel |
| CH1393377A CH614945A5 (en) | 1976-12-04 | 1977-11-15 | Process for the preparation of novel 5-methyl-isoxazole-4-carboxylic acid anilides |
| ES464553A ES464553A2 (es) | 1976-12-04 | 1977-11-29 | Mejoras introducidas en el objeto de la patente principal por procedimiento para la preparacion de anilidas de acido 5-metil-isoxazol-4-carboxilico. |
| NL7713148A NL7713148A (nl) | 1976-12-04 | 1977-11-29 | Isoxazoolderivaten, hun bereiding en deze ver- bindingen bevattende geneesmiddelen. |
| AT0866277A AT362788B (de) | 1976-12-04 | 1977-12-02 | Verfahren zur herstellung von neuen 5-methyl-isoxazol-4-carbonsaeureaniliden |
| IE245177A IE46102B1 (en) | 1976-12-04 | 1977-12-02 | 5-methylisoxazole-4-carboxylic acid anilides having pharmaceutical activity |
| IT3035177A IT1113801B (it) | 1976-12-04 | 1977-12-02 | Derivati isossazolici,processo per la loro preparazione e mezzi contenenti tali composti |
| GB5034677A GB1595467A (en) | 1976-12-04 | 1977-12-02 | 5-methyliso-oxazole-4-carboxylic acid anilides having pharmaceutical activity |
| CA292,276A CA1094564A (en) | 1976-12-04 | 1977-12-02 | Isoxazole derivatives and process for their manufacture |
| LU78626A LU78626A1 (enExample) | 1976-12-04 | 1977-12-02 | |
| DK538577A DK538577A (da) | 1976-12-04 | 1977-12-02 | Isoxaolderivater fremgangsmaade til deres fremstilling og midler indeholdende disse forbindelser |
| JP14562177A JPS5371069A (en) | 1976-12-04 | 1977-12-03 | Isooxazole derivative and process for preparing same |
| FR7736546A FR2372813A2 (fr) | 1976-12-04 | 1977-12-05 | Derives d'isoxazoles, leur procede de preparation et leur application en therapeutique |
| BE183169A BE861502R (fr) | 1976-12-04 | 1977-12-05 | Nouveaux derives d'isoxazoles, leur procde de preparation et leurs applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655094 DE2655094A1 (de) | 1976-12-04 | 1976-12-04 | Isoxazolderivate, verfahren zu ihrer herstellung und diese enthaltende mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2655094A1 true DE2655094A1 (de) | 1978-06-15 |
Family
ID=5994722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762655094 Withdrawn DE2655094A1 (de) | 1976-12-04 | 1976-12-04 | Isoxazolderivate, verfahren zu ihrer herstellung und diese enthaltende mittel |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5371069A (enExample) |
| AT (1) | AT362788B (enExample) |
| BE (1) | BE861502R (enExample) |
| CA (1) | CA1094564A (enExample) |
| CH (1) | CH614945A5 (enExample) |
| DE (1) | DE2655094A1 (enExample) |
| DK (1) | DK538577A (enExample) |
| ES (1) | ES464553A2 (enExample) |
| FR (1) | FR2372813A2 (enExample) |
| GB (1) | GB1595467A (enExample) |
| IE (1) | IE46102B1 (enExample) |
| IT (1) | IT1113801B (enExample) |
| LU (1) | LU78626A1 (enExample) |
| NL (1) | NL7713148A (enExample) |
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 |
| 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 (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 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2538806B1 (fr) * | 1982-12-30 | 1986-02-21 | Bago Sa Labor | Composes phenyl-3 methyl isoxazole-5 carboxy-4 anilides substitues, actifs therapeutiquement contre l'inflammation et la douleur |
| 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/de not_active Withdrawn
-
1977
- 1977-11-15 CH CH1393377A patent/CH614945A5/xx not_active IP Right Cessation
- 1977-11-29 ES ES464553A patent/ES464553A2/es not_active Expired
- 1977-11-29 NL NL7713148A patent/NL7713148A/xx not_active Application Discontinuation
- 1977-12-02 CA CA292,276A patent/CA1094564A/en not_active Expired
- 1977-12-02 IT IT3035177A patent/IT1113801B/it active
- 1977-12-02 DK DK538577A patent/DK538577A/da unknown
- 1977-12-02 IE IE245177A patent/IE46102B1/en unknown
- 1977-12-02 GB GB5034677A patent/GB1595467A/en not_active Expired
- 1977-12-02 AT AT0866277A patent/AT362788B/de not_active IP Right Cessation
- 1977-12-02 LU LU78626A patent/LU78626A1/xx unknown
- 1977-12-03 JP JP14562177A patent/JPS5371069A/ja active Pending
- 1977-12-05 BE BE183169A patent/BE861502R/xx not_active IP Right Cessation
- 1977-12-05 FR FR7736546A patent/FR2372813A2/fr active Granted
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 |
| 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 (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 |
Also Published As
| Publication number | Publication date |
|---|---|
| LU78626A1 (enExample) | 1978-07-11 |
| NL7713148A (nl) | 1978-06-06 |
| IE46102B1 (en) | 1983-02-23 |
| ES464553A2 (es) | 1979-08-01 |
| JPS5371069A (en) | 1978-06-24 |
| GB1595467A (en) | 1981-08-12 |
| IE46102L (en) | 1978-06-04 |
| FR2372813B2 (enExample) | 1980-06-20 |
| AT362788B (de) | 1981-06-10 |
| DK538577A (da) | 1978-06-05 |
| CH614945A5 (en) | 1979-12-28 |
| FR2372813A2 (fr) | 1978-06-30 |
| IT1113801B (it) | 1986-01-27 |
| BE861502R (fr) | 1978-06-05 |
| ATA866277A (de) | 1980-11-15 |
| CA1094564A (en) | 1981-01-27 |
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