CA1077962A - Phenylalkanols and a process for their preparation - Google Patents
Phenylalkanols and a process for their preparationInfo
- Publication number
- CA1077962A CA1077962A CA251,509A CA251509A CA1077962A CA 1077962 A CA1077962 A CA 1077962A CA 251509 A CA251509 A CA 251509A CA 1077962 A CA1077962 A CA 1077962A
- Authority
- CA
- Canada
- Prior art keywords
- butan
- biphenylyl
- fluoro
- compound
- chloro
- 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
- 238000000034 method Methods 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- -1 amino compound Chemical class 0.000 claims description 67
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000012954 diazonium Substances 0.000 claims description 7
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 7
- DQTDXOWOWSXBMK-UHFFFAOYSA-N 4-chloro-2-[4-(4-fluorophenyl)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1C1=CC=C(F)C=C1 DQTDXOWOWSXBMK-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001989 diazonium salts Chemical class 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- PAMIXKLBWYQVFJ-UHFFFAOYSA-N 4-bromo-2-[4-(4-fluorophenyl)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCBr)C)=CC=C1C1=CC=C(F)C=C1 PAMIXKLBWYQVFJ-UHFFFAOYSA-N 0.000 claims description 3
- QPGWXXARBBYJDR-UHFFFAOYSA-N 4-chloro-2-[4-(2,4-difluorophenyl)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1C1=CC=C(F)C=C1F QPGWXXARBBYJDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 125000004212 difluorophenyl group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 10
- MZRHRARWRKAPKT-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-4-hydroxypentanenitrile Chemical compound C1=CC(C(O)(CCC#N)C)=CC=C1C1=CC=C(Cl)C=C1 MZRHRARWRKAPKT-UHFFFAOYSA-N 0.000 claims 2
- WOIHBXFCKZABSL-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)phenyl]-4-hydroxypentanenitrile Chemical compound C1=CC(C(O)(CCC#N)C)=CC=C1C1=CC=C(F)C=C1 WOIHBXFCKZABSL-UHFFFAOYSA-N 0.000 claims 2
- SOOKUNKYMSEFLL-UHFFFAOYSA-N 4-fluoro-2-[4-(4-fluorophenyl)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1C1=CC=C(F)C=C1 SOOKUNKYMSEFLL-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 230000000875 corresponding effect Effects 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 229960000443 hydrochloric acid Drugs 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 150000002902 organometallic compounds Chemical class 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 3
- 238000003797 solvolysis reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- ZXQJDBAHSIFABS-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)phenyl]butane-1,3-diol Chemical compound C1=CC(C(O)(CCO)C)=CC=C1C1=CC=C(F)C=C1 ZXQJDBAHSIFABS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229910020667 PBr3 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000001741 anti-phlogistic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- JTLAIKFGRHDNQM-UHFFFAOYSA-N 1-bromo-2-fluoroethane Chemical compound FCCBr JTLAIKFGRHDNQM-UHFFFAOYSA-N 0.000 description 1
