JPS5910356B2 - ベンゾフラン誘導体の製造方法 - Google Patents
ベンゾフラン誘導体の製造方法Info
- Publication number
- JPS5910356B2 JPS5910356B2 JP50026124A JP2612475A JPS5910356B2 JP S5910356 B2 JPS5910356 B2 JP S5910356B2 JP 50026124 A JP50026124 A JP 50026124A JP 2612475 A JP2612475 A JP 2612475A JP S5910356 B2 JPS5910356 B2 JP S5910356B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- formulas
- tables
- mathematical
- chemical
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- 150000001907 coumarones Chemical class 0.000 title 1
- -1 cyano, hydroxy Chemical group 0.000 claims description 166
- 125000003545 alkoxy group Chemical group 0.000 claims description 160
- 150000001875 compounds Chemical class 0.000 claims description 143
- 239000002253 acid Substances 0.000 claims description 110
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 60
- 239000000126 substance Substances 0.000 claims description 57
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 150000002431 hydrogen Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 239000002585 base Substances 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 15
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 229910052727 yttrium Inorganic materials 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 126
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 122
- 239000000243 solution Substances 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 79
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 74
- 125000003282 alkyl amino group Chemical group 0.000 description 53
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- 238000010992 reflux Methods 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- 238000002844 melting Methods 0.000 description 43
- 230000008018 melting Effects 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 34
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- 125000002252 acyl group Chemical group 0.000 description 25
- 125000004414 alkyl thio group Chemical group 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 20
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 19
- 239000012299 nitrogen atmosphere Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 17
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 14
- 125000005530 alkylenedioxy group Chemical group 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- KWGCXQZMMAVJTB-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)propanoic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3OC2=C1 KWGCXQZMMAVJTB-UHFFFAOYSA-N 0.000 description 11
- 125000004494 ethyl ester group Chemical group 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 150000001350 alkyl halides Chemical class 0.000 description 8
- 239000003610 charcoal Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 241000699670 Mus sp. Species 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 150000007522 mineralic acids Chemical class 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 229920000137 polyphosphoric acid Polymers 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- MVJQACPZNRHBAZ-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)acetic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 MVJQACPZNRHBAZ-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010533 azeotropic distillation Methods 0.000 description 6
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 6
