JP2013517264A5 - - Google Patents
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- Publication number
- JP2013517264A5 JP2013517264A5 JP2012548527A JP2012548527A JP2013517264A5 JP 2013517264 A5 JP2013517264 A5 JP 2013517264A5 JP 2012548527 A JP2012548527 A JP 2012548527A JP 2012548527 A JP2012548527 A JP 2012548527A JP 2013517264 A5 JP2013517264 A5 JP 2013517264A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- phenyl
- amine
- methylsulfonyl
- amino
- 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.)
- Granted
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- -1 carbonylphenyl Chemical group 0.000 claims 42
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 18
- 229940124530 sulfonamide Drugs 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 7
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 6
- 125000005605 benzo group Chemical group 0.000 claims 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 5
- 150000003927 aminopyridines Chemical class 0.000 claims 4
- NKISFEQKTBMSTH-UHFFFAOYSA-N 3,5-bis(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 NKISFEQKTBMSTH-UHFFFAOYSA-N 0.000 claims 3
- ADECQYTURGAKRL-UHFFFAOYSA-N 3,5-bis(6-methoxypyridin-3-yl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CN=C(N)C(C=2C=NC(OC)=CC=2)=C1 ADECQYTURGAKRL-UHFFFAOYSA-N 0.000 claims 3
- SUDVYWXIJNQDSM-UHFFFAOYSA-N 3-(2-methoxypyridin-3-yl)-5-(1-methylindazol-6-yl)pyridin-2-amine Chemical compound COC1=NC=CC=C1C1=CC(C=2C=C3N(C)N=CC3=CC=2)=CN=C1N SUDVYWXIJNQDSM-UHFFFAOYSA-N 0.000 claims 3
- XHOUEKXTVUWQCB-UHFFFAOYSA-N 3-(2-methoxypyrimidin-5-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=NC(OC)=NC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N XHOUEKXTVUWQCB-UHFFFAOYSA-N 0.000 claims 3
- ZJTXTUXHHBDBKQ-UHFFFAOYSA-N 3-(2-methyl-1,3-benzothiazol-5-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C=1C=C2SC(C)=NC2=CC=1C(C(=NC=1)N)=CC=1C1=CC=C(S(C)(=O)=O)C=C1 ZJTXTUXHHBDBKQ-UHFFFAOYSA-N 0.000 claims 3
- VNWFKIQORFKHQR-UHFFFAOYSA-N 3-(3-methoxypyridin-4-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound COC1=CN=CC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N VNWFKIQORFKHQR-UHFFFAOYSA-N 0.000 claims 3
- HZIOHEZNLQRWSI-UHFFFAOYSA-N 3-(4-methylphenyl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=CC(C)=CC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N HZIOHEZNLQRWSI-UHFFFAOYSA-N 0.000 claims 3
- LFQYCOBOTAQALI-UHFFFAOYSA-N 3-(5-chloro-6-methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=C(Cl)C(OC)=NC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N LFQYCOBOTAQALI-UHFFFAOYSA-N 0.000 claims 3
- QUSMOXHAFLWLFX-UHFFFAOYSA-N 3-(5-methylpyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound CC1=CN=CC(C=2C(=NC=C(C=2)C=2C=CC(=CC=2)S(C)(=O)=O)N)=C1 QUSMOXHAFLWLFX-UHFFFAOYSA-N 0.000 claims 3
- YUQXMDIJCYMKBB-UHFFFAOYSA-N 3-(6-fluoropyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC(F)=CC=2)=C1 YUQXMDIJCYMKBB-UHFFFAOYSA-N 0.000 claims 3
- KMUZKBAYJWGYGC-UHFFFAOYSA-N 3-(6-methoxy-2-methylpyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound CC1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N KMUZKBAYJWGYGC-UHFFFAOYSA-N 0.000 claims 3
- ONZDDVOSVHSCHJ-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-(3-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=C(C=CC=2)S(C)(=O)=O)=CN=C1N ONZDDVOSVHSCHJ-UHFFFAOYSA-N 0.000 claims 3
- MPUUTGILUJDKKP-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N MPUUTGILUJDKKP-UHFFFAOYSA-N 0.000 claims 3
