HU198931B - Process for producing 2-square brackets open /piperidin-4-yl/-methyl square brackets closed -1,2,3,4-tetradihydro-9h-pyrido/3,4-b/indole derivatives and pharma ceutical compositions comprising same - Google Patents
Process for producing 2-square brackets open /piperidin-4-yl/-methyl square brackets closed -1,2,3,4-tetradihydro-9h-pyrido/3,4-b/indole derivatives and pharma ceutical compositions comprising same Download PDFInfo
- Publication number
- HU198931B HU198931B HU884105A HU410588A HU198931B HU 198931 B HU198931 B HU 198931B HU 884105 A HU884105 A HU 884105A HU 410588 A HU410588 A HU 410588A HU 198931 B HU198931 B HU 198931B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- group
- pyrido
- base
- Prior art date
Links
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims 5
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
- 239000002904 solvent Substances 0.000 claims description 36
- 239000002585 base Substances 0.000 claims description 31
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- URTPNQRAHXRPMP-UHFFFAOYSA-N 1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)OCC1=CC=CC=C1 URTPNQRAHXRPMP-UHFFFAOYSA-N 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims description 4
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 4
- DXQUCWFSWCEJSK-UHFFFAOYSA-N piperidin-4-yl(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)methanone Chemical compound C1CC(C2=CC=CC=C2N2)=C2CN1C(=O)C1CCNCC1 DXQUCWFSWCEJSK-UHFFFAOYSA-N 0.000 claims description 4
- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 3
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- BSCWDKWCQFYZPW-UHFFFAOYSA-N 2-(piperidin-4-ylmethyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole Chemical compound C1CC(C2=CC=CC=C2N2)=C2CN1CC1CCNCC1 BSCWDKWCQFYZPW-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- PGWGHYWMEHNJMV-UHFFFAOYSA-N benzyl 4-(1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbonyl)piperidine-1-carboxylate Chemical compound C1CC(C(=O)N2CC3=C(C4=CC=CC=C4N3)CC2)CCN1C(=O)OCC1=CC=CC=C1 PGWGHYWMEHNJMV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- KUBUQFFBRSHOMJ-UHFFFAOYSA-N benzyl 4-carbonochloridoylpiperidine-1-carboxylate Chemical compound C1CC(C(=O)Cl)CCN1C(=O)OCC1=CC=CC=C1 KUBUQFFBRSHOMJ-UHFFFAOYSA-N 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 2
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 abstract 1
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 abstract 1
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 abstract 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 abstract 1
- 101150111293 cor-1 gene Proteins 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000000872 buffer Substances 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- ASXGJMSKWNBENU-UHFFFAOYSA-N 8-OH-DPAT Chemical compound C1=CC(O)=C2CC(N(CCC)CCC)CCC2=C1 ASXGJMSKWNBENU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 210000001320 hippocampus Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- YHOYYHYBFSYOSQ-UHFFFAOYSA-N 3-methylbenzoyl chloride Chemical compound CC1=CC=CC(C(Cl)=O)=C1 YHOYYHYBFSYOSQ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- KTCZUHPULIZYJG-UHFFFAOYSA-N [4-(hydroxymethyl)piperidin-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2CCC(CO)CC2)=C1 KTCZUHPULIZYJG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- 230000002295 serotoninergic effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZRSCRAFWMMIDDX-UHFFFAOYSA-N (3-methylphenyl)-[4-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-ylmethyl)piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C(=O)N2CCC(CN3CC4=C(C5=CC=CC=C5N4)CC3)CC2)=C1 ZRSCRAFWMMIDDX-UHFFFAOYSA-N 0.000 description 1
- OUWLXWZZZKYIIF-UHFFFAOYSA-N 2-methylpiperidine-1-carboxamide Chemical compound CC1CCCCN1C(N)=O OUWLXWZZZKYIIF-UHFFFAOYSA-N 0.000 description 1
- VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000252095 Congridae Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 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
- 208000019695 Migraine disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- CWSHIWWZKCYQMW-UHFFFAOYSA-N [1-(3-methylbenzoyl)piperidin-4-yl]methyl 3-methylbenzoate Chemical compound CC1=CC=CC(C(=O)OCC2CCN(CC2)C(=O)C=2C=C(C)C=CC=2)=C1 CWSHIWWZKCYQMW-UHFFFAOYSA-N 0.000 description 1
- XCGSERQBWFFOKM-UHFFFAOYSA-N [1-(3-methylbenzoyl)piperidin-4-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CCN(C(=O)C=2C=C(C)C=CC=2)CC1 XCGSERQBWFFOKM-UHFFFAOYSA-N 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- ASQCOPJFYLJCGD-UHFFFAOYSA-N ethyl 1-benzylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1=CC=CC=C1 ASQCOPJFYLJCGD-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- YKFLJYAKACCWMH-UHFFFAOYSA-N methyl piperidine-1-carboxylate Chemical compound COC(=O)N1CCCCC1 YKFLJYAKACCWMH-UHFFFAOYSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000010807 negative regulation of binding Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8711291A FR2619111B1 (fr) | 1987-08-07 | 1987-08-07 | Derives de (piperidinyl-4)methyl-2 tetrahydro-1,2,3,4 9h-pyrido (3,4-b) indole, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT48242A HUT48242A (en) | 1989-05-29 |
| HU198931B true HU198931B (en) | 1989-12-28 |
Family
ID=9354027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU884105A HU198931B (en) | 1987-08-07 | 1988-08-05 | Process for producing 2-square brackets open /piperidin-4-yl/-methyl square brackets closed -1,2,3,4-tetradihydro-9h-pyrido/3,4-b/indole derivatives and pharma ceutical compositions comprising same |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4977159A (OSRAM) |
| EP (1) | EP0302788B1 (OSRAM) |
| JP (1) | JPS6466185A (OSRAM) |
| KR (1) | KR890003756A (OSRAM) |
| AT (1) | ATE72436T1 (OSRAM) |
| AU (1) | AU597188B2 (OSRAM) |
| DE (1) | DE3868301D1 (OSRAM) |
| DK (1) | DK437788A (OSRAM) |
| FI (1) | FI883669A7 (OSRAM) |
| FR (1) | FR2619111B1 (OSRAM) |
| GR (1) | GR3003920T3 (OSRAM) |
| HU (1) | HU198931B (OSRAM) |
| IL (1) | IL87343A0 (OSRAM) |
| NO (1) | NO166129C (OSRAM) |
| NZ (1) | NZ225706A (OSRAM) |
| PT (1) | PT88206B (OSRAM) |
| ZA (1) | ZA885788B (OSRAM) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4978669A (en) * | 1989-06-08 | 1990-12-18 | Neurex Corporation | Method of suppressing appetite by administration of tetrahydro-beta-carboline derivatives |
| US5102889B1 (en) * | 1990-09-27 | 1993-05-11 | 2-(4-piperidinyl)-1h-pyrido(4,3-b)indol-1-ones and related compounds | |
| US5229517A (en) * | 1990-09-27 | 1993-07-20 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(4-Piperindinyl)-1H-pyrido[4,3-B]indol-1-ones and related compounds |
| US5455254A (en) * | 1991-02-15 | 1995-10-03 | Mondadori; Cesare | Substituted benzofuranylpiperidine as a nootropic agent |
| RU2095339C1 (ru) * | 1991-10-17 | 1997-11-10 | Циба-Гейги АГ | Производные гидрохинона в свободном виде или в виде соли, способы их получения, производные пиперидина и способы их получения |
| US5693807A (en) * | 1992-10-14 | 1997-12-02 | Ciba-Geigy Corporation | Substituted hydroquinone derivatives |
| FR2715659B1 (fr) * | 1994-02-03 | 1996-03-22 | Synthelabo | Dérivés de 3-(2-aminoéthyl)-4-[3-(trifluorométhyl)benzoyl]-3,4-dihydro-2H-1,4-benzoxazine, leur préparation et leur application en thérapeutique. |
| CN1109880A (zh) * | 1994-02-03 | 1995-10-11 | 合成实验室公司 | 3-(2-氨基乙基)-4-[3-(三氟甲基)苯甲酰基]-3，4-二氢-2h-1，4-苯并噁嗪衍生物、制备及其应用 |
| AU3831495A (en) * | 1994-10-20 | 1996-05-15 | American Home Products Corporation | Indole derivatives useful as serotonergic agents |
