JP2009542720A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009542720A5 JP2009542720A5 JP2009518629A JP2009518629A JP2009542720A5 JP 2009542720 A5 JP2009542720 A5 JP 2009542720A5 JP 2009518629 A JP2009518629 A JP 2009518629A JP 2009518629 A JP2009518629 A JP 2009518629A JP 2009542720 A5 JP2009542720 A5 JP 2009542720A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound according
- cycloalkyl
- item
- independently
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 76
- -1 CH 2 F Chemical compound 0.000 claims description 69
- 125000004429 atom Chemical group 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims description 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 0 *C1OC(*)c2ncnc(N3C(*)CN(*)CC3)c12 Chemical compound *C1OC(*)c2ncnc(N3C(*)CN(*)CC3)c12 0.000 description 90
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 201000010099 disease Diseases 0.000 description 5
- YUIYTAHPRXTDGF-UHFFFAOYSA-N CC(C)(CC(C(C)=O)c(cc1)ccc1Cl)N Chemical compound CC(C)(CC(C(C)=O)c(cc1)ccc1Cl)N YUIYTAHPRXTDGF-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- DASHHCMDGVYWSH-LSLKUGRBSA-N CC(C(CN(CC1)C[C@H]1O)c(cc1)ccc1Cl)=O Chemical compound CC(C(CN(CC1)C[C@H]1O)c(cc1)ccc1Cl)=O DASHHCMDGVYWSH-LSLKUGRBSA-N 0.000 description 3
- PVPNMLQGACPPGM-UHFFFAOYSA-N CC(C(CN1CCCC1)c(cc1)ccc1Cl)=O Chemical compound CC(C(CN1CCCC1)c(cc1)ccc1Cl)=O PVPNMLQGACPPGM-UHFFFAOYSA-N 0.000 description 3
- XSHVROGZGRKCDZ-UHFFFAOYSA-N CC(C)NC(C1)C1(C[NH+](C)[O-])c(cc1)ccc1Cl Chemical compound CC(C)NC(C1)C1(C[NH+](C)[O-])c(cc1)ccc1Cl XSHVROGZGRKCDZ-UHFFFAOYSA-N 0.000 description 3
- VVOFMUSZUYTPOK-UHFFFAOYSA-N CC(C)NCC(C(C(C)=C)=O)(c(cc1)ccc1Cl)O Chemical compound CC(C)NCC(C(C(C)=C)=O)(c(cc1)ccc1Cl)O VVOFMUSZUYTPOK-UHFFFAOYSA-N 0.000 description 3
- KRSDAJKDGZOADN-UHFFFAOYSA-N CC(C)NCC(C(C)=O)c(cc1)ccc1F Chemical compound CC(C)NCC(C(C)=O)c(cc1)ccc1F KRSDAJKDGZOADN-UHFFFAOYSA-N 0.000 description 3
- XDLBGBLQVRNEJW-UHFFFAOYSA-N CC(C)NCC(C(N)=O)c(cc1)cc(F)c1F Chemical compound CC(C)NCC(C(N)=O)c(cc1)cc(F)c1F XDLBGBLQVRNEJW-UHFFFAOYSA-N 0.000 description 3
- DNAQFEUBMBDVSR-UHFFFAOYSA-N CC(C)NCC(C(N)=O)c(cc1)ccc1OC Chemical compound CC(C)NCC(C(N)=O)c(cc1)ccc1OC DNAQFEUBMBDVSR-UHFFFAOYSA-N 0.000 description 3
- MGFXAHFTLAKBRH-UHFFFAOYSA-N CC(C)NCC(C(N1CC1)=O)c(cc1)c(C)c(F)c1Cl Chemical compound CC(C)NCC(C(N1CC1)=O)c(cc1)c(C)c(F)c1Cl MGFXAHFTLAKBRH-UHFFFAOYSA-N 0.000 description 3
- GXTRJCYTCAROAS-UHFFFAOYSA-N CC(C)NCC(C(N1CC1)=O)c(cc1)ccc1Cl Chemical compound CC(C)NCC(C(N1CC1)=O)c(cc1)ccc1Cl GXTRJCYTCAROAS-UHFFFAOYSA-N 0.000 description 3
- DEXDQYQZKYQAQF-UHFFFAOYSA-N NC(C(CN(CC1)CCC1O)c(cc1)ccc1Cl)=O Chemical compound NC(C(CN(CC1)CCC1O)c(cc1)ccc1Cl)=O DEXDQYQZKYQAQF-UHFFFAOYSA-N 0.000 description 3
- 125000002393 azetidinyl group Chemical group 0.000 description 3
- XMNHYTVFSORYKH-UHFFFAOYSA-N CC(C(CC1(CC1)N(C)C)c(cc1)ccc1Cl)=O Chemical compound CC(C(CC1(CC1)N(C)C)c(cc1)ccc1Cl)=O XMNHYTVFSORYKH-UHFFFAOYSA-N 0.000 description 2
- AFNNDFNFOMRPSI-UHFFFAOYSA-N CC(C(CC1(CC1)N)c(cc1)ccc1Cl)=O Chemical compound CC(C(CC1(CC1)N)c(cc1)ccc1Cl)=O AFNNDFNFOMRPSI-UHFFFAOYSA-N 0.000 description 2
- CHIKWHCJOJMBFW-UHFFFAOYSA-N CC(C(CCN)c(cc1)ccc1Br)=O Chemical compound CC(C(CCN)c(cc1)ccc1Br)=O CHIKWHCJOJMBFW-UHFFFAOYSA-N 0.000 description 2
- FVNZUMZSHCJXOG-UHFFFAOYSA-N CC(C(Cc(cc1)ccc1Cl)C1(CC1)N)=O Chemical compound CC(C(Cc(cc1)ccc1Cl)C1(CC1)N)=O FVNZUMZSHCJXOG-UHFFFAOYSA-N 0.000 description 2
