JP3989444B2 - 新規な化合物 - Google Patents
新規な化合物 Download PDFInfo
- Publication number
- JP3989444B2 JP3989444B2 JP2003580319A JP2003580319A JP3989444B2 JP 3989444 B2 JP3989444 B2 JP 3989444B2 JP 2003580319 A JP2003580319 A JP 2003580319A JP 2003580319 A JP2003580319 A JP 2003580319A JP 3989444 B2 JP3989444 B2 JP 3989444B2
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- alkyl
- indol
- hydroxy
- compound
- 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 - Fee Related
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- 150000001875 compounds Chemical class 0.000 title claims description 268
- 125000000217 alkyl group Chemical group 0.000 claims description 143
- 239000002904 solvent Substances 0.000 claims description 100
- 238000006243 chemical reaction Methods 0.000 claims description 97
- 239000002585 base Substances 0.000 claims description 82
- -1 (CO) OR 4 Chemical group 0.000 claims description 78
- 125000005842 heteroatom Chemical group 0.000 claims description 48
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 36
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 239000012458 free base Substances 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 21
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- 238000010992 reflux Methods 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 9
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 7
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical group CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims description 5
- ZSBINQQBBOUXFI-UHFFFAOYSA-N ethyl 6-(2-hydroxy-5-nitro-1H-indol-3-yl)pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OCC)=CC=C1C1=C(O)NC2=CC=C([N+]([O-])=O)C=C12 ZSBINQQBBOUXFI-UHFFFAOYSA-N 0.000 claims description 5
- APRYBBRXBYNGRD-WLHGVMLRSA-N (E)-but-2-enedioic acid 3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-5-(1,3-thiazol-4-yl)-1H-indol-2-ol Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCN1S(=O)(=O)c1ccc(-c2c([nH]c3ccc(cc32)-c2cscn2)O)nc1 APRYBBRXBYNGRD-WLHGVMLRSA-N 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- QFJWLSYVRJXJKO-WLHGVMLRSA-N (E)-but-2-enedioic acid 2-hydroxy-3-[5-[(4-methyl-1,4-diazepan-1-yl)sulfonyl]pyridin-2-yl]-1H-indole-5-carbonitrile Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCCN1S(=O)(=O)c1ccc(-c2c([nH]c3ccc(cc32)C#N)O)nc1 QFJWLSYVRJXJKO-WLHGVMLRSA-N 0.000 claims description 3
- ZFRDGCKDAKVMRW-WLHGVMLRSA-N (E)-but-2-enedioic acid [6-(2-hydroxy-5-nitro-1H-indol-3-yl)pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C)CCN1C(=O)c1ccc(-c2c([nH]c3ccc(cc32)[N+]([O-])=O)O)nc1 ZFRDGCKDAKVMRW-WLHGVMLRSA-N 0.000 claims description 3
- HGCLVHWOIGDXAZ-UHFFFAOYSA-N 2-hydroxy-3-(5-morpholin-4-ylsulfonylpyridin-2-yl)-1H-indole-5-carbonitrile Chemical compound OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1S(=O)(=O)N1CCOCC1 HGCLVHWOIGDXAZ-UHFFFAOYSA-N 0.000 claims description 3
- TUHYCRZRVGKOJC-UHFFFAOYSA-N 2-hydroxy-3-[4-(4-methylpiperazine-1-carbonyl)pyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C1=CC=NC(C=2C3=CC(=CC=C3NC=2O)C#N)=C1 TUHYCRZRVGKOJC-UHFFFAOYSA-N 0.000 claims description 3
- SYFQOGMYKZJTMV-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 SYFQOGMYKZJTMV-UHFFFAOYSA-N 0.000 claims description 3
- OZZYJFSOFDTEHW-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-6-carbonitrile hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC=C(C=C3NC=2O)C#N)N=C1 OZZYJFSOFDTEHW-UHFFFAOYSA-N 0.000 claims description 3
- QEGKDXPEXXJSBJ-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-propan-2-ylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.C1CN(C(C)C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 QEGKDXPEXXJSBJ-UHFFFAOYSA-N 0.000 claims description 3
- GXJPJFUWGWGPBU-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indole-6-carbonitrile hydrochloride Chemical compound Cl.OC=1NC2=CC(C#N)=CC=C2C=1C(N=C1)=CC=C1CN1CCOCC1 GXJPJFUWGWGPBU-UHFFFAOYSA-N 0.000 claims description 3
- FJVACSNRHIUTDK-UHFFFAOYSA-N 2-hydroxy-3-[5-(piperidin-1-ylmethyl)pyridin-2-yl]-1H-indole-5-carbonitrile Chemical compound OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN1CCCCC1 FJVACSNRHIUTDK-UHFFFAOYSA-N 0.000 claims description 3
- XYQALSFZTTXKKD-UHFFFAOYSA-N 2-hydroxy-3-[5-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]pyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN(CC1)CCC1N1CCCC1 XYQALSFZTTXKKD-UHFFFAOYSA-N 0.000 claims description 3
- CFBOLIJNHXMZMR-UHFFFAOYSA-N 2-hydroxy-3-[5-[4-(3-methylbutyl)piperazin-1-yl]sulfonylpyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.C1CN(CCC(C)C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 CFBOLIJNHXMZMR-UHFFFAOYSA-N 0.000 claims description 3
- CCRQRQITUSYUCY-UHFFFAOYSA-N 3-[3-bromo-5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-5-nitro-1H-indol-2-ol hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C(C=C1Br)=CN=C1C1=C(O)NC2=CC=C([N+]([O-])=O)C=C12 CCRQRQITUSYUCY-UHFFFAOYSA-N 0.000 claims description 3
- QPPWLYQVGNXFTA-UHFFFAOYSA-N 3-[5-(4-benzylpiperazin-1-yl)sulfonylpyridin-2-yl]-2-hydroxy-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1S(=O)(=O)N(CC1)CCN1CC1=CC=CC=C1 QPPWLYQVGNXFTA-UHFFFAOYSA-N 0.000 claims description 3
- OTFZDRAEWUHKJF-UHFFFAOYSA-N 3-[5-(4-ethylpiperazin-1-yl)sulfonylpyridin-2-yl]-2-hydroxy-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.C1CN(CC)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 OTFZDRAEWUHKJF-UHFFFAOYSA-N 0.000 claims description 3
- XYUBCWOJCJVECF-UHFFFAOYSA-N 3-[5-(azetidin-1-ylmethyl)pyridin-2-yl]-2-hydroxy-1H-indole-5-carbonitrile Chemical compound OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN1CCC1 XYUBCWOJCJVECF-UHFFFAOYSA-N 0.000 claims description 3
- PSGREWNLJTVWIU-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-indol-2-ol hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C(F)(F)F)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 PSGREWNLJTVWIU-UHFFFAOYSA-N 0.000 claims description 3
- LCJSFFYXNSCWRH-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-5-nitro-1H-indol-2-ol hydrochloride Chemical compound Cl.OC=1NC2=CC=C([N+]([O-])=O)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 LCJSFFYXNSCWRH-UHFFFAOYSA-N 0.000 claims description 3
- LCXBCMKWUPCGNT-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-5-thiophen-2-yl-1H-indol-2-ol hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C=3SC=CC=3)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 LCXBCMKWUPCGNT-UHFFFAOYSA-N 0.000 claims description 3
- NYLFEHCKPMZKQY-UHFFFAOYSA-N 3-[5-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]pyridin-2-yl]-2-hydroxy-1H-indole-5-carbonitrile Chemical compound C1C(N(C)C)CCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 NYLFEHCKPMZKQY-UHFFFAOYSA-N 0.000 claims description 3
- QBMKVGAHJVUDMD-UHFFFAOYSA-N 5,6-dibromo-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indol-2-ol hydrochloride Chemical compound Cl.OC=1NC2=CC(Br)=C(Br)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 QBMKVGAHJVUDMD-UHFFFAOYSA-N 0.000 claims description 3
- FAABSFPFSLKXNZ-UHFFFAOYSA-N 5-(furan-2-yl)-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indol-2-ol hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C=3OC=CC=3)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 FAABSFPFSLKXNZ-UHFFFAOYSA-N 0.000 claims description 3
- LLAZTZBIMDHGFQ-UHFFFAOYSA-N 6-(5-cyano-2-hydroxy-1H-indol-3-yl)-N-(2-pyrrolidin-1-ylethyl)pyridine-3-sulfonamide hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1S(=O)(=O)NCCN1CCCC1 LLAZTZBIMDHGFQ-UHFFFAOYSA-N 0.000 claims description 3
- GFRMJDAREJXJMH-UHFFFAOYSA-N 6-(5-cyano-2-hydroxy-1H-indol-3-yl)-N-[2-(dimethylamino)ethyl]-N-methylpyridine-3-carboxamide hydrochloride Chemical compound Cl.N1=CC(C(=O)N(C)CCN(C)C)=CC=C1C1=C(O)NC2=CC=C(C#N)C=C12 GFRMJDAREJXJMH-UHFFFAOYSA-N 0.000 claims description 3
- ANSNPHYKHZDIDV-UHFFFAOYSA-N 6-chloro-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indol-2-ol hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC=C(Cl)C=C3NC=2O)N=C1 ANSNPHYKHZDIDV-UHFFFAOYSA-N 0.000 claims description 3
- BUHJHFJDPDIPMP-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[6-(2-hydroxy-5-nitro-1H-indol-3-yl)pyridin-3-yl]methanone hydrochloride Chemical compound Cl.C1C(N(C)C)CCN1C(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)[N+]([O-])=O)N=C1 BUHJHFJDPDIPMP-UHFFFAOYSA-N 0.000 claims description 3
- PCEVLYRCZVWKNL-UHFFFAOYSA-N [6-(2-hydroxy-5-nitro-1H-indol-3-yl)pyridin-3-yl]-(4-pyrrolidin-1-ylpiperidin-1-yl)methanone hydrochloride Chemical compound Cl.OC=1NC2=CC=C([N+]([O-])=O)C=C2C=1C(N=C1)=CC=C1C(=O)N(CC1)CCC1N1CCCC1 PCEVLYRCZVWKNL-UHFFFAOYSA-N 0.000 claims description 3
- QVPHTKOEMVVGNO-UHFFFAOYSA-N [6-(2-hydroxy-5-nitro-1H-indol-3-yl)pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound OC=1NC2=CC=C([N+]([O-])=O)C=C2C=1C(N=C1)=CC=C1C(=O)N1CCOCC1 QVPHTKOEMVVGNO-UHFFFAOYSA-N 0.000 claims description 3
- 229940064982 ethylnicotinate Drugs 0.000 claims description 3
- AGWBFQVRRSLCHJ-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazine-1-carbonyl)pyridin-2-yl]-1H-indole-5-carbonitrile Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 AGWBFQVRRSLCHJ-UHFFFAOYSA-N 0.000 claims description 2
- HSQKJKZGOSVCOZ-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 HSQKJKZGOSVCOZ-UHFFFAOYSA-N 0.000 claims description 2
- GBLNSBPFSFVPQU-UHFFFAOYSA-N 2-hydroxy-3-[5-(pyrrolidin-1-ylmethyl)pyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN1CCCC1 GBLNSBPFSFVPQU-UHFFFAOYSA-N 0.000 claims description 2
- VBOGGFCZFUJSMT-UHFFFAOYSA-N 2-hydroxy-3-[5-[(4-methyl-1,4-diazepan-1-yl)methyl]pyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.C1CN(C)CCCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 VBOGGFCZFUJSMT-UHFFFAOYSA-N 0.000 claims description 2
- AICZIXZCGTTZLV-UHFFFAOYSA-N 2-hydroxy-3-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]-1H-indole-5-carbonitrile hydrochloride Chemical compound Cl.C1CN(C)CCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 AICZIXZCGTTZLV-UHFFFAOYSA-N 0.000 claims description 2
- GPTISHQYMJHWON-UHFFFAOYSA-N 2-hydroxy-3-[5-[(4-methylpiperidin-1-yl)methyl]pyridin-2-yl]-1H-indole-5-carbonitrile Chemical compound C1CC(C)CCN1CC1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 GPTISHQYMJHWON-UHFFFAOYSA-N 0.000 claims description 2
