JP2008509955A5 - - Google Patents
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- Publication number
- JP2008509955A5 JP2008509955A5 JP2007526371A JP2007526371A JP2008509955A5 JP 2008509955 A5 JP2008509955 A5 JP 2008509955A5 JP 2007526371 A JP2007526371 A JP 2007526371A JP 2007526371 A JP2007526371 A JP 2007526371A JP 2008509955 A5 JP2008509955 A5 JP 2008509955A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tetrahydro
- cyclobutyl
- benzazepin
- heteroaryl
- 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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- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- -1 cyano, amino Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- OZVJGCNGTOCMDY-UHFFFAOYSA-N 1-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)NC)=CN1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 OZVJGCNGTOCMDY-UHFFFAOYSA-N 0.000 claims 1
- LYCGOHZEXHRSEG-UHFFFAOYSA-N 1-[4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]phenyl]pyrrolidin-2-one Chemical compound O=C1CCCN1C(C=C1)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 LYCGOHZEXHRSEG-UHFFFAOYSA-N 0.000 claims 1
- YQZIMSVEJPTIIF-UHFFFAOYSA-N 1-[4-[(3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]phenyl]pyrrolidin-2-one Chemical compound O=C1CCCN1C(C=C1)=CC=C1CC1=CC=C(CCN(CC2)C3CCCC3)C2=C1 YQZIMSVEJPTIIF-UHFFFAOYSA-N 0.000 claims 1
- NSJBQUKUADYKOX-UHFFFAOYSA-N 1-[5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyrazin-2-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C(N=C1)=CN=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 NSJBQUKUADYKOX-UHFFFAOYSA-N 0.000 claims 1
- HCTIOBOUIVYAGI-UHFFFAOYSA-N 1-[5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-2-yl]-3-methylimidazolidin-2-one Chemical compound O=C1N(C)CCN1C(N=C1)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 HCTIOBOUIVYAGI-UHFFFAOYSA-N 0.000 claims 1
- OVYFOEMMKCCEMC-UHFFFAOYSA-N 1-[5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-2-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C(N=C1)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 OVYFOEMMKCCEMC-UHFFFAOYSA-N 0.000 claims 1
- HAVWYPZNIYDKOG-UHFFFAOYSA-N 1-[5-[(3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-2-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C(N=C1)=CC=C1CC1=CC=C(CCN(CC2)C3CCCC3)C2=C1 HAVWYPZNIYDKOG-UHFFFAOYSA-N 0.000 claims 1
- XUJOWYHFLDSWBM-UHFFFAOYSA-N 1-[6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-3-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C(C=N1)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 XUJOWYHFLDSWBM-UHFFFAOYSA-N 0.000 claims 1
- MWKDMLMOHSLISU-UHFFFAOYSA-N 3-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-methylimidazole-4-carboxamide Chemical compound CNC(=O)C1=CN=CN1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 MWKDMLMOHSLISU-UHFFFAOYSA-N 0.000 claims 1
- DRFASFBKVNYHCH-UHFFFAOYSA-N 3-[4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]phenyl]-2h-1,2,4-oxadiazol-5-one Chemical compound N1OC(=O)N=C1C(C=C1)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 DRFASFBKVNYHCH-UHFFFAOYSA-N 0.000 claims 1
- UHOYFUZUSCIXIR-UHFFFAOYSA-N 3-[5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-2-yl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C(N=C1)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 UHOYFUZUSCIXIR-UHFFFAOYSA-N 0.000 claims 1
- GMIGMRISMPGWON-UHFFFAOYSA-N 3-cyclobutyl-7-(pyrazin-2-ylmethyl)-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C=1N=CC=NC=1CC(C=C1CC2)=CC=C1CCN2C1CCC1 GMIGMRISMPGWON-UHFFFAOYSA-N 0.000 claims 1
- BJKVWBLBHOPOPV-UHFFFAOYSA-N 3-cyclobutyl-7-[(4-pyrazol-1-ylphenyl)methyl]-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1CC(C=C1)=CC=C1N1C=CC=N1 BJKVWBLBHOPOPV-UHFFFAOYSA-N 0.000 claims 1
