DE2342118C2 - Phenoxypropionsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen - Google Patents
Phenoxypropionsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische ZubereitungenInfo
- Publication number
- DE2342118C2 DE2342118C2 DE2342118A DE2342118A DE2342118C2 DE 2342118 C2 DE2342118 C2 DE 2342118C2 DE 2342118 A DE2342118 A DE 2342118A DE 2342118 A DE2342118 A DE 2342118A DE 2342118 C2 DE2342118 C2 DE 2342118C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- general formula
- methyl
- compounds
- propionic 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.)
- Expired
Links
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical class OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title description 31
- 238000000034 method Methods 0.000 title description 19
- 238000002360 preparation method Methods 0.000 title description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000002253 acid Substances 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 26
- -1 1-methyl-4-piperidyl Chemical group 0.000 description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 14
- 238000009835 boiling Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- FMSWJUQSKXAMEN-UHFFFAOYSA-N 2-[4-[(4-chlorophenoxy)methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1COC1=CC=C(Cl)C=C1 FMSWJUQSKXAMEN-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- PSBWSIWOVNCTKX-UHFFFAOYSA-N 4-(phenoxymethyl)phenol Chemical compound C1=CC(O)=CC=C1COC1=CC=CC=C1 PSBWSIWOVNCTKX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000009435 amidation Effects 0.000 description 4
- 238000007112 amidation reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- ZMSZXQCQZOAYTB-UHFFFAOYSA-N 2-methyl-2-[4-(phenoxymethyl)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1COC1=CC=CC=C1 ZMSZXQCQZOAYTB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000002862 amidating effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000003797 solvolysis reaction Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- MQZNTHRONACGPJ-UHFFFAOYSA-N 2-[4-[(4-bromophenoxy)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1COC1=CC=C(Br)C=C1 MQZNTHRONACGPJ-UHFFFAOYSA-N 0.000 description 2
- WLJCFLBXCJYQGN-UHFFFAOYSA-N 2-[4-[(4-fluorophenoxy)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1COC1=CC=C(F)C=C1 WLJCFLBXCJYQGN-UHFFFAOYSA-N 0.000 description 2
- XYCOXTANZAIUGW-UHFFFAOYSA-N 2-[4-[(4-fluorophenoxy)methyl]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1COC1=CC=C(F)C=C1 XYCOXTANZAIUGW-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
- 229960001214 clofibrate Drugs 0.000 description 2
- 229920001577 copolymer Chemical group 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- VGSHXXMVULEGKD-UHFFFAOYSA-N ethyl 2-[4-[(4-fluorophenoxy)methyl]phenoxy]-2-methylpropanoate Chemical compound C(C)OC(C(C)(C)OC1=CC=C(C=C1)COC1=CC=C(C=C1)F)=O VGSHXXMVULEGKD-UHFFFAOYSA-N 0.000 description 2
- STPHCUMYWCENNR-UHFFFAOYSA-N ethyl 2-methyl-2-[4-(phenoxymethyl)phenoxy]propanoate Chemical compound C(C)OC(C(C)(C)OC1=CC=C(C=C1)COC1=CC=CC=C1)=O STPHCUMYWCENNR-UHFFFAOYSA-N 0.000 description 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000001149 thermolysis Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- JPQPNPZCVFNCOV-UHFFFAOYSA-N 2-[4-[(4-chlorophenoxy)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1COC1=CC=C(Cl)C=C1 JPQPNPZCVFNCOV-UHFFFAOYSA-N 0.000 description 1
- XDSDCTDECRVDTB-UHFFFAOYSA-N 2-bromo-2-methylpropanenitrile Chemical compound CC(C)(Br)C#N XDSDCTDECRVDTB-UHFFFAOYSA-N 0.000 description 1
- XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 1
- MYCXCBCDXVFXNE-UHFFFAOYSA-N 2-chloro-2-methylpropanoic acid Chemical compound CC(C)(Cl)C(O)=O MYCXCBCDXVFXNE-UHFFFAOYSA-N 0.000 description 1
- KZLYQYPURWXOEW-UHFFFAOYSA-N 2-iodopropanoic acid Chemical compound CC(I)C(O)=O KZLYQYPURWXOEW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FUTHIHNWIWKGJQ-UHFFFAOYSA-N 4-[(4-fluorophenoxy)methyl]phenol Chemical compound C1=CC(O)=CC=C1COC1=CC=C(F)C=C1 FUTHIHNWIWKGJQ-UHFFFAOYSA-N 0.000 description 1
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- 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)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (23)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2342118A DE2342118C2 (de) | 1973-08-21 | 1973-08-21 | Phenoxypropionsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen |
ZA00744542A ZA744542B (en) | 1973-08-21 | 1974-07-16 | Phenoxypropionic acid derivatives, the preparation thereof and compositions containing them |
IL45322A IL45322A (en) | 1973-08-21 | 1974-07-22 | Phenoxymethyl-phenoxy-propionic acid derivatives the preparation thereof and compositions containing them |
US05/497,300 US3968143A (en) | 1973-08-21 | 1974-08-14 | Phenoxypropionic acid derivatives |
SE7410468A SE7410468L (en, 2012) | 1973-08-21 | 1974-08-16 | |
AU72487/74A AU481547B2 (en) | 1973-08-21 | 1974-08-19 | Phenoxypropionic acid derivatives the preparation thereof, and compositions containing them |
DK441274A DK441274A (en, 2012) | 1973-08-21 | 1974-08-19 | |
ES429360A ES429360A1 (es) | 1973-08-21 | 1974-08-19 | Procedimiento para la obtencion de derivados del acido fe- noxipropionico. |
CH1128874A CH605556A5 (en, 2012) | 1973-08-21 | 1974-08-19 | |
FR7428430A FR2241295B1 (en, 2012) | 1973-08-21 | 1974-08-19 | |
BE147722A BE818975A (fr) | 1973-08-21 | 1974-08-19 | Derives d'acides phenoxypropioniques et leur procede de preparation |
NL7411105A NL7411105A (nl) | 1973-08-21 | 1974-08-20 | Werkwijze voor het bereiden van fenoxypropion- zuurderivaten. |
GB3663974A GB1438265A (en, 2012) | 1973-08-21 | 1974-08-20 | |
CS4737A CS175398B2 (en, 2012) | 1973-08-21 | 1974-08-20 | |
CA207,418A CA1059517A (en) | 1973-08-21 | 1974-08-20 | Phenoxypropionic acid derivatives and process for their preparation |
DD180626A DD116597A5 (en, 2012) | 1973-08-21 | 1974-08-20 | |
CS4738A CS175399B2 (en, 2012) | 1973-08-21 | 1974-08-20 | |
CS5785A CS175386B2 (en, 2012) | 1973-08-21 | 1974-08-20 | |
JP49096045A JPS5049245A (en, 2012) | 1973-08-21 | 1974-08-20 | |
HUME1765A HU169108B (en, 2012) | 1973-08-21 | 1974-08-21 | |
US05/644,033 US4039683A (en) | 1973-08-21 | 1975-12-24 | Phenoxypropionic acid derivatives and pharmaceutical preparations containing same |
AT175477A AT350047B (de) | 1973-08-21 | 1977-03-15 | Verfahren zur herstellung von neuen 2-phenoxy- methyl-phenoxypropionsaeurederivaten |
AT175377A AT350046B (de) | 1973-08-21 | 1977-03-15 | Verfahren zur herstellung von neuen 2-phenoxy- methyl-phenoxypropionsaeurederivaten |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2342118A DE2342118C2 (de) | 1973-08-21 | 1973-08-21 | Phenoxypropionsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2342118A1 DE2342118A1 (de) | 1975-03-06 |
DE2342118C2 true DE2342118C2 (de) | 1982-09-23 |
Family
ID=5890277
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2342118A Expired DE2342118C2 (de) | 1973-08-21 | 1973-08-21 | Phenoxypropionsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen |
Country Status (17)
Country | Link |
---|---|
US (1) | US3968143A (en, 2012) |
JP (1) | JPS5049245A (en, 2012) |
BE (1) | BE818975A (en, 2012) |
CA (1) | CA1059517A (en, 2012) |
CH (1) | CH605556A5 (en, 2012) |
CS (3) | CS175398B2 (en, 2012) |
DD (1) | DD116597A5 (en, 2012) |
DE (1) | DE2342118C2 (en, 2012) |
DK (1) | DK441274A (en, 2012) |
ES (1) | ES429360A1 (en, 2012) |
FR (1) | FR2241295B1 (en, 2012) |
GB (1) | GB1438265A (en, 2012) |
HU (1) | HU169108B (en, 2012) |
IL (1) | IL45322A (en, 2012) |
NL (1) | NL7411105A (en, 2012) |
SE (1) | SE7410468L (en, 2012) |
ZA (1) | ZA744542B (en, 2012) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4098816A (en) * | 1973-08-23 | 1978-07-04 | Beecham Group Limited | Polycyclic oxy-aromatic acid |
US4070178A (en) * | 1975-09-03 | 1978-01-24 | Rohm And Haas Company | Herbicidal diphenyl ethers |
DE2617804C2 (de) * | 1976-04-23 | 1985-01-24 | Hoechst Ag, 6230 Frankfurt | 2-(4-Phenoxy phenoxy)-propionsäurederivate und ihre Verwendung als Herbizide |
DE2623558C2 (de) * | 1976-05-26 | 1984-12-06 | Hoechst Ag, 6230 Frankfurt | 2-[4'-Phenoxy-phenoxy]propionsäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide Mittel |
US4169720A (en) * | 1976-08-04 | 1979-10-02 | Celamerck Gmbh & Co. Kg | 2-[4-(4-Chlorophenoxymethyl)-phenoxy]-propionic acid compounds as herbicides |
DE2709032A1 (de) * | 1977-03-02 | 1978-09-07 | Hoechst Ag | Herbizide mittel |
US4163859A (en) * | 1977-07-18 | 1979-08-07 | G. D. Searle & Co. | Phenoxyldialkyl acetic acids and esters |
JPS5562043A (en) * | 1978-11-01 | 1980-05-10 | Ihara Chem Ind Co Ltd | Preparation of phenoxycarboxylic acid derivative |
USRE31624E (en) * | 1979-11-26 | 1984-07-03 | Forsyth Dental Infirmary For Children | Method of treating inflammation |
US4244956A (en) * | 1979-11-26 | 1981-01-13 | Forsyth Dental Infirmary For Children | Method of treating inflammation |
DE2949728A1 (de) * | 1979-12-11 | 1981-06-19 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von optisch aktiven 2-phenoxypropionsaeuren |
US4563526A (en) * | 1980-09-19 | 1986-01-07 | Forsyth Dental Infirmary For Children | Substituted 2-(arylmethoxy) phenol compounds for the treatment of inflammation |
DE3326164A1 (de) * | 1983-07-20 | 1985-01-31 | Klinge Pharma GmbH, 8000 München | Neue p-oxibenzoesaeure-derivate, sowie verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
US5008439A (en) * | 1988-03-21 | 1991-04-16 | Hoechst Celanese Corporation | Synthesis of 2-(4-hydroxyphenoxy) alkanoic acid esters |
US4908476A (en) * | 1988-03-21 | 1990-03-13 | Hoechst Celanese Corporation | Synthesis of 2-(4-hydroxyphenoxy)alkanoic acids |
US5013864A (en) * | 1989-12-08 | 1991-05-07 | G. D. Searle & Co. | Process for preparation of α-alkoxy acetic acids and their salts |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB860303A (en) * | 1958-06-20 | 1961-02-01 | Ici Ltd | Pharmaceutical compositions comprising ª‡-aryloxy-aliphatic carboxylic acids and/or ª |
GB1121722A (en) * | 1966-03-31 | 1968-07-31 | Ici Ltd | New carboxylic acid derivatives |
US3586709A (en) * | 1968-09-09 | 1971-06-22 | Velsicol Chemical Corp | 2-dialkylaminobenzhydryl esters of aromatic acids |
BE754245A (fr) * | 1969-08-01 | 1970-12-31 | Sumitomo Chemical Co | Derives d'acides phenoxy carboxyliques |
BE786644A (fr) * | 1971-07-23 | 1973-01-24 | Hoechst Ag | Derives d'acides phenoxy-4 phenoxy-alcane-carboxyliques leur preparation et les medicaments qui en contiennent |
JPS5829604B2 (ja) * | 1975-07-02 | 1983-06-23 | 富士写真フイルム株式会社 | キヨウジセイフンマツノセイホウ |
JPS525493A (en) * | 1975-07-03 | 1977-01-17 | Ngk Insulators Ltd | Insulator apparatus |
-
1973
- 1973-08-21 DE DE2342118A patent/DE2342118C2/de not_active Expired
-
1974
- 1974-07-16 ZA ZA00744542A patent/ZA744542B/xx unknown
- 1974-07-22 IL IL45322A patent/IL45322A/xx unknown
- 1974-08-14 US US05/497,300 patent/US3968143A/en not_active Expired - Lifetime
- 1974-08-16 SE SE7410468A patent/SE7410468L/xx unknown
- 1974-08-19 DK DK441274A patent/DK441274A/da unknown
- 1974-08-19 FR FR7428430A patent/FR2241295B1/fr not_active Expired
- 1974-08-19 ES ES429360A patent/ES429360A1/es not_active Expired
- 1974-08-19 CH CH1128874A patent/CH605556A5/xx not_active IP Right Cessation
- 1974-08-19 BE BE147722A patent/BE818975A/xx unknown
- 1974-08-20 CA CA207,418A patent/CA1059517A/en not_active Expired
- 1974-08-20 GB GB3663974A patent/GB1438265A/en not_active Expired
- 1974-08-20 DD DD180626A patent/DD116597A5/xx unknown
- 1974-08-20 JP JP49096045A patent/JPS5049245A/ja active Pending
- 1974-08-20 CS CS4737A patent/CS175398B2/cs unknown
- 1974-08-20 NL NL7411105A patent/NL7411105A/xx not_active Application Discontinuation
- 1974-08-20 CS CS5785A patent/CS175386B2/cs unknown
- 1974-08-20 CS CS4738A patent/CS175399B2/cs unknown
- 1974-08-21 HU HUME1765A patent/HU169108B/hu unknown
Also Published As
Publication number | Publication date |
---|---|
JPS5049245A (en, 2012) | 1975-05-01 |
NL7411105A (nl) | 1975-02-25 |
FR2241295A1 (en, 2012) | 1975-03-21 |
CA1059517A (en) | 1979-07-31 |
CS175399B2 (en, 2012) | 1977-05-31 |
IL45322A (en) | 1978-03-10 |
DD116597A5 (en, 2012) | 1975-12-05 |
SE7410468L (en, 2012) | 1975-02-24 |
CS175398B2 (en, 2012) | 1977-05-31 |
AU7248774A (en) | 1976-02-19 |
CS175386B2 (en, 2012) | 1977-05-31 |
IL45322A0 (en) | 1974-10-22 |
CH605556A5 (en, 2012) | 1978-09-29 |
ES429360A1 (es) | 1977-01-16 |
DK441274A (en, 2012) | 1975-04-28 |
FR2241295B1 (en, 2012) | 1978-06-30 |
US3968143A (en) | 1976-07-06 |
HU169108B (en, 2012) | 1976-09-28 |
DE2342118A1 (de) | 1975-03-06 |
GB1438265A (en, 2012) | 1976-06-03 |
ZA744542B (en) | 1975-07-30 |
BE818975A (fr) | 1975-02-19 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
OD | Request for examination | ||
D2 | Grant after examination | ||
8339 | Ceased/non-payment of the annual fee |