- KPMVLWSSNOTENQ-UHFFFAOYSA-N 2-hydroxy-3-[5-[(4-phenylpiperazin-1-yl)methyl]pyridin-2-yl]-1H-indole-5-carbonitrile Chemical compound OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN(CC1)CCN1C1=CC=CC=C1 KPMVLWSSNOTENQ-UHFFFAOYSA-N 0.000 claims description 2
- BCJXCAKHQLKPLH-UHFFFAOYSA-N 2-hydroxy-3-[6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]-1H-indole-5-carbonitrile Chemical compound OC=1NC2=CC=C(C#N)C=C2C=1C(N=CN=1)=CC=1OCCN1CCOCC1 BCJXCAKHQLKPLH-UHFFFAOYSA-N 0.000 claims description 2
- AUBFRFKDPRVUMI-UHFFFAOYSA-N 3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indol-2-ol hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC=CC=C3NC=2O)N=C1 AUBFRFKDPRVUMI-UHFFFAOYSA-N 0.000 claims description 2
- FLRICODGIDQWDO-UHFFFAOYSA-N 3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-5-(2-methyl-1,3-thiazol-4-yl)-1H-indol-2-ol hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C=2N=C(C)SC=2)N=C1 FLRICODGIDQWDO-UHFFFAOYSA-N 0.000 claims description 2
- MFBJGERJCYKORO-UHFFFAOYSA-N 3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-5-pyridin-3-yl-1H-indol-2-ol Chemical group OC=1NC2=CC=C(C=3C=NC=CC=3)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 MFBJGERJCYKORO-UHFFFAOYSA-N 0.000 claims description 2
- DGYOQSAUPDVPQH-UHFFFAOYSA-N 3-fluoro-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-2-oxo-1h-indole-6-carbonitrile;hydrochloride Chemical compound Cl.O=C1NC2=CC(C#N)=CC=C2C1(F)C(N=C1)=CC=C1CN1CCOCC1 DGYOQSAUPDVPQH-UHFFFAOYSA-N 0.000 claims description 2
- IJLCISXHAWDSQV-UHFFFAOYSA-N 5-bromo-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indol-2-ol hydrochloride Chemical compound Cl.OC=1NC2=CC=C(Br)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 IJLCISXHAWDSQV-UHFFFAOYSA-N 0.000 claims description 2
- GECIALRGJBQECL-UHFFFAOYSA-N 6-(5-cyano-2-hydroxy-1H-indol-3-yl)-N-methyl-N-(2-pyrrolidin-1-ylethyl)pyridine-3-sulfonamide hydrochloride Chemical compound Cl.C=1C=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=CC=1S(=O)(=O)N(C)CCN1CCCC1 GECIALRGJBQECL-UHFFFAOYSA-N 0.000 claims description 2
- ISCKFWGPRHZHEU-UHFFFAOYSA-N 6-bromo-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-1H-indol-2-ol hydrochloride Chemical compound Cl.OC=1NC2=CC(Br)=CC=C2C=1C(N=C1)=CC=C1CN1CCOCC1 ISCKFWGPRHZHEU-UHFFFAOYSA-N 0.000 claims description 2
- BLTVBQXJFVRPFK-UHFFFAOYSA-N AZD1080 Chemical compound OC=1NC2=CC=C(C#N)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 BLTVBQXJFVRPFK-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 270
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 170
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 132
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 116
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| YU4403A (sh) * | 2000-07-27 | 2006-05-25 | F. Hoffmann-La Roche Ag. | Derivati 3-indolil-4-fenil-1h-pirol-2,5-diona, kao inhibitori glikogen sintaza kinaze-3 beta |
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| SE0104341D0 (sv) | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New use |
| SE0104340D0 (sv) | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New compounds |
| TW200301123A (en) | 2001-12-21 | 2003-07-01 | Astrazeneca Uk Ltd | New use |
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| SE0302546D0 (sv) * | 2003-09-24 | 2003-09-24 | Astrazeneca Ab | New compounds |
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