DD149507A5 - Verfahren zur herstellung von 2-(3-phenoxy-phenyl)-propionsaeure - Google Patents
Verfahren zur herstellung von 2-(3-phenoxy-phenyl)-propionsaeure Download PDFInfo
- Publication number
- DD149507A5 DD149507A5 DD79218215A DD21821579A DD149507A5 DD 149507 A5 DD149507 A5 DD 149507A5 DD 79218215 A DD79218215 A DD 79218215A DD 21821579 A DD21821579 A DD 21821579A DD 149507 A5 DD149507 A5 DD 149507A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- phenoxy
- phenyl
- solution
- propionic acid
- cyano
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000002253 acid Substances 0.000 title claims description 6
- -1 2- (3-PHENOXY-PHENYL) PROPIONE Chemical compound 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- RDJGLLICXDHJDY-UHFFFAOYSA-N fenoprofen Chemical compound OC(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 230000003356 anti-rheumatic effect Effects 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000003756 stirring Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- DKGMALJGFUHPGB-UHFFFAOYSA-N 2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CCC1=CC=CC(OC=2C=CC=CC=2)=C1 DKGMALJGFUHPGB-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- SPRFQFFNDBIQDY-UHFFFAOYSA-N 2-cyano-2-(3-phenoxyphenyl)propanamide Chemical compound N#CC(C)(C(N)=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 SPRFQFFNDBIQDY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- RFALKMQNBPHELA-UHFFFAOYSA-N ethyl 2-cyano-2-(3-phenoxyphenyl)propanoate Chemical compound CCOC(=O)C(C)(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 RFALKMQNBPHELA-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000012022 methylating agents Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- AVCXUPSTLHKNGB-UHFFFAOYSA-N 2-cyano-2-(3-phenoxyphenyl)acetic acid Chemical compound OC(=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 AVCXUPSTLHKNGB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 2
- QUYVTGFWFHQVRO-UHFFFAOYSA-N 1-(chloromethyl)-3-phenoxybenzene Chemical compound ClCC1=CC=CC(OC=2C=CC=CC=2)=C1 QUYVTGFWFHQVRO-UHFFFAOYSA-N 0.000 description 2
- MJNPYEBRZXFOBP-UHFFFAOYSA-N CCC(C#N)(C1=CC(=CC=C1)OC2=CC=CC=C2)C(=O)O Chemical compound CCC(C#N)(C1=CC(=CC=C1)OC2=CC=CC=C2)C(=O)O MJNPYEBRZXFOBP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- XUDXNGUORATCNY-UHFFFAOYSA-N methyl 2-cyano-2-(3-phenoxyphenyl)propanoate Chemical compound COC(=O)C(C)(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XUDXNGUORATCNY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
- CJOMHFSNAMKXCS-UHFFFAOYSA-N 1-(2-methylprop-1-enyl)-3-phenoxybenzene Chemical compound CC(C)=CC1=CC=CC(OC=2C=CC=CC=2)=C1 CJOMHFSNAMKXCS-UHFFFAOYSA-N 0.000 description 1
- FZCDBGYCFVKRDV-UHFFFAOYSA-N 1-(3-phenoxyphenyl)ethanone Chemical class CC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FZCDBGYCFVKRDV-UHFFFAOYSA-N 0.000 description 1
- OBTDVRGUJLGMIN-UHFFFAOYSA-N 1-phenoxy-3-prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC(OC=2C=CC=CC=2)=C1 OBTDVRGUJLGMIN-UHFFFAOYSA-N 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IMPIIVKYTNMBCD-UHFFFAOYSA-N 2-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OC1=CC=CC=C1 IMPIIVKYTNMBCD-UHFFFAOYSA-N 0.000 description 1
- ZASYXXGNNSUIBS-UHFFFAOYSA-N CC(=O)C.[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])NN Chemical compound CC(=O)C.[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])NN ZASYXXGNNSUIBS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000000233 Melia azedarach Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- LKPVHTAWGPBJMM-UHFFFAOYSA-M [O-]C1=CC=CC=C1.[Mg+]C1=CC=CC=C1 Chemical compound [O-]C1=CC=CC=C1.[Mg+]C1=CC=CC=C1 LKPVHTAWGPBJMM-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- VGLCBSOALKYKJU-UHFFFAOYSA-N ethyl 2-cyano-2-(3-phenoxyphenyl)acetate Chemical compound CCOC(=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 VGLCBSOALKYKJU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229960001419 fenoprofen Drugs 0.000 description 1
