DE2613838A1 - Verfahren zum erzeugen der eckige klammer auf o-(2,6-dichloranilino)- phenyl eckige klammer zu -essigsaeure und von salzen derselben - Google Patents
Verfahren zum erzeugen der eckige klammer auf o-(2,6-dichloranilino)- phenyl eckige klammer zu -essigsaeure und von salzen derselbenInfo
- Publication number
- DE2613838A1 DE2613838A1 DE19762613838 DE2613838A DE2613838A1 DE 2613838 A1 DE2613838 A1 DE 2613838A1 DE 19762613838 DE19762613838 DE 19762613838 DE 2613838 A DE2613838 A DE 2613838A DE 2613838 A1 DE2613838 A1 DE 2613838A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- group
- compound
- iii
- viii
- 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- Withdrawn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 58
- 150000003839 salts Chemical class 0.000 title claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims description 31
- 230000007062 hydrolysis Effects 0.000 claims description 18
- 238000006460 hydrolysis reaction Methods 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006816 Chapman rearrangement reaction Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Chemical group 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 230000008707 rearrangement Effects 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 16
- -1 2,6-dichloroanilino Chemical group 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-M benzenecarboximidate Chemical compound [NH-]C(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 150000003936 benzamides Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 229960001259 diclofenac Drugs 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229940124641 pain reliever Drugs 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 1
- LMDPYYUISNUGGT-UHFFFAOYSA-N 2-(2-aminophenyl)acetonitrile Chemical compound NC1=CC=CC=C1CC#N LMDPYYUISNUGGT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WNKQJDMNLADBTQ-UHFFFAOYSA-N 2-[2-(2,6-dichloroanilino)phenyl]acetonitrile Chemical compound ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1CC#N WNKQJDMNLADBTQ-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- SJUVGLMFEFADAF-UHFFFAOYSA-N 4-methoxybenzenecarboximidoyl chloride Chemical compound COC1=CC=C(C(Cl)=N)C=C1 SJUVGLMFEFADAF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 241001562081 Ikeda Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- IAHMNSCQDXESII-UHFFFAOYSA-N benzenecarboximidoyl chloride Chemical compound ClC(=N)C1=CC=CC=C1 IAHMNSCQDXESII-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UELJXCRPLCATAK-UHFFFAOYSA-N ethyl 2-(2-aminophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1N UELJXCRPLCATAK-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VWHQBULMRSCMPF-UHFFFAOYSA-N tert-butyl benzenecarboximidate Chemical compound C(C)(C)(C)OC(C1=CC=CC=C1)=N VWHQBULMRSCMPF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50038682A JPS51113842A (en) | 1975-03-31 | 1975-03-31 | Process for preparing o-(2,6-dichloroanilino)phenyl acetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2613838A1 true DE2613838A1 (de) | 1976-10-07 |
Family
ID=12532044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762613838 Withdrawn DE2613838A1 (de) | 1975-03-31 | 1976-03-31 | Verfahren zum erzeugen der eckige klammer auf o-(2,6-dichloranilino)- phenyl eckige klammer zu -essigsaeure und von salzen derselben |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS51113842A (enExample) |
| AU (1) | AU504223B2 (enExample) |
| CA (1) | CA1050565A (enExample) |
| CH (1) | CH610877A5 (enExample) |
| DE (1) | DE2613838A1 (enExample) |
| DK (1) | DK157576A (enExample) |
| FI (1) | FI760842A7 (enExample) |
| FR (1) | FR2306196A1 (enExample) |
| GB (1) | GB1532087A (enExample) |
| GR (1) | GR59322B (enExample) |
| NL (1) | NL7603348A (enExample) |
| NO (1) | NO144667C (enExample) |
| SE (1) | SE413314B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3226687A1 (de) | 1981-07-23 | 1983-02-10 | Eisai Co., Ltd., Tokyo | Polyprenylverbindungen, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
| US4978773A (en) * | 1989-01-27 | 1990-12-18 | Heumann Pharma Gmbh & Co. | Process for the preparation of 2,6-dichlorodiphenylaminoacetic acid derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108947861A (zh) * | 2018-08-17 | 2018-12-07 | 复旦大学 | 双氯芬酸钠的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1053269A (enExample) * | 1964-11-27 |
-
1975
- 1975-03-31 JP JP50038682A patent/JPS51113842A/ja active Granted
-
1976
- 1976-03-25 AU AU12370/76A patent/AU504223B2/en not_active Expired
- 1976-03-26 GR GR50400A patent/GR59322B/el unknown
- 1976-03-26 GB GB12175/76A patent/GB1532087A/en not_active Expired
- 1976-03-26 CH CH379076A patent/CH610877A5/xx not_active IP Right Cessation
- 1976-03-30 CA CA249,128A patent/CA1050565A/en not_active Expired
- 1976-03-30 SE SE7603779A patent/SE413314B/xx unknown
- 1976-03-30 NO NO761097A patent/NO144667C/no unknown
- 1976-03-30 FI FI760842A patent/FI760842A7/fi not_active Application Discontinuation
- 1976-03-31 NL NL7603348A patent/NL7603348A/xx not_active Application Discontinuation
- 1976-03-31 FR FR7609273A patent/FR2306196A1/fr active Granted
- 1976-03-31 DE DE19762613838 patent/DE2613838A1/de not_active Withdrawn
- 1976-03-31 DK DK157576A patent/DK157576A/da not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3226687A1 (de) | 1981-07-23 | 1983-02-10 | Eisai Co., Ltd., Tokyo | Polyprenylverbindungen, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
| US4978773A (en) * | 1989-01-27 | 1990-12-18 | Heumann Pharma Gmbh & Co. | Process for the preparation of 2,6-dichlorodiphenylaminoacetic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| NO144667B (no) | 1981-07-06 |
| NL7603348A (nl) | 1976-10-04 |
| GR59322B (en) | 1977-12-13 |
| FR2306196B1 (enExample) | 1979-06-29 |
| DK157576A (da) | 1976-10-01 |
| GB1532087A (en) | 1978-11-15 |
| FR2306196A1 (fr) | 1976-10-29 |
| AU1237076A (en) | 1977-09-29 |
| CA1050565A (en) | 1979-03-13 |
| FI760842A7 (enExample) | 1976-10-01 |
| AU504223B2 (en) | 1979-10-04 |
| JPS565218B2 (enExample) | 1981-02-04 |
| NO761097L (enExample) | 1976-10-01 |
| NO144667C (no) | 1981-10-14 |
| JPS51113842A (en) | 1976-10-07 |
| SE413314B (sv) | 1980-05-19 |
| SE7603779L (sv) | 1976-10-01 |
| CH610877A5 (en) | 1979-05-15 |
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