HRP20121022T1 - Kondenzirani bicikliäśki pirimidini - Google Patents
Kondenzirani bicikliäśki pirimidini Download PDFInfo
- Publication number
- HRP20121022T1 HRP20121022T1 HRP20121022AT HRP20121022T HRP20121022T1 HR P20121022 T1 HRP20121022 T1 HR P20121022T1 HR P20121022A T HRP20121022A T HR P20121022AT HR P20121022 T HRP20121022 T HR P20121022T HR P20121022 T1 HRP20121022 T1 HR P20121022T1
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- methyl
- piperidin
- pyrimidine
- triazol
- Prior art date
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- -1 bicyclic pyrimidines Chemical class 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 44
- 150000003839 salts Chemical class 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims 6
- 238000011282 treatment Methods 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 102000001253 Protein Kinase Human genes 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000006882 induction of apoptosis Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 108060006633 protein kinase Proteins 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
- VVJADIHTZGFTNI-UHFFFAOYSA-N 2,7-dimethyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=C(C)N2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 VVJADIHTZGFTNI-UHFFFAOYSA-N 0.000 claims 1
- VKUPCPYIBFRQRJ-UHFFFAOYSA-N 2,7-dimethyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=C(C)N2N=C(C)C=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 VKUPCPYIBFRQRJ-UHFFFAOYSA-N 0.000 claims 1
- WELWRBPANJAEMX-UHFFFAOYSA-N 2-[5-[1-[[4-(2-methyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)phenyl]methyl]piperidin-4-yl]-1h-1,2,4-triazol-3-yl]-1,3-thiazole Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=NC=CS1 WELWRBPANJAEMX-UHFFFAOYSA-N 0.000 claims 1
- KOOCJDFXNSBFPO-UHFFFAOYSA-N 2-[5-[1-[[4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)phenyl]methyl]piperidin-4-yl]-1h-1,2,4-triazol-3-yl]-1,3-thiazole Chemical compound C=1C=C(C=2C(=CN3N=CC=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=NC=1C1=NC=CS1 KOOCJDFXNSBFPO-UHFFFAOYSA-N 0.000 claims 1
- TUCZYGDDMHHBHL-UHFFFAOYSA-N 2-bromo-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(Br)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 TUCZYGDDMHHBHL-UHFFFAOYSA-N 0.000 claims 1
- YOEJIGKXMMUURR-UHFFFAOYSA-N 2-cyclobutyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=C(N=C3N=2)C2CCC2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 YOEJIGKXMMUURR-UHFFFAOYSA-N 0.000 claims 1
- QOPKUWDEMVSOFK-UHFFFAOYSA-N 2-cyclopropyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=C(N=C3N=2)C2CC2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 QOPKUWDEMVSOFK-UHFFFAOYSA-N 0.000 claims 1
- MLSZQTUMCJTVHA-UHFFFAOYSA-N 2-cyclopropyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=C(C=C3N=2)C2CC2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 MLSZQTUMCJTVHA-UHFFFAOYSA-N 0.000 claims 1
- JHYNHRIGHOATHO-UHFFFAOYSA-N 2-ethyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(CC)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 JHYNHRIGHOATHO-UHFFFAOYSA-N 0.000 claims 1
- AOOBAHAXYJDCOJ-UHFFFAOYSA-N 2-ethyl-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=NC(CC)=CN2C=C1C1=CC=CC=C1 AOOBAHAXYJDCOJ-UHFFFAOYSA-N 0.000 claims 1
- LPEOCRMMLPIMNB-UHFFFAOYSA-N 2-ethynyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C#C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 LPEOCRMMLPIMNB-UHFFFAOYSA-N 0.000 claims 1
- XJJRMKQFOMGIAQ-UHFFFAOYSA-N 2-methoxy-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(OC)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 XJJRMKQFOMGIAQ-UHFFFAOYSA-N 0.000 claims 1
- DYQUTVGJXFSHEH-UHFFFAOYSA-N 2-methyl-5-[4-[[4-[3-(6-methylpyridin-2-yl)-1h-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CC(C)=N1 DYQUTVGJXFSHEH-UHFFFAOYSA-N 0.000 claims 1
- IOMPSCDRXOGMTE-UHFFFAOYSA-N 2-methyl-6-phenyl-5-[4-[[4-(3-phenyl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CC=C1 IOMPSCDRXOGMTE-UHFFFAOYSA-N 0.000 claims 1
- QUFWNNHKUNWWOZ-UHFFFAOYSA-N 2-methyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 QUFWNNHKUNWWOZ-UHFFFAOYSA-N 0.000 claims 1
- PRWJUJUQDXGWGP-UHFFFAOYSA-N 2-methyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)C=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 PRWJUJUQDXGWGP-UHFFFAOYSA-N 0.000 claims 1