- XFGPSHWWPIFPNL-UHFFFAOYSA-N 1-bromo-4-(4-fluorophenyl)benzene Chemical group C1=CC(F)=CC=C1C1=CC=C(Br)C=C1 XFGPSHWWPIFPNL-UHFFFAOYSA-N 0.000 description 1
- RUYZJEIKQYLEGZ-UHFFFAOYSA-N 1-fluoro-4-phenylbenzene Chemical group C1=CC(F)=CC=C1C1=CC=CC=C1 RUYZJEIKQYLEGZ-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- PNRPKQBRKBYUNA-UHFFFAOYSA-N 2-[4-(3-chlorophenyl)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1C1=CC=CC(Cl)=C1 PNRPKQBRKBYUNA-UHFFFAOYSA-N 0.000 description 1
- CHPUWKXSTQQJDS-UHFFFAOYSA-N 2-[4-(4-aminophenyl)phenyl]-4-chlorobutan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1C1=CC=C(N)C=C1 CHPUWKXSTQQJDS-UHFFFAOYSA-N 0.000 description 1
- RMZFFPBJTXDICE-UHFFFAOYSA-N 2-[4-(4-bromophenoxy)phenyl]-4-chlorobutan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1OC1=CC=C(Br)C=C1 RMZFFPBJTXDICE-UHFFFAOYSA-N 0.000 description 1
- SYYPWYHTGPCSCF-UHFFFAOYSA-N 2-[4-(4-bromophenyl)phenyl]-4-chlorobutan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1C1=CC=C(Br)C=C1 SYYPWYHTGPCSCF-UHFFFAOYSA-N 0.000 description 1
- QLXDJCFXMRWFKL-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1OC1=CC=C(Cl)C=C1 QLXDJCFXMRWFKL-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- REIISRRKPMDTCU-UHFFFAOYSA-N 2-chloro-1-(4-phenylphenyl)propan-1-one Chemical group C1=CC(C(=O)C(Cl)C)=CC=C1C1=CC=CC=C1 REIISRRKPMDTCU-UHFFFAOYSA-N 0.000 description 1
- UHNMZBUVOURROG-UHFFFAOYSA-N 2-chloro-1-[4-(2,4-dichlorophenyl)phenyl]propan-1-one Chemical group C1=CC(C(=O)C(Cl)C)=CC=C1C1=CC=C(Cl)C=C1Cl UHNMZBUVOURROG-UHFFFAOYSA-N 0.000 description 1
- DFDDXJWNFLVVJD-UHFFFAOYSA-N 2-chloro-1-[4-(2,4-difluorophenyl)phenyl]propan-1-one Chemical group C1=CC(C(=O)C(Cl)C)=CC=C1C1=CC=C(F)C=C1F DFDDXJWNFLVVJD-UHFFFAOYSA-N 0.000 description 1
- OYUVHQCIKYICGW-UHFFFAOYSA-N 2-chloro-1-[4-(2-fluorophenyl)phenyl]propan-1-one Chemical group C1=CC(C(=O)C(Cl)C)=CC=C1C1=CC=CC=C1F OYUVHQCIKYICGW-UHFFFAOYSA-N 0.000 description 1
- GOQWZZCATBXFNE-UHFFFAOYSA-N 2-chloro-1-[4-(3-fluorophenyl)phenyl]propan-1-one Chemical group C1=CC(C(=O)C(Cl)C)=CC=C1C1=CC=CC(F)=C1 GOQWZZCATBXFNE-UHFFFAOYSA-N 0.000 description 1
- CKXVHRTYTKBRDC-UHFFFAOYSA-N 2-chloro-1-[4-(4-fluoro-2-methylphenyl)phenyl]propan-1-one Chemical group C1=CC(C(=O)C(Cl)C)=CC=C1C1=CC=C(F)C=C1C CKXVHRTYTKBRDC-UHFFFAOYSA-N 0.000 description 1
- BQBABWYPRYAVRC-UHFFFAOYSA-N 2-chloro-1-[4-(4-fluorophenyl)phenyl]propan-1-one Chemical group C1=CC(C(=O)C(Cl)C)=CC=C1C1=CC=C(F)C=C1 BQBABWYPRYAVRC-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- WVXZASICUZBZEU-UHFFFAOYSA-N 4-[4-(2-chlorophenoxy)phenyl]-4-hydroxypentanenitrile Chemical compound C1=CC(C(O)(CCC#N)C)=CC=C1OC1=CC=CC=C1Cl WVXZASICUZBZEU-UHFFFAOYSA-N 0.000 description 1