- GXOKGTYDFIBJNC-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-(4-pyrazol-1-ylphenyl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)N2N=CC=C2)=CN=C1N GXOKGTYDFIBJNC-UHFFFAOYSA-N 0.000 claims 3
- JEXSUGIEMWLKAU-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-(6-morpholin-4-ylpyridin-3-yl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=NC(=CC=2)N2CCOCC2)=CN=C1N JEXSUGIEMWLKAU-UHFFFAOYSA-N 0.000 claims 3
- VQEDNCKIUDHQGN-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C=2OC(C)=NN=2)=CN=C1N VQEDNCKIUDHQGN-UHFFFAOYSA-N 0.000 claims 3
- KBNXAJBSRRGHSK-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-[4-methylsulfonyl-2-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C(=CC(=CC=2)S(C)(=O)=O)C(F)(F)F)=CN=C1N KBNXAJBSRRGHSK-UHFFFAOYSA-N 0.000 claims 3
- LPEJLBJOQQSAGF-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-quinolin-6-ylpyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=C3C=CC=NC3=CC=2)=CN=C1N LPEJLBJOQQSAGF-UHFFFAOYSA-N 0.000 claims 3
- MEZBSZIOMPUBDQ-UHFFFAOYSA-N 3-(6-methylpyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=NC(C)=CC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N MEZBSZIOMPUBDQ-UHFFFAOYSA-N 0.000 claims 3
- AZGVCLHFJHUBLQ-UHFFFAOYSA-N 3-(furan-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C2=COC=C2)=C1 AZGVCLHFJHUBLQ-UHFFFAOYSA-N 0.000 claims 3
- IFAYNCVEMRFBJX-UHFFFAOYSA-N 3-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]benzonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=C(C=CC=2)C#N)=C1 IFAYNCVEMRFBJX-UHFFFAOYSA-N 0.000 claims 3
- UDWXFSPADQHCNB-UHFFFAOYSA-N 3-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]phenol Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=C(O)C=CC=2)=C1 UDWXFSPADQHCNB-UHFFFAOYSA-N 0.000 claims 3
- NRSYMHKUTBGODJ-UHFFFAOYSA-N 3-[2-chloro-4-(trifluoromethyl)phenyl]-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NRSYMHKUTBGODJ-UHFFFAOYSA-N 0.000 claims 3
- DAYYOTAJVCNIJK-UHFFFAOYSA-N 3-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound O1C(C)=NN=C1C1=CC=C(C=2C(=NC=C(C=2)C=2C=CC(=CC=2)S(C)(=O)=O)N)C=C1 DAYYOTAJVCNIJK-UHFFFAOYSA-N 0.000 claims 3
- NGCTYPIERXMDFK-UHFFFAOYSA-N 3-isoquinolin-5-yl-5-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C3=CC=NC=C3C=CC=2)=C1 NGCTYPIERXMDFK-UHFFFAOYSA-N 0.000 claims 3
- BPHUMAUSBOVDPO-UHFFFAOYSA-N 4-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2C(=NC=C(C=2)C=2C=CC(=CC=2)S(C)(=O)=O)N)=C1 BPHUMAUSBOVDPO-UHFFFAOYSA-N 0.000 claims 3
- SQICBTMJLWNRFZ-UHFFFAOYSA-N 4-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N SQICBTMJLWNRFZ-UHFFFAOYSA-N 0.000 claims 3
- ROULPWBIPBUFHM-UHFFFAOYSA-N 4-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]benzamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(=CC=2)C(N)=O)=C1 ROULPWBIPBUFHM-UHFFFAOYSA-N 0.000 claims 3
- CZEGCQZTDUKTJP-UHFFFAOYSA-N 4-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]benzonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(=CC=2)C#N)=C1 CZEGCQZTDUKTJP-UHFFFAOYSA-N 0.000 claims 3
- XOBFJLXKNALFLR-UHFFFAOYSA-N 4-[2-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]-2-methoxyphenol Chemical compound C1=NC(OC)=CC=C1C1=CN=C(N)C(C=2C=C(OC)C(O)=CC=2)=C1 XOBFJLXKNALFLR-UHFFFAOYSA-N 0.000 claims 3
- YOGVDOXYUFKFSD-UHFFFAOYSA-N 4-[2-amino-5-[4-(morpholine-4-carbonyl)phenyl]pyridin-3-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)N2CCOCC2)=CN=C1N YOGVDOXYUFKFSD-UHFFFAOYSA-N 0.000 claims 3