- GAFQXOOPISZEIU-UHFFFAOYSA-N CC(C)(CC(C(C)=O)c(cc1)ccc1F)N Chemical compound CC(C)(CC(C(C)=O)c(cc1)ccc1F)N GAFQXOOPISZEIU-UHFFFAOYSA-N 0.000 description 2
- CAICXYBBTBZAKS-UHFFFAOYSA-N CC(C)NCC(C(N(CC1)CCN1c1ncnc2c1C(C)OC2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NCC(C(N(CC1)CCN1c1ncnc2c1C(C)OC2)=O)c(cc1)ccc1Cl CAICXYBBTBZAKS-UHFFFAOYSA-N 0.000 description 2
- FGTBJDQJHUFZSB-UHFFFAOYSA-N CC(C1(CCNCC1)c(cc1)cc(F)c1Cl)=O Chemical compound CC(C1(CCNCC1)c(cc1)cc(F)c1Cl)=O FGTBJDQJHUFZSB-UHFFFAOYSA-N 0.000 description 2
- PRFRVPSGJHHMHG-UHFFFAOYSA-N CC(C1(CCNCC1)c(cc1)ccc1Cl)=O Chemical compound CC(C1(CCNCC1)c(cc1)ccc1Cl)=O PRFRVPSGJHHMHG-UHFFFAOYSA-N 0.000 description 2
- AFOVYKKGSJUFQA-UHFFFAOYSA-N CC(CCN)(C(NC)=O)c(cc1)ccc1Cl Chemical compound CC(CCN)(C(NC)=O)c(cc1)ccc1Cl AFOVYKKGSJUFQA-UHFFFAOYSA-N 0.000 description 2
- PIPMENIKBUTGQR-SNVBAGLBSA-N CC([C@@H](Cc(cc1)ccc1F)N)=O Chemical compound CC([C@@H](Cc(cc1)ccc1F)N)=O PIPMENIKBUTGQR-SNVBAGLBSA-N 0.000 description 2
- UKWPYCHZAPELGS-LLVKDONJSA-N CC([C@@H](Cc(cc1)ccc1OC)N)=O Chemical compound CC([C@@H](Cc(cc1)ccc1OC)N)=O UKWPYCHZAPELGS-LLVKDONJSA-N 0.000 description 2
- SANCTMWYECMLCR-UHFFFAOYSA-N CC1OCc2c1c(N(CC1)CCN1C(C(CC(C)(C)N)c(cc1F)ccc1Cl)=O)ncn2 Chemical compound CC1OCc2c1c(N(CC1)CCN1C(C(CC(C)(C)N)c(cc1F)ccc1Cl)=O)ncn2 SANCTMWYECMLCR-UHFFFAOYSA-N 0.000 description 2
- RBXFUWLZNZOTBN-UHFFFAOYSA-O CCC(C(CC(C)(C)[NH3+])c(cc1)cc(F)c1Cl)=O Chemical compound CCC(C(CC(C)(C)[NH3+])c(cc1)cc(F)c1Cl)=O RBXFUWLZNZOTBN-UHFFFAOYSA-O 0.000 description 2
- RIGDNGRCTWXWFW-MRJYIUEKSA-N CCC(C(CN[C@H](CC1)CC[C@@H]1O)c(cc1)ccc1Cl)=O Chemical compound CCC(C(CN[C@H](CC1)CC[C@@H]1O)c(cc1)ccc1Cl)=O RIGDNGRCTWXWFW-MRJYIUEKSA-N 0.000 description 2
- PNXREAUYPTXQHE-MRVPVSSYSA-N CCC([C@H](CN)c(cc1)cc(Cl)c1Cl)=O Chemical compound CCC([C@H](CN)c(cc1)cc(Cl)c1Cl)=O PNXREAUYPTXQHE-MRVPVSSYSA-N 0.000 description 2
- QPILAAUEILBAAN-VHSXEESVSA-N CCC([C@H](CNC1)[C@@H]1c(cc1)cc(Cl)c1Cl)=O Chemical compound CCC([C@H](CNC1)[C@@H]1c(cc1)cc(Cl)c1Cl)=O QPILAAUEILBAAN-VHSXEESVSA-N 0.000 description 2
- ROQQOZZRWJKYNO-TVKKRMFBSA-N CCCC([C@@H](CC1c2ccccc2NC1)N)=O Chemical compound CCCC([C@@H](CC1c2ccccc2NC1)N)=O ROQQOZZRWJKYNO-TVKKRMFBSA-N 0.000 description 2
- BIJHQFODGCREMQ-UHFFFAOYSA-N CNCC(C(CCN)=O)c(cc1)ccc1F Chemical compound CNCC(C(CCN)=O)c(cc1)ccc1F BIJHQFODGCREMQ-UHFFFAOYSA-N 0.000 description 2
- RUPAHVODHKPLTA-YCQNMSHMSA-N C[C@H]([C@@H](C)NCC(C(CN)=O)c(cc1)ccc1Cl)c1ccccc1 Chemical compound C[C@H]([C@@H](C)NCC(C(CN)=O)c(cc1)ccc1Cl)c1ccccc1 RUPAHVODHKPLTA-YCQNMSHMSA-N 0.000 description 2
- LBASRDAUCBGBOV-LHIURRSHSA-N NCCC([C@H](CN)C1C=CC(Cl)=CC1)=O Chemical compound NCCC([C@H](CN)C1C=CC(Cl)=CC1)=O LBASRDAUCBGBOV-LHIURRSHSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- HOXWESKAHYABGO-UHFFFAOYSA-N C(C1)C11CNCC1 Chemical compound C(C1)C11CNCC1 HOXWESKAHYABGO-UHFFFAOYSA-N 0.000 description 1
- QVUNMWQRCFABKL-UHFFFAOYSA-N CC(C)N(CCC1)CC1O Chemical compound CC(C)N(CCC1)CC1O QVUNMWQRCFABKL-UHFFFAOYSA-N 0.000 description 1
- LCBCTCBNOSWKLT-VIBJYCFESA-N CC(C)NC(C1)C1(C(N(CC1)CCN1c1ncnc2c1[C@@H](C)OC2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC(C1)C1(C(N(CC1)CCN1c1ncnc2c1[C@@H](C)OC2)=O)c(cc1)ccc1Cl LCBCTCBNOSWKLT-VIBJYCFESA-N 0.000 description 1
- LCBCTCBNOSWKLT-PJLCYBKHSA-N CC(C)NC(C1)C1(C(N(CC1)CCN1c1ncnc2c1[C@H](C)OC2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC(C1)C1(C(N(CC1)CCN1c1ncnc2c1[C@H](C)OC2)=O)c(cc1)ccc1Cl LCBCTCBNOSWKLT-PJLCYBKHSA-N 0.000 description 1
