JP2010539180A5 - - Google Patents
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- Publication number
- JP2010539180A5 JP2010539180A5 JP2010524978A JP2010524978A JP2010539180A5 JP 2010539180 A5 JP2010539180 A5 JP 2010539180A5 JP 2010524978 A JP2010524978 A JP 2010524978A JP 2010524978 A JP2010524978 A JP 2010524978A JP 2010539180 A5 JP2010539180 A5 JP 2010539180A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidin
- ylethyl
- oxo
- tetrahydroisoquinolin
- ethyl
- 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.)
- Withdrawn
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- -1 cycloheteroalkyl Chemical group 0.000 claims 32
- 150000003839 salts Chemical class 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical class OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 claims 1
- 150000005072 1,3,4-oxadiazoles Chemical class 0.000 claims 1
- IIQVHLRPDRFQHC-UHFFFAOYSA-N 1-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]indole-5-carbonitrile Chemical compound C1CC2=CC(N3C4=CC=C(C=C4C=C3)C#N)=CC=C2C(=O)N1CCN1CCCC1 IIQVHLRPDRFQHC-UHFFFAOYSA-N 0.000 claims 1
- YFURTEYAEPSLFX-UHFFFAOYSA-N 2-(2-pyrrolidin-1-ylethyl)-6-[3-(trifluoromethoxy)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound FC(F)(F)OC1=CC=CC(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)=C1 YFURTEYAEPSLFX-UHFFFAOYSA-N 0.000 claims 1
- YGDXRYIZHALWOY-UHFFFAOYSA-N 2-(2-pyrrolidin-1-ylethyl)-6-[3-(trifluoromethyl)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound FC(F)(F)C1=CC=CC(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)=C1 YGDXRYIZHALWOY-UHFFFAOYSA-N 0.000 claims 1
- SXUZRGLZTPXKSU-UHFFFAOYSA-N 2-(2-pyrrolidin-1-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(CN(CCN2CCCC2)CC2)C2=C1 SXUZRGLZTPXKSU-UHFFFAOYSA-N 0.000 claims 1
- UZARNTGJNZJLMB-UHFFFAOYSA-N 2-(2-pyrrolidin-1-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 UZARNTGJNZJLMB-UHFFFAOYSA-N 0.000 claims 1
- IZGHSNVQGBODFP-UHFFFAOYSA-N 2-(2-pyrrolidin-1-ylethyl)-6-[4-(trifluoromethyl)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 IZGHSNVQGBODFP-UHFFFAOYSA-N 0.000 claims 1
- VCCZQTCRRYEOMQ-UHFFFAOYSA-N 2-[2-(azepan-1-yl)ethyl]-6-(4-fluorophenyl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC(F)=CC=C1C1=CC=C(CN(CCN2CCCCCC2)CC2)C2=C1 VCCZQTCRRYEOMQ-UHFFFAOYSA-N 0.000 claims 1
- ULDQVOFOHYQSEB-UHFFFAOYSA-N 2-[2-(azepan-1-yl)ethyl]-6-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)N(CCN2CCCCCC2)CC2)C2=C1 ULDQVOFOHYQSEB-UHFFFAOYSA-N 0.000 claims 1
- LHOPPDSAKXYMGM-UHFFFAOYSA-N 2-[2-(azepan-1-yl)ethyl]-6-piperidin-1-yl-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(N3CCCCC3)=CC=C2C(=O)N1CCN1CCCCCC1 LHOPPDSAKXYMGM-UHFFFAOYSA-N 0.000 claims 1
- LVGUHWADRXKKTN-MRXNPFEDSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-n-pyridin-4-yl-3,4-dihydroisoquinoline-6-carboxamide Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C(=O)NC=3C=CN=CC=3)C=C2CC1 LVGUHWADRXKKTN-MRXNPFEDSA-N 0.000 claims 1
- VIXLFZWEFXGIRZ-LJQANCHMSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-5-[4-(pyrrolidine-1-carbonyl)phenyl]-3h-isoindol-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(=CC=3)C(=O)N3CCCC3)C=C2C1 VIXLFZWEFXGIRZ-LJQANCHMSA-N 0.000 claims 1
- DYWLJRPIZPWGET-QGZVFWFLSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-(1-oxo-3,4-dihydro-2h-isoquinolin-6-yl)-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=C4CCNC(=O)C4=CC=3)C=C2CC1 DYWLJRPIZPWGET-QGZVFWFLSA-N 0.000 claims 1