- PWSITNMVZZIHAY-UHFFFAOYSA-N 4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]-n,n-dimethylbenzamide Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)N(C)C)=CN=C1N PWSITNMVZZIHAY-UHFFFAOYSA-N 0.000 claims 3
- WEMIDIZCMUDJIR-UHFFFAOYSA-N 4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]-n-(3-hydroxypropyl)benzamide Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)NCCCO)=CN=C1N WEMIDIZCMUDJIR-UHFFFAOYSA-N 0.000 claims 3
- KYGYGFVXGRSHPF-UHFFFAOYSA-N 4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]-n-cyclopropylbenzamide Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)NC2CC2)=CN=C1N KYGYGFVXGRSHPF-UHFFFAOYSA-N 0.000 claims 3
- PTCFIURDTNELCW-UHFFFAOYSA-N 4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN=C(N)C(C=2C=NC(OC)=CC=2)=C1 PTCFIURDTNELCW-UHFFFAOYSA-N 0.000 claims 3
- VFLWDRICFHCSKI-UHFFFAOYSA-N 4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]benzoic acid Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(O)=O)=CN=C1N VFLWDRICFHCSKI-UHFFFAOYSA-N 0.000 claims 3
- USYVDEUJHKKOLX-UHFFFAOYSA-N 4-[6-amino-5-[4-(4-methylpiperazin-1-yl)phenyl]pyridin-3-yl]-2,6-dimethylphenol Chemical compound C1CN(C)CCN1C1=CC=C(C=2C(=NC=C(C=2)C=2C=C(C)C(O)=C(C)C=2)N)C=C1 USYVDEUJHKKOLX-UHFFFAOYSA-N 0.000 claims 3
- JJIBPOFDJWBISC-UHFFFAOYSA-N 4-[6-amino-5-[4-(4-methylpiperazin-1-yl)phenyl]pyridin-3-yl]phenol Chemical compound C1CN(C)CCN1C1=CC=C(C=2C(=NC=C(C=2)C=2C=CC(O)=CC=2)N)C=C1 JJIBPOFDJWBISC-UHFFFAOYSA-N 0.000 claims 3
- ODQZZWWRJFGDAH-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-(4-morpholin-4-ylphenyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(=CC=2)N2CCOCC2)=C1 ODQZZWWRJFGDAH-UHFFFAOYSA-N 0.000 claims 3
- XDLRIGFEAQZOOK-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-(4-pyrazol-1-ylphenyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(=CC=2)N2N=CC=C2)=C1 XDLRIGFEAQZOOK-UHFFFAOYSA-N 0.000 claims 3
- NDGSTJVONFECBI-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-(6-methylsulfonylpyridin-3-yl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC(=CC=2)S(C)(=O)=O)=C1 NDGSTJVONFECBI-UHFFFAOYSA-N 0.000 claims 3
- SPBYUGORRCXRPE-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-(6-morpholin-4-ylpyridin-3-yl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC(=CC=2)N2CCOCC2)=C1 SPBYUGORRCXRPE-UHFFFAOYSA-N 0.000 claims 3
- IUKLRMWZRDHRQA-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-(6-pyrrolidin-1-ylpyridin-3-yl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC(=CC=2)N2CCCC2)=C1 IUKLRMWZRDHRQA-UHFFFAOYSA-N 0.000 claims 3
- IEJRGOMPDLFNEO-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-[2-(trifluoromethyl)pyridin-4-yl]pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=C(N=CC=2)C(F)(F)F)=C1 IEJRGOMPDLFNEO-UHFFFAOYSA-N 0.000 claims 3
- RAFGFIDLUQSHFE-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-[3-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=C(OC(F)(F)F)C=CC=2)=C1 RAFGFIDLUQSHFE-UHFFFAOYSA-N 0.000 claims 3
- NJNPOYRKVLVZCM-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-[3-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=C(C=CC=2)C(F)(F)F)=C1 NJNPOYRKVLVZCM-UHFFFAOYSA-N 0.000 claims 3
- GKGAOGIKLVBTNP-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(OCCN3CCCC3)=CC=2)=C1 GKGAOGIKLVBTNP-UHFFFAOYSA-N 0.000 claims 3
- NFPBGUXCNXUNAQ-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-[4-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(OC(F)(F)F)=CC=2)=C1 NFPBGUXCNXUNAQ-UHFFFAOYSA-N 0.000 claims 3