| US6255302B1 (en) | 1998-12-17 | 2001-07-03 | American Home Products Corporation | 1,4-piperazine derivatives |
| CO5180550A1 (es) | 1999-04-19 | 2002-07-30 | Smithkline Beecham Corp | Inhibidores de fab i |
| AR024158A1 (es) | 1999-06-01 | 2002-09-04 | Smithkline Beecham Corp | Compuestos antibacterianos |
| BRPI0014470B1 (pt) * | 1999-10-08 | 2016-08-23 | Affinium Pharm Inc | compostos inibidores de fab i, composição farmacêutica, processo de preparação dos compostos e uso dos compostos para a produção de medicamento para tratamento de infecções bacterianas |
| US6762201B1 (en) | 1999-10-08 | 2004-07-13 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| US6730684B1 (en) | 1999-10-08 | 2004-05-04 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| SK287188B6 (sk) | 1999-12-10 | 2010-02-08 | Pfizer Products Inc. | Pyrolo [2,3-d]pyrimidínová zlúčenina, jej použitie a farmaceutická kompozícia alebo kombinácia s jej obsahom |
| WO2003088897A2 (en) | 2001-04-06 | 2003-10-30 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| AU2002360561A1 (en) * | 2001-12-11 | 2003-06-23 | Sepracor, Inc. | 4-substituted piperidines, and methods of use thereof |
| RU2309147C9 (ru) * | 2002-11-21 | 2008-03-20 | Пфайзер Продактс Инк. | Производные 3-аминопиперидина и способы их получения |
| US7790709B2 (en) | 2002-12-06 | 2010-09-07 | Affinium Pharmaceuticals, Inc. | Heterocyclic compounds, methods of making them and their use in therapy |
| WO2004082586A2 (en) | 2003-03-17 | 2004-09-30 | Affinium Pharmaceuticals, Inc. | Phamaceutical compositions comprising inhibitors of fab i and further antibiotics |
| US20060273819A1 (en) * | 2003-04-29 | 2006-12-07 | Timothy Opperman | Antibiotic tetrahydro-beta-carboline derivatives |
| US8450307B2 (en) | 2004-06-04 | 2013-05-28 | Affinium Pharmaceuticals, Inc. | Therapeutic agents, and methods of making and using the same |
| WO2008009122A1 (en) | 2006-07-20 | 2008-01-24 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab i inhibitors |
| EP3255045A1 (en) | 2007-02-16 | 2017-12-13 | Debiopharm International SA | Salts, prodrugs and polymorphs of fab i inhibitors |
| BR122021020778B1 (pt) | 2012-06-19 | 2022-07-12 | Debiopharm International Sa | Derivados de pró-fármaco de (e)-n-metil-n-((3-metilbenzofuran-2-il) metil)-3-(7-oxo-5,6,7,8-tetraidro- 1, 8- naftirindin-3-il) acrilamida |
| HUE052140T2 (hu) | 2016-02-26 | 2021-04-28 | Debiopharm Int Sa | Diabéteszes lábfertõzések kezelésére szolgáló gyógyszer |
| PL3923914T3 (pl) | 2019-02-14 | 2023-08-07 | Debiopharm International S.A. | Preparat afabicyny, sposób jego wytwarzania |
| WO2020249731A1 (en) | 2019-06-14 | 2020-12-17 | Debiopharm International S.A. | Afabicin for use for treating bacterial infections involving biofilm |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539407A (en) * | 1983-12-13 | 1985-09-03 | American Home Products Corporation | β-Carboline anticonvulsants |
| US4663456A (en) * | 1985-09-16 | 1987-05-05 | American Home Products Corporation | 2-(substituted piperazinylalkyl)β-carbolines useful in treatment of psychological disorders |
-
1987
- 1987-08-07 FR FR8711291A patent/FR2619111B1/fr not_active Expired - Fee Related
-
1988
- 1988-08-03 AT AT88402024T patent/ATE72436T1/de not_active IP Right Cessation
- 1988-08-03 DE DE8888402024T patent/DE3868301D1/de not_active Expired - Fee Related
- 1988-08-03 EP EP88402024A patent/EP0302788B1/fr not_active Expired - Lifetime
- 1988-08-04 IL IL87343A patent/IL87343A0/xx unknown
- 1988-08-05 PT PT88206A patent/PT88206B/pt not_active IP Right Cessation
- 1988-08-05 NZ NZ225706A patent/NZ225706A/en unknown
- 1988-08-05 ZA ZA885788A patent/ZA885788B/xx unknown
- 1988-08-05 HU HU884105A patent/HU198931B/hu not_active IP Right Cessation
- 1988-08-05 US US07/228,751 patent/US4977159A/en not_active Expired - Fee Related
- 1988-08-05 KR KR1019880010017A patent/KR890003756A/ko not_active Withdrawn
- 1988-08-05 FI FI883669A patent/FI883669A7/fi not_active Application Discontinuation
- 1988-08-05 DK DK437788A patent/DK437788A/da not_active Application Discontinuation
- 1988-08-05 JP JP63197011A patent/JPS6466185A/ja active Pending
- 1988-08-05 NO NO883487A patent/NO166129C/no unknown
- 1988-08-05 AU AU20445/88A patent/AU597188B2/en not_active Ceased
-
1992
- 1992-02-27 GR GR920400343T patent/GR3003920T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO883487D0 (no) | 1988-08-05 |
| IL87343A0 (en) | 1989-01-31 |
| ZA885788B (en) | 1989-04-26 |
| NO883487L (no) | 1989-02-08 |
| DK437788D0 (da) | 1988-08-05 |
| NO166129C (no) | 1991-06-05 |
| NO166129B (no) | 1991-02-25 |
| ATE72436T1 (de) | 1992-02-15 |
| GR3003920T3 (OSRAM) | 1993-03-16 |
| FI883669A0 (fi) | 1988-08-05 |
| HUT48242A (en) | 1989-05-29 |
| DE3868301D1 (de) | 1992-03-19 |
| AU2044588A (en) | 1989-02-09 |
| FI883669A7 (fi) | 1989-02-08 |
| AU597188B2 (en) | 1990-05-24 |
| JPS6466185A (en) | 1989-03-13 |
| US4977159A (en) | 1990-12-11 |
| FR2619111B1 (fr) | 1991-01-11 |
| PT88206A (pt) | 1989-06-30 |
| EP0302788A1 (fr) | 1989-02-08 |
| EP0302788B1 (fr) | 1992-02-05 |
| DK437788A (da) | 1989-02-07 |
| KR890003756A (ko) | 1989-04-17 |
| FR2619111A1 (fr) | 1989-02-10 |
| PT88206B (pt) | 1995-05-04 |
| NZ225706A (en) | 1990-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU198931B (en) | Process for producing 2-square brackets open /piperidin-4-yl/-methyl square brackets closed -1,2,3,4-tetradihydro-9h-pyrido/3,4-b/indole derivatives and pharma ceutical compositions comprising same | |
| US5652246A (en) | Piperidine compounds | |
| US5585378A (en) | Composition containing an oxoindole compound | |
| US5834493A (en) | Indole derivatives as 5-HT1A and/or 5-HT2 ligands | |
| DE60022504T2 (de) | Phenoxypropylamin-derivate | |
| EP0144986B1 (en) | Indole-3-carboxamide derivatives | |
| JP3165181B2 (ja) | 新規の３−アリールインドールおよび３−アリールインダゾール誘導体 | |
| JPH11501640A (ja) | ５−ｈｔ▲下４▼拮抗作用を有するジ−置換１，４−ピペリジンエステル類及びアミド類 | |
| JPH0699388B2 (ja) | ６−置換−４−ジアルキルアミノテトラヒドロベンズ〔ｃ，ｄ〕インド−ル類 | |
| EA008627B1 (ru) | Замещенные галогеном производные 4-фенил-1-пиперазинила, их применение и содержащая их фармацевтическая композиция | |
| US5703087A (en) | Phenyl indole compounds | |
| KR860001819B1 (ko) | 헥사히드로-트란스-피리도인돌 유도체의 제조 방법 | |
| US4432978A (en) | Hexahydro-trans-pyridoindole | |
| US5773448A (en) | Pharmaceutical compounds | |
| US5344927A (en) | Tetrahydrobenzimidazole derivatives and pharmaceutical compositions containing same | |
| US5118687A (en) | 1-oxa-2-oxo-8-azaspiro(4,5)decane derivatives, pharmaceutical compositions containing them and process for preparing same | |
| HU201075B (en) | Process for producing 2-((piperidin-4-yl)-methyl)-benzofuro)2,3-c)- pyridine derivatives and pharmaceutical compositions containing them | |
| US4431649A (en) | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents | |
| US4427679A (en) | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents | |
| US4431646A (en) | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents | |
| JPH04210970A (ja) | ベンズアミド誘導体及びその中間体 | |
| JPWO1999055674A1 (ja) | １−［（１−置換−４−ピペリジニル）メチル］−４−ピペリジン誘導体、その製造方法、それを含有する医薬組成物および該化合物の中間体 | |
| HK1013817B (en) | Phenylindole compounds | |
| HU199451B (en) | Process for producing 2-square brackets open /piperidin-4-yl/-methyl square brackets closed-1,2,3,4-tetrahydroisoquinoline derivatives and pharmaceutical compositions comprising same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |