BR112012017713A2 - Aminopiridina, formulação farmacêutica, processo para a preparação de um derivado de aminopiridina, intermediário, e, uso de uma aminopiridina ou de uma formulação farmacêutica - Google Patents
Aminopiridina, formulação farmacêutica, processo para a preparação de um derivado de aminopiridina, intermediário, e, uso de uma aminopiridina ou de uma formulação farmacêutica Download PDFInfo
- Publication number
- BR112012017713A2 BR112012017713A2 BR112012017713-3A BR112012017713A BR112012017713A2 BR 112012017713 A2 BR112012017713 A2 BR 112012017713A2 BR 112012017713 A BR112012017713 A BR 112012017713A BR 112012017713 A2 BR112012017713 A2 BR 112012017713A2
- Authority
- BR
- Brazil
- Prior art keywords
- pyridin
- phenyl
- amine
- amino
- methylsulfonyl
- Prior art date
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- 150000003927 aminopyridines Chemical class 0.000 title claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 7
- 201000004792 malaria Diseases 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- -1 sulfonyl phenyl Chemical group 0.000 claims description 36
- 239000003430 antimalarial agent Substances 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 9
- 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
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- 125000005605 benzo group Chemical group 0.000 claims 6
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 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
- 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
- UGPALDTVOPTCMY-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-1-methyl-5-phenyl-2H-pyridin-2-amine Chemical compound CN1C(C(=CC(=C1)C1=CC=CC=C1)C=1C=CC(=NC=1)OC)N UGPALDTVOPTCMY-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
- VPJGWPAURWAGNA-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-(4-morpholin-4-ylphenyl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)N2CCOCC2)=CN=C1N VPJGWPAURWAGNA-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
- YLGJFXMAIFUMLS-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-5-phenylpyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC=CC=2)=CN=C1N YLGJFXMAIFUMLS-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
- WGEPNHZGKKWHID-UHFFFAOYSA-N 4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)NCCN2CCOCC2)=CN=C1N WGEPNHZGKKWHID-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
- 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
- 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
- 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
- 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 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
- 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
- 150000001412 amines Chemical class 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- HKVHUQGTEFYHIM-UHFFFAOYSA-N n-[4-(2-amino-5-methylpyridin-3-yl)benzoyl]-n-(2-hydroxyethyl)morpholine-4-carboxamide Chemical compound CC1=CN=C(N)C(C=2C=CC(=CC=2)C(=O)N(CCO)C(=O)N2CCOCC2)=C1 HKVHUQGTEFYHIM-UHFFFAOYSA-N 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
- 238000011282 treatment Methods 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 2
- 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
- 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 2
- 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 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
- 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 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
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical class NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 claims 2
- 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 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
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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
- PMYWJGIXWJWPFZ-UHFFFAOYSA-N 4-[6-amino-5-(6-methoxypyridin-3-yl)pyridin-3-yl]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=NC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)NCCN2CCCC2)=CN=C1N PMYWJGIXWJWPFZ-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 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
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 244000045947 parasite Species 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 230000035755 proliferation Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
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- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