- RLQRMIGCRSKPPT-UHFFFAOYSA-N 2-methyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-pyrazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(NN=1)=CC=1C1=CC=CC=N1 RLQRMIGCRSKPPT-UHFFFAOYSA-N 0.000 claims 1
- KJTASMGWEKTLLD-UHFFFAOYSA-N 2-methyl-6-phenyl-5-[4-[[4-(3-pyridin-4-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=NC=C1 KJTASMGWEKTLLD-UHFFFAOYSA-N 0.000 claims 1
- LVDRPBBCBYKGBF-UHFFFAOYSA-N 2-methyl-6-phenyl-5-[4-[[4-(3-pyrimidin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=NC=CC=N1 LVDRPBBCBYKGBF-UHFFFAOYSA-N 0.000 claims 1
- WPBBRYWUHRLCRV-UHFFFAOYSA-N 2-methyl-6-phenyl-5-[4-[[4-[3-(1H-pyrrol-2-yl)-1H-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CN1 WPBBRYWUHRLCRV-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 claims 1
- FQMRXSCEWAPNFC-UHFFFAOYSA-N 3-bromo-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=C(Br)C=NN2C=C1C1=CC=CC=C1 FQMRXSCEWAPNFC-UHFFFAOYSA-N 0.000 claims 1
- YBUKESGYTGHLHF-UHFFFAOYSA-N 3-bromo-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2C(Br)=CN=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 YBUKESGYTGHLHF-UHFFFAOYSA-N 0.000 claims 1
- KASSCFAAVKHYJH-UHFFFAOYSA-N 3-chloro-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=C(Cl)C=NN2C=C1C1=CC=CC=C1 KASSCFAAVKHYJH-UHFFFAOYSA-N 0.000 claims 1
- IRCVKELGYYDUJK-UHFFFAOYSA-N 3-chloro-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2C(Cl)=CN=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 IRCVKELGYYDUJK-UHFFFAOYSA-N 0.000 claims 1
- AWUPTOWEPMPQID-UHFFFAOYSA-N 3-ethyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=C(CC)C=NN2C=C1C1=CC=CC=C1 AWUPTOWEPMPQID-UHFFFAOYSA-N 0.000 claims 1
- WSHWWQSPFZXOGR-UHFFFAOYSA-N 3-ethyl-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2C(CC)=CN=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 WSHWWQSPFZXOGR-UHFFFAOYSA-N 0.000 claims 1
- LYBAOFGRXGWEGN-UHFFFAOYSA-N 3-ethynyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=C(C#C)C=NN2C=C1C1=CC=CC=C1 LYBAOFGRXGWEGN-UHFFFAOYSA-N 0.000 claims 1
- HAWDKYORFVHHAA-UHFFFAOYSA-N 3-ethynyl-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2C(C#C)=CN=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 HAWDKYORFVHHAA-UHFFFAOYSA-N 0.000 claims 1
- ZTINZBQANVITJM-UHFFFAOYSA-N 3-fluoro-6-phenyl-7-[4-[[4-(3-pyrazin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2C(F)=CN=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CN=CC=N1 ZTINZBQANVITJM-UHFFFAOYSA-N 0.000 claims 1
- COKBOBLRIYUWJN-UHFFFAOYSA-N 3-fluoro-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2C(F)=CN=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 COKBOBLRIYUWJN-UHFFFAOYSA-N 0.000 claims 1
- CXLBWAPSKIKVPO-UHFFFAOYSA-N 3-fluoro-6-phenyl-7-[4-[[4-(3-pyrimidin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2C(F)=CN=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=NC=CC=N1 CXLBWAPSKIKVPO-UHFFFAOYSA-N 0.000 claims 1
- HPDCJRRTVMMTJM-UHFFFAOYSA-N 3-methyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=C(C)C=NN2C=C1C1=CC=CC=C1 HPDCJRRTVMMTJM-UHFFFAOYSA-N 0.000 claims 1
- MNKDDAUPSORZEW-UHFFFAOYSA-N 3-methyl-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2C(C)=CN=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 MNKDDAUPSORZEW-UHFFFAOYSA-N 0.000 claims 1
- BSOWRVUIXQPVPB-UHFFFAOYSA-N 5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-6-thiophen-3-ylpyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=CC=C3N=2)C2=CSC=C2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 BSOWRVUIXQPVPB-UHFFFAOYSA-N 0.000 claims 1
- CVUWNDVPFVLWOJ-UHFFFAOYSA-N 5-[4-[[4-[3-(6-methylpyridin-2-yl)-1h-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-6-phenylpyrazolo[1,5-a]pyrimidine Chemical compound CC1=CC=CC(C=2N=C(NN=2)C2CCN(CC=3C=CC(=CC=3)C=3C(=CN4N=CC=C4N=3)C=3C=CC=CC=3)CC2)=N1 CVUWNDVPFVLWOJ-UHFFFAOYSA-N 0.000 claims 1
- VNHAAMSYXOTHOQ-UHFFFAOYSA-N 5-[4-[[4-[3-(furan-2-yl)-1h-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-2-methyl-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CO1 VNHAAMSYXOTHOQ-UHFFFAOYSA-N 0.000 claims 1
- YOCFEKLZKFNLSB-UHFFFAOYSA-N 5-[4-[[4-[3-(furan-2-yl)-1h-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-6-phenylpyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=CC=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CO1 YOCFEKLZKFNLSB-UHFFFAOYSA-N 0.000 claims 1