- XXUIBSMPHOTSLT-UHFFFAOYSA-N 4-[4-(3-fluorophenoxy)phenyl]-4-hydroxypentanenitrile Chemical compound C1=CC(C(O)(CCC#N)C)=CC=C1OC1=CC=CC(F)=C1 XXUIBSMPHOTSLT-UHFFFAOYSA-N 0.000 description 1
- KLDFMZVUVVJLOZ-UHFFFAOYSA-N 4-[4-(4-bromophenyl)phenyl]-4-hydroxypentanenitrile Chemical compound C1=CC(C(O)(CCC#N)C)=CC=C1C1=CC=C(Br)C=C1 KLDFMZVUVVJLOZ-UHFFFAOYSA-N 0.000 description 1
- SQHWHPMRSSHQEY-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]-4-hydroxypentanenitrile Chemical compound C1=CC(C(O)(CCC#N)C)=CC=C1OC1=CC=C(Cl)C=C1 SQHWHPMRSSHQEY-UHFFFAOYSA-N 0.000 description 1
- ZSRBVFFMJIVIPK-UHFFFAOYSA-N 4-[4-(4-fluoro-2-methylphenyl)phenyl]-4-hydroxypentanenitrile Chemical compound CC1=CC(F)=CC=C1C1=CC=C(C(C)(O)CCC#N)C=C1 ZSRBVFFMJIVIPK-UHFFFAOYSA-N 0.000 description 1
- QDZKSMGCCCBQAZ-UHFFFAOYSA-N 4-bromo-2-[4-(3-fluorophenyl)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCBr)C)=CC=C1C1=CC=CC(F)=C1 QDZKSMGCCCBQAZ-UHFFFAOYSA-N 0.000 description 1
- KZCAUNUZNALOHD-UHFFFAOYSA-N 4-bromo-2-[4-(4-chlorophenyl)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCBr)C)=CC=C1C1=CC=C(Cl)C=C1 KZCAUNUZNALOHD-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- SNXDTNWFTUJRSO-UHFFFAOYSA-N 4-chloro-2-(4-phenylphenyl)butan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1C1=CC=CC=C1 SNXDTNWFTUJRSO-UHFFFAOYSA-N 0.000 description 1
- JRDWNQUGTFQULV-UHFFFAOYSA-N 4-chloro-2-[4-(2-chlorophenoxy)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1OC1=CC=CC=C1Cl JRDWNQUGTFQULV-UHFFFAOYSA-N 0.000 description 1
- GWSJWCDJMVKSFA-UHFFFAOYSA-N 4-chloro-2-[4-(3-chlorophenyl)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1C1=CC=CC(Cl)=C1 GWSJWCDJMVKSFA-UHFFFAOYSA-N 0.000 description 1
- MUZKFEYRYFEARS-UHFFFAOYSA-N 4-fluoro-2-[4-(3-methylphenoxy)phenyl]butan-2-ol Chemical compound CC1=CC=CC(OC=2C=CC(=CC=2)C(C)(O)CCF)=C1 MUZKFEYRYFEARS-UHFFFAOYSA-N 0.000 description 1
- NFZJIFANBUOQEU-UHFFFAOYSA-N 4-hydroxy-4-(4-phenoxyphenyl)pentanenitrile Chemical compound C1=CC(C(O)(CCC#N)C)=CC=C1OC1=CC=CC=C1 NFZJIFANBUOQEU-UHFFFAOYSA-N 0.000 description 1
- AQTAJKALYAESQV-UHFFFAOYSA-N 4-hydroxy-4-[4-(4-methylphenoxy)phenyl]pentanenitrile Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C(C)(O)CCC#N)C=C1 AQTAJKALYAESQV-UHFFFAOYSA-N 0.000 description 1
- INDKMEUWSXILNC-UHFFFAOYSA-N 5-chloro-2-[4-(2,4-dichlorophenyl)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1C1=CC=C(Cl)C=C1Cl INDKMEUWSXILNC-UHFFFAOYSA-N 0.000 description 1
- HVJJKJKQXHTXHY-UHFFFAOYSA-N 5-chloro-2-[4-(2-chlorophenoxy)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1OC1=CC=CC=C1Cl HVJJKJKQXHTXHY-UHFFFAOYSA-N 0.000 description 1
- DJUOHDYDFHETON-UHFFFAOYSA-N 5-chloro-2-[4-(3-methylphenyl)phenyl]pentan-2-ol Chemical compound CC1=CC=CC(C=2C=CC(=CC=2)C(C)(O)CCCCl)=C1 DJUOHDYDFHETON-UHFFFAOYSA-N 0.000 description 1
- YFHAZJRCPSCTBM-UHFFFAOYSA-N 5-chloro-2-[4-(4-chlorophenyl)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1C1=CC=C(Cl)C=C1 YFHAZJRCPSCTBM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229910014263 BrF3 Inorganic materials 0.000 description 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- OLBGGALVDBILHX-UHFFFAOYSA-N FCC[Li] Chemical compound FCC[Li] OLBGGALVDBILHX-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 229910004039 HBF4 Inorganic materials 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000006680 Reformatsky reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- VWDBKORTLOENDJ-UHFFFAOYSA-N [3-[4-(4-fluorophenyl)phenyl]-3-hydroxybutyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC(C)(O)C1=CC=C(C=2C=CC(F)=CC=2)C=C1 VWDBKORTLOENDJ-UHFFFAOYSA-N 0.000 description 1
- JZJDKRHJGYVVFS-UHFFFAOYSA-N [3-[4-(4-fluorophenyl)phenyl]-3-hydroxybutyl] methanesulfonate Chemical compound C1=CC(C(O)(CCOS(C)(=O)=O)C)=CC=C1C1=CC=C(F)C=C1 JZJDKRHJGYVVFS-UHFFFAOYSA-N 0.000 description 1
- BZAFEKJPYMFYFE-UHFFFAOYSA-M [Br-].C1=CC(F)=CC=C1C1=CC=C([Mg+])C=C1 Chemical compound [Br-].C1=CC(F)=CC=C1C1=CC=C([Mg+])C=C1 BZAFEKJPYMFYFE-UHFFFAOYSA-M 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- DYWNVMKTPAXRIJ-UHFFFAOYSA-N benzenesulfonic acid;3-[4-(4-fluorophenyl)phenyl]butane-1,3-diol Chemical compound OS(=O)(=O)C1=CC=CC=C1.C1=CC(C(O)(CCO)C)=CC=C1C1=CC=C(F)C=C1 DYWNVMKTPAXRIJ-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 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 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- KWNCKGXVDXRFDL-UHFFFAOYSA-N ethyl 3-[4-(4-fluorophenyl)phenyl]-3-hydroxybutanoate Chemical compound C1=CC(C(C)(O)CC(=O)OCC)=CC=C1C1=CC=C(F)C=C1 KWNCKGXVDXRFDL-UHFFFAOYSA-N 0.000 description 1
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- CMMXCVYESRODNH-UHFFFAOYSA-N trichloroepoxyethane Chemical class ClC1OC1(Cl)Cl CMMXCVYESRODNH-UHFFFAOYSA-N 0.000 description 1
- FQFKTKUFHWNTBN-UHFFFAOYSA-N trifluoro-$l^{3}-bromane Chemical compound FBr(F)F FQFKTKUFHWNTBN-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752519719 DE2519719A1 (de) | 1975-05-02 | 1975-05-02 | Phenylalkanole und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077962A true CA1077962A (en) | 1980-05-20 |
Family
ID=5945662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,509A Expired CA1077962A (en) | 1975-05-02 | 1976-04-30 | Phenylalkanols and a process for their preparation |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4060633A (enExample) |
| JP (1) | JPS51138637A (enExample) |
| AT (1) | AT348510B (enExample) |
| AU (1) | AU499362B2 (enExample) |
| BE (1) | BE841329A (enExample) |
| CA (1) | CA1077962A (enExample) |
| CS (1) | CS200492B2 (enExample) |
| DD (1) | DD124593A5 (enExample) |
| DE (1) | DE2519719A1 (enExample) |
| DK (1) | DK156176A (enExample) |
| ES (1) | ES447365A1 (enExample) |
| FR (1) | FR2309217A1 (enExample) |
| GB (1) | GB1477997A (enExample) |
| HU (1) | HU176685B (enExample) |
| IE (1) | IE44100B1 (enExample) |
| IL (1) | IL49504A (enExample) |
| LU (1) | LU74869A1 (enExample) |
| NL (1) | NL7604623A (enExample) |
| SE (1) | SE7604954L (enExample) |
| ZA (1) | ZA762605B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2626018A1 (de) * | 1976-06-10 | 1977-12-22 | Merck Patent Gmbh | Alkinole und verfahren zu ihrer herstellung |
| US5380755A (en) * | 1992-07-24 | 1995-01-10 | The Du Pont Merck Pharmaceutical Company | Alkyl and alkylbenzyl ethers of substituted hydroquinones |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1040735A (en) * | 1964-07-23 | 1966-09-01 | British Drug Houses Ltd | 4-aryl-3-hydroxybutyric acid and esters, amides and salts thereof |
-
1975
- 1975-05-02 DE DE19752519719 patent/DE2519719A1/de not_active Withdrawn
-
1976
- 1976-03-31 DK DK156176A patent/DK156176A/da not_active IP Right Cessation
- 1976-04-21 FR FR7611675A patent/FR2309217A1/fr active Granted
- 1976-04-27 ES ES447365A patent/ES447365A1/es not_active Expired
- 1976-04-28 US US05/681,175 patent/US4060633A/en not_active Expired - Lifetime
- 1976-04-29 AT AT314876A patent/AT348510B/de not_active IP Right Cessation
- 1976-04-29 NL NL7604623A patent/NL7604623A/xx not_active Application Discontinuation
- 1976-04-29 SE SE7604954A patent/SE7604954L/xx unknown
- 1976-04-29 CS CS762831A patent/CS200492B2/cs unknown
- 1976-04-30 DD DD192623A patent/DD124593A5/xx unknown
- 1976-04-30 ZA ZA762605A patent/ZA762605B/xx unknown
- 1976-04-30 IL IL49504A patent/IL49504A/xx unknown
- 1976-04-30 HU HU76ME1971A patent/HU176685B/hu unknown
- 1976-04-30 CA CA251,509A patent/CA1077962A/en not_active Expired
- 1976-04-30 IE IE927/76A patent/IE44100B1/en unknown
- 1976-04-30 AU AU13508/76A patent/AU499362B2/en not_active Expired
- 1976-04-30 LU LU74869A patent/LU74869A1/xx unknown
- 1976-04-30 BE BE166609A patent/BE841329A/xx unknown
- 1976-04-30 GB GB1780576A patent/GB1477997A/en not_active Expired
- 1976-05-04 JP JP51051227A patent/JPS51138637A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATA314876A (de) | 1978-07-15 |
| SE7604954L (sv) | 1976-11-03 |
| DE2519719A1 (de) | 1976-11-18 |
| CS200492B2 (en) | 1980-09-15 |
| IE44100B1 (en) | 1981-08-12 |
| IE44100L (en) | 1976-11-02 |
| LU74869A1 (enExample) | 1977-12-02 |
| FR2309217B1 (enExample) | 1979-09-21 |
| AT348510B (de) | 1979-02-26 |
| US4060633A (en) | 1977-11-29 |
| IL49504A0 (en) | 1976-06-30 |
| NL7604623A (nl) | 1976-11-04 |
| FR2309217A1 (fr) | 1976-11-26 |
| ZA762605B (en) | 1977-04-27 |
| HU176685B (en) | 1981-04-28 |
| GB1477997A (en) | 1977-06-29 |
| JPS51138637A (en) | 1976-11-30 |
| AU1350876A (en) | 1977-11-03 |
| DD124593A5 (enExample) | 1977-03-02 |
| IL49504A (en) | 1979-01-31 |
| ES447365A1 (es) | 1977-12-01 |
| DK156176A (da) | 1976-11-03 |
| BE841329A (nl) | 1976-11-03 |
| AU499362B2 (en) | 1979-04-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |