CA1053682A - Carbazole derivatives and process for their manufacture - Google Patents
Carbazole derivatives and process for their manufactureInfo
- Publication number
- CA1053682A CA1053682A CA205,063A CA205063A CA1053682A CA 1053682 A CA1053682 A CA 1053682A CA 205063 A CA205063 A CA 205063A CA 1053682 A CA1053682 A CA 1053682A
- Authority
- CA
- Canada
- Prior art keywords
- carbazole
- carboxylic acid
- methyl
- chloro
- produced
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 142
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 oximinocarbonyl Chemical group 0.000 claims abstract description 37
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 14
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000005042 acyloxymethyl group Chemical group 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 84
- 239000000126 substance Substances 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 55
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 52
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 39
- 238000010992 reflux Methods 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 21
- 239000008096 xylene Substances 0.000 claims description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 20
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 18
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 16
- 150000001716 carbazoles Chemical class 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- NDRBUFWYCLTVBV-UHFFFAOYSA-N ethyl 7-chloro-8-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(C)C(Cl)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 NDRBUFWYCLTVBV-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- NAERWUXELMQKIT-UHFFFAOYSA-N 7-chloro-8-methyl-9h-carbazole-1-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C2=C1C(C)=C(Cl)C=C2 NAERWUXELMQKIT-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- IGDIDRYAZLWWOG-UHFFFAOYSA-N ethyl 7-chloro-8-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=C(C(=C3NC12)C)Cl IGDIDRYAZLWWOG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- BRYNDDZGTHSCCE-UHFFFAOYSA-N 7,8-dichloro-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=C(Cl)C(Cl)=C2NC2=C1C=CC=C2C(=O)O BRYNDDZGTHSCCE-UHFFFAOYSA-N 0.000 claims description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- DXDQBVWBDNRQFI-UHFFFAOYSA-N ethyl 7,8-dimethyl-9H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1=CC=CC=2C3=CC=C(C(=C3NC12)C)C DXDQBVWBDNRQFI-UHFFFAOYSA-N 0.000 claims description 5
- DYEAIOQFDWDMLH-UHFFFAOYSA-N ethyl 8-methyl-9h-carbazole-1-carboxylate Chemical compound N1C2=C(C)C=CC=C2C2=C1C(C(=O)OCC)=CC=C2 DYEAIOQFDWDMLH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- LKZDXEIDUKUTMD-UHFFFAOYSA-N 7,8-dimethyl-9h-carbazole-1-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2NC3=C(C)C(C)=CC=C3C2=C1 LKZDXEIDUKUTMD-UHFFFAOYSA-N 0.000 claims description 4
- FZTCDLZTKNSKCX-UHFFFAOYSA-N 7-chloro-8-methyl-9h-carbazole-1-carbonitrile Chemical compound C12=CC=CC(C#N)=C2NC2=C1C=CC(Cl)=C2C FZTCDLZTKNSKCX-UHFFFAOYSA-N 0.000 claims description 4
- ZAYRIWYHTHCTNP-UHFFFAOYSA-N 7-chloro-8-methyl-9h-carbazole-1-carboxamide Chemical compound N1C2=C(C(N)=O)C=CC=C2C2=C1C(C)=C(Cl)C=C2 ZAYRIWYHTHCTNP-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 claims description 4
- MZELDQBKQWZTDJ-UHFFFAOYSA-N ethyl 11H-benzo[a]carbazole-1-carboxylate Chemical compound C1=CC=C2NC3=C4C(C(=O)OCC)=CC=CC4=CC=C3C2=C1 MZELDQBKQWZTDJ-UHFFFAOYSA-N 0.000 claims description 4
- FFZCZDLYNHBTKH-UHFFFAOYSA-N ethyl 5-chloro-8-methoxy-9H-carbazole-1-carboxylate Chemical compound N1C2=C(OC)C=CC(Cl)=C2C2=C1C(C(=O)OCC)=CC=C2 FFZCZDLYNHBTKH-UHFFFAOYSA-N 0.000 claims description 4
- VKWLMWIFIMGBRR-UHFFFAOYSA-N ethyl 5-chloro-8-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(C)C=CC(Cl)=C2C2=C1C(C(=O)OCC)=CC=C2 VKWLMWIFIMGBRR-UHFFFAOYSA-N 0.000 claims description 4
- RNCXMGDBZYDSOE-UHFFFAOYSA-N ethyl 6-methoxy-9h-carbazole-1-carboxylate Chemical compound N1C2=CC=C(OC)C=C2C2=C1C(C(=O)OCC)=CC=C2 RNCXMGDBZYDSOE-UHFFFAOYSA-N 0.000 claims description 4
- CUZKPULUXHXBNN-UHFFFAOYSA-N ethyl 7-chloro-3,8-dimethyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(C)C(Cl)=CC=C2C2=C1C(C(=O)OCC)=CC(C)=C2 CUZKPULUXHXBNN-UHFFFAOYSA-N 0.000 claims description 4
- BKJULXAGOYSYHN-UHFFFAOYSA-N ethyl 7-chloro-6-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=CC(Cl)=C(C)C=C2C2=C1C(C(=O)OCC)=CC=C2 BKJULXAGOYSYHN-UHFFFAOYSA-N 0.000 claims description 4
- AYTLNKFBPOVHFY-UHFFFAOYSA-N ethyl 7-chloro-8-ethyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(CC)C(Cl)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 AYTLNKFBPOVHFY-UHFFFAOYSA-N 0.000 claims description 4
- SDNLPLNSCOFFQF-UHFFFAOYSA-N ethyl 7-fluoro-9H-carbazole-1-carboxylate Chemical compound N1C2=CC(F)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 SDNLPLNSCOFFQF-UHFFFAOYSA-N 0.000 claims description 4
- OKDJIWVZJOYKLB-UHFFFAOYSA-N ethyl 8-chloro-7-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=C(Cl)C(C)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 OKDJIWVZJOYKLB-UHFFFAOYSA-N 0.000 claims description 4
- DZFPVTAORISKOL-UHFFFAOYSA-N ethyl 8-methoxy-9h-carbazole-1-carboxylate Chemical compound N1C2=C(OC)C=CC=C2C2=C1C(C(=O)OCC)=CC=C2 DZFPVTAORISKOL-UHFFFAOYSA-N 0.000 claims description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- QCOBKRQAYAEBII-UHFFFAOYSA-N methyl 3-chloro-6,7,8,9-tetrahydro-5H-carbazole-1-carboxylate Chemical compound COC(=O)C1=CC(=CC=2C=3CCCCC3NC12)Cl QCOBKRQAYAEBII-UHFFFAOYSA-N 0.000 claims description 4
- SSVMIMPSMYTRIF-UHFFFAOYSA-N methyl 3-chloro-9H-carbazole-1-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C(C(=O)OC)=CC(Cl)=C2 SSVMIMPSMYTRIF-UHFFFAOYSA-N 0.000 claims description 4
- XFMOTEIBBVTYND-UHFFFAOYSA-N methyl 4-chloro-9H-carbazole-1-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C(C(=O)OC)=CC=C2Cl XFMOTEIBBVTYND-UHFFFAOYSA-N 0.000 claims description 4
- PKQBNCQFLKRJLY-UHFFFAOYSA-N methyl 4-methyl-9h-carbazole-1-carboxylate Chemical compound C12=CC=CC=C2NC2=C1C(C)=CC=C2C(=O)OC PKQBNCQFLKRJLY-UHFFFAOYSA-N 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- YZCKPIATAKJXRG-UHFFFAOYSA-N (7-chloro-8-methyl-9h-carbazol-1-yl)methanol Chemical compound N1C2=C(CO)C=CC=C2C2=C1C(C)=C(Cl)C=C2 YZCKPIATAKJXRG-UHFFFAOYSA-N 0.000 claims description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- CLJXERHFEVKSGU-UHFFFAOYSA-N ethyl 5-chloro-6-methyl-9H-carbazole-1-carboxylate Chemical compound N1C2=CC=C(C)C(Cl)=C2C2=C1C(C(=O)OCC)=CC=C2 CLJXERHFEVKSGU-UHFFFAOYSA-N 0.000 claims description 3
- JZPOPPJPVFOZKK-UHFFFAOYSA-N ethyl 5-chloro-8-methoxy-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=C(C=CC(=C3NC12)OC)Cl JZPOPPJPVFOZKK-UHFFFAOYSA-N 0.000 claims description 3
- UUZWYPMJBQFACW-UHFFFAOYSA-N ethyl 6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC(=CC=C3NC12)OC UUZWYPMJBQFACW-UHFFFAOYSA-N 0.000 claims description 3
- IJZYBDUAUIFWIC-UHFFFAOYSA-N ethyl 7,8-dichloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=C(C(=C3NC12)Cl)Cl IJZYBDUAUIFWIC-UHFFFAOYSA-N 0.000 claims description 3
- NCAFTQQSBUWCJT-UHFFFAOYSA-N ethyl 7,8-dichloro-9H-carbazole-1-carboxylate Chemical compound N1C2=C(Cl)C(Cl)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 NCAFTQQSBUWCJT-UHFFFAOYSA-N 0.000 claims description 3
- GLOZCCYBWSLPKY-UHFFFAOYSA-N ethyl 7,8-dimethyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=C(C(=C3NC12)C)C GLOZCCYBWSLPKY-UHFFFAOYSA-N 0.000 claims description 3
- CXTSOVZJZKJWLZ-UHFFFAOYSA-N ethyl 7-(trifluoromethyl)-9h-carbazole-1-carboxylate Chemical compound N1C2=CC(C(F)(F)F)=CC=C2C2=C1C(C(=O)OCC)=CC=C2 CXTSOVZJZKJWLZ-UHFFFAOYSA-N 0.000 claims description 3
- HGOCOFUBUZTOEO-UHFFFAOYSA-N ethyl 7-chloro-8,9-dimethylcarbazole-1-carboxylate Chemical compound C12=CC=C(Cl)C(C)=C2N(C)C2=C1C=CC=C2C(=O)OCC HGOCOFUBUZTOEO-UHFFFAOYSA-N 0.000 claims description 3
- HKJKSNKBCAWPNJ-UHFFFAOYSA-N ethyl 9-benzyl-7-chloro-8-methylcarbazole-1-carboxylate Chemical compound C1=2C(C(=O)OCC)=CC=CC=2C2=CC=C(Cl)C(C)=C2N1CC1=CC=CC=C1 HKJKSNKBCAWPNJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- KMINKHPSENILJV-UHFFFAOYSA-N methyl 3-methyl-9h-carbazole-1-carboxylate Chemical compound C12=CC=CC=C2NC2=C1C=C(C)C=C2C(=O)OC KMINKHPSENILJV-UHFFFAOYSA-N 0.000 claims description 3
- PUDMAJQCSLNLMV-UHFFFAOYSA-N (7,8-dimethyl-9h-carbazol-1-yl)-morpholin-4-ylmethanone Chemical compound CC=1C(C)=CC=C(C2=CC=C3)C=1NC2=C3C(=O)N1CCOCC1 PUDMAJQCSLNLMV-UHFFFAOYSA-N 0.000 claims description 2
- LJDRBWVMZVSRRO-UHFFFAOYSA-N (7-chloro-8-methyl-9h-carbazol-1-yl)methyl acetate Chemical compound N1C2=C(C)C(Cl)=CC=C2C2=C1C(COC(=O)C)=CC=C2 LJDRBWVMZVSRRO-UHFFFAOYSA-N 0.000 claims description 2
- HWFUOXYUSCPVDD-UHFFFAOYSA-N 11h-benzo[a]carbazole-1-carboxylic acid Chemical compound C1=CC=C2NC3=C4C(C(=O)O)=CC=CC4=CC=C3C2=C1 HWFUOXYUSCPVDD-UHFFFAOYSA-N 0.000 claims description 2
- YJHLQLKAWHVPFN-UHFFFAOYSA-N 2-chloro-1-methyl-8-(2h-tetrazol-5-yl)-9h-carbazole Chemical compound C=12NC=3C(C)=C(Cl)C=CC=3C2=CC=CC=1C1=NN=NN1 YJHLQLKAWHVPFN-UHFFFAOYSA-N 0.000 claims description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 2
- NFQNYVATLJFESI-UHFFFAOYSA-N 3-chloro-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C=C(Cl)C=C2C(=O)O NFQNYVATLJFESI-UHFFFAOYSA-N 0.000 claims description 2
- UFEJWHKHTXBYRR-UHFFFAOYSA-N 3-methyl-9h-carbazole-1-carboxylic acid Chemical compound C1=CC=C2C3=CC(C)=CC(C(O)=O)=C3NC2=C1 UFEJWHKHTXBYRR-UHFFFAOYSA-N 0.000 claims description 2
- HNGSBSQQQFSDAU-UHFFFAOYSA-N 3-methylbutyl 7,8-dichloro-9H-carbazole-1-carboxylate Chemical compound C12=CC=C(Cl)C(Cl)=C2NC2=C1C=CC=C2C(=O)OCCC(C)C HNGSBSQQQFSDAU-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- BDONUPILRUXTQK-UHFFFAOYSA-N 4-chloro-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C(Cl)=CC=C2C(=O)O BDONUPILRUXTQK-UHFFFAOYSA-N 0.000 claims description 2
- CTUYLXJHJXENKE-UHFFFAOYSA-N 4-methyl-9h-carbazole-1-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C(C(O)=O)=CC=C2C CTUYLXJHJXENKE-UHFFFAOYSA-N 0.000 claims description 2
- PNQQTITVOMWHRD-UHFFFAOYSA-N 5-chloro-6-methyl-9h-carbazole-1-carboxylic acid Chemical compound C1=CC=C2C3=C(Cl)C(C)=CC=C3NC2=C1C(O)=O PNQQTITVOMWHRD-UHFFFAOYSA-N 0.000 claims description 2
- KKMDIQCFUMVJBT-UHFFFAOYSA-N 5-chloro-8-methoxy-9h-carbazole-1-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C2=C1C(OC)=CC=C2Cl KKMDIQCFUMVJBT-UHFFFAOYSA-N 0.000 claims description 2
- VBBZJLRBMCHEAG-UHFFFAOYSA-N 5-chloro-8-methyl-9h-carbazole-1-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C2=C1C(C)=CC=C2Cl VBBZJLRBMCHEAG-UHFFFAOYSA-N 0.000 claims description 2
- YBBIZUZGZCWZBD-UHFFFAOYSA-N 6-fluoro-9h-carbazole-1-carboxylic acid Chemical compound C12=CC(F)=CC=C2NC2=C1C=CC=C2C(=O)O YBBIZUZGZCWZBD-UHFFFAOYSA-N 0.000 claims description 2
- JLYWFVVBYUCXPN-UHFFFAOYSA-N 6-methoxy-9h-carbazole-1-carboxylic acid Chemical compound C1=CC=C2C3=CC(OC)=CC=C3NC2=C1C(O)=O JLYWFVVBYUCXPN-UHFFFAOYSA-N 0.000 claims description 2
- XLKHCWYAJCDBLE-UHFFFAOYSA-N 7-chloro-3,8-dimethyl-9h-carbazole-1-carboxylic acid Chemical compound ClC1=CC=C2C3=CC(C)=CC(C(O)=O)=C3NC2=C1C XLKHCWYAJCDBLE-UHFFFAOYSA-N 0.000 claims description 2
- YZZSZXKFEBZAHK-UHFFFAOYSA-N 7-chloro-6-methyl-9h-carbazole-1-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C2=C1C=C(Cl)C(C)=C2 YZZSZXKFEBZAHK-UHFFFAOYSA-N 0.000 claims description 2
- KEYVZZLOAKGSDD-UHFFFAOYSA-N 7-chloro-8,9-dimethylcarbazole-1-carboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2N(C)C2=C1C=CC(Cl)=C2C KEYVZZLOAKGSDD-UHFFFAOYSA-N 0.000 claims description 2
- ALRRWAPRCLSXHX-UHFFFAOYSA-N 7-chloro-8-ethyl-9h-carbazole-1-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C2=C1C(CC)=C(Cl)C=C2 ALRRWAPRCLSXHX-UHFFFAOYSA-N 0.000 claims description 2
- WQQPYEUPONPTFU-UHFFFAOYSA-N 7-chloro-8-methyl-9h-carbazole-1-carbonyl chloride Chemical compound C12=CC=CC(C(Cl)=O)=C2NC2=C1C=CC(Cl)=C2C WQQPYEUPONPTFU-UHFFFAOYSA-N 0.000 claims description 2
- TWYDFZZEERAMEH-UHFFFAOYSA-N 7-chloro-n-hydroxy-8-methyl-9h-carbazole-1-carboxamide Chemical compound N1C2=C(C(=O)NO)C=CC=C2C2=C1C(C)=C(Cl)C=C2 TWYDFZZEERAMEH-UHFFFAOYSA-N 0.000 claims description 2
- ACECFVCGNPKSFD-UHFFFAOYSA-N 7-fluoro-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=C(F)C=C2NC2=C1C=CC=C2C(=O)O ACECFVCGNPKSFD-UHFFFAOYSA-N 0.000 claims description 2
- ZVTTYJFGXNURLR-UHFFFAOYSA-N 8-chloro-7-methyl-9h-carbazole-1-carboxylic acid Chemical compound C1=CC=C2C3=CC=C(C)C(Cl)=C3NC2=C1C(O)=O ZVTTYJFGXNURLR-UHFFFAOYSA-N 0.000 claims description 2
- MMFNREYLQKLTAN-UHFFFAOYSA-N 8-methoxy-9h-carbazole-1-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C2=C1C(OC)=CC=C2 MMFNREYLQKLTAN-UHFFFAOYSA-N 0.000 claims description 2
- NIEJYFQQHMRGHX-UHFFFAOYSA-N 8-methyl-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2NC2=C1C=CC=C2C NIEJYFQQHMRGHX-UHFFFAOYSA-N 0.000 claims description 2
- RLTIWWLNDYSJFX-UHFFFAOYSA-N 9-benzyl-7-chloro-8-methylcarbazole-1-carboxylic acid Chemical compound C1=2C(C)=C(Cl)C=CC=2C2=CC=CC(C(O)=O)=C2N1CC1=CC=CC=C1 RLTIWWLNDYSJFX-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 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 claims description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- URTVPXRFRXWSTG-UHFFFAOYSA-N ethyl 5-chloro-8-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=C(C=CC(=C3NC12)C)Cl URTVPXRFRXWSTG-UHFFFAOYSA-N 0.000 claims description 2
- NKFBFGUTZNPPJH-UHFFFAOYSA-N ethyl 6-fluoro-2,3,4,9-tetrahydro-1h-carbazole-1-carboxylate Chemical compound N1C2=CC=C(F)C=C2C2=C1C(C(=O)OCC)CCC2 NKFBFGUTZNPPJH-UHFFFAOYSA-N 0.000 claims description 2
- FOJPERZKPIUMTK-UHFFFAOYSA-N ethyl 6-fluoro-9H-carbazole-1-carboxylate Chemical compound N1C2=CC=C(F)C=C2C2=C1C(C(=O)OCC)=CC=C2 FOJPERZKPIUMTK-UHFFFAOYSA-N 0.000 claims description 2
- PHFXYUHXCNSTRG-UHFFFAOYSA-N ethyl 7-chloro-3,8-dimethyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CC(CC=2C3=CC=C(C(=C3NC12)C)Cl)C PHFXYUHXCNSTRG-UHFFFAOYSA-N 0.000 claims description 2
- LOJCPKIUNWUVBL-UHFFFAOYSA-N ethyl 7-chloro-6-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC(=C(C=C3NC12)Cl)C LOJCPKIUNWUVBL-UHFFFAOYSA-N 0.000 claims description 2
- PLEODTXOTPXFAP-UHFFFAOYSA-N ethyl 7-fluoro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=C(C=C3NC12)F PLEODTXOTPXFAP-UHFFFAOYSA-N 0.000 claims description 2
- YURKAGDJOIRLFK-UHFFFAOYSA-N ethyl 8-chloro-7-methyl-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=C(C(=C3NC12)Cl)C YURKAGDJOIRLFK-UHFFFAOYSA-N 0.000 claims description 2
- IMVOMWYKXZDVCE-UHFFFAOYSA-N ethyl 8-methoxy-2,3,4,9-tetrahydro-1H-carbazole-1-carboxylate Chemical compound C(C)OC(=O)C1CCCC=2C3=CC=CC(=C3NC12)OC IMVOMWYKXZDVCE-UHFFFAOYSA-N 0.000 claims description 2
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- YLBSTBPBIVGLIW-UHFFFAOYSA-N methyl 4-methyl-6,7,8,9-tetrahydro-5H-carbazole-1-carboxylate Chemical compound COC(=O)C1=CC=C(C=2C=3CCCCC3NC12)C YLBSTBPBIVGLIW-UHFFFAOYSA-N 0.000 claims description 2
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- VAQBJVZNPBNHGC-UHFFFAOYSA-N methyl 2-amino-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1N VAQBJVZNPBNHGC-UHFFFAOYSA-N 0.000 description 1
- XOGIKWSCTIFLGT-UHFFFAOYSA-N methyl 9h-carbazole-1-carboxylate Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(=O)OC XOGIKWSCTIFLGT-UHFFFAOYSA-N 0.000 description 1
- BLIJXOOIHRSQRB-PXYINDEMSA-N n-[(2s)-1-[3-(3-chloro-4-cyanophenyl)pyrazol-1-yl]propan-2-yl]-5-(1-hydroxyethyl)-1h-pyrazole-3-carboxamide Chemical compound C([C@H](C)NC(=O)C=1NN=C(C=1)C(C)O)N(N=1)C=CC=1C1=CC=C(C#N)C(Cl)=C1 BLIJXOOIHRSQRB-PXYINDEMSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000008027 tertiary esters Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2337154A DE2337154C2 (de) | 1973-07-18 | 1973-07-18 | Neue Carbazolderivate |
| DE2431292A DE2431292A1 (de) | 1974-06-27 | 1974-06-27 | Neue carbazol-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053682A true CA1053682A (en) | 1979-05-01 |
Family
ID=25765532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA205,063A Expired CA1053682A (en) | 1973-07-18 | 1974-07-18 | Carbazole derivatives and process for their manufacture |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5069072A (enExample) |
| AT (1) | AT342583B (enExample) |
| BG (1) | BG25793A3 (enExample) |
| CA (1) | CA1053682A (enExample) |
| CH (1) | CH619213A5 (enExample) |
| CS (1) | CS190431B2 (enExample) |
| DD (1) | DD114075A5 (enExample) |
| DK (1) | DK388074A (enExample) |
| ES (1) | ES428379A1 (enExample) |
| FI (1) | FI218874A7 (enExample) |
| FR (1) | FR2237628B1 (enExample) |
| GB (1) | GB1482771A (enExample) |
| HU (1) | HU173115B (enExample) |
| IE (1) | IE39624B1 (enExample) |
| IL (1) | IL45298A (enExample) |
| NL (1) | NL7409715A (enExample) |
| NO (1) | NO742601L (enExample) |
| RO (1) | RO72713A (enExample) |
| SE (1) | SE396602B (enExample) |
| SU (1) | SU511855A3 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8946444B2 (en) | 2004-11-23 | 2015-02-03 | Ptc Therapeutics, Inc. | Tetrahydrocarbazoles as active agents for inhibiting VEGF production by translational control |
| US10329254B2 (en) | 2011-10-20 | 2019-06-25 | Aop Orphan Pharmaceuticals Ag | Process for the preparation of 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide and intermediates thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ533430A (en) * | 2001-12-14 | 2005-12-23 | Zentaris Gmbh | Tetrahydrocarbozole derivatives as ligands for G-protein coupled receptors (GPCR) |
| EP1677794B1 (en) * | 2003-09-12 | 2014-12-03 | Elixir Pharmaceuticals, Inc. | Methods of treating disorder |
| US20060074124A1 (en) * | 2003-09-12 | 2006-04-06 | Andrew Napper | Methods of treating a disorder |
| US11655244B2 (en) * | 2017-04-11 | 2023-05-23 | Gsno Therapeutics, Inc. | Carbazole compounds and methods of use thereof |
| JP2021134141A (ja) * | 2020-02-21 | 2021-09-13 | エヌ・イーケムキャット株式会社 | 不均一系貴金属触媒を用いた芳香族化合物の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7008628A (enExample) * | 1969-06-25 | 1970-12-29 |
-
1974
- 1974-07-15 BG BG027244A patent/BG25793A3/xx unknown
- 1974-07-16 DD DD179943A patent/DD114075A5/xx unknown
- 1974-07-17 FI FI2188/74A patent/FI218874A7/fi unknown
- 1974-07-17 ES ES428379A patent/ES428379A1/es not_active Expired
- 1974-07-17 NO NO742601A patent/NO742601L/no unknown
- 1974-07-17 CS CS745109A patent/CS190431B2/cs unknown
- 1974-07-17 SE SE7409330A patent/SE396602B/xx unknown
- 1974-07-17 HU HU24SC483A patent/HU173115B/hu unknown
- 1974-07-18 RO RO7479524A patent/RO72713A/ro unknown
- 1974-07-18 DK DK388074A patent/DK388074A/da not_active Application Discontinuation
- 1974-07-18 IL IL45298A patent/IL45298A/xx unknown
- 1974-07-18 SU SU2048652A patent/SU511855A3/ru active
- 1974-07-18 CA CA205,063A patent/CA1053682A/en not_active Expired
- 1974-07-18 GB GB31966/74A patent/GB1482771A/en not_active Expired
- 1974-07-18 FR FR7424991A patent/FR2237628B1/fr not_active Expired
- 1974-07-18 AT AT596074A patent/AT342583B/de active
- 1974-07-18 NL NL7409715A patent/NL7409715A/xx not_active Application Discontinuation
- 1974-07-18 IE IE1519/74A patent/IE39624B1/xx unknown
- 1974-07-18 JP JP49082669A patent/JPS5069072A/ja active Pending
- 1974-07-18 CH CH990174A patent/CH619213A5/de not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8946444B2 (en) | 2004-11-23 | 2015-02-03 | Ptc Therapeutics, Inc. | Tetrahydrocarbazoles as active agents for inhibiting VEGF production by translational control |
| US10329254B2 (en) | 2011-10-20 | 2019-06-25 | Aop Orphan Pharmaceuticals Ag | Process for the preparation of 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide and intermediates thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CH619213A5 (en) | 1980-09-15 |
| NO742601L (enExample) | 1975-02-17 |
| GB1482771A (en) | 1977-08-17 |
| BG25793A3 (bg) | 1978-12-12 |
| SE396602B (sv) | 1977-09-26 |
| JPS5069072A (enExample) | 1975-06-09 |
| NL7409715A (nl) | 1975-01-21 |
| AT342583B (de) | 1978-04-10 |
| DD114075A5 (enExample) | 1975-07-12 |
| FR2237628A1 (enExample) | 1975-02-14 |
| IE39624B1 (en) | 1978-11-22 |
| SU511855A3 (ru) | 1976-04-25 |
| ATA596074A (de) | 1977-08-15 |
| IL45298A0 (en) | 1974-10-22 |
| HU173115B (hu) | 1979-02-28 |
| DK388074A (enExample) | 1975-03-03 |
| IL45298A (en) | 1980-01-31 |
| CS190431B2 (en) | 1979-05-31 |
| IE39624L (en) | 1975-01-18 |
| ES428379A1 (es) | 1976-09-16 |
| SE7409330L (enExample) | 1975-01-20 |
| FI218874A7 (enExample) | 1975-01-19 |
| RO72713A (ro) | 1982-09-09 |
| FR2237628B1 (enExample) | 1977-05-20 |
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