- XNIIGFMTISXHOP-QGZVFWFLSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-(piperidine-1-carbonyl)-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C(=O)N3CCCCC3)C=C2CC1 XNIIGFMTISXHOP-QGZVFWFLSA-N 0.000 claims 1
- DOZZMXWYOSFCSK-MRXNPFEDSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-(pyrrolidine-1-carbonyl)-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C(=O)N3CCCC3)C=C2CC1 DOZZMXWYOSFCSK-MRXNPFEDSA-N 0.000 claims 1
- CGMNEQRSMXPAEO-HXUWFJFHSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-[4-(morpholine-4-carbonyl)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(=CC=3)C(=O)N3CCOCC3)C=C2CC1 CGMNEQRSMXPAEO-HXUWFJFHSA-N 0.000 claims 1
- RWVLKSWAEQZIHC-OAQYLSRUSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-[4-(piperidine-1-carbonyl)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(=CC=3)C(=O)N3CCCCC3)C=C2CC1 RWVLKSWAEQZIHC-OAQYLSRUSA-N 0.000 claims 1
- XPZHIEBBPQVJCT-HXUWFJFHSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-[4-(pyrrolidine-1-carbonyl)phenoxy]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(OC=3C=CC(=CC=3)C(=O)N3CCCC3)C=C2CC1 XPZHIEBBPQVJCT-HXUWFJFHSA-N 0.000 claims 1
- SPKOQCHHYOCMGR-HXUWFJFHSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-[4-(pyrrolidine-1-carbonyl)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(=CC=3)C(=O)N3CCCC3)C=C2CC1 SPKOQCHHYOCMGR-HXUWFJFHSA-N 0.000 claims 1
- OCEASSQDJLNZSQ-QGZVFWFLSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-piperidin-1-yl-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(N3CCCCC3)C=C2CC1 OCEASSQDJLNZSQ-QGZVFWFLSA-N 0.000 claims 1
- BCFUWSDYWOXETI-MRXNPFEDSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-6-pyrrolidin-1-yl-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(N3CCCC3)C=C2CC1 BCFUWSDYWOXETI-MRXNPFEDSA-N 0.000 claims 1
- HJYQEGBJLDVMGC-HXUWFJFHSA-N 2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-7-[4-(pyrrolidine-1-carbonyl)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC(C=3C=CC(=CC=3)C(=O)N3CCCC3)=CC=C2CC1 HJYQEGBJLDVMGC-HXUWFJFHSA-N 0.000 claims 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- RJJREVXLBPEJNJ-UHFFFAOYSA-N 2-methyl-6-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C2C(=O)N(C)CCC2=CC=1C(C=C1CC2)=CC=C1C(=O)N2CCN1CCCC1 RJJREVXLBPEJNJ-UHFFFAOYSA-N 0.000 claims 1
- PPMUILQUJWTJIP-GOSISDBHSA-N 2-methyl-6-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-6-yl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=C4CCN(C)C(=O)C4=CC=3)C=C2CC1 PPMUILQUJWTJIP-GOSISDBHSA-N 0.000 claims 1
- GAWGFYBLRGTQOO-UHFFFAOYSA-N 3-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]benzonitrile Chemical compound C1CC2=CC(C=3C=C(C=CC=3)C#N)=CC=C2C(=O)N1CCN1CCCC1 GAWGFYBLRGTQOO-UHFFFAOYSA-N 0.000 claims 1
- OQCHJTQVESQEMN-UHFFFAOYSA-N 3-[1-oxo-2-(3-pyrrolidin-1-ylpropyl)-3,4-dihydroisoquinolin-6-yl]benzonitrile Chemical compound C1CC2=CC(C=3C=C(C=CC=3)C#N)=CC=C2C(=O)N1CCCN1CCCC1 OQCHJTQVESQEMN-UHFFFAOYSA-N 0.000 claims 1
- NPJBTLMUZORITB-QGZVFWFLSA-N 3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C(C=CC=C2C=3C=C(C=CC=3)C#N)=C2CC1 NPJBTLMUZORITB-QGZVFWFLSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- WJWTXHWEEDAGPF-UHFFFAOYSA-N 4-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]-n-propylbenzamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 WJWTXHWEEDAGPF-UHFFFAOYSA-N 0.000 claims 1
- DSPDNROSUXQSCT-UHFFFAOYSA-N 4-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 DSPDNROSUXQSCT-UHFFFAOYSA-N 0.000 claims 1
- UQIRATJNZOMMRO-UHFFFAOYSA-N 4-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]benzonitrile Chemical compound C1CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2C(=O)N1CCN1CCCC1 UQIRATJNZOMMRO-UHFFFAOYSA-N 0.000 claims 1
- DHFMLRJPFZHXON-UHFFFAOYSA-N 4-[1-oxo-2-(3-piperidin-1-ylpropyl)-3,4-dihydroisoquinolin-6-yl]benzonitrile Chemical compound C1CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2C(=O)N1CCCN1CCCCC1 DHFMLRJPFZHXON-UHFFFAOYSA-N 0.000 claims 1
- XVSGKDREUJXSJI-UHFFFAOYSA-N 4-[1-oxo-2-(3-pyrrolidin-1-ylpropyl)-3,4-dihydroisoquinolin-6-yl]benzonitrile Chemical compound C1CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2C(=O)N1CCCN1CCCC1 XVSGKDREUJXSJI-UHFFFAOYSA-N 0.000 claims 1
- GEKDFQFAAHBUSW-QGZVFWFLSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C(C=CC=C2C=3C=CC(=CC=3)C#N)=C2CC1 GEKDFQFAAHBUSW-QGZVFWFLSA-N 0.000 claims 1
- TXFFWCPTQAOPNJ-QGZVFWFLSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-6-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(=CC=3)C#N)C=C2CC1 TXFFWCPTQAOPNJ-QGZVFWFLSA-N 0.000 claims 1
- RBKYCZCNVBZBJX-QGZVFWFLSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-7-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2CC1 RBKYCZCNVBZBJX-QGZVFWFLSA-N 0.000 claims 1
- VKDSWJFAIIVEQX-MRXNPFEDSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3h-isoindol-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(=CC=3)C#N)C=C2C1 VKDSWJFAIIVEQX-MRXNPFEDSA-N 0.000 claims 1
- TXFFWCPTQAOPNJ-KRWDZBQOSA-N 4-[2-[2-[(2s)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-6-yl]benzonitrile Chemical compound C[C@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(=CC=3)C#N)C=C2CC1 TXFFWCPTQAOPNJ-KRWDZBQOSA-N 0.000 claims 1
- DKFXEXRXJSDLGU-UHFFFAOYSA-N 4-[[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]oxy]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 DKFXEXRXJSDLGU-UHFFFAOYSA-N 0.000 claims 1
- WEAMNIVNLBZRJQ-UHFFFAOYSA-N 4-[[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]oxy]benzonitrile Chemical compound C1CC2=CC(OC=3C=CC(=CC=3)C#N)=CC=C2C(=O)N1CCN1CCCC1 WEAMNIVNLBZRJQ-UHFFFAOYSA-N 0.000 claims 1
- JFKJRURGYVFQQJ-QGZVFWFLSA-N 4-[[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-6-yl]oxy]benzonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(OC=3C=CC(=CC=3)C#N)C=C2CC1 JFKJRURGYVFQQJ-QGZVFWFLSA-N 0.000 claims 1
- NEOVUCPJBUHDMO-GOSISDBHSA-N 4-[[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-6-yl]oxymethyl]benzonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(OCC=3C=CC(=CC=3)C#N)C=C2CC1 NEOVUCPJBUHDMO-GOSISDBHSA-N 0.000 claims 1
- XVVITBZYEYKSAH-UHFFFAOYSA-N 5-(benzimidazol-1-ylmethyl)-2-(2-pyrrolidin-1-ylethyl)-3h-isoindol-1-one Chemical compound C1C2=CC(CN3C4=CC=CC=C4N=C3)=CC=C2C(=O)N1CCN1CCCC1 XVVITBZYEYKSAH-UHFFFAOYSA-N 0.000 claims 1
- VSWIQVCFSZZKDR-UHFFFAOYSA-N 5-[[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]oxy]pyridine-2-carbonitrile Chemical compound C1CC2=CC(OC=3C=NC(=CC=3)C#N)=CC=C2C(=O)N1CCN1CCCC1 VSWIQVCFSZZKDR-UHFFFAOYSA-N 0.000 claims 1
