JP2010539180A5 - - Google Patents
Download PDFInfo
- 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- Withdrawn
Links
- -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
- VYWPYDHJBNEPBP-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound FC1=CC(F)=CC(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)=C1 VYWPYDHJBNEPBP-UHFFFAOYSA-N 0.000 claims 1
- WLSIIBHMNYNDNS-UHFFFAOYSA-N 6-(3-fluorophenyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound FC1=CC=CC(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)=C1 WLSIIBHMNYNDNS-UHFFFAOYSA-N 0.000 claims 1
- ZDFCXWNFABFQEW-UHFFFAOYSA-N 6-(4-fluorophenyl)-2-(2-piperidin-1-ylethyl)-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC(F)=CC=C1C1=CC=C(CN(CCN2CCCCC2)CC2)C2=C1 ZDFCXWNFABFQEW-UHFFFAOYSA-N 0.000 claims 1
- AEHCJYWMDQUABD-UHFFFAOYSA-N 6-(4-fluorophenyl)-2-(2-piperidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)N(CCN2CCCCC2)CC2)C2=C1 AEHCJYWMDQUABD-UHFFFAOYSA-N 0.000 claims 1
- GHRKTWSYAPPZEP-UHFFFAOYSA-N 6-(4-fluorophenyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 GHRKTWSYAPPZEP-UHFFFAOYSA-N 0.000 claims 1
- REFDYZWHMVDGRM-QGZVFWFLSA-N 6-(4-fluorophenyl)-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-3,4-dihydro-1h-isoquinoline Chemical compound C[C@@H]1CCCN1CCN1CC2=CC=C(C=3C=CC(F)=CC=3)C=C2CC1 REFDYZWHMVDGRM-QGZVFWFLSA-N 0.000 claims 1
- PESOUNLSPHQJGL-MRXNPFEDSA-N 6-(4-fluorophenyl)-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(F)=CC=3)C=C2CC1 PESOUNLSPHQJGL-MRXNPFEDSA-N 0.000 claims 1
- PESOUNLSPHQJGL-INIZCTEOSA-N 6-(4-fluorophenyl)-2-[2-[(2s)-2-methylpyrrolidin-1-yl]ethyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(F)=CC=3)C=C2CC1 PESOUNLSPHQJGL-INIZCTEOSA-N 0.000 claims 1
- DIQPFOSOOFNUQW-UHFFFAOYSA-N 6-(4-methoxyphenyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 DIQPFOSOOFNUQW-UHFFFAOYSA-N 0.000 claims 1
- VKZKSELGBRDDRN-UHFFFAOYSA-N 6-(4-methylsulfonylphenyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 VKZKSELGBRDDRN-UHFFFAOYSA-N 0.000 claims 1
- BPNWHQZDCCBREC-GOSISDBHSA-N 6-(azepan-1-yl)-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(N3CCCCCC3)C=C2CC1 BPNWHQZDCCBREC-GOSISDBHSA-N 0.000 claims 1
- GPBFLYUZYFABML-GOSISDBHSA-N 6-(azepane-1-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)N3CCCCCC3)C=C2CC1 GPBFLYUZYFABML-GOSISDBHSA-N 0.000 claims 1
- BTHDBDIXZQYFMB-UHFFFAOYSA-N 6-(benzimidazol-1-yl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(N3C4=CC=CC=C4N=C3)=CC=C2C(=O)N1CCN1CCCC1 BTHDBDIXZQYFMB-UHFFFAOYSA-N 0.000 claims 1
- NSSMXABOIJRQRP-QGZVFWFLSA-N 6-(benzimidazol-1-yl)-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(N3C4=CC=CC=C4N=C3)C=C2CC1 NSSMXABOIJRQRP-QGZVFWFLSA-N 0.000 claims 1
- QZGVPLQPUBNUMV-UHFFFAOYSA-N 6-(piperidine-1-carbonyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C2C(=O)N(CCN3CCCC3)CCC2=CC=1C(=O)N1CCCCC1 QZGVPLQPUBNUMV-UHFFFAOYSA-N 0.000 claims 1
