NO300539B1 - alfa,omega-diarylalkanderivater, med terapeutisk aktivitet for behandling og forhindring av sirkulasjonssykdommer og psykoser, og farmasöytiske preparater inneholdende disse derivater - Google Patents
alfa,omega-diarylalkanderivater, med terapeutisk aktivitet for behandling og forhindring av sirkulasjonssykdommer og psykoser, og farmasöytiske preparater inneholdende disse derivater Download PDFInfo
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- NO300539B1 NO300539B1 NO934311A NO934311A NO300539B1 NO 300539 B1 NO300539 B1 NO 300539B1 NO 934311 A NO934311 A NO 934311A NO 934311 A NO934311 A NO 934311A NO 300539 B1 NO300539 B1 NO 300539B1
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- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- 238000011282 treatment Methods 0.000 title description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 7
- 230000002265 prevention Effects 0.000 title description 4
- 208000028017 Psychotic disease Diseases 0.000 title description 3
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 208000035475 disorder Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 351
- -1 cyano, carbamoyl Chemical group 0.000 claims description 333
- 125000004432 carbon atom Chemical group C* 0.000 claims description 162
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
- 125000000623 heterocyclic group Chemical group 0.000 claims description 64
- 125000002947 alkylene group Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 35
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 34
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000004423 acyloxy group Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 150000001721 carbon Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 21
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 18
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
- 125000005936 piperidyl group Chemical group 0.000 claims description 17
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 13
- 125000001589 carboacyl group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 5
- HWUPBKARLUGYRA-UHFFFAOYSA-N 1-(dimethylamino)-3-[2-(4-phenylbutyl)phenoxy]propan-2-ol Chemical compound CN(C)CC(O)COC1=CC=CC=C1CCCCC1=CC=CC=C1 HWUPBKARLUGYRA-UHFFFAOYSA-N 0.000 claims description 4
- DVSPFNFDMLLSTI-UHFFFAOYSA-N 2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidine Chemical compound COC1=CC=CC(CCC=2C(=CC=CC=2)OCCC2N(CCC2)C)=C1 DVSPFNFDMLLSTI-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- XKWHRQZAYHUMME-UHFFFAOYSA-N 1-methyl-2-[2-[2-(2-phenylethyl)phenoxy]ethyl]pyrrolidine Chemical compound CN1CCCC1CCOC1=CC=CC=C1CCC1=CC=CC=C1 XKWHRQZAYHUMME-UHFFFAOYSA-N 0.000 claims description 3
- PVZYBMFBXZDABU-UHFFFAOYSA-N 1-methyl-2-[2-[2-(4-phenylbutyl)phenoxy]ethyl]pyrrolidine Chemical compound CN1CCCC1CCOC1=CC=CC=C1CCCCC1=CC=CC=C1 PVZYBMFBXZDABU-UHFFFAOYSA-N 0.000 claims description 3
- KGESEPMIYHUEPA-UHFFFAOYSA-N 1-methyl-2-[2-[2-(5-phenylpentyl)phenoxy]ethyl]pyrrolidine Chemical compound CN1CCCC1CCOC1=CC=CC=C1CCCCCC1=CC=CC=C1 KGESEPMIYHUEPA-UHFFFAOYSA-N 0.000 claims description 3
- OMPUPABAYLNHHM-UHFFFAOYSA-N 2-[2-[2-[2-(3,5-dimethoxyphenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidine Chemical compound COC1=CC(OC)=CC(CCC=2C(=CC=CC=2)OCCC2N(CCC2)C)=C1 OMPUPABAYLNHHM-UHFFFAOYSA-N 0.000 claims description 3
- RSECLZHMVXGSLB-UHFFFAOYSA-N 2-[2-[2-[2-(3-fluorophenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC1=CC=CC=C1CCC1=CC=CC(F)=C1 RSECLZHMVXGSLB-UHFFFAOYSA-N 0.000 claims description 3
- OFOAASLLLQMYIG-UHFFFAOYSA-N 2-[2-[2-[4-(2-methoxyphenyl)butyl]phenoxy]ethyl]-1-methylpyrrolidine Chemical compound COC1=CC=CC=C1CCCCC1=CC=CC=C1OCCC1N(C)CCC1 OFOAASLLLQMYIG-UHFFFAOYSA-N 0.000 claims description 3
- SJVIFPZFZMWHOH-UHFFFAOYSA-N 2-[2-[2-[4-(3,5-dimethoxyphenyl)butyl]phenoxy]ethyl]-1-methylpyrrolidine Chemical compound COC1=CC(OC)=CC(CCCCC=2C(=CC=CC=2)OCCC2N(CCC2)C)=C1 SJVIFPZFZMWHOH-UHFFFAOYSA-N 0.000 claims description 3
- NZBUENLGURCFJE-UHFFFAOYSA-N 2-[2-[2-[4-(3-methoxyphenyl)butyl]phenoxy]ethyl]-1-methylpyrrolidine Chemical compound COC1=CC=CC(CCCCC=2C(=CC=CC=2)OCCC2N(CCC2)C)=C1 NZBUENLGURCFJE-UHFFFAOYSA-N 0.000 claims description 3
- GUGISUHYAPDUKN-UHFFFAOYSA-N 3-[2-[4-(2-methoxyphenyl)butyl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound COC1=CC=CC=C1CCCCC1=CC=CC=C1OCCCN(C)C GUGISUHYAPDUKN-UHFFFAOYSA-N 0.000 claims description 3
- DDCPTIIHXFXLML-UHFFFAOYSA-N n,n-dimethyl-3-[2-(4-phenylbutyl)phenoxy]propan-1-amine Chemical compound CN(C)CCCOC1=CC=CC=C1CCCCC1=CC=CC=C1 DDCPTIIHXFXLML-UHFFFAOYSA-N 0.000 claims description 3
- ODSKXGKYTJWPFP-UHFFFAOYSA-N 2-[2-[2-[2-(3-bromophenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC1=CC=CC=C1CCC1=CC=CC(Br)=C1 ODSKXGKYTJWPFP-UHFFFAOYSA-N 0.000 claims description 2
- IDYPKDTVKYPRRD-UHFFFAOYSA-N 2-[2-[2-[2-[3-(difluoromethoxy)phenyl]ethyl]phenoxy]ethyl]-1-methylpyrrolidine Chemical compound CN1CCCC1CCOC1=CC=CC=C1CCC1=CC=CC(OC(F)F)=C1 IDYPKDTVKYPRRD-UHFFFAOYSA-N 0.000 claims description 2
- ICWZIDNZDSTFML-UHFFFAOYSA-N 3-[2-[4-(3-methoxyphenyl)butyl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound COC1=CC=CC(CCCCC=2C(=CC=CC=2)OCCCN(C)C)=C1 ICWZIDNZDSTFML-UHFFFAOYSA-N 0.000 claims description 2
- JJQDLSUQSUYRFQ-UHFFFAOYSA-N 5-[2-[2-[2-(3,5-dimethoxyphenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidin-3-ol Chemical compound COC1=CC(OC)=CC(CCC=2C(=CC=CC=2)OCCC2N(CC(O)C2)C)=C1 JJQDLSUQSUYRFQ-UHFFFAOYSA-N 0.000 claims description 2
- AFZLABYDOCWQBQ-UHFFFAOYSA-N 5-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-1-methylpyrrolidin-3-ol Chemical compound COC1=CC=CC(CCC=2C(=CC=CC=2)OCCC2N(CC(O)C2)C)=C1 AFZLABYDOCWQBQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000027455 binding Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical class 0.000 claims description 2
- 150000002780 morpholines Chemical class 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000003386 piperidinyl group Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000003235 pyrrolidines Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 561
- 239000000243 solution Substances 0.000 description 312
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 270
- 239000000203 mixture Substances 0.000 description 265
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 239
- 238000006243 chemical reaction Methods 0.000 description 217
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 154
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 152
- 238000000034 method Methods 0.000 description 149
- 239000013078 crystal Substances 0.000 description 141
- 239000012230 colorless oil Substances 0.000 description 127
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 120
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 112
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 104
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 104
- 239000002904 solvent Substances 0.000 description 103
- 238000004821 distillation Methods 0.000 description 92
- 239000003480 eluent Substances 0.000 description 90
- 238000002360 preparation method Methods 0.000 description 88
- 238000002844 melting Methods 0.000 description 87
- 230000008018 melting Effects 0.000 description 87
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 86
- 238000004440 column chromatography Methods 0.000 description 85
- 239000000741 silica gel Substances 0.000 description 82
- 229910002027 silica gel Inorganic materials 0.000 description 82
- 238000001914 filtration Methods 0.000 description 79
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 66
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 56
- 239000003153 chemical reaction reagent Substances 0.000 description 50
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 48
- 239000003921 oil Substances 0.000 description 43
- 239000011541 reaction mixture Substances 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 229960004592 isopropanol Drugs 0.000 description 41
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 40
- 238000000862 absorption spectrum Methods 0.000 description 40
- 238000001704 evaporation Methods 0.000 description 40
- 230000008020 evaporation Effects 0.000 description 40
- 239000000047 product Substances 0.000 description 38
- 239000012043 crude product Substances 0.000 description 35
- 125000006239 protecting group Chemical group 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 28
- KCQMALZNENFGKK-UHFFFAOYSA-N 2-(2-chloroethyl)-1-methylpyrrolidine;hydron;chloride Chemical compound Cl.CN1CCCC1CCCl KCQMALZNENFGKK-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000001816 cooling Methods 0.000 description 21
- 239000012280 lithium aluminium hydride Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 17
- 239000012141 concentrate Substances 0.000 description 16
- 235000008504 concentrate Nutrition 0.000 description 16
- 238000003379 elimination reaction Methods 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 150000002170 ethers Chemical class 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 14
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 14
- 230000008030 elimination Effects 0.000 description 14
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 14
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 14
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 14
- 231100000989 no adverse effect Toxicity 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- HGQQRAXOBYWKDV-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)ethyl]phenol Chemical compound COC1=CC=CC(CCC=2C(=CC=CC=2)O)=C1 HGQQRAXOBYWKDV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 11
- 108091005479 5-HT2 receptors Proteins 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 150000008282 halocarbons Chemical class 0.000 description 9
- WILMLDWJNLMPLQ-UHFFFAOYSA-N 2-(4-phenylbutyl)phenol Chemical compound OC1=CC=CC=C1CCCCC1=CC=CC=C1 WILMLDWJNLMPLQ-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 8
- 229920005654 Sephadex Polymers 0.000 description 8
- 239000012507 Sephadex™ Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 8
- 239000002198 insoluble material Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical compound OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 6
- 150000008041 alkali metal carbonates Chemical class 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 6
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- CXMSDJFEGJITND-NRFANRHFSA-N tert-butyl (2s)-2-[[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl]pyrrolidine-1-carboxylate Chemical compound COC1=CC=CC(CCC=2C(=CC=CC=2)OC[C@H]2N(CCC2)C(=O)OC(C)(C)C)=C1 CXMSDJFEGJITND-NRFANRHFSA-N 0.000 description 1
- RPUGIDCRPYGDEJ-QFIPXVFZSA-N tert-butyl (2s)-2-[[2-[2-[3-(methoxymethoxy)phenyl]ethyl]phenoxy]methyl]pyrrolidine-1-carboxylate Chemical compound COCOC1=CC=CC(CCC=2C(=CC=CC=2)OC[C@H]2N(CCC2)C(=O)OC(C)(C)C)=C1 RPUGIDCRPYGDEJ-QFIPXVFZSA-N 0.000 description 1
- IHZXWDNABCXGRA-PLYLYKGUSA-N tert-butyl (4r)-2-[[2-(2-phenylethyl)phenoxy]methyl]-4-phenylmethoxypyrrolidine-1-carboxylate Chemical compound C([C@H](CN1C(=O)OC(C)(C)C)OCC=2C=CC=CC=2)C1COC1=CC=CC=C1CCC1=CC=CC=C1 IHZXWDNABCXGRA-PLYLYKGUSA-N 0.000 description 1
- VDBNMFXOHYQYIQ-BDCODIICSA-N tert-butyl (4r)-2-[[2-(4-phenylbutyl)phenoxy]methyl]-4-phenylmethoxypyrrolidine-1-carboxylate Chemical compound C([C@H](CN1C(=O)OC(C)(C)C)OCC=2C=CC=CC=2)C1COC1=CC=CC=C1CCCCC1=CC=CC=C1 VDBNMFXOHYQYIQ-BDCODIICSA-N 0.000 description 1
- PIAUZKKLTLMFDR-YPJJGMIRSA-N tert-butyl (4r)-2-[[2-[2-(3-methylphenyl)ethyl]phenoxy]methyl]-4-phenylmethoxypyrrolidine-1-carboxylate Chemical compound CC1=CC=CC(CCC=2C(=CC=CC=2)OCC2N(C[C@@H](C2)OCC=2C=CC=CC=2)C(=O)OC(C)(C)C)=C1 PIAUZKKLTLMFDR-YPJJGMIRSA-N 0.000 description 1
- GDRCCIUALSUVPA-OZAIVSQSSA-N tert-butyl (4r)-4-hydroxy-2-[[2-(4-phenylbutyl)phenoxy]methyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@H](O)CC1COC1=CC=CC=C1CCCCC1=CC=CC=C1 GDRCCIUALSUVPA-OZAIVSQSSA-N 0.000 description 1
- XOCFORONWWIRFP-FOIFJWKZSA-N tert-butyl (4r)-4-hydroxy-2-[[2-[2-(3-methylphenyl)ethyl]phenoxy]methyl]pyrrolidine-1-carboxylate Chemical compound CC1=CC=CC(CCC=2C(=CC=CC=2)OCC2N(C[C@H](O)C2)C(=O)OC(C)(C)C)=C1 XOCFORONWWIRFP-FOIFJWKZSA-N 0.000 description 1
- LTVQOFUGXMVESU-UHFFFAOYSA-N tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CCO LTVQOFUGXMVESU-UHFFFAOYSA-N 0.000 description 1
- VSVOPDINJSHSBZ-UHFFFAOYSA-N tert-butyl 2-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1N(C(=O)OC(C)(C)C)CCC1 VSVOPDINJSHSBZ-UHFFFAOYSA-N 0.000 description 1
- JAZUVGBMJKAPFD-UHFFFAOYSA-N tert-butyl 2-[[2-(4-phenylbutyl)phenoxy]methyl]morpholine-4-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCOC1COC1=CC=CC=C1CCCCC1=CC=CC=C1 JAZUVGBMJKAPFD-UHFFFAOYSA-N 0.000 description 1
- RPUGIDCRPYGDEJ-UHFFFAOYSA-N tert-butyl 2-[[2-[2-[3-(methoxymethoxy)phenyl]ethyl]phenoxy]methyl]pyrrolidine-1-carboxylate Chemical compound COCOC1=CC=CC(CCC=2C(=CC=CC=2)OCC2N(CCC2)C(=O)OC(C)(C)C)=C1 RPUGIDCRPYGDEJ-UHFFFAOYSA-N 0.000 description 1
- UIJXHKXIOCDSEB-UHFFFAOYSA-N tert-butyl 3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(O)C1 UIJXHKXIOCDSEB-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- UJJDEOLXODWCGK-UHFFFAOYSA-N tert-butyl carbonochloridate Chemical compound CC(C)(C)OC(Cl)=O UJJDEOLXODWCGK-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- FEQPHYCEZKWPNE-UHFFFAOYSA-K trichlororhodium;triphenylphosphane Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FEQPHYCEZKWPNE-UHFFFAOYSA-K 0.000 description 1
- FJRPWCNFWGBGOF-UHFFFAOYSA-N tridecanoyl chloride Chemical compound CCCCCCCCCCCCC(Cl)=O FJRPWCNFWGBGOF-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000004951 trihalomethoxy group Chemical group 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
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- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
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- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
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- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP32060992 | 1992-11-30 | ||
JP33830792 | 1992-12-18 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO934311D0 NO934311D0 (no) | 1993-11-29 |
NO934311L NO934311L (no) | 1994-05-31 |
NO300539B1 true NO300539B1 (no) | 1997-06-16 |
Family
ID=26570150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO934311A NO300539B1 (no) | 1992-11-30 | 1993-11-29 | alfa,omega-diarylalkanderivater, med terapeutisk aktivitet for behandling og forhindring av sirkulasjonssykdommer og psykoser, og farmasöytiske preparater inneholdende disse derivater |
Country Status (14)
Country | Link |
---|---|
US (1) | US5556864A (ru) |
EP (2) | EP0844000A1 (ru) |
KR (1) | KR100287575B1 (ru) |
CN (1) | CN1044365C (ru) |
AU (1) | AU666590B2 (ru) |
CA (1) | CA2110251A1 (ru) |
CZ (1) | CZ283720B6 (ru) |
FI (1) | FI106957B (ru) |
HU (1) | HUT70031A (ru) |
IL (1) | IL107808A (ru) |
NO (1) | NO300539B1 (ru) |
NZ (1) | NZ250332A (ru) |
RU (1) | RU2105752C1 (ru) |
TW (1) | TW385302B (ru) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3274579B2 (ja) * | 1995-01-12 | 2002-04-15 | 住友製薬株式会社 | 脳血管障害に伴う精神症候治療剤 |
EP0790235A1 (en) * | 1996-02-15 | 1997-08-20 | Sankyo Company Limited | Diaryl alkane derivatives containing an alicyclic group, their preparation and their therapeutic and prophylactic uses |
ID21653A (id) * | 1996-11-28 | 1999-07-08 | Sankyo Co | Komposisi untuk pengobatan atau pencegahan pankreatitis yang mengandung turunan diarilalkana sebagai bahan aktif |
WO2001077091A2 (en) * | 2000-04-05 | 2001-10-18 | Tularik Inc. | Ns5b hcv polymerase inhibitors |
US20090093493A1 (en) * | 2007-10-09 | 2009-04-09 | Francesco Berardi | 1-phenylalcoxy-2-beta-phenylethyl derivatives as p-glycoprotein (p-gp) inhibitors useful in drug resistance events |
US8642583B2 (en) | 2008-10-30 | 2014-02-04 | Janssen Pharmaceutica Nv | Serotonin receptor modulators |
WO2010059390A1 (en) | 2008-10-30 | 2010-05-27 | Janssen Pharmaceutica Nv | Modulators of serotonin receptor |
CN106278831B (zh) * | 2015-06-10 | 2019-08-09 | 联化科技(台州)有限公司 | 2-苯乙基苯酚衍生物及其中间体的制备方法及中间体 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1111336A (en) * | 1964-07-24 | 1968-04-24 | Fisons Pharmaceuticals Ltd | Aryl ketones |
JPS5520740A (en) | 1978-08-01 | 1980-02-14 | Mitsubishi Chem Ind Ltd | Aminoalkoxybibenzyl and its acid addition salt |
US4220603A (en) | 1977-10-07 | 1980-09-02 | Mitsubishi Chemical Industries, Limited | Pharmaceutically active (omega-aminoalkoxy)bibenzyls |
US4179558A (en) * | 1978-01-30 | 1979-12-18 | E. R. Squibb & Sons, Inc. | Naphthalenone derivatives and analogs |
JPS5832847A (ja) * | 1981-08-20 | 1983-02-25 | Mitsubishi Chem Ind Ltd | (3−アミノプロポキシ)ビベンジル類 |
FR2518992A1 (fr) * | 1981-12-24 | 1983-07-01 | Delalande Sa | Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique |
US4792570A (en) * | 1984-04-06 | 1988-12-20 | Syntex (U.S.A.) Inc. | 3- and 4-biphenyloxyaminoalkanes and related compounds as anti-inflammatory and analgetic agents |
FR2568878B1 (fr) * | 1984-08-07 | 1986-11-21 | Cortial | Nouveaux derives de (phenylpiperazinylethylamine ethoxy)-4 phenol, leur methode de preparation et leur application therapeutique |
US4853408A (en) * | 1985-04-23 | 1989-08-01 | Roussel Uclaf | 4-phenylpropyl-indoles having antiarythmic activity |
DE3674521D1 (de) * | 1985-08-29 | 1990-10-31 | Hoechst Ag | 6-phenoxymethyl-4-hydroxytetrahydropyran-2-one, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte. |
EP0241918B1 (de) * | 1986-04-18 | 1992-05-27 | Hoechst Aktiengesellschaft | 1-Hydroxy-2-pyridone, Verfahren zu ihrer Herstellung und Arzneimittel, die sie enthalten, sowie bei der Herstellung der 1-Hydroxy-2-pyridone gebildete Zwischenprodukte |
EP0252007A3 (en) * | 1986-06-28 | 1989-07-05 | Ciba-Geigy Ag | 2-propanol derivatives as corrosion inhibitors |
US4920133A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
JPH02304022A (ja) | 1989-05-18 | 1990-12-17 | Mitsubishi Kasei Corp | セロトニン拮抗剤 |
MX9100513A (es) | 1990-08-06 | 1992-04-01 | Smith Kline French Lab | Compuestos |
GB9113031D0 (en) * | 1991-06-17 | 1991-08-07 | Smithkline Beecham Plc | Compounds |
GB9201749D0 (en) * | 1992-01-28 | 1992-03-11 | Smithkline Beecham Plc | Medicaments |
-
1993
- 1993-11-29 TW TW082110056A patent/TW385302B/zh not_active IP Right Cessation
- 1993-11-29 HU HU9303376A patent/HUT70031A/hu unknown
- 1993-11-29 NO NO934311A patent/NO300539B1/no not_active IP Right Cessation
- 1993-11-29 CA CA002110251A patent/CA2110251A1/en not_active Abandoned
- 1993-11-30 AU AU52017/93A patent/AU666590B2/en not_active Ceased
- 1993-11-30 EP EP97114529A patent/EP0844000A1/en not_active Withdrawn
- 1993-11-30 FI FI935341A patent/FI106957B/fi active
- 1993-11-30 KR KR1019930025951A patent/KR100287575B1/ko not_active IP Right Cessation
- 1993-11-30 EP EP93309570A patent/EP0600717A1/en not_active Withdrawn
- 1993-11-30 IL IL107808A patent/IL107808A/en not_active IP Right Cessation
- 1993-11-30 CN CN93121646A patent/CN1044365C/zh not_active Expired - Fee Related
- 1993-11-30 CZ CZ932582A patent/CZ283720B6/cs not_active IP Right Cessation
- 1993-11-30 NZ NZ250332A patent/NZ250332A/en unknown
- 1993-11-30 RU RU93053036A patent/RU2105752C1/ru active
-
1995
- 1995-01-05 US US08/369,255 patent/US5556864A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CA2110251A1 (en) | 1994-05-31 |
AU666590B2 (en) | 1996-02-15 |
FI935341A0 (fi) | 1993-11-30 |
NO934311L (no) | 1994-05-31 |
CN1044365C (zh) | 1999-07-28 |
NO934311D0 (no) | 1993-11-29 |
TW385302B (en) | 2000-03-21 |
AU5201793A (en) | 1994-06-09 |
IL107808A0 (en) | 1994-02-27 |
EP0600717A1 (en) | 1994-06-08 |
RU2105752C1 (ru) | 1998-02-27 |
FI935341A (fi) | 1994-05-31 |
CZ283720B6 (cs) | 1998-06-17 |
IL107808A (en) | 1998-04-05 |
HU9303376D0 (en) | 1994-03-28 |
KR940011412A (ko) | 1994-06-21 |
CN1102640A (zh) | 1995-05-17 |
CZ258293A3 (en) | 1994-06-15 |
HUT70031A (en) | 1995-09-28 |
US5556864A (en) | 1996-09-17 |
FI106957B (fi) | 2001-05-15 |
NZ250332A (en) | 1995-09-26 |
KR100287575B1 (ko) | 2001-05-02 |
EP0844000A1 (en) | 1998-05-27 |
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