DE2519719A1 - Phenylalkanole und verfahren zu ihrer herstellung - Google Patents
Phenylalkanole und verfahren zu ihrer herstellungInfo
- Publication number
- DE2519719A1 DE2519719A1 DE19752519719 DE2519719A DE2519719A1 DE 2519719 A1 DE2519719 A1 DE 2519719A1 DE 19752519719 DE19752519719 DE 19752519719 DE 2519719 A DE2519719 A DE 2519719A DE 2519719 A1 DE2519719 A1 DE 2519719A1
- Authority
- DE
- Germany
- Prior art keywords
- butan
- biphenylyl
- chloro
- fluoro
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 amino compound Chemical class 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000460 chlorine Substances 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 7
- 229910001502 inorganic halide Inorganic materials 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000012954 diazonium Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 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 claims description 4
- 150000001989 diazonium salts Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 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 3
- 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 description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 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 2
- 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 claims description 2
- JJTNCAUQZZPMJQ-UHFFFAOYSA-N 4-chloro-2-[4-(2-fluorophenyl)phenyl]butan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1C1=CC=CC=C1F JJTNCAUQZZPMJQ-UHFFFAOYSA-N 0.000 claims description 2
- OMJVYDPQODSSFC-UHFFFAOYSA-N 4-hydroxy-4-(4-phenylphenyl)pentanenitrile Chemical compound C1=CC(C(O)(CCC#N)C)=CC=C1C1=CC=CC=C1 OMJVYDPQODSSFC-UHFFFAOYSA-N 0.000 claims description 2
- AKBOFEFCNLZNGG-UHFFFAOYSA-N 5-chloro-2-[4-(4-fluorophenyl)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1C1=CC=C(F)C=C1 AKBOFEFCNLZNGG-UHFFFAOYSA-N 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000126 substance 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
- 239000002253 acid Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
- 125000000068 chlorophenyl group Chemical group 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 150000002222 fluorine compounds Chemical class 0.000 description 4
- 238000011065 in-situ storage Methods 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
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 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
- 150000003839 salts Chemical class 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 238000010626 work up procedure Methods 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
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003797 solvolysis reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 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 2
- 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 2
- 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 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
- 238000003747 Grignard reaction Methods 0.000 description 2
- 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 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000005840 aryl radicals Chemical class 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
- 239000003054 catalyst Substances 0.000 description 2
- 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 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000008101 lactose 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 235000012222 talc Nutrition 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
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- JTLAIKFGRHDNQM-UHFFFAOYSA-N 1-bromo-2-fluoroethane Chemical compound FCCBr JTLAIKFGRHDNQM-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
- BBYSOZPWMLCXFU-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenyl)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1C1=CC=C(Cl)C=C1Cl BBYSOZPWMLCXFU-UHFFFAOYSA-N 0.000 description 1
- DXGYDQSUJXZFDP-UHFFFAOYSA-N 2-[4-(2,4-difluorophenyl)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1C1=CC=C(F)C=C1F DXGYDQSUJXZFDP-UHFFFAOYSA-N 0.000 description 1
- OZPKJSWCRWKHHI-UHFFFAOYSA-N 2-[4-(2-bromophenoxy)phenyl]-4-chlorobutan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1OC1=CC=CC=C1Br OZPKJSWCRWKHHI-UHFFFAOYSA-N 0.000 description 1
- KWMNTIXVWZNQDM-UHFFFAOYSA-N 2-[4-(2-bromophenoxy)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1OC1=CC=CC=C1Br KWMNTIXVWZNQDM-UHFFFAOYSA-N 0.000 description 1
- DXXMLMYJFFEZAQ-UHFFFAOYSA-N 2-[4-(2-bromophenoxy)phenyl]-5-chloropentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1OC1=CC=CC=C1Br DXXMLMYJFFEZAQ-UHFFFAOYSA-N 0.000 description 1
- WPDWYMSHTIWGNA-UHFFFAOYSA-N 2-[4-(2-chlorophenoxy)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1OC1=CC=CC=C1Cl WPDWYMSHTIWGNA-UHFFFAOYSA-N 0.000 description 1
- GYNUTLGEKUTYEZ-UHFFFAOYSA-N 2-[4-(2-chlorophenyl)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1C1=CC=CC=C1Cl GYNUTLGEKUTYEZ-UHFFFAOYSA-N 0.000 description 1
- GXAFAMAYABUYOM-UHFFFAOYSA-N 2-[4-(3-bromophenoxy)phenyl]-4-chlorobutan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1OC1=CC=CC(Br)=C1 GXAFAMAYABUYOM-UHFFFAOYSA-N 0.000 description 1
- OBDQCHOFXCXICZ-UHFFFAOYSA-N 2-[4-(3-bromophenoxy)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1OC1=CC=CC(Br)=C1 OBDQCHOFXCXICZ-UHFFFAOYSA-N 0.000 description 1
- DDJZLBWFXPGGNX-UHFFFAOYSA-N 2-[4-(3-bromophenoxy)phenyl]-5-chloropentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1OC1=CC=CC(Br)=C1 DDJZLBWFXPGGNX-UHFFFAOYSA-N 0.000 description 1
- HOLNQFPHNFOJGI-UHFFFAOYSA-N 2-[4-(3-bromophenyl)phenyl]-4-chlorobutan-2-ol Chemical compound C1=CC(C(O)(CCCl)C)=CC=C1C1=CC=CC(Br)=C1 HOLNQFPHNFOJGI-UHFFFAOYSA-N 0.000 description 1
- NIBNBULODPHOBZ-UHFFFAOYSA-N 2-[4-(3-bromophenyl)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1C1=CC=CC(Br)=C1 NIBNBULODPHOBZ-UHFFFAOYSA-N 0.000 description 1
- MBNGQBUHSROHIJ-UHFFFAOYSA-N 2-[4-(3-bromophenyl)phenyl]-5-chloropentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1C1=CC=CC(Br)=C1 MBNGQBUHSROHIJ-UHFFFAOYSA-N 0.000 description 1
- WLIQACFNJDEYNY-UHFFFAOYSA-N 2-[4-(3-chlorophenoxy)phenyl]-4-fluorobutan-2-ol Chemical compound C1=CC(C(O)(CCF)C)=CC=C1OC1=CC=CC(Cl)=C1 WLIQACFNJDEYNY-UHFFFAOYSA-N 0.000 description 1
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- PMYVXSYNDAANAK-UHFFFAOYSA-N 5-chloro-2-[4-(2-fluorophenoxy)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1OC1=CC=CC=C1F PMYVXSYNDAANAK-UHFFFAOYSA-N 0.000 description 1
- YCAMXSXCFFXCEC-UHFFFAOYSA-N 5-chloro-2-[4-(2-methylphenoxy)phenyl]pentan-2-ol Chemical compound CC1=CC=CC=C1OC1=CC=C(C(C)(O)CCCCl)C=C1 YCAMXSXCFFXCEC-UHFFFAOYSA-N 0.000 description 1
- UDNSILLSXBQKPF-UHFFFAOYSA-N 5-chloro-2-[4-(2-methylphenyl)phenyl]pentan-2-ol Chemical compound CC1=CC=CC=C1C1=CC=C(C(C)(O)CCCCl)C=C1 UDNSILLSXBQKPF-UHFFFAOYSA-N 0.000 description 1
- CWBBBKJQOPQTAZ-UHFFFAOYSA-N 5-chloro-2-[4-(3-chlorophenoxy)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1OC1=CC=CC(Cl)=C1 CWBBBKJQOPQTAZ-UHFFFAOYSA-N 0.000 description 1
- LTWIDAPCPSAYKC-UHFFFAOYSA-N 5-chloro-2-[4-(3-chlorophenyl)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1C1=CC=CC(Cl)=C1 LTWIDAPCPSAYKC-UHFFFAOYSA-N 0.000 description 1
- OVBNLIKAVBQETL-UHFFFAOYSA-N 5-chloro-2-[4-(3-fluorophenoxy)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1OC1=CC=CC(F)=C1 OVBNLIKAVBQETL-UHFFFAOYSA-N 0.000 description 1
- FZWSCFZIJCREMH-UHFFFAOYSA-N 5-chloro-2-[4-(3-methylphenoxy)phenyl]pentan-2-ol Chemical compound CC1=CC=CC(OC=2C=CC(=CC=2)C(C)(O)CCCCl)=C1 FZWSCFZIJCREMH-UHFFFAOYSA-N 0.000 description 1
- KVRDAHDRGAGCGR-UHFFFAOYSA-N 5-chloro-2-[4-(4-chlorophenoxy)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1OC1=CC=C(Cl)C=C1 KVRDAHDRGAGCGR-UHFFFAOYSA-N 0.000 description 1
- IZMVSJKOIBVCRJ-UHFFFAOYSA-N 5-chloro-2-[4-(4-fluorophenoxy)phenyl]pentan-2-ol Chemical compound C1=CC(C(O)(CCCCl)C)=CC=C1OC1=CC=C(F)C=C1 IZMVSJKOIBVCRJ-UHFFFAOYSA-N 0.000 description 1
- UEZUAALQGLWBDS-UHFFFAOYSA-N 5-chloro-2-[4-(4-methylphenoxy)phenyl]pentan-2-ol Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C(C)(O)CCCCl)C=C1 UEZUAALQGLWBDS-UHFFFAOYSA-N 0.000 description 1
- PJLUWMNIPPDKMJ-UHFFFAOYSA-N 5-chloro-2-[4-(4-methylphenyl)phenyl]pentan-2-ol Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(C)(O)CCCCl)C=C1 PJLUWMNIPPDKMJ-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
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
- VCGMAJZVKBBFTK-UHFFFAOYSA-N CC(CCCl)(C1(CC=C(C=C1)C2=CC=CC=C2)Cl)O Chemical compound CC(CCCl)(C1(CC=C(C=C1)C2=CC=CC=C2)Cl)O VCGMAJZVKBBFTK-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 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
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229910010082 LiAlH 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
- 239000004264 Petrolatum Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 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
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 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
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 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
- 239000004305 biphenyl Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 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
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- 239000003937 drug carrier 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
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000006197 hydroboration reaction 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
- 239000005457 ice water Substances 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 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
- 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
- 239000002609 medium Substances 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 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
- 239000003921 oil Substances 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
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 239000011877 solvent mixture Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 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
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752519719 DE2519719A1 (de) | 1975-05-02 | 1975-05-02 | Phenylalkanole und verfahren zu ihrer herstellung |
| DK156176A DK156176A (da) | 1975-05-02 | 1976-03-31 | Fremgangsmade til fremstilling af phenylalkanoler |
| FR7611675A FR2309217A1 (fr) | 1975-05-02 | 1976-04-21 | Nouveaux phenylalcanols, leur application en tant que medicaments et leur procede de preparation |
| ES447365A ES447365A1 (es) | 1975-05-02 | 1976-04-27 | Procedimiento para la obtencion de tenilalcanoles. |
| US05/681,175 US4060633A (en) | 1975-05-02 | 1976-04-28 | Phenylalkanol nitriles |
| AT314876A AT348510B (de) | 1975-05-02 | 1976-04-29 | Verfahren zur herstellung von neuen phenylalkanolen |
| NL7604623A NL7604623A (nl) | 1975-05-02 | 1976-04-29 | Fenylalkanolen met farmacologische eigenschap- pen en werkwijzen om deze te bereiden. |
| CS762831A CS200492B2 (en) | 1975-05-02 | 1976-04-29 | Process for preparing phenolalcohols |
| SE7604954A SE7604954L (sv) | 1975-05-02 | 1976-04-29 | Fenylalkanolder och forfarande for framstellning derav |
| GB1780576A GB1477997A (en) | 1975-05-02 | 1976-04-30 | Phenylalkanols and their preparation |
| HU76ME1971A HU176685B (en) | 1975-05-02 | 1976-04-30 | Process for producing phenyl-alkanole derivatives |
| BE166609A BE841329A (nl) | 1975-05-02 | 1976-04-30 | Fenylalkanolen met farmacologische eigenschappen en werkwijzen om deze te bereiden |
| IL49504A IL49504A (en) | 1975-05-02 | 1976-04-30 | Phenylalkanols and their preparation |
| DD192623A DD124593A5 (enExample) | 1975-05-02 | 1976-04-30 | |
| LU74869A LU74869A1 (enExample) | 1975-05-02 | 1976-04-30 | |
| ZA762605A ZA762605B (en) | 1975-05-02 | 1976-04-30 | Phenylalkanols and their preparation |
| CA251,509A CA1077962A (en) | 1975-05-02 | 1976-04-30 | Phenylalkanols and a process for their preparation |
| AU13508/76A AU499362B2 (en) | 1975-05-02 | 1976-04-30 | Aryl & aryloxy phenyl alkanols |
| IE927/76A IE44100B1 (en) | 1975-05-02 | 1976-04-30 | Phenylalkanols and their preparation |
| JP51051227A JPS51138637A (en) | 1975-05-02 | 1976-05-04 | Phenyl alkanols and process for preparation thereof |
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 |
|---|---|
| DE2519719A1 true DE2519719A1 (de) | 1976-11-18 |
Family
ID=5945662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752519719 Withdrawn DE2519719A1 (de) | 1975-05-02 | 1975-05-02 | Phenylalkanole und verfahren zu ihrer herstellung |
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 SE SE7604954A patent/SE7604954L/xx unknown
- 1976-04-29 NL NL7604623A patent/NL7604623A/xx not_active Application Discontinuation
- 1976-04-29 AT AT314876A patent/AT348510B/de not_active IP Right Cessation
- 1976-04-29 CS CS762831A patent/CS200492B2/cs unknown
- 1976-04-30 DD DD192623A patent/DD124593A5/xx unknown
- 1976-04-30 CA CA251,509A patent/CA1077962A/en not_active Expired
- 1976-04-30 GB GB1780576A patent/GB1477997A/en not_active Expired
- 1976-04-30 IE IE927/76A patent/IE44100B1/en unknown
- 1976-04-30 BE BE166609A patent/BE841329A/xx unknown
- 1976-04-30 ZA ZA762605A patent/ZA762605B/xx unknown
- 1976-04-30 AU AU13508/76A patent/AU499362B2/en not_active Expired
- 1976-04-30 IL IL49504A patent/IL49504A/xx unknown
- 1976-04-30 HU HU76ME1971A patent/HU176685B/hu unknown
- 1976-04-30 LU LU74869A patent/LU74869A1/xx unknown
- 1976-05-04 JP JP51051227A patent/JPS51138637A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1477997A (en) | 1977-06-29 |
| CS200492B2 (en) | 1980-09-15 |
| IE44100B1 (en) | 1981-08-12 |
| FR2309217B1 (enExample) | 1979-09-21 |
| US4060633A (en) | 1977-11-29 |
| IL49504A (en) | 1979-01-31 |
| DD124593A5 (enExample) | 1977-03-02 |
| BE841329A (nl) | 1976-11-03 |
| NL7604623A (nl) | 1976-11-04 |
| CA1077962A (en) | 1980-05-20 |
| FR2309217A1 (fr) | 1976-11-26 |
| ZA762605B (en) | 1977-04-27 |
| DK156176A (da) | 1976-11-03 |
| ATA314876A (de) | 1978-07-15 |
| JPS51138637A (en) | 1976-11-30 |
| AU499362B2 (en) | 1979-04-12 |
| AU1350876A (en) | 1977-11-03 |
| LU74869A1 (enExample) | 1977-12-02 |
| IE44100L (en) | 1976-11-02 |
| IL49504A0 (en) | 1976-06-30 |
| AT348510B (de) | 1979-02-26 |
| HU176685B (en) | 1981-04-28 |
| ES447365A1 (es) | 1977-12-01 |
| SE7604954L (sv) | 1976-11-03 |
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