DD213217A5 - Verfahren zur herstellung von beta-carbolinen - Google Patents
Verfahren zur herstellung von beta-carbolinen Download PDFInfo
- Publication number
- DD213217A5 DD213217A5 DD83256042A DD25604283A DD213217A5 DD 213217 A5 DD213217 A5 DD 213217A5 DD 83256042 A DD83256042 A DD 83256042A DD 25604283 A DD25604283 A DD 25604283A DD 213217 A5 DD213217 A5 DD 213217A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- carboline
- formula
- meaning
- alkyl
- carboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 34
- 238000002360 preparation method Methods 0.000 title description 15
- 230000008569 process Effects 0.000 title description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 109
- 150000001875 compounds Chemical class 0.000 claims description 47
- -1 copper (I) halide Chemical class 0.000 claims description 39
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 5
- UGMPOJSWOINMDE-UHFFFAOYSA-N 9h-pyrido[3,4-b]indol-3-amine Chemical compound N1C2=CC=CC=C2C2=C1C=NC(N)=C2 UGMPOJSWOINMDE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002828 nitro derivatives Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 claims description 2
- 238000000297 Sandmeyer reaction Methods 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 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
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 claims 1
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 6
- 210000003169 central nervous system Anatomy 0.000 abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000005923 long-lasting effect Effects 0.000 abstract 1
- 229940127557 pharmaceutical product Drugs 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- 238000002844 melting Methods 0.000 description 64
- 230000008018 melting Effects 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- 239000012362 glacial acetic acid Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- DSUBZVLNKPDONN-UHFFFAOYSA-N 1-(9h-pyrido[3,4-b]indol-3-yl)ethanol Chemical compound N1C2=CC=CC=C2C2=C1C=NC(C(O)C)=C2 DSUBZVLNKPDONN-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- ARLVFKCLBYUINL-UHFFFAOYSA-N 9h-pyrido[3,4-b]indole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=NC(C(=O)O)=C2 ARLVFKCLBYUINL-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000006073 displacement reaction Methods 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- XOHBPUCYRSORIZ-UHFFFAOYSA-N 3-methyl-9h-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1C=NC(C)=C2 XOHBPUCYRSORIZ-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 4
- IIJKHXNPDNDYJV-UHFFFAOYSA-N ethyl 9h-pyrido[3,4-b]indole-4-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C=NC=C2C(=O)OCC IIJKHXNPDNDYJV-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229960002200 flunitrazepam Drugs 0.000 description 4
- 150000002475 indoles Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- NBTKOJDJAKQGEG-UHFFFAOYSA-N 1-(9h-pyrido[3,4-b]indol-5-yl)ethanone Chemical compound N1C2=CN=CC=C2C2=C1C=CC=C2C(=O)C NBTKOJDJAKQGEG-UHFFFAOYSA-N 0.000 description 3
- VEBURLGGACYRBL-UHFFFAOYSA-N 3-(2-phenylethenyl)-9h-pyrido[3,4-b]indole Chemical compound C=1C(C2=CC=CC=C2N2)=C2C=NC=1C=CC1=CC=CC=C1 VEBURLGGACYRBL-UHFFFAOYSA-N 0.000 description 3
- VHCZZCXMIBIJIN-UHFFFAOYSA-N 3-(chloromethyl)-9h-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1C=NC(CCl)=C2 VHCZZCXMIBIJIN-UHFFFAOYSA-N 0.000 description 3
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 3
- DUVJFXSQMXNUBO-UHFFFAOYSA-N 3-bromo-9h-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1C=NC(Br)=C2 DUVJFXSQMXNUBO-UHFFFAOYSA-N 0.000 description 3
- XKCXIUDPGSNQIQ-UHFFFAOYSA-N 3-hydroxymethyl-beta-carboline Natural products C12=CC=CC=C2NC2=C1C=CN=C2CO XKCXIUDPGSNQIQ-UHFFFAOYSA-N 0.000 description 3
- PKDNEEZFQROQRV-UHFFFAOYSA-N 3-methylsulfanyl-9h-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1C=NC(SC)=C2 PKDNEEZFQROQRV-UHFFFAOYSA-N 0.000 description 3
- OLZWIRPIGQYPES-UHFFFAOYSA-N 3-piperidin-1-yl-9h-pyrido[3,4-b]indole Chemical compound C1CCCCN1C1=CC(C2=CC=CC=C2N2)=C2C=N1 OLZWIRPIGQYPES-UHFFFAOYSA-N 0.000 description 3
- ZWZNGOCCOYPAHW-UHFFFAOYSA-N 3-pyrrol-1-yl-9h-pyrido[3,4-b]indole Chemical compound C1=CC=CN1C1=CC(C2=CC=CC=C2N2)=C2C=N1 ZWZNGOCCOYPAHW-UHFFFAOYSA-N 0.000 description 3
- CPBYHTDUBNSBQM-UHFFFAOYSA-N 9H-pyrido[3,4-b]indol-3-ylmethanol Chemical compound N1C2=CC=CC=C2C2=C1C=NC(CO)=C2 CPBYHTDUBNSBQM-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 102000004300 GABA-A Receptors Human genes 0.000 description 3
- 108090000839 GABA-A Receptors Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 230000016571 aggressive behavior Effects 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- YDQHHZTYPPUDLH-UHFFFAOYSA-N 9h-pyrido[3,4-b]indole-4-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=NC=C2C(=O)O YDQHHZTYPPUDLH-UHFFFAOYSA-N 0.000 description 1
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- GEFXBWSREYXFIC-UHFFFAOYSA-N [3-(hydroxymethyl)-1-(oxan-2-yl)-9H-pyrido[3,4-b]indol-6-yl] hypobromite Chemical compound BrOC=1C=C2C=3C=C(N=C(C=3NC2=CC=1)C1OCCCC1)CO GEFXBWSREYXFIC-UHFFFAOYSA-N 0.000 description 1
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- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
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- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- JZIFOHJMLBAWQZ-UHFFFAOYSA-N n-(9h-pyrido[3,4-b]indol-3-yl)acetamide Chemical compound N1C2=CC=CC=C2C2=C1C=NC(NC(=O)C)=C2 JZIFOHJMLBAWQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- HHFOOWPWAXNJNY-UHFFFAOYSA-N promoxolane Chemical compound CC(C)C1(C(C)C)OCC(CO)O1 HHFOOWPWAXNJNY-UHFFFAOYSA-N 0.000 description 1
- 229950008352 promoxolane Drugs 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- VFTBEJYSQUHAGA-UHFFFAOYSA-N propyl 9H-pyrido[3,4-b]indole-1-carboxylate Chemical compound C(CC)OC(=O)C1=NC=CC2=C1NC1=CC=CC=C21 VFTBEJYSQUHAGA-UHFFFAOYSA-N 0.000 description 1
- SDYYCDVGYIPTOB-UHFFFAOYSA-N propyl 9h-pyrido[3,4-b]indole-4-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C=NC=C2C(=O)OCCC SDYYCDVGYIPTOB-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000003345 scintillation counting Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- RQLKZZBMSWQOQJ-UHFFFAOYSA-N taraxacine-A Natural products C12=CC=CC=C2NC2=C1C=CN=C2OC RQLKZZBMSWQOQJ-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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- 238000010792 warming Methods 0.000 description 1
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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
-
- 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
-
- 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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19823240514 DE3240514A1 (de) | 1982-10-29 | 1982-10-29 | Ss-carboline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Publications (1)
Publication Number | Publication Date |
---|---|
DD213217A5 true DD213217A5 (de) | 1984-09-05 |
Family
ID=6177153
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD83256042A DD213217A5 (de) | 1982-10-29 | 1983-10-27 | Verfahren zur herstellung von beta-carbolinen |
Country Status (18)
Country | Link |
---|---|
US (1) | US4731358A (xx) |
EP (1) | EP0110814B1 (xx) |
JP (1) | JPH0633260B2 (xx) |
AT (1) | ATE48602T1 (xx) |
AU (1) | AU568513B2 (xx) |
CA (1) | CA1260475A (xx) |
DD (1) | DD213217A5 (xx) |
DE (2) | DE3240514A1 (xx) |
DK (1) | DK495683A (xx) |
ES (1) | ES526896A0 (xx) |
FI (1) | FI833918A (xx) |
GR (1) | GR79637B (xx) |
HU (1) | HU198208B (xx) |
IE (1) | IE56155B1 (xx) |
IL (1) | IL70077A0 (xx) |
NO (1) | NO833942L (xx) |
NZ (1) | NZ205949A (xx) |
ZA (1) | ZA838072B (xx) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3240511A1 (de) * | 1982-10-29 | 1984-05-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur herstellung von ss-carbolinderivaten |
DE3322895A1 (de) * | 1983-06-23 | 1985-01-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue ss-carboline, verfahren zur ihrer herstellung und ihre verwendung als arzneimittel (s) |
US4631149A (en) * | 1983-07-25 | 1986-12-23 | University Of Illinois | Antiviral eudistomins from a marine tunicate |
DE3504045A1 (de) * | 1985-02-04 | 1986-08-07 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur herstellung von ss-carbolinen durch dehydrierung |
DE3535927A1 (de) * | 1985-10-04 | 1987-04-09 | Schering Ag | 3-vinyl- und 3-ethinyl-ss-carbolinderivate, ihre herstellung und ihre verwendung als arzneimittel |
US4952584A (en) * | 1986-01-11 | 1990-08-28 | Beecham Group P.L.C. | 9H-pyrido[2,B-8]indole-3-carboxylic acid ester compounds having useful pharmaceutical activity |
US4789676A (en) * | 1986-03-05 | 1988-12-06 | Merrell Dow Pharmaceuticals Inc. | Aromatic 2-aminoalkyl-1,2-benzoisothiazol-3(2H)one-1,1-dioxide derivatives, usefull as anxiolytic agents |
US5223509A (en) * | 1987-08-17 | 1993-06-29 | Merck & Co., Inc. | β-carbolines as cholecystokinin and gastrin antagonists |
EP0304223A3 (en) * | 1987-08-17 | 1990-10-24 | Merck & Co. Inc. | Beta-carbolines as cholecy-stokinin and gastrin antagonist |
AU619203B2 (en) * | 1987-08-28 | 1992-01-23 | Schering Aktiengesellschaft | Isoxazole-beta-carboline derivatives |
DE4029389A1 (de) * | 1990-09-13 | 1992-03-26 | Schering Ag | Verfahren zur herstellung von (beta)-carbolin-derivaten |
US5350750A (en) * | 1991-04-27 | 1994-09-27 | Schering Aktiengesellschaft | β-carboline-3-hydroxyalkylcarboxylic acid ester derivatives, process for their production and their use in pharmaceutical agents |
HUT75522A (en) * | 1994-03-11 | 1997-05-28 | Lilly Co Eli | Indole-, pyrido-indole-, indolo-quinoline- and benzo-pyrido-indole-derivatives, method for treating 5ht2b receptor related conditions, pharmaceutical compositions containing them |
ES2194213T3 (es) * | 1996-08-09 | 2003-11-16 | Boehringer Ingelheim Pharma | Beta-carbolinas-4- sustituidas en calidad de inmunomoduladores. |
EP1209158A1 (en) * | 2000-11-18 | 2002-05-29 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines |
EP1134221A1 (en) * | 2000-03-15 | 2001-09-19 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines as lkB kinase inhibitors |
HUP0300894A3 (en) | 2000-03-15 | 2008-05-28 | Sanofi Aventis Deutschland | Substituted beta-carbolines, process for their preparation, pharmaceutical compositions containing them and their use |
US20030045541A1 (en) * | 2001-07-23 | 2003-03-06 | Christopher Bruckner | GABA-Receptor modulators with NMDA-Antagonistic activity |
DE102007009264A1 (de) * | 2007-02-26 | 2008-08-28 | Ellneuroxx Ltd. | 9-Alkyl-ß-Carboline zur Behandlung von neurodegenerativen Erkrankungen |
JP5627705B2 (ja) | 2009-12-28 | 2014-11-19 | アウディオキュア ファーマ ゲーエムベーハー | 聴力損傷および目まいの治療用のβ−カルボリン |
CN102146080B (zh) * | 2010-02-10 | 2013-01-30 | 新疆华世丹药业股份有限公司 | β-咔啉碱衍生物类化合物及其应用 |
EP2455378A1 (en) | 2010-11-03 | 2012-05-23 | Philip Morris Products S.A. | Carbazole and carboline derivatives, and preparation and therapeutic applications thereof |
CN102093347A (zh) * | 2010-12-17 | 2011-06-15 | 中国药科大学 | 1,3,6-三取代-β-咔啉类细胞周期蛋白依赖性激酶2抑制剂及其用途 |
US11117893B2 (en) * | 2018-09-24 | 2021-09-14 | Union University | Methods for preparation of substituted pyridines and related novel compounds |
US11485734B2 (en) | 2018-10-02 | 2022-11-01 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2C (5-HT2C) |
EP4125874A4 (en) * | 2020-03-25 | 2024-05-01 | SRI International | LIPOXYGENASE INHIBITORS |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4730718U (xx) * | 1971-04-27 | 1972-12-07 | ||
NZ194747A (en) * | 1979-08-29 | 1988-11-29 | Schering Ag | 9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives |
JPS57123180A (en) * | 1980-12-17 | 1982-07-31 | Schering Ag | 3-substituted beta-carboline, manufacture and psychotropic drug containing same |
DE3240511A1 (de) * | 1982-10-29 | 1984-05-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur herstellung von ss-carbolinderivaten |
DE3322895A1 (de) * | 1983-06-23 | 1985-01-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue ss-carboline, verfahren zur ihrer herstellung und ihre verwendung als arzneimittel (s) |
JPH07230718A (ja) * | 1994-02-17 | 1995-08-29 | Hitachi Plant Eng & Constr Co Ltd | クリーンルーム用プレハブ分岐付ケーブル |
-
1982
- 1982-10-29 DE DE19823240514 patent/DE3240514A1/de not_active Withdrawn
-
1983
- 1983-10-13 NZ NZ205949A patent/NZ205949A/en unknown
- 1983-10-20 JP JP58195407A patent/JPH0633260B2/ja not_active Expired - Lifetime
- 1983-10-26 FI FI833918A patent/FI833918A/fi not_active Application Discontinuation
- 1983-10-26 GR GR72789A patent/GR79637B/el unknown
- 1983-10-27 AT AT83730103T patent/ATE48602T1/de not_active IP Right Cessation
- 1983-10-27 EP EP83730103A patent/EP0110814B1/de not_active Expired
- 1983-10-27 DE DE8383730103T patent/DE3380958D1/de not_active Expired - Lifetime
- 1983-10-27 DD DD83256042A patent/DD213217A5/de unknown
- 1983-10-28 IL IL70077A patent/IL70077A0/xx unknown
- 1983-10-28 NO NO833942A patent/NO833942L/no unknown
- 1983-10-28 IE IE2529/83A patent/IE56155B1/en not_active IP Right Cessation
- 1983-10-28 ZA ZA838072A patent/ZA838072B/xx unknown
- 1983-10-28 AU AU20694/83A patent/AU568513B2/en not_active Ceased
- 1983-10-28 ES ES526896A patent/ES526896A0/es active Granted
- 1983-10-28 HU HU833711A patent/HU198208B/hu not_active IP Right Cessation
- 1983-10-28 CA CA000439951A patent/CA1260475A/en not_active Expired
- 1983-10-28 DK DK495683A patent/DK495683A/da not_active Application Discontinuation
-
1986
- 1986-09-02 US US06/902,855 patent/US4731358A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPH0633260B2 (ja) | 1994-05-02 |
GR79637B (xx) | 1984-10-31 |
EP0110814A2 (de) | 1984-06-13 |
US4731358A (en) | 1988-03-15 |
ZA838072B (en) | 1984-06-27 |
DE3240514A1 (de) | 1984-05-03 |
FI833918A0 (fi) | 1983-10-26 |
IL70077A0 (en) | 1984-01-31 |
FI833918A (fi) | 1984-04-30 |
CA1260475A (en) | 1989-09-26 |
DE3380958D1 (de) | 1990-01-18 |
NZ205949A (en) | 1987-03-31 |
ES8406477A1 (es) | 1984-08-01 |
ES526896A0 (es) | 1984-08-01 |
IE832529L (en) | 1984-04-29 |
HU198208B (en) | 1989-08-28 |
DK495683A (da) | 1984-04-30 |
EP0110814B1 (de) | 1989-12-13 |
DK495683D0 (da) | 1983-10-28 |
NO833942L (no) | 1984-04-30 |
EP0110814A3 (en) | 1985-07-24 |
AU2069483A (en) | 1984-05-03 |
AU568513B2 (en) | 1988-01-07 |
ATE48602T1 (de) | 1989-12-15 |
IE56155B1 (en) | 1991-05-08 |
JPS5989678A (ja) | 1984-05-23 |
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