- RTJQABCNNLMCJF-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-[6-(trifluoromethyl)pyridin-3-yl]pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC(=CC=2)C(F)(F)F)=C1 RTJQABCNNLMCJF-UHFFFAOYSA-N 0.000 claims 3
- ISEIWXOWUTYATO-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-pyridin-3-ylpyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC=CC=2)=C1 ISEIWXOWUTYATO-UHFFFAOYSA-N 0.000 claims 3
- VKAMTTXMAWVBAV-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-pyrimidin-5-ylpyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC=NC=2)=C1 VKAMTTXMAWVBAV-UHFFFAOYSA-N 0.000 claims 3
- AMZOLWPYOZODBE-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-quinolin-6-ylpyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=C3C=CC=NC3=CC=2)=C1 AMZOLWPYOZODBE-UHFFFAOYSA-N 0.000 claims 3
- ISFQOUBZTDIQBI-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-quinoxalin-6-ylpyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=C3N=CC=NC3=CC=2)=C1 ISFQOUBZTDIQBI-UHFFFAOYSA-N 0.000 claims 3
- SVSRCMVFWSXMOD-UHFFFAOYSA-N 5-(6-methoxypyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CN=C(N)C(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 SVSRCMVFWSXMOD-UHFFFAOYSA-N 0.000 claims 3
- XLBVMICOXNAAIE-UHFFFAOYSA-N 5-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC(N)=NC=2)=C1 XLBVMICOXNAAIE-UHFFFAOYSA-N 0.000 claims 3
- XDYQPLALTDYWPQ-UHFFFAOYSA-N O1CCN(CC1)C=O.NC1=NC=C(C=C1C1=CC=C(C(=O)NCCO)C=C1)C Chemical compound O1CCN(CC1)C=O.NC1=NC=C(C=C1C1=CC=C(C(=O)NCCO)C=C1)C XDYQPLALTDYWPQ-UHFFFAOYSA-N 0.000 claims 3
- AIQVVTYFNCZUGZ-UHFFFAOYSA-N [4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)N2CCOCC2)=CN=C1N AIQVVTYFNCZUGZ-UHFFFAOYSA-N 0.000 claims 3
- RABQOBJRYDTPBH-UHFFFAOYSA-N [4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]phenyl]methanol Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(CO)=CC=2)=CN=C1N RABQOBJRYDTPBH-UHFFFAOYSA-N 0.000 claims 3
- SOEIQDGWTONCHH-UHFFFAOYSA-N [4-[6-amino-5-[4-(trifluoromethyl)phenyl]pyridin-3-yl]phenyl]-morpholin-4-ylmethanone Chemical compound NC1=NC=C(C=2C=CC(=CC=2)C(=O)N2CCOCC2)C=C1C1=CC=C(C(F)(F)F)C=C1 SOEIQDGWTONCHH-UHFFFAOYSA-N 0.000 claims 3
- RJOPAWYXTPAMOM-UHFFFAOYSA-N [5-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]pyridin-2-yl]methanol Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=NC(CO)=CC=2)=C1 RJOPAWYXTPAMOM-UHFFFAOYSA-N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 201000004792 malaria Diseases 0.000 claims 3
- UTLIOLYNFZBUGG-UHFFFAOYSA-N n-[5-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=CN=C1N UTLIOLYNFZBUGG-UHFFFAOYSA-N 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- BPVPQYPYOLLZIV-UHFFFAOYSA-N 4-(2-amino-5-bromopyridin-3-yl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2C(=NC=C(Br)C=2)N)=C1 BPVPQYPYOLLZIV-UHFFFAOYSA-N 0.000 claims 2
- FXKMJFLSQZWQSB-UHFFFAOYSA-N 4-(2-amino-5-bromopyridin-3-yl)-n-(2-hydroxyethyl)benzamide Chemical compound NC1=NC=C(Br)C=C1C1=CC=C(C(=O)NCCO)C=C1 FXKMJFLSQZWQSB-UHFFFAOYSA-N 0.000 claims 2
- AFQDPNHISVHDMI-UHFFFAOYSA-N 5-(3-fluoro-4-methylsulfonylphenyl)-3-(6-methoxypyridin-3-yl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=C(F)C(=CC=2)S(C)(=O)=O)=CN=C1N AFQDPNHISVHDMI-UHFFFAOYSA-N 0.000 claims 2
- XOWVXIRCAYYBIV-UHFFFAOYSA-N 5-(4-methylsulfonylphenyl)-3-[4-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(=CC=2)C(F)(F)F)=C1 XOWVXIRCAYYBIV-UHFFFAOYSA-N 0.000 claims 2