- LUEQQXVSHKNKFD-UHFFFAOYSA-N CC(C)NCC(C(N(CC1)CCN1c1ncnc2c1CCCOC2)=O)c(ccc(Cl)c1)c1Cl Chemical compound CC(C)NCC(C(N(CC1)CCN1c1ncnc2c1CCCOC2)=O)c(ccc(Cl)c1)c1Cl LUEQQXVSHKNKFD-UHFFFAOYSA-N 0.000 description 1
- JIARQKROKMAXCP-DIMJTDRSSA-N CC(C)NCC(C(N(CC1)CCN1c1ncnc2c1[C@H](C)OC2)=O)c(cc1)ccc1OC Chemical compound CC(C)NCC(C(N(CC1)CCN1c1ncnc2c1[C@H](C)OC2)=O)c(cc1)ccc1OC JIARQKROKMAXCP-DIMJTDRSSA-N 0.000 description 1
- CAICXYBBTBZAKS-APWZRJJASA-N CC(C)NC[C@H](C(N(CC1)CCN1c1ncnc2c1[C@@H](C)OC2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@H](C(N(CC1)CCN1c1ncnc2c1[C@@H](C)OC2)=O)c(cc1)ccc1Cl CAICXYBBTBZAKS-APWZRJJASA-N 0.000 description 1
- SSDARPKYBOXNEQ-UHFFFAOYSA-N CC1OCc2c1c(N(CC1)CCN1C(CCc(cc1)ccc1Cl)=O)ncn2 Chemical compound CC1OCc2c1c(N(CC1)CCN1C(CCc(cc1)ccc1Cl)=O)ncn2 SSDARPKYBOXNEQ-UHFFFAOYSA-N 0.000 description 1
- MSGDINAGVZKNRI-FQNRMIAFSA-N CC1OCc2c1c(N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)ncn2 Chemical compound CC1OCc2c1c(N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)ncn2 MSGDINAGVZKNRI-FQNRMIAFSA-N 0.000 description 1
- LFMUUVFNGKDTTJ-DHLRTPTCSA-N CC1OCc2c1c(N(CC1)[C@@H](C)CN1C(C(C1)c(cc3)cc(F)c3Cl)=[O]C1(C)N)ncn2 Chemical compound CC1OCc2c1c(N(CC1)[C@@H](C)CN1C(C(C1)c(cc3)cc(F)c3Cl)=[O]C1(C)N)ncn2 LFMUUVFNGKDTTJ-DHLRTPTCSA-N 0.000 description 1
- WGTXUIAXPIFQAY-BHVXPOTESA-N CC1OCc2c1c(N(CC1)[C@@H](C)CN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)ncn2 Chemical compound CC1OCc2c1c(N(CC1)[C@@H](C)CN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)ncn2 WGTXUIAXPIFQAY-BHVXPOTESA-N 0.000 description 1
- HUSGIMGPSCQRKA-UHFFFAOYSA-N CN(CC1)CC1(F)F Chemical compound CN(CC1)CC1(F)F HUSGIMGPSCQRKA-UHFFFAOYSA-N 0.000 description 1
- ZAMXVCJJAQXCBT-UHFFFAOYSA-N CN(CC1)CC1F Chemical compound CN(CC1)CC1F ZAMXVCJJAQXCBT-UHFFFAOYSA-N 0.000 description 1
- FLVFPAIGVBQGET-UHFFFAOYSA-N CN(CC1)CC1O Chemical compound CN(CC1)CC1O FLVFPAIGVBQGET-UHFFFAOYSA-N 0.000 description 1
- LFHMKODCPPOLIB-UHFFFAOYSA-N CN(CC1)CCC1(F)F Chemical compound CN(CC1)CCC1(F)F LFHMKODCPPOLIB-UHFFFAOYSA-N 0.000 description 1
- ZAMXVCJJAQXCBT-YFKPBYRVSA-N CN(CC1)C[C@H]1F Chemical compound CN(CC1)C[C@H]1F ZAMXVCJJAQXCBT-YFKPBYRVSA-N 0.000 description 1
- KJCIMSSFGUGTGA-UHFFFAOYSA-N CN(CCNC1)C1=O Chemical compound CN(CCNC1)C1=O KJCIMSSFGUGTGA-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N CN1CCCC1 Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- QKKJCMRCGNAZNM-UHFFFAOYSA-N CN1CCN(CC(F)(F)F)CC1 Chemical compound CN1CCN(CC(F)(F)F)CC1 QKKJCMRCGNAZNM-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N CN1CCNCC1 Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N CN1CCOCC1 Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- KDTVWEHAAISPNW-UHFFFAOYSA-N CN1CCSCC1 Chemical compound CN1CCSCC1 KDTVWEHAAISPNW-UHFFFAOYSA-N 0.000 description 1
- FTRIMUQPAHULKM-ZDUSSCGKSA-N C[C@@H]1OCc2c1c(N(CC1)CCN1C(Cc(cc1)ccc1Cl)=O)ncn2 Chemical compound C[C@@H]1OCc2c1c(N(CC1)CCN1C(Cc(cc1)ccc1Cl)=O)ncn2 FTRIMUQPAHULKM-ZDUSSCGKSA-N 0.000 description 1
- MSGDINAGVZKNRI-XJKSGUPXSA-N C[C@@H]1OCc2c1c(N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)ncn2 Chemical compound C[C@@H]1OCc2c1c(N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)ncn2 MSGDINAGVZKNRI-XJKSGUPXSA-N 0.000 description 1
- HXSCPHYWMQJKOS-XJKSGUPXSA-N C[C@@H]1OCc2c1c(N(CC1)CCN1C([C@H](CN)c(cc1)ccc1Cl)=O)ncn2 Chemical compound C[C@@H]1OCc2c1c(N(CC1)CCN1C([C@H](CN)c(cc1)ccc1Cl)=O)ncn2 HXSCPHYWMQJKOS-XJKSGUPXSA-N 0.000 description 1
- KIQAIKMRGPCOSD-YSPPHNQVSA-N C[C@H](Cc(cc1)ccc1Cl)C(N(CC1)C[C@H](C)N1c1ncnc2c1C(C)OC2)=O Chemical compound C[C@H](Cc(cc1)ccc1Cl)C(N(CC1)C[C@H](C)N1c1ncnc2c1C(C)OC2)=O KIQAIKMRGPCOSD-YSPPHNQVSA-N 0.000 description 1
- DLNKOYKMWOXYQA-VXNVDRBHSA-N C[C@H]([C@H](c1ccccc1)O)N Chemical compound C[C@H]([C@H](c1ccccc1)O)N DLNKOYKMWOXYQA-VXNVDRBHSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- QUHVRXKSQHIZNV-UHFFFAOYSA-N FC1(CNC1)F Chemical compound FC1(CNC1)F QUHVRXKSQHIZNV-UHFFFAOYSA-N 0.000 description 1
- UOGQPXQDNUHUIB-UHFFFAOYSA-N FC1(CNCCC1)F Chemical compound FC1(CNCCC1)F UOGQPXQDNUHUIB-UHFFFAOYSA-N 0.000 description 1
- IMLXLGZJLAOKJN-IZLXSQMJSA-N N[C@H](CC1)CC[C@@H]1O Chemical compound N[C@H](CC1)CC[C@@H]1O IMLXLGZJLAOKJN-IZLXSQMJSA-N 0.000 description 1
- QPIKLTPKEPWVNL-UHFFFAOYSA-N O=C(C1(CNCC1)c(cc1)ccc1Cl)N(CC1)CCN1c1ncnc2c1CCCOC2 Chemical compound O=C(C1(CNCC1)c(cc1)ccc1Cl)N(CC1)CCN1c1ncnc2c1CCCOC2 QPIKLTPKEPWVNL-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N OC1CCNCC1 Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-BYPYZUCNSA-N O[C@@H]1CNCC1 Chemical compound O[C@@H]1CNCC1 JHHZLHWJQPUNKB-BYPYZUCNSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- MOZRQQTUYAYCQT-FQEVSTJZSA-N n-[[(3s)-3-amino-1-(5-ethyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl]methyl]-2,4-difluorobenzamide Chemical group C([C@]1(CCN(C1)C=1N=CN=C2NC=C(C=12)CC)N)NC(=O)C1=CC=C(F)C=C1F MOZRQQTUYAYCQT-FQEVSTJZSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81880706P | 2006-07-06 | 2006-07-06 | |
| US60/818,807 | 2006-07-06 | ||
| PCT/US2007/072863 WO2008006025A1 (en) | 2006-07-06 | 2007-07-05 | Dihydrofuro pyrimidines as akt protein kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009542720A JP2009542720A (ja) | 2009-12-03 |
| JP2009542720A5 true JP2009542720A5 (enExample) | 2010-08-26 |
| JP5231410B2 JP5231410B2 (ja) | 2013-07-10 |
Family
ID=38603508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009518629A Active JP5231410B2 (ja) | 2006-07-06 | 2007-07-05 | Ａｋｔプロテインキナーゼ阻害剤としてのジヒドロフロピリミジン |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8329701B2 (enExample) |
| EP (1) | EP2049546B1 (enExample) |
| JP (1) | JP5231410B2 (enExample) |
| CN (1) | CN101511842B (enExample) |
| AT (1) | ATE493418T1 (enExample) |
| CA (1) | CA2656566C (enExample) |
| DE (1) | DE602007011628D1 (enExample) |
| WO (1) | WO2008006025A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| EP2054418B1 (en) | 2006-07-06 | 2011-11-09 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| AR067413A1 (es) * | 2007-07-05 | 2009-10-07 | Genentech Inc | Compuestos heterociclicos que contienen ciclopenta[d]pirimidina inhibidores de proteinquinasas akt, composiciones farmaceuticas que los contienen, metodo de preparacion y uso de las mismas para el tratamiento de enfermedades hiperproliferativas, tales como cancer |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| US8841304B2 (en) | 2008-01-08 | 2014-09-23 | Array Biopharma, Inc. | Pyrrolopyridines as kinase inhibitors |
| MX2010007546A (es) * | 2008-01-09 | 2010-09-30 | Array Biopharma Inc | Pirimidil ciclopentanos hidroxilados en forma de inhibidores de akt proteína quinasa. |
| ES2392014T3 (es) | 2008-01-09 | 2012-12-03 | Array Biopharma, Inc. | Pirazolopiridinas como inhibidores de la cinasa |
| CA2711782C (en) | 2008-01-09 | 2017-01-03 | Array Biopharma Inc. | 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors |
| UA101676C2 (uk) | 2008-07-31 | 2013-04-25 | Дженентек, Инк. | Піримідинові сполуки, композиції і способи застосування |
| KR101447789B1 (ko) | 2009-11-12 | 2014-10-06 | 에프. 호프만-라 로슈 아게 | Ｎ-7 치환된 퓨린 및 피라졸로피리미딘 화합물, 조성물 및 사용 방법 |
| MX2012005463A (es) | 2009-11-12 | 2012-09-12 | Hoffmann La Roche | Compuestos de purina n/9 sustituida, composiciones y metodos de uso. |
| CA2938626A1 (en) | 2013-07-26 | 2015-01-29 | John Rothman | Compositions to improve the therapeutic benefit of bisantrene |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| PL3919491T3 (pl) | 2019-01-29 | 2025-10-20 | Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. | Inhibitor akt |
| CN115485276B (zh) * | 2020-05-15 | 2024-05-31 | 南京正大天晴制药有限公司 | 氘代akt激酶抑制剂 |
| WO2022017449A1 (zh) | 2020-07-22 | 2022-01-27 | 南京正大天晴制药有限公司 | 一种二氢吡啶并[2,3-d]嘧啶酮衍生物的盐、其制备方法及用途 |
| CA3186565A1 (en) * | 2020-07-22 | 2022-01-27 | Lei Miao | Unit dosage composition of akt inhibitor |
Family Cites Families (87)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3885035A (en) | 1972-04-05 | 1975-05-20 | Sandoz Ag | Method for treating arrhythmia by using 1,4-bis(4 quinazolinyl) piperazines |
| US3956495A (en) | 1973-10-30 | 1976-05-11 | Eli Lilly And Company | 2,4-Diaminoquinazolines as antithrombotic agents |
| US3966936A (en) | 1974-02-21 | 1976-06-29 | Pfizer Inc. | Piperazino quinazoline bronchodilators |
| US4060615A (en) | 1976-02-18 | 1977-11-29 | Mead Johnson & Company | 2-Piperazinyl-6,7-dimethoxyquinazolines |
| JPS562968A (en) | 1979-06-21 | 1981-01-13 | Mitsubishi Yuka Yakuhin Kk | Novel pyrimidine derivative |
| US4749704A (en) | 1985-03-07 | 1988-06-07 | Sankyo Company Limited | Cyclopenta[d]pyrimidine derivatives and use as antidepressants |
| WO1987004928A1 (fr) * | 1986-02-24 | 1987-08-27 | Mitsui Petrochemical Industries, Ltd. | Agents therapeutiques de la neuropathie |
| WO1990007926A1 (en) | 1989-01-20 | 1990-07-26 | Pfizer Inc. | 3-(1,2,5,6-tetrahydropyridyl)-pyrrolopyridines |
| PT664291E (pt) | 1992-10-05 | 2000-11-30 | Ube Industries | Composto de pirimidina |
| EP0710654A4 (en) | 1993-07-23 | 1996-08-28 | Green Cross Corp | TRIAZOLE DERIVATIVE AND ITS PHARMACEUTICAL USE |
| GB9416189D0 (en) | 1994-08-10 | 1994-09-28 | Merck Sharp & Dohme | Therapeutic agents |
| CN1102144C (zh) | 1994-08-13 | 2003-02-26 | 株式会社柳韩洋行 | 新的嘧啶衍生物及其制备方法 |
| US5525625A (en) | 1995-01-24 | 1996-06-11 | Warner-Lambert Company | 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders |
| US7125880B1 (en) | 1995-06-06 | 2006-10-24 | Pfizer Inc. | Corticotropin releasing factor antagonists |
| ZA979961B (en) | 1996-11-15 | 1999-05-05 | Lilly Co Eli | 5-HT1F agonists |
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| US6506798B1 (en) | 1997-07-01 | 2003-01-14 | Warner-Lambert Company | 4-Arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective MEK inhibitors |
| NZ501277A (en) | 1997-07-01 | 2002-12-20 | Warner Lambert Co | -2(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as MEK inhibitors |
| US6821963B2 (en) | 1997-07-01 | 2004-11-23 | Warner-Lambert Company | 4-Bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors |
| US6310060B1 (en) | 1998-06-24 | 2001-10-30 | Warner-Lambert Company | 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as MEK inhibitors |
| IL132840A (en) | 1997-07-01 | 2004-12-15 | Warner Lambert Co | Derivatives 4 - bromo or 4 - benzohydroxamic acid iodine amino iodine and pharmaceutical preparations containing them for use as MEK inhibitors |
