RU2560153C2 - Триазолпиридиновые соединения, ингибирующие jak, и способы - Google Patents

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Publication number

RU2560153C2

RU2560153C2 RU2011101898/04A RU2011101898A RU2560153C2 RU 2560153 C2 RU2560153 C2 RU 2560153C2 RU 2011101898/04 A RU2011101898/04 A RU 2011101898/04A RU 2011101898 A RU2011101898 A RU 2011101898A RU 2560153 C2 RU2560153 C2 RU 2560153C2

Authority

RU

Russia

Prior art keywords

pyridin

triazolo

ylamino

benzamide

alkyl

Prior art date

2008-06-20

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• 238000000034 method Methods 0.000 title description 66
• 230000002401 inhibitory effect Effects 0.000 title description 10
• 150000008523 triazolopyridines Chemical class 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 191
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 52
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• -1 hydroxypiperidinyl Chemical group 0.000 claims description 231
• 229910052736 halogen Inorganic materials 0.000 claims description 70
• 150000002367 halogens Chemical group 0.000 claims description 70
• 125000000623 heterocyclic group Chemical group 0.000 claims description 58
• 125000001072 heteroaryl group Chemical group 0.000 claims description 46
• 229910052799 carbon Inorganic materials 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 17
• LJCJRRKKAKAKRV-UHFFFAOYSA-N (2-amino-2-methylpropyl) 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical group CC(C)(N)COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LJCJRRKKAKAKRV-UHFFFAOYSA-N 0.000 claims description 16
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
• 125000003386 piperidinyl group Chemical group 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000003277 amino group Chemical group 0.000 claims description 9
• 125000004193 piperazinyl group Chemical group 0.000 claims description 9
• 125000001425 triazolyl group Chemical group 0.000 claims description 9
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 8
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• KBXMXEMVZYHNLV-UHFFFAOYSA-N 4-[[8-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzoic acid Chemical compound COC1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(O)=O)=NN3C=CC=2)=C1 KBXMXEMVZYHNLV-UHFFFAOYSA-N 0.000 claims description 3
• KRZGYOQJCVKWHG-UHFFFAOYSA-N 5-[[8-(3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-3,3-dimethyl-2h-isoindol-1-one Chemical compound C1=C2C(C)(C)NC(=O)C2=CC=C1NC(=NN1C=CC=2)N=C1C=2C1=CC=CC(F)=C1 KRZGYOQJCVKWHG-UHFFFAOYSA-N 0.000 claims description 3
• JWGTVLHHDDDEOE-UHFFFAOYSA-N [4-[[8-(4-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]-morpholin-4-ylmethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=CN2C1=NC(NC=1C=CC(=CC=1)C(=O)N1CCOCC1)=N2 JWGTVLHHDDDEOE-UHFFFAOYSA-N 0.000 claims description 3
• NBEQFCFWVCNIBW-UHFFFAOYSA-N n-piperidin-4-yl-4-[[8-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzamide Chemical compound FC(F)(F)C1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(=O)NC4CCNCC4)=NN3C=CC=2)=C1 NBEQFCFWVCNIBW-UHFFFAOYSA-N 0.000 claims description 3
• DJHNYLFVTSTIID-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[4-[[8-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(=O)N4CC(N)C4)=NN3C=CC=2)=C1 DJHNYLFVTSTIID-UHFFFAOYSA-N 0.000 claims description 2
• YJOPFBSPTNCXKZ-UHFFFAOYSA-N (3-hydroxyazetidin-1-yl)-[4-[[8-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(=O)N4CC(O)C4)=NN3C=CC=2)=C1 YJOPFBSPTNCXKZ-UHFFFAOYSA-N 0.000 claims description 2
• OODMKBAMRMISRA-UHFFFAOYSA-N (3-methoxyazetidin-1-yl)-[4-[[8-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanone Chemical compound C1C(OC)CN1C(=O)C(C=C1)=CC=C1NC1=NN2C=CC=C(C=3C=C(C=CC=3)S(C)(=O)=O)C2=N1 OODMKBAMRMISRA-UHFFFAOYSA-N 0.000 claims description 2
• XTSNIGLSLDVBCU-UHFFFAOYSA-N 2-fluoro-4-[[8-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=CN2C1=NC(NC=1C=C(F)C(C(O)=O)=CC=1)=N2 XTSNIGLSLDVBCU-UHFFFAOYSA-N 0.000 claims description 2
• XFPNUCPCIFQUCT-OAQYLSRUSA-N 4-[2-[4-[(3r)-3-hydroxypiperidine-1-carbonyl]anilino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl]benzonitrile Chemical compound C1[C@H](O)CCCN1C(=O)C(C=C1)=CC=C1NC1=NN2C=CC=C(C=3C=CC(=CC=3)C#N)C2=N1 XFPNUCPCIFQUCT-OAQYLSRUSA-N 0.000 claims description 2
• CZNOGVOOINSHCV-HXUWFJFHSA-N 4-[2-[4-[(3r)-3-hydroxypyrrolidine-1-carbonyl]anilino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl]benzonitrile Chemical compound C1[C@H](O)CCN1C(=O)C(C=C1)=CC=C1NC1=NN2C=CC=C(C=3C=CC(=CC=3)C#N)C2=N1 CZNOGVOOINSHCV-HXUWFJFHSA-N 0.000 claims description 2
• XFPNUCPCIFQUCT-NRFANRHFSA-N 4-[2-[4-[(3s)-3-hydroxypiperidine-1-carbonyl]anilino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl]benzonitrile Chemical compound C1[C@@H](O)CCCN1C(=O)C(C=C1)=CC=C1NC1=NN2C=CC=C(C=3C=CC(=CC=3)C#N)C2=N1 XFPNUCPCIFQUCT-NRFANRHFSA-N 0.000 claims description 2
• CZNOGVOOINSHCV-FQEVSTJZSA-N 4-[2-[4-[(3s)-3-hydroxypyrrolidine-1-carbonyl]anilino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl]benzonitrile Chemical compound C1[C@@H](O)CCN1C(=O)C(C=C1)=CC=C1NC1=NN2C=CC=C(C=3C=CC(=CC=3)C#N)C2=N1 CZNOGVOOINSHCV-FQEVSTJZSA-N 0.000 claims description 2
• PZFPZRGYDDDJEA-UHFFFAOYSA-N 4-[[8-(3-fluorophenyl)-7-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n,n-dimethylbenzamide Chemical compound N1=C2C(C=3C=C(F)C=CC=3)=C(OC)C=CN2N=C1NC1=CC=C(C(=O)N(C)C)C=C1 PZFPZRGYDDDJEA-UHFFFAOYSA-N 0.000 claims description 2
• WFNXIMGUOWUFLJ-UHFFFAOYSA-N 4-[[8-(3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC1=NN2C=CC=C(C=3C=C(F)C=CC=3)C2=N1 WFNXIMGUOWUFLJ-UHFFFAOYSA-N 0.000 claims description 2
• GNULFOXWEASYCL-UHFFFAOYSA-N 4-[[8-(4-cyanophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-2-(trifluoromethyl)benzoic acid Chemical compound C1=C(C(F)(F)F)C(C(=O)O)=CC=C1NC1=NN2C=CC=C(C=3C=CC(=CC=3)C#N)C2=N1 GNULFOXWEASYCL-UHFFFAOYSA-N 0.000 claims description 2
• SAOJVKXKZODAIL-UHFFFAOYSA-N 4-[[8-(4-methoxy-2-methylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzoic acid Chemical compound CC1=CC(OC)=CC=C1C1=CC=CN2C1=NC(NC=1C=CC(=CC=1)C(O)=O)=N2 SAOJVKXKZODAIL-UHFFFAOYSA-N 0.000 claims description 2
• KIKJMFOEWGYBPD-UHFFFAOYSA-N 4-[[8-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-2-(trifluoromethyl)benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=CN2C1=NC(NC=1C=C(C(C(O)=O)=CC=1)C(F)(F)F)=N2 KIKJMFOEWGYBPD-UHFFFAOYSA-N 0.000 claims description 2
• MKUDJHMMRZGUJI-UHFFFAOYSA-N 4-[[8-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]-n-(piperidin-4-ylmethyl)benzamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CN2C1=NC(NC=1C=CC(=CC=1)C(=O)NCC1CCNCC1)=N2 MKUDJHMMRZGUJI-UHFFFAOYSA-N 0.000 claims description 2
• YZUKESPJWCKIQZ-UHFFFAOYSA-N 4-[[8-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=CN2C1=NC(NC=1C=CC(=CC=1)C(O)=O)=N2 YZUKESPJWCKIQZ-UHFFFAOYSA-N 0.000 claims description 2
• XRAORVLEWHZKKI-UHFFFAOYSA-N 4-[[8-[3-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NN2C=CC=C(C=3C=C(OC(F)(F)F)C=CC=3)C2=N1 XRAORVLEWHZKKI-UHFFFAOYSA-N 0.000 claims description 2
• MUGCQSVQUJTTOP-UHFFFAOYSA-N 8-(2-fluorophenyl)-n-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound FC1=CC=CC=C1C1=CC=CN2C1=NC(NC=1C=CC=CC=1)=N2 MUGCQSVQUJTTOP-UHFFFAOYSA-N 0.000 claims description 2
• QHYAVQXSXJQSGC-UHFFFAOYSA-N 8-(3-fluorophenyl)-n-[4-(1h-1,2,4-triazol-5-yl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound FC1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C=4NC=NN=4)=NN3C=CC=2)=C1 QHYAVQXSXJQSGC-UHFFFAOYSA-N 0.000 claims description 2
• HSPBUDKSMXSHAU-UHFFFAOYSA-N 8-(3-methoxyphenyl)-n-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound COC1=CC=CC(C=2C3=NC(NC=4C=CC=CC=4)=NN3C=CC=2)=C1 HSPBUDKSMXSHAU-UHFFFAOYSA-N 0.000 claims description 2
• PELYMQXDDQNSQK-UHFFFAOYSA-N 8-(3-methoxyphenyl)-n-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound COC1=CC=CC(C=2C3=NC(NC=4C=CN=CC=4)=NN3C=CC=2)=C1 PELYMQXDDQNSQK-UHFFFAOYSA-N 0.000 claims description 2
• GXMFHCJTFARDCA-HXUWFJFHSA-N [(3r)-3-hydroxypiperidin-1-yl]-[4-[[8-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(=O)N4C[C@H](O)CCC4)=NN3C=CC=2)=C1 GXMFHCJTFARDCA-HXUWFJFHSA-N 0.000 claims description 2
• XURCAQPEBOGMLV-LJQANCHMSA-N [(3r)-3-hydroxypyrrolidin-1-yl]-[4-[[8-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(=O)N4C[C@H](O)CC4)=NN3C=CC=2)=C1 XURCAQPEBOGMLV-LJQANCHMSA-N 0.000 claims description 2
• GXMFHCJTFARDCA-FQEVSTJZSA-N [(3s)-3-hydroxypiperidin-1-yl]-[4-[[8-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(=O)N4C[C@@H](O)CCC4)=NN3C=CC=2)=C1 GXMFHCJTFARDCA-FQEVSTJZSA-N 0.000 claims description 2
• XURCAQPEBOGMLV-IBGZPJMESA-N [(3s)-3-hydroxypyrrolidin-1-yl]-[4-[[8-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(=O)N4C[C@@H](O)CC4)=NN3C=CC=2)=C1 XURCAQPEBOGMLV-IBGZPJMESA-N 0.000 claims description 2
• KFCGMMGLXZSVRY-UHFFFAOYSA-N [4-[[8-(3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1NC1=NN2C=CC=C(C=3C=C(F)C=CC=3)C2=N1 KFCGMMGLXZSVRY-UHFFFAOYSA-N 0.000 claims description 2
• BLXQGXBZPVDAJY-UHFFFAOYSA-N [4-[[8-(4-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC=CN2C1=NC(NC=1C=CC(=CC=1)C(=O)N1CCCC1)=N2 BLXQGXBZPVDAJY-UHFFFAOYSA-N 0.000 claims description 2
• TXZQSJBQJQPSHB-UHFFFAOYSA-N azetidin-1-yl-[4-[[8-(3-methylsulfonylphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]phenyl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C=2C3=NC(NC=4C=CC(=CC=4)C(=O)N4CCC4)=NN3C=CC=2)=C1 TXZQSJBQJQPSHB-UHFFFAOYSA-N 0.000 claims description 2
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