- BXBHVUTUDLRKMI-UHFFFAOYSA-N 6-(pyrrolidine-1-carbonyl)-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C2C(=O)N(CCN3CCCC3)CCC2=CC=1C(=O)N1CCCC1 BXBHVUTUDLRKMI-UHFFFAOYSA-N 0.000 claims 1
- MEWSMJAOOPXCMF-UHFFFAOYSA-N 6-[2-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound FC1=CC(C(=O)N2CCCC2)=CC=C1C(C=C1CC2)=CC=C1C(=O)N2CCN1CCCC1 MEWSMJAOOPXCMF-UHFFFAOYSA-N 0.000 claims 1
- TYGMGAZPXWLANI-UHFFFAOYSA-N 6-[3-chloro-4-(pyrrolidine-1-carbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound ClC1=CC(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)=CC=C1C(=O)N1CCCC1 TYGMGAZPXWLANI-UHFFFAOYSA-N 0.000 claims 1
- PSOYZSZZNCJMRX-UHFFFAOYSA-N 6-[3-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound FC1=CC(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)=CC=C1C(=O)N1CCCC1 PSOYZSZZNCJMRX-UHFFFAOYSA-N 0.000 claims 1
- AVXJIYHIOLMDHB-UHFFFAOYSA-N 6-[4-(3-methoxypyrrolidine-1-carbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1C(OC)CCN1C(=O)C1=CC=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=C1 AVXJIYHIOLMDHB-UHFFFAOYSA-N 0.000 claims 1
- ZZWWPCHANMIGSS-UHFFFAOYSA-N 6-[4-(azetidine-1-carbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=CC=1C(=O)N1CCC1 ZZWWPCHANMIGSS-UHFFFAOYSA-N 0.000 claims 1
- YXVYVEQLGFEDLP-LJQANCHMSA-N 6-[4-(azetidine-1-carbonyl)phenyl]-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C=3C=CC(=CC=3)C(=O)N3CCC3)C=C2CC1 YXVYVEQLGFEDLP-LJQANCHMSA-N 0.000 claims 1
- IXGOGVFDYFVFOF-UHFFFAOYSA-N 6-[4-(cyclopropanecarbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=CC=1C(=O)C1CC1 IXGOGVFDYFVFOF-UHFFFAOYSA-N 0.000 claims 1
- SOGOTVMZEUKLOJ-UHFFFAOYSA-N 6-[4-(morpholine-4-carbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=CC=1C(=O)N1CCOCC1 SOGOTVMZEUKLOJ-UHFFFAOYSA-N 0.000 claims 1
- FTJQBQMPWIVAQU-UHFFFAOYSA-N 6-[4-(piperidine-1-carbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=CC=1C(=O)N1CCCCC1 FTJQBQMPWIVAQU-UHFFFAOYSA-N 0.000 claims 1
- KZBOXUSQBLHAAK-UHFFFAOYSA-N 6-[4-(pyrrolidine-1-carbonyl)phenoxy]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(OC=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=CC=1C(=O)N1CCCC1 KZBOXUSQBLHAAK-UHFFFAOYSA-N 0.000 claims 1
- JHNSCZQKUPKIMZ-UHFFFAOYSA-N 6-[4-(pyrrolidine-1-carbonyl)phenyl]-2-(3-pyrrolidin-1-ylpropyl)-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(C=2C=C3CCN(CCCN4CCCC4)C(=O)C3=CC=2)C=CC=1C(=O)N1CCCC1 JHNSCZQKUPKIMZ-UHFFFAOYSA-N 0.000 claims 1
- QKNQLRSRULGFBA-HXUWFJFHSA-N 6-[4-[(2r)-2-methylpyrrolidine-1-carbonyl]phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C[C@@H]1CCCN1C(=O)C1=CC=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=C1 QKNQLRSRULGFBA-HXUWFJFHSA-N 0.000 claims 1
- HLTWIRAJTFHHKP-VWLOTQADSA-N 6-[4-[(2s)-2-(methoxymethyl)pyrrolidine-1-carbonyl]phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound COC[C@@H]1CCCN1C(=O)C1=CC=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=C1 HLTWIRAJTFHHKP-VWLOTQADSA-N 0.000 claims 1
- BTIBJMKJNQUNFA-RLWLMLJZSA-N 6-[4-[(2s)-2-(methoxymethyl)pyrrolidine-1-carbonyl]phenyl]-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-3,4-dihydroisoquinolin-1-one Chemical compound COC[C@@H]1CCCN1C(=O)C1=CC=C(C=2C=C3CCN(CCN4[C@@H](CCC4)C)C(=O)C3=CC=2)C=C1 BTIBJMKJNQUNFA-RLWLMLJZSA-N 0.000 claims 1
- QKNQLRSRULGFBA-FQEVSTJZSA-N 6-[4-[(2s)-2-methylpyrrolidine-1-carbonyl]phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C[C@H]1CCCN1C(=O)C1=CC=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=C1 QKNQLRSRULGFBA-FQEVSTJZSA-N 0.000 claims 1
- FNNSZXVZZPJSLH-UHFFFAOYSA-N 6-[4-fluoro-3-(pyrrolidine-1-carbonyl)phenyl]-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound FC1=CC=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=C1C(=O)N1CCCC1 FNNSZXVZZPJSLH-UHFFFAOYSA-N 0.000 claims 1
- WJSMRXZBXLZTEH-UHFFFAOYSA-N 6-[[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]oxy]pyridine-3-carbonitrile Chemical compound C1CC2=CC(OC=3N=CC(=CC=3)C#N)=CC=C2C(=O)N1CCN1CCCC1 WJSMRXZBXLZTEH-UHFFFAOYSA-N 0.000 claims 1
- VCQCSXTXOSODCY-MRXNPFEDSA-N 6-[[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinolin-6-yl]oxy]pyridine-3-carbonitrile Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(OC=3N=CC(=CC=3)C#N)C=C2CC1 VCQCSXTXOSODCY-MRXNPFEDSA-N 0.000 claims 1
- IWUGHHQMBCOMOV-UHFFFAOYSA-N 6-indazol-1-yl-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(N3C4=CC=CC=C4C=N3)=CC=C2C(=O)N1CCN1CCCC1 IWUGHHQMBCOMOV-UHFFFAOYSA-N 0.000 claims 1
- GSAGTJUQXZNCBN-UHFFFAOYSA-N 6-phenyl-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(C=3C=CC=CC=3)=CC=C2C(=O)N1CCN1CCCC1 GSAGTJUQXZNCBN-UHFFFAOYSA-N 0.000 claims 1
- WNHAEBNVEXIILO-UHFFFAOYSA-N 6-piperidin-1-yl-2-(2-piperidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(N3CCCCC3)=CC=C2C(=O)N1CCN1CCCCC1 WNHAEBNVEXIILO-UHFFFAOYSA-N 0.000 claims 1
- LHTGPDWLAXLFNE-UHFFFAOYSA-N 6-piperidin-1-yl-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(N3CCCCC3)=CC=C2C(=O)N1CCN1CCCC1 LHTGPDWLAXLFNE-UHFFFAOYSA-N 0.000 claims 1
- LXRHFSAOTQKITL-UHFFFAOYSA-N 6-pyrazol-1-yl-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(N3N=CC=C3)=CC=C2C(=O)N1CCN1CCCC1 LXRHFSAOTQKITL-UHFFFAOYSA-N 0.000 claims 1
- OYOUUSCAVHSQKA-UHFFFAOYSA-N 6-pyridin-4-yl-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC(C=3C=CN=CC=3)=CC=C2C(=O)N1CCN1CCCC1 OYOUUSCAVHSQKA-UHFFFAOYSA-N 0.000 claims 1
- 208000031091 Amnestic disease Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- POFFMFZFCINKAN-QGZVFWFLSA-N C(C1=CC=CC=C1)(=O)NC1=CC=C2CCN(C(C2=C1)=O)CCN1[C@@H](CCC1)C Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=C2CCN(C(C2=C1)=O)CCN1[C@@H](CCC1)C POFFMFZFCINKAN-QGZVFWFLSA-N 0.000 claims 1
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 1
- 206010012218 Delirium Diseases 0.000 claims 1
- 208000012239 Developmental disease Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 1
- 206010033864 Paranoia Diseases 0.000 claims 1
- 208000027099 Paranoid disease Diseases 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 210000001766 X chromosome Anatomy 0.000 claims 1
- DLTVEUZATGGLPH-NRFANRHFSA-N [(2s)-2-methylpyrrolidin-1-yl]-[4-[2-(2-pyrrolidin-1-ylethyl)-3,4-dihydro-1h-isoquinolin-6-yl]phenyl]methanone Chemical compound C[C@H]1CCCN1C(=O)C1=CC=C(C=2C=C3CCN(CCN4CCCC4)CC3=CC=2)C=C1 DLTVEUZATGGLPH-NRFANRHFSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000013677 cerebrovascular dementia Diseases 0.000 claims 1
- 230000006999 cognitive decline Effects 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 125000004802 cyanophenyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010013932 dyslexia Diseases 0.000 claims 1
- 230000006870 function Effects 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 229960001340 histamine Drugs 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 230000010354 integration Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- LKTBYJWWCWTBPL-UHFFFAOYSA-N methyl 4-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 LKTBYJWWCWTBPL-UHFFFAOYSA-N 0.000 claims 1
- 229940095102 methyl benzoate Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- ABAUQRQEOVFAGR-UHFFFAOYSA-N morpholin-4-yl-[4-[2-(2-pyrrolidin-1-ylethyl)-3,4-dihydro-1h-isoquinolin-6-yl]phenyl]methanone Chemical compound C=1C=C(C=2C=C3CCN(CCN4CCCC4)CC3=CC=2)C=CC=1C(=O)N1CCOCC1 ABAUQRQEOVFAGR-UHFFFAOYSA-N 0.000 claims 1
- XKDHGBLTUPENCN-MRXNPFEDSA-N n-cyclopentyl-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-oxo-3,4-dihydroisoquinoline-6-carboxamide Chemical compound C[C@@H]1CCCN1CCN1C(=O)C2=CC=C(C(=O)NC3CCCC3)C=C2CC1 XKDHGBLTUPENCN-MRXNPFEDSA-N 0.000 claims 1
- WZHAQWFZACLGKI-UHFFFAOYSA-N n-cyclopentyl-4-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]benzamide Chemical compound C=1C=C(C=2C=C3CCN(CCN4CCCC4)C(=O)C3=CC=2)C=CC=1C(=O)NC1CCCC1 WZHAQWFZACLGKI-UHFFFAOYSA-N 0.000 claims 1
- ZOYRJBIULHDHMS-UHFFFAOYSA-N n-methoxy-n-methyl-4-[1-oxo-2-(2-pyrrolidin-1-ylethyl)-3,4-dihydroisoquinolin-6-yl]benzamide Chemical compound C1=CC(C(=O)N(C)OC)=CC=C1C1=CC=C(C(=O)N(CCN2CCCC2)CC2)C2=C1 ZOYRJBIULHDHMS-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- WKAXMZCFRUWWKL-UHFFFAOYSA-N piperidin-1-yl-[4-[2-(2-pyrrolidin-1-ylethyl)-3,4-dihydro-1h-isoquinolin-6-yl]phenyl]methanone Chemical compound C=1C=C(C=2C=C3CCN(CCN4CCCC4)CC3=CC=2)C=CC=1C(=O)N1CCCCC1 WKAXMZCFRUWWKL-UHFFFAOYSA-N 0.000 claims 1
- JIDHIDSOIJOIKM-UHFFFAOYSA-N pyrrolidin-1-yl-[4-[2-(2-pyrrolidin-1-ylethyl)-3,4-dihydro-1h-isoquinolin-6-yl]phenyl]methanone Chemical compound C=1C=C(C=2C=C3CCN(CCN4CCCC4)CC3=CC=2)C=CC=1C(=O)N1CCCC1 JIDHIDSOIJOIKM-UHFFFAOYSA-N 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000009529 traumatic brain injury Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99363607P | 2007-09-12 | 2007-09-12 | |
| PCT/US2008/075981 WO2009036144A1 (en) | 2007-09-12 | 2008-09-11 | Isoquinolinyl and isoindolinyl derivatives as histamine-3 antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010539180A JP2010539180A (ja) | 2010-12-16 |
| JP2010539180A5 true JP2010539180A5 (OSRAM) | 2011-09-29 |
Family
ID=40261509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010524978A Withdrawn JP2010539180A (ja) | 2007-09-12 | 2008-09-11 | ヒスタミン３拮抗薬としてのイソキノリニルおよびイソインドリニル誘導体 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US20090069300A1 (OSRAM) |
| EP (1) | EP2200989A1 (OSRAM) |
| JP (1) | JP2010539180A (OSRAM) |
| KR (1) | KR20100054856A (OSRAM) |
| CN (1) | CN101848896A (OSRAM) |
| AP (1) | AP2010005202A0 (OSRAM) |
| AR (1) | AR068423A1 (OSRAM) |
| AU (1) | AU2008298926A1 (OSRAM) |
| BR (1) | BRPI0817061A2 (OSRAM) |
| CA (1) | CA2699384A1 (OSRAM) |
| CL (1) | CL2008002726A1 (OSRAM) |
| CO (1) | CO6300955A2 (OSRAM) |
| CR (1) | CR11303A (OSRAM) |
| DO (1) | DOP2010000079A (OSRAM) |
| EA (1) | EA201000316A1 (OSRAM) |
| EC (1) | ECSP10010025A (OSRAM) |
| MA (1) | MA31699B1 (OSRAM) |
| MX (1) | MX2010002760A (OSRAM) |
| NI (1) | NI201000036A (OSRAM) |
| PA (1) | PA8795701A1 (OSRAM) |
| PE (1) | PE20090651A1 (OSRAM) |
| TN (1) | TN2010000105A1 (OSRAM) |
| TW (1) | TW200927114A (OSRAM) |
| WO (1) | WO2009036144A1 (OSRAM) |
| ZA (1) | ZA201001751B (OSRAM) |
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 |
| SMT201700456T1 (it) | 2009-07-27 | 2017-11-15 | Gilead Sciences Inc | Composti eterociclici fusi come modulatori dei canali ionici |
| JP5858586B2 (ja) | 2010-07-02 | 2016-02-10 | ギリアード サイエンシーズ， インコーポレイテッド | イオンチャネルモジュレーターとしての縮合複素環式化合物 |
| US20130203756A1 (en) * | 2010-10-29 | 2013-08-08 | Jamie L. Bunda | Isoindoline pde10 inhibitors |
| TWI577670B (zh) | 2011-05-10 | 2017-04-11 | 基利科學股份有限公司 | 充當離子通道調節劑之稠合雜環化合物 |
| 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 (OSRAM) | 2011-07-01 | 2018-04-28 | ||
| US9173395B2 (en) | 2011-07-04 | 2015-11-03 | Bayer Intellectual Property Gmbh | Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants |
| 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 |
| TW202208344A (zh) * | 2020-04-08 | 2022-03-01 | 美商雷密克斯醫療公司 | 調節剪接之化合物及方法 |
| AU2021331492A1 (en) | 2020-08-28 | 2023-04-13 | 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 |
| CA2287984A1 (en) * | 1997-05-01 | 1998-11-05 | Gerald Floyd Smith | Antithrombotic agents |
| WO2002076925A2 (en) | 2001-03-23 | 2002-10-03 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
| ES2392200T3 (es) * | 2002-09-19 | 2012-12-05 | Eli Lilly & Company | Ésteres de diarilo como antagonistas del receptor opiáceo |
| EP2261226B1 (en) * | 2004-05-14 | 2015-04-01 | Millennium Pharmaceuticals, Inc. | Methods for preparing aurora kinase inhibitors |
| 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 |
| CN101107231A (zh) * | 2005-01-21 | 2008-01-16 | 先灵公司 | 用作组胺h3拮抗剂的咪唑和苯并咪唑衍生物 |
| US20070032475A1 (en) * | 2005-04-15 | 2007-02-08 | Ye Xiaocong M | Novel compounds useful for bradykinin B1 receptor antagonism |
-
2008
- 2008-09-11 EA EA201000316A patent/EA201000316A1/ru unknown
- 2008-09-11 BR BRPI0817061 patent/BRPI0817061A2/pt not_active Application Discontinuation
- 2008-09-11 AU AU2008298926A patent/AU2008298926A1/en not_active Abandoned
- 2008-09-11 WO PCT/US2008/075981 patent/WO2009036144A1/en not_active Ceased
- 2008-09-11 KR KR1020107007943A patent/KR20100054856A/ko not_active Ceased
- 2008-09-11 AP AP2010005202A patent/AP2010005202A0/xx unknown
- 2008-09-11 EP EP08799453A patent/EP2200989A1/en not_active Withdrawn
- 2008-09-11 MX MX2010002760A patent/MX2010002760A/es not_active Application Discontinuation
- 2008-09-11 CN CN200880106892A patent/CN101848896A/zh active Pending
- 2008-09-11 JP JP2010524978A patent/JP2010539180A/ja not_active Withdrawn
- 2008-09-11 US US12/208,794 patent/US20090069300A1/en not_active Abandoned
- 2008-09-11 CA CA2699384A patent/CA2699384A1/en not_active Abandoned
- 2008-09-12 PE PE2008001597A patent/PE20090651A1/es not_active Application Discontinuation
- 2008-09-12 AR ARP080103964A patent/AR068423A1/es not_active Application Discontinuation
- 2008-09-12 TW TW097135281A patent/TW200927114A/zh unknown
- 2008-09-12 PA PA20088795701A patent/PA8795701A1/es unknown
- 2008-09-12 CL CL200802726A patent/CL2008002726A1/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 ZA ZA2010/01751A patent/ZA201001751B/en unknown
- 2010-03-11 NI NI201000036A patent/NI201000036A/es unknown
- 2010-03-12 MA MA32688A patent/MA31699B1/fr unknown
- 2010-03-15 CO CO10030398A patent/CO6300955A2/es not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010539180A5 (OSRAM) | ||
| JP6298115B2 (ja) | Ｌｒｒｋ２調節薬としてのピラゾールアミノピリミジン誘導体 | |
| US10519137B2 (en) | Pyrazolyl quinoxaline kinase inhibitors | |
| JP2017500364A5 (OSRAM) | ||
| JP5759470B2 (ja) | オレキシン受容体調節因子としての二置換オクタヒドロピロロ［３，４−ｃ］ピロール | |
| RU2015122414A (ru) | Соединения n-пирролидинилмочевины, n'-пиразолилмочевины, тиомочевины, гуанидина и цианогуанидина как ингибиторы киназы trka | |
| RU2015132181A (ru) | Фтор-[1,3]-оксазины в качестве ингибиторов васе1 | |
| JP2011518836A5 (OSRAM) | ||
| CA2567662A1 (en) | Compounds and compositions as protein kinase inhibitors | |
| JP2010510319A5 (OSRAM) | ||
| JP2020505454A5 (OSRAM) | ||
| JP2019519484A5 (OSRAM) | ||
| RU2016133684A (ru) | Бициклические азот-содержащие соединения как агонисты М1 мускариновых рецепторов | |
| JP2010539180A (ja) | ヒスタミン３拮抗薬としてのイソキノリニルおよびイソインドリニル誘導体 | |
| KR102082331B1 (ko) | Cot 조정제로서의 6-아미노-퀴놀린-3-카르보니트릴 | |
| JP2013519733A5 (OSRAM) | ||
| JP2014517833A5 (OSRAM) | ||
| RU2017124425A (ru) | Производные 2,4-диоксо-хиназолин-6-сульфонамида в качестве ингибиторов parg | |
| JP2015514072A5 (OSRAM) | ||
| JP2013510876A5 (OSRAM) | ||
| CA2671744A1 (en) | Compounds and compositions as protein kinase inhibitors | |
| RU2018142987A (ru) | Положительные аллостерические модуляторы мускаринового ацетилхолинового рецептора m4 | |
| JP2014528446A5 (OSRAM) | ||
| JP2007523152A5 (OSRAM) | ||
| WO2015152367A1 (ja) | オキソ複素環誘導体 |