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- 241000894007 species Species 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- 206010063094 Cerebral malaria Diseases 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 241000224016 Plasmodium Species 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 241000223821 Plasmodium malariae Species 0.000 description 1
- 241001505293 Plasmodium ovale Species 0.000 description 1
- 241000223810 Plasmodium vivax Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- KUCQYCKVKVOKAY-CTYIDZIISA-N atovaquone Chemical compound C1([C@H]2CC[C@@H](CC2)C2=C(C(C3=CC=CC=C3C2=O)=O)O)=CC=C(Cl)C=C1 KUCQYCKVKVOKAY-CTYIDZIISA-N 0.000 description 1
- 229960003159 atovaquone Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 229940118768 plasmodium malariae Drugs 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29582110P | 2010-01-18 | 2010-01-18 | |
| US61/295821 | 2010-01-18 | ||
| PCT/IB2011/050192 WO2011086531A2 (en) | 2010-01-18 | 2011-01-17 | New anti-malarial agents |
Publications (1)
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| BR112012017713A2 true BR112012017713A2 (pt) | 2020-06-23 |
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| JP (1) | JP5735986B2 (https=) |
| CN (1) | CN102812006B (https=) |
| BR (1) | BR112012017713A2 (https=) |
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| DK (1) | DK2526090T3 (https=) |
| ES (1) | ES2551875T3 (https=) |
| HR (1) | HRP20151143T1 (https=) |
| HU (1) | HUE027946T2 (https=) |
| ME (1) | ME02315B (https=) |
| PL (1) | PL2526090T3 (https=) |
| PT (1) | PT2526090E (https=) |
| RS (1) | RS54339B1 (https=) |
| SI (1) | SI2526090T1 (https=) |
| SM (1) | SMT201500291B (https=) |
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| ES2921576T3 (es) | 2008-12-19 | 2022-08-29 | Vertex Pharma | Compuestos útiles como inhibidores de la quinasa ATR |
| US9334244B2 (en) | 2010-05-12 | 2016-05-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| CA2798760A1 (en) * | 2010-05-12 | 2011-11-17 | Vertex Pharmaceuticals Incorporated | 2-aminopyridine derivatives useful as inhibitors of atr kinase |
| NZ603477A (en) | 2010-05-12 | 2014-09-26 | Vertex Pharma | Compounds useful as inhibitors of atr kinase |
| CA2828578A1 (en) * | 2011-03-04 | 2012-09-13 | Lexicon Pharmaceuticals, Inc. | Mst1 kinase inhibitors and methods of their use |
| CN108685922A (zh) | 2011-09-30 | 2018-10-23 | 沃泰克斯药物股份有限公司 | 用atr抑制剂治疗胰腺癌和非小细胞肺癌 |
| CN106496173A (zh) | 2011-09-30 | 2017-03-15 | 沃泰克斯药物股份有限公司 | 用于制备可用作atr激酶抑制剂的化合物的方法 |
| LT2814820T (lt) * | 2012-02-17 | 2016-10-25 | University Of Cape Town | Antimaliariniai agentai |
| CN108478577A (zh) | 2012-04-05 | 2018-09-04 | 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 |
| JP6513073B2 (ja) * | 2013-03-15 | 2019-05-15 | ダウ アグロサイエンシィズ エルエルシー | ４−アミノ−６−（複素環式）ピコリネートおよび６−アミノ−２−（複素環式）ピリミジン−４−カルボキシレートならびに除草剤としてのそれらの使用 |
| PT2970185T (pt) | 2013-03-15 | 2023-10-06 | Corteva Agriscience Llc | 4-amino-6-(heterocíclico)picolinatos e 6-amino-2-(heterocíclico)pirimidino-4-carboxilatos e seu uso como herbicidas |
| US9862711B2 (en) | 2014-04-24 | 2018-01-09 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| BR112016024484A2 (pt) * | 2014-04-24 | 2017-08-15 | Novartis Ag | derivados de aminopiridina como inibidores de fosfatidilinositol 3-quinase |
| 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 |
| AU2016331955B2 (en) | 2015-09-30 | 2022-07-21 | 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 |
| US11919902B2 (en) * | 2017-12-22 | 2024-03-05 | Hibercell, Inc. | Aryl-bipyridine amine derivatives as phosphatidylinositol phosphate kinase inhibitors |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | 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 |
| JP2025531008A (ja) | 2022-08-09 | 2025-09-19 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | フロピリミジン誘導体 |
| 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 |
| WO2007032016A1 (en) | 2005-09-12 | 2007-03-22 | 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 |
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| JP2013517264A (ja) | 2013-05-16 |
| WO2011086531A3 (en) | 2011-09-29 |
| ME02315B (me) | 2016-06-20 |
| HK1175472A1 (zh) | 2013-07-05 |
| JP5735986B2 (ja) | 2015-06-17 |
| RS54339B1 (sr) | 2016-02-29 |
| HUE027946T2 (en) | 2016-11-28 |
| WO2011086531A2 (en) | 2011-07-21 |
| US20120295905A1 (en) | 2012-11-22 |
| PT2526090E (pt) | 2015-11-30 |
| EP2526090A2 (en) | 2012-11-28 |
| HRP20151143T1 (hr) | 2015-12-04 |
| CN102812006A (zh) | 2012-12-05 |
| CN102812006B (zh) | 2016-01-20 |
| SMT201500291B (it) | 2016-01-08 |
| SI2526090T1 (sl) | 2015-11-30 |
| CA2787121A1 (en) | 2011-07-21 |
| EP2526090B1 (en) | 2015-08-19 |
| CA2787121C (en) | 2018-07-17 |
| PL2526090T3 (pl) | 2016-04-29 |
| DK2526090T3 (en) | 2015-10-19 |
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