- GQAOHPCZUKXASH-UHFFFAOYSA-N 5-bromo-3-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(Br)=CN=C1N GQAOHPCZUKXASH-UHFFFAOYSA-N 0.000 claims 2
- AHMRAGFZISBWBY-UHFFFAOYSA-N 5-bromo-3-(6-methoxypyridin-3-yl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(Br)=CN=C1N AHMRAGFZISBWBY-UHFFFAOYSA-N 0.000 claims 2
- AHZUOZWQNKBDEP-UHFFFAOYSA-N 5-bromo-3-(6-methylpyridin-3-yl)pyridin-2-amine Chemical compound C1=NC(C)=CC=C1C1=CC(Br)=CN=C1N AHZUOZWQNKBDEP-UHFFFAOYSA-N 0.000 claims 2
- RFHUASLKEPCJPR-UHFFFAOYSA-N 5-bromo-3-[4-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound NC1=NC=C(Br)C=C1C1=CC=C(C(F)(F)F)C=C1 RFHUASLKEPCJPR-UHFFFAOYSA-N 0.000 claims 2
- ITCPTFGMRLQZMM-UHFFFAOYSA-N 5-bromo-3-pyrimidin-5-ylpyridin-2-amine Chemical compound NC1=NC=C(Br)C=C1C1=CN=CN=C1 ITCPTFGMRLQZMM-UHFFFAOYSA-N 0.000 claims 2
- OXIDYTIVZKKPRS-UHFFFAOYSA-N [4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)N2CCN(C)CC2)=CN=C1N OXIDYTIVZKKPRS-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 150000003222 pyridines Chemical class 0.000 claims 2
- ACSLSCSSKUWVAV-UHFFFAOYSA-N 3-(2-amino-5-bromopyridin-3-yl)phenol Chemical compound NC1=NC=C(Br)C=C1C1=CC=CC(O)=C1 ACSLSCSSKUWVAV-UHFFFAOYSA-N 0.000 claims 1
- XACWVYOYIIFUOZ-UHFFFAOYSA-N 4-(2-amino-5-bromopyridin-3-yl)phenol Chemical compound NC1=NC=C(Br)C=C1C1=CC=C(O)C=C1 XACWVYOYIIFUOZ-UHFFFAOYSA-N 0.000 claims 1
- GHGKKGUNIGFCES-UHFFFAOYSA-N 4-[2-amino-5-(4-methylsulfonylphenyl)pyridin-3-yl]phenol Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C(N)C(C=2C=CC(O)=CC=2)=C1 GHGKKGUNIGFCES-UHFFFAOYSA-N 0.000 claims 1
- ZJMGJSJSWDLDNA-UHFFFAOYSA-N 5-bromo-3-[4-(4-methylpiperazin-1-yl)phenyl]pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=C(C=2C(=NC=C(Br)C=2)N)C=C1 ZJMGJSJSWDLDNA-UHFFFAOYSA-N 0.000 claims 1
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical class NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 claims 1
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| Publication number | Priority date | Publication date | Assignee | Title |
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| PL3354650T3 (pl) | 2008-12-19 | 2022-06-13 | Vertex Pharmaceuticals Incorporated | Związki przydatne jako inhibitory kinazy atr |
| JP5836367B2 (ja) | 2010-05-12 | 2015-12-24 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| JP2013526540A (ja) | 2010-05-12 | 2013-06-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| US9096584B2 (en) * | 2010-05-12 | 2015-08-04 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| KR20140014205A (ko) * | 2011-03-04 | 2014-02-05 | 렉시컨 파마슈티컬스 인코퍼레이티드 | Mst1 키나제 억제제 및 그의 사용 방법 |
| RU2018147217A (ru) | 2011-09-30 | 2019-01-18 | Вертекс Фармасьютикалз Инкорпорейтед | Способы получения соединений, которые можно использовать в качестве ингибиторов киназы atr |
| AU2012315384B2 (en) | 2011-09-30 | 2017-08-10 | Vertex Pharmaceuticals Incorporated | Treating pancreatic cancer and non-small cell lung cancer with ATR inhibitors |
| ME02535B (me) * | 2012-02-17 | 2017-02-20 | Univ Cape Town | Antimalarijski agensi |
| CN104582795B (zh) | 2012-04-05 | 2018-04-20 | 沃泰克斯药物股份有限公司 | 可用作atr激酶抑制剂的化合物及其组合疗法 |
| DK2904406T3 (en) | 2012-10-04 | 2018-06-18 | Vertex Pharma | METHOD OF DETERMINING THE ATR INHIBITION, INCREASED DNA DAMAGE |
| KR20210125575A (ko) | 2013-03-15 | 2021-10-18 | 코르테바 애그리사이언스 엘엘씨 | 4-아미노-6-(헤테로시클릭)피콜리네이트 및 6-아미노-2-(헤테로시클릭)피리미딘-4-카르복실레이트 및 제초제로서의 그의 용도 |
| EP2970186B1 (en) * | 2013-03-15 | 2020-06-10 | Dow AgroSciences LLC | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic) pyrimidine-4-carboxylates and their use as herbicides |
| AU2014391610B2 (en) | 2014-04-24 | 2018-01-25 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| KR20160145780A (ko) * | 2014-04-24 | 2016-12-20 | 노파르티스 아게 | 포스파티딜이노시톨 3-키나제 억제제로서의 아미노 피리딘 유도체 |
| CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| CN107531683B (zh) * | 2015-03-20 | 2022-05-13 | 豪夫迈·罗氏有限公司 | Usp7抑制剂化合物及使用方法 |
| EP3118198A1 (en) * | 2015-07-13 | 2017-01-18 | MMV Medicines for Malaria Venture | Anti-malarial agents |
| US11464774B2 (en) | 2015-09-30 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
| WO2017067881A1 (en) * | 2015-10-19 | 2017-04-27 | Glaxosmithkline Intellectual Property Development Limited | Pyrazine compounds for use in the treatment of parasitic protozoal infections |
| GB201603104D0 (en) * | 2016-02-23 | 2016-04-06 | Ucb Biopharma Sprl | Therapeutic agents |
| EP3254679A1 (de) | 2016-06-09 | 2017-12-13 | Christian-Albrechts-Universität zu Kiel | Wirkstoffe gegen protozoen und bakterien |
| BR112020012651A2 (pt) * | 2017-12-22 | 2020-12-01 | Ravenna Pharmaceuticals, Inc. | compostos derivados de aril-bipiridina amina como inibidores da fosfatidilinositol fosfato quinase, composição farmacêutica compreendendo os mesmos e usos terapêuticos dos ditos compostos |
| CR20200464A (es) | 2018-03-08 | 2021-04-14 | Incyte Corp | Compuestos diólicos de aminopirazina como inhibidores de pi3k-y |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| EP3842100A1 (en) * | 2019-12-24 | 2021-06-30 | The Board Of Regents Of The University Of Texas System | Anti-malarial agents |
| EP4568970A1 (en) | 2022-08-09 | 2025-06-18 | Merck Patent GmbH | Furo pyrimidine derivates |
| WO2024033280A1 (en) | 2022-08-09 | 2024-02-15 | Merck Patent Gmbh | Furopyridin and furopyrimidin, inhibitors of pi4k, for use in the treatment of parasite infection and malaria |
| EP4574143A1 (en) | 2023-12-21 | 2025-06-25 | Universität Regensburg | Inhibitors of plasmodia remodeling enzymes |
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| KR100574350B1 (ko) | 2004-08-31 | 2006-04-27 | 한국화학연구원 | 2-아미노피리딘 유도체의 제조방법 |
| EP1924558B1 (en) | 2005-09-12 | 2010-01-13 | Council Of Scientific And Industrial Research | An antimalarial baylis-hillman adducts and a process for the preparation thereof |
| EP1900727A1 (en) * | 2006-08-30 | 2008-03-19 | Cellzome Ag | Aminopyridine derivatives as kinase inhibitors |
| CN101555248B (zh) | 2009-05-22 | 2011-06-22 | 北京欧凯纳斯科技有限公司 | 一种多取代1,5-萘啶化合物的制备方法 |
-
2011
- 2011-01-17 HR HRP20151143TT patent/HRP20151143T1/hr unknown
- 2011-01-17 HU HUE11704673A patent/HUE027946T2/en unknown
- 2011-01-17 RS RS20150696A patent/RS54339B1/sr unknown
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- 2011-01-17 JP JP2012548527A patent/JP5735986B2/ja not_active Expired - Fee Related
- 2011-01-17 SI SI201130636T patent/SI2526090T1/sl unknown
- 2011-01-17 PT PT117046730T patent/PT2526090E/pt unknown
- 2011-01-17 PL PL11704673T patent/PL2526090T3/pl unknown
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- 2011-01-17 US US13/522,775 patent/US9024033B2/en active Active
- 2011-01-17 ES ES11704673.0T patent/ES2551875T3/es active Active
- 2011-01-17 WO PCT/IB2011/050192 patent/WO2011086531A2/en not_active Ceased
-
2015
- 2015-11-26 SM SM201500291T patent/SMT201500291B/it unknown
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