SU509220A3 - Способ получени производныхкарбазола или их опти-ческих изомеров,или их солей - Google Patents
Способ получени производныхкарбазола или их опти-ческих изомеров,или их солейInfo
- Publication number
- SU509220A3 SU509220A3 SU1950151A SU1950151A SU509220A3 SU 509220 A3 SU509220 A3 SU 509220A3 SU 1950151 A SU1950151 A SU 1950151A SU 1950151 A SU1950151 A SU 1950151A SU 509220 A3 SU509220 A3 SU 509220A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acetic acid
- chloro
- solution
- tetrahydrocarbazole
- ethyl ester
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 11
- 238000000034 method Methods 0.000 title description 10
- 230000003287 optical effect Effects 0.000 title description 4
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 97
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 94
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 60
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000009835 boiling Methods 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 238000001914 filtration Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 239000002274 desiccant Substances 0.000 description 13
- -1 N-dimethylsulfamoyl carbazole-2-acetic acid ethyl ester Chemical compound 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 11
- 125000004494 ethyl ester group Chemical group 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 208000006278 hypochromic anemia Diseases 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NCNIENBPIQCVRO-UHFFFAOYSA-N 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)propanedioic acid Chemical compound ClC=1C=C2C=3CCCC(C3NC2=CC1)C(C(=O)O)C(=O)O NCNIENBPIQCVRO-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GFYFVBMSCDUTPE-UHFFFAOYSA-N 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)acetic acid Chemical compound ClC=1C=C2C=3CCCC(C3NC2=CC1)CC(=O)O GFYFVBMSCDUTPE-UHFFFAOYSA-N 0.000 description 2
- FEZREFUXTTXJPS-UHFFFAOYSA-N 2-(7-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid Chemical compound ClC1=CC=C2C=3CCC(CC3NC2=C1)CC(=O)O FEZREFUXTTXJPS-UHFFFAOYSA-N 0.000 description 2
- IJBOXSZHXVEMGE-UHFFFAOYSA-N 2-(9-benzyl-6-methylcarbazol-1-yl)acetic acid Chemical compound CC=1C=C2C=3C=CC=C(C3N(C2=CC1)CC1=CC=CC=C1)CC(=O)O IJBOXSZHXVEMGE-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- ZWPWQNFDBJPYHB-UHFFFAOYSA-N 2-(2,3,4,9-tetrahydro-1h-carbazol-2-yl)acetic acid Chemical compound N1C2=CC=CC=C2C2=C1CC(CC(=O)O)CC2 ZWPWQNFDBJPYHB-UHFFFAOYSA-N 0.000 description 1
- SXRWFAZQJZXAKA-UHFFFAOYSA-N 2-(5,6-dichloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid Chemical compound ClC1=C2C=3CCC(CC3NC2=CC=C1Cl)CC(=O)O SXRWFAZQJZXAKA-UHFFFAOYSA-N 0.000 description 1
- OVXWGNHJMHFOKL-UHFFFAOYSA-N 2-(6-acetamido-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid Chemical compound C(C)(=O)NC=1C=C2C=3CCC(CC3NC2=CC1)CC(=O)O OVXWGNHJMHFOKL-UHFFFAOYSA-N 0.000 description 1
- UIUNPBLAXOCPDZ-UHFFFAOYSA-N 2-(6-bromo-9h-carbazol-2-yl)acetic acid Chemical compound C1=C(Br)C=C2C3=CC=C(CC(=O)O)C=C3NC2=C1 UIUNPBLAXOCPDZ-UHFFFAOYSA-N 0.000 description 1
- TUHDSRIQSRCZEN-UHFFFAOYSA-N 2-(6-chloro-1-methyl-9H-carbazol-2-yl)acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C2=C1C(C)=C(CC(O)=O)C=C2 TUHDSRIQSRCZEN-UHFFFAOYSA-N 0.000 description 1
- DRXOVDJYKJTSJJ-UHFFFAOYSA-N 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-4-yl)acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C2=C1CCCC2CC(=O)O DRXOVDJYKJTSJJ-UHFFFAOYSA-N 0.000 description 1
- PZJKRCQOBPSLCF-UHFFFAOYSA-N 2-(6-chloro-9-methylcarbazol-1-yl)acetic acid Chemical compound ClC=1C=C2C=3C=CC=C(C3N(C2=CC1)C)CC(=O)O PZJKRCQOBPSLCF-UHFFFAOYSA-N 0.000 description 1
- VECSVKNSAACGIB-UHFFFAOYSA-N 2-(6-chloro-9H-carbazol-1-yl)acetic acid Chemical compound ClC=1C=C2C=3C=CC=C(C3NC2=CC1)CC(=O)O VECSVKNSAACGIB-UHFFFAOYSA-N 0.000 description 1
- AFEQRIPACHJICQ-UHFFFAOYSA-N 2-(6-cyano-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid Chemical compound C(#N)C=1C=C2C=3CCC(CC3NC2=CC1)CC(=O)O AFEQRIPACHJICQ-UHFFFAOYSA-N 0.000 description 1
- XNPJDOFRBWXAEM-UHFFFAOYSA-N 2-(6-methoxy-9H-carbazol-2-yl)acetic acid Chemical compound COC=1C=C2C=3C=CC(=CC3NC2=CC1)CC(=O)O XNPJDOFRBWXAEM-UHFFFAOYSA-N 0.000 description 1
- MGGZVPDGWMOSRR-UHFFFAOYSA-N 2-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid Chemical compound CC=1C=C2C=3CCC(CC3NC2=CC1)CC(=O)O MGGZVPDGWMOSRR-UHFFFAOYSA-N 0.000 description 1
- XVIUJYDGUZGBTR-UHFFFAOYSA-N 2-(6-methyl-9H-carbazol-2-yl)acetic acid Chemical compound CC=1C=C2C=3C=CC(=CC3NC2=CC1)CC(=O)O XVIUJYDGUZGBTR-UHFFFAOYSA-N 0.000 description 1
- ZHLYCWPDXFIFKD-UHFFFAOYSA-N 2-(6-methylsulfanyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid Chemical compound CSC=1C=C2C=3CCC(CC3NC2=CC1)CC(=O)O ZHLYCWPDXFIFKD-UHFFFAOYSA-N 0.000 description 1
- GWBRKPAHRXGXKQ-UHFFFAOYSA-N 2-(7,8-dichloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid Chemical compound ClC1=CC=C2C=3CCC(CC3NC2=C1Cl)CC(=O)O GWBRKPAHRXGXKQ-UHFFFAOYSA-N 0.000 description 1
- DMCQBDWRSFYWAV-UHFFFAOYSA-N 2-(7-chloro-9H-carbazol-2-yl)acetic acid Chemical compound ClC1=CC=C2C=3C=CC(=CC3NC2=C1)CC(=O)O DMCQBDWRSFYWAV-UHFFFAOYSA-N 0.000 description 1
- ODGAQUIHAIDCMY-UHFFFAOYSA-N 2-(7-chloro-9H-carbazol-3-yl)acetic acid Chemical compound ClC1=CC=C2C=3C=C(C=CC3NC2=C1)CC(=O)O ODGAQUIHAIDCMY-UHFFFAOYSA-N 0.000 description 1
- MKBOCLLAJIIVAL-UHFFFAOYSA-N 2-(7-methyl-9H-carbazol-2-yl)acetic acid Chemical compound CC1=CC=C2C=3C=CC(=CC=3NC2=C1)CC(=O)O MKBOCLLAJIIVAL-UHFFFAOYSA-N 0.000 description 1
- WBZURBKQPPPXNS-UHFFFAOYSA-N 2-(8-chloro-9H-carbazol-2-yl)acetic acid Chemical compound ClC=1C=CC=C2C=3C=CC(=CC3NC12)CC(=O)O WBZURBKQPPPXNS-UHFFFAOYSA-N 0.000 description 1
- DUKICBKKKXQDJY-UHFFFAOYSA-N 2-[6-(dimethylsulfamoyl)-2,3,4,9-tetrahydro-1H-carbazol-2-yl]acetic acid Chemical compound CN(S(=O)(=O)C=1C=C2C=3CCC(CC3NC2=CC1)CC(=O)O)C DUKICBKKKXQDJY-UHFFFAOYSA-N 0.000 description 1
- XZMMLSPXNHWGGX-UHFFFAOYSA-N 2-[6-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-2-yl]acetic acid Chemical compound FC(C=1C=C2C=3CCC(CC3NC2=CC1)CC(=O)O)(F)F XZMMLSPXNHWGGX-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- CUSIEVUKVHPVTE-UHFFFAOYSA-N 3-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoic acid Chemical compound ClC=1C=C2C=3CCC(CC3NC2=CC1)CCC(=O)O CUSIEVUKVHPVTE-UHFFFAOYSA-N 0.000 description 1
- XBEFUQXZJDZZQD-UHFFFAOYSA-N 3-(6-chloro-9H-carbazol-2-yl)propanoic acid Chemical compound ClC=1C=C2C=3C=CC(=CC3NC2=CC1)CCC(=O)O XBEFUQXZJDZZQD-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- VBOVPBWWJQJAOI-UHFFFAOYSA-N C1CC2=C(CC1CC(=O)O)N(C3=CC=CC=C23)Cl Chemical compound C1CC2=C(CC1CC(=O)O)N(C3=CC=CC=C23)Cl VBOVPBWWJQJAOI-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- PUXBGTOOZJQSKH-UHFFFAOYSA-N carprofen Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3NC2=C1 PUXBGTOOZJQSKH-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- PNNZBNYYPRTVBN-UHFFFAOYSA-N ethyl 2-(5,6-dichloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C(=C3C2C=C1)Cl)Cl)=O PNNZBNYYPRTVBN-UHFFFAOYSA-N 0.000 description 1
- NDARIKRJTTYROX-UHFFFAOYSA-N ethyl 2-(6,7-dichloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC(=C(C=C3C2C=C1)Cl)Cl)=O NDARIKRJTTYROX-UHFFFAOYSA-N 0.000 description 1
- KKVNTGIFSMRFAM-UHFFFAOYSA-N ethyl 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1CC=2NC3=CC=C(C=C3C2CC1)Cl)=O KKVNTGIFSMRFAM-UHFFFAOYSA-N 0.000 description 1
- HAGBBNHRZNDPGE-UHFFFAOYSA-N ethyl 2-(6-chloro-9H-carbazol-4-yl)acetate Chemical compound C(C)OC(CC1=CC=CC=2NC3=CC=C(C=C3C12)Cl)=O HAGBBNHRZNDPGE-UHFFFAOYSA-N 0.000 description 1
- SXSQXLKLMHIBPE-UHFFFAOYSA-N ethyl 2-(6-cyano-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)C#N)=O SXSQXLKLMHIBPE-UHFFFAOYSA-N 0.000 description 1
- VULGDWQHPOBIPO-UHFFFAOYSA-N ethyl 2-(6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1CC=2NC3=CC=C(C=C3C2CC1)F)=O VULGDWQHPOBIPO-UHFFFAOYSA-N 0.000 description 1
- ATCCCCVLVQZQFP-UHFFFAOYSA-N ethyl 2-(6-fluoro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)F)=O ATCCCCVLVQZQFP-UHFFFAOYSA-N 0.000 description 1
- UUALWKOQULOGBX-UHFFFAOYSA-N ethyl 2-(6-methylsulfanyl-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)SC)=O UUALWKOQULOGBX-UHFFFAOYSA-N 0.000 description 1
- WAWHBEPXRFDTLT-UHFFFAOYSA-N ethyl 2-(6-nitro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)[N+](=O)[O-])=O WAWHBEPXRFDTLT-UHFFFAOYSA-N 0.000 description 1
- IXBCZRPIQPGDAX-UHFFFAOYSA-N ethyl 2-(7,8-dichloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=C(C(=CC=C3C2C=C1)Cl)Cl)=O IXBCZRPIQPGDAX-UHFFFAOYSA-N 0.000 description 1
- KVMSBFRUOJCOQM-UHFFFAOYSA-N ethyl 3-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoate Chemical compound C(C)OC(CCC1CC=2NC3=CC=C(C=C3C2CC1)Cl)=O KVMSBFRUOJCOQM-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- JWFQIJOWFMAEMA-UHFFFAOYSA-N n-(9h-carbazol-3-yl)acetamide Chemical compound C1=CC=C2C3=CC(NC(=O)C)=CC=C3NC2=C1 JWFQIJOWFMAEMA-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27414272A | 1972-07-24 | 1972-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU509220A3 true SU509220A3 (ru) | 1976-03-30 |
Family
ID=23046965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1950151A SU509220A3 (ru) | 1972-07-24 | 1973-07-24 | Способ получени производныхкарбазола или их опти-ческих изомеров,или их солей |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5740144B2 (enExample) |
| KR (1) | KR780000289B1 (enExample) |
| AR (1) | AR205331A1 (enExample) |
| AT (1) | AT325607B (enExample) |
| AU (1) | AU475534B2 (enExample) |
| BE (1) | BE802596A (enExample) |
| CA (1) | CA1026348A (enExample) |
| CH (1) | CH587819A5 (enExample) |
| DD (1) | DD107681A5 (enExample) |
| DE (1) | DE2337340C2 (enExample) |
| DK (1) | DK138537B (enExample) |
| FI (1) | FI59244C (enExample) |
| FR (1) | FR2193611B1 (enExample) |
| GB (1) | GB1385620A (enExample) |
| HK (1) | HK49878A (enExample) |
| HU (1) | HU167611B (enExample) |
| IE (1) | IE37942B1 (enExample) |
| IL (1) | IL42799A (enExample) |
| KE (1) | KE2847A (enExample) |
| LU (1) | LU68071A1 (enExample) |
| MY (1) | MY7800315A (enExample) |
| NL (1) | NL169877C (enExample) |
| NO (1) | NO142865C (enExample) |
| SE (2) | SE402283B (enExample) |
| SU (1) | SU509220A3 (enExample) |
| ZA (1) | ZA734047B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2624446C2 (ru) * | 2011-11-15 | 2017-07-04 | Йиссум Ресерч Девелопмент Компани оф де Хебрю Юниверсити оф Джерусалем Лтд. | Трициклические соединения, композиции, содержащие указанные соединения, и их применения |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146542A (en) * | 1978-06-12 | 1979-03-27 | Hoffmann-La Roche Inc. | Dihydrocarbazole acetic acid and esters thereof |
| US4150031A (en) * | 1978-06-26 | 1979-04-17 | Hoffmann-La Roche Inc. | Hydroxy methyl carbazole acetic acid and esters |
| US4158007A (en) * | 1978-08-21 | 1979-06-12 | Hoffmann-La Roche Inc. | Carbazole methyl malonates |
| US4501908A (en) * | 1981-03-12 | 1985-02-26 | Hoffmann-La Roche Inc. | 2,3-Isopropylidene ribonic acid, 1,4-lactones |
| JPS6040256U (ja) * | 1983-08-25 | 1985-03-20 | 伊東 璋 | 容器類洗浄機 |
| DE3768097D1 (de) * | 1986-01-23 | 1991-04-04 | Merck Frosst Canada Inc | Tetrahydrocarbazol-1-alkansaeuren. |
| ATE90076T1 (de) | 1986-03-27 | 1993-06-15 | Merck Frosst Canada Inc | Tetrahydrocarbazole ester. |
| CA1326030C (en) * | 1987-07-21 | 1994-01-11 | John W. Gillard | Cyclohept[b]indolealkanoic acids |
| EP0307077A1 (en) * | 1987-07-21 | 1989-03-15 | Merck Frosst Canada Inc. | Tetrahydrocarbazoles for the improvement of cyclosporin therapy |
| PT95692A (pt) * | 1989-10-27 | 1991-09-13 | American Home Prod | Processo para a preparacao de derivados de acidos indole-,indeno-,piranoindole- e tetra-hidrocarbazole-alcanoicos, ou quais sao uteis como inibidores de pla2 e da lipoxigenase |
| US6013808A (en) * | 1998-06-16 | 2000-01-11 | Pfizer Inc. | Method of purifying carbazole ester precursors of 6-chloro-α-methyl-carbazole-2-acetic acid |
| JP2004010601A (ja) * | 2002-06-11 | 2004-01-15 | Nippon Steel Chem Co Ltd | インドール誘導体の製造方法及びそのための有用な中間体 |
| JP2006517925A (ja) * | 2003-01-14 | 2006-08-03 | メルク エンド カムパニー インコーポレーテッド | Ａβ４２低下薬としてのジェミナル二置換ＮＳＡＩＤ誘導体 |
| WO2005000457A2 (en) * | 2003-05-06 | 2005-01-06 | Air Products And Chemicals, Inc. | Hydrogen storage reversible hydrogenated of pi-conjugated substrates |
| CA2535497A1 (en) * | 2003-08-15 | 2005-02-24 | Universite Laval | Monomers, oligomers and polymers of 2-functionalized and 2,7-difunctionalized carbazoles |
| US7601856B2 (en) | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| US7662831B2 (en) | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
| JP5940036B2 (ja) * | 2013-10-08 | 2016-06-29 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
| JP7747621B2 (ja) * | 2020-03-25 | 2025-10-01 | Jnc株式会社 | 化合物、液晶組成物および液晶表示素子 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD70880A (enExample) * | ||||
| US3580926A (en) * | 1969-11-10 | 1971-05-25 | Parke Davis & Co | Carbazole-4-alkanoic acids and tetrahydrocarbazole-4-alkanoic acids |
| ZA715217B (en) * | 1970-08-20 | 1972-04-26 | Org Nv | Anti-inflammatory preparations |
-
1973
- 1973-01-01 AR AR249230A patent/AR205331A1/es active
- 1973-06-14 ZA ZA734047A patent/ZA734047B/xx unknown
- 1973-06-15 CH CH871673A patent/CH587819A5/xx not_active IP Right Cessation
- 1973-07-20 IL IL42799A patent/IL42799A/en unknown
- 1973-07-20 HU HUHO1597A patent/HU167611B/hu unknown
- 1973-07-20 BE BE133691A patent/BE802596A/xx not_active IP Right Cessation
- 1973-07-20 KR KR7301174A patent/KR780000289B1/ko not_active Expired
- 1973-07-23 AU AU58390/73A patent/AU475534B2/en not_active Expired
- 1973-07-23 GB GB3496873A patent/GB1385620A/en not_active Expired
- 1973-07-23 CA CA177,061A patent/CA1026348A/en not_active Expired
- 1973-07-23 DE DE2337340A patent/DE2337340C2/de not_active Expired
- 1973-07-23 DK DK405973AA patent/DK138537B/da not_active IP Right Cessation
- 1973-07-23 LU LU68071A patent/LU68071A1/xx unknown
- 1973-07-23 SE SE7310244A patent/SE402283B/xx unknown
- 1973-07-23 JP JP48081008A patent/JPS5740144B2/ja not_active Expired
- 1973-07-23 AT AT649773A patent/AT325607B/de not_active IP Right Cessation
- 1973-07-23 DD DD172456A patent/DD107681A5/xx unknown
- 1973-07-23 FI FI2311/73A patent/FI59244C/fi active
- 1973-07-23 IE IE1252/73A patent/IE37942B1/xx unknown
- 1973-07-23 NO NO2975/73A patent/NO142865C/no unknown
- 1973-07-24 NL NLAANVRAGE7310275,A patent/NL169877C/xx not_active IP Right Cessation
- 1973-07-24 SU SU1950151A patent/SU509220A3/ru active
- 1973-07-24 FR FR7327020A patent/FR2193611B1/fr not_active Expired
-
1976
- 1976-05-21 SE SE7605813A patent/SE7605813L/xx unknown
-
1978
- 1978-06-13 KE KE2847A patent/KE2847A/xx unknown
- 1978-08-31 HK HK498/78A patent/HK49878A/xx unknown
- 1978-12-30 MY MY315/78A patent/MY7800315A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2624446C2 (ru) * | 2011-11-15 | 2017-07-04 | Йиссум Ресерч Девелопмент Компани оф де Хебрю Юниверсити оф Джерусалем Лтд. | Трициклические соединения, композиции, содержащие указанные соединения, и их применения |
| RU2624446C9 (ru) * | 2011-11-15 | 2018-04-04 | Йиссум Ресерч Девелопмент Компани оф де Хебрю Юниверсити оф Джерусалем Лтд. | Трициклические соединения, композиции, содержащие указанные соединения, и их применения |
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