- PFTKTDTYABELGP-UHFFFAOYSA-N 5-methyl-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=NC=CN2C(C)=C1C1=CC=CC=C1 PFTKTDTYABELGP-UHFFFAOYSA-N 0.000 claims 1
- DQGYWUCWOKTBGZ-UHFFFAOYSA-N 6-phenyl-2-propan-2-yl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=CC=CC=1C1=CN2N=C(C(C)C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 DQGYWUCWOKTBGZ-UHFFFAOYSA-N 0.000 claims 1
- URQZCCLHPWDDSX-UHFFFAOYSA-N 6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine Chemical compound C=1C=CC=CC=1C1=CN2N=C(N)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 URQZCCLHPWDDSX-UHFFFAOYSA-N 0.000 claims 1
- CSZZKKYIUDCUMN-UHFFFAOYSA-N 6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=CN=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 CSZZKKYIUDCUMN-UHFFFAOYSA-N 0.000 claims 1
- ITESNFXWLKFTJY-UHFFFAOYSA-N 6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=CC=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 ITESNFXWLKFTJY-UHFFFAOYSA-N 0.000 claims 1
- NFUHAGHOUWDILI-UHFFFAOYSA-N 6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine-2-carboxamide Chemical compound C=1C=CC=CC=1C1=CN2N=C(C(=O)N)C=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 NFUHAGHOUWDILI-UHFFFAOYSA-N 0.000 claims 1
- MRIBCLJGZPFAEU-UHFFFAOYSA-N 6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine-2-carboxylic acid Chemical compound C=1C=CC=CC=1C1=CN2N=C(C(=O)O)C=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 MRIBCLJGZPFAEU-UHFFFAOYSA-N 0.000 claims 1
- NKJHOHDYLJLAHY-UHFFFAOYSA-N 6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-pyrazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=CC=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=CC=1C1=CC=CC=N1 NKJHOHDYLJLAHY-UHFFFAOYSA-N 0.000 claims 1
- MYOSTFNKBJQSDR-UHFFFAOYSA-N 6-phenyl-5-[4-[[4-(3-pyrimidin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=CC=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=NC=1C1=NC=CC=N1 MYOSTFNKBJQSDR-UHFFFAOYSA-N 0.000 claims 1
- NCVNPHOGDBUQBI-UHFFFAOYSA-N 6-phenyl-5-[4-[[4-[3-(1H-pyrrol-2-yl)-1H-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3N=CC=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CN1 NCVNPHOGDBUQBI-UHFFFAOYSA-N 0.000 claims 1
- GFJWBXSXROZJGU-UHFFFAOYSA-N 6-phenyl-7-[4-[1-[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]ethyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C=2C=CC=CC=2)C=CC=1C(C)N(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 GFJWBXSXROZJGU-UHFFFAOYSA-N 0.000 claims 1
- ORAGVAABYQIXGP-UHFFFAOYSA-N 6-phenyl-7-[4-[[4-(3-pyrazin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=CN=CC=N1 ORAGVAABYQIXGP-UHFFFAOYSA-N 0.000 claims 1
- FYJRJYAYKPMWIA-UHFFFAOYSA-N 6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-2-(trifluoromethyl)imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=NC(C(F)(F)F)=CN2C=C1C1=CC=CC=C1 FYJRJYAYKPMWIA-UHFFFAOYSA-N 0.000 claims 1
- TXYLIIUPZJCYCU-UHFFFAOYSA-N 6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CC=N1 TXYLIIUPZJCYCU-UHFFFAOYSA-N 0.000 claims 1
- KJOWRJQDCACXQU-UHFFFAOYSA-N 6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-pyrazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=CC=1C1=CC=CC=N1 KJOWRJQDCACXQU-UHFFFAOYSA-N 0.000 claims 1
- JZOQPHABFRHDIZ-UHFFFAOYSA-N 6-phenyl-7-[4-[[4-(3-pyrimidin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=NC=CC=N1 JZOQPHABFRHDIZ-UHFFFAOYSA-N 0.000 claims 1
- SPKQPLKCICBERJ-UHFFFAOYSA-N 6-phenyl-7-[4-[[4-(4-pyridin-2-ylimidazol-1-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1N(C=1)C=NC=1C1=CC=CC=N1 SPKQPLKCICBERJ-UHFFFAOYSA-N 0.000 claims 1
- YDOSOFSWTLLAEA-UHFFFAOYSA-N 6-phenyl-7-[4-[[4-[3-(1H-pyrrol-2-yl)-1H-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CN1 YDOSOFSWTLLAEA-UHFFFAOYSA-N 0.000 claims 1
- VZEMFEZJGXHIDJ-UHFFFAOYSA-N 7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-6-thiophen-3-ylimidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C2=CSC=C2)C=CC=1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 VZEMFEZJGXHIDJ-UHFFFAOYSA-N 0.000 claims 1
- MQFBREBCOLUCFP-UHFFFAOYSA-N 7-[4-[[4-[3-(4-methoxypyridin-2-yl)-1h-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-6-phenylimidazo[1,2-a]pyrimidine Chemical compound COC1=CC=NC(C=2NN=C(N=2)C2CCN(CC=3C=CC(=CC=3)C=3C(=CN4C=CN=C4N=3)C=3C=CC=CC=3)CC2)=C1 MQFBREBCOLUCFP-UHFFFAOYSA-N 0.000 claims 1
- CCXIAQRLCFNNKE-UHFFFAOYSA-N 7-[4-[[4-[3-(4-methylpyridin-2-yl)-1h-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-6-phenylimidazo[1,2-a]pyrimidine Chemical compound CC1=CC=NC(C=2NN=C(N=2)C2CCN(CC=3C=CC(=CC=3)C=3C(=CN4C=CN=C4N=3)C=3C=CC=CC=3)CC2)=C1 CCXIAQRLCFNNKE-UHFFFAOYSA-N 0.000 claims 1
- FANNXWZXQXGNNZ-UHFFFAOYSA-N 7-[4-[[4-[3-(6-methylpyridin-2-yl)-1h-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-6-phenylimidazo[1,2-a]pyrimidine Chemical compound CC1=CC=CC(C=2NN=C(N=2)C2CCN(CC=3C=CC(=CC=3)C=3C(=CN4C=CN=C4N=3)C=3C=CC=CC=3)CC2)=N1 FANNXWZXQXGNNZ-UHFFFAOYSA-N 0.000 claims 1
- VPXPKKUXEJRLNV-UHFFFAOYSA-N 7-[4-[[4-[3-(furan-2-yl)-1h-1,2,4-triazol-5-yl]piperidin-1-yl]methyl]phenyl]-6-phenylimidazo[1,2-a]pyrimidine Chemical compound C=1C=C(C=2C(=CN3C=CN=C3N=2)C=2C=CC=CC=2)C=CC=1CN(CC1)CCC1C(NN=1)=NC=1C1=CC=CO1 VPXPKKUXEJRLNV-UHFFFAOYSA-N 0.000 claims 1
- LSJUHNPCIHNASN-UHFFFAOYSA-N 7-methoxy-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=CC=NN2C(OC)=C1C1=CC=CC=C1 LSJUHNPCIHNASN-UHFFFAOYSA-N 0.000 claims 1
- 230000000973 chemotherapeutic effect Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
- INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- VVZHOEBVSNLQAE-UHFFFAOYSA-N methyl 6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]pyrazolo[1,5-a]pyrimidine-2-carboxylate Chemical compound C=1C=CC=CC=1C1=CN2N=C(C(=O)OC)C=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 VVZHOEBVSNLQAE-UHFFFAOYSA-N 0.000 claims 1
- 230000000116 mitigating effect Effects 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- GGKLTOSQEAOLPR-UHFFFAOYSA-N n,n-dimethyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine Chemical compound C=1C=CC=CC=1C1=CN2N=C(N(C)C)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 GGKLTOSQEAOLPR-UHFFFAOYSA-N 0.000 claims 1
- JMSZSEPZPHLQKO-UHFFFAOYSA-N n-methyl-6-phenyl-5-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine Chemical compound C=1C=CC=CC=1C1=CN2N=C(NC)N=C2N=C1C(C=C1)=CC=C1CN(CC1)CCC1C(N=1)=NNC=1C1=CC=CC=N1 JMSZSEPZPHLQKO-UHFFFAOYSA-N 0.000 claims 1
- QXUZYCYXJYINSO-UHFFFAOYSA-N n-methyl-6-phenyl-7-[4-[[4-(3-pyridin-2-yl-1h-1,2,4-triazol-5-yl)piperidin-1-yl]methyl]phenyl]imidazo[1,2-a]pyrimidin-5-amine Chemical compound C=1C=C(CN2CCC(CC2)C=2N=C(NN=2)C=2N=CC=CC=2)C=CC=1C1=NC2=NC=CN2C(NC)=C1C1=CC=CC=C1 QXUZYCYXJYINSO-UHFFFAOYSA-N 0.000 claims 1
- 230000009826 neoplastic cell growth Effects 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- ZFCHNZDUMIOWFV-UHFFFAOYSA-M pyrimidine-2-carboxylate Chemical compound [O-]C(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-M 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000005559 triazolylene group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (13)
1. Spoj sa formulom (I)
[image]
naznačen time da prsten B i pirimidin na koji je kondenziran tvore prstenasti sustav odabran od
[image]
pri čemu
R1 je vodik, 1-4C-alkil, halogen, amino, 1-4C-alkoksi, cijano, 3-7C-cikloalkil, 2-4C-alkenil, 2-4C-alkinil, 3-7C-cikloalkoksi, mono- ili di-1-4C-alkilamino, mono- ili di-1-4C-alkilaminokarbonil, - C(O)NH2, -C(O)OR2 ili trifluorometil,
R2 je vodik ili 1-4C-alkil,
R3 je vodik, 1-4C-alkil ili halogen,
R4 je fenil ili tienil,
R5 je vodik, 1-4C-alkoksi, amino, mono- ili di- 1-4C-alkilamino, 1-4C-alkil ili 3-7C-cikloalkil,
R6 je vodik ili 1-4C-alkil,
R7 je -W-Y,
W je monociklički 5-člani heteroarilen koji sadrži 1 atom dušika i proizvoljno 1 ili 2 dodatna heteroatoma koji su neovisno odabrani od kisika, dušika i sumpora, i pri čemu je heteroarilen proizvoljno supstituiran sa R8,
R8 je 1-4C-alkil ili 3-7C-cikloalkil,
Y je fenil ili monociklički 5 ili 6 člani heteroaril koji sadrži 1 atom dušika i proizvoljno 1 ili 2 dodatna heteroatoma koji su neovisno odabrani od kisika, dušika i sumpora, i pri čemu je heteroaril proizvoljno supstituiran sa R9,
R9 je 1-4C-alkil, 1-4C-alkoksi ili halogen,
ili sol, naročito farmaceutski prihvatljiva sol, tautomer, ili stereoizomer navedenog spoja, ili sol, naročito farmaceutski prihvatljiva sol navedenog tautomera ili navedenog stereoizomera.
2. Spoj prema zahtjevu 1, naznačen time da prsten B i pirimidin na koji je kondenziran tvore prstenasti sustav odabran od
[image]
pri čemu
R1 je vodik, 1-4C-alkil, halogen, amino, 1-4C-alkoksi, cijano, 3-7C-cikloalkil, 2-4C-alkenil, 2-4C-alkinil, 3-7C-cikloalkoksi, mono- ili di-1-4C-alkilamino, mono- ili di-1-4C-alkilaminokarbonil, - C(O)NH2, -C(O)OR2 ili trifluorometil,
R2 je vodik ili 1-4C-alkil,
R3 je vodik,
R4 je fenil ili tienil,
R5 je vodik, 1-4C-alkoksi, amino, mono- ili di-1-4C-alkilamino, 1-4C-alkil ili 3-7C-cikloalkil,
R6 je vodik ili 1-4-C-alkil,
R7 je -W-Y,
W je triazolilen, pirazolilen ili imidazolilen, svaki od navedenih je proizvoljno supstituiran sa R8,
R8 je 1-4C-alkil ili 3-7C-cikloalkil,
Y je fenil, pirolil, furanil, tienil, tiazolil, oksazolil, tiadiazolil, oksadiazolil, piridinil, pirimidinil, pirazinil ili piridazinil, svaki od navedenih je proizvoljno supstituiran sa R9,
R9 je 1-4C-alkil, 1-4C-alkoksi ili halogen,
ili sol, naročito farmaceutski prihvatljiva sol, tautomer, ili stereoizomer navedenog spoja, ili sol, naročito farmaceutski prihvatljiva sol navedenog tautomera ili navedenog stereoizomera.
3. Spoj prema zahtjevu 1 ili 2, naznačen time da prsten B i pirimidin na koji je kondenziran tvore prstenasti sustav odabran od
[image]
pri čemu
R1 je vodik, 1-4C-alkil, halogen, amino, 1-4C-alkoksi, cijano, 3-7C-cikloalkil, 2-4C-alkenil, 2-4C-alkinil, 3-7C-cikloalkoksi, mono- ili di-1-4C-alkilamino, mono- ili di-1-4C-alkilaminokarbonil, - C(O)NH2, -C(O)OR2 ili trifluorometil,
R2 je vodik ili 1-4C-alkil,
R3 je vodik,
R4 je fenil ili tienil,
R5 je vodik, 1-4C-alkoksi, amino, mono- ili di-1-4C-alkilamino, 1-4C-alkil ili 3-7C-cikloalkil,
R6 je vodik ili metil,
R7 je -W-Y,
W je 1,2,4-triazolilen, pirazolilen ili imidazolilen,
Y je fenil, furan-2-il, pirol-2-il, tien-2-il, tiazol-2-il, tiazol-4-il, oksazol-2-il, oksazol-4-il, 1,3,4-tiadiazol-2-il, 1,3,4-oksadiazol-2-il, piridin-2-il, piridin-4-il, pirimidin-2-il, pirimidin-4-il, pirazin-2-il ili piridazin-3-il, svaki od navedenih je proizvoljno supstituiran sa R9,
R9 je 1-4C-alkil, 1-4C-alkoksi ili halogen,
ili sol, naročito farmaceutski prihvatljiva sol, tautomer, ili stereoizomer navedenog spoja, ili sol, naročito farmaceutski prihvatljiva sol navedenog tautomera ili navedenog stereoizomera.
4. Spoj prema zahtjevu 1, 2 ili 3 naznačen time da prsten B i pirimidin na koji je kondenziran tvore prstenasti sustav odabran od
[image]
pri čemu
R1 je vodik, 1-4C-alkil, halogen, amino, 1-4C-alkoksi, cijano, 3-7C-cikloalkil, 2-4C-alkenil, 2-4C-alkinil, mono- ili di-1-4C-alkilamino, -C(O)OR2 ili trifluorometil,
R2 je 1-4C-alkil,
R3 je vodik,
R4 je fenil ili tienil,
R5 je vodik, 1-4C-alkoksi, mono- ili di-1-4C-alkilamino ili 1-4C-alkil,
R6 je vodik ili metil,
R7 je -W-Y,
W je 1,2,4-triazolilen ili pirazolilen,
Y je fenil, furan-2-il, pirol-2-il, piridin-4-il, tiazol-2-il, piridin-2-il, pirimidin-2-il, pirazin-2-il, pirimidin-4-il ili piridazin-3-il, svaki od navedenih je proizvoljno supstituiran sa R9,
R9 je 1-4C-alkil, 1-4C-alkoksi ili halogen,
ili sol, naročito farmaceutski prihvatljiva sol, tautomer, ili stereoizomer navedenog spoja, ili sol, naročito farmaceutski prihvatljiva sol navedenog tautomera ili navedenog stereoizomera.
5. Spoj prema zahtjevu 1, 2, 3 ili 4 naznačen time da je odabran iz skupine koja sadrži
6-fenil-7-(4-{[4-(3-piridin-2-il-1,2,4-triazol-5-il)piperidin-1-il]metil}fenil)imidazo[1,2a]-pirimidin;
6-fenil-5-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]-pirimidin;
2-metil-6-fenil-5-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]-triazolo[1,5-a]pirimidin;
2-ciklopropil-6-fenil-5-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]-triazolo[1,5-a]pirimidin;
6-fenil-7-(4-{[4-(3-piridin-2-il-pirazol-5-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
6-fenil-7-(4-{[4-(5-piridin-4-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]-pirimidin;
2-ciklobutil-6-fenil-5-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]-triazolo[1,5-a]pirimidin;
6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]-pirimidin-3-karbonitril;
3-fluoro-6-fenil-7-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1 - il]metil}fenil)-imidazo[1,2-a]pirimidin;
N-metil-6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-imidazo[1,2-a]pirimidin-5-amin;
3-bromo-6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
3-kloro-6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
3-etinil-6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}-fenil)imidazo[1,2-a]pirimidin;
3-metil-6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-3-vinilimidazo[1,2-a]pirimidin;
Etil-6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin-2-karboksilat;
2-etil-6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
6-fenil-7-(4-{[4-(5-pirimidin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
6-fenil-5-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
6-fenil-7-(4-{[4-(4-piridin-2-il-imidazol-1-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
6-fenil-7-(4-{[4-(5-pirazin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
3-etil-6-fenil-7-(4-{[4-(5-piridin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
6-fenil-7-(4-{1-[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]etil}fenil)imidazo[1,2-a]pirimidin;
3-fluoro-6-fenil-7-(4-{[4-(5-pirazin-2-il-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)imidazo[1,2-a]pirimidin;
3-fluoro-6-fenil-7-(4-{[4-(5-pirimidin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-imidazo[1,2-a]pirimidin;
6-fenil-7-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-2-(trifluorometil)imidazo[1,2-a]pirimidin;
5-metil-6-fenil-7-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-imidazo[1,2-a]pirimidin;
2-Isopropil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
7-Metoksi-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
3-Kloro-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
3-Bromo-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
6-Fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin-3-karbonitril;
3-Etinil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
3-Etil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
7-[4-({4-[5-(4-Metilpiridin-2-il)-1H-1,2,4-triazol-3-il]piperidin-1-il}metil)fenil]-6-fenilimidazo[1,2-a]pirimidin;
7-[4-({4-[5-(6-Metilpiridin-2-il)-1H-1,2,4-triazol-3-il]piperidin-1-il}metil)fenil]-6-fenilimidazo[1,2-a]pirimidin;
3-Metil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
2,7-Dimetil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
2-Etil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
2-Metil-6-fenil-5-[4-({4-[5-(1,3-tiazol-2-il)-1H-1,2,4-triazol-3-il]piperidin-1-il}metil)fenil][1,2,4]triazolo[1,5-a]pirimidin;
2-Metil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
2-Metil-6-fenil-5-(4-{[4-(5-pirimidin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
2-Metil-6-fenil-5-(4-{[4-(3-piridin-2-il-1H-pirazol-5-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
2-Metil-6-fenil-5-(4-{[4-(5-piridin-4-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
2-Ciklopropil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
2,7-Dimetil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
5-(4-{[4-(5-Piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-6-(3-tienil)pirazolo[1,5-a]pirimidin;
7-(4-{[4-(5-Piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-6-(3-tienil)imidazo[1,2-a]pirimidin;
2-Bromo-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
2-Etinil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
2-Metil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-6-(3-tienil)[1,2,4]tiazolo[1,5-a]pirimidin;
