FI59244C - Foerfarande foer framstaellning av farmaceutiskt anvaendbara karbazoler - Google Patents
Foerfarande foer framstaellning av farmaceutiskt anvaendbara karbazoler Download PDFInfo
- Publication number
- FI59244C FI59244C FI2311/73A FI231173A FI59244C FI 59244 C FI59244 C FI 59244C FI 2311/73 A FI2311/73 A FI 2311/73A FI 231173 A FI231173 A FI 231173A FI 59244 C FI59244 C FI 59244C
- Authority
- FI
- Finland
- Prior art keywords
- acetic acid
- formula
- group
- chloro
- ethyl ester
- Prior art date
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- 238000009313 farming Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 26
- -1 cyano, methyl Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- QLQIYGDZYYQKGS-UHFFFAOYSA-N 2-(6-chloro-9h-carbazol-2-yl)propan-1-ol Chemical compound C1=C(Cl)C=C2C3=CC=C(C(CO)C)C=C3NC2=C1 QLQIYGDZYYQKGS-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- DHHFGQADZVYGIE-UHFFFAOYSA-N 9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(=O)O DHHFGQADZVYGIE-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000002274 desiccant Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 239000002585 base Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ONAAMJUFSFQSSD-UHFFFAOYSA-N 2-(6-chloro-9h-carbazol-2-yl)acetic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)O)C=C3NC2=C1 ONAAMJUFSFQSSD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- PUXBGTOOZJQSKH-UHFFFAOYSA-N carprofen Chemical class C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3NC2=C1 PUXBGTOOZJQSKH-UHFFFAOYSA-N 0.000 description 4
- 229940106681 chloroacetic acid Drugs 0.000 description 4
- RDNXGCFGFSARFQ-UHFFFAOYSA-N ethyl 2-(6-chloro-9h-carbazol-2-yl)propanoate Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C)C(=O)OCC)C=C3NC2=C1 RDNXGCFGFSARFQ-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 3
- DFSWZPYSQPYVDA-UHFFFAOYSA-N 2-(6-methylsulfanyl-9H-carbazol-2-yl)acetic acid Chemical compound CSC=1C=C2C=3C=CC(=CC3NC2=CC1)CC(=O)O DFSWZPYSQPYVDA-UHFFFAOYSA-N 0.000 description 3
- ZEGDKCCJFIJLFX-UHFFFAOYSA-N 2-(6-nitro-9H-carbazol-2-yl)acetic acid Chemical compound [N+](=O)([O-])C=1C=C2C=3C=CC(=CC3NC2=CC1)CC(=O)O ZEGDKCCJFIJLFX-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- SRIYKRNMEBAUGE-UHFFFAOYSA-N ethyl 2-(6-chloro-9-methylcarbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2N(C3=CC=C(C=C3C2C=C1)Cl)C)=O SRIYKRNMEBAUGE-UHFFFAOYSA-N 0.000 description 3
- HYYTZURTTBOOPV-UHFFFAOYSA-N ethyl 2-(6-chloro-9H-carbazol-1-yl)acetate Chemical compound C(C)OC(CC1=CC=CC=2C3=CC(=CC=C3NC12)Cl)=O HYYTZURTTBOOPV-UHFFFAOYSA-N 0.000 description 3
- SIHRKOZKOVXKFN-UHFFFAOYSA-N ethyl 2-(6-chloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)Cl)=O SIHRKOZKOVXKFN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- VGVYUQRMNJWFEF-UHFFFAOYSA-N ethyl 3-(6-chloro-9H-carbazol-2-yl)propanoate Chemical compound C(C)OC(CCC1=CC=2NC3=CC=C(C=C3C2C=C1)Cl)=O VGVYUQRMNJWFEF-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 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 2
- QWWIOCUFMXOEJX-UHFFFAOYSA-N 2-(6-chloro-9-methylcarbazol-2-yl)acetic acid Chemical compound C1=C(CC(O)=O)C=C2N(C)C3=CC=C(Cl)C=C3C2=C1 QWWIOCUFMXOEJX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- TVFXKUFKUMERQL-UHFFFAOYSA-N 2-(6-chloro-9H-carbazol-3-yl)acetic acid Chemical compound ClC=1C=C2C=3C=C(C=CC3NC2=CC1)CC(=O)O TVFXKUFKUMERQL-UHFFFAOYSA-N 0.000 description 2
- UQKWORPVDCKAAS-UHFFFAOYSA-N 2-(6-cyano-9H-carbazol-1-yl)acetic acid Chemical compound C(#N)C=1C=C2C=3C=CC=C(C=3NC2=CC=1)CC(=O)O UQKWORPVDCKAAS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 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
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- OMUDRBIMNYYPLG-UHFFFAOYSA-N ethyl 2-(6-chloro-9-ethylcarbazol-1-yl)acetate Chemical compound C(C)OC(CC1=CC=CC=2C3=CC(=CC=C3N(C12)CC)Cl)=O OMUDRBIMNYYPLG-UHFFFAOYSA-N 0.000 description 2
- ZZVOMYYTDHHVOW-UHFFFAOYSA-N ethyl 2-(6-chloro-9H-carbazol-3-yl)acetate Chemical compound C(C)OC(CC=1C=CC=2NC3=CC=C(C=C3C2C1)Cl)=O ZZVOMYYTDHHVOW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PFWOCVIKINICHM-UHFFFAOYSA-N ethyl 2-(6-methyl-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)C)=O PFWOCVIKINICHM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NEYIEHVTWMKNCP-UHFFFAOYSA-N ethyl 2-(7-chloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC(=CC=C3C2C=C1)Cl)=O NEYIEHVTWMKNCP-UHFFFAOYSA-N 0.000 description 2
- VPQFGSDQRACDFA-UHFFFAOYSA-N ethyl 2-(8-chloro-9H-carbazol-2-yl)acetate Chemical compound C(C)OC(CC1=CC=2NC3=C(C=CC=C3C2C=C1)Cl)=O VPQFGSDQRACDFA-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYTAOCNPRURRJX-UHFFFAOYSA-N 1-(6-chloro-9H-carbazol-2-yl)propan-1-ol Chemical compound ClC=1C=C2C=3C=CC(=CC=3NC2=CC=1)C(CC)O RYTAOCNPRURRJX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GAUCLTKRDDJSNT-UHFFFAOYSA-N 2-(5,6-dichloro-9H-carbazol-1-yl)acetic acid Chemical compound ClC1=C2C=3C=CC=C(C=3NC2=CC=C1Cl)CC(=O)O GAUCLTKRDDJSNT-UHFFFAOYSA-N 0.000 description 1
- KKAGKMNPGJQILN-UHFFFAOYSA-N 2-(5,6-dichloro-9H-carbazol-2-yl)acetic acid Chemical compound ClC1=C2C=3C=CC(=CC=3NC2=CC=C1Cl)CC(=O)O KKAGKMNPGJQILN-UHFFFAOYSA-N 0.000 description 1
- WCOVWCBQMPSUSX-UHFFFAOYSA-N 2-(5,6-dichloro-9H-carbazol-4-yl)acetic acid Chemical compound ClC1=C2C=3C(=CC=CC=3NC2=CC=C1Cl)CC(=O)O WCOVWCBQMPSUSX-UHFFFAOYSA-N 0.000 description 1
- ABBVLHPOTNWDRH-UHFFFAOYSA-N 2-(6,7-dichloro-9H-carbazol-1-yl)acetic acid Chemical compound ClC=1C=C2C=3C=CC=C(C=3NC2=CC=1Cl)CC(=O)O ABBVLHPOTNWDRH-UHFFFAOYSA-N 0.000 description 1
- CBFCJKYBNRNNTG-UHFFFAOYSA-N 2-(6-bromo-9H-carbazol-3-yl)acetic acid Chemical compound BrC=1C=C2C=3C=C(C=CC=3NC2=CC=1)CC(=O)O CBFCJKYBNRNNTG-UHFFFAOYSA-N 0.000 description 1
- QEVPXORQKSOSAH-UHFFFAOYSA-N 2-(6-chloro-5-methyl-9H-carbazol-1-yl)acetic acid Chemical compound ClC=1C(=C2C=3C=CC=C(C=3NC2=CC=1)CC(=O)O)C QEVPXORQKSOSAH-UHFFFAOYSA-N 0.000 description 1
- RQLSRBZDPWFIOC-UHFFFAOYSA-N 2-(6-chloro-5-methyl-9H-carbazol-3-yl)acetic acid Chemical compound ClC=1C(=C2C=3C=C(C=CC=3NC2=CC=1)CC(=O)O)C RQLSRBZDPWFIOC-UHFFFAOYSA-N 0.000 description 1
- OBKLFPODFZAWKH-UHFFFAOYSA-N 2-(6-chloro-5-methyl-9H-carbazol-4-yl)acetic acid Chemical compound ClC=1C(=C2C=3C(=CC=CC=3NC2=CC=1)CC(=O)O)C OBKLFPODFZAWKH-UHFFFAOYSA-N 0.000 description 1
- XMIBONDJDVWDMI-UHFFFAOYSA-N 2-(6-chloro-7-methyl-9H-carbazol-2-yl)acetic acid Chemical compound ClC=1C=C2C=3C=CC(=CC=3NC2=CC=1C)CC(=O)O XMIBONDJDVWDMI-UHFFFAOYSA-N 0.000 description 1
- HNTNUHAUTVSOMS-UHFFFAOYSA-N 2-(6-chloro-7-methyl-9H-carbazol-3-yl)acetic acid Chemical compound ClC=1C=C2C=3C=C(C=CC=3NC2=CC=1C)CC(=O)O HNTNUHAUTVSOMS-UHFFFAOYSA-N 0.000 description 1
- WGRFHQKPKSJYIF-UHFFFAOYSA-N 2-(6-chloro-9-ethylcarbazol-1-yl)acetic acid Chemical compound ClC=1C=C2C=3C=CC=C(C3N(C2=CC1)CC)CC(=O)O WGRFHQKPKSJYIF-UHFFFAOYSA-N 0.000 description 1
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- FTHNDIAQRKCWOQ-UHFFFAOYSA-N ethyl 2-[6-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-2-yl]acetate Chemical compound C(C)OC(CC1CC=2NC3=CC=C(C=C3C2CC1)C(F)(F)F)=O FTHNDIAQRKCWOQ-UHFFFAOYSA-N 0.000 description 1
- OHOWRNQSFTYJSK-UHFFFAOYSA-N ethyl 2-[6-(trifluoromethyl)-9H-carbazol-2-yl]acetate Chemical compound C(C)OC(CC1=CC=2NC3=CC=C(C=C3C2C=C1)C(F)(F)F)=O OHOWRNQSFTYJSK-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WGOODRXOEIQMQN-UHFFFAOYSA-N methyl 2-(6-chloro-9h-carbazol-2-yl)propanoate Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C)C(=O)OC)C=C3NC2=C1 WGOODRXOEIQMQN-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- ZBUQPAJRQXISTC-UHFFFAOYSA-N n-(chloromethyl)-n-ethylethanamine Chemical compound CCN(CC)CCl ZBUQPAJRQXISTC-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 101150072073 rfng gene Proteins 0.000 description 1
- 238000000926 separation method 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 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)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27414272A | 1972-07-24 | 1972-07-24 | |
| US27414272 | 1972-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI59244B FI59244B (fi) | 1981-03-31 |
| FI59244C true FI59244C (fi) | 1981-07-10 |
Family
ID=23046965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2311/73A FI59244C (fi) | 1972-07-24 | 1973-07-23 | Foerfarande foer framstaellning av farmaceutiskt anvaendbara karbazoler |
Country Status (26)
Families Citing this family (20)
| 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. |
| EP0307077A1 (en) * | 1987-07-21 | 1989-03-15 | Merck Frosst Canada Inc. | Tetrahydrocarbazoles for the improvement of cyclosporin therapy |
| CA1326030C (en) * | 1987-07-21 | 1994-01-11 | John W. Gillard | Cyclohept[b]indolealkanoic acids |
| 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 |
| US7332516B2 (en) | 2003-01-14 | 2008-02-19 | Merck + Co., Inc. | Geminally di-substituted NSAID derivatives as Aβ42 lowering agents |
| EP2960204B1 (en) * | 2003-05-06 | 2018-06-13 | Air Products And Chemicals, Inc. | Hydrogen storage by reversible hydrogenation 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 |
| DK2802320T3 (da) * | 2011-11-15 | 2019-05-27 | Yissum Res Dev Co Of Hebrew Univ Jerusalem Ltd | Tricykliske forbindelser, sammensætninger omfattende disse og anvendelser deraf |
| 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 (enrdf_load_stackoverflow) * | ||||
| 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 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
- 1973-07-20 IL IL42799A patent/IL42799A/en unknown
- 1973-07-23 DD DD172456A patent/DD107681A5/xx unknown
- 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 DE DE2337340A patent/DE2337340C2/de not_active Expired
- 1973-07-23 SE SE7310244A patent/SE402283B/xx unknown
- 1973-07-23 FI FI2311/73A patent/FI59244C/fi active
- 1973-07-23 AT AT649773A patent/AT325607B/de not_active IP Right Cessation
- 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 CA CA177,061A patent/CA1026348A/en not_active Expired
- 1973-07-23 IE IE1252/73A patent/IE37942B1/xx unknown
- 1973-07-23 JP JP48081008A patent/JPS5740144B2/ja not_active Expired
- 1973-07-23 NO NO2975/73A patent/NO142865C/no unknown
- 1973-07-24 FR FR7327020A patent/FR2193611B1/fr not_active Expired
- 1973-07-24 NL NLAANVRAGE7310275,A patent/NL169877C/xx not_active IP Right Cessation
- 1973-07-24 SU SU1950151A patent/SU509220A3/ru active
-
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
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