JP2005523310A - 置換インドール - Google Patents
置換インドール Download PDFInfo
- Publication number
- JP2005523310A JP2005523310A JP2003584042A JP2003584042A JP2005523310A JP 2005523310 A JP2005523310 A JP 2005523310A JP 2003584042 A JP2003584042 A JP 2003584042A JP 2003584042 A JP2003584042 A JP 2003584042A JP 2005523310 A JP2005523310 A JP 2005523310A
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- JP
- Japan
- Prior art keywords
- propyl
- indole
- carbonitrile
- formula
- carbon atoms
- 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.)
- Pending
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- 150000002475 indoles Chemical class 0.000 title abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- -1 depressant Substances 0.000 claims abstract description 43
- 206010008118 cerebral infarction Diseases 0.000 claims abstract description 20
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 16
- 230000000694 effects Effects 0.000 claims abstract description 16
- 208000026106 cerebrovascular disease Diseases 0.000 claims abstract description 15
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 12
- 201000006474 Brain Ischemia Diseases 0.000 claims abstract description 12
- 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 12
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 12
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 10
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 10
- 208000023105 Huntington disease Diseases 0.000 claims abstract description 9
- 206010015037 epilepsy Diseases 0.000 claims abstract description 8
- 230000007574 infarction Effects 0.000 claims abstract description 8
- 239000003194 amino acid receptor blocking agent Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 166
- 125000004432 carbon atom Chemical group C* 0.000 claims description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 229910004013 NO 2 Inorganic materials 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 239000012453 solvate Substances 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 229910021645 metal ion Inorganic materials 0.000 claims description 9
- 208000006011 Stroke Diseases 0.000 claims description 8
- 210000004556 brain Anatomy 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 208000016285 Movement disease Diseases 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
- 208000032841 Bulimia Diseases 0.000 claims description 5
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
- 208000030814 Eating disease Diseases 0.000 claims description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
- 208000020358 Learning disease Diseases 0.000 claims description 5
- 208000026139 Memory disease Diseases 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 235000014632 disordered eating Nutrition 0.000 claims description 5
- 201000003723 learning disability Diseases 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- PXELOZKDYKBIJY-UHFFFAOYSA-N 4-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 PXELOZKDYKBIJY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- LHBNXAJKGKFNQP-UHFFFAOYSA-N 5-[3-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC3=CC=C4NC=C(C4=C3)C#N)=NSC2=C1 LHBNXAJKGKFNQP-UHFFFAOYSA-N 0.000 claims description 4
- IZNRPDFMASPLES-UHFFFAOYSA-N 5-[3-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCN1CCCC1=CC=C2NC=C(C#N)C2=C1 IZNRPDFMASPLES-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- 210000000278 spinal cord Anatomy 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- WBFKJKOCOVODTF-UHFFFAOYSA-N 1-methylsulfonyl-5-[3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl]indole-3-carbonitrile Chemical compound C=1C=C2N(S(=O)(=O)C)C=C(C#N)C2=CC=1CCCN(CC1)CCC1(C(NC1)=O)N1C1=CC=CC=C1 WBFKJKOCOVODTF-UHFFFAOYSA-N 0.000 claims description 3
- DIAOOLPCGOOIHV-UHFFFAOYSA-N 3-[1-[3-(3-cyano-1h-indol-5-yl)propyl]piperidin-4-yl]-1h-indole-5-carboxamide Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCC(CC2)C2=CNC3=CC=C(C=C32)C(=O)N)=C1 DIAOOLPCGOOIHV-UHFFFAOYSA-N 0.000 claims description 3
- MOWLYAKTKWMUQE-UHFFFAOYSA-N 4-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 MOWLYAKTKWMUQE-UHFFFAOYSA-N 0.000 claims description 3
- PJMFZXWLBNTPPK-UHFFFAOYSA-N 4-[3-[4-(pyrazol-1-ylmethyl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C=12C(C#N)=CNC2=CC=CC=1CCCN(CC1)CCC1CN1C=CC=N1 PJMFZXWLBNTPPK-UHFFFAOYSA-N 0.000 claims description 3
- ZIYLVELXOPYOGF-UHFFFAOYSA-N 4-[3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 ZIYLVELXOPYOGF-UHFFFAOYSA-N 0.000 claims description 3
- BFLZMCZQKOZXEG-UHFFFAOYSA-N 5-[3-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl]-1h-indole-3-carbonitrile Chemical compound C1CN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CCC11C(=O)NCN1C1=CC=CC=C1 BFLZMCZQKOZXEG-UHFFFAOYSA-N 0.000 claims description 3
- FNYSVQHTACRZCQ-UHFFFAOYSA-N 5-[3-(4-quinolin-8-ylpiperazin-1-yl)propyl]-1h-indole-3-carbonitrile Chemical compound C1=CN=C2C(N3CCN(CC3)CCCC3=CC=C4NC=C(C4=C3)C#N)=CC=CC2=C1 FNYSVQHTACRZCQ-UHFFFAOYSA-N 0.000 claims description 3
- PUYTZMAGOKFVTQ-UHFFFAOYSA-N 5-[3-(pyridin-3-ylmethylamino)propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2C(C#N)=CNC2=CC=C1CCCNCC1=CC=CN=C1 PUYTZMAGOKFVTQ-UHFFFAOYSA-N 0.000 claims description 3
- ZKHNWRRKOTXSPJ-UHFFFAOYSA-N 5-[3-[4-(1h-indol-4-yl)piperazin-1-yl]propyl]-1-methylsulfonylindole-3-carbonitrile Chemical compound C=1C=C2N(S(=O)(=O)C)C=C(C#N)C2=CC=1CCCN(CC1)CCN1C1=CC=CC2=C1C=CN2 ZKHNWRRKOTXSPJ-UHFFFAOYSA-N 0.000 claims description 3
- CJNKOGGPTBTMSU-UHFFFAOYSA-N 5-[3-[4-(1h-indol-4-yl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2C(C#N)=CNC2=CC=C1CCCN(CC1)CCN1C1=CC=CC2=C1C=CN2 CJNKOGGPTBTMSU-UHFFFAOYSA-N 0.000 claims description 3
- LWDPDVUFDXJIOG-UHFFFAOYSA-N 5-[3-[4-(2,1,3-benzothiadiazol-4-yl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC2=NSN=C2C(N2CCN(CC2)CCCC2=CC=C3NC=C(C3=C2)C#N)=C1 LWDPDVUFDXJIOG-UHFFFAOYSA-N 0.000 claims description 3
- OMOPFUXSBWKXBT-UHFFFAOYSA-N 5-[3-[4-(2-oxochromen-6-yl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCN(CC2)C=2C=C3C=CC(OC3=CC=2)=O)=C1 OMOPFUXSBWKXBT-UHFFFAOYSA-N 0.000 claims description 3
- PJUOUUCPBVTXOS-UHFFFAOYSA-N 5-[3-[4-(4-cyanophenyl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2C(C#N)=CNC2=CC=C1CCCN(CC1)CCN1C1=CC=C(C#N)C=C1 PJUOUUCPBVTXOS-UHFFFAOYSA-N 0.000 claims description 3
- QPLGCQCJAORPKN-UHFFFAOYSA-N 5-[3-[4-(4-fluoro-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCC(CC2)C2=CNC=3C=CC=C(C2=3)F)=C1 QPLGCQCJAORPKN-UHFFFAOYSA-N 0.000 claims description 3
- VVVQINXECOLIRC-UHFFFAOYSA-N 5-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 VVVQINXECOLIRC-UHFFFAOYSA-N 0.000 claims description 3
- KDNJQJFKQOOBMJ-UHFFFAOYSA-N 5-[3-[4-(5-cyano-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C(C#N)C=C2C(C3CCN(CC3)CCCC3=CC=C4NC=C(C4=C3)C#N)=CNC2=C1 KDNJQJFKQOOBMJ-UHFFFAOYSA-N 0.000 claims description 3
- FICXHYVHQPSCLK-UHFFFAOYSA-N 5-[3-[4-(5-fluoro-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCC(CC2)C2=CNC3=CC=C(C=C32)F)=C1 FICXHYVHQPSCLK-UHFFFAOYSA-N 0.000 claims description 3
- JWJKRLHAJXYPOD-UHFFFAOYSA-N 5-[3-[4-(6-fluoro-1h-indol-3-yl)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCC(CC2)C=2C3=CC=C(C=C3NC=2)F)=C1 JWJKRLHAJXYPOD-UHFFFAOYSA-N 0.000 claims description 3
- MORGGAAGUJMDJP-UHFFFAOYSA-N 5-[3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 MORGGAAGUJMDJP-UHFFFAOYSA-N 0.000 claims description 3
- WJQQNOKNWKZKEI-UHFFFAOYSA-N 5-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 WJQQNOKNWKZKEI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- VUAQTHXRQVAQCD-UHFFFAOYSA-N 6-[3-[4-(2-cyano-3-methoxyphenyl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound COC1=CC=CC(N2CCN(CCCC=3C=C4NC=C(C4=CC=3)C#N)CC2)=C1C#N VUAQTHXRQVAQCD-UHFFFAOYSA-N 0.000 claims description 3
- WCBZWCPBDGJJFQ-UHFFFAOYSA-N 6-[3-[4-(4-cyano-2-methoxyphenyl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound COC1=CC(C#N)=CC=C1N1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 WCBZWCPBDGJJFQ-UHFFFAOYSA-N 0.000 claims description 3
- BQFVQUWWCSIHEW-UHFFFAOYSA-N 6-[3-[4-(4-cyano-3-methoxyphenyl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C(C#N)C(OC)=CC(N2CCN(CCCC=3C=C4NC=C(C4=CC=3)C#N)CC2)=C1 BQFVQUWWCSIHEW-UHFFFAOYSA-N 0.000 claims description 3
- MGWLYPWRAOWAGO-UHFFFAOYSA-N 6-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 MGWLYPWRAOWAGO-UHFFFAOYSA-N 0.000 claims description 3
- GAOVZTNLDBPBEH-UHFFFAOYSA-N 6-[3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 GAOVZTNLDBPBEH-UHFFFAOYSA-N 0.000 claims description 3
- DMWILBQJRHOAJR-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 DMWILBQJRHOAJR-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003342 alkenyl group Chemical group 0.000 claims description 3
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- JMUKSNFJRVESEX-UHFFFAOYSA-N ethyl 2-[4-[3-(3-cyano-1h-indol-5-yl)propyl]piperazin-1-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(N2CCN(CCCC=3C=C4C(C#N)=CNC4=CC=3)CC2)=N1 JMUKSNFJRVESEX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 2
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- QXWBWDNCQPWTRZ-UHFFFAOYSA-N 5-[3-(4-pyrimidin-2-ylpiperazin-1-yl)propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2C(C#N)=CNC2=CC=C1CCCN(CC1)CCN1C1=NC=CC=N1 QXWBWDNCQPWTRZ-UHFFFAOYSA-N 0.000 claims description 2
- RQOYNNPRLDBPRW-UHFFFAOYSA-N 5-[3-[3-(2-oxopyrrolidin-1-yl)propylamino]propyl]-1h-indole-3-carbonitrile Chemical compound O=C1CCCN1CCCNCCCC1=CC=C(NC=C2C#N)C2=C1 RQOYNNPRLDBPRW-UHFFFAOYSA-N 0.000 claims description 2
- LRQYBPXGUKKCLK-UHFFFAOYSA-N 5-[3-[4-(1-methylimidazo[4,5-c]pyridin-4-yl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCN(CC2)C2=C3N=CN(C3=CC=N2)C)=C1 LRQYBPXGUKKCLK-UHFFFAOYSA-N 0.000 claims description 2
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- IBBLTAZDDRHFHT-UHFFFAOYSA-N 5-[3-[4-(3-amino-2-oxochromen-6-yl)piperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCN(CC2)C=2C=C3C=C(C(OC3=CC=2)=O)N)=C1 IBBLTAZDDRHFHT-UHFFFAOYSA-N 0.000 claims description 2
- UQALVGIRSOKDSG-UHFFFAOYSA-N 5-[3-[4-(3-methoxyphenyl)-3-methylpiperazin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound COC1=CC=CC(N2C(CN(CCCC=3C=C4C(C#N)=CNC4=CC=3)CC2)C)=C1 UQALVGIRSOKDSG-UHFFFAOYSA-N 0.000 claims description 2
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- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 2
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- XASTVLSRTKFVEJ-UHFFFAOYSA-N n-[4-[[1-[3-(3-cyano-1h-indol-5-yl)propyl]piperidin-4-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 XASTVLSRTKFVEJ-UHFFFAOYSA-N 0.000 claims description 2
- PRNVNPAKZNKDJU-UHFFFAOYSA-N n-[6-[4-[3-(3-cyano-1h-indol-5-yl)propyl]piperazin-1-yl]-2-oxochromen-3-yl]acetamide Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCN(CC2)C=2C=C3C=C(C(OC3=CC=2)=O)NC(=O)C)=C1 PRNVNPAKZNKDJU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
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- 125000005156 substituted alkylene group Chemical group 0.000 claims description 2
- LARCQYXEUOOVJI-UHFFFAOYSA-N 5-[4-[3-(3-cyano-1h-indol-4-yl)propyl]piperazin-1-yl]-1-benzofuran-2-carboxamide Chemical compound C=1C=C2OC(C(=O)N)=CC2=CC=1N(CC1)CCN1CCCC1=CC=CC2=C1C(C#N)=CN2 LARCQYXEUOOVJI-UHFFFAOYSA-N 0.000 claims 1
- QPLROEKPKXETSR-UHFFFAOYSA-N 5-[4-[3-(3-cyano-1h-indol-5-yl)propyl]piperazin-1-yl]-1-benzofuran-2-carboxamide Chemical compound C1=C2NC=C(C#N)C2=CC(CCCN2CCN(CC2)C=2C=C3C=C(OC3=CC=2)C(=O)N)=C1 QPLROEKPKXETSR-UHFFFAOYSA-N 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 239000005557 antagonist Substances 0.000 abstract description 7
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10217006A DE10217006A1 (de) | 2002-04-16 | 2002-04-16 | Substituierte Indole |
| PCT/EP2003/003806 WO2003087086A2 (de) | 2002-04-16 | 2003-04-11 | Substituierte indole und deren verwendung als 5ht-wiederaufnahme inhibitoren und als 5ht liganden |
Publications (2)
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| JP2005523310A true JP2005523310A (ja) | 2005-08-04 |
| JP2005523310A5 JP2005523310A5 (enExample) | 2006-06-01 |
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| Country | Link |
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| US (3) | US7572796B2 (enExample) |
| EP (1) | EP1497279B1 (enExample) |
| JP (1) | JP2005523310A (enExample) |
| AT (1) | ATE501133T1 (enExample) |
| AU (1) | AU2003224064A1 (enExample) |
| CA (1) | CA2482655C (enExample) |
| DE (2) | DE10217006A1 (enExample) |
| DK (1) | DK1497279T3 (enExample) |
| ES (1) | ES2362871T3 (enExample) |
| WO (1) | WO2003087086A2 (enExample) |
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| JP2006512380A (ja) * | 2002-12-20 | 2006-04-13 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 置換ベンゾジオキセピン |
| WO2010090009A1 (ja) * | 2009-02-05 | 2010-08-12 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | インドリン誘導体 |
| JP2016526576A (ja) * | 2013-07-15 | 2016-09-05 | ノバルティス アーゲー | ピペリジニル−インドール誘導体および補体因子b阻害剤としてのその使用 |
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2002
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2003
- 2003-04-11 AT AT03720455T patent/ATE501133T1/de active
- 2003-04-11 US US10/511,155 patent/US7572796B2/en not_active Expired - Fee Related
- 2003-04-11 WO PCT/EP2003/003806 patent/WO2003087086A2/de not_active Ceased
- 2003-04-11 AU AU2003224064A patent/AU2003224064A1/en not_active Abandoned
- 2003-04-11 EP EP03720455A patent/EP1497279B1/de not_active Expired - Lifetime
- 2003-04-11 CA CA2482655A patent/CA2482655C/en not_active Expired - Fee Related
- 2003-04-11 DK DK03720455.9T patent/DK1497279T3/da active
- 2003-04-11 ES ES03720455T patent/ES2362871T3/es not_active Expired - Lifetime
- 2003-04-11 JP JP2003584042A patent/JP2005523310A/ja active Pending
- 2003-04-11 DE DE50313528T patent/DE50313528D1/de not_active Expired - Lifetime
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| US3280145A (en) * | 1963-06-04 | 1966-10-18 | Sandoz Ltd | New indole derivatives and their acid addition salts |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006512380A (ja) * | 2002-12-20 | 2006-04-13 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 置換ベンゾジオキセピン |
| WO2010090009A1 (ja) * | 2009-02-05 | 2010-08-12 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | インドリン誘導体 |
| US8686024B2 (en) | 2009-02-05 | 2014-04-01 | Kyoto University | Indoline derivatives |
| JP2016526576A (ja) * | 2013-07-15 | 2016-09-05 | ノバルティス アーゲー | ピペリジニル−インドール誘導体および補体因子b阻害剤としてのその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003224064A1 (en) | 2003-10-27 |
| WO2003087086A3 (de) | 2004-07-22 |
| US20090291963A1 (en) | 2009-11-26 |
| CA2482655A1 (en) | 2003-10-23 |
| ATE501133T1 (de) | 2011-03-15 |
| EP1497279A2 (de) | 2005-01-19 |
| ES2362871T3 (es) | 2011-07-14 |
| EP1497279B1 (de) | 2011-03-09 |
| US20050153980A1 (en) | 2005-07-14 |
| CA2482655C (en) | 2011-08-16 |
| WO2003087086A2 (de) | 2003-10-23 |
| DE50313528D1 (de) | 2011-04-21 |
| AU2003224064A8 (en) | 2003-10-27 |
| DE10217006A1 (de) | 2003-11-06 |
| DK1497279T3 (da) | 2011-06-14 |
| US20090054459A1 (en) | 2009-02-26 |
| US7572796B2 (en) | 2009-08-11 |
| US8058277B2 (en) | 2011-11-15 |
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