JP2017527548A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017527548A5 JP2017527548A5 JP2017507807A JP2017507807A JP2017527548A5 JP 2017527548 A5 JP2017527548 A5 JP 2017527548A5 JP 2017507807 A JP2017507807 A JP 2017507807A JP 2017507807 A JP2017507807 A JP 2017507807A JP 2017527548 A5 JP2017527548 A5 JP 2017527548A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- amine
- isoxazolo
- optionally substituted
- nhr
- 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
- 125000003107 substituted aryl group Chemical group 0.000 claims 35
- 229910052757 nitrogen Inorganic materials 0.000 claims 27
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 9
- XEYWCHKONZUDGB-UHFFFAOYSA-N 5-chloro-4,6-dimethyl-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound CC1=C(Cl)C(C)=NC2=C1C(N)=NO2 XEYWCHKONZUDGB-UHFFFAOYSA-N 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- GIBMCZLVZLKVQG-UHFFFAOYSA-N BrC=1C(=C2C(=NC=1C)ON=C2N)C Chemical compound BrC=1C(=C2C(=NC=1C)ON=C2N)C GIBMCZLVZLKVQG-UHFFFAOYSA-N 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- NIHLEQFZWNKMEY-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound C1=CC=C2C(N)=NOC2=N1 NIHLEQFZWNKMEY-UHFFFAOYSA-N 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 5
- DYMSNXTUZQZFSM-UHFFFAOYSA-N 4,6-dimethyl-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound CC1=CC(C)=C2C(N)=NOC2=N1 DYMSNXTUZQZFSM-UHFFFAOYSA-N 0.000 claims 4
- GYVPSYJDRWKPPV-UHFFFAOYSA-N 5-chloro-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound C1=C(Cl)C=C2C(N)=NOC2=N1 GYVPSYJDRWKPPV-UHFFFAOYSA-N 0.000 claims 4
- PDKYYNMMWLZHAR-UHFFFAOYSA-N C(C)(C)C1=CC=C2C(=N1)ON=C2N Chemical compound C(C)(C)C1=CC=C2C(=N1)ON=C2N PDKYYNMMWLZHAR-UHFFFAOYSA-N 0.000 claims 4
- KRJAAEYJGMMGBQ-UHFFFAOYSA-N C1(=CC=CC=C1)C1(C=CC=2C(=N1)ONC=2N)N Chemical compound C1(=CC=CC=C1)C1(C=CC=2C(=N1)ONC=2N)N KRJAAEYJGMMGBQ-UHFFFAOYSA-N 0.000 claims 4
- RQYGWIFUAGWQTQ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C2C(=NC=C1)ON=C2N Chemical compound C1(=CC=CC=C1)C1=C2C(=NC=C1)ON=C2N RQYGWIFUAGWQTQ-UHFFFAOYSA-N 0.000 claims 4
- ZSBNCQKXLKCXMV-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=C2C(=N1)ON=C2N Chemical compound C1(=CC=CC=C1)C1=CC=C2C(=N1)ON=C2N ZSBNCQKXLKCXMV-UHFFFAOYSA-N 0.000 claims 4
- ZTJREVULHHQPON-UHFFFAOYSA-N CC1(C=CC=2C(=N1)ONC=2N)NC Chemical compound CC1(C=CC=2C(=N1)ONC=2N)NC ZTJREVULHHQPON-UHFFFAOYSA-N 0.000 claims 4
- YRKCJEOMIIYMAZ-UHFFFAOYSA-N CC1(CC=2C=C3C(=NC=2CC1)ON=C3N)C Chemical compound CC1(CC=2C=C3C(=NC=2CC1)ON=C3N)C YRKCJEOMIIYMAZ-UHFFFAOYSA-N 0.000 claims 4
- IRLDKYAHPPZKEM-UHFFFAOYSA-N CC1=C2C(=NC(=C1C)C)ON=C2N Chemical compound CC1=C2C(=NC(=C1C)C)ON=C2N IRLDKYAHPPZKEM-UHFFFAOYSA-N 0.000 claims 4
- XQBXFFNKIPGUJX-UHFFFAOYSA-N CC1=CC(=C2C(=N1)ON=C2N)C(F)(F)F Chemical compound CC1=CC(=C2C(=N1)ON=C2N)C(F)(F)F XQBXFFNKIPGUJX-UHFFFAOYSA-N 0.000 claims 4
- NBKLMRMGMSDYOZ-UHFFFAOYSA-N CC=1C=C2C(=NC=1)ON=C2N Chemical compound CC=1C=C2C(=NC=1)ON=C2N NBKLMRMGMSDYOZ-UHFFFAOYSA-N 0.000 claims 4
- ANEPQTAUFJDZSB-UHFFFAOYSA-N CC=1C=C2C(=NC=1C)ON=C2N Chemical compound CC=1C=C2C(=NC=1C)ON=C2N ANEPQTAUFJDZSB-UHFFFAOYSA-N 0.000 claims 4
- ZUOFIOIZPVAMAG-UHFFFAOYSA-N CN(CCCOC1=CC=C2C(=N1)ON=C2N)C Chemical compound CN(CCCOC1=CC=C2C(=N1)ON=C2N)C ZUOFIOIZPVAMAG-UHFFFAOYSA-N 0.000 claims 4
- AXDAHCXGMJSBOW-UHFFFAOYSA-N CN(CCOC1=CC=C2C(=N1)ON=C2N)C Chemical compound CN(CCOC1=CC=C2C(=N1)ON=C2N)C AXDAHCXGMJSBOW-UHFFFAOYSA-N 0.000 claims 4
- KUTMWJSWDFIUMW-UHFFFAOYSA-N CN1N=CC=C1C1=CC=C2C(N)=NOC2=N1 Chemical compound CN1N=CC=C1C1=CC=C2C(N)=NOC2=N1 KUTMWJSWDFIUMW-UHFFFAOYSA-N 0.000 claims 4
- DIWMNIZUAXAZIS-UHFFFAOYSA-N COC1=C(C=CC=C1)C=1C=C2C(=NC=1)ON=C2N Chemical compound COC1=C(C=CC=C1)C=1C=C2C(=NC=1)ON=C2N DIWMNIZUAXAZIS-UHFFFAOYSA-N 0.000 claims 4
- HWEZWOQRYRSPSM-UHFFFAOYSA-N COC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1 Chemical compound COC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1 HWEZWOQRYRSPSM-UHFFFAOYSA-N 0.000 claims 4
- AJDYMYFAFLHROU-UHFFFAOYSA-N COC1=C2C(=NC=C1)ON=C2N Chemical compound COC1=C2C(=NC=C1)ON=C2N AJDYMYFAFLHROU-UHFFFAOYSA-N 0.000 claims 4
- TYEANTJQCKKWPT-UHFFFAOYSA-N COC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1 Chemical compound COC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1 TYEANTJQCKKWPT-UHFFFAOYSA-N 0.000 claims 4
- UYRZVLMGJJYUDM-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1(C=CC=2C(=N1)ONC=2N)N Chemical compound COC=1C=C(C=CC=1)C1(C=CC=2C(=N1)ONC=2N)N UYRZVLMGJJYUDM-UHFFFAOYSA-N 0.000 claims 4
- VQIDBFITOQUYEJ-UHFFFAOYSA-N COC=1C=C(C=CC=1)C=1C=C2C(=NC=1)ON=C2N Chemical compound COC=1C=C(C=CC=1)C=1C=C2C(=NC=1)ON=C2N VQIDBFITOQUYEJ-UHFFFAOYSA-N 0.000 claims 4
- DXMBXEWBMFZBFL-UHFFFAOYSA-N COC=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1 Chemical compound COC=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1 DXMBXEWBMFZBFL-UHFFFAOYSA-N 0.000 claims 4
- PFYYQOZVOGLKEV-UHFFFAOYSA-N COCC#CC=1C=C2C(=NC=1)ON=C2N Chemical compound COCC#CC=1C=C2C(=NC=1)ON=C2N PFYYQOZVOGLKEV-UHFFFAOYSA-N 0.000 claims 4
- UYMVPQHQKHTCGV-UHFFFAOYSA-N CS(=O)(=O)C1=CC=C2C(=N1)ON=C2N Chemical compound CS(=O)(=O)C1=CC=C2C(=N1)ON=C2N UYMVPQHQKHTCGV-UHFFFAOYSA-N 0.000 claims 4
- DUHFWRRZLVAQBD-UHFFFAOYSA-N CSC1=C2C(=NC(=N1)C1=CC=CC=C1)ON=C2N Chemical compound CSC1=C2C(=NC(=N1)C1=CC=CC=C1)ON=C2N DUHFWRRZLVAQBD-UHFFFAOYSA-N 0.000 claims 4
- KWUCRDFOHKSXGE-UHFFFAOYSA-N CSC1=CC=C2C(=N1)ON=C2N Chemical compound CSC1=CC=C2C(=N1)ON=C2N KWUCRDFOHKSXGE-UHFFFAOYSA-N 0.000 claims 4
- JLNARRUFROTVGE-UHFFFAOYSA-N CSC1=NC=C2C(=N1)ON=C2N Chemical compound CSC1=NC=C2C(=N1)ON=C2N JLNARRUFROTVGE-UHFFFAOYSA-N 0.000 claims 4
- 101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 claims 4
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 4
- MTIDNIWREKNKHM-UHFFFAOYSA-N ClC1=C(C=C2C(=N1)ON=C2N)F Chemical compound ClC1=C(C=C2C(=N1)ON=C2N)F MTIDNIWREKNKHM-UHFFFAOYSA-N 0.000 claims 4
- FTYNGVVGVBNMCZ-UHFFFAOYSA-N ClC1=C(C=CC(=C1)C(F)(F)F)C=1C=C2C(=NC=1)ON=C2N Chemical compound ClC1=C(C=CC(=C1)C(F)(F)F)C=1C=C2C(=NC=1)ON=C2N FTYNGVVGVBNMCZ-UHFFFAOYSA-N 0.000 claims 4
- GJTXCKVACBHJBM-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C1=CC=C2C(=N1)ON=C2N Chemical compound ClC1=C(C=CC(=C1)Cl)C1=CC=C2C(=N1)ON=C2N GJTXCKVACBHJBM-UHFFFAOYSA-N 0.000 claims 4
- RFTAMIIFXPPDDT-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C=1C=C2C(=NC=1)ON=C2N Chemical compound ClC1=C(C=CC(=C1)Cl)C=1C=C2C(=NC=1)ON=C2N RFTAMIIFXPPDDT-UHFFFAOYSA-N 0.000 claims 4
- RGXPNUXXIAJTCF-UHFFFAOYSA-N ClC1=C(C=CC(=C1Cl)Cl)C=1C=C2C(=NC=1)ON=C2N Chemical compound ClC1=C(C=CC(=C1Cl)Cl)C=1C=C2C(=NC=1)ON=C2N RGXPNUXXIAJTCF-UHFFFAOYSA-N 0.000 claims 4
- DJZPDCDBCOESKC-UHFFFAOYSA-N ClC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1 Chemical compound ClC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1 DJZPDCDBCOESKC-UHFFFAOYSA-N 0.000 claims 4
- FQUKGVSRJVUOPA-UHFFFAOYSA-N ClC1=CC(=C2C(=N1)ON=C2N)C Chemical compound ClC1=CC(=C2C(=N1)ON=C2N)C FQUKGVSRJVUOPA-UHFFFAOYSA-N 0.000 claims 4
- RUNHWMKUSIPAOB-UHFFFAOYSA-N ClC1=CC(=C2C(=N1)ON=C2N)C(F)(F)F Chemical compound ClC1=CC(=C2C(=N1)ON=C2N)C(F)(F)F RUNHWMKUSIPAOB-UHFFFAOYSA-N 0.000 claims 4
- XFQQQLSINPIKBY-UHFFFAOYSA-N ClC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1 Chemical compound ClC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1 XFQQQLSINPIKBY-UHFFFAOYSA-N 0.000 claims 4
- BBJRHZULJQREAE-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1C)ON=C2NC)C Chemical compound ClC=1C(=C2C(=NC=1C)ON=C2NC)C BBJRHZULJQREAE-UHFFFAOYSA-N 0.000 claims 4
- DOVXTLVCVZOIFC-UHFFFAOYSA-N ClC=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1 Chemical compound ClC=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1 DOVXTLVCVZOIFC-UHFFFAOYSA-N 0.000 claims 4
- FWABYRKMYXNUKF-UHFFFAOYSA-N ClC=1C=C2C(=NC=1Cl)ON=C2N Chemical compound ClC=1C=C2C(=NC=1Cl)ON=C2N FWABYRKMYXNUKF-UHFFFAOYSA-N 0.000 claims 4
- YRRRAHUYWSATLT-UHFFFAOYSA-N FC(C=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1)(F)F Chemical compound FC(C=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1)(F)F YRRRAHUYWSATLT-UHFFFAOYSA-N 0.000 claims 4
- KNHFGARWARUJJC-UHFFFAOYSA-N FC(F)(F)C1=C(C=CC=C1)C1=C2C(=NC=C1)ON=C2N Chemical compound FC(F)(F)C1=C(C=CC=C1)C1=C2C(=NC=C1)ON=C2N KNHFGARWARUJJC-UHFFFAOYSA-N 0.000 claims 4
- GMULCDLNBPZLBC-UHFFFAOYSA-N FC(OC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1)(F)F Chemical compound FC(OC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1)(F)F GMULCDLNBPZLBC-UHFFFAOYSA-N 0.000 claims 4
- YBPJZGCDCMJTNO-UHFFFAOYSA-N FC(OC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1)(F)F Chemical compound FC(OC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1)(F)F YBPJZGCDCMJTNO-UHFFFAOYSA-N 0.000 claims 4
- MGZMNYOYFSMEMG-UHFFFAOYSA-N FC(OC=1C(=C2C(=NC=1C)ON=C2N)C)F Chemical compound FC(OC=1C(=C2C(=NC=1C)ON=C2N)C)F MGZMNYOYFSMEMG-UHFFFAOYSA-N 0.000 claims 4
- ZYWPSHBPASGYCP-UHFFFAOYSA-N FC(OC=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1)(F)F Chemical compound FC(OC=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1)(F)F ZYWPSHBPASGYCP-UHFFFAOYSA-N 0.000 claims 4
- KVKGCTNSQYFKGS-UHFFFAOYSA-N FC1=C(C=CC(=C1)F)C1=CC=C2C(=N1)ON=C2N Chemical compound FC1=C(C=CC(=C1)F)C1=CC=C2C(=N1)ON=C2N KVKGCTNSQYFKGS-UHFFFAOYSA-N 0.000 claims 4
- CSSDCQOVABTZOR-UHFFFAOYSA-N FC1=C(C=CC(=C1)F)C=1C=C2C(=NC=1)ON=C2N Chemical compound FC1=C(C=CC(=C1)F)C=1C=C2C(=NC=1)ON=C2N CSSDCQOVABTZOR-UHFFFAOYSA-N 0.000 claims 4
- QTKFJZASOFLULG-UHFFFAOYSA-N FC1=CC=C(C=C1)C1=CC=C2C(=N1)ON=C2N Chemical compound FC1=CC=C(C=C1)C1=CC=C2C(=N1)ON=C2N QTKFJZASOFLULG-UHFFFAOYSA-N 0.000 claims 4
- XSXPOYXHVYJXFZ-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=1)ON=C2N Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=1)ON=C2N XSXPOYXHVYJXFZ-UHFFFAOYSA-N 0.000 claims 4
- WFILVBBVQSEXCW-UHFFFAOYSA-N FC1=CC=C(C=N1)C=1C=C2C(=NC=1)ON=C2N Chemical compound FC1=CC=C(C=N1)C=1C=C2C(=NC=1)ON=C2N WFILVBBVQSEXCW-UHFFFAOYSA-N 0.000 claims 4
- WFPMQYUBDLOULN-UHFFFAOYSA-N FC=1C(=C(C=C(C=1)F)C=1C=C2C(=NC=1)ON=C2N)OC Chemical compound FC=1C(=C(C=C(C=1)F)C=1C=C2C(=NC=1)ON=C2N)OC WFPMQYUBDLOULN-UHFFFAOYSA-N 0.000 claims 4
- MDLVWRYEMRJBGG-UHFFFAOYSA-N FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)ON=C2N Chemical compound FC=1C=C(C=CC=1)C=1C=C2C(=NC=1)ON=C2N MDLVWRYEMRJBGG-UHFFFAOYSA-N 0.000 claims 4
- RVPOFFKGIMXXDK-UHFFFAOYSA-N FC=1C=C(C=CC=1OC)C=1C=C2C(=NC=1)ON=C2N Chemical compound FC=1C=C(C=CC=1OC)C=1C=C2C(=NC=1)ON=C2N RVPOFFKGIMXXDK-UHFFFAOYSA-N 0.000 claims 4
- KMFXMFGXIOCQFQ-UHFFFAOYSA-N FC=1C=C2C(=NC=1)ON=C2N Chemical compound FC=1C=C2C(=NC=1)ON=C2N KMFXMFGXIOCQFQ-UHFFFAOYSA-N 0.000 claims 4
- OMKDMJFMDNPQQF-UHFFFAOYSA-N FC=1C=C2C(=NC=1N(C)C)ON=C2N Chemical compound FC=1C=C2C(=NC=1N(C)C)ON=C2N OMKDMJFMDNPQQF-UHFFFAOYSA-N 0.000 claims 4
- ZXRZICREPUILAD-UHFFFAOYSA-N FC=1C=C2C(=NC=1N1CCOCC1)ON=C2N Chemical compound FC=1C=C2C(=NC=1N1CCOCC1)ON=C2N ZXRZICREPUILAD-UHFFFAOYSA-N 0.000 claims 4
- IINPFXZWINSOPA-UHFFFAOYSA-N IC=1C=C2C(=NC=1)ON=C2N Chemical compound IC=1C=C2C(=NC=1)ON=C2N IINPFXZWINSOPA-UHFFFAOYSA-N 0.000 claims 4
- UOKUMYQZVUDCJC-UHFFFAOYSA-N N1=CC(=CC=C1)C=1C=C2C(=NC=1)ON=C2N Chemical compound N1=CC(=CC=C1)C=1C=C2C(=NC=1)ON=C2N UOKUMYQZVUDCJC-UHFFFAOYSA-N 0.000 claims 4
- MMJSEMOUPFPKMZ-UHFFFAOYSA-N N1=CC=C(C=C1)C=1C=C2C(=NC=1)ON=C2N Chemical compound N1=CC=C(C=C1)C=1C=C2C(=NC=1)ON=C2N MMJSEMOUPFPKMZ-UHFFFAOYSA-N 0.000 claims 4
- QJSLLHXNMKQHGG-UHFFFAOYSA-N NC1=NOC2=NC(=C(C=C21)C(=O)OCC)C Chemical compound NC1=NOC2=NC(=C(C=C21)C(=O)OCC)C QJSLLHXNMKQHGG-UHFFFAOYSA-N 0.000 claims 4
- PIRPWFPVBJLCPA-UHFFFAOYSA-N NC1=NOC2=NC(=CC=C21)C(=O)O Chemical compound NC1=NOC2=NC(=CC=C21)C(=O)O PIRPWFPVBJLCPA-UHFFFAOYSA-N 0.000 claims 4
- BTHMBXPJTSSBEV-UHFFFAOYSA-N NC1=NOC2=NC(=CC=C21)C(=O)OC Chemical compound NC1=NOC2=NC(=CC=C21)C(=O)OC BTHMBXPJTSSBEV-UHFFFAOYSA-N 0.000 claims 4
- AMXCYRDAXOTYFU-UHFFFAOYSA-N NC1=NOC2=NC=C(C=C21)C1=C(C=CC=C1)O Chemical compound NC1=NOC2=NC=C(C=C21)C1=C(C=CC=C1)O AMXCYRDAXOTYFU-UHFFFAOYSA-N 0.000 claims 4
- BITWNUFLLPRVMT-UHFFFAOYSA-N NC1=NOC2=NC=C(C=C21)C1=CC=C(C=C1)O Chemical compound NC1=NOC2=NC=C(C=C21)C1=CC=C(C=C1)O BITWNUFLLPRVMT-UHFFFAOYSA-N 0.000 claims 4
- JEKRVDRDZKIDNG-UHFFFAOYSA-N NC=1C=C(C=CC=1)C=1C=C2C(=NC=1)ON=C2N Chemical compound NC=1C=C(C=CC=1)C=1C=C2C(=NC=1)ON=C2N JEKRVDRDZKIDNG-UHFFFAOYSA-N 0.000 claims 4
- RLSSWQJRDUTFSL-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=CC=C2C(=N1)ON=C2N Chemical compound O(C1=CC=CC=C1)C1=CC=C2C(=N1)ON=C2N RLSSWQJRDUTFSL-UHFFFAOYSA-N 0.000 claims 4
- BBJVZOSBBQSGNE-UHFFFAOYSA-N O1C(=CC=C1)C1=CC=C2C(=N1)ON=C2N Chemical compound O1C(=CC=C1)C1=CC=C2C(=N1)ON=C2N BBJVZOSBBQSGNE-UHFFFAOYSA-N 0.000 claims 4
- DOXSZRYRWZPLDD-UHFFFAOYSA-N O1CCN(CC1)CCOC1=CC=C2C(=N1)ON=C2N Chemical compound O1CCN(CC1)CCOC1=CC=C2C(=N1)ON=C2N DOXSZRYRWZPLDD-UHFFFAOYSA-N 0.000 claims 4
- WLTBFAFDZDRJAI-UHFFFAOYSA-N O1N=C(C=2C1=NC(=CC=2)N)N Chemical compound O1N=C(C=2C1=NC(=CC=2)N)N WLTBFAFDZDRJAI-UHFFFAOYSA-N 0.000 claims 4
- IZLPZGGVAGCKSH-UHFFFAOYSA-N O1N=C(C=2C1=NC1=C(C=2)COCC1)N Chemical compound O1N=C(C=2C1=NC1=C(C=2)COCC1)N IZLPZGGVAGCKSH-UHFFFAOYSA-N 0.000 claims 4
- NGLPMLCOCCIVFH-UHFFFAOYSA-N O1N=C(C=2C=C3C(=NC=21)CCCCC3)N Chemical compound O1N=C(C=2C=C3C(=NC=21)CCCCC3)N NGLPMLCOCCIVFH-UHFFFAOYSA-N 0.000 claims 4
- NROZBEQWDGMCOB-UHFFFAOYSA-N S1C(=CC=C1)C1=CC=C2C(=N1)ON=C2N Chemical compound S1C(=CC=C1)C1=CC=C2C(=N1)ON=C2N NROZBEQWDGMCOB-UHFFFAOYSA-N 0.000 claims 4
- MTZCQWRPKZDINF-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C2C(=NC=1)ON=C2N Chemical compound [N+](=O)([O-])C=1C=C2C(=NC=1)ON=C2N MTZCQWRPKZDINF-UHFFFAOYSA-N 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 claims 4
- 125000003725 azepanyl group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- UVQCLCHLERGNRX-UHFFFAOYSA-N C1(CC1)NC1=C(C=C2C(=N1)ON=C2N)F Chemical compound C1(CC1)NC1=C(C=C2C(=N1)ON=C2N)F UVQCLCHLERGNRX-UHFFFAOYSA-N 0.000 claims 3
- ARZDJXOCFVTHDI-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C2C(=N1)ON=C2N Chemical compound COC1=CC=C(C=C1)C1=CC=C2C(=N1)ON=C2N ARZDJXOCFVTHDI-UHFFFAOYSA-N 0.000 claims 3
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims 3
- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- VMZKRJDRHMFQBV-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1,2]oxazolo[5,4-b]quinolin-3-amine Chemical compound C1CCCC2=C1N=C1ON=C(N)C1=C2 VMZKRJDRHMFQBV-UHFFFAOYSA-N 0.000 claims 2
- FCOPBLPMMCTEQE-UHFFFAOYSA-N 5-bromo-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound C1=C(Br)C=C2C(N)=NOC2=N1 FCOPBLPMMCTEQE-UHFFFAOYSA-N 0.000 claims 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 2
- FDGRAWJKMFJLQE-UHFFFAOYSA-N 5-phenyl-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound C1=C2C(N)=NOC2=NC=C1C1=CC=CC=C1 FDGRAWJKMFJLQE-UHFFFAOYSA-N 0.000 claims 2
- JHDNLAITWWDCCR-UHFFFAOYSA-N 6-(trifluoromethyl)-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound FC(F)(F)C1=CC=C2C(N)=NOC2=N1 JHDNLAITWWDCCR-UHFFFAOYSA-N 0.000 claims 2
- YZSDNYDQYOOJOM-UHFFFAOYSA-N 6-chloro-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound ClC1=CC=C2C(N)=NOC2=N1 YZSDNYDQYOOJOM-UHFFFAOYSA-N 0.000 claims 2
- JBFROJLIVMFCCS-UHFFFAOYSA-N 6-methoxy-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound COC1=CC=C2C(N)=NOC2=N1 JBFROJLIVMFCCS-UHFFFAOYSA-N 0.000 claims 2
- LCHNQMGOJYXLSX-UHFFFAOYSA-N 6-methyl-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound CC1=CC=C2C(N)=NOC2=N1 LCHNQMGOJYXLSX-UHFFFAOYSA-N 0.000 claims 2
- CHLUYZPPSAYPDP-UHFFFAOYSA-N 6-methyl-[1,2]oxazolo[5,4-d]pyrimidin-3-amine Chemical compound CC1=NC=C2C(N)=NOC2=N1 CHLUYZPPSAYPDP-UHFFFAOYSA-N 0.000 claims 2
- HLSOGNYIKYIQEN-UHFFFAOYSA-N COC1=CC=C(C=C1)C1(C=CC=2C(=N1)ONC=2N)N Chemical compound COC1=CC=C(C=C1)C1(C=CC=2C(=N1)ONC=2N)N HLSOGNYIKYIQEN-UHFFFAOYSA-N 0.000 claims 2
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims 2
- RBYICHYEXYRQFK-UHFFFAOYSA-N [1,2]oxazolo[4,5-c]pyridin-3-amine Chemical compound C1=NC=C2C(N)=NOC2=C1 RBYICHYEXYRQFK-UHFFFAOYSA-N 0.000 claims 2
- WTXNZXKXRNMDDT-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]quinolin-3-amine Chemical compound C1=CC=C2C=C3C(N)=NOC3=NC2=C1 WTXNZXKXRNMDDT-UHFFFAOYSA-N 0.000 claims 2
- REINGZOTPYBONL-UHFFFAOYSA-N [1,2]oxazolo[5,4-d]pyrimidin-3-amine Chemical compound C1=NC=C2C(N)=NOC2=N1 REINGZOTPYBONL-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229960004012 amifampridine Drugs 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- 108091007741 Chimeric antigen receptor T cells Proteins 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 102000037982 Immune checkpoint proteins Human genes 0.000 claims 1
- 108091008036 Immune checkpoint proteins Proteins 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 230000037005 anaesthesia Effects 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229940022399 cancer vaccine Drugs 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000004392 genitalia Anatomy 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ62868814 | 2014-08-13 | ||
| NZ628688 | 2014-08-13 | ||
| PCT/IB2015/056129 WO2016024233A1 (en) | 2014-08-13 | 2015-08-12 | Inhibitors of tryptophan dioxygenases (ido1 and tdo) and their use in therapy |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020171335A Division JP2021006579A (ja) | 2014-08-13 | 2020-10-09 | トリプトファンジオキシゲナーゼ（ｉｄｏ１とｔｄｏ）の阻害剤及び治療におけるその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017527548A JP2017527548A (ja) | 2017-09-21 |
| JP2017527548A5 true JP2017527548A5 (enExample) | 2018-09-27 |
| JP7323985B2 JP7323985B2 (ja) | 2023-08-09 |
Family
ID=55303920
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017507807A Active JP7323985B2 (ja) | 2014-08-13 | 2015-08-12 | トリプトファンジオキシゲナーゼ（ｉｄｏ１とｔｄｏ）の阻害剤及び治療におけるその使用 |
| JP2020171335A Pending JP2021006579A (ja) | 2014-08-13 | 2020-10-09 | トリプトファンジオキシゲナーゼ（ｉｄｏ１とｔｄｏ）の阻害剤及び治療におけるその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020171335A Pending JP2021006579A (ja) | 2014-08-13 | 2020-10-09 | トリプトファンジオキシゲナーゼ（ｉｄｏ１とｔｄｏ）の阻害剤及び治療におけるその使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US10888567B2 (enExample) |
| EP (1) | EP3180002B1 (enExample) |
| JP (2) | JP7323985B2 (enExample) |
| KR (3) | KR102746352B1 (enExample) |
| CN (3) | CN106794176A (enExample) |
| AU (2) | AU2015302908B2 (enExample) |
| CA (1) | CA2957884A1 (enExample) |
| ES (1) | ES2925471T3 (enExample) |
| WO (1) | WO2016024233A1 (enExample) |
| ZA (1) | ZA201700924B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102746352B1 (ko) | 2014-08-13 | 2024-12-24 | 오클랜드 유니서비시즈 리미티드 | 트립토판 디옥시게나제 (ido1 및 tdo)의 억제제 및 치료에서 이들의 용도 |
| AU2016312848A1 (en) * | 2015-08-27 | 2018-03-29 | Auckland Uniservices Limited | Inhibitors of tryptophan dioxygenases (IDO1 and TDO) and their use in therapy |
| RU2619120C1 (ru) * | 2016-06-06 | 2017-05-12 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кубанский государственный аграрный университет" | 5-Хлор-3-(3-хлорфенилкарбоксамидо)-4,6-диметилизоксазоло[5,4-b]пиридин в качестве антидота 2,4-Д на подсолнечнике |
| EP3269714A1 (en) | 2016-07-13 | 2018-01-17 | Netherlands Translational Research Center B.V. | Inhibitors of tryptophan 2,3-dioxygenase |
| US10882856B2 (en) | 2016-09-24 | 2021-01-05 | Beigene, Ltd. | 5 or 8-substituted imidazo [1,5-a] pyridines as selective inhibitors of indoleamine and/or tryptophane 2,3-dioxygenases |
| WO2018071873A2 (en) | 2016-10-13 | 2018-04-19 | Juno Therapeutics, Inc. | Immunotherapy methods and compositions involving tryptophan metabolic pathway modulators |
| CA3047002A1 (en) | 2017-01-17 | 2018-07-26 | Board Of Regents, The University Of Texas System | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
| CN106905256A (zh) * | 2017-03-06 | 2017-06-30 | 中国药科大学 | 苯并五元杂环类ido1抑制剂、其制备方法及应用 |
| EP3697791A4 (en) | 2017-10-19 | 2021-06-16 | JS Innopharm (Shanghai) Ltd. | HETEROCYCLIC COMPOUNDS, COMPOSITIONS INCLUDING THE HETEROCYCLIC COMPOUND, AND METHODS OF USE THEREOF |
| CN118740348A (zh) | 2018-03-14 | 2024-10-01 | 华为技术有限公司 | 数据传输方法、装置及系统 |
| US11046649B2 (en) | 2018-07-17 | 2021-06-29 | Board Of Regents, The University Of Texas System | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
| JP6912016B1 (ja) * | 2020-04-10 | 2021-07-28 | 小野薬品工業株式会社 | Ｓｔｉｎｇ作動化合物 |
| KR102653960B1 (ko) * | 2020-07-23 | 2024-04-03 | 의료법인 성광의료재단 | 암 치료를 위한 면역체크포인트 억제제의 병용 요법 |
| EP4301358A2 (en) | 2021-03-05 | 2024-01-10 | Universität Basel Vizerektorat Forschung | Compositions for the treatment of ebv associated diseases or conditions |
| EP4052705A1 (en) | 2021-03-05 | 2022-09-07 | Universität Basel Vizerektorat Forschung | Compositions for the treatment of ebv associated diseases or conditions |
| JP2025507981A (ja) | 2022-03-04 | 2025-03-21 | アンティド セラピューティクス インターナショナル ソシエテ ア レスポンサビリテ リミティー | トリプトファンジオキシゲナーゼ（ｉｄｏ１及びｔｄｏ）の二重阻害剤と療法におけるそれらの使用 |
| WO2025046519A1 (en) * | 2023-08-31 | 2025-03-06 | Antido Therapeutics International Sarl | Combination for use in the treatment of glioma |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL123588B1 (en) | 1979-12-20 | 1982-10-30 | Akad Rolnicza | Rotary dynamometer for measurement of useful work of machining |
| WO2001079193A2 (en) * | 2000-04-14 | 2001-10-25 | Corvas International, Inc. | Substituted hydrazinyl heteroaromatic inhibitors of thrombin |
| US20070197610A1 (en) | 2004-03-16 | 2007-08-23 | Janssen Pharmaceutica N.V. | Benzisoxazoles |
| TW200633990A (en) | 2004-11-18 | 2006-10-01 | Takeda Pharmaceuticals Co | Amide compound |
| RS52711B (sr) * | 2005-05-10 | 2013-08-30 | Incyte Corporation | Modulatori indolamin 2,3-dioksigenaze i postupci upotrebe istih |
| DE102005038947A1 (de) | 2005-05-18 | 2006-11-30 | Grünenthal GmbH | Substituierte Benzo[d]isoxazol-3-yl-amin-Verbindungen und deren Verwendung in Arzneimitteln |
| DE102005026194A1 (de) | 2005-06-06 | 2006-12-07 | Grünenthal GmbH | Substituierte N-Benzo[d]isoxazol-3-yl-amin-Derivate und deren Verwendung zur Herstellung von Arzneimitteln |
| EP2227233B1 (en) | 2007-11-30 | 2013-02-13 | Newlink Genetics | Ido inhibitors |
| WO2010068452A1 (en) | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| WO2010068453A1 (en) | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| WO2010102778A2 (de) | 2009-03-10 | 2010-09-16 | Grünenthal GmbH | Substituierte 3-aminoisoxazolopyridine als kcnq2/3 modulatoren |
| JP2013519685A (ja) * | 2010-02-11 | 2013-05-30 | ヴァンダービルト ユニバーシティー | ｍＧｌｕＲ４アロステリック増強剤としてのベンズイソオキサゾール類およびアザベンズイソオキサゾール類、組成物、および神経機能不全を治療する方法 |
| US20100234491A1 (en) * | 2010-05-27 | 2010-09-16 | Morteza Khorrami | Method and material for manufacturing fiber cement board |
| PL2595995T3 (pl) * | 2010-07-22 | 2016-05-31 | Basf Se | Chwastobójcze izoksazolo[5,4-b]pirydyny |
| JP5672077B2 (ja) * | 2011-03-04 | 2015-02-18 | セイコーエプソン株式会社 | 発光素子、発光装置、表示装置および電子機器 |
| WO2013104561A1 (en) * | 2012-01-12 | 2013-07-18 | Basf Se | Herbicidal isoxazolo[5,4-b]pyridines |
| PL220630B1 (pl) * | 2012-12-28 | 2015-11-30 | Inst Immunologii I Terapii Doświadczalnej Pan | Nowe sulfonamidowe pochodne izoksazolo[5,4-b]pirydyny o aktywności przeciwbakteryjnej, sposób ich wytwarzania oraz nowe zastosowanie 3-aminoizoksazolo[5,4-b]pirydyny |
| HUE039473T2 (hu) | 2013-03-14 | 2019-01-28 | Curadev Pharma Private Ltd | Kinurenin útvonal inhibitorok |
| EP3082802B1 (en) | 2013-12-03 | 2020-02-26 | Iomet Pharma Ltd. | Tryptophan-2,3-dioxygenase (tdo) and/or indolamine-2,3-dioxygenase (ido) inhibitors and their use |
| KR102746352B1 (ko) | 2014-08-13 | 2024-12-24 | 오클랜드 유니서비시즈 리미티드 | 트립토판 디옥시게나제 (ido1 및 tdo)의 억제제 및 치료에서 이들의 용도 |
| RU2619120C1 (ru) | 2016-06-06 | 2017-05-12 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кубанский государственный аграрный университет" | 5-Хлор-3-(3-хлорфенилкарбоксамидо)-4,6-диметилизоксазоло[5,4-b]пиридин в качестве антидота 2,4-Д на подсолнечнике |
-
2015
- 2015-08-12 KR KR1020247002643A patent/KR102746352B1/ko active Active
- 2015-08-12 CN CN201580055358.7A patent/CN106794176A/zh active Pending
- 2015-08-12 EP EP15832016.8A patent/EP3180002B1/en active Active
- 2015-08-12 WO PCT/IB2015/056129 patent/WO2016024233A1/en not_active Ceased
- 2015-08-12 US US15/503,210 patent/US10888567B2/en active Active
- 2015-08-12 CA CA2957884A patent/CA2957884A1/en active Pending
- 2015-08-12 CN CN202311412286.XA patent/CN117599049A/zh active Pending
- 2015-08-12 JP JP2017507807A patent/JP7323985B2/ja active Active
- 2015-08-12 CN CN202311408585.6A patent/CN117618423A/zh active Pending
- 2015-08-12 KR KR1020177006662A patent/KR20170034439A/ko not_active Ceased
- 2015-08-12 ES ES15832016T patent/ES2925471T3/es active Active
- 2015-08-12 KR KR1020247042036A patent/KR20250007032A/ko active Pending
- 2015-08-12 AU AU2015302908A patent/AU2015302908B2/en active Active
-
2017
- 2017-02-06 ZA ZA2017/00924A patent/ZA201700924B/en unknown
-
2020
- 2020-05-12 AU AU2020203116A patent/AU2020203116B2/en active Active
- 2020-10-09 JP JP2020171335A patent/JP2021006579A/ja active Pending
- 2020-10-15 US US17/071,746 patent/US11826316B2/en active Active
-
2023
- 2023-10-16 US US18/380,392 patent/US12508268B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017527548A5 (enExample) | ||
| JP2016525075A5 (enExample) | ||
| JP2004525149A5 (enExample) | ||
| JP2013523710A5 (enExample) | ||
| JP2004527560A5 (enExample) | ||
| JP2016172739A5 (enExample) | ||
| JP2019503337A5 (enExample) | ||
| JP2016514719A5 (enExample) | ||
| JP2013528640A5 (enExