SU610488A3 - Способ получени -фенилпирролов - Google Patents
Способ получени -фенилпирроловInfo
- Publication number
- SU610488A3 SU610488A3 SU742005407A SU2005407A SU610488A3 SU 610488 A3 SU610488 A3 SU 610488A3 SU 742005407 A SU742005407 A SU 742005407A SU 2005407 A SU2005407 A SU 2005407A SU 610488 A3 SU610488 A3 SU 610488A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- square
- acetic acid
- mixture
- found
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 135
- 229960000583 acetic acid Drugs 0.000 description 57
- 239000013078 crystal Substances 0.000 description 50
- 239000000203 mixture Substances 0.000 description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 239000012362 glacial acetic acid Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 238000010992 reflux Methods 0.000 description 33
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 27
- 229960004963 mesalazine Drugs 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 26
- -1 3-Carboxyphenyl Chemical group 0.000 description 22
- 239000007787 solid Substances 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 15
- 239000010410 layer Substances 0.000 description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- AIZCLPNQLZSCJC-UHFFFAOYSA-N 2-phenacylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)CC1CCCCC1=O AIZCLPNQLZSCJC-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- KTZNVZJECQAMBV-UHFFFAOYSA-N 1-(cyclohexen-1-yl)pyrrolidine Chemical compound C1CCCN1C1=CCCCC1 KTZNVZJECQAMBV-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ITTLQABJFKKHGL-UHFFFAOYSA-N 2-phenacyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC2=CC=CC=C2C(=O)C1CC(=O)C1=CC=CC=C1 ITTLQABJFKKHGL-UHFFFAOYSA-N 0.000 description 3
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- YWYAUYAEQBYZFN-UHFFFAOYSA-N 1-(3,4-dihydronaphthalen-2-yl)pyrrolidine Chemical compound C1CCCN1C1=CC2=CC=CC=C2CC1 YWYAUYAEQBYZFN-UHFFFAOYSA-N 0.000 description 2
- CTMLFTIHVVMDFE-UHFFFAOYSA-N 1-phenacyl-3,4-dihydro-1h-naphthalen-2-one Chemical compound O=C1CCC2=CC=CC=C2C1CC(=O)C1=CC=CC=C1 CTMLFTIHVVMDFE-UHFFFAOYSA-N 0.000 description 2
- KLLBUCLQUIDHHR-UHFFFAOYSA-N 2-(2-oxo-2-thiophen-2-ylethyl)cyclohexan-1-one Chemical compound C=1C=CSC=1C(=O)CC1CCCCC1=O KLLBUCLQUIDHHR-UHFFFAOYSA-N 0.000 description 2
- NKZGJVACPAIVTC-UHFFFAOYSA-N 2-[2-(4-methylphenyl)-2-oxoethyl]cyclohexan-1-one Chemical compound C1=CC(C)=CC=C1C(=O)CC1C(=O)CCCC1 NKZGJVACPAIVTC-UHFFFAOYSA-N 0.000 description 2
- RYFPHAYLPBOGTC-UHFFFAOYSA-N 2-phenacylcycloheptan-1-one Chemical compound C=1C=CC=CC=1C(=O)CC1CCCCCC1=O RYFPHAYLPBOGTC-UHFFFAOYSA-N 0.000 description 2
- ROUKPIDVWDJREO-UHFFFAOYSA-N 2-phenacylcyclopentan-1-one Chemical compound C=1C=CC=CC=1C(=O)CC1CCCC1=O ROUKPIDVWDJREO-UHFFFAOYSA-N 0.000 description 2
- ZRDVVGOZRIEJED-UHFFFAOYSA-N 3-acetamido-5-amino-2-hydroxybenzoic acid Chemical compound CC(=O)NC1=CC(N)=CC(C(O)=O)=C1O ZRDVVGOZRIEJED-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- GSHDVBCFBNMLOW-UHFFFAOYSA-N 4-methoxy-2-phenacylcyclohexan-1-one Chemical compound C1C(OC)CCC(=O)C1CC(=O)C1=CC=CC=C1 GSHDVBCFBNMLOW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 229960003887 dichlorophen Drugs 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- UZNQNWYIDSYPLV-UHFFFAOYSA-N 1-(1h-inden-2-yl)pyrrolidine Chemical compound C1CCCN1C1=CC2=CC=CC=C2C1 UZNQNWYIDSYPLV-UHFFFAOYSA-N 0.000 description 1
- IKZFNBPDKHJAJE-UHFFFAOYSA-N 1-(4-methoxycyclohexen-1-yl)pyrrolidine Chemical compound C1C(OC)CCC(N2CCCC2)=C1 IKZFNBPDKHJAJE-UHFFFAOYSA-N 0.000 description 1
- YABVEIMEMIADEE-UHFFFAOYSA-N 1-(4-methylcyclohexen-1-yl)pyrrolidine Chemical compound C1C(C)CCC(N2CCCC2)=C1 YABVEIMEMIADEE-UHFFFAOYSA-N 0.000 description 1
- XFZOWALKXPPPDD-UHFFFAOYSA-N 1-(6-chloro-3,4-dihydronaphthalen-2-yl)pyrrolidine Chemical compound C1CC2=CC(Cl)=CC=C2C=C1N1CCCC1 XFZOWALKXPPPDD-UHFFFAOYSA-N 0.000 description 1
- XBWKFFYXUHIZLX-UHFFFAOYSA-N 1-(7-chloro-1,2-dihydronaphthalen-2-yl)pyrrolidine Chemical compound ClC=1C=C2CC(C=CC2=CC1)N1CCCC1 XBWKFFYXUHIZLX-UHFFFAOYSA-N 0.000 description 1
- UETVMGUBKRBHAV-UHFFFAOYSA-N 1-(cyclohepten-1-yl)pyrrolidine Chemical compound C1CCCN1C1=CCCCCC1 UETVMGUBKRBHAV-UHFFFAOYSA-N 0.000 description 1
- GEZGAZKEOUKLBR-UHFFFAOYSA-N 1-phenylpyrrole Chemical class C1=CC=CN1C1=CC=CC=C1 GEZGAZKEOUKLBR-UHFFFAOYSA-N 0.000 description 1
- RBQAWPVPHCHEHE-UHFFFAOYSA-N 2-(2-methoxyphenyl)cyclohexan-1-one Chemical compound COC1=CC=CC=C1C1C(=O)CCCC1 RBQAWPVPHCHEHE-UHFFFAOYSA-N 0.000 description 1
- VIAQPVWZRPNNLT-UHFFFAOYSA-N 2-[2-(2-methoxyphenyl)-2-oxoethyl]cyclohexan-1-one Chemical compound COC1=CC=CC=C1C(=O)CC1C(=O)CCCC1 VIAQPVWZRPNNLT-UHFFFAOYSA-N 0.000 description 1
- FTNRXOWXEWCIGV-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-2-oxoethyl]cyclohexan-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)CC1C(=O)CCCC1 FTNRXOWXEWCIGV-UHFFFAOYSA-N 0.000 description 1
- CHNJASARQCDREF-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-2-oxoethyl]cyclohexan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CC1C(=O)CCCC1 CHNJASARQCDREF-UHFFFAOYSA-N 0.000 description 1
- HWZNLXNSUQETKX-UHFFFAOYSA-N 2-[2-oxo-2-(4-phenylphenyl)ethyl]cyclohexan-1-one Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)CC1CCCCC1=O HWZNLXNSUQETKX-UHFFFAOYSA-N 0.000 description 1
- BYLKHCBYQSZXNC-UHFFFAOYSA-N 2-[2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl]cyclohexan-1-one Chemical compound FC(F)(F)C1=CC=CC(C(=O)CC2C(CCCC2)=O)=C1 BYLKHCBYQSZXNC-UHFFFAOYSA-N 0.000 description 1
- VDXWQJAVUORTLG-UHFFFAOYSA-N 2-acetamido-5-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound C1=C(C(O)=O)C(NC(=O)C)=CC=C1N1C(C=2C=CC=CC=2)=CC2=C1CCCC2 VDXWQJAVUORTLG-UHFFFAOYSA-N 0.000 description 1
- VENSKZQVHFCKNZ-UHFFFAOYSA-N 2-acetamido-5-aminobenzoic acid Chemical compound CC(=O)NC1=CC=C(N)C=C1C(O)=O VENSKZQVHFCKNZ-UHFFFAOYSA-N 0.000 description 1
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 1
- MBUPVGIGAMCMBT-UHFFFAOYSA-N 2-bromo-1-(4-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=C(C(=O)CBr)C=C1 MBUPVGIGAMCMBT-UHFFFAOYSA-N 0.000 description 1
- KGHGZRVXCKCJGX-UHFFFAOYSA-N 2-bromo-1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)CBr)=CC=C1C1=CC=CC=C1 KGHGZRVXCKCJGX-UHFFFAOYSA-N 0.000 description 1
- TZIYNLSEBAYCBZ-UHFFFAOYSA-N 2-bromo-1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)CBr)=C1 TZIYNLSEBAYCBZ-UHFFFAOYSA-N 0.000 description 1
- AGWGHNGJJCOWQV-UHFFFAOYSA-N 2-chloro-5-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(N2C(=CC=3CCCCC=32)C=2C=CC=CC=2)=C1 AGWGHNGJJCOWQV-UHFFFAOYSA-N 0.000 description 1
- NCRHSRBOWZYFOW-UHFFFAOYSA-N 2-hydroxy-5-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N2C(=CC=3CCCCC=32)C=2C=CC=CC=2)=C1 NCRHSRBOWZYFOW-UHFFFAOYSA-N 0.000 description 1
- BWLOCUXCFWSOHO-UHFFFAOYSA-N 2-hydroxy-5-(2-thiophen-2-yl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N2C(=CC=3CCCCC=32)C=2SC=CC=2)=C1 BWLOCUXCFWSOHO-UHFFFAOYSA-N 0.000 description 1
- LSISLFZIWWTXOY-UHFFFAOYSA-N 2-hydroxy-5-(5-methyl-2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound C1C(C)CCC(N2C=3C=C(C(O)=CC=3)C(O)=O)=C1C=C2C1=CC=CC=C1 LSISLFZIWWTXOY-UHFFFAOYSA-N 0.000 description 1
- CTAZOTBVBIWDAP-UHFFFAOYSA-N 2-hydroxy-5-[2-(2-methoxyphenyl)-4,5,6,7-tetrahydroindol-1-yl]benzoic acid Chemical compound COC1=CC=CC=C1C(N1C=2C=C(C(O)=CC=2)C(O)=O)=CC2=C1CCCC2 CTAZOTBVBIWDAP-UHFFFAOYSA-N 0.000 description 1
- DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 description 1
- UKBQGDXFASMLHR-UHFFFAOYSA-N 3-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(N2C(=CC=3CCCCC=32)C=2C=CC=CC=2)=C1 UKBQGDXFASMLHR-UHFFFAOYSA-N 0.000 description 1
- ZHRKUEXROQMRLL-UHFFFAOYSA-N 3-[2-(4-bromophenyl)-4,5,6,7-tetrahydroindol-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(N2C(=CC=3CCCCC=32)C=2C=CC(Br)=CC=2)=C1 ZHRKUEXROQMRLL-UHFFFAOYSA-N 0.000 description 1
- VAVYZVSAHSZDPX-UHFFFAOYSA-N 3-acetamido-2-hydroxy-5-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound OC(=O)C1=C(O)C(NC(=O)C)=CC(N2C(=CC=3CCCCC=32)C=2C=CC=CC=2)=C1 VAVYZVSAHSZDPX-UHFFFAOYSA-N 0.000 description 1
- HJICEQGYRAZIEH-UHFFFAOYSA-N 3-acetamido-2-hydroxy-5-nitrobenzoic acid Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=CC(C(O)=O)=C1O HJICEQGYRAZIEH-UHFFFAOYSA-N 0.000 description 1
- CHPWMILLLGUBMA-UHFFFAOYSA-N 3-bromo-2-hydroxy-5-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound BrC1=C(O)C(C(=O)O)=CC(N2C(=CC=3CCCCC=32)C=2C=CC=CC=2)=C1 CHPWMILLLGUBMA-UHFFFAOYSA-N 0.000 description 1
- LJXLDKNBUBLQPF-UHFFFAOYSA-N 3-chloro-2-hydroxy-5-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound ClC1=C(O)C(C(=O)O)=CC(N2C(=CC=3CCCCC=32)C=2C=CC=CC=2)=C1 LJXLDKNBUBLQPF-UHFFFAOYSA-N 0.000 description 1
- KPXKGZSDHYHPFB-UHFFFAOYSA-N 4-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(C=2C=CC=CC=2)=CC2=C1CCCC2 KPXKGZSDHYHPFB-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- JQFIFBVEYMQOFY-UHFFFAOYSA-N 4-methyl-2-phenacylcyclohexan-1-one Chemical compound C1C(C)CCC(=O)C1CC(=O)C1=CC=CC=C1 JQFIFBVEYMQOFY-UHFFFAOYSA-N 0.000 description 1
- OPWJLYPXLLWOHU-UHFFFAOYSA-N 4-tert-butyl-2-phenacylcyclohexan-1-one Chemical compound C1C(C(C)(C)C)CCC(=O)C1CC(=O)C1=CC=CC=C1 OPWJLYPXLLWOHU-UHFFFAOYSA-N 0.000 description 1
- PJTMQLHFQYFBBB-UHFFFAOYSA-N 4-tert-butylcyclohexene Chemical compound CC(C)(C)C1CCC=CC1 PJTMQLHFQYFBBB-UHFFFAOYSA-N 0.000 description 1
- JVASPSRVYWCHNR-UHFFFAOYSA-N 5-(2,3-diphenyl-4,5,6,7-tetrahydroindol-1-yl)-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N2C(=C(C=3CCCCC=32)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 JVASPSRVYWCHNR-UHFFFAOYSA-N 0.000 description 1
- OZQKJEXMVUFKLB-UHFFFAOYSA-N 5-(5-tert-butyl-2-phenyl-4,5,6,7-tetrahydroindol-1-yl)-2-hydroxybenzoic acid Chemical compound C1C(C(C)(C)C)CCC(N2C=3C=C(C(O)=CC=3)C(O)=O)=C1C=C2C1=CC=CC=C1 OZQKJEXMVUFKLB-UHFFFAOYSA-N 0.000 description 1
- CXFFFBOEDVCDJG-UHFFFAOYSA-N 5-[2-(3,4-dichlorophenyl)-4,5,6,7-tetrahydroindol-1-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N2C(=CC=3CCCCC=32)C=2C=C(Cl)C(Cl)=CC=2)=C1 CXFFFBOEDVCDJG-UHFFFAOYSA-N 0.000 description 1
- PCKQZZPQKJJREL-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)-4,5,6,7-tetrahydroindol-1-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N2C(=CC=3CCCCC=32)C=2C=CC(F)=CC=2)=C1 PCKQZZPQKJJREL-UHFFFAOYSA-N 0.000 description 1
- GVCFFVPEOLCYNN-UHFFFAOYSA-N 5-amino-2-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C(C(O)=O)=C1 GVCFFVPEOLCYNN-UHFFFAOYSA-N 0.000 description 1
- UHPSFLZKUVRFDO-UHFFFAOYSA-N 5-amino-2-hydroxy-4-(trifluoromethyl)benzoic acid Chemical compound NC1=CC(C(O)=O)=C(O)C=C1C(F)(F)F UHPSFLZKUVRFDO-UHFFFAOYSA-N 0.000 description 1
- SGAMDQAWRICYND-UHFFFAOYSA-N 5-amino-3-chloro-2-hydroxybenzoic acid Chemical compound NC1=CC(Cl)=C(O)C(C(O)=O)=C1 SGAMDQAWRICYND-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 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 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- PFYFHXLWUJNWSP-UHFFFAOYSA-N methyl 2-(2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoate Chemical compound COC(=O)C1=CC=CC=C1N1C(C=2C=CC=CC=2)=CC2=C1CCCC2 PFYFHXLWUJNWSP-UHFFFAOYSA-N 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Pyrrole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US336919A US3878225A (en) | 1973-03-01 | 1973-03-01 | Condensed pyrroles bearing an N-phenyl substituent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU610488A3 true SU610488A3 (ru) | 1978-06-05 |
Family
ID=23318274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU742005407A SU610488A3 (ru) | 1973-03-01 | 1974-02-28 | Способ получени -фенилпирролов |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3878225A (OSRAM) |
| JP (1) | JPS6139304B2 (OSRAM) |
| AT (1) | AT332389B (OSRAM) |
| BE (1) | BE811785A (OSRAM) |
| CA (1) | CA1025455A (OSRAM) |
| CH (1) | CH611605A5 (OSRAM) |
| CS (1) | CS191225B2 (OSRAM) |
| DE (1) | DE2407671C2 (OSRAM) |
| ES (2) | ES423562A1 (OSRAM) |
| FI (1) | FI61183C (OSRAM) |
| FR (1) | FR2219790B1 (OSRAM) |
| GB (1) | GB1457601A (OSRAM) |
| HU (1) | HU170834B (OSRAM) |
| IE (1) | IE38943B1 (OSRAM) |
| IL (1) | IL44279A (OSRAM) |
| NL (1) | NL177828C (OSRAM) |
| NO (1) | NO142346C (OSRAM) |
| SE (1) | SE397523B (OSRAM) |
| SU (1) | SU610488A3 (OSRAM) |
| ZA (1) | ZA741333B (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4056624A (en) * | 1976-05-14 | 1977-11-01 | American Hoechst Corporation | Method of treating dermal inflammation |
| US5145965A (en) * | 1987-09-24 | 1992-09-08 | Hoechst-Roussel Pharmaceuticals Incorporated | 2,6-methanopyrrolo-3-benzazocines |
| US4929622A (en) * | 1987-09-24 | 1990-05-29 | Hoechst-Roussel Pharmaceuticals, Inc. | 2,6-Methanopyrrolo-3-benzazocines |
| US4814501A (en) * | 1987-12-28 | 1989-03-21 | Merck & Co., Inc. | Process for preparing N,N-dimethyl 2-(methylthio) benzamides and analogs |
| US9216966B2 (en) | 2004-10-04 | 2015-12-22 | John Manfredi | Compounds for Alzheimer's disease |
| US7678823B2 (en) * | 2004-10-04 | 2010-03-16 | Myriad Pharmaceticals, Inc. | Compounds for alzheimer's disease |
| KR20070060156A (ko) * | 2004-10-04 | 2007-06-12 | 미리어드 제네틱스, 인크. | 알츠하이머병 치료용 화합물 |
| JP2009532501A (ja) * | 2006-04-04 | 2009-09-10 | ミリアド ジェネティクス， インコーポレイテッド | 疾患および障害のための化合物 |
| CA2694216A1 (en) * | 2007-07-24 | 2009-01-29 | Astellas Pharma Inc. | Benzimidazole derivative |
| US8367665B2 (en) | 2008-04-16 | 2013-02-05 | Karo Bio Ab | Estrogen receptor ligands |
| GB201113538D0 (en) | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70880A (OSRAM) * | ||||
| US3687971A (en) * | 1970-06-22 | 1972-08-29 | Merck & Co Inc | 4-(pyrrolyl)-salicylic acid derivatives |
| GB1351754A (en) * | 1970-07-02 | 1974-05-01 | Allen & Hanburys Ltd | Indenopyrrole derivatives |
-
1973
- 1973-03-01 US US336919A patent/US3878225A/en not_active Expired - Lifetime
-
1974
- 1974-02-18 DE DE2407671A patent/DE2407671C2/de not_active Expired
- 1974-02-22 NL NLAANVRAGE7402465,A patent/NL177828C/xx not_active IP Right Cessation
- 1974-02-23 ES ES423562A patent/ES423562A1/es not_active Expired
- 1974-02-25 IL IL44279A patent/IL44279A/en unknown
- 1974-02-26 CH CH271174A patent/CH611605A5/xx not_active IP Right Cessation
- 1974-02-26 CS CS741407A patent/CS191225B2/cs unknown
- 1974-02-27 FI FI580/74A patent/FI61183C/fi active
- 1974-02-28 SE SE7402667A patent/SE397523B/xx not_active IP Right Cessation
- 1974-02-28 HU HUHO001652 patent/HU170834B/hu not_active IP Right Cessation
- 1974-02-28 IE IE00422/74A patent/IE38943B1/xx unknown
- 1974-02-28 CA CA193,763A patent/CA1025455A/en not_active Expired
- 1974-02-28 SU SU742005407A patent/SU610488A3/ru active
- 1974-02-28 ZA ZA00741333A patent/ZA741333B/xx unknown
- 1974-02-28 AT AT165474A patent/AT332389B/de not_active IP Right Cessation
- 1974-02-28 NO NO740694A patent/NO142346C/no unknown
- 1974-03-01 FR FR7407146A patent/FR2219790B1/fr not_active Expired
- 1974-03-01 JP JP49023476A patent/JPS6139304B2/ja not_active Expired
- 1974-03-01 GB GB946774A patent/GB1457601A/en not_active Expired
- 1974-03-01 BE BE141569A patent/BE811785A/xx not_active IP Right Cessation
-
1975
- 1975-04-30 ES ES437259A patent/ES437259A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES437259A1 (es) | 1977-01-01 |
| NO142346B (no) | 1980-04-28 |
| NL177828C (nl) | 1985-12-02 |
| FR2219790B1 (OSRAM) | 1978-09-22 |
| IL44279A (en) | 1977-10-31 |
| IL44279A0 (en) | 1974-05-16 |
| NO142346C (no) | 1980-08-06 |
| NO740694L (no) | 1974-09-03 |
| ATA165474A (de) | 1976-01-15 |
| HU170834B (hu) | 1977-09-28 |
| IE38943L (en) | 1974-09-01 |
| CS191225B2 (en) | 1979-06-29 |
| DE2407671C2 (de) | 1983-12-01 |
| JPS6139304B2 (OSRAM) | 1986-09-03 |
| ES423562A1 (es) | 1976-06-01 |
| JPS49134671A (OSRAM) | 1974-12-25 |
| CA1025455A (en) | 1978-01-31 |
| ZA741333B (en) | 1975-02-26 |
| FI61183B (fi) | 1982-02-26 |
| AU6618874A (en) | 1975-09-04 |
| CH611605A5 (OSRAM) | 1979-06-15 |
| SE397523B (sv) | 1977-11-07 |
| NL177828B (nl) | 1985-07-01 |
| DE2407671A1 (de) | 1974-09-12 |
| AT332389B (de) | 1976-09-27 |
| NL7402465A (OSRAM) | 1974-09-03 |
| FI61183C (fi) | 1982-06-10 |
| US3878225A (en) | 1975-04-15 |
| GB1457601A (en) | 1976-12-08 |
| IE38943B1 (en) | 1978-07-05 |
| BE811785A (fr) | 1974-09-02 |
| FR2219790A1 (OSRAM) | 1974-09-27 |
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