- 230000002140 halogenating effect Effects 0.000 description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- KJNBXCPVUPRFSZ-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)acetonitrile Chemical compound N#CCC1=CC=C2C3=CC(Cl)=CC=C3OC2=C1 KJNBXCPVUPRFSZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- PWXYWLZWPWNUAY-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)acetamide Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)N)C=C3OC2=C1 PWXYWLZWPWNUAY-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 239000002260 anti-inflammatory agent Substances 0.000 description 4
- 239000003435 antirheumatic agent Substances 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- GJBBHPOFMGGQHR-UHFFFAOYSA-N (8-chlorodibenzofuran-3-yl)methanol Chemical compound ClC=1C=CC2=C(C3=C(O2)C=C(C=C3)CO)C1 GJBBHPOFMGGQHR-UHFFFAOYSA-N 0.000 description 3
- AQCBHJLPHDCMMW-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)propan-1-ol Chemical compound C1=C(Cl)C=C2C3=CC=C(C(CO)C)C=C3OC2=C1 AQCBHJLPHDCMMW-UHFFFAOYSA-N 0.000 description 3
- OMWLLFVOURPWJD-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)propanamide Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(N)=O)C)C=C3OC2=C1 OMWLLFVOURPWJD-UHFFFAOYSA-N 0.000 description 3
- SMCZYDXTSPOTPW-UHFFFAOYSA-N 2-dibenzofuran-3-ylpropanoic acid Chemical compound C1=CC=C2C3=CC=C(C(C(O)=O)C)C=C3OC2=C1 SMCZYDXTSPOTPW-UHFFFAOYSA-N 0.000 description 3
- XQGUJRXZOFSZMV-UHFFFAOYSA-N CC(N)C1=CC=CC=C1.C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3OC2=C1 Chemical compound CC(N)C1=CC=CC=C1.C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3OC2=C1 XQGUJRXZOFSZMV-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 3
- 229950005499 carbon tetrachloride Drugs 0.000 description 3
- 238000013375 chromatographic separation Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000004826 dibenzofurans Chemical class 0.000 description 3
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
- ZIYOAMMZCMIUDK-UHFFFAOYSA-N ethyl 2-(3-bromo-4-oxocyclohexyl)acetate Chemical compound CCOC(=O)CC1CCC(=O)C(Br)C1 ZIYOAMMZCMIUDK-UHFFFAOYSA-N 0.000 description 3
- QFMWIIPPXLNJQN-UHFFFAOYSA-N ethyl 2-(8-chlorodibenzofuran-3-yl)propanoate Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C)C(=O)OCC)C=C3OC2=C1 QFMWIIPPXLNJQN-UHFFFAOYSA-N 0.000 description 3
- NMNOZKAXLSCVPZ-UHFFFAOYSA-N ethyl 3-(8-chlorodibenzofuran-3-yl)propanoate Chemical compound C1=C(Cl)C=C2C3=CC=C(CCC(=O)OCC)C=C3OC2=C1 NMNOZKAXLSCVPZ-UHFFFAOYSA-N 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
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- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
- 238000004166 bioassay Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer 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
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- ZGPSDEFFXLRCAC-UHFFFAOYSA-N dibenzofuran-2-sulfonamide Chemical compound C1=CC=C2C3=CC(S(=O)(=O)N)=CC=C3OC2=C1 ZGPSDEFFXLRCAC-UHFFFAOYSA-N 0.000 description 1
- GRGOAGFQWWNEEP-UHFFFAOYSA-N dibenzofuran-2-yl(phenyl)methanone Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1C(=O)C1=CC=CC=C1 GRGOAGFQWWNEEP-UHFFFAOYSA-N 0.000 description 1
- IPAZMLAVBPDMLK-UHFFFAOYSA-N dibenzofuran-3-carboxylic acid Chemical compound C1=CC=C2C3=CC=C(C(=O)O)C=C3OC2=C1 IPAZMLAVBPDMLK-UHFFFAOYSA-N 0.000 description 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- DNAPLNCLIFMNQY-UHFFFAOYSA-N diethyl 2-(8-chlorodibenzofuran-3-carbonyl)propanedioate Chemical compound C(C)OC(C(C(=O)OCC)C(=O)C=1C=CC2=C(OC3=C2C=C(C=C3)Cl)C1)=O DNAPLNCLIFMNQY-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- WFSULZXQWNUZPF-UHFFFAOYSA-N ethoxyaluminum Chemical compound CCO[Al] WFSULZXQWNUZPF-UHFFFAOYSA-N 0.000 description 1
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
- XHNJFNLTFMAPQB-UHFFFAOYSA-N ethyl 2-(4-oxocyclohexyl)acetate Chemical compound CCOC(=O)CC1CCC(=O)CC1 XHNJFNLTFMAPQB-UHFFFAOYSA-N 0.000 description 1
- RRUJMJLHOSVNCM-UHFFFAOYSA-N ethyl 2-(4-oxocyclohexyl)propanoate Chemical compound CCOC(=O)C(C)C1CCC(=O)CC1 RRUJMJLHOSVNCM-UHFFFAOYSA-N 0.000 description 1
- HDNJCKJLYHRZAO-UHFFFAOYSA-N ethyl 2-(6,7-dichlorodibenzofuran-3-yl)acetate Chemical compound ClC1=CC=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1Cl HDNJCKJLYHRZAO-UHFFFAOYSA-N 0.000 description 1
- UXHRWOAEHFEOLE-UHFFFAOYSA-N ethyl 2-(7,8-dichlorodibenzofuran-3-yl)acetate Chemical compound ClC1=C(Cl)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 UXHRWOAEHFEOLE-UHFFFAOYSA-N 0.000 description 1
- RAPYMLJGZCJFPE-UHFFFAOYSA-N ethyl 2-(8,9-dichlorodibenzofuran-3-yl)acetate Chemical compound C1=C(Cl)C(Cl)=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 RAPYMLJGZCJFPE-UHFFFAOYSA-N 0.000 description 1
- BHTOILRHCJECAF-UHFFFAOYSA-N ethyl 2-(8-aminodibenzofuran-3-yl)propanoate;hydrochloride Chemical compound Cl.C1=C(N)C=C2C3=CC=C(C(C)C(=O)OCC)C=C3OC2=C1 BHTOILRHCJECAF-UHFFFAOYSA-N 0.000 description 1
- UGKUKWDKSIMUJH-UHFFFAOYSA-N ethyl 2-(8-fluorodibenzofuran-3-yl)acetate Chemical compound C1=C(F)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 UGKUKWDKSIMUJH-UHFFFAOYSA-N 0.000 description 1
- PERPMNWAFSGVEW-UHFFFAOYSA-N ethyl 2-(8-fluorodibenzofuran-3-yl)propanoate Chemical compound C1=C(F)C=C2C3=CC=C(C(C)C(=O)OCC)C=C3OC2=C1 PERPMNWAFSGVEW-UHFFFAOYSA-N 0.000 description 1
- YJRIAEHHAHYMGM-UHFFFAOYSA-N ethyl 2-(8-methylsulfanyldibenzofuran-3-yl)acetate Chemical compound C1=C(SC)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 YJRIAEHHAHYMGM-UHFFFAOYSA-N 0.000 description 1
- CCOURXVDCLBFGM-UHFFFAOYSA-N ethyl 2-(8-nitrodibenzofuran-3-yl)acetate Chemical compound C1=C([N+]([O-])=O)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 CCOURXVDCLBFGM-UHFFFAOYSA-N 0.000 description 1
- MMDRZSGQUSGPCC-UHFFFAOYSA-N ethyl 2-(9-chlorodibenzofuran-3-yl)acetate Chemical compound C1=CC(Cl)=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 MMDRZSGQUSGPCC-UHFFFAOYSA-N 0.000 description 1
- NECDXIMDUJJBDS-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenoxy)-4-oxocyclohexyl]acetate Chemical compound C1C(CC(=O)OCC)CCC(=O)C1OC1=CC=C(Cl)C=C1 NECDXIMDUJJBDS-UHFFFAOYSA-N 0.000 description 1
- QRNAFDOHEYYTHE-UHFFFAOYSA-N ethyl 2-[3-(4-fluorophenoxy)-4-oxocyclohexyl]propanoate Chemical compound C1C(C(C)C(=O)OCC)CCC(=O)C1OC1=CC=C(F)C=C1 QRNAFDOHEYYTHE-UHFFFAOYSA-N 0.000 description 1
- MJGSFNIMWQDAHH-UHFFFAOYSA-N ethyl 2-[8-(trifluoromethyl)dibenzofuran-3-yl]acetate Chemical compound C1=C(C(F)(F)F)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 MJGSFNIMWQDAHH-UHFFFAOYSA-N 0.000 description 1
- DNVYSDFFOBRVPB-UHFFFAOYSA-N ethyl 2-dibenzofuran-3-ylpropanoate Chemical compound C1=CC=C2C3=CC=C(C(C)C(=O)OCC)C=C3OC2=C1 DNVYSDFFOBRVPB-UHFFFAOYSA-N 0.000 description 1
- QLWXLDUDIUDSNH-UHFFFAOYSA-N ethyl 3-(3-bromo-4-oxocyclohexyl)propanoate Chemical compound CCOC(=O)CCC1CCC(=O)C(Br)C1 QLWXLDUDIUDSNH-UHFFFAOYSA-N 0.000 description 1
- PAJSZXGYYFGUOQ-UHFFFAOYSA-N ethyl 7-(2-ethoxy-2-oxoethyl)dibenzofuran-2-carboxylate Chemical compound C1=C(C(=O)OCC)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 PAJSZXGYYFGUOQ-UHFFFAOYSA-N 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
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- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- QEGNUYASOUJEHD-UHFFFAOYSA-N gem-dimethylcyclohexane Natural products CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- GEEGRIYRQCBJLM-UHFFFAOYSA-N methyl 2-(8-chlorodibenzofuran-3-yl)acetate Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)OC)C=C3OC2=C1 GEEGRIYRQCBJLM-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- GPQRDVVESTVOCK-UHFFFAOYSA-N n-(4-hydroxyphenyl)acetamide;hydrochloride Chemical compound Cl.CC(=O)NC1=CC=C(O)C=C1 GPQRDVVESTVOCK-UHFFFAOYSA-N 0.000 description 1
- ZBUQPAJRQXISTC-UHFFFAOYSA-N n-(chloromethyl)-n-ethylethanamine Chemical compound CCN(CC)CCl ZBUQPAJRQXISTC-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical class CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 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
- 235000021317 phosphate Nutrition 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- QOGCGSWEVWTHNX-UHFFFAOYSA-M sodium;4-acetamidophenolate Chemical compound [Na+].CC(=O)NC1=CC=C([O-])C=C1 QOGCGSWEVWTHNX-UHFFFAOYSA-M 0.000 description 1
- FENGEGUDMXHOBU-UHFFFAOYSA-M sodium;4-fluorophenolate Chemical compound [Na+].[O-]C1=CC=C(F)C=C1 FENGEGUDMXHOBU-UHFFFAOYSA-M 0.000 description 1
- ZECBPBHBGNLLMU-UHFFFAOYSA-M sodium;4-methylphenolate Chemical compound [Na+].CC1=CC=C([O-])C=C1 ZECBPBHBGNLLMU-UHFFFAOYSA-M 0.000 description 1
- LKYIPGJOXSVWPX-UHFFFAOYSA-M sodium;thiophene-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CS1 LKYIPGJOXSVWPX-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44885374A | 1974-03-07 | 1974-03-07 | |
| US448853 | 1974-03-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50121260A JPS50121260A (en, 2012) | 1975-09-23 |
| JPS5910356B2 true JPS5910356B2 (ja) | 1984-03-08 |
Family
ID=23781916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50026124A Expired JPS5910356B2 (ja) | 1974-03-07 | 1975-03-05 | ベンゾフラン誘導体の製造方法 |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US4022805A (en, 2012) |
| JP (1) | JPS5910356B2 (en, 2012) |
| AR (1) | AR223797A1 (en, 2012) |
| AT (4) | AT353257B (en, 2012) |
| AU (1) | AU500749B2 (en, 2012) |
| BE (1) | BE826345A (en, 2012) |
| BR (1) | BR7501324A (en, 2012) |
| CA (1) | CA1041106A (en, 2012) |
| CH (1) | CH618165A5 (en, 2012) |
| CU (1) | CU34216A (en, 2012) |
| DD (1) | DD118424A5 (en, 2012) |
| DE (1) | DE2510001A1 (en, 2012) |
| DK (1) | DK143133C (en, 2012) |
| ES (1) | ES435341A1 (en, 2012) |
| FI (1) | FI66857C (en, 2012) |
| FR (1) | FR2262979B1 (en, 2012) |
| GB (1) | GB1471847A (en, 2012) |
| HK (1) | HK19680A (en, 2012) |
| IE (1) | IE40760B1 (en, 2012) |
| IL (1) | IL46729A (en, 2012) |
| KE (1) | KE3036A (en, 2012) |
| LU (1) | LU71971A1 (en, 2012) |
| MY (1) | MY8100033A (en, 2012) |
| NL (1) | NL7502477A (en, 2012) |
| NO (1) | NO143664C (en, 2012) |
| PH (1) | PH13826A (en, 2012) |
| SE (1) | SE419646B (en, 2012) |
| YU (2) | YU39465B (en, 2012) |
| ZA (1) | ZA751101B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6115350U (ja) * | 1984-06-28 | 1986-01-29 | 日本鋪道株式会社 | 掘削装置のバケツト装置 |
| JPS645951U (en, 2012) * | 1987-06-26 | 1989-01-13 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102816A (en) * | 1976-10-18 | 1978-07-25 | The United States Of America As Represented By The Secretary Of The Interior | Adsorbent for polynuclear aromatic compounds |
| US4501908A (en) * | 1981-03-12 | 1985-02-26 | Hoffmann-La Roche Inc. | 2,3-Isopropylidene ribonic acid, 1,4-lactones |
| EG17620A (en) * | 1984-11-15 | 1990-10-30 | Wellcome Found | A process for the preparation of polycyclic biocidal compounds their preparation and formulations containing them |
| GB8428930D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
| US5019573A (en) * | 1989-09-19 | 1991-05-28 | Euroceltique, S.A. | Substituted dibenzofurans and methods of using same |
| US7601856B2 (en) | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| US7662831B2 (en) | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH532629A (de) | 1969-12-17 | 1973-01-15 | Ciba Geigy Ag | Verfahren zum optischen Aufhellen mit neuen Bis-aroxazolyl-Verbindungen |
| US3803180A (en) * | 1971-03-26 | 1974-04-09 | L Berger | Tricyclic compounds |
| NL7305520A (en, 2012) * | 1972-05-13 | 1973-11-15 |
-
1975
- 1975-02-10 US US05/548,658 patent/US4022805A/en not_active Expired - Lifetime
- 1975-02-17 CH CH195675A patent/CH618165A5/de not_active IP Right Cessation
- 1975-02-21 ZA ZA00751101A patent/ZA751101B/xx unknown
- 1975-02-28 IL IL46729A patent/IL46729A/xx unknown
- 1975-02-28 CA CA220,990A patent/CA1041106A/en not_active Expired
- 1975-03-01 CU CU34216A patent/CU34216A/es unknown
- 1975-03-03 PH PH16854A patent/PH13826A/en unknown
- 1975-03-03 YU YU499/75A patent/YU39465B/xx unknown
- 1975-03-03 AU AU78737/75A patent/AU500749B2/en not_active Expired
- 1975-03-03 NL NL7502477A patent/NL7502477A/xx not_active Application Discontinuation
- 1975-03-05 DD DD184587A patent/DD118424A5/xx unknown
- 1975-03-05 LU LU71971A patent/LU71971A1/xx unknown
- 1975-03-05 SE SE7502468A patent/SE419646B/xx unknown
- 1975-03-05 JP JP50026124A patent/JPS5910356B2/ja not_active Expired
- 1975-03-05 FR FR7506848A patent/FR2262979B1/fr not_active Expired
- 1975-03-06 IE IE490/75A patent/IE40760B1/xx unknown
- 1975-03-06 BR BR1324/75A patent/BR7501324A/pt unknown
- 1975-03-06 FI FI750646A patent/FI66857C/fi not_active IP Right Cessation
- 1975-03-06 ES ES435341A patent/ES435341A1/es not_active Expired
- 1975-03-06 AR AR257869A patent/AR223797A1/es active
- 1975-03-06 BE BE154047A patent/BE826345A/xx not_active IP Right Cessation
- 1975-03-06 GB GB938075A patent/GB1471847A/en not_active Expired
- 1975-03-06 DK DK91375A patent/DK143133C/da not_active IP Right Cessation
- 1975-03-06 NO NO750746A patent/NO143664C/no unknown
- 1975-03-06 AT AT173175A patent/AT353257B/de not_active IP Right Cessation
- 1975-03-07 DE DE19752510001 patent/DE2510001A1/de not_active Ceased
-
1978
- 1978-04-07 US US05/894,282 patent/US4192809A/en not_active Expired - Lifetime
- 1978-07-14 AT AT513478A patent/AT356099B/de not_active IP Right Cessation
- 1978-07-14 AT AT513278A patent/AT356097B/de not_active IP Right Cessation
- 1978-07-14 AT AT513378A patent/AT356098B/de not_active IP Right Cessation
-
1980
- 1980-03-19 KE KE3036A patent/KE3036A/xx unknown
- 1980-04-10 HK HK196/80A patent/HK19680A/xx unknown
-
1981
- 1981-04-10 YU YU00934/81A patent/YU93481A/xx unknown
- 1981-12-30 MY MY33/81A patent/MY8100033A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6115350U (ja) * | 1984-06-28 | 1986-01-29 | 日本鋪道株式会社 | 掘削装置のバケツト装置 |
| JPS645951U (en, 2012) * | 1987-06-26 | 1989-01-13 |
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