- HUHFBMZFDZXFIC-MRXNPFEDSA-N 5-[[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-6-yl]oxy]pyridine-2-carbonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(OC=3C=NC(=CC=3)C#N)C=C2CC1 HUHFBMZFDZXFIC-MRXNPFEDSA-N 0.000 claims 1
- HTEJXYYZEOUJDH-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC(C=3C=C4OCOC4=CC=3)=CC=C2CN1CCN1CCCC1 HTEJXYYZEOUJDH-UHFFFAOYSA-N 0.000 claims 1
- IMZFMNPADUBNHA-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(C=3C=C4OCOC4=CC=3)=CC=C2C(=O)N1CCN1CCCC1 IMZFMNPADUBNHA-UHFFFAOYSA-N 0.000 claims 1
- WCDNIALSRDXDEO-UHFFFAOYSA-N 6-(1,3-dihydroisoindole-2-carbonyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1C2=CC=CC=C2CN1C(=O)C(C=C1CC2)=CC=C1C(=O)N2CCN1CCCC1 WCDNIALSRDXDEO-UHFFFAOYSA-N 0.000 claims 1
- DVTQVYYIBAQMQE-GOSISDBHSA-N 6-(1,3-dihydroisoindole-2-carbonyl)-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C(=O)N3CC4=CC=CC=C4C3)C=C2CC1 DVTQVYYIBAQMQE-GOSISDBHSA-N 0.000 claims 1
- GIHJOOARQXFDOP-UHFFFAOYSA-N 6-(2,4-difluorophenyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound FC1=CC(F)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 GIHJOOARQXFDOP-UHFFFAOYSA-N 0.000 claims 1
- LOXZVEKDMPWGAL-UHFFFAOYSA-N 6-(2-fluorophenyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound FC1=CC=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 LOXZVEKDMPWGAL-UHFFFAOYSA-N 0.000 claims 1
- GYCYFTUXIPKESF-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1=C(F)C(F)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 GYCYFTUXIPKESF-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200823204A (en) * | 2006-10-17 | 2008-06-01 | Arena Pharm Inc | Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto |
| GB0907284D0 (en) | 2009-04-28 | 2009-06-10 | Queen Mary & Westfield College | Compounds for inducing cellular apoptosis |
| RS56410B1 (sr) * | 2009-07-27 | 2018-01-31 | Gilead Sciences Inc | Fuzionisana heterociklična jedinjenja kao modulatori jonskih kanala |
| NZ604478A (en) | 2010-07-02 | 2014-12-24 | Gilead Sciences Inc | Fused heterocyclic compounds as ion channel modulators |
| WO2012058133A1 (en) * | 2010-10-29 | 2012-05-03 | Merck Sharp & Dohme Corp. | Isoindolinone pde10 inhibitors |
| ES2785475T3 (es) | 2011-05-10 | 2020-10-07 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores de canales iónicos |
| TWI478908B (zh) | 2011-07-01 | 2015-04-01 | Gilead Sciences Inc | 作為離子通道調節劑之稠合雜環化合物 |
| NO3175985T3 (enExample) | 2011-07-01 | 2018-04-28 | ||
| WO2013004652A1 (de) | 2011-07-04 | 2013-01-10 | Bayer Intellectual Property Gmbh | Verwendung substituierter isochinolinone, isochinolindione, isochinolintrione und dihydroisochinolinone oder jeweils deren salze als wirkstoffe gegen abiotischen pflanzenstress |
| WO2013076590A1 (en) | 2011-11-23 | 2013-05-30 | Oxygen Healthcare Research Pvt. Ltd | Benzothiazine compounds as h3 receptor ligands |
| CN105254554B (zh) * | 2014-07-14 | 2018-01-30 | 南开大学 | 一种制备异吲哚啉酮类化合物的方法 |
| BR112022020423A2 (pt) * | 2020-04-08 | 2022-11-29 | Remix Therapeutics Inc | Compostos e métodos para modulação de splicing |
| WO2022047260A1 (en) * | 2020-08-28 | 2022-03-03 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
| US12496297B1 (en) * | 2020-10-23 | 2025-12-16 | Washington University | Compositions of autophagy modulating agents and uses thereof |
| CN115819347B (zh) * | 2022-11-14 | 2024-08-30 | 暨明医药科技（苏州）有限公司 | 一种1-烷基-3-溴吡唑的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933829A (en) * | 1974-08-22 | 1976-01-20 | John Wyeth & Brother Limited | 4-Aminoquinoline derivatives |
| US4159331A (en) * | 1978-05-05 | 1979-06-26 | The Upjohn Company | Antihypertensive 4-aminoquinolines |
| US4166853A (en) * | 1978-05-05 | 1979-09-04 | The Upjohn Company | Antihypertensive 7-trifluoromethyl-4-aminoquinolones |
| IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| JP2001523256A (ja) * | 1997-05-01 | 2001-11-20 | イーライ・リリー・アンド・カンパニー | 抗血栓物質 |
| AU2002254114A1 (en) | 2001-03-23 | 2002-10-08 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
| US7381719B2 (en) * | 2002-09-19 | 2008-06-03 | Eli Lilly And Company | Diaryl ethers as opioid receptor antagonist |
| RS52436B (sr) * | 2004-05-14 | 2013-02-28 | Millennium Pharmaceuticals Inc. | Jedinjenja i postupci za inhibiciju napredovanja mitoze putem inhibicije aurora kinaze |
| US20060014733A1 (en) * | 2004-07-19 | 2006-01-19 | Pfizer Inc | Histamine-3 agonists and antagonists |
| US7381732B2 (en) * | 2004-10-26 | 2008-06-03 | Bristol-Myers Squibb Company | Pyrazolobenzamides and derivatives as factor Xa inhibitors |
| CA2595157A1 (en) * | 2005-01-21 | 2006-07-27 | Schering Corporation | Imidazole and benzimidazole derivatives useful as histamine h3 antagonists |
| US20070032475A1 (en) * | 2005-04-15 | 2007-02-08 | Ye Xiaocong M | Novel compounds useful for bradykinin B1 receptor antagonism |
-
2008
- 2008-09-11 US US12/208,794 patent/US20090069300A1/en not_active Abandoned
- 2008-09-11 AU AU2008298926A patent/AU2008298926A1/en not_active Abandoned
- 2008-09-11 MX MX2010002760A patent/MX2010002760A/es not_active Application Discontinuation
- 2008-09-11 JP JP2010524978A patent/JP2010539180A/ja not_active Withdrawn
- 2008-09-11 KR KR1020107007943A patent/KR20100054856A/ko not_active Ceased
- 2008-09-11 CN CN200880106892A patent/CN101848896A/zh active Pending
- 2008-09-11 AP AP2010005202A patent/AP2010005202A0/xx unknown
- 2008-09-11 CA CA2699384A patent/CA2699384A1/en not_active Abandoned
- 2008-09-11 EA EA201000316A patent/EA201000316A1/ru unknown
- 2008-09-11 BR BRPI0817061 patent/BRPI0817061A2/pt not_active Application Discontinuation
- 2008-09-11 WO PCT/US2008/075981 patent/WO2009036144A1/en not_active Ceased
- 2008-09-11 EP EP08799453A patent/EP2200989A1/en not_active Withdrawn
- 2008-09-12 CL CL200802726A patent/CL2008002726A1/es unknown
- 2008-09-12 TW TW097135281A patent/TW200927114A/zh unknown
- 2008-09-12 AR ARP080103964A patent/AR068423A1/es not_active Application Discontinuation
- 2008-09-12 PE PE2008001597A patent/PE20090651A1/es not_active Application Discontinuation
- 2008-09-12 PA PA20088795701A patent/PA8795701A1/es unknown
-
2010
- 2010-03-04 CR CR11303A patent/CR11303A/es not_active Application Discontinuation
- 2010-03-05 TN TNP2010000105A patent/TN2010000105A1/fr unknown
- 2010-03-10 EC EC2010010025A patent/ECSP10010025A/es unknown
- 2010-03-11 DO DO2010000079A patent/DOP2010000079A/es unknown
- 2010-03-11 NI NI201000036A patent/NI201000036A/es unknown
- 2010-03-11 ZA ZA2010/01751A patent/ZA201001751B/en unknown
- 2010-03-12 MA MA32688A patent/MA31699B1/fr unknown
- 2010-03-15 CO CO10030398A patent/CO6300955A2/es not_active Application Discontinuation
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