JP2007516196A5 - - Google Patents
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- Publication number
- JP2007516196A5 JP2007516196A5 JP2006518333A JP2006518333A JP2007516196A5 JP 2007516196 A5 JP2007516196 A5 JP 2007516196A5 JP 2006518333 A JP2006518333 A JP 2006518333A JP 2006518333 A JP2006518333 A JP 2006518333A JP 2007516196 A5 JP2007516196 A5 JP 2007516196A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- phenyl
- hydroxy
- amine
- phenol
- 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.)
- Abandoned
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- -1 2-pyridin-4-yl-ethyl Chemical group 0.000 claims 99
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 6
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- BGNMRHIRLAQXQD-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-[5-[(3-hydroxyphenyl)methylamino]pyridin-3-yl]benzamide Chemical compound OCCNC(=O)C1=CC=CC(C=2C=C(NCC=3C=C(O)C=CC=3)C=NC=2)=C1 BGNMRHIRLAQXQD-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 229910052760 oxygen Chemical group 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 3
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 3
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 3
- 238000003556 assay Methods 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- GDRHTKHOBWKHKZ-UHFFFAOYSA-N 1-[5-[5-(2-pyridin-4-ylethylamino)pyrazin-2-yl]thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC=C1C(N=C1)=CN=C1NCCC1=CC=NC=C1 GDRHTKHOBWKHKZ-UHFFFAOYSA-N 0.000 claims 2
- XUAHHCGDMHAXLG-UHFFFAOYSA-N 2-[1-(5-pyridin-4-ylpyrazin-2-yl)piperidin-2-yl]ethanol Chemical compound OCCC1CCCCN1C1=CN=C(C=2C=CN=CC=2)C=N1 XUAHHCGDMHAXLG-UHFFFAOYSA-N 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])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
- IBMYZDCFIPIDSU-UHFFFAOYSA-N 3-(aminomethyl)-5-[2-(3-hydroxyphenyl)pyridin-3-yl]phenol Chemical compound OC=1C=C(C=CC=1)C1=NC=CC=C1C=1C=C(C=C(CN)C=1)O IBMYZDCFIPIDSU-UHFFFAOYSA-N 0.000 claims 2
- WAOHVGCRZATZQG-UHFFFAOYSA-N 3-(aminomethyl)-5-[2-(4-hydroxyphenyl)pyridin-3-yl]phenol Chemical compound OC1=CC=C(C=C1)C1=NC=CC=C1C=1C=C(C=C(CN)C=1)O WAOHVGCRZATZQG-UHFFFAOYSA-N 0.000 claims 2
- CSZPLUCOLWTMMQ-UHFFFAOYSA-N 3-[5-(1,3-benzodioxol-5-ylmethylamino)pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=C4OCOC4=CC=3)C=NC=2)=C1 CSZPLUCOLWTMMQ-UHFFFAOYSA-N 0.000 claims 2
- OTBKMPNEGDWBTQ-UHFFFAOYSA-N 3-[5-(3-bromoanilino)pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NC=3C=C(Br)C=CC=3)C=NC=2)=C1 OTBKMPNEGDWBTQ-UHFFFAOYSA-N 0.000 claims 2
- HZPCHEKURXWCQZ-UHFFFAOYSA-N 3-[5-(3-hydroxyanilino)pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NC=3C=C(O)C=CC=3)C=NC=2)=C1 HZPCHEKURXWCQZ-UHFFFAOYSA-N 0.000 claims 2
- ZQDQSTDCYCIOOK-UHFFFAOYSA-N 3-[5-(cyclohexylmethylamino)pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC3CCCCC3)C=NC=2)=C1 ZQDQSTDCYCIOOK-UHFFFAOYSA-N 0.000 claims 2
- AVQNDKQSGPZEON-UHFFFAOYSA-N 3-[5-(pyridin-3-ylmethylamino)pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=NC=CC=3)C=NC=2)=C1 AVQNDKQSGPZEON-UHFFFAOYSA-N 0.000 claims 2
- LMVDLAKTHWHLGE-UHFFFAOYSA-N 3-[5-(pyrrolidin-2-ylmethylamino)pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC3NCCC3)C=NC=2)=C1 LMVDLAKTHWHLGE-UHFFFAOYSA-N 0.000 claims 2
- PFKWOOHXYAHVCT-UHFFFAOYSA-N 3-[5-[(3,4-dichlorophenyl)methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=C(Cl)C(Cl)=CC=3)C=NC=2)=C1 PFKWOOHXYAHVCT-UHFFFAOYSA-N 0.000 claims 2
- KJOWBXYKYMKKRH-UHFFFAOYSA-N 3-[5-[(3,4-difluorophenyl)methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=C(F)C(F)=CC=3)C=NC=2)=C1 KJOWBXYKYMKKRH-UHFFFAOYSA-N 0.000 claims 2
- YZWQZMDLAUYIMV-UHFFFAOYSA-N 3-[5-[(3,5-dihydroxyphenyl)methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=C(O)C=C(O)C=3)C=NC=2)=C1 YZWQZMDLAUYIMV-UHFFFAOYSA-N 0.000 claims 2
- VTYIKNNXHBYXQD-UHFFFAOYSA-N 3-[5-[(3-chlorophenyl)methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=C(Cl)C=CC=3)C=NC=2)=C1 VTYIKNNXHBYXQD-UHFFFAOYSA-N 0.000 claims 2
- LIUJMBINNLHQCG-UHFFFAOYSA-N 3-[5-[(3-hydroxy-4-methoxyphenyl)methylamino]pyridin-3-yl]benzamide Chemical compound C1=C(O)C(OC)=CC=C1CNC1=CN=CC(C=2C=C(C=CC=2)C(N)=O)=C1 LIUJMBINNLHQCG-UHFFFAOYSA-N 0.000 claims 2
- ORVGYSWASPQPLL-UHFFFAOYSA-N 3-[5-[(3-hydroxyphenyl)methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=C(O)C=CC=3)C=NC=2)=C1 ORVGYSWASPQPLL-UHFFFAOYSA-N 0.000 claims 2
- SMUZPYKXXBUVCX-UHFFFAOYSA-N 3-[5-[(4-chloro-3-fluorophenyl)methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=C(F)C(Cl)=CC=3)C=NC=2)=C1 SMUZPYKXXBUVCX-UHFFFAOYSA-N 0.000 claims 2
- PUTKFYUFTBSDJG-UHFFFAOYSA-N 3-[5-[(4-chlorophenyl)methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=CC(Cl)=CC=3)C=NC=2)=C1 PUTKFYUFTBSDJG-UHFFFAOYSA-N 0.000 claims 2
- YOQMLNMCASDZKJ-UHFFFAOYSA-N 3-[5-[(4-hydroxyphenyl)methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=CC(O)=CC=3)C=NC=2)=C1 YOQMLNMCASDZKJ-UHFFFAOYSA-N 0.000 claims 2
- SRUCABUHBPRCRI-UHFFFAOYSA-N 3-[5-[(4-methoxyphenyl)methylamino]pyridin-3-yl]benzamide Chemical compound C1=CC(OC)=CC=C1CNC1=CN=CC(C=2C=C(C=CC=2)C(N)=O)=C1 SRUCABUHBPRCRI-UHFFFAOYSA-N 0.000 claims 2
- YPHLQUGESJJZTA-UHFFFAOYSA-N 3-[5-[[3-(trifluoromethoxy)phenyl]methylamino]pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC=3C=C(OC(F)(F)F)C=CC=3)C=NC=2)=C1 YPHLQUGESJJZTA-UHFFFAOYSA-N 0.000 claims 2
- WEGSPPOZMNGVGO-UHFFFAOYSA-N 3-[[(5-isoquinolin-4-ylpyridin-3-yl)amino]methyl]phenol Chemical compound OC1=CC=CC(CNC=2C=C(C=NC=2)C=2C3=CC=CC=C3C=NC=2)=C1 WEGSPPOZMNGVGO-UHFFFAOYSA-N 0.000 claims 2
- SYWGFARUHUXJFT-UHFFFAOYSA-N 3-[[(5-phenylpyridin-3-yl)amino]methyl]phenol Chemical compound OC1=CC=CC(CNC=2C=C(C=NC=2)C=2C=CC=CC=2)=C1 SYWGFARUHUXJFT-UHFFFAOYSA-N 0.000 claims 2
- SIFJVSMPFNGVOV-UHFFFAOYSA-N 3-[[(5-quinolin-5-ylpyridin-3-yl)amino]methyl]phenol Chemical compound OC1=CC=CC(CNC=2C=C(C=NC=2)C=2C3=CC=CN=C3C=CC=2)=C1 SIFJVSMPFNGVOV-UHFFFAOYSA-N 0.000 claims 2
- MCCQBUHCJJZWDX-UHFFFAOYSA-N 3-[[5-(4-hydroxyphenyl)pyridin-3-yl]amino]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NC=2C=C(O)C=CC=2)=C1 MCCQBUHCJJZWDX-UHFFFAOYSA-N 0.000 claims 2
- APDSRBYUZZKDBQ-UHFFFAOYSA-N 3-[[[5-(1,3-benzodioxol-5-yl)pyridin-3-yl]amino]methyl]phenol Chemical compound OC1=CC=CC(CNC=2C=C(C=NC=2)C=2C=C3OCOC3=CC=2)=C1 APDSRBYUZZKDBQ-UHFFFAOYSA-N 0.000 claims 2
- YROXZKBGTDIQBP-UHFFFAOYSA-N 3-[[[5-(1h-indol-5-yl)pyridin-3-yl]amino]methyl]phenol Chemical compound OC1=CC=CC(CNC=2C=C(C=NC=2)C=2C=C3C=CNC3=CC=2)=C1 YROXZKBGTDIQBP-UHFFFAOYSA-N 0.000 claims 2
- MVTMKFRXWQDELP-UHFFFAOYSA-N 3-[[[5-(1h-pyrazol-5-yl)pyridin-3-yl]amino]methyl]phenol Chemical compound OC1=CC=CC(CNC=2C=C(C=NC=2)C2=NNC=C2)=C1 MVTMKFRXWQDELP-UHFFFAOYSA-N 0.000 claims 2
- JPZJTMJKAJYQKI-UHFFFAOYSA-N 3-[[[5-(3-aminophenyl)pyridin-3-yl]amino]methyl]phenol Chemical compound NC1=CC=CC(C=2C=C(NCC=3C=C(O)C=CC=3)C=NC=2)=C1 JPZJTMJKAJYQKI-UHFFFAOYSA-N 0.000 claims 2
- IOQPZKZRBPIFOA-UHFFFAOYSA-N 3-[[[5-(3-chloropyridin-4-yl)pyridin-3-yl]amino]methyl]phenol Chemical compound OC1=CC=CC(CNC=2C=C(C=NC=2)C=2C(=CN=CC=2)Cl)=C1 IOQPZKZRBPIFOA-UHFFFAOYSA-N 0.000 claims 2
- RQYNWWQMPILBBF-UHFFFAOYSA-N 3-[[[5-(4-aminophenyl)pyridin-3-yl]amino]methyl]phenol Chemical compound C1=CC(N)=CC=C1C1=CN=CC(NCC=2C=C(O)C=CC=2)=C1 RQYNWWQMPILBBF-UHFFFAOYSA-N 0.000 claims 2
- GCTDVJBFLNISQQ-UHFFFAOYSA-N 3-[[[5-(4-hydroxyphenyl)pyridin-3-yl]-methylamino]methyl]phenol Chemical compound C=1N=CC(C=2C=CC(O)=CC=2)=CC=1N(C)CC1=CC=CC(O)=C1 GCTDVJBFLNISQQ-UHFFFAOYSA-N 0.000 claims 2
- YJLQTOWWOQQQSY-UHFFFAOYSA-N 3-[[[5-(5-methoxypyridin-3-yl)pyridin-3-yl]amino]methyl]phenol Chemical compound COC1=CN=CC(C=2C=C(NCC=3C=C(O)C=CC=3)C=NC=2)=C1 YJLQTOWWOQQQSY-UHFFFAOYSA-N 0.000 claims 2
- OXEMBISODIOWBF-UHFFFAOYSA-N 3-[[[5-[4-(hydroxymethyl)phenyl]pyridin-3-yl]amino]methyl]phenol Chemical compound C1=CC(CO)=CC=C1C1=CN=CC(NCC=2C=C(O)C=CC=2)=C1 OXEMBISODIOWBF-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
- SYOCLMLCCQJNRA-UHFFFAOYSA-N 3-methyl-2-[(5-pyridin-4-ylpyrazin-2-yl)amino]butan-1-ol Chemical compound C1=NC(NC(CO)C(C)C)=CN=C1C1=CC=NC=C1 SYOCLMLCCQJNRA-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- KLTUVMBCGIOERW-UHFFFAOYSA-N 4-[5-(1-phenylethylamino)pyrazin-2-yl]phenol Chemical compound C=1C=CC=CC=1C(C)NC(N=C1)=CN=C1C1=CC=C(O)C=C1 KLTUVMBCGIOERW-UHFFFAOYSA-N 0.000 claims 2
- FUUVDOSXANTAOW-UHFFFAOYSA-N 4-[5-(benzylamino)pyrazin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C(N=C1)=CN=C1NCC1=CC=CC=C1 FUUVDOSXANTAOW-UHFFFAOYSA-N 0.000 claims 2
- GRGKMYDWHXPKHW-UHFFFAOYSA-N 4-[5-(cyclohexylmethylamino)pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC2CCCCC2)=C1 GRGKMYDWHXPKHW-UHFFFAOYSA-N 0.000 claims 2
- GMLXCUOXIMWHAN-UHFFFAOYSA-N 4-[5-(furan-3-ylmethylamino)pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC2=COC=C2)=C1 GMLXCUOXIMWHAN-UHFFFAOYSA-N 0.000 claims 2
- IHPGDNDKTUQKJU-UHFFFAOYSA-N 4-[5-(naphthalen-2-ylmethylamino)pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC=2C=C3C=CC=CC3=CC=2)=C1 IHPGDNDKTUQKJU-UHFFFAOYSA-N 0.000 claims 2
- VJHYFSOXBAEPQA-UHFFFAOYSA-N 4-[5-(pyrrolidin-2-ylmethylamino)pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC2NCCC2)=C1 VJHYFSOXBAEPQA-UHFFFAOYSA-N 0.000 claims 2
- HZZGASNLZCIERF-UHFFFAOYSA-N 4-[5-[(3,4-dichlorophenyl)methylamino]pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC=2C=C(Cl)C(Cl)=CC=2)=C1 HZZGASNLZCIERF-UHFFFAOYSA-N 0.000 claims 2
- AUIZLHIMJRFGPG-UHFFFAOYSA-N 4-[5-[(3,4-difluorophenyl)methylamino]pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC=2C=C(F)C(F)=CC=2)=C1 AUIZLHIMJRFGPG-UHFFFAOYSA-N 0.000 claims 2
- LOXATRTYBQXOEU-UHFFFAOYSA-N 4-[5-[(3,4-dimethoxyphenyl)methylamino]pyridin-3-yl]phenol Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=CN=CC(C=2C=CC(O)=CC=2)=C1 LOXATRTYBQXOEU-UHFFFAOYSA-N 0.000 claims 2
- SMNQTAFIMSSOTC-UHFFFAOYSA-N 4-[5-[(3-chlorophenyl)methylamino]pyrazin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C(N=C1)=CN=C1NCC1=CC=CC(Cl)=C1 SMNQTAFIMSSOTC-UHFFFAOYSA-N 0.000 claims 2
- VGYNBXVIVHCANW-UHFFFAOYSA-N 4-[5-[(3-chlorophenyl)methylamino]pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC=2C=C(Cl)C=CC=2)=C1 VGYNBXVIVHCANW-UHFFFAOYSA-N 0.000 claims 2
- FEBXJMUNCCEHKS-UHFFFAOYSA-N 4-[5-[(3-hydroxyphenyl)methylamino]pyridin-3-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CN=CC(NCC=2C=C(O)C=CC=2)=C1 FEBXJMUNCCEHKS-UHFFFAOYSA-N 0.000 claims 2
- WCNFWGYWAMKIHV-UHFFFAOYSA-N 4-[5-[(4-chlorophenyl)methylamino]pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC=2C=CC(Cl)=CC=2)=C1 WCNFWGYWAMKIHV-UHFFFAOYSA-N 0.000 claims 2
- JYAQILCUGMNWBH-UHFFFAOYSA-N 4-[5-[(4-methoxyphenyl)methylamino]pyridin-3-yl]phenol Chemical compound C1=CC(OC)=CC=C1CNC1=CN=CC(C=2C=CC(O)=CC=2)=C1 JYAQILCUGMNWBH-UHFFFAOYSA-N 0.000 claims 2
- PLWWBNHOUOPASK-UHFFFAOYSA-N 4-[5-[[3-(trifluoromethoxy)phenyl]methylamino]pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC=2C=C(OC(F)(F)F)C=CC=2)=C1 PLWWBNHOUOPASK-UHFFFAOYSA-N 0.000 claims 2
- QKMYRJZEKJOPIH-UHFFFAOYSA-N 4-[[(5-pyridin-4-ylpyrazin-2-yl)amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=CN=C(C=2C=CN=CC=2)C=N1 QKMYRJZEKJOPIH-UHFFFAOYSA-N 0.000 claims 2
- RSPCFZKXHVQLSC-UHFFFAOYSA-N 4-amino-n-[4-[[5-(3-chloropyridin-4-yl)pyrazin-2-yl]amino]phenyl]benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC(C=C1)=CC=C1NC1=CN=C(C=2C(=CN=CC=2)Cl)C=N1 RSPCFZKXHVQLSC-UHFFFAOYSA-N 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- DRELVWFAVSDRGO-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound C=1N=C(C=2C=C3OCOC3=CC=2)C=NC=1NCCC1=CC=NC=C1 DRELVWFAVSDRGO-UHFFFAOYSA-N 0.000 claims 2
- BCEGVIBFXCFBOA-UHFFFAOYSA-N 5-(1-benzofuran-2-yl)-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound C=1N=C(C=2OC3=CC=CC=C3C=2)C=NC=1NCCC1=CC=NC=C1 BCEGVIBFXCFBOA-UHFFFAOYSA-N 0.000 claims 2
- LZHSSLFNBGDQAE-UHFFFAOYSA-N 5-(1-benzothiophen-2-yl)-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound C=1N=C(C=2SC3=CC=CC=C3C=2)C=NC=1NCCC1=CC=NC=C1 LZHSSLFNBGDQAE-UHFFFAOYSA-N 0.000 claims 2
- PITNNMGYGOMBPE-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1C(N=C1)=CN=C1NCCC1=CC=NC=C1 PITNNMGYGOMBPE-UHFFFAOYSA-N 0.000 claims 2
- GXGOMPRVQQHTLM-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound C1=C(Cl)C(F)=CC=C1C(N=C1)=CN=C1NCCC1=CC=NC=C1 GXGOMPRVQQHTLM-UHFFFAOYSA-N 0.000 claims 2
- QZLRBSCJIUAURU-UHFFFAOYSA-N 5-(4-methoxyphenyl)-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound C1=CC(OC)=CC=C1C(N=C1)=CN=C1NCCC1=CC=NC=C1 QZLRBSCJIUAURU-UHFFFAOYSA-N 0.000 claims 2
- RHIKSYCSRVOQNL-UHFFFAOYSA-N 5-(4-methylsulfanylphenyl)-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound C1=CC(SC)=CC=C1C(N=C1)=CN=C1NCCC1=CC=NC=C1 RHIKSYCSRVOQNL-UHFFFAOYSA-N 0.000 claims 2
- VXOJKQCKVXCNRQ-UHFFFAOYSA-N 5-[[[5-(4-hydroxyphenyl)pyridin-3-yl]amino]methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1CNC1=CN=CC(C=2C=CC(O)=CC=2)=C1 VXOJKQCKVXCNRQ-UHFFFAOYSA-N 0.000 claims 2
- JWHXMIHTTACQGE-UHFFFAOYSA-N 5-[[[5-(4-hydroxyphenyl)pyridin-3-yl]amino]methyl]benzene-1,3-diol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC=2C=C(O)C=C(O)C=2)=C1 JWHXMIHTTACQGE-UHFFFAOYSA-N 0.000 claims 2
- XEWSGSSLPUACOK-UHFFFAOYSA-N 5-naphthalen-2-yl-n-(2-pyridin-3-ylethyl)pyrazin-2-amine Chemical compound C=1N=C(C=2C=C3C=CC=CC3=CC=2)C=NC=1NCCC1=CC=CN=C1 XEWSGSSLPUACOK-UHFFFAOYSA-N 0.000 claims 2
- UQMWLKWOXBBYQC-UHFFFAOYSA-N 5-naphthalen-2-yl-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound C=1N=C(C=2C=C3C=CC=CC3=CC=2)C=NC=1NCCC1=CC=NC=C1 UQMWLKWOXBBYQC-UHFFFAOYSA-N 0.000 claims 2
- FZNGQVBOWZHMTR-UHFFFAOYSA-N 5-pyridin-4-yl-n-(thiophen-2-ylmethyl)pyrazin-2-amine Chemical compound C=1C=CSC=1CNC(N=C1)=CN=C1C1=CC=NC=C1 FZNGQVBOWZHMTR-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- LTSILIGBYDNMLK-UHFFFAOYSA-N [4-[5-(2-pyridin-4-ylethylamino)pyrazin-2-yl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C(N=C1)=CN=C1NCCC1=CC=NC=C1 LTSILIGBYDNMLK-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- SSQUKXWXMGWFMB-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-[5-(2-pyridin-4-ylethylamino)pyrazin-2-yl]benzamide Chemical compound OCCNC(=O)C1=CC=CC(C=2N=CC(NCCC=3C=CN=CC=3)=NC=2)=C1 SSQUKXWXMGWFMB-UHFFFAOYSA-N 0.000 claims 2
- FUMUAJDSRAMUKF-UHFFFAOYSA-N n-(2-pyridin-4-ylethyl)-5-(3,4,5-trimethoxyphenyl)pyrazin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC(NCCC=3C=CN=CC=3)=NC=2)=C1 FUMUAJDSRAMUKF-UHFFFAOYSA-N 0.000 claims 2
- WEXILEUTEVKWOA-UHFFFAOYSA-N n-(2-pyridin-4-ylethyl)-5-[3-(trifluoromethoxy)phenyl]pyrazin-2-amine Chemical compound FC(F)(F)OC1=CC=CC(C=2N=CC(NCCC=3C=CN=CC=3)=NC=2)=C1 WEXILEUTEVKWOA-UHFFFAOYSA-N 0.000 claims 2
- DWEALZLVUKJMKF-UHFFFAOYSA-N n-(2-pyridin-4-ylethyl)-5-[4-(trifluoromethoxy)phenyl]pyrazin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(N=C1)=CN=C1NCCC1=CC=NC=C1 DWEALZLVUKJMKF-UHFFFAOYSA-N 0.000 claims 2
- CIDPLOHBWNIWAD-UHFFFAOYSA-N n-(2-pyridin-4-ylethyl)-5-quinolin-3-ylpyrazin-2-amine Chemical compound C=1N=C(C=2C=C3C=CC=CC3=NC=2)C=NC=1NCCC1=CC=NC=C1 CIDPLOHBWNIWAD-UHFFFAOYSA-N 0.000 claims 2
- ORGALCWPFYIKDU-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-[5-(2-pyridin-4-ylethylamino)pyrazin-2-yl]benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C(C=2N=CC(NCCC=3C=CN=CC=3)=NC=2)C=C1 ORGALCWPFYIKDU-UHFFFAOYSA-N 0.000 claims 2
- GNVQGGYFACLKOQ-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-5-pyridin-4-ylpyrazin-2-amine Chemical compound ClC1=CC=CC(CNC=2N=CC(=NC=2)C=2C=CN=CC=2)=C1 GNVQGGYFACLKOQ-UHFFFAOYSA-N 0.000 claims 2
- CWTKNQOXFLIHKY-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-5-pyridin-4-ylpyrazin-2-amine Chemical compound C1=CC(OC)=CC=C1CNC1=CN=C(C=2C=CN=CC=2)C=N1 CWTKNQOXFLIHKY-UHFFFAOYSA-N 0.000 claims 2
- RZNQROCYNBHOBO-UHFFFAOYSA-N n-[3-[5-[(3-hydroxyphenyl)methylamino]pyridin-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=C(NCC=3C=C(O)C=CC=3)C=NC=2)=C1 RZNQROCYNBHOBO-UHFFFAOYSA-N 0.000 claims 2
- FDFAKRAZWVSGAX-UHFFFAOYSA-N n-[4-[5-[(3-hydroxyphenyl)methylamino]pyridin-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CN=CC(NCC=2C=C(O)C=CC=2)=C1 FDFAKRAZWVSGAX-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
- ILWFNKLXPUKLEP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)-2-fluorobenzene Chemical group FC1=CC(CCl)=CC=C1Cl ILWFNKLXPUKLEP-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- IFEJUANYABWWIB-UHFFFAOYSA-N 3-[5-(4-chloroanilino)pyridin-3-yl]phenol Chemical compound OC1=CC=CC(C=2C=C(NC=3C=CC(Cl)=CC=3)C=NC=2)=C1 IFEJUANYABWWIB-UHFFFAOYSA-N 0.000 claims 1
- PHQIODSUHZHHDH-UHFFFAOYSA-N 3-[5-(4-methoxyanilino)pyridin-3-yl]benzamide Chemical compound C1=CC(OC)=CC=C1NC1=CN=CC(C=2C=C(C=CC=2)C(N)=O)=C1 PHQIODSUHZHHDH-UHFFFAOYSA-N 0.000 claims 1
- IUZKQQXPXLIICJ-UHFFFAOYSA-N 3-[5-(4-methoxyanilino)pyridin-3-yl]phenol Chemical compound C1=CC(OC)=CC=C1NC1=CN=CC(C=2C=C(O)C=CC=2)=C1 IUZKQQXPXLIICJ-UHFFFAOYSA-N 0.000 claims 1
- ZUMKAZPRYGVAFY-UHFFFAOYSA-N 3-[5-(furan-3-ylmethylamino)pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(NCC3=COC=C3)C=NC=2)=C1 ZUMKAZPRYGVAFY-UHFFFAOYSA-N 0.000 claims 1
- BBKPCPRBAVUGGG-UHFFFAOYSA-N 3-[5-(naphthalen-2-ylamino)pyridin-3-yl]phenol Chemical compound OC1=CC=CC(C=2C=C(NC=3C=C4C=CC=CC4=CC=3)C=NC=2)=C1 BBKPCPRBAVUGGG-UHFFFAOYSA-N 0.000 claims 1
- JDTZKTUXMAUEAS-UHFFFAOYSA-N 3-[[[5-[3-(hydroxymethyl)phenyl]pyridin-3-yl]amino]methyl]phenol Chemical compound OCC1=CC=CC(C=2C=C(NCC=3C=C(O)C=CC=3)C=NC=2)=C1 JDTZKTUXMAUEAS-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000006500 3-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC(F)(F)F)=C1[H])C([H])([H])* 0.000 claims 1
- COMIATJOPUPKPV-UHFFFAOYSA-N 4-[5-(1,3-benzodioxol-5-ylmethylamino)pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=CC(NCC=2C=C3OCOC3=CC=2)=C1 COMIATJOPUPKPV-UHFFFAOYSA-N 0.000 claims 1
- PDQIJMRBRIKYEE-UHFFFAOYSA-N 4-[5-(2-pyridin-4-ylethylamino)pyrazin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C(N=C1)=CN=C1NCCC1=CC=NC=C1 PDQIJMRBRIKYEE-UHFFFAOYSA-N 0.000 claims 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- XQDOAIXICYJWPF-UHFFFAOYSA-N 5-pyridin-4-yl-n-[[3-(trifluoromethoxy)phenyl]methyl]pyridin-3-amine Chemical compound FC(F)(F)OC1=CC=CC(CNC=2C=C(C=NC=2)C=2C=CN=CC=2)=C1 XQDOAIXICYJWPF-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 206010003225 Arteriospasm coronary Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 230000001594 aberrant effect Effects 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- TUWZZXGAUMSUOB-UHFFFAOYSA-N benzyl piperidine-1-carboxylate Chemical compound C1CCCCN1C(=O)OCC1=CC=CC=C1 TUWZZXGAUMSUOB-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- DNXZRZYDHGTDKX-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-5-pyridin-4-ylpyrazin-2-amine Chemical compound C=1C=C2OCOC2=CC=1CNC(N=C1)=CN=C1C1=CC=NC=C1 DNXZRZYDHGTDKX-UHFFFAOYSA-N 0.000 claims 1
- SKCZQCYUISITHA-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-[5-(naphthalen-2-ylamino)pyridin-3-yl]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC(C=2C=C(NC=3C=C4C=CC=CC4=CC=3)C=NC=2)=C1 SKCZQCYUISITHA-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Claims (17)
[上式において、
R1及びR2は共に1つの環系を形成するか、又は
R1はHであり、且つR2は2−ピリジン−4−イル−エチル;3−クロロ−ベンジル;ベンゾ[1,3]ジオキソール−4−イルメチル;4−スルホンアミド−ベンジル;ベンジル;チオフェン−2−イルメチル;1−フェニル−エチル;4−(4−アミノ−ベンゾイルアミノ)−フェニル;4−メトキシ−ベンジル;1−ヒドロキシメチル−2−メチル−プロピル;2−ピリジン−3−イル−エチル;4−フェノキシ−フェニル;4−フルオロ−フェニル;4−[エチル−(2−ヒドロキシ−エチル)−アミノ]−フェニル;例えばエチル、プロピル、3−ヒドロキシ−2,2−ジメチル−プロピル、3−ヒドロキシ−プロピル、2−メトキシ−エチル、2−ヒドロキシ−エチル、2−ヒドロキシメチル−3−メチル−ブチル、1−ヒドロキシメチル−プロピル、2−モルホリン−4−イル−エチル、フラン−2−イル−メチルなどを含む場合によって置換されているC1〜C6のアルキル;シクロヘキサンなどを含む場合によって置換されているC3〜C6のシクロアルキル;又は窒素及び酸素から選択されるヘテロ原子を1〜3個有する場合によって置換されている5〜7員環、好ましくはピペラジン環、[1,4]ジアゼパン若しくはピロリジン環であって、ここでR2は場合によって、炭素原子1〜3個を含むリンカーによって骨格に結合しており、
R3はベンゾフラン−2−イル;ナフタレン−2−イル;3−4−メトキシ−フェニル;4−チオメチル−フェニル;ベンゾチオフェン−2−イル;4−ピリジル;4−メトキシ−フェニル;キノリン−3−イル;ベンゾ[1,3]ジオキソール−5−イル;4−ヒドロキシ−フェニル;4−トリフルオロメトキシ−フェニル;3−クロロ−4−ピリジル;3−4−5−メトキシ−フェニル;5−アセチル−チオフェン−2−イル;3−トリフルオロメトキシ−フェニル;4−ヒドロキシメチル−フェニル;N−(4−メトキシ−フェニル)−ベンズアミド−4−イル;3−フルオロ−4−クロロ−フェニル;N−(2−ヒドロキシ−エチル)−4−ベンズアミド−4−イル;3−ヒドロキシ−フェニル;3−アセチルアミノ−フェニル;キノリン−7−イル;2−メトキシ−5−イソプロピル−フェニル;3−ヒドロキシメチルフェニル;3−ピリジル;ヘキサ−1−エニル;4−シアノ−フェニル;チオフェン−3−イル;3−ニトロ−フェニル;3−クロロ−フェニル;2−メトキシ−フェニル;4−イソプロピル−フェニルであり、
R4及びR5は共に1つの環を形成するか、又は
R4はH若しくはメチルであり、且つR5は3−ヒドロキシ−フェニル;3−ヒドロキシベンゾイル;4−ブロモ−ベンジル;4−メトキシベンジル;2,5−ヒドロキシベンジル;3−ヒドロキシ−4−メトキシ−ベンジル;3−クロロ−ベンジル;3−フルオロ−4−クロロ−ベンジル;3−アミノ−ベンジル;3−トリフルオロメトキシ−ベンジル;4−ヒドロキシ−ベンジル;4−アミノ−ベンジル;1H−インドール−6−イル;3−ヒドロキシ−ベンジル;ナフタレン−2−イル−メチル;ベンゾ{1,3}ジオキソール−4−イルメチル;3,4−フルオロ−ベンジル;3,4−クロロ−ベンジル;フラン−3−イル−メチル;4−メトキシ−フェニル;4−クロロ−ベンジル;3−ニトロ−フェニル;3,4−メトキシ−フェニル;3−ブロモ−フェニル;4−クロロ−フェニル;フェニル;3−クロロ−フェニル;2−ナフチル;ピリジン−3−イル−メチル;ピリジン−4−イル−メチル;キノリン−3−イル−メチル;4−イソプロピル−フェニル;4−クロロ−ベンジル;3,4−メトキシ−ベンジル;3−フルオロ−4−クロロ−フェニル;4−トリフルオロメトキシ−フェニル;4−シアノ−フェニル;4−メトキシベンジル、4−メトキシ−3−ヒドロキシベンジル;ピリジン−4−イル−エチル;ピペリジン−1−カルボン酸ベンジルエステル3−イル−メチル;シクロヘキサン−メチル;4−クロロベンゾイル;ピロリジン−2−イル−メチル;例えばエチル、プロピル、3−ヒドロキシ−2,2−ジメチル−プロピル、3−ヒドロキシ−プロピル、2−メトキシ−エチル、2−ヒドロキシ−エチル、2−ヒドロキシメチル−3−メチル−ブチル、1−ヒドロキシメチル−プロピル、2−モルホリン−4−イル−エチル、フラン−2−イル−メチルなどを含む場合によって置換されているC1〜C6のアルキル;例えばシクロヘキサンなどを含む場合によって置換されているC5〜C7のシクロアルキル;又は例えばピペラジン環、[1,4]ジアゼパン若しくはピロリジン環などを含む、窒素及び酸素から選択されるヘテロ原子を1〜3個有する場合によって置換されている5〜7員環であって、ここでR5は場合によって、炭素原子1〜3個を含むリンカーによって骨格に結合しており、
R6は3−カルバモイル−フェニル;4−ヒドロキシ−フェニル;4−アミノ−フェニル;3−アミノ−フェニル;フェニル;1H−インドール−5−イル;4−ピリジル;3−ヒドロキシ−フェニル;ベンゾ[1,3]ジオキソール−5−イル;3−(2−ヒドロキシ−エチルカルバモイル)−フェニル;3−ヒドロキシメチル−フェニル;3−アセチルアミノ−フェニル;4−ヒドロキシメチル−フェニル;3−(2−ジメチルアミノ−エチルカルバモイル)−フェニル;チオフェン−3−イル;3−ピリジル;3,4−メトキシ−フェニル;6−ブロモ−1−カルボン酸tert−ブチルエステル−インドール−2−イル;3−(2−ヒドロキシ−エチルカルバモイル)−フェニル;3−メタンスルホニルアミノ−フェニル;3−トリフルオロメトキシ−フェニル;4−ヒドロキシメチル−フェニル;4−メタンスルホニル−フェニル;キノリン−3−イル;5−メトキシ−ピリジン−3−イル;4−カルバモイル−フェニル;4−アセチルアミノ−フェニル;4−メチルカルバモイル−フェニル;4−(2−ヒドロキシ−エチルカルバモイル)−フェニル;キノリン−4−イル;キノリン−5−イル;イソキノリン−4−イル;1H−ピラゾール−4−イル;3−クロロ−ピリジン−4−イル;3−メトキシ−ピリジン−5−イル;4−メトキシ−ピリジン−5−イル;2−メチル−ピリジン−4−イル;ベンゾチオフェン−2−イル;3−クロロ−ピリジン−4−イル;1H−ピラゾール−3−イル;イソキノリン−3−イル;4−カルバモイル−フェニル;4−カルバモイル−フェニル;3−(2−ヒドロキシ−エチルカルバモイル)−フェニルである]。 A compound selected from the specific group of compounds comprising or consisting of compounds of formula (I) or (II).
[In the above formula,
R1 and R2 together form a ring system, or R1 is H and R2 is 2-pyridin-4-yl-ethyl; 3-chloro-benzyl; benzo [1,3] dioxol-4- 4-sulfonamido-benzyl; benzyl; thiophen-2-ylmethyl; 1-phenyl-ethyl; 4- (4-amino-benzoylamino) -phenyl; 4-methoxy-benzyl; 1-hydroxymethyl-2-methyl 2-propyl-3-yl-ethyl; 4-phenoxy-phenyl; 4-fluoro-phenyl; 4- [ethyl- (2-hydroxy-ethyl) -amino] -phenyl; for example ethyl, propyl, 3- Hydroxy-2,2-dimethyl-propyl, 3-hydroxy-propyl, 2-methoxy-ethyl, 2-hydroxy-ethyl, 2- C1-C6 alkyl optionally substituted, including hydroxymethyl-3-methyl-butyl, 1-hydroxymethyl-propyl, 2-morpholin-4-yl-ethyl, furan-2-yl-methyl, etc .; cyclohexane, etc. Optionally substituted C3-C6 cycloalkyl; or optionally substituted 5-7 membered ring having 1 to 3 heteroatoms selected from nitrogen and oxygen, preferably a piperazine ring, [1 , 4] diazepane or pyrrolidine ring, wherein R2 is optionally linked to the skeleton by a linker containing 1 to 3 carbon atoms;
R3 is benzofuran-2-yl; naphthalen-2-yl; 3-4-methoxy-phenyl; 4-thiomethyl-phenyl; benzothiophen-2-yl; 4-pyridyl; 4-methoxy-phenyl; quinolin-3-yl Benzo [1,3] dioxol-5-yl; 4-hydroxy-phenyl; 4-trifluoromethoxy-phenyl; 3-chloro-4-pyridyl; 3-4-5-methoxy-phenyl; 2-Trifluoromethoxy-phenyl; 4-hydroxymethyl-phenyl; N- (4-methoxy-phenyl) -benzamido-4-yl; 3-fluoro-4-chloro-phenyl; N- (2 -Hydroxy-ethyl) -4-benzamido-4-yl; 3-hydroxy-phenyl; 3-acetylamino-phenyl; 2-Methoxy-5-isopropyl-phenyl; 3-hydroxymethylphenyl; 3-pyridyl; hexa-1-enyl; 4-cyano-phenyl; thiophen-3-yl; 3-nitro-phenyl; 3-chloro-phenyl; 2-methoxy-phenyl; 4-isopropyl-phenyl;
R4 and R5 together form a ring, or R4 is H or methyl and R5 is 3-hydroxy-phenyl; 3-hydroxybenzoyl; 4-bromo-benzyl; 4-methoxybenzyl; 2,5 3-hydroxybenzyl; 3-hydroxy-4-methoxy-benzyl; 3-chloro-benzyl; 3-fluoro-4-chloro-benzyl; 3-amino-benzyl; 3-trifluoromethoxy-benzyl; 4-hydroxy-benzyl; 4-amino-benzyl; 1H-indol-6-yl; 3-hydroxy-benzyl; naphthalen-2-yl-methyl; benzo {1,3} dioxol-4-ylmethyl; 3,4-fluoro-benzyl; 4-chloro-benzyl; furan-3-yl-methyl; 4-methoxy-phenyl; 4-chloro-benzyl 3-nitro-phenyl; 3,4-methoxy-phenyl; 3-bromo-phenyl; 4-chloro-phenyl; phenyl; 3-chloro-phenyl; 2-naphthyl; pyridin-3-yl-methyl; Quinolin-3-yl-methyl; 4-isopropyl-phenyl; 4-chloro-benzyl; 3,4-methoxy-benzyl; 3-fluoro-4-chloro-phenyl; 4-trifluoromethoxy-phenyl 4-cyanobenzyl, 4-methoxy-3-hydroxybenzyl; pyridin-4-yl-ethyl; piperidine-1-carboxylic acid benzyl ester 3-yl-methyl; cyclohexane-methyl; Benzoyl; pyrrolidin-2-yl-methyl; such as ethyl, propyl, 3-hydroxy-2, -Dimethyl-propyl, 3-hydroxy-propyl, 2-methoxy-ethyl, 2-hydroxy-ethyl, 2-hydroxymethyl-3-methyl-butyl, 1-hydroxymethyl-propyl, 2-morpholin-4-yl-ethyl Optionally substituted C1-C6 alkyl, including furan-2-yl-methyl, etc .; optionally substituted C5-C7 cycloalkyl, including cyclohexane, etc .; or, for example, a piperazine ring, [1,4 A 5- to 7-membered ring optionally substituted with 1 to 3 heteroatoms selected from nitrogen and oxygen, including a diazepane or pyrrolidine ring, wherein R5 is optionally carbon atoms 1 to Linked to the skeleton by a linker containing three,
R6 is 3-carbamoyl-phenyl; 4-hydroxy-phenyl; 4-amino-phenyl; 3-amino-phenyl; phenyl; 1H-indol-5-yl; 4-pyridyl; 3-hydroxy-phenyl; 3] dioxol-5-yl; 3- (2-hydroxy-ethylcarbamoyl) -phenyl; 3-hydroxymethyl-phenyl; 3-acetylamino-phenyl; 4-hydroxymethyl-phenyl; 3- (2-dimethylamino- Ethylcarbamoyl) -phenyl; thiophen-3-yl; 3-pyridyl; 3,4-methoxy-phenyl; 6-bromo-1-carboxylic acid tert-butyl ester-indol-2-yl; 3- (2-hydroxy- Ethylcarbamoyl) -phenyl; 3-methanesulfonylamino-phenyl; 3-tri 4-hydroxymethyl-phenyl; 4-methanesulfonyl-phenyl; quinolin-3-yl; 5-methoxy-pyridin-3-yl; 4-carbamoyl-phenyl; 4-acetylamino-phenyl; 4-methyl 4- (2-hydroxy-ethylcarbamoyl) -phenyl; quinolin-4-yl; quinolin-5-yl; isoquinolin-4-yl; 1H-pyrazol-4-yl; 3-chloro-pyridine-4 3-yl-pyridin-5-yl; 4-methoxy-pyridin-5-yl; 2-methyl-pyridin-4-yl; benzothiophen-2-yl; 3-chloro-pyridin-4-yl; 1H-pyrazol-3-yl; isoquinolin-3-yl; 4-carbamoyl-phenyl; 4-carba Yl - phenyl; 3- (2-hydroxy - ethylcarbamoyl) - phenyl].
R2が2−ピリジン−4−イル−エチル、チオフェン−2−イルメチル、4−スルホンアミド−ベンジル、又は3−クロロ−ベンジルであり、
R3がベンゾチオフェン−2−イル、ナフタレン−2−イル、3,4−メトキシ−フェニル、又は4−ピリジルであり、
R4が水素であり、
R5が3−ヒドロキシ−ベンジル、4−クロロ−ベンジル、ナフタレン−2−イル−メチル、ベンゾ[1,3]ジオキソール−4−イルメチル、3,4−フルオロ−ベンジル、3,4−クロロ−ベンジル、又はフラン−3−イル−メチルであり、且つ
R6が3−カルバモイル−フェニル、4−ヒドロキシ−フェニル、又は4−ピリジルである
請求項1に記載の化合物。 R1 is hydrogen;
R2 is 2-pyridin-4-yl-ethyl, thiophen-2-ylmethyl, 4-sulfonamido-benzyl, or 3-chloro-benzyl;
R3 is benzothiophen-2-yl, naphthalen-2-yl, 3,4-methoxy-phenyl, or 4-pyridyl;
R4 is hydrogen,
R5 is 3-hydroxy-benzyl, 4-chloro-benzyl, naphthalen-2-yl-methyl, benzo [1,3] dioxol-4-ylmethyl, 3,4-fluoro-benzyl, 3,4-chloro-benzyl, Or Furan-3-yl-methyl and R6 is 3-carbamoyl-phenyl, 4-hydroxy-phenyl, or 4-pyridyl.
[5−(3,4−ジメトキシ−フェニル)−ピラジン−2−イル]−(2−ピリジン−4−イル−エチル)−アミン;
4−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−フェノール;
(2−ピリジン−4−イル−エチル)−[5−(4−トリフルオロメトキシ−フェニル)−ピラジン−2−イル]−アミン;
(2−ピリジン−4−イル−エチル)−[5−(3,4,5−トリメトキシ−フェニル)−ピラジン−2−イル]−アミン;
(2−ピリジン−4−イル−エチル)−[5−(3−トリフルオロメトキシ−フェニル)−ピラジン−2−イル]−アミン;
(5−ベンゾ[1,3]ジオキソール−5−イル−ピラジン−2−イル)−(2−ピリジン−4−イル−エチル)−アミン;
4−(5−ベンジルアミノ−ピラジン−2−イル)−フェノール;
N−(2−ヒドロキシ−エチル)−3−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−ベンズアミド;
N−(4−メトキシ−フェニル)−4−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−ベンズアミド;
[5−(4−メトキシ−フェニル)−ピラジン−2−イル]−(2−ピリジン−4−イル−エチル)−アミン;
{4−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−フェニル}−メタノール;
(5−ナフタレン−2−イル−ピラジン−2−イル)−(2−ピリジン−4−イル−エチル)−アミン;
ベンゾ[1,3]ジオキソール−5−イルメチル−(5−ピリジン−4−イル−ピラジン−2−イル)−アミン;
(4−メトキシ−ベンジル)−(5−ピリジン−4−イル−ピラジン−2−イル)−アミン;
[5−(3−クロロ−4−フルオロ−フェニル)−ピラジン−2−イル]−(2−ピリジン−4−イル−エチル)−アミン;
1−{5−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−チオフェン−2−イル}−エタノン;
(5−ベンゾフラン−2−イル−ピラジン−2−イル)−(2−ピリジン−4−イル−エチル)−アミン;
(5−ベンゾ[b]チオフェン−2−イル−ピラジン−2−イル)−(2−ピリジン−4−イル−エチル)−アミン;
[5−(4−メチルスルファニル−フェニル)−ピラジン−2−イル]−(2−ピリジン−4−イル−エチル)−アミン;
(2−ピリジン−4−イル−エチル)−(5−キノリン−3−イル−ピラジン−2−イル)−アミン;
(5−ピリジン−4−イル−ピラジン−2−イル)−チオフェン−2−イルメチル−アミン;
3−メチル−2−(5−ピリジン−4−イル−ピラジン−2−イルアミノ)−ブタン−1−オール;
2−[1−(5−ピリジン−4−イル−ピラジン−2−イル)−ピペリジン−2−イル]−エタノール;
4−[5−(3−クロロ−ベンジルアミノ)−ピラジン−2−イル]−フェノール;
(3−クロロ−ベンジル)−(5−ピリジン−4−イル−ピラジン−2−イル)−アミン;
4−[5−(1−フェニル−エチルアミノ)−ピラジン−2−イル]−フェノール;
(5−ナフタレン−2−イル−ピラジン−2−イル)−(2−ピリジン−3−イル−エチル)−アミン;
4−アミノ−N−{4−[5−(3−クロロ−ピリジン−4−イル)−ピラジン−2−イルアミノ]−フェニル}−ベンズアミド;
4−[(5−ピリジン−4−イル−ピラジン−2−イルアミノ)−メチル]−ベンゼンスルホンアミド;
[3,4’]ビピリジニル−5−イル−ナフタレン−2−イルメチル−アミン;
4−{5−[(ナフタレン−2−イルメチル)−アミノ]−ピリジン−3−イル}−フェノール;
3−[5−(3,4−ジクロロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3,4−ジクロロ−ベンジル)−アミン;
4−[5−(3,4−ジクロロ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(4−クロロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(4−クロロ−ベンジル)−アミン;
4−[5−(4−クロロ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3,4−ジフルオロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3,4−ジフルオロ−ベンジル)−アミン;
4−[5−(3,4−ジメトキシ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−{5−[(ベンゾ[1,3]ジオキソール−5−イルメチル)−アミノ]−ピリジン−3−イル}−ベンズアミド;
ベンゾ[1,3]ジオキソール−5−イルメチル−[3,4’]ビピリジニル−5−イル−アミン;
4−{5−[(ベンゾ[1,3]ジオキソール−5−イルメチル)−アミノ)−ピリジン−3−イル]−フェノール;
4−[5−(3,4−ジフルオロ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−N−(2−ヒドロキシ−エチル)−ベンズアミド;
3−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−[(5−ベンゾ[1,3]ジオキソール−5−イル−ピリジン−3−イルアミノ)−メチル]−フェノール;
3−([3,4’]ビピリジニル−5−イルアミノメチル)−フェノール;
3−{[5−(4−ヒドロキシメチル−フェニル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
N−{3−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−フェニル}−アセトアミド;
(5−(4’−ヒドロキシ−フェニル)−ピリジン−3−イル)−(3−ヒドロキシ−ベンジル)−アミン;
3−{[5−(3−ヒドロキシメチル−フェニル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
(5−(3’−ヒドロキシ−フェニル)−ピリジン−3−イル)−(3−ヒドロキシ−ベンジル)−アミン;
3−{5−[(フラン−3−イルメチル)−アミノ]−ピリジン−3−イル}−ベンズアミド;
[3,4’]ビピリジニル−5−イル−フラン−3−イルメチル−アミン;
4−{5−[(フラン−3−イルメチル)−アミノ]−ピリジン−3−イル}−フェノール;
3−{5−[(ピリジン−3−イルメチル)−アミノ]−ピリジン−3−イル}−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3−クロロ−フェニル)−アミン;
3−[5−(3−ブロモ−フェニルアミノ)−ピリジン3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3−ブロモ−フェニル)−アミン;
[3,4’]ビピリジニル−5−イル−(3−ニトロ−フェニル)−アミン;
3−[5−(4−メトキシ−フェニルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−[5−(4−メトキシ−フェニルアミノ)−ピリジン−3−イル]−フェノール;
N−(2−ジメチルアミノ−エチル)−3−[5−(ナフタレン−2−イルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−[5−(ナフタレン−2−イルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(4−クロロ−フェニルアミノ)−ピリジン−3−イル]−フェノール;
3−[(3’−クロロ−[3,4’]−ビピリジニル−5−イルアミノ)−メチル]−フェノール;
3−[(5−キノリン−5−イル−ピリジン−3−イルアミノ)−メチル]−フェノール;
3−{[5−(1H−ピラゾール−3−イル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
3−[(5−イソキノリン−4−イル−ピリジン−3−イルアミノ)−メチル]−フェノール;
N−{4−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−フェニル}−アセトアミド;
4−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−{[5−(4−アミノ−フェニル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
3−{[5−(1H−インドール−5−イル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
3−[(5’−メトキシ−[3,3’]ビピリジニル−5−イルアミノ)メチル]−フェノール;
3−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−N−(2−ヒドロキシ−エチル)−ベンズアミド;
3−[(5−フェニル−ピリジン−3−イルアミノ)−メチル]−フェノール;
3−{[5−(3−アミノ−フェニル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
4−{5−[(3−ヒドロキシ−ベンジル)−メチル−アミノ]−ピリジン−3−イル}−フェノール;
5−{[5−(4−ヒドロキシ−フェニル)−ピリジン−3−イルアミノ]−メチル}−ベンゼン−1,3−ジオール;
3−[5−(3,5−ジヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(4−ブロモ−ベンジル)−アミン;
[3,4’]ビピリジニル−5−イル−(3−クロロ−ベンジル)−アミン;
4−[5−(3−クロロ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3−クロロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(4−メトキシ−ベンジル)−アミン;
4−[5−(4−メトキシ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(4−メトキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−[5−(4−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
5−{[5−(4−ヒドロキシ−フェニル)−ピリジン−3−イルアミノ]−メチル}−2−メトキシ−フェノール;
3−[5−(3−ヒドロキシ−4−メトキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−([3,4’]ビピリジニル−5−イルアミノ)−フェノール;
4−[5−(3−ヒドロキシ−フェニルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3−ヒドロキシ−フェニルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−シクロヘキシルメチル−アミン;
4−[5−(シクロヘキシルメチル−アミノ)−ピリジン−3−イル]−フェノール;
3−[5−(シクロヘキシルメチル−アミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(4−クロロ−3−フルオロ−ベンジル)−アミン;
3−[5−(4−クロロ−3−フルオロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3−トリフルオロメトキシ−ベンジル)−アミン;
4−[5−(3−トリフルオロメトキシ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3−トリフルオロメトキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−ピロリジン−2−イルメチル−アミン;
4−{5−[(ピロリジン−2−イルメチル)−アミノ]−ピリジン−3−イル}−フェノール;及び
3−{5−[(ピロリジン−2−イルメチル)−アミノ]−ピリジン−3−イル}−ベンズアミド、
並びに下記に挙げた化合物:
[5−(3,4−ジメトキシ−フェニル)−ピラジン−2−イル]−(2−ピリジン−4−イル−エチル)−アミン;
4−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−フェノール;
(2−ピリジン−4−イル−エチル)−[5−(4−トリフルオロメトキシ−フェニル)−ピラジン−2−イル]−アミン;
(2−ピリジン−4−イル−エチル)−[5−(3,4,5−トリメトキシ−フェニル)−ピラジン−2−イル]−アミン;
(2−ピリジン−4−イル−エチル)−[5−(3−トリフルオロメトキシ−フェニル)−ピラジン−2−イル]−アミン;
(5−ベンゾ[1,3]ジオキソール−5−イル−ピラジン−2−イル)−(2−ピリジン−4−イル−エチル)−アミン;
4−(5−ベンジルアミノ−ピラジン−2−イル)−フェノール;
N−(2−ヒドロキシ−エチル)−3−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−ベンズアミド;
N−(4−メトキシ−フェニル)−4−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−ベンズアミド;
[5−(4−メトキシ−フェニル)−ピラジン−2−イル]−(2−ピリジン−4−イル−エチル)−アミン;
{4−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−フェニル}−メタノール;
(5−ナフタレン−2−イル−ピラジン−2−イル)−(2−ピリジン−4−イル−エチル)−アミン;
ベンゾ[1,3]ジオキソール−5−イルメチル−5−ピリジン−4−イル−ピラジン−2−イル)−アミン;
(4−メトキシ−ベンジル)−(5−ピリジン−4−イル−ピラジン−2−イル)−アミン;
[5−(3−クロロ−4−フルオロ−フェニル)−ピラジン−2−イル]−(2−ピリジン−4−イル−エチル)−アミン;
1−{5−[5−(2−ピリジン−4−イル−エチルアミノ)−ピラジン−2−イル]−チオフェン−2−イル}−エタノン;
(5−ベンゾフラン−2−イル−ピラジン−2−イル)−(2−ピリジン−4−イル−エチル)−アミン;
(5−ベンゾ[b]チオフェン−2−イル−ピラジン−2−イル)−(2−ピリジン−4−イル−エチル)−アミン;
[5−(4−メチルスルファニル−フェニル)−ピラジン−2−イル]−(2−ピリジン−4−イル−エチル)−アミン;
(2−ピリジン−4−イル−エチル)−(5−キノリン−3−イル−ピラジン−2−イル)−アミン;
(5−ピリジン−4−イル−ピラジン−2−イル)−チオフェン−2−イルメチル−アミン;
3−メチル−2−(5−ピリジン−4−イル−ピラジン−2−イルアミノ)−ブタン−1−オール;
2−[1−(5−ピリジン−4−イル−ピラジン−2−イル)−ピペリジン−2−イル]−エタノール;
4−[5−(3−クロロ−ベンジルアミノ)−ピラジン−2−イル]−フェノール;
(3−クロロ−ベンジル)−(5−ピリジン−4−イル−ピラジン−2−イル)−アミン;
4−[5−(1−フェニル−エチルアミノ)−ピラジン−2−イル]−フェノール;
(5−ナフタレン−2−イル−ピラジン−2−イル)−(2−ピリジン−3−イル−エチル)−アミン;
4−アミノ−N−{4−[5−(3−クロロ−ピリジン−4−イル)−ピラジン−2−イルアミノ]−フェニル}−ベンズアミド;
4−[(5−ピリジン−4−イル−ピラジン−2−イルアミノ)−メチル]−ベンゼンスルホンアミド;
[3,4’]ビピリジニル−5−イル−ナフタレン−2−イルメチル−アミン;
4−{5−[(ナフタレン−2−イルメチル)−アミノ]−ピリジン−3−イル}−フェノール;
3−[5−(3,4−ジクロロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3,4−ジクロロ−ベンジル)−アミン;
4−[5−(3,4−ジクロロ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(4−クロロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(4−クロロ−ベンジル)−アミン;
4−[5−(4−クロロ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3,4−ジフルオロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3,4−ジフルオロ−ベンジル)−アミン;
4−[5−(3,4−ジメトキシ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−{5−[(ベンゾ[1,3]ジオキソール−5−イルメチル)−アミノ]−ピリジン−3−イル}−ベンズアミド;
ベンゾ[1,3]ジオキソール−5−イルメチル−[3,4’]ビピリジニル−5−イル−アミン;
4−{5−[(ベンゾ[1,3]ジオキソール−5−イルメチル)−アミノ]−ピリジン−3−イル}−フェノール;
4−[5−(3,4−ジフルオロ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−N−(2−ヒドロキシ−エチル)−ベンズアミド;
3−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−[(5−ベンゾ[1,3]ジオキソール−5−イル−ピリジン−3−イルアミノ)−メチル]−フェノール;
3−([3,4’]ビピリジニル−5−イルアミノメチル)−フェノール;
3−{[5−(4−ヒドロキシメチル−フェニル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
N−{3−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−フェニル}−アセトアミド;
(5−(4’−ヒドロキシ−フェニル)−ピリジン−3−イル)−(3−ヒドロキシ−ベンジル)−アミン;
3−{[5−(3−ヒドロキシメチル−フェニル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
(5−(3’−ヒドロキシ−フェニル)−ピリジン−3−イル)−(3−ヒドロキシ−ベンジル)−アミン;
3−{5−[(フラン−3−イルメチル)−アミノ]−ピリジン−3−イル}−ベンズアミド;
[3,4’]ビピリジニル−5−イル−フラン−3−イルメチル−アミン;
4−{5−[(フラン−3−イルメチル)−アミノ]−ピリジン−3−イル}−フェノール;
3−{5−[(ピリジン−3−イルメチル)−アミノ]−ピリジン−3−イル}−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3−クロロ−フェニル)−アミン;
3−[5−(3−ブロモ−フェニルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3−ブロモ−フェニル)−アミン;
[3,4’]ビピリジニル−5−イル−(3−ニトロ−フェニル)−アミン;
3−[(3’−クロロ−[3,4’]ビピリジニル−5−イルアミノ)−メチル]−フェノール;
3−[(5−キノリン−5−イル−ピリジン−3−イルアミノ)−メチル]−フェノール;
3−{[5−(1H−ピラゾール−3−イル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
3−[(5−イソキノリン−4−イル−ピリジン−3−イルアミノ)メチル]−フェノール;
4−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−{[5−(4−アミノ−フェニル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
3−{[5−(1H−インドール−5−イル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
3−[(5’−メトキシ−[3,3’]ビピリジニル−5−イルアミノ)−メチル]−フェノール;
3−[(5−フェニル−ピリジン−3−イルアミノ)−メチル]−フェノール;
3−{[5−(3−アミノ−フェニル)−ピリジン−3−イルアミノ]−メチル}−フェノール;
5−{[5−(4−ヒドロキシ−フェニル)−ピリジン−3−イルアミノ]−メチル}−ベンゼン−1,3−ジオール;
3−[5−(3,5−ジヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(3−クロロ−ベンジル)−アミン;
3−[5−(3−クロロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(4−メトキシ−ベンジル)−アミン;
4−[5−(4−メトキシ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
5−{[5−(4−ヒドロキシ−フェニル)−ピリジン−3−イルアミノ]−メチル}−2−メトキシ−フェノール;
3−[5−(3−ヒドロキシ−4−メトキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−([3,4’]ビピリジニル−5−イルアミノ)−フェノール;
4−[5−(3−ヒドロキシ−フェニルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3−ヒドロキシ−フェニルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−シクロヘキシルメチル−アミン;
4−[5−(シクロヘキシルメチル−アミノ)−ピリジン−3−イル]−フェノール;
3−[5−(シクロヘキシルメチル−アミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]ビピリジニル−5−イル−(4−クロロ−3−フルオロ−ベンジル)−アミン;
3−[5−(4−クロロ−3−フルオロ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
[3,4’]−ビピリジニル−5−イル−(3−トリフルオロメトキシ−ベンジル)−アミン;
4−[5−(3−トリフルオロメトキシ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
3−[5−(3−トリフルオロメトキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−[5−(4−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
3−{5−[(ピロリジン−2−イルメチル)−アミノ]−ピリジン−3−イル}−ベンズアミド;
4−{5−[(ピロリジン−2−イルメチル)−アミノ]−ピリジン−3−イル}−フェノール;
[3,4’]ビピリジニル−5−イル−ピロリジン−2−イルメチル−アミン;
4−[5−(3−クロロ−ベンジルアミノ)−ピリジン−3−イル]−フェノール;
N−{4−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−フェニル}−アセトアミド;
4−{5−[(3−ヒドロキシ−ベンジル)−メチル−アミノ]−ピリジン−3−イル}−フェノール;
3−[5−(3−ヒドロキシ−ベンジルアミノ)−ピリジン−3−イル]−N−(2−ヒドロキシ−エチル)−ベンズアミド;
3−[5−(4−メトキシ−ベンジルアミノ)−ピリジン−3−イル]−ベンズアミド;
N−[3,4’]ビピリジニル−5−イル−2−(4−クロロ−フェニル)−アセトアミド;及び
[3,4’]ビピリジニル−5−イル−(4−ブロモ−ベンジル)−アミン;
の群から選択される請求項1に記載の化合物。 The compounds listed below :
[5- (3,4-Dimethoxy-phenyl) -pyrazin-2-yl]-(2-pyridin-4-yl-ethyl) -amine;
4- [5- (2-Pyridin-4-yl-ethylamino) -pyrazin-2-yl] -phenol;
(2-pyridin-4-yl-ethyl)-[5- (4-trifluoromethoxy-phenyl) -pyrazin-2-yl] -amine;
(2-pyridin-4-yl-ethyl)-[5- (3,4,5-trimethoxy-phenyl) -pyrazin-2-yl] -amine;
(2-Pyridin-4-yl-ethyl)-[5- (3-trifluoromethoxy-phenyl) -pyrazin-2-yl] -amine;
(5-Benzo [1,3] dioxol-5-yl-pyrazin-2-yl)-(2-pyridin-4-yl-ethyl) -amine;
4- (5-benzylamino-pyrazin-2-yl) -phenol;
N- (2-hydroxy-ethyl) -3- [5- (2-pyridin-4-yl-ethylamino) -pyrazin-2-yl] -benzamide;
N- (4-methoxy-phenyl) -4- [5- (2-pyridin-4-yl-ethylamino) -pyrazin-2-yl] -benzamide;
[5- (4-methoxy-phenyl) -pyrazin-2-yl]-(2-pyridin-4-yl-ethyl) -amine;
{4- [5- (2-Pyridin-4-yl-ethylamino) -pyrazin-2-yl] -phenyl} -methanol;
(5-naphthalen-2-yl-pyrazin-2-yl)-(2-pyridin-4-yl-ethyl) -amine;
Benzo [1,3] dioxol-5-ylmethyl- (5-pyridin-4-yl-pyrazin-2-yl) -amine;
(4-methoxy-benzyl)-(5-pyridin-4-yl-pyrazin-2-yl) -amine;
[5- (3-Chloro-4-fluoro-phenyl) -pyrazin-2-yl]-(2-pyridin-4-yl-ethyl) -amine;
1- {5- [5- (2-Pyridin-4-yl-ethylamino) -pyrazin-2-yl] -thiophen-2-yl} -ethanone;
(5-benzofuran-2-yl-pyrazin-2-yl)-(2-pyridin-4-yl-ethyl) -amine;
(5-Benzo [b] thiophen-2-yl-pyrazin-2-yl)-(2-pyridin-4-yl-ethyl) -amine;
[5- (4-methylsulfanyl-phenyl) -pyrazin-2-yl]-(2-pyridin-4-yl-ethyl) -amine;
(2-pyridin-4-yl-ethyl)-(5-quinolin-3-yl-pyrazin-2-yl) -amine;
(5-pyridin-4-yl-pyrazin-2-yl) -thiophen-2-ylmethyl-amine;
3-methyl-2- (5-pyridin-4-yl-pyrazin-2-ylamino) -butan-1-ol;
2- [1- (5-pyridin-4-yl-pyrazin-2-yl) -piperidin-2-yl] -ethanol;
4- [5- (3-chloro-benzylamino) -pyrazin-2-yl] -phenol;
(3-chloro-benzyl)-(5-pyridin-4-yl-pyrazin-2-yl) -amine;
4- [5- (1-phenyl-ethylamino) -pyrazin-2-yl] -phenol;
(5-Naphthalen-2-yl-pyrazin-2-yl)-(2-pyridin-3-yl-ethyl) -amine;
4-amino-N- {4- [5- (3-chloro-pyridin-4-yl) -pyrazin-2-ylamino] -phenyl} -benzamide;
4-[(5-pyridin-4-yl-pyrazin-2-ylamino) -methyl] -benzenesulfonamide;
[3,4 '] bipyridinyl-5-yl-naphthalen-2-ylmethyl-amine;
4- {5-[(naphthalen-2-ylmethyl) -amino] -pyridin-3-yl} -phenol;
3- [5- (3,4-dichloro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (3,4-dichloro-benzyl) -amine;
4- [5- (3,4-dichloro-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (4-chloro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (4-chloro-benzyl) -amine;
4- [5- (4-Chloro-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (3,4-difluoro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (3,4-difluoro-benzyl) -amine;
4- [5- (3,4-dimethoxy-benzylamino) -pyridin-3-yl] -phenol;
3- {5-[(benzo [1,3] dioxol-5-ylmethyl) -amino] -pyridin-3-yl} -benzamide;
Benzo [1,3] dioxol-5-ylmethyl- [3,4 '] bipyridinyl-5-yl-amine;
4- {5-[(benzo [1,3] dioxol-5-ylmethyl) -amino) -pyridin-3-yl] -phenol;
4- [5- (3,4-difluoro-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -N- (2-hydroxy-ethyl) -benzamide;
3- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -benzamide;
3-[(5-benzo [1,3] dioxol-5-yl-pyridin-3-ylamino) -methyl] -phenol;
3-([3,4 '] bipyridinyl-5-ylaminomethyl) -phenol;
3-{[5- (4-hydroxymethyl-phenyl) -pyridin-3-ylamino] -methyl} -phenol;
N- {3- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -phenyl} -acetamide;
(5- (4′-hydroxy-phenyl) -pyridin-3-yl)-(3-hydroxy-benzyl) -amine;
3-{[5- (3-hydroxymethyl-phenyl) -pyridin-3-ylamino] -methyl} -phenol;
(5- (3′-hydroxy-phenyl) -pyridin-3-yl)-(3-hydroxy-benzyl) -amine;
3- {5-[(furan-3-ylmethyl) -amino] -pyridin-3-yl} -benzamide;
[3,4 '] bipyridinyl-5-yl-furan-3-ylmethyl-amine;
4- {5-[(furan-3-ylmethyl) -amino] -pyridin-3-yl} -phenol;
3- {5-[(pyridin-3-ylmethyl) -amino] -pyridin-3-yl} -benzamide;
[3,4 '] bipyridinyl-5-yl- (3-chloro-phenyl) -amine;
3- [5- (3-bromo-phenylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (3-bromo-phenyl) -amine;
[3,4 '] bipyridinyl-5-yl- (3-nitro-phenyl) -amine;
3- [5- (4-methoxy-phenylamino) -pyridin-3-yl] -benzamide;
3- [5- (4-methoxy-phenylamino) -pyridin-3-yl] -phenol;
N- (2-dimethylamino-ethyl) -3- [5- (naphthalen-2-ylamino) -pyridin-3-yl] -benzamide;
3- [5- (naphthalen-2-ylamino) -pyridin-3-yl] -phenol;
3- [5- (4-chloro-phenylamino) -pyridin-3-yl] -phenol;
3-[(3′-chloro- [3,4 ′]-bipyridinyl-5-ylamino) -methyl] -phenol;
3-[(5-quinolin-5-yl-pyridin-3-ylamino) -methyl] -phenol;
3-{[5- (1H-pyrazol-3-yl) -pyridin-3-ylamino] -methyl} -phenol;
3-[(5-isoquinolin-4-yl-pyridin-3-ylamino) -methyl] -phenol;
N- {4- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -phenyl} -acetamide;
4- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -benzamide;
3-{[5- (4-amino-phenyl) -pyridin-3-ylamino] -methyl} -phenol;
3-{[5- (1H-indol-5-yl) -pyridin-3-ylamino] -methyl} -phenol;
3-[(5′-methoxy- [3,3 ′] bipyridinyl-5-ylamino) methyl] -phenol;
3- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -N- (2-hydroxy-ethyl) -benzamide;
3-[(5-phenyl-pyridin-3-ylamino) -methyl] -phenol;
3-{[5- (3-amino-phenyl) -pyridin-3-ylamino] -methyl} -phenol;
4- {5-[(3-hydroxy-benzyl) -methyl-amino] -pyridin-3-yl} -phenol;
5-{[5- (4-hydroxy-phenyl) -pyridin-3-ylamino] -methyl} -benzene-1,3-diol;
3- [5- (3,5-dihydroxy-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (4-bromo-benzyl) -amine;
[3,4 '] bipyridinyl-5-yl- (3-chloro-benzyl) -amine;
4- [5- (3-chloro-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (3-chloro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (4-methoxy-benzyl) -amine;
4- [5- (4-methoxy-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (4-methoxy-benzylamino) -pyridin-3-yl] -benzamide;
3- [5- (4-hydroxy-benzylamino) -pyridin-3-yl] -benzamide;
5-{[5- (4-hydroxy-phenyl) -pyridin-3-ylamino] -methyl} -2-methoxy-phenol;
3- [5- (3-hydroxy-4-methoxy-benzylamino) -pyridin-3-yl] -benzamide;
3-([3,4 '] bipyridinyl-5-ylamino) -phenol;
4- [5- (3-hydroxy-phenylamino) -pyridin-3-yl] -phenol;
3- [5- (3-hydroxy-phenylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl-cyclohexylmethyl-amine;
4- [5- (cyclohexylmethyl-amino) -pyridin-3-yl] -phenol;
3- [5- (cyclohexylmethyl-amino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (4-chloro-3-fluoro-benzyl) -amine;
3- [5- (4-chloro-3-fluoro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (3-trifluoromethoxy-benzyl) -amine;
4- [5- (3-trifluoromethoxy-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (3-trifluoromethoxy-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl-pyrrolidin-2-ylmethyl-amine;
4- {5-[(pyrrolidin-2-ylmethyl) -amino] -pyridin-3-yl} -phenol; and
3- {5-[(pyrrolidin-2-ylmethyl) -amino] -pyridin-3-yl} -benzamide,
And the compounds listed below:
[5- (3,4-Dimethoxy-phenyl) -pyrazin-2-yl]-(2-pyridin-4-yl-ethyl) -amine;
4- [5- (2-Pyridin-4-yl-ethylamino) -pyrazin-2-yl] -phenol;
(2-pyridin-4-yl-ethyl)-[5- (4-trifluoromethoxy-phenyl) -pyrazin-2-yl] -amine;
(2-pyridin-4-yl-ethyl)-[5- (3,4,5-trimethoxy-phenyl) -pyrazin-2-yl] -amine;
(2-Pyridin-4-yl-ethyl)-[5- (3-trifluoromethoxy-phenyl) -pyrazin-2-yl] -amine;
(5-Benzo [1,3] dioxol-5-yl-pyrazin-2-yl)-(2-pyridin-4-yl-ethyl) -amine;
4- (5-benzylamino-pyrazin-2-yl) -phenol;
N- (2-hydroxy-ethyl) -3- [5- (2-pyridin-4-yl-ethylamino) -pyrazin-2-yl] -benzamide;
N- (4-methoxy-phenyl) -4- [5- (2-pyridin-4-yl-ethylamino) -pyrazin-2-yl] -benzamide;
[5- (4-methoxy-phenyl) -pyrazin-2-yl]-(2-pyridin-4-yl-ethyl) -amine;
{4- [5- (2-Pyridin-4-yl-ethylamino) -pyrazin-2-yl] -phenyl} -methanol;
(5-naphthalen-2-yl-pyrazin-2-yl)-(2-pyridin-4-yl-ethyl) -amine;
Benzo [1,3] dioxol-5-ylmethyl-5-pyridin-4-yl-pyrazin-2-yl) -amine;
(4-methoxy-benzyl)-(5-pyridin-4-yl-pyrazin-2-yl) -amine;
[5- (3-Chloro-4-fluoro-phenyl) -pyrazin-2-yl]-(2-pyridin-4-yl-ethyl) -amine;
1- {5- [5- (2-Pyridin-4-yl-ethylamino) -pyrazin-2-yl] -thiophen-2-yl} -ethanone;
(5-benzofuran-2-yl-pyrazin-2-yl)-(2-pyridin-4-yl-ethyl) -amine;
(5-Benzo [b] thiophen-2-yl-pyrazin-2-yl)-(2-pyridin-4-yl-ethyl) -amine;
[5- (4-methylsulfanyl-phenyl) -pyrazin-2-yl]-(2-pyridin-4-yl-ethyl) -amine;
(2-pyridin-4-yl-ethyl)-(5-quinolin-3-yl-pyrazin-2-yl) -amine;
(5-pyridin-4-yl-pyrazin-2-yl) -thiophen-2-ylmethyl-amine;
3-methyl-2- (5-pyridin-4-yl-pyrazin-2-ylamino) -butan-1-ol;
2- [1- (5-pyridin-4-yl-pyrazin-2-yl) -piperidin-2-yl] -ethanol;
4- [5- (3-chloro-benzylamino) -pyrazin-2-yl] -phenol;
(3-chloro-benzyl)-(5-pyridin-4-yl-pyrazin-2-yl) -amine;
4- [5- (1-phenyl-ethylamino) -pyrazin-2-yl] -phenol;
(5-Naphthalen-2-yl-pyrazin-2-yl)-(2-pyridin-3-yl-ethyl) -amine;
4-amino-N- {4- [5- (3-chloro-pyridin-4-yl) -pyrazin-2-ylamino] -phenyl} -benzamide;
4-[(5-pyridin-4-yl-pyrazin-2-ylamino) -methyl] -benzenesulfonamide;
[3,4 '] bipyridinyl-5-yl-naphthalen-2-ylmethyl-amine;
4- {5-[(naphthalen-2-ylmethyl) -amino] -pyridin-3-yl} -phenol;
3- [5- (3,4-dichloro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (3,4-dichloro-benzyl) -amine;
4- [5- (3,4-dichloro-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (4-chloro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (4-chloro-benzyl) -amine;
4- [5- (4-Chloro-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (3,4-difluoro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (3,4-difluoro-benzyl) -amine;
4- [5- (3,4-dimethoxy-benzylamino) -pyridin-3-yl] -phenol;
3- {5-[(benzo [1,3] dioxol-5-ylmethyl) -amino] -pyridin-3-yl} -benzamide;
Benzo [1,3] dioxol-5-ylmethyl- [3,4 '] bipyridinyl-5-yl-amine;
4- {5-[(benzo [1,3] dioxol-5-ylmethyl) -amino] -pyridin-3-yl} -phenol;
4- [5- (3,4-difluoro-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -N- (2-hydroxy-ethyl) -benzamide;
3- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -benzamide;
3-[(5-benzo [1,3] dioxol-5-yl-pyridin-3-ylamino) -methyl] -phenol;
3-([3,4 '] bipyridinyl-5-ylaminomethyl) -phenol;
3-{[5- (4-hydroxymethyl-phenyl) -pyridin-3-ylamino] -methyl} -phenol;
N- {3- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -phenyl} -acetamide;
(5- (4′-hydroxy-phenyl) -pyridin-3-yl)-(3-hydroxy-benzyl) -amine;
3-{[5- (3-hydroxymethyl-phenyl) -pyridin-3-ylamino] -methyl} -phenol;
(5- (3′-hydroxy-phenyl) -pyridin-3-yl)-(3-hydroxy-benzyl) -amine;
3- {5-[(furan-3-ylmethyl) -amino] -pyridin-3-yl} -benzamide;
[3,4 '] bipyridinyl-5-yl-furan-3-ylmethyl-amine;
4- {5-[(furan-3-ylmethyl) -amino] -pyridin-3-yl} -phenol;
3- {5-[(pyridin-3-ylmethyl) -amino] -pyridin-3-yl} -benzamide;
[3,4 '] bipyridinyl-5-yl- (3-chloro-phenyl) -amine;
3- [5- (3-bromo-phenylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (3-bromo-phenyl) -amine;
[3,4 '] bipyridinyl-5-yl- (3-nitro-phenyl) -amine;
3-[(3′-chloro- [3,4 ′] bipyridinyl-5-ylamino) -methyl] -phenol;
3-[(5-quinolin-5-yl-pyridin-3-ylamino) -methyl] -phenol;
3-{[5- (1H-pyrazol-3-yl) -pyridin-3-ylamino] -methyl} -phenol;
3-[(5-isoquinolin-4-yl-pyridin-3-ylamino) methyl] -phenol;
4- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -benzamide;
3-{[5- (4-amino-phenyl) -pyridin-3-ylamino] -methyl} -phenol;
3-{[5- (1H-indol-5-yl) -pyridin-3-ylamino] -methyl} -phenol;
3-[(5′-methoxy- [3,3 ′] bipyridinyl-5-ylamino) -methyl] -phenol;
3-[(5-phenyl-pyridin-3-ylamino) -methyl] -phenol;
3-{[5- (3-amino-phenyl) -pyridin-3-ylamino] -methyl} -phenol;
5-{[5- (4-hydroxy-phenyl) -pyridin-3-ylamino] -methyl} -benzene-1,3-diol;
3- [5- (3,5-dihydroxy-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (3-chloro-benzyl) -amine;
3- [5- (3-chloro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (4-methoxy-benzyl) -amine;
4- [5- (4-methoxy-benzylamino) -pyridin-3-yl] -phenol;
5-{[5- (4-hydroxy-phenyl) -pyridin-3-ylamino] -methyl} -2-methoxy-phenol;
3- [5- (3-hydroxy-4-methoxy-benzylamino) -pyridin-3-yl] -benzamide;
3-([3,4 '] bipyridinyl-5-ylamino) -phenol;
4- [5- (3-hydroxy-phenylamino) -pyridin-3-yl] -phenol;
3- [5- (3-hydroxy-phenylamino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl-cyclohexylmethyl-amine;
4- [5- (cyclohexylmethyl-amino) -pyridin-3-yl] -phenol;
3- [5- (cyclohexylmethyl-amino) -pyridin-3-yl] -benzamide;
[3,4 '] bipyridinyl-5-yl- (4-chloro-3-fluoro-benzyl) -amine;
3- [5- (4-chloro-3-fluoro-benzylamino) -pyridin-3-yl] -benzamide;
[3,4 ']-bipyridinyl-5-yl- (3-trifluoromethoxy-benzyl) -amine;
4- [5- (3-trifluoromethoxy-benzylamino) -pyridin-3-yl] -phenol;
3- [5- (3-trifluoromethoxy-benzylamino) -pyridin-3-yl] -benzamide;
3- [5- (4-hydroxy-benzylamino) -pyridin-3-yl] -benzamide;
3- {5-[(pyrrolidin-2-ylmethyl) -amino] -pyridin-3-yl} -benzamide;
4- {5-[(pyrrolidin-2-ylmethyl) -amino] -pyridin-3-yl} -phenol;
[3,4 '] bipyridinyl-5-yl-pyrrolidin-2-ylmethyl-amine;
4- [5- (3-chloro-benzylamino) -pyridin-3-yl] -phenol;
N- {4- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -phenyl} -acetamide;
4- {5-[(3-hydroxy-benzyl) -methyl-amino] -pyridin-3-yl} -phenol;
3- [5- (3-hydroxy-benzylamino) -pyridin-3-yl] -N- (2-hydroxy-ethyl) -benzamide;
3- [5- (4-methoxy-benzylamino) -pyridin-3-yl] -benzamide;
N- [3,4 '] bipyridinyl-5-yl-2- (4-chloro-phenyl) -acetamide; and
[3,4 '] bipyridinyl-5-yl- (4-bromo-benzyl) -amine;
2. The compound of claim 1 selected from the group of
及びスキーム(b):
の少なくとも1つの工程又は一連の連続した工程を含む、請求項1から7までのいずれか一項に記載の化合物の作製方法。 Scheme (a) defined below :
And scheme (b):
A method for producing a compound according to any one of claims 1 to 7, comprising at least one step or a series of consecutive steps.
から成る群から選択される一般式で表されるコア化学構造(骨格)を有する、構造的に関連した一連の化合物を含む又はそれらの化合物から成る2つ以上の化合物の一群。 Formula ( I ) and Formula ( II ):
A group of two or more compounds comprising or consisting of a series of structurally related compounds having a core chemical structure (skeleton) represented by the general formula selected from the group consisting of:
及びスキーム(b):
の少なくとも1つの工程又は一連の連続した工程を含む、請求項10に記載の化合物の一群を作製する方法。 Scheme (a) defined below :
And scheme (b):
11. A method of making a group of compounds according to claim 10 comprising at least one step or a series of consecutive steps.
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GBGB0315494.5A GB0315494D0 (en) | 2003-07-02 | 2003-07-02 | Compounds which bind to the active site of protein kinase enzymes |
GB0328497A GB2403721A (en) | 2003-07-02 | 2003-12-09 | Compounds which bind to the active site of protein kinase enzymes |
PCT/GB2004/002849 WO2005003101A2 (en) | 2003-07-02 | 2004-07-01 | Pyrazine and pyridine derivatives as rho kinase inhibitors |
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2004
- 2004-07-01 EP EP04743195A patent/EP1644365A2/en not_active Withdrawn
- 2004-07-01 CA CA002530389A patent/CA2530389A1/en not_active Abandoned
- 2004-07-01 WO PCT/GB2004/002849 patent/WO2005003101A2/en active Application Filing
- 2004-07-01 JP JP2006518333A patent/JP2007516196A/en not_active Abandoned
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