| ES2356886T3 (es) | 1998-03-31 | 2011-04-14 | Kyowa Hakko Kirin Co., Ltd. | Compuestos heterocíclicos nitrogenados. |
| DE19853278A1 (de) | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| EP1140062B1 (en) | 1999-01-07 | 2005-04-06 | Warner-Lambert Company LLC | Treatment of asthma with mek inhibitors |
| IL144103A0 (en) | 1999-01-07 | 2002-05-23 | Warner Lambert Co | Antiviral method using mek inhibitors |
| CA2348236A1 (en) | 1999-01-13 | 2000-07-20 | Stephen Douglas Barrett | 4-arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective mek inhibitors |
| AU2201500A (en) | 1999-01-13 | 2000-08-01 | Warner-Lambert Company | Benzenesulfonamide derivatives and their use as mek inhibitors |
| JP2002534497A (ja) | 1999-01-13 | 2002-10-15 | ワーナー−ランバート・カンパニー | スルホヒドロキサム酸およびスルホヒドロキサメートおよびｍｅｋ阻害剤としてのその使用 |
| WO2000041505A2 (en) | 1999-01-13 | 2000-07-20 | Warner-Lambert Company | Anthranilic acid derivatives |
| AU2482700A (en) | 1999-01-13 | 2000-08-01 | Warner-Lambert Company | 1-heterocycle substituted diarylamines |
| HRP20010524A2 (en) | 1999-01-13 | 2002-08-31 | Warner Lambert Co | Benzoheterocycles and their use as mek inhibitors |
| GB9910577D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| CA2377092A1 (en) | 1999-07-16 | 2001-01-25 | Warner-Lambert Company | Method for treating chronic pain using mek inhibitors |
| CN1373660A (zh) | 1999-07-16 | 2002-10-09 | 沃尼尔·朗伯公司 | 使用mek抑制剂治疗慢性疼痛的方法 |
| CN1365277A (zh) | 1999-07-16 | 2002-08-21 | 沃尼尔·朗伯公司 | 使用mek抑制剂治疗慢性疼痛的方法 |
| KR20020015379A (ko) | 1999-07-16 | 2002-02-27 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | 엠이케이 억제제를 사용하는 만성 동통의 치료방법 |
| CA2403017A1 (en) | 2000-03-15 | 2001-09-20 | Warner-Lambert Company | 5-amide substituted diarylamines as mex inhibitors |
| CA2416685C (en) | 2000-07-19 | 2008-10-07 | Warner-Lambert Company | Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids |
| JP2004507518A (ja) | 2000-08-25 | 2004-03-11 | ワーナー−ランバート・カンパニー・エルエルシー | Ｎ−アリール−アントラニル酸及びその誘導体の製造法 |
| WO2002044166A1 (en) | 2000-11-02 | 2002-06-06 | Astrazeneca Ab | Substituted quinolines as antitumor agents |
| JP2004532838A (ja) * | 2001-03-02 | 2004-10-28 | ブリストル−マイヤーズ スクイブ カンパニー | メラノコルチン受容体のモデュレーターとして有用な化合物及びそれを含む製薬組成物 |
| WO2002083139A1 (en) | 2001-04-10 | 2002-10-24 | Merck & Co., Inc. | Inhibitors of akt activity |
| CA2446514A1 (en) | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Fused pyrimidines as antagonists of the corticotropin releasing factor (crf) |
| US7115741B2 (en) | 2001-09-06 | 2006-10-03 | Levy Daniel E | 4-thieno[2,3-D]pyrimidin-4-YL piperazine compounds |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| TW200306819A (en) | 2002-01-25 | 2003-12-01 | Vertex Pharma | Indazole compounds useful as protein kinase inhibitors |
| US7235537B2 (en) | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| DE60330227D1 (de) | 2002-03-13 | 2010-01-07 | Array Biopharma Inc | N3-alkylierte benzimidazol-derivate als mek-hemmer |
| RU2300528C2 (ru) | 2002-03-13 | 2007-06-10 | Эррэй Биофарма, Инк. | N3-алкилированные бензимидазольные производные в качестве ингибиторов мек |
| AU2003226250B2 (en) | 2002-04-08 | 2007-08-16 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| CA2480800C (en) | 2002-04-08 | 2008-09-23 | Mark T. Bilodeau | Inhibitors of akt activity |
| EP1496906A4 (en) | 2002-04-08 | 2006-05-03 | Merck & Co Inc | HEMMER OF ACT ACTIVITY |