- VWRAFRMDDHKIEP-UHFFFAOYSA-N 3-cyclobutyl-7-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1CC(C=C1)=CC=C1N1C=NC=N1 VWRAFRMDDHKIEP-UHFFFAOYSA-N 0.000 claims 1
- VUXUBNIGSMDJBP-UHFFFAOYSA-N 4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 VUXUBNIGSMDJBP-UHFFFAOYSA-N 0.000 claims 1
- DUIUKCKAGDAJPY-UHFFFAOYSA-N 4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 DUIUKCKAGDAJPY-UHFFFAOYSA-N 0.000 claims 1
- AIQNRPGDHDIKTK-UHFFFAOYSA-N 4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 AIQNRPGDHDIKTK-UHFFFAOYSA-N 0.000 claims 1
- PUXLLBMFGVBZQP-UHFFFAOYSA-N 4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 PUXLLBMFGVBZQP-UHFFFAOYSA-N 0.000 claims 1
- USTNOVQFGOFMTA-UHFFFAOYSA-N 4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 USTNOVQFGOFMTA-UHFFFAOYSA-N 0.000 claims 1
- TVAKYGOSGKIYQR-UHFFFAOYSA-N 4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 TVAKYGOSGKIYQR-UHFFFAOYSA-N 0.000 claims 1
- CYPHJRCYACZFJL-UHFFFAOYSA-N 4-[4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]phenyl]thiadiazole Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1CC(C=C1)=CC=C1C1=CSN=N1 CYPHJRCYACZFJL-UHFFFAOYSA-N 0.000 claims 1
- FYUBPMWGGAMNGJ-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methoxy]-n-methylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CN=C1OCC1=CC=C(CCN(CC2)C3CCC3)C2=C1 FYUBPMWGGAMNGJ-UHFFFAOYSA-N 0.000 claims 1
- ZXVRCYJEMOYKEA-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n,n-dimethylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)N(C)C)=CN=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 ZXVRCYJEMOYKEA-UHFFFAOYSA-N 0.000 claims 1
- SMLYDZAHCUEOEF-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-(2,2,2-trifluoroethyl)pyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NCC(F)(F)F)=CN=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 SMLYDZAHCUEOEF-UHFFFAOYSA-N 0.000 claims 1
- QUJAQIXONOSQML-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-(oxan-4-yl)pyridine-2-carboxamide Chemical compound C=1C=C(CC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NC=1C(=O)NC1CCOCC1 QUJAQIXONOSQML-UHFFFAOYSA-N 0.000 claims 1
- WYTGMSYLGSQVRL-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-methylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CN=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 WYTGMSYLGSQVRL-UHFFFAOYSA-N 0.000 claims 1
- MAGYJUUFQCTFGG-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 MAGYJUUFQCTFGG-UHFFFAOYSA-N 0.000 claims 1
- VVPXNXYWURAXRV-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-propan-2-ylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC(C)C)=CN=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 VVPXNXYWURAXRV-UHFFFAOYSA-N 0.000 claims 1
- AMPPEJGVVFMNSO-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-propan-2-ylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC(C)C)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 AMPPEJGVVFMNSO-UHFFFAOYSA-N 0.000 claims 1
- GGWPNQXOPSTPDZ-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyrazine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CN=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 GGWPNQXOPSTPDZ-UHFFFAOYSA-N 0.000 claims 1
- MRXSBHAOCMBNKP-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 MRXSBHAOCMBNKP-UHFFFAOYSA-N 0.000 claims 1
- MKSSXOVDQMSLAG-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 MKSSXOVDQMSLAG-UHFFFAOYSA-N 0.000 claims 1
- GGFWKXWSICGNEB-UHFFFAOYSA-N 5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 GGFWKXWSICGNEB-UHFFFAOYSA-N 0.000 claims 1
- XKEGECUDELZRMU-UHFFFAOYSA-N 5-[(3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methoxy]-n-methylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CN=C1OCC1=CC=C(CCN(CC2)C3CCCC3)C2=C1 XKEGECUDELZRMU-UHFFFAOYSA-N 0.000 claims 1
- DAGDBFMXJNBYTN-UHFFFAOYSA-N 5-[(3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-methylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CN=C1CC1=CC=C(CCN(CC2)C3CCCC3)C2=C1 DAGDBFMXJNBYTN-UHFFFAOYSA-N 0.000 claims 1
- ZPMWFZGSLGAICJ-UHFFFAOYSA-N 5-[4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]phenyl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2C=CC(CC=3C=C4CCN(CCC4=CC=3)C3CCC3)=CC=2)=N1 ZPMWFZGSLGAICJ-UHFFFAOYSA-N 0.000 claims 1
- FQGOZSLBGMBCJC-UHFFFAOYSA-N 5-[5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyrazin-2-yl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2N=CC(CC=3C=C4CCN(CCC4=CC=3)C3CCC3)=NC=2)=N1 FQGOZSLBGMBCJC-UHFFFAOYSA-N 0.000 claims 1
- SWRCTQGLYZLFGD-UHFFFAOYSA-N 5-[5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-2-yl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2N=CC(CC=3C=C4CCN(CCC4=CC=3)C3CCC3)=CC=2)=N1 SWRCTQGLYZLFGD-UHFFFAOYSA-N 0.000 claims 1
- GSEANIAQOPZRDB-UHFFFAOYSA-N 5-[6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-3-yl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2C=NC(CC=3C=C4CCN(CCC4=CC=3)C3CCC3)=CC=2)=N1 GSEANIAQOPZRDB-UHFFFAOYSA-N 0.000 claims 1
- UDJPVVXXHFVKBZ-UHFFFAOYSA-N 6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methoxy]-n-methylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NC)=CC=C1OCC1=CC=C(CCN(CC2)C3CCC3)C2=C1 UDJPVVXXHFVKBZ-UHFFFAOYSA-N 0.000 claims 1
- ABVFLGMOGPBRQR-UHFFFAOYSA-N 6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methoxy]-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1OCC1=CC=C(CCN(CC2)C3CCC3)C2=C1 ABVFLGMOGPBRQR-UHFFFAOYSA-N 0.000 claims 1
- NTXLDMWMZCHZLJ-UHFFFAOYSA-N 6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 NTXLDMWMZCHZLJ-UHFFFAOYSA-N 0.000 claims 1
- VDNXDJHYMQPAHK-UHFFFAOYSA-N 6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridine-3-carbonitrile Chemical compound N1=CC(C#N)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 VDNXDJHYMQPAHK-UHFFFAOYSA-N 0.000 claims 1
- QMKGVANSKAQRNJ-UHFFFAOYSA-N 6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 QMKGVANSKAQRNJ-UHFFFAOYSA-N 0.000 claims 1
- QIDSSWVUMTZYQM-UHFFFAOYSA-N 6-[(3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methoxy]-n-methylpyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NC)=CC=C1OCC1=CC=C(CCN(CC2)C3CCCC3)C2=C1 QIDSSWVUMTZYQM-UHFFFAOYSA-N 0.000 claims 1
- FDRABQXESINLQL-UHFFFAOYSA-N 6-[(3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methoxy]-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1OCC1=CC=C(CCN(CC2)C3CCCC3)C2=C1 FDRABQXESINLQL-UHFFFAOYSA-N 0.000 claims 1
- WDNDBAZKABPSKR-UHFFFAOYSA-N 7-[(5-bromopyridin-2-yl)methyl]-3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound N1=CC(Br)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 WDNDBAZKABPSKR-UHFFFAOYSA-N 0.000 claims 1
- ICYLXHGEIRUWSR-UHFFFAOYSA-N 7-[(6-bromopyridin-3-yl)methyl]-3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1=NC(Br)=CC=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 ICYLXHGEIRUWSR-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- NKEHVZDOPKIKDJ-UHFFFAOYSA-N [4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C(CC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=CC=1C(=O)N1CCOCC1 NKEHVZDOPKIKDJ-UHFFFAOYSA-N 0.000 claims 1
- XVXQKGMSQPOHEZ-UHFFFAOYSA-N [4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]phenyl]-piperidin-1-ylmethanone Chemical compound C=1C=C(CC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=CC=1C(=O)N1CCCCC1 XVXQKGMSQPOHEZ-UHFFFAOYSA-N 0.000 claims 1
- KFNISZNONWEFKF-UHFFFAOYSA-N [4-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(CC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=CC=1C(=O)N1CCCC1 KFNISZNONWEFKF-UHFFFAOYSA-N 0.000 claims 1
- BJITZALZDGZTSN-UHFFFAOYSA-N [5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyrazin-2-yl]-pyrrolidin-1-ylmethanone Chemical compound C=1N=C(CC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NC=1C(=O)N1CCCC1 BJITZALZDGZTSN-UHFFFAOYSA-N 0.000 claims 1
- UJPSFYAPGWAQQR-UHFFFAOYSA-N [5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-2-yl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(CC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NC=1C(=O)N1CCCC1 UJPSFYAPGWAQQR-UHFFFAOYSA-N 0.000 claims 1
- KYBYTZZTQSZJBH-UHFFFAOYSA-N [6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(CC=2C=C3CCN(CCC3=CC=2)C2CCC2)N=CC=1C(=O)N1CCCC1 KYBYTZZTQSZJBH-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000000911 decarboxylating effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- DPTPSTVVCHAKGB-UHFFFAOYSA-N n-(4-cyanophenyl)-5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyridine-2-carboxamide Chemical compound C=1C=C(CC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NC=1C(=O)NC1=CC=C(C#N)C=C1 DPTPSTVVCHAKGB-UHFFFAOYSA-N 0.000 claims 1
- JRXHVZVRUJVHMO-UHFFFAOYSA-N n-(cyanomethyl)-5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyrazine-2-carboxamide Chemical compound C1=NC(C(NCC#N)=O)=CN=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 JRXHVZVRUJVHMO-UHFFFAOYSA-N 0.000 claims 1
- DRIXLHFDXKXDAX-UHFFFAOYSA-N n-[5-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)methyl]pyrazin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CN=C1CC1=CC=C(CCN(CC2)C3CCC3)C2=C1 DRIXLHFDXKXDAX-UHFFFAOYSA-N 0.000 claims 1
- ZATFGWIKFWNBSZ-UHFFFAOYSA-N n-methyl-6-[[3-(2-methylpropyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]methoxy]pyridazine-3-carboxamide Chemical compound N1=NC(C(=O)NC)=CC=C1OCC1=CC=C(CCN(CC(C)C)CC2)C2=C1 ZATFGWIKFWNBSZ-UHFFFAOYSA-N 0.000 claims 1
- PBXDMLVXWMFFLZ-UHFFFAOYSA-N n-methyl-6-[[3-(2-methylpropyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]methoxy]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1OCC1=CC=C(CCN(CC(C)C)CC2)C2=C1 PBXDMLVXWMFFLZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0418267.1A GB0418267D0 (en) | 2004-08-16 | 2004-08-16 | Novel compounds |
| PCT/EP2005/008841 WO2006018260A1 (en) | 2004-08-16 | 2005-08-12 | Tetrahydrobenzazepines as antagonists and/or reverse agonists of the histamine h 3 receptor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008509955A JP2008509955A (ja) | 2008-04-03 |
| JP2008509955A5 true JP2008509955A5 (enExample) | 2008-10-02 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2007526371A Pending JP2008509955A (ja) | 2004-08-16 | 2005-08-12 | ヒスタミンｈ３受容体のアンタゴニストおよび／または逆アゴニストとしてのテトラヒドロベンズアゼピン |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20070208005A1 (enExample) |
| EP (1) | EP1778643A1 (enExample) |
| JP (1) | JP2008509955A (enExample) |
| AR (1) | AR050698A1 (enExample) |
| GB (1) | GB0418267D0 (enExample) |
| PE (1) | PE20060625A1 (enExample) |
| TW (1) | TW200621716A (enExample) |
| WO (1) | WO2006018260A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE441417T1 (de) | 2002-12-20 | 2009-09-15 | Glaxo Group Ltd | Benzoädüazepinderivate für die behandlung von neurologischen krankheiten |
| GB0513886D0 (en) | 2005-07-06 | 2005-08-10 | Glaxo Group Ltd | Novel compounds |
| JP2009531314A (ja) | 2006-03-10 | 2009-09-03 | ニューロジェン・コーポレーション | ピペラジニルオキソアルキルテトラヒドロイソキノリン類および関連類似物 |
| US20070293475A1 (en) * | 2006-06-20 | 2007-12-20 | Alcon Manufacturing Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
| US9108948B2 (en) * | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| CA2655604C (en) * | 2006-06-23 | 2016-08-09 | Abbott Laboratories | Cyclopropyl amine derivatives |
| CL2008000597A1 (es) * | 2007-03-01 | 2008-09-05 | Glaxo Group Ltd | Forma de dosificacion que comprende 6-(3-ciclobutil-2,3,4,5-tetrahidro-1h-benzo[d]azepin-7-il oxi)-n-metil nicotinamida, un estabilizante y un excipiente; procedimiento de preparacion; y su uso para tratar enfermedades neurologicas. |
| CL2008000596A1 (es) * | 2007-03-01 | 2008-09-05 | Glaxo Group Ltd | Forma de dosificacion que comprende 1-(6-[(3-ciclobutil-2,3,4,5-tetrahidro-1h-3-benzazepin-7-il)oxi]-3-piridinil)-2-pirrolidinona, un estabilizador, un excipiente; procedimiento de preparacion; y su uso para tratar enfermedades neurologicas. |
| US20100197752A1 (en) * | 2007-06-11 | 2010-08-05 | Arthur Kammeijer | Urocanic acid derivatives useful for the treatment of immune-related and inflammatory diseases |
| ES2663517T3 (es) * | 2007-08-27 | 2018-04-13 | Dart Neuroscience (Cayman) Ltd | Compuestos terapéuticos de isoxazol |
| MX2011000460A (es) * | 2008-07-18 | 2011-03-15 | Takeda Pharmaceutical | Derivados de benzazepina y su uso como antagonistas de histamina h3. |
| US9186353B2 (en) * | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| ES2467701T3 (es) * | 2009-05-05 | 2014-06-12 | F. Hoffmann-La Roche Ag | Derivados de isoxazol-piridazina |
| MX2012003394A (es) * | 2009-09-21 | 2012-08-15 | Univ Vanderbilt | Analogos de la nicotinamida de o-bencilo como moduladores alostéricos positivos del mglur5. |
| WO2011083315A1 (en) | 2010-01-08 | 2011-07-14 | Takeda Pharmaceutical Company Limited | Compounds and their use |
| WO2011083316A1 (en) | 2010-01-08 | 2011-07-14 | Takeda Pharmaceutical Company Limited | Benzazepine derivatives for the treatment of central nervous system disorders |
| WO2011083314A1 (en) | 2010-01-08 | 2011-07-14 | Takeda Pharmaceutical Company Limited | Benzazepine derivatives for the treatment of central nervous system disorders |
| WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| EP2647377A1 (en) | 2012-04-06 | 2013-10-09 | Sanofi | Use of an h3 receptor antagonist for the treatment of alzheimer's disease |
| CN104016919A (zh) * | 2014-06-18 | 2014-09-03 | 安徽省逸欣铭医药科技有限公司 | 一种绿卡色林类似物及其制备方法和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003256793A1 (en) * | 2002-08-20 | 2004-03-11 | Eli Lilly And Company | Substituted azepines as histamine h3 receptor antagonists, preparation and therapeutic uses |
| ATE441417T1 (de) * | 2002-12-20 | 2009-09-15 | Glaxo Group Ltd | Benzoädüazepinderivate für die behandlung von neurologischen krankheiten |
| US20080009478A1 (en) * | 2003-10-22 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Benzazepine Derivatives and Methods of Prophylaxis or Treatment of 5Ht2c Receptor Associated Diseases |
| GB0329214D0 (en) * | 2003-12-17 | 2004-01-21 | Glaxo Group Ltd | Novel compounds |
| ES2375963T3 (es) * | 2003-12-18 | 2012-03-07 | Abbott Gmbh & Co. Kg | Tetrahidrobenzacepinas y su uso en la modulación del receptor d3 de la dopamina. |
| US20050137186A1 (en) * | 2003-12-18 | 2005-06-23 | Abbott Gmbh & Co. Kg. | Tetrahydrobenzazepines and their use |
| GB0405628D0 (en) * | 2004-03-12 | 2004-04-21 | Glaxo Group Ltd | Novel compounds |
-
2004
- 2004-08-16 GB GBGB0418267.1A patent/GB0418267D0/en not_active Ceased
-
2005
- 2005-08-12 EP EP05771678A patent/EP1778643A1/en not_active Withdrawn
- 2005-08-12 WO PCT/EP2005/008841 patent/WO2006018260A1/en not_active Ceased
- 2005-08-12 JP JP2007526371A patent/JP2008509955A/ja active Pending
- 2005-08-12 PE PE2005000939A patent/PE20060625A1/es not_active Application Discontinuation
- 2005-08-12 US US11/573,732 patent/US20070208005A1/en not_active Abandoned
- 2005-08-15 TW TW094127666A patent/TW200621716A/zh unknown
- 2005-08-16 AR ARP050103435A patent/AR050698A1/es unknown
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