N,N-Dimetil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin-2-amin;
6-Fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)-2-(trifluorometil)[1,2,4]triazolo[1,5-a]pirimidin;
N,N,2-Trimetil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin-7-amin;
N-Metil-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin-2-amin;
2-Metoksi-6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
6-Fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin-2-amin;
6-Fenil-7-[4-({4-[3-(1H-pirol-2-il)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil]imidazo[1,2-a]pirimidin;
6-Fenil-5-(4-{[4-(3-pirimidin-2-il-1H-1,2,4-triazol-5-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
6-Fenil-5-[4-({4-[3-(1,3-tiazol-2-il)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil]pirazolo[1,5-a]pirimidin;
6-Fenil-5-(4-{[4-(3-piridin-4-il-1H-1,2,4-triazol-5-il)piperidin-1-il]metil}fenil)pirazolo[15-a]pirimidin;
6-Fenil-5-[4-({4-[3-(1H-pirol-2-il)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil]pirazolo[1,5-a]pirimidin;
2-Metil-6-fenil-5-[4-({4-[3-(1H-pirol-2-il)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil][1,2,4]triazolo[1,5-a]pirimidin;
2-Metil-5-[4-({4-[3-(6-metilpiridin-2-il)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil]-6-fenil[1,2,4]triazolo[1,5-a]pirimidin;
5-[4-({4-[3-(6-Metilpiridin-2-il)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil]-6-fenilpirazolo[1,5-a]pirimidin;
6-Fenil-5-(4-{[4-(3-piridin-2-il-1H-pirazol-5-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin;
Metil 6-fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin-2-karboksilat;
6-Fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin-2-karboksamid;
6-Fenil-5-(4-{[4-(5-piridin-2-il-1H-1,2,4-triazol-3-il)piperidin-1-il]metil}fenil)pirazolo[1,5-a]pirimidin-2-karboksilna kiselina;
5-[4-({4-[3-(2-furil)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil]-2-metil-6-fenil[1,2,4]triazolo[1,5-a]pirimidin;
5-[4-({4-[3-(2-furil)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil]-6-fenilpirazolo[1,5-a]pirimidin;
7-[4-({4-[3-(2-furil)-1H-1,2,4-triazol-5-il]piperidin-1-il}metil)fenil]-6-fenilimidazo[1,2-a]pirimidin;
2-metil-6-fenil-5-(4-{[4-(3-fenil-1H-1,2,4-triazol-5-il)piperidin-1-il]metil}fenil)[1,2,4]triazolo[1,5-a]pirimidin;
7-[4-({4-[5-(4-metoksipiridin-2-il)-1H-1,2,4-triazol-3-il]piperidin-1-il}metil)fenil]-6-fenilimidazo[1,2-a]pirimidin; i
6-fenil-7-{4-[4-(5-piridin-2-il-1H-[1,2,4]triazol-3-il)-piperidin-1-ilmetil]-fenil}-imidazo[1,2-a]pirimidin;
ili sol, naročito farmaceutski prihvatljiva sol, tautomer, ili stereoizomer navedenog spoja, ili sol, naročito farmaceutski prihvatljiva sol navedenog tautomera ili navedenog stereoizomera.
6. Spoj, njegov tautomer ili njegov stereoizomer, ili farmaceutski prihvatljiva sol navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5 naznačen time da je za uporabu kod liječenja ili za profilaksu bolesti.
7. Spoj, njegov tautomer ili njegov stereoizomer, ili farmaceutski prihvatljiva sol navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5, ili farmaceutski pripravak koji sadrži spoj, tautomer navedenog spoja ili stereoizomer navedenog spoja, ili farmaceutski prihvatljiva sol navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5, naznačen time da je za uporabu kod liječenja i/ili profilaksu hiperproliferativnih bolesti i/ili poremećaja koji reagiraju na indukciju apoptoze.
8. Spoj, njegov tautomer ili njegov stereoizomer, ili farmaceutski prihvatljiva sol navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5, ili farmaceutski pripravak koji sadrži spoj, tautomer navedenog spoja ili stereoizomer navedenog spoja, ili farmaceutski prihvatljiva sol navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5, naznačen time da je za liječenje raka.
9. Farmaceutski pripravak koji sadrži barem jedan spoj, tautomer navedenog spoja ili stereoizomer navedenog spoja, ili farmaceutski prihvatljiva sol navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5, naznačen time da zajedno sadrži barem jednu farmaceutski prihvatljivu pomoćnu tvar.
10. Kombinacija naznačena time da sadrži jednu ili više prvih aktivnih komponenti koje su odabrane između spojeva, tautomera navedenih spojeva, ili stereoizomera navedenih spojeva, ili farmaceutski prihvatljivih soli navedenih spojeva, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5, te jednu ili više drugih aktivnih komponenti koje su odabrane između kemoterapijskih anti-kanceroznih sredstava i anti-kanceroznih sredstava za specifičnim ciljevima.
11. Uporaba spoja, ili tautomera navedenog spoja, ili stereoizomera navedenog spoja ili farmaceutski prihvatljive soli navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5 naznačena time da je za proizvodnju farmaceutskog pripravka za liječenje, sprečavanje ili ublažavanje bolesti koja je posredovana sa nereguliranom funkcijom pojedinačne protein kinaze ili višestrukih protein kinaza i/ili poremećaja koji reagiraju na indukciju apoptoze.
12. Uporaba spoja, ili tautomera navedenog spoja, ili stereoizomera navedenog spoja ili farmaceutski prihvatljive soli navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5 naznačena time da je za proizvodnju farmaceutskog pripravka za liječenje benignih i/ili malignih neoplazija.
13. Uporaba spoja, ili tautomera navedenog spoja, ili stereoizomera navedenog spoja ili farmaceutski prihvatljive soli navedenog spoja, tautomera ili stereoizomera prema bilo kojem zahtjevu od 1 do 5 naznačena time da je za proizvodnju farmaceutskog pripravka za liječenje raka.
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| PT (1) | PT2188291E (hr) |
| RS (1) | RS52559B (hr) |
| SI (1) | SI2188291T1 (hr) |
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| TN (1) | TN2010000070A1 (hr) |
| TW (1) | TWI439272B (hr) |
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Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0717722A2 (pt) * | 2006-10-19 | 2013-10-29 | Takeda Pharmaceutical | Composto ou um sal do mesmo, pró-droga, ativador de glicoquinase, agente farmacêutico, métodos para ativar uma glicoquinase em um mamífero e para a profilaxia ou o tratamento de diabetes ou obesidade em um mamífero, e, uso do composto ou uma pró-droga do mesmo |
| BRPI0815207A2 (pt) | 2007-08-14 | 2017-03-28 | Bayer Schering Pharma Ag | pirimidinas bicíclicas fundidas |
| US8415376B2 (en) | 2008-05-30 | 2013-04-09 | Amgen Inc. | Inhibitors of PI3 kinase |
| ES2435804T3 (es) * | 2009-02-13 | 2013-12-23 | Bayer Intellectual Property Gmbh | Pirimidinas condensadas como inhibidores de Akt |
| KR20110114663A (ko) | 2009-02-13 | 2011-10-19 | 바이엘 파마 악티엔게젤샤프트 | 융합된 피리미딘 |
| EP2413932A4 (en) * | 2009-04-01 | 2012-09-19 | Merck Sharp & Dohme | INHIBITORS OF AKT ACTIVITY |
| JPWO2010125799A1 (ja) | 2009-04-27 | 2012-10-25 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有するウレア誘導体 |
| US20130184273A1 (en) * | 2010-07-13 | 2013-07-18 | Bayer Intellectual Property Gmbh | Bicyclic pyrimidines |
| JP5926727B2 (ja) | 2010-07-28 | 2016-05-25 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾ［１，２−ｂ］ピリダジン |
| CA2832374A1 (en) | 2011-04-07 | 2012-10-11 | Bayer Intellectual Property Gmbh | Imidazopyridazines as akt kinase inhibitors |
| EP2948447B1 (en) | 2013-01-23 | 2016-09-21 | Astrazeneca AB | Chemical compounds |
| US20140274685A1 (en) | 2013-03-15 | 2014-09-18 | Bayer Cropscience Lp | Compositions, additives, and methods for mitigating or controlling seed dust |
| WO2014146144A2 (en) * | 2013-03-15 | 2014-09-18 | Bayer Cropscience Lp | Compositions, additives, and methods for mitigating or controlling seed dust |
| CN111212839A (zh) | 2017-09-15 | 2020-05-29 | 艾杜罗生物科技公司 | 吡唑并嘧啶酮化合物及其用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA006483B1 (ru) | 2000-06-30 | 2005-12-29 | Уайт | Замещенные триазолопиримидины в качестве противораковых средств |
| US7449488B2 (en) * | 2002-06-04 | 2008-11-11 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| US7579355B2 (en) | 2003-04-24 | 2009-08-25 | Merck & Co., Inc. | Inhibitors of Akt activity |
| CA2561311A1 (en) * | 2004-04-09 | 2005-10-27 | Merck & Co., Inc. | Inhibitors of akt activity |
| AR050188A1 (es) * | 2004-08-03 | 2006-10-04 | Uriach Y Compania S A J | Compuestos heterociclicos condensados utiles en terapia como inhibidores de quinasas p38 y composiciones farmaceuticas que los contienen |
| US7544677B2 (en) * | 2004-08-23 | 2009-06-09 | Merck & Co., Inc. | Inhibitors of Akt activity |
| JP2008524339A (ja) | 2004-12-15 | 2008-07-10 | メルク エンド カムパニー インコーポレーテッド | Ａｋｔ活性のインヒビター |
| AU2005322085B2 (en) | 2004-12-28 | 2012-07-19 | Exelixis, Inc. | [1H-pyrazolo[3, 4-d]pyrimidin-4-yl]-piperidine or -piperazine compounds as serine-threonine kinase modulators (p70S6K, Atk1 and Atk2) for the treatment of immunological, inflammatory and proliferative diseases |
| US7589068B2 (en) | 2005-02-14 | 2009-09-15 | Merck & Co., Inc. | Inhibitors of Akt activity |
| EP1898903B8 (en) | 2005-06-10 | 2013-05-15 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| BRPI0815207A2 (pt) | 2007-08-14 | 2017-03-28 | Bayer Schering Pharma Ag | pirimidinas bicíclicas fundidas |
| KR20110114663A (ko) * | 2009-02-13 | 2011-10-19 | 바이엘 파마 악티엔게젤샤프트 | 융합된 피리미딘 |
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