| EP1494676B1 (en) | 2002-04-08 | 2013-05-08 | Merck Sharp & Dohme Corp. | Fused quinoxaline derivatives as inhibitors of akt activity |
| AU2003230367A1 (en) | 2002-05-10 | 2003-11-11 | Neurocrine Biosciences, Inc. | Substituted piperazine as melanocortin receptors ligands |
| US20040102360A1 (en) | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| CA2501365C (en) | 2002-10-30 | 2011-05-31 | Merck & Co., Inc. | Inhibitors of akt activity |
| GB0308208D0 (en) | 2003-04-09 | 2003-05-14 | Glaxo Group Ltd | Chemical compounds |
| CN1809351A (zh) | 2003-04-24 | 2006-07-26 | 麦克公司 | Akt活性抑制剂 |
| EP1646615B1 (en) | 2003-06-06 | 2009-08-26 | Vertex Pharmaceuticals Incorporated | Pyrimidine derivatives as modulators of atp-binding cassette transporters |
| AR045445A1 (es) | 2003-08-05 | 2005-10-26 | Vertex Pharma | Compuestos ihinibidores de canales ionicos regulados por voltaje |
| CA2534785A1 (en) | 2003-08-12 | 2005-02-17 | Robin Douglas Clark | Tetrahydroquinazoline derivatives as cfr antagonists |
| US20070027156A1 (en) | 2003-09-09 | 2007-02-01 | Hisao Nakai | Crf antagonists and heterobicyclic compounds |
| WO2005039564A1 (en) | 2003-10-02 | 2005-05-06 | Vertex Pharmaceuticals Incorporated | Phthalimide compounds useful as protein kinase inhibitors |
| EP1684694A2 (en) | 2003-11-21 | 2006-08-02 | Array Biopharma, Inc. | Akt protein kinase inhibitors |
| JP5213229B2 (ja) | 2004-04-23 | 2013-06-19 | エグゼリクシス， インコーポレイテッド | キナーゼ調節因子および使用方法 |
| US20060025074A1 (en) | 2004-07-30 | 2006-02-02 | Chih-Ming Liang | Bluetooth-based headset |
| ES2368930T3 (es) | 2004-09-06 | 2011-11-23 | Bayer Pharma Aktiengesellschaft | Pirazolopirimidinas como inhibidores de proteína cinasa b (akt). |
| TWM266655U (en) | 2004-09-23 | 2005-06-01 | Blueexpert Technology Corp | Bluetooth earphone device capable of wirelessly receiving and transmitting stereo sound signal and digital information signal |
| TW200621257A (en) * | 2004-10-20 | 2006-07-01 | Astellas Pharma Inc | Pyrimidine derivative fused with nonaromatic ring |
| UY29177A1 (es) | 2004-10-25 | 2006-05-31 | Astex Therapeutics Ltd | Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos |
| JP5274842B2 (ja) | 2004-12-28 | 2013-08-28 | エグゼリクシス， インコーポレイテッド | 免疫疾患、炎症疾患および増殖疾患の処置のためのセリン−スレオニンキナーゼモジュレーター（ｐ７０Ｓ６Ｋ、Ａｋｔ−１およびＡｋｔ−２）としての［１Ｈ−ピペラゾ［３，４−ｄ］ピリミジン−４−イル］−ピペラジンまたは［１Ｈ−ピペラゾ［３，４−ｄ］ピリミジン−４−イル］−ピペラジン化合物 |
| US20090111805A1 (en) | 2005-02-24 | 2009-04-30 | Pfizer Inc. | Bicyclic heteroaromatic derivatives useful as anticancer agents |
| NZ564065A (en) | 2005-05-20 | 2011-03-31 | Vertex Pharma | Pyrrolopyridines useful as inhibitors of protein kinase |
| UY29610A1 (es) | 2005-06-21 | 2007-01-31 | Cancer Rec Tech Ltd | Aril-alquilaminas y heteroaril-alquilaminas como inhibidores de la quinasa proteínica |
| KR100670171B1 (ko) * | 2005-06-25 | 2007-01-17 | 한국과학기술연구원 | 신규 퓨로[２,３-ｄ]피리미딘계 Ａｋｔ1 키나아제 저해제,그 제조 중간체 및 이들의 제조 방법 |
| AR056691A1 (es) | 2005-10-13 | 2007-10-17 | Glaxo Group Ltd | Derivados pirrolopirimidina como inhibidores de syk |
| CA2635541A1 (en) | 2005-12-28 | 2007-07-12 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds and their use as mineralocorticoid receptor ligands |
| JP2009534454A (ja) | 2006-04-25 | 2009-09-24 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| RU2008152171A (ru) | 2006-07-05 | 2010-08-10 | Интермьюн, Инк. (Us) | Новые ингибиторы вирусной репликации гепатита с |
| TW200808325A (en) | 2006-07-06 | 2008-02-16 | Astrazeneca Ab | Novel compounds |
| EP2054418B1 (en) * | 2006-07-06 | 2011-11-09 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| CA2656618C (en) * | 2006-07-06 | 2014-08-26 | Array Biopharma Inc. | Cyclopenta [d] pyrimidines as akt protein kinase inhibitors |
| UA95641C2 (xx) * | 2006-07-06 | 2011-08-25 | Эррей Биофарма Инк. | Гідроксильовані піримідильні циклопентани як інгібітори акт протеїнкінази$гидроксилированные пиримидильные циклопентаны как ингибиторы акт протеинкиназы |
| US7718693B2 (en) | 2006-07-06 | 2010-05-18 | Glaxo Group Limited | Receptor antagonists and their methods of use |
| US7910747B2 (en) | 2006-07-06 | 2011-03-22 | Bristol-Myers Squibb Company | Phosphonate and phosphinate pyrazolylamide glucokinase activators |
| GB0613518D0 (en) | 2006-07-06 | 2006-08-16 | Phytopharm Plc | Chemical compounds |
| WO2008012635A2 (en) | 2006-07-26 | 2008-01-31 | Pfizer Products Inc. | Amine derivatives useful as anticancer agents |
-
2007
- 2007-07-05 DE DE602007011628T patent/DE602007011628D1/de active Active
- 2007-07-05 CA CA2656566A patent/CA2656566C/en not_active Expired - Fee Related
- 2007-07-05 AT AT07799326T patent/ATE493418T1/de not_active IP Right Cessation
- 2007-07-05 WO PCT/US2007/072863 patent/WO2008006025A1/en not_active Ceased
- 2007-07-05 JP JP2009518629A patent/JP5231410B2/ja active Active
- 2007-07-05 EP EP07799326A patent/EP2049546B1/en active Active
- 2007-07-05 CN CN2007800330476A patent/CN101511842B/zh not_active Expired - Fee Related
- 2007-07-05 US US12/307,537 patent/US8329701B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009542720A5 (enExample) | ||
| JP2009542722A5 (enExample) | ||
| RU2478632C2 (ru) | Гидроксилированные и метоксилированные циклопента[d]пиримидины в качестве ингибиторов акт протеинкиназ | |
| JP2009542723A5 (enExample) | ||
| CN113614080A (zh) | Kras g12c抑制剂化合物及其用途 | |
| RU2009103899A (ru) | Циклопента(d)пиримидины в качестве ингибиторов протеинкиназ | |
| JP2010533715A5 (enExample) | ||
| ES2249270T3 (es) | Derivados de 3(5)-aminopirazol, procedimiento para su preparacion y su uso como agentes antitumorales. | |
| RU2359967C2 (ru) | Производные тиофена и фармацевтическая композиция (варианты) | |
| AP1122A (en) | Therapeutically active compounds based on based on based on indazole bioisostere replacement of catechol in PDE4 inhibitors. | |
| ES2411655T3 (es) | Derivados de aminoindazol activos como inhibidores de quinasas, procedimiento para su preparación y composiciones farmacéuticas que los comprenden | |
| CN101636397B (zh) | 脲类化合物、其制备方法及其医药用途 | |
| JP2005533024A (ja) | Ｐｄｅ４阻害剤としてのピリダジン−３（２ｈ）−オン誘導体 | |
| ZA200406730B (en) | Indazole substituted with an anti-cancerous activity. | |
| JP2009542721A5 (enExample) | ||
| RU2366657C2 (ru) | Производные n-(1,5-дифенил-1н-пиразол-3-ил)сульфонамида со сродством к рецепторам cb1 | |
| RU2005137403A (ru) | Новые замещенные 3-сера-индолы | |
| JP2005533024A5 (enExample) | ||
| JP2017525757A5 (enExample) | ||
| EA006583B1 (ru) | Производные азетидина, способ их получения и содержащие их фармацевтические композиции | |
| RU2008109654A (ru) | Производные бензохиназолина и их применение для лечения костных нарушений | |
| RU2009110183A (ru) | Производные 4-замещенной феноксифенилуксусной кислоты | |
| WO2004083167A1 (ja) | スルファミド誘導体及びその医薬組成物 | |
| AU2014279113A1 (en) | 4-alkynyl imidazole derivative and medicine comprising same as active ingredient | |
| US20060264493A1 (en) | Tetracyclic pyrazole derivatives as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |