NO753837L - - Google Patents
Info
- Publication number
- NO753837L NO753837L NO753837A NO753837A NO753837L NO 753837 L NO753837 L NO 753837L NO 753837 A NO753837 A NO 753837A NO 753837 A NO753837 A NO 753837A NO 753837 L NO753837 L NO 753837L
- Authority
- NO
- Norway
- Prior art keywords
- radical
- trifluoro
- formula
- mixture
- chlorophenyl
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- -1 naphthyl radical Chemical class 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000007858 starting material Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 15
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000012312 sodium hydride Substances 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical group CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- WUMAGBFCMDODFV-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)phenyl]methoxy]-3,3,3-trifluoro-2-methylpropanoic acid Chemical compound C1=CC(COC(C)(C(O)=O)C(F)(F)F)=CC=C1C1=CC=C(Cl)C=C1 WUMAGBFCMDODFV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- GEAXLHPORCRESC-UHFFFAOYSA-N chlorocyclohexatriene Chemical compound ClC1=CC=C=C[CH]1 GEAXLHPORCRESC-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 186
- 239000000203 mixture Substances 0.000 description 122
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- 239000003921 oil Substances 0.000 description 46
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- 239000007787 solid Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000284 extract Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 239000012258 stirred mixture Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- OLCRCPCKHIILMR-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propanoate Chemical compound CCOC(=O)C(O)(C(F)(F)F)C(F)(F)F OLCRCPCKHIILMR-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- NFCOSRCEYMBQCJ-UHFFFAOYSA-N 1-chloro-4-[4-(chloromethyl)phenyl]benzene Chemical compound C1=CC(CCl)=CC=C1C1=CC=C(Cl)C=C1 NFCOSRCEYMBQCJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- XUQUEFHVFISFBS-UHFFFAOYSA-M [4-(4-chlorophenyl)phenyl]-thiophen-2-yliodanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(Cl)=CC=C1C(C=C1)=CC=C1[I+]C1=CC=CS1 XUQUEFHVFISFBS-UHFFFAOYSA-M 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 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 5
- RFVRAHNIMKSQDM-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)phenyl]methoxy]-3,3,3-trifluoro-2-(trifluoromethyl)propanoyl chloride Chemical compound C1=CC(COC(C(F)(F)F)(C(Cl)=O)C(F)(F)F)=CC=C1C1=CC=C(Cl)C=C1 RFVRAHNIMKSQDM-UHFFFAOYSA-N 0.000 description 5
- QBVVPOPOMCVRRO-UHFFFAOYSA-N 3,3,3-trifluoro-2-methyl-2-(naphthalen-2-ylmethoxy)propanoyl chloride Chemical compound C1=CC=CC2=CC(COC(C)(C(Cl)=O)C(F)(F)F)=CC=C21 QBVVPOPOMCVRRO-UHFFFAOYSA-N 0.000 description 5
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-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 5
- 238000010828 elution Methods 0.000 description 5
- RDURWSDJZWOIGK-UHFFFAOYSA-N ethyl 2-(4-chlorophenoxy)-3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound CCOC(=O)C(C(F)(F)F)(C(F)(F)F)OC1=CC=C(Cl)C=C1 RDURWSDJZWOIGK-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- NKNWDMQCOPTACU-UHFFFAOYSA-N 2-chloro-6-(chloromethyl)naphthalene Chemical compound C1=C(Cl)C=CC2=CC(CCl)=CC=C21 NKNWDMQCOPTACU-UHFFFAOYSA-N 0.000 description 4
- WIKMJRHPNGPQRH-UHFFFAOYSA-N 4-hydroxy-n,n-dimethylbutanamide Chemical compound CN(C)C(=O)CCCO WIKMJRHPNGPQRH-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- QXJDOYKGRZVODP-UHFFFAOYSA-M bis(4-chlorophenyl)iodanium;chloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1[I+]C1=CC=C(Cl)C=C1 QXJDOYKGRZVODP-UHFFFAOYSA-M 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 210000002381 plasma Anatomy 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- PMBIQWABFJYSGD-UHFFFAOYSA-N 2-(4-chlorophenoxy)-3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(C(F)(F)F)(C(F)(F)F)OC1=CC=C(Cl)C=C1 PMBIQWABFJYSGD-UHFFFAOYSA-N 0.000 description 3
- JYLGKVDVIPITQM-UHFFFAOYSA-N 2-(chloromethyl)-6-methoxynaphthalene Chemical compound C1=C(CCl)C=CC2=CC(OC)=CC=C21 JYLGKVDVIPITQM-UHFFFAOYSA-N 0.000 description 3
- LTAZBUJFMKBRRK-UHFFFAOYSA-N 2-[(4-chlorophenyl)methoxy]-3,3,3-trifluoro-2-(trifluoromethyl)propanenitrile Chemical compound FC(F)(F)C(C(F)(F)F)(C#N)OCC1=CC=C(Cl)C=C1 LTAZBUJFMKBRRK-UHFFFAOYSA-N 0.000 description 3
- QONJYFFRMXDFKW-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)phenoxy]-3,3,3-trifluoro-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C(O)=O)C(F)(F)F)=CC=C1C1=CC=C(Cl)C=C1 QONJYFFRMXDFKW-UHFFFAOYSA-N 0.000 description 3
- MBYRLQSEGUSDFE-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)phenyl]methoxy]-3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid Chemical compound C1=CC(COC(C(=O)O)(C(F)(F)F)C(F)(F)F)=CC=C1C1=CC=C(Cl)C=C1 MBYRLQSEGUSDFE-UHFFFAOYSA-N 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 3
- JAINPVBSPNFKCW-UHFFFAOYSA-N 3,3,3-trifluoro-2-methyl-2-(naphthalen-1-ylmethoxy)propanoic acid Chemical compound C1=CC=C2C(COC(C)(C(O)=O)C(F)(F)F)=CC=CC2=C1 JAINPVBSPNFKCW-UHFFFAOYSA-N 0.000 description 3
- REBGWCLHTRLTAT-UHFFFAOYSA-N 3,3,3-trifluoro-2-methyl-2-(naphthalen-2-ylmethoxy)propanoic acid Chemical compound C1=CC=CC2=CC(COC(C)(C(O)=O)C(F)(F)F)=CC=C21 REBGWCLHTRLTAT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000002456 anti-arthritic effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- BVJUKWNIFOMSCT-UHFFFAOYSA-N methyl 2-[4-(4-chlorophenyl)phenoxy]-3,3,3-trifluoro-2-methylpropanoate Chemical compound C1=CC(OC(C)(C(=O)OC)C(F)(F)F)=CC=C1C1=CC=C(Cl)C=C1 BVJUKWNIFOMSCT-UHFFFAOYSA-N 0.000 description 3
- SEWPIJBPLUWMPM-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-[(6-methoxynaphthalen-2-yl)methoxy]-2-methylpropanoate Chemical compound C1=C(OC)C=CC2=CC(COC(C)(C(=O)OC)C(F)(F)F)=CC=C21 SEWPIJBPLUWMPM-UHFFFAOYSA-N 0.000 description 3
- YRMRSTBBHVHZRX-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-methyl-2-(4-phenoxyphenoxy)propanoate Chemical compound C1=CC(OC(C)(C(=O)OC)C(F)(F)F)=CC=C1OC1=CC=CC=C1 YRMRSTBBHVHZRX-UHFFFAOYSA-N 0.000 description 3
- URIXEVPUSVYOGS-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-methyl-2-(naphthalen-1-ylmethoxy)propanoate Chemical compound C1=CC=C2C(COC(C)(C(=O)OC)C(F)(F)F)=CC=CC2=C1 URIXEVPUSVYOGS-UHFFFAOYSA-N 0.000 description 3
- UULUTLBHTPGULX-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-methyl-2-(naphthalen-2-ylmethoxy)propanoate Chemical compound C1=CC=CC2=CC(COC(C)(C(=O)OC)C(F)(F)F)=CC=C21 UULUTLBHTPGULX-UHFFFAOYSA-N 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- JDIYNIZGDAGPPS-UHFFFAOYSA-N sodium;3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propanenitrile Chemical compound [Na].N#CC(O)(C(F)(F)F)C(F)(F)F JDIYNIZGDAGPPS-UHFFFAOYSA-N 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 description 2
- BJGJYPRQYKBIRZ-UHFFFAOYSA-N (6-chloronaphthalen-2-yl)methanol Chemical class C1=C(Cl)C=CC2=CC(CO)=CC=C21 BJGJYPRQYKBIRZ-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
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- GRTOGORTSDXSFK-UHFFFAOYSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-UHFFFAOYSA-N 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
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- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
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- VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 description 1
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
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- PQUHDZRNUUJRJK-UHFFFAOYSA-L disodium 2-[[4-(4-chlorophenyl)phenyl]methoxy]-3,3,3-trifluoro-2-(trifluoromethyl)propanoate trihydrate Chemical compound O.O.O.[Na+].[Na+].[O-]C(=O)C(OCc1ccc(cc1)-c1ccc(Cl)cc1)(C(F)(F)F)C(F)(F)F.[O-]C(=O)C(OCc1ccc(cc1)-c1ccc(Cl)cc1)(C(F)(F)F)C(F)(F)F PQUHDZRNUUJRJK-UHFFFAOYSA-L 0.000 description 1
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- QCAZFLIEKCGFAV-UHFFFAOYSA-N ethyl 2-[[4-(4-chlorophenyl)phenyl]methoxy]-3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound C1=CC(COC(C(=O)OCC)(C(F)(F)F)C(F)(F)F)=CC=C1C1=CC=C(Cl)C=C1 QCAZFLIEKCGFAV-UHFFFAOYSA-N 0.000 description 1
- WBWCFUPGXRXSHC-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-(4-phenylphenoxy)-2-(trifluoromethyl)propanoate Chemical compound C1=CC(OC(C(=O)OCC)(C(F)(F)F)C(F)(F)F)=CC=C1C1=CC=CC=C1 WBWCFUPGXRXSHC-UHFFFAOYSA-N 0.000 description 1
- VNSXZZNRZKHFHN-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-(naphthalen-1-ylmethoxy)-2-(trifluoromethyl)propanoate Chemical compound C1=CC=C2C(COC(C(=O)OCC)(C(F)(F)F)C(F)(F)F)=CC=CC2=C1 VNSXZZNRZKHFHN-UHFFFAOYSA-N 0.000 description 1
- QSNYQNIDWMATAE-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-(naphthalen-2-ylmethoxy)-2-(trifluoromethyl)propanoate Chemical compound C1=CC=CC2=CC(COC(C(=O)OCC)(C(F)(F)F)C(F)(F)F)=CC=C21 QSNYQNIDWMATAE-UHFFFAOYSA-N 0.000 description 1
- GVENEXHISFIHGW-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-[(2-methylnaphthalen-1-yl)methoxy]-2-(trifluoromethyl)propanoate Chemical compound C1=CC=C2C(COC(C(=O)OCC)(C(F)(F)F)C(F)(F)F)=C(C)C=CC2=C1 GVENEXHISFIHGW-UHFFFAOYSA-N 0.000 description 1
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- 210000003918 fraction a Anatomy 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
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- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- MGIWTNWGIXYVOP-UHFFFAOYSA-N methyl 2-(4-chlorophenoxy)-3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound COC(=O)C(C(F)(F)F)(C(F)(F)F)OC1=CC=C(Cl)C=C1 MGIWTNWGIXYVOP-UHFFFAOYSA-N 0.000 description 1
- LLZCYERAIACRFW-UHFFFAOYSA-N methyl 2-(4-chlorophenoxy)-3,3,3-trifluoro-2-methylpropanoate Chemical compound COC(=O)C(C)(C(F)(F)F)OC1=CC=C(Cl)C=C1 LLZCYERAIACRFW-UHFFFAOYSA-N 0.000 description 1
- FXBDALXMXXZALE-UHFFFAOYSA-N methyl 2-[4-(4-chlorophenyl)phenoxy]-3,3,3-trifluoropropanoate Chemical compound ClC1=CC=C(C=C1)C1=CC=C(OC(C(=O)OC)C(F)(F)F)C=C1 FXBDALXMXXZALE-UHFFFAOYSA-N 0.000 description 1
- HCJXLECBFRSYRV-UHFFFAOYSA-N methyl 2-[[4-(4-chlorophenyl)phenyl]methoxy]-3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound C1=CC(COC(C(=O)OC)(C(F)(F)F)C(F)(F)F)=CC=C1C1=CC=C(Cl)C=C1 HCJXLECBFRSYRV-UHFFFAOYSA-N 0.000 description 1
- QFDCYSMNTCULOJ-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-phenoxy-2-(trifluoromethyl)propanoate Chemical compound COC(=O)C(C(F)(F)F)(C(F)(F)F)OC1=CC=CC=C1 QFDCYSMNTCULOJ-UHFFFAOYSA-N 0.000 description 1
- ZLVPRNFYGCBLDS-UHFFFAOYSA-N methyl 6-methoxynaphthalene-2-carboxylate Chemical compound C1=C(OC)C=CC2=CC(C(=O)OC)=CC=C21 ZLVPRNFYGCBLDS-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
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- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- JVWOCHRRAWHKLT-UHFFFAOYSA-N nicametate Chemical compound CCN(CC)CCOC(=O)C1=CC=CN=C1 JVWOCHRRAWHKLT-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- UXHKNLTTXFZMFH-UHFFFAOYSA-M phenyl(thiophen-2-yl)iodanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CS1 UXHKNLTTXFZMFH-UHFFFAOYSA-M 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
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- XKUNYCNZSWCFML-UHFFFAOYSA-N pyridin-3-ylmethyl 3,3,3-trifluoro-2-methyl-2-(naphthalen-2-ylmethoxy)propanoate Chemical compound C=1C=C2C=CC=CC2=CC=1COC(C)(C(F)(F)F)C(=O)OCC1=CC=CN=C1 XKUNYCNZSWCFML-UHFFFAOYSA-N 0.000 description 1
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- XMCPOYVTAGJODM-UHFFFAOYSA-M sodium;2-[[4-(4-chlorophenyl)phenyl]methoxy]-3,3,3-trifluoro-2-methylpropanoate Chemical compound [Na+].C1=CC(COC(C)(C([O-])=O)C(F)(F)F)=CC=C1C1=CC=C(Cl)C=C1 XMCPOYVTAGJODM-UHFFFAOYSA-M 0.000 description 1
- XRJOBTHKRUEDTQ-UHFFFAOYSA-M sodium;[4-(4-chlorophenyl)phenoxy]methanesulfonate Chemical compound [Na+].C1=CC(OCS(=O)(=O)[O-])=CC=C1C1=CC=C(Cl)C=C1 XRJOBTHKRUEDTQ-UHFFFAOYSA-M 0.000 description 1
- HKPHUICWPSKEMR-UHFFFAOYSA-M sodium;chloromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCl HKPHUICWPSKEMR-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/29—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with halogen-containing compounds which may be formed in situ
-
- 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
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/115—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing halogen
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/72—Polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Rheumatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Physical Education & Sports Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB52829/74A GB1499508A (en) | 1974-12-06 | 1974-12-06 | 3,3,3-trifluoropropionic acid derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
NO753837L true NO753837L (fi) | 1976-06-09 |
Family
ID=10465488
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO753837A NO753837L (fi) | 1974-12-06 | 1975-11-14 |
Country Status (25)
Country | Link |
---|---|
US (1) | US4055595A (fi) |
JP (1) | JPS51125227A (fi) |
AR (1) | AR213278A1 (fi) |
AT (1) | AT347432B (fi) |
BE (1) | BE836353A (fi) |
CA (1) | CA1064498A (fi) |
CH (1) | CH618414A5 (fi) |
CS (1) | CS191948B2 (fi) |
DD (1) | DD122963A5 (fi) |
DE (1) | DE2554882A1 (fi) |
DK (1) | DK546575A (fi) |
ES (3) | ES443237A1 (fi) |
FI (1) | FI753393A (fi) |
FR (1) | FR2293196A1 (fi) |
GB (1) | GB1499508A (fi) |
HU (1) | HU170016B (fi) |
IE (1) | IE42454B1 (fi) |
IL (1) | IL48477A (fi) |
LU (1) | LU73936A1 (fi) |
NL (1) | NL7514070A (fi) |
NO (1) | NO753837L (fi) |
PL (3) | PL102241B1 (fi) |
SE (1) | SE7513676L (fi) |
SU (1) | SU764608A3 (fi) |
ZA (1) | ZA757089B (fi) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2843776A1 (de) * | 1977-10-07 | 1979-04-12 | Science Union & Cie | (arylalkyl)-alkansaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
FR2460286A1 (fr) * | 1979-06-29 | 1981-01-23 | Rhone Poulenc Agrochimie | Procede de preparation d'acide phenoxy-2 propioniques optiquement actifs |
CA1160245A (en) * | 1979-07-26 | 1984-01-10 | Paul E. Aldrich | Antihypertensive polyhalohydroxyisopropyl phenylalkanoic and phenylalkenoic acids, amides and esters and intermediates thereto |
DE3028627A1 (de) * | 1980-07-29 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | 2-fluoralkancarbonsaeureverbindungen, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung |
DE4327365A1 (de) * | 1993-08-14 | 1995-02-16 | Boehringer Mannheim Gmbh | Verwendung von Phenolen und Phenolderivaten als Arzneimittel mit fibrinogensenkender Wirkung |
US6664022B1 (en) * | 2000-08-25 | 2003-12-16 | Shipley Company, L.L.C. | Photoacid generators and photoresists comprising same |
GB0808986D0 (en) | 2008-05-16 | 2008-06-25 | Univ Newcastle | Formation of 18F and 19F fluoroarenes bearing reactive functionalities |
US7935269B2 (en) * | 2009-05-19 | 2011-05-03 | North American Salt Company | Deicing blend and method of using the same |
CN115067318B (zh) * | 2022-02-22 | 2023-07-14 | 深圳中检联新药检测有限责任公司 | 一种牙髓间充质干细胞保存液及其应用 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3379752A (en) * | 1964-05-20 | 1968-04-23 | Merck & Co Inc | Phenoxy substituted 3-hydroxyalkanoic acids and a method for their preparation |
US3347910A (en) * | 1964-12-10 | 1967-10-17 | Merck & Co Inc | Cycloaliphatic substituted naphthyloxy-alkanoic acids and a method for their preparation |
GB1140748A (en) * | 1966-06-23 | 1969-01-22 | Ici Ltd | New carboxylic acid derivatives |
US3721703A (en) * | 1968-01-11 | 1973-03-20 | Hoechst Ag | Phenoxyalkane-carboxylic acids,salts and esters thereof |
US3642869A (en) * | 1969-07-30 | 1972-02-15 | Squibb & Sons Inc | 5 8-dihydronaphthyloxy acetic acids |
US3740437A (en) * | 1970-06-25 | 1973-06-19 | Syntex Corp | Naphthyloxyacetic acids and pharmaceutical compositions and methods thereof |
DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
-
1974
- 1974-12-06 GB GB52829/74A patent/GB1499508A/en not_active Expired
-
1975
- 1975-11-07 IE IE2434/75A patent/IE42454B1/en unknown
- 1975-11-10 US US05/630,685 patent/US4055595A/en not_active Expired - Lifetime
- 1975-11-11 ZA ZA00757089A patent/ZA757089B/xx unknown
- 1975-11-14 NO NO753837A patent/NO753837L/no unknown
- 1975-11-14 IL IL48477A patent/IL48477A/xx unknown
- 1975-11-27 AR AR261378A patent/AR213278A1/es active
- 1975-12-02 FI FI753393A patent/FI753393A/fi not_active Application Discontinuation
- 1975-12-03 PL PL1975196815A patent/PL102241B1/pl unknown
- 1975-12-03 DK DK546575A patent/DK546575A/da not_active Application Discontinuation
- 1975-12-03 PL PL1975196814A patent/PL102604B1/pl unknown
- 1975-12-03 NL NL7514070A patent/NL7514070A/xx not_active Application Discontinuation
- 1975-12-03 PL PL1975185202A patent/PL102292B1/pl unknown
- 1975-12-04 SE SE7513676A patent/SE7513676L/sv not_active Application Discontinuation
- 1975-12-04 DD DD189886A patent/DD122963A5/xx unknown
- 1975-12-04 LU LU73936A patent/LU73936A1/xx unknown
- 1975-12-04 SU SU752195066A patent/SU764608A3/ru active
- 1975-12-05 BE BE162509A patent/BE836353A/xx unknown
- 1975-12-05 HU HUIE724A patent/HU170016B/hu unknown
- 1975-12-05 ES ES443237A patent/ES443237A1/es not_active Expired
- 1975-12-05 FR FR7537379A patent/FR2293196A1/fr active Granted
- 1975-12-05 CA CA241,151A patent/CA1064498A/en not_active Expired
- 1975-12-05 AT AT927475A patent/AT347432B/de not_active IP Right Cessation
- 1975-12-05 DE DE19752554882 patent/DE2554882A1/de not_active Ceased
- 1975-12-05 CH CH1588575A patent/CH618414A5/de not_active IP Right Cessation
- 1975-12-05 CS CS758281A patent/CS191948B2/cs unknown
- 1975-12-06 JP JP50145834A patent/JPS51125227A/ja active Pending
-
1977
- 1977-01-31 ES ES455487A patent/ES455487A1/es not_active Expired
- 1977-01-31 ES ES455486A patent/ES455486A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2293196B1 (fi) | 1978-07-28 |
BE836353A (fr) | 1976-06-08 |
AT347432B (de) | 1978-12-27 |
DD122963A5 (de) | 1976-11-12 |
IE42454L (en) | 1976-06-06 |
US4055595A (en) | 1977-10-25 |
PL102604B1 (pl) | 1979-04-30 |
IL48477A0 (en) | 1976-03-31 |
ZA757089B (en) | 1976-10-27 |
GB1499508A (en) | 1978-02-01 |
JPS51125227A (en) | 1976-11-01 |
ES443237A1 (es) | 1977-04-16 |
PL102241B1 (pl) | 1979-03-31 |
SE7513676L (sv) | 1976-06-08 |
FR2293196A1 (fr) | 1976-07-02 |
PL102292B1 (pl) | 1979-03-31 |
FI753393A (fi) | 1976-06-07 |
DE2554882A1 (de) | 1976-06-16 |
AR213278A1 (es) | 1979-01-15 |
DK546575A (da) | 1976-06-07 |
CH618414A5 (fi) | 1980-07-31 |
CS191948B2 (en) | 1979-07-31 |
HU170016B (fi) | 1977-03-28 |
ES455487A1 (es) | 1978-01-16 |
IL48477A (en) | 1979-09-30 |
IE42454B1 (en) | 1980-08-13 |
NL7514070A (nl) | 1976-06-09 |
SU764608A3 (ru) | 1980-09-15 |
AU8661975A (en) | 1977-05-19 |
ES455486A1 (es) | 1978-01-16 |
LU73936A1 (fi) | 1977-02-15 |
ATA927475A (de) | 1978-05-15 |
CA1064498A (en) | 1979-10-16 |
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