- VHUXSAWXWSTUOD-UHFFFAOYSA-L fenoprofen calcium (anhydrous) Chemical compound [Ca+2].[O-]C(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1.[O-]C(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 VHUXSAWXWSTUOD-UHFFFAOYSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- CUGDBFARXMYFIW-UHFFFAOYSA-N methyl 2-cyano-2-(3-phenoxyphenyl)acetate Chemical compound COC(=O)C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 CUGDBFARXMYFIW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- FYWSTUCDSVYLPV-UHFFFAOYSA-N nitrooxythallium Chemical compound [Tl+].[O-][N+]([O-])=O FYWSTUCDSVYLPV-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001894 | 1978-12-29 | ||
| HUCI001979 HU181672B (hu) | 1979-10-25 | 1979-10-25 | Eljárás 2-(3-fenoxi-fenil)-propionsav és sói új intermedieren keresztül történő előállítására |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD149507A5 true DD149507A5 (de) | 1981-07-15 |
Family
ID=26318424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79218215A DD149507A5 (de) | 1978-12-29 | 1979-12-28 | Verfahren zur herstellung von 2-(3-phenoxy-phenyl)-propionsaeure |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US4304930A (en, 2012) |
| CH (1) | CH646944A5 (en, 2012) |
| DD (1) | DD149507A5 (en, 2012) |
| DE (1) | DE2950608A1 (en, 2012) |
| FR (1) | FR2445314A1 (en, 2012) |
| GB (1) | GB2039479B (en, 2012) |
| RO (1) | RO79023A (en, 2012) |
| SU (1) | SU1039439A3 (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8318889D0 (en) * | 1983-07-13 | 1983-08-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| US4760089A (en) * | 1985-09-09 | 1988-07-26 | Smithkline Beckman Corporation | Irreversible dopamine-β-hydroxylase inhibitors |
| EP0512352B1 (en) * | 1991-05-09 | 1996-03-27 | F. Hoffmann-La Roche Ag | Substituted carboxylic acid derivatives |
| RU2059603C1 (ru) * | 1991-05-09 | 1996-05-10 | Хоффманн-Ля Рош АГ | ПРОИЗВОДНЫЕ α -ЗАМЕЩЕННЫХ АРИЛУКСУСНЫХ КИСЛОТ И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ |
| CZ300397B6 (cs) * | 1998-09-26 | 2009-05-13 | Sanofi - Aventis Deutschland GmbH | Zpusob beztlaké výroby alfa,alfa-dimethylfenyloctové kyseliny z alfa,alfa-dimethylbenzylkyanidu |
| RU2451669C1 (ru) * | 2011-02-14 | 2012-05-27 | Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ) | Способ получения 3-феноксифенилацетонитрила |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853905A (en) * | 1968-08-15 | 1974-12-10 | Lilly Co Eli | Certain 5-(phenoxyphenalkyl) tetrazoles |
| SE363818B (en, 2012) * | 1968-08-15 | 1974-02-04 | Lilly Co Eli | |
| ES431425A1 (es) * | 1973-10-29 | 1977-01-16 | Eisai Co Ltd | Un procedimiento para la preparacion de derivados del acido 2-(m-fenoxifenil)-propionico. |
| JPS582934B2 (ja) * | 1974-07-29 | 1983-01-19 | ニツシンセイフン カブシキガイシヤ | ２−（置換アリ−ル）−プロピオン酸の製法 |
| JPS5312835A (en) * | 1976-07-22 | 1978-02-04 | Grelan Pharmaceut Co Ltd | Preparation of 2-(3-phenoxyphenyl) propionic acid |
| HU180811B (en) * | 1976-11-23 | 1983-04-29 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing phenyl-alkyl-carboxylic acids |
-
1979
- 1979-12-15 DE DE19792950608 patent/DE2950608A1/de active Granted
- 1979-12-20 GB GB7943954A patent/GB2039479B/en not_active Expired
- 1979-12-21 US US06/105,988 patent/US4304930A/en not_active Expired - Lifetime
- 1979-12-27 FR FR7931784A patent/FR2445314A1/fr active Granted
- 1979-12-28 CH CH1151279A patent/CH646944A5/de not_active IP Right Cessation
- 1979-12-28 RO RO7999753A patent/RO79023A/ro unknown
- 1979-12-28 SU SU792860205A patent/SU1039439A3/ru active
- 1979-12-28 DD DD79218215A patent/DD149507A5/de not_active IP Right Cessation
-
1981
- 1981-08-12 US US06/292,194 patent/US4393008A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SU1039439A3 (ru) | 1983-08-30 |
| DE2950608A1 (de) | 1980-07-10 |
| RO79023A (ro) | 1982-12-06 |
| FR2445314B1 (en, 2012) | 1984-09-07 |
| GB2039479B (en) | 1982-11-24 |
| DE2950608C2 (en, 2012) | 1990-09-13 |
| GB2039479A (en) | 1980-08-13 |
| FR2445314A1 (fr) | 1980-07-25 |
| CH646944A5 (de) | 1984-12-28 |
| US4304930A (en) | 1981-12-08 |
| US4393008A (en) | 1983-07-12 |
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