JP2007514690A5 - - Google Patents
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- JP2007514690A5 JP2007514690A5 JP2006544347A JP2006544347A JP2007514690A5 JP 2007514690 A5 JP2007514690 A5 JP 2007514690A5 JP 2006544347 A JP2006544347 A JP 2006544347A JP 2006544347 A JP2006544347 A JP 2006544347A JP 2007514690 A5 JP2007514690 A5 JP 2007514690A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- benzazepin
- cyclobutyl
- carboxamide
- trifluoroacetate
- 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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- DICATRKPPLGIDM-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-2,5-dimethylpyrazole-3-carboxamide Chemical compound CN1N=C(C)C=C1C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 DICATRKPPLGIDM-UHFFFAOYSA-N 0.000 claims description 2
- -1 3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl Chemical group 0.000 claims 49
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- JYULQMHZZYFFGG-LBEJWNQZSA-N (e)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-(2-fluorophenyl)prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC=CC=C1\C=C\C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 JYULQMHZZYFFGG-LBEJWNQZSA-N 0.000 claims 1
- MIBXRGGKASRKQF-HCUGZAAXSA-N (e)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-(3-fluorophenyl)prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC=CC(\C=C\C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)=C1 MIBXRGGKASRKQF-HCUGZAAXSA-N 0.000 claims 1
- ZBRKGBAGYOZTNZ-ICSBZGNSSA-N (e)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-(4-fluorophenyl)prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(F)=CC=C1\C=C\C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 ZBRKGBAGYOZTNZ-ICSBZGNSSA-N 0.000 claims 1
- URFWVHJWWFVSHM-NBYYMMLRSA-N (e)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-phenylprop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=CC=CC=1/C=C/C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 URFWVHJWWFVSHM-NBYYMMLRSA-N 0.000 claims 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- DGDNDYCGMPBCOA-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-3-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)urea Chemical compound C=1C=C2OCOC2=CC=1NC(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 DGDNDYCGMPBCOA-UHFFFAOYSA-N 0.000 claims 1
- RFKGZEWWBUWQGN-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-propylpyrazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCCC1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NN1C1=CC=CC=C1Cl RFKGZEWWBUWQGN-UHFFFAOYSA-N 0.000 claims 1
- VPYLDHNXVDOIKI-UHFFFAOYSA-N 1-(3-cyanophenyl)-3-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)urea Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1NC(=O)NC1=CC=CC(C#N)=C1 VPYLDHNXVDOIKI-UHFFFAOYSA-N 0.000 claims 1
- FKYUSGNXIIZVKV-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-(2,2-difluoro-1,3-benzodioxol-4-yl)urea Chemical compound C=12OC(F)(F)OC2=CC=CC=1NC(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 FKYUSGNXIIZVKV-UHFFFAOYSA-N 0.000 claims 1
- STDLBFWCOOZDIM-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-(2-ethoxyphenyl)urea Chemical compound CCOC1=CC=CC=C1NC(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 STDLBFWCOOZDIM-UHFFFAOYSA-N 0.000 claims 1
- LWDYURWFXLNVLL-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-(2-methoxy-6-methylphenyl)urea Chemical compound COC1=CC=CC(C)=C1NC(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 LWDYURWFXLNVLL-UHFFFAOYSA-N 0.000 claims 1
- KDCIXYJXPSWMBD-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 KDCIXYJXPSWMBD-UHFFFAOYSA-N 0.000 claims 1
- VPBFUPSNSMZMIQ-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound FC(F)(F)OC1=CC=CC=C1NC(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 VPBFUPSNSMZMIQ-UHFFFAOYSA-N 0.000 claims 1
- USZVUIOETJIEAV-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-cyclohexylurea Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1NC(=O)NC1CCCCC1 USZVUIOETJIEAV-UHFFFAOYSA-N 0.000 claims 1
- RXNRXQUBWIAMPJ-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-phenylurea Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1NC(=O)NC1=CC=CC=C1 RXNRXQUBWIAMPJ-UHFFFAOYSA-N 0.000 claims 1
- IYHIWLVGKHSYPK-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-propan-2-ylurea Chemical compound C1CC2=CC(NC(=O)NC(C)C)=CC=C2CCN1C1CCC1 IYHIWLVGKHSYPK-UHFFFAOYSA-N 0.000 claims 1
- QFPVXPAZLIAATO-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-pyridin-3-ylurea Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1NC(=O)NC1=CC=CN=C1 QFPVXPAZLIAATO-UHFFFAOYSA-N 0.000 claims 1
- ZLWVFFBNWOATNC-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-pyridin-4-ylurea Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1NC(=O)NC1=CC=NC=C1 ZLWVFFBNWOATNC-UHFFFAOYSA-N 0.000 claims 1
- AZPFVOKXSPAMAA-UHFFFAOYSA-N 1-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-quinolin-8-ylurea Chemical compound C=1C=CC2=CC=CN=C2C=1NC(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 AZPFVOKXSPAMAA-UHFFFAOYSA-N 0.000 claims 1
- WUTLAJPNPSIHPD-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-(trifluoromethyl)pyrazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NN1C1=CC=C(Cl)C=C1 WUTLAJPNPSIHPD-UHFFFAOYSA-N 0.000 claims 1
- RGGZFWARTUHDEF-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-methylpyrazole-4-carboxamide;hydrochloride Chemical compound Cl.CC1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NN1C1=CC=C(Cl)C=C1 RGGZFWARTUHDEF-UHFFFAOYSA-N 0.000 claims 1
- NVQNFXJGZQOSTF-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-propylpyrazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCCC1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NN1C1=CC=C(Cl)C=C1 NVQNFXJGZQOSTF-UHFFFAOYSA-N 0.000 claims 1
- BMJWMQQFNQZHJP-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-methylurea Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 BMJWMQQFNQZHJP-UHFFFAOYSA-N 0.000 claims 1
- NQORUGBDIZVBGM-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)urea Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1NC(=O)NC1=CC=C(C#N)C=C1 NQORUGBDIZVBGM-UHFFFAOYSA-N 0.000 claims 1
- IFOKWLZZJNLSJZ-UHFFFAOYSA-N 1-(4-cyanophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-3-(trifluoromethyl)pyrazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C1=NN(C=2C=CC(=CC=2)C#N)C=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 IFOKWLZZJNLSJZ-UHFFFAOYSA-N 0.000 claims 1
- CRHRDUUJYLOPLE-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 CRHRDUUJYLOPLE-UHFFFAOYSA-N 0.000 claims 1
- YRFKTJSECPRNBA-UHFFFAOYSA-N 1-[6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]pyridin-3-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C(C=N1)=CC=C1NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 YRFKTJSECPRNBA-UHFFFAOYSA-N 0.000 claims 1
- VVEZSYWEXMIOOF-UHFFFAOYSA-N 2-(2,1,3-benzoxadiazol-5-yl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1,3-thiazole-4-carboxamide Chemical compound C=1SC(C2=CC3=NON=C3C=C2)=NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 VVEZSYWEXMIOOF-UHFFFAOYSA-N 0.000 claims 1
- GKLRXLZFSJKGNH-UHFFFAOYSA-N 2-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-n-methylpyrazine-2,5-dicarboxamide Chemical compound C1=NC(C(=O)NC)=CN=C1C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 GKLRXLZFSJKGNH-UHFFFAOYSA-N 0.000 claims 1
- PFZUBXPRZHWOMA-UHFFFAOYSA-N 4-(3-cyanopyrazin-2-yl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)piperazine-1-carboxamide Chemical compound C1CN(C=2C(=NC=CN=2)C#N)CCN1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 PFZUBXPRZHWOMA-UHFFFAOYSA-N 0.000 claims 1
- VQQRYDSEKBFWCC-UHFFFAOYSA-N 4-(4-cyanophenoxy)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)piperidine-1-carboxamide Chemical compound C1CC(OC=2C=CC(=CC=2)C#N)CCN1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 VQQRYDSEKBFWCC-UHFFFAOYSA-N 0.000 claims 1
- RWGWUZGQSOOZQX-UHFFFAOYSA-N 4-(4-cyanophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)piperazine-1-carboxamide Chemical compound C1CN(C=2C=CC(=CC=2)C#N)CCN1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 RWGWUZGQSOOZQX-UHFFFAOYSA-N 0.000 claims 1
- QUHXUHKYDJAMEB-UHFFFAOYSA-N 4-(4-cyanophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)piperidine-1-carboxamide Chemical compound C1CC(C=2C=CC(=CC=2)C#N)CCN1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 QUHXUHKYDJAMEB-UHFFFAOYSA-N 0.000 claims 1
- NVNOFQASRHGVIL-UHFFFAOYSA-N 4-cyano-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)benzamide Chemical compound C=1C=C(C#N)C=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 NVNOFQASRHGVIL-UHFFFAOYSA-N 0.000 claims 1
- MBDPCPUMIUZFHC-UHFFFAOYSA-N 5-(3-cyanophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyrazine-2-carboxamide Chemical compound C=1N=C(C=2C=C(C=CC=2)C#N)C=NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 MBDPCPUMIUZFHC-UHFFFAOYSA-N 0.000 claims 1
- FDIJNMJRMOXJQS-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyrazine-2-carboxamide Chemical compound C=1N=C(C=2C=CC(=CC=2)C#N)C=NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 FDIJNMJRMOXJQS-UHFFFAOYSA-N 0.000 claims 1
- RIMBXGOZTXQFCZ-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridine-2-carboxamide Chemical compound C=1C=C(C=2C=CC(=CC=2)C#N)C=NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 RIMBXGOZTXQFCZ-UHFFFAOYSA-N 0.000 claims 1
- BCTVMHNYVZZVSI-UHFFFAOYSA-N 5-(6-cyanopyridin-3-yl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridine-2-carboxamide Chemical compound C=1C=C(C=2C=NC(=CC=2)C#N)C=NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 BCTVMHNYVZZVSI-UHFFFAOYSA-N 0.000 claims 1
- PZIVOFLYUOOSSN-UHFFFAOYSA-N 5-bromo-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridine-3-carboxamide Chemical compound BrC1=CN=CC(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)=C1 PZIVOFLYUOOSSN-UHFFFAOYSA-N 0.000 claims 1
- VXYDEWMYZRYIKP-UHFFFAOYSA-N 5-cyano-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=C(C#N)C=C2CN1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 VXYDEWMYZRYIKP-UHFFFAOYSA-N 0.000 claims 1
- SDFUNVKPPJJATR-UHFFFAOYSA-N 5-cyano-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-2,3-dihydroindole-1-carboxamide Chemical compound C1CC2=CC(C#N)=CC=C2N1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 SDFUNVKPPJJATR-UHFFFAOYSA-N 0.000 claims 1
- OWPVCBZWPYTRTQ-UHFFFAOYSA-N 5-methyl-n-[3-(2-methylcyclopentyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]-2-phenyltriazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1CCCC1N1CCC2=CC(NC(=O)C=3C(=NN(N=3)C=3C=CC=CC=3)C)=CC=C2CC1 OWPVCBZWPYTRTQ-UHFFFAOYSA-N 0.000 claims 1
- FKAASKLHTZFQMA-UHFFFAOYSA-N 5-methyl-n-[3-(3-methylcyclopentyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]-2-phenyltriazole-4-carboxamide;hydrochloride Chemical compound Cl.C1C(C)CCC1N1CCC2=CC(NC(=O)C=3C(=NN(N=3)C=3C=CC=CC=3)C)=CC=C2CC1 FKAASKLHTZFQMA-UHFFFAOYSA-N 0.000 claims 1
- NDMFVVVXQRYLTG-UHFFFAOYSA-N 5-tert-butyl-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-2-methylpyrazole-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN1N=C(C(C)(C)C)C=C1C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 NDMFVVVXQRYLTG-UHFFFAOYSA-N 0.000 claims 1
- OXYIAMPZTWWBJJ-UHFFFAOYSA-N 6-(3-cyanophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridine-3-carboxamide Chemical compound C=1C=C(C=2C=C(C=CC=2)C#N)N=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 OXYIAMPZTWWBJJ-UHFFFAOYSA-N 0.000 claims 1
- SRFREXFOLLXNSB-UHFFFAOYSA-N 6-(4-cyanophenyl)-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridine-3-carboxamide Chemical compound C=1C=C(C=2C=CC(=CC=2)C#N)N=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 SRFREXFOLLXNSB-UHFFFAOYSA-N 0.000 claims 1
- MFDJDLRKZZARKQ-UHFFFAOYSA-N 6-[(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 MFDJDLRKZZARKQ-UHFFFAOYSA-N 0.000 claims 1
- QFRYSWFHAXSCHN-UHFFFAOYSA-N 6-cyano-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridine-3-carboxamide Chemical compound C=1C=C(C#N)N=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 QFRYSWFHAXSCHN-UHFFFAOYSA-N 0.000 claims 1
- AMZYYZFIOSLXHC-UHFFFAOYSA-N 7-cyano-n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-2,3-dihydro-1,4-benzoxazine-4-carboxamide Chemical compound C1COC2=CC(C#N)=CC=C2N1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 AMZYYZFIOSLXHC-UHFFFAOYSA-N 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- ISNVSMMQFZHALP-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1,2,3-benzothiadiazole-5-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2SN=NC2=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 ISNVSMMQFZHALP-UHFFFAOYSA-N 0.000 claims 1
- LENWSLKJAYMAMR-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CC2=CC=CC=C2CCN1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 LENWSLKJAYMAMR-UHFFFAOYSA-N 0.000 claims 1
- HKPJOESQIRCIQC-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1,2,5-oxadiazole-3-carboxamide Chemical compound C1=NON=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 HKPJOESQIRCIQC-UHFFFAOYSA-N 0.000 claims 1
- SZLCURRAMPGOAI-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=CON=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 SZLCURRAMPGOAI-UHFFFAOYSA-N 0.000 claims 1
- ZJTIAJOZBAWDPK-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1,3,5-trimethylpyrazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=NN(C)C(C)=C1C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 ZJTIAJOZBAWDPK-UHFFFAOYSA-N 0.000 claims 1
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- SYZYATBGWVVOFZ-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-benzothiophene-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1SC2=CC=CC=C2C=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 SYZYATBGWVVOFZ-UHFFFAOYSA-N 0.000 claims 1
- MLSCXLGFONLRCQ-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-ethyl-5-methylpyrazole-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)N(CC)N=C1C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 MLSCXLGFONLRCQ-UHFFFAOYSA-N 0.000 claims 1
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- AIJYSVWXGGTEHO-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-methylimidazole-4-carboxamide Chemical compound CN1C=NC(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)=C1 AIJYSVWXGGTEHO-UHFFFAOYSA-N 0.000 claims 1
- KIXLKEFSSVEKHU-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-methylindole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=CC=CC=C2N(C)C=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 KIXLKEFSSVEKHU-UHFFFAOYSA-N 0.000 claims 1
- KFXAAOYBIPDBNF-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-methylpyrazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NN(C)C=C1C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 KFXAAOYBIPDBNF-UHFFFAOYSA-N 0.000 claims 1
- PWNZSMRHWCAIGN-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-methyltriazole-4-carboxamide Chemical compound N1=NN(C)C=C1C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 PWNZSMRHWCAIGN-UHFFFAOYSA-N 0.000 claims 1
- HUNTYADHKJQMSF-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-phenyl-5-(trifluoromethyl)pyrazole-4-carboxamide;hydrochloride Chemical compound Cl.FC(F)(F)C1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NN1C1=CC=CC=C1 HUNTYADHKJQMSF-UHFFFAOYSA-N 0.000 claims 1
- BISDIUIOBHYTIJ-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-phenyl-5-propylpyrazole-4-carboxamide;hydrochloride Chemical compound Cl.CCCC1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)C=NN1C1=CC=CC=C1 BISDIUIOBHYTIJ-UHFFFAOYSA-N 0.000 claims 1
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- HUVTXHHXVLHDNY-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1-propan-2-ylbenzotriazole-5-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2N(C(C)C)N=NC2=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 HUVTXHHXVLHDNY-UHFFFAOYSA-N 0.000 claims 1
- CSEDTPVFMSARFV-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1h-benzimidazole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1C2=CC=CC=C2NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 CSEDTPVFMSARFV-UHFFFAOYSA-N 0.000 claims 1
- ZQUPZIFFYPRKAW-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1h-indazole-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1NC2=CC=CC=C2C=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 ZQUPZIFFYPRKAW-UHFFFAOYSA-N 0.000 claims 1
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- DZCLCGZLROROHH-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-1h-indole-6-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2C=CNC2=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 DZCLCGZLROROHH-UHFFFAOYSA-N 0.000 claims 1
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- DDRXDOAFAFTRBV-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-2-methyl-1,6-naphthyridine-3-carboxamide Chemical compound CC1=NC2=CC=NC=C2C=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 DDRXDOAFAFTRBV-UHFFFAOYSA-N 0.000 claims 1
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- APLHZDKFTYZKHF-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-4-(4-fluorophenyl)piperidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1C1CCN(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)CC1 APLHZDKFTYZKHF-UHFFFAOYSA-N 0.000 claims 1
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- PLROOQQHPBHDHH-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-(3,4-dimethoxyphenyl)-2h-triazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(OC)C(OC)=CC=C1C1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)NN=N1 PLROOQQHPBHDHH-UHFFFAOYSA-N 0.000 claims 1
- TVDVKHKAYVSKTM-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-(4-fluorophenoxy)-2h-triazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(F)=CC=C1OC1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)NN=N1 TVDVKHKAYVSKTM-UHFFFAOYSA-N 0.000 claims 1
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- ISPNJWQYQHYLRF-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-imidazol-1-ylpyridine-3-carboxamide Chemical compound C=1N=CC(N2C=NC=C2)=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 ISPNJWQYQHYLRF-UHFFFAOYSA-N 0.000 claims 1
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- YOHVUQNSQSXXSM-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-methyl-1-phenylpyrazole-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)=NN1C1=CC=CC=C1 YOHVUQNSQSXXSM-UHFFFAOYSA-N 0.000 claims 1
- IWEVOTHJQZBACY-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-methyl-1-phenyltriazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCC2)N=NN1C1=CC=CC=C1 IWEVOTHJQZBACY-UHFFFAOYSA-N 0.000 claims 1
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- IIERNBFMJXVLJN-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-methyl-2-phenylpyrazole-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=CC=CC=1N1N=C(C)C=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 IIERNBFMJXVLJN-UHFFFAOYSA-N 0.000 claims 1
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- XIRLAVZGBZMOIP-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-pyridin-3-ylpyridine-3-carboxamide Chemical compound C=1N=CC(C=2C=NC=CC=2)=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 XIRLAVZGBZMOIP-UHFFFAOYSA-N 0.000 claims 1
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- IGUAILUEBOXOOB-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-6-methylpyridine-3-carboxamide Chemical compound C1=NC(C)=CC=C1C(=O)NC1=CC=C(CCN(CC2)C3CCC3)C2=C1 IGUAILUEBOXOOB-UHFFFAOYSA-N 0.000 claims 1
- PHGGVUBJFJZPME-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-6-morpholin-4-ylpyridine-3-carboxamide Chemical compound C=1C=C(N2CCOCC2)N=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 PHGGVUBJFJZPME-UHFFFAOYSA-N 0.000 claims 1
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- CSECTEIQBRAIHO-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1=CC(=O)NC=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 CSECTEIQBRAIHO-UHFFFAOYSA-N 0.000 claims 1
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- DZJRUHNICJODPY-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-6-pyridin-3-ylpyridine-3-carboxamide Chemical compound C=1C=C(C=2C=NC=CC=2)N=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 DZJRUHNICJODPY-UHFFFAOYSA-N 0.000 claims 1
- OSLOLMURMBCTCI-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-6-pyrimidin-5-ylpyridine-3-carboxamide Chemical compound C=1C=C(C=2C=NC=NC=2)N=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 OSLOLMURMBCTCI-UHFFFAOYSA-N 0.000 claims 1
- YSMOFMUDTYSMJV-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-n,6-dimethylpyridine-3-carboxamide Chemical compound C=1C=C2CCN(C3CCC3)CCC2=CC=1N(C)C(=O)C1=CC=C(C)N=C1 YSMOFMUDTYSMJV-UHFFFAOYSA-N 0.000 claims 1
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- VSORXNMSBMRLOY-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=NN2C=CC=NC2=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 VSORXNMSBMRLOY-UHFFFAOYSA-N 0.000 claims 1
- BDTVQPWVDJVZMU-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridazine-4-carboxamide Chemical compound C=1C=NN=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 BDTVQPWVDJVZMU-UHFFFAOYSA-N 0.000 claims 1
- ASAZYGKVSLJGNH-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 ASAZYGKVSLJGNH-UHFFFAOYSA-N 0.000 claims 1
- PXZKNILRCPTPLU-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 PXZKNILRCPTPLU-UHFFFAOYSA-N 0.000 claims 1
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- JPKQCYCCWQTCKL-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)quinoline-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2C=CC=CC2=NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 JPKQCYCCWQTCKL-UHFFFAOYSA-N 0.000 claims 1
- MXKBPGFTOHYMDU-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)quinoline-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1N=C2C=CC=CC2=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 MXKBPGFTOHYMDU-UHFFFAOYSA-N 0.000 claims 1
- XQZUQUJXYISGLM-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)quinoxaline-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1N=C2C=CC=CC2=NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 XQZUQUJXYISGLM-UHFFFAOYSA-N 0.000 claims 1
- QQSOYFTYGKENBE-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)quinoxaline-5-carboxamide Chemical compound C=1C=CC2=NC=CN=C2C=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 QQSOYFTYGKENBE-UHFFFAOYSA-N 0.000 claims 1
- LBSWMFBLYMPIGY-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 LBSWMFBLYMPIGY-UHFFFAOYSA-N 0.000 claims 1
- JZBWPGJDMVNHDR-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)thiadiazole-4-carboxamide Chemical compound C=1SN=NC=1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 JZBWPGJDMVNHDR-UHFFFAOYSA-N 0.000 claims 1
- UNFCPRGDWIWJBA-UHFFFAOYSA-N n-(3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)thiophene-3-carboxamide Chemical compound C1=CSC=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCC1 UNFCPRGDWIWJBA-UHFFFAOYSA-N 0.000 claims 1
- IHTVBOSJWLCAOJ-UHFFFAOYSA-N n-(3-cyclohexyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-methyl-1-phenylpyrazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=C(C(=O)NC=2C=C3CCN(CCC3=CC=2)C2CCCCC2)C=NN1C1=CC=CC=C1 IHTVBOSJWLCAOJ-UHFFFAOYSA-N 0.000 claims 1
- JKLMCRRNIRBSOQ-UHFFFAOYSA-N n-(3-cyclohexyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-methyl-2-phenyltriazole-4-carboxamide;hydrochloride Chemical compound Cl.CC1=NN(C=2C=CC=CC=2)N=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCCCC1 JKLMCRRNIRBSOQ-UHFFFAOYSA-N 0.000 claims 1
- CXCFNEFYUKETER-UHFFFAOYSA-N n-(3-cyclopentyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)-5-methyl-2-phenyltriazole-4-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=NN(C=2C=CC=CC=2)N=C1C(=O)NC(C=C1CC2)=CC=C1CCN2C1CCCC1 CXCFNEFYUKETER-UHFFFAOYSA-N 0.000 claims 1
- MZXGBYUWONZVFA-UHFFFAOYSA-N n-(trifluoromethyl)pyridine-3-carboxamide Chemical compound FC(F)(F)NC(=O)C1=CC=CN=C1 MZXGBYUWONZVFA-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000001679 citrus red 2 Substances 0.000 description 2
- ZIAPGUFDEJWQHC-UHFFFAOYSA-N 2,5-dimethylpyrazole-3-carbonyl chloride Chemical compound CC=1C=C(C(Cl)=O)N(C)N=1 ZIAPGUFDEJWQHC-UHFFFAOYSA-N 0.000 description 1
- CRSFNXWYTLCSFD-UHFFFAOYSA-N 3-cyclobutyl-1,2,4,5-tetrahydro-3-benzazepin-7-amine Chemical compound C1CC2=CC(N)=CC=C2CCN1C1CCC1 CRSFNXWYTLCSFD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
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| PCT/EP2004/014380 WO2005058837A1 (en) | 2003-12-17 | 2004-12-15 | Benzazepine derivatives as histamine h3 antagonists |
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| GB (1) | GB0329214D0 (enExample) |
| WO (1) | WO2005058837A1 (enExample) |
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| CA2509413C (en) * | 2002-12-20 | 2012-05-01 | Glaxo Group Limited | Benzazepine derivatives for the treatment of neurological disorders |
| PE20060302A1 (es) * | 2004-06-18 | 2006-04-08 | Glaxo Group Ltd | Derivados de benzazepina como antagonistas del receptor h3 |
| GB0418267D0 (en) * | 2004-08-16 | 2004-09-15 | Glaxo Group Ltd | Novel compounds |
| GB0513886D0 (en) | 2005-07-06 | 2005-08-10 | Glaxo Group Ltd | Novel compounds |
| US7795262B2 (en) | 2006-03-10 | 2010-09-14 | Neurogen Corporation | Piperazinyl oxoalkyl tetrahydroisoquinolines and related analogues |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| MX2008016343A (es) | 2006-06-23 | 2009-01-19 | Abbott Lab | Derivados ciclopropil amina como moduladores del receptro de histamina h3. |
| 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. |
| MX2010006457A (es) * | 2007-12-19 | 2010-07-05 | Amgen Inc | Compuestos fusionados de piridina, pirimidina y triazina como inhibidores de ciclo celular. |
| UY31736A (es) * | 2008-03-26 | 2009-11-10 | Takeda Pharmaceutical | Derivados sustituidos de pirazol y su uso |
| CA2719538C (en) * | 2008-04-07 | 2014-03-18 | Amgen Inc. | Gem-disubstituted and spirocyclic amino pyridines/pyrimidines as cell cycle inhibitors |
| CA2725481A1 (en) | 2008-06-18 | 2009-12-23 | Pfizer Limited | Nicotinamide derivatives |
| EP2326625A1 (en) * | 2008-07-18 | 2011-06-01 | Takeda Pharmaceutical Company Limited | Benzazepine derivatives and their use as hstamine h3 antagonists |
| EP2348860B1 (en) | 2008-10-31 | 2015-05-27 | Genentech, Inc. | Pyrazolopyrimidine jak inhibitor compounds and methods |
| US8946231B2 (en) | 2009-03-23 | 2015-02-03 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| UA110324C2 (en) | 2009-07-02 | 2015-12-25 | Genentech Inc | Jak inhibitory compounds based on pyrazolo pyrimidine |
| TW201141485A (en) | 2010-01-08 | 2011-12-01 | Takeda Pharmaceutical | Compounds and their use |
| 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 |
| WO2011118812A1 (ja) * | 2010-03-26 | 2011-09-29 | 国立大学法人北海道大学 | 神経変性疾患治療薬 |
| WO2011156321A1 (en) | 2010-06-07 | 2011-12-15 | Novomedix, Llc | Furanyl compounds and the use thereof |
| MX358682B (es) * | 2010-07-13 | 2018-08-31 | Hoffmann La Roche | Derivados de pirazolo [1,5a]pirimidina y de tieno[3,2b] pirimidina como moduladores de la cinasa asociada al receptor de la interleucina 4 (irak4). |
| US8853390B2 (en) | 2010-09-16 | 2014-10-07 | Abbvie Inc. | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| AU2011329233A1 (en) * | 2010-11-15 | 2013-05-23 | Abbvie Deutschland Gmbh & Co Kg | NAMPT and ROCK inhibitors |
| US9199918B2 (en) | 2011-02-15 | 2015-12-01 | Georgetown University | Small molecule inhibitors of AGBL2 |
| DK2688887T3 (en) | 2011-03-23 | 2015-06-29 | Amgen Inc | DEHYDRATED tricyclic DUALINHIBITORER OF CDK 4/6 AND FLT3 |
| 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 |
| CN105101959B (zh) * | 2012-11-05 | 2018-04-17 | 南特知识产权控股有限责任公司 | 作为刺猬信号传导通路的抑制剂的含有环状磺酰胺的衍生物 |
| HRP20210935T1 (hr) | 2014-05-23 | 2021-08-06 | F. Hoffmann - La Roche Ag | Spojevi 5-kloro-2-difluorometoksifenil pirazolopirimidina koji predstavljaju inhibitore jak |
| CA2966581A1 (en) | 2014-11-06 | 2016-05-12 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders |
| DK3215511T3 (da) * | 2014-11-06 | 2024-05-13 | Bial R&D Invest S A | Substituerede pyrazolo(1,5-a)pyrimidiner og deres anvendelse i behandlingen af medicinske lidelser |
| ES2958391T3 (es) | 2014-11-06 | 2024-02-08 | Bial R&D Invest S A | Imidazo[1,5-a]pirimidinas sustituidas y su uso en el tratamiento de trastornos médicos |
| JP6895439B2 (ja) * | 2015-12-22 | 2021-06-30 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ＩＲＡＫ４調節因子としてのピラゾロ［１，５ａ］ピリミジン誘導体 |
| WO2017176962A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics, Inc. | Pyrrolo[1,2-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| WO2017176960A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics Inc. | Pyrazolo[1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| JP7046827B2 (ja) | 2016-04-06 | 2022-04-04 | リソソーマル・セラピューティクス・インコーポレイテッド | イミダゾ［１，５－ａ］ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 |
| US11345698B2 (en) | 2016-05-05 | 2022-05-31 | Bial—R&D Investments, S.A. | Substituted imidazo[1,2-a]pyridines, substituted imidazo[1,2-a]pyrazines, related compounds, and their use in the treatment of medical disorders |
| BR112018072552A8 (pt) | 2016-05-05 | 2023-03-14 | Lysosomal Therapeutics Inc | Compostos de imidazo [1,2-b]piridazinas e imidazo [1,5-b] piridazinas substituídas, composição farmacêutica que os compreende e seu uso no tratamento de distúrbios médicos |
| WO2018083085A1 (en) | 2016-11-02 | 2018-05-11 | F. Hoffmann-La Roche Ag | PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS |
| TW201902896A (zh) | 2017-05-22 | 2019-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療化合物及組合物及其使用方法 |
| CN117024420A (zh) * | 2017-12-29 | 2023-11-10 | 生物马林药物股份有限公司 | 用于疾病治疗的乙醇酸氧化酶抑制剂 |
| WO2020117877A1 (en) * | 2018-12-04 | 2020-06-11 | Aquinnah Pharmaceuticals, Inc. | Compounds, compositions and methods of use |
| WO2020263960A1 (en) * | 2019-06-28 | 2020-12-30 | Carl Wagner | Compositions comprising a retinoid x receptor (rxr) agonist, a retinoic acid receptor (rar) agonist, or a dual rxr/rar agonist |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4210749A (en) * | 1974-11-12 | 1980-07-01 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H,3 benzazepines |
| AU685054C (en) * | 1992-05-14 | 2003-02-27 | Baylor College Of Medicine | Mutated steroid hormone receptors, methods for their use and molecular switch for gene therapy |
| US5364791A (en) * | 1992-05-14 | 1994-11-15 | Elisabetta Vegeto | Progesterone receptor having C. terminal hormone binding domain truncations |
| DE4429079A1 (de) * | 1994-08-17 | 1996-02-22 | Thomae Gmbh Dr K | Cyclische Harnstoffderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US20030207863A1 (en) * | 2000-08-25 | 2003-11-06 | Hiroaki Fukumoto | Preventives and remedies for central nervous system diseases |
| DE60304695T2 (de) * | 2002-02-13 | 2006-09-21 | Glaxo Group Ltd., Greenford | 7-arylsulfonamido-2,3,4,5-tetrahydro-1h-benzo[d]azepin-derivate mit 5-hat-6-rezeptor affinität zur behandlung von erkrankungen des zentralnervensystems |
| GB0210762D0 (en) * | 2002-05-10 | 2002-06-19 | Glaxo Group Ltd | Compounds |
| CA2509413C (en) * | 2002-12-20 | 2012-05-01 | Glaxo Group Limited | Benzazepine derivatives for the treatment of neurological disorders |
-
2003
- 2003-12-17 GB GBGB0329214.1A patent/GB0329214D0/en not_active Ceased
-
2004
- 2004-12-15 WO PCT/EP2004/014380 patent/WO2005058837A1/en not_active Ceased
- 2004-12-15 EP EP04803989A patent/EP1713778B1/en not_active Expired - Lifetime
- 2004-12-15 AT AT04803989T patent/ATE384050T1/de not_active IP Right Cessation
- 2004-12-15 JP JP2006544347A patent/JP2007514690A/ja active Pending
- 2004-12-15 DE DE602004011401T patent/DE602004011401T2/de not_active Expired - Lifetime
- 2004-12-15 US US10/596,503 patent/US20070060566A1/en not_active Abandoned
- 2004-12-15 ES ES04803989T patent/ES2299896T3/es not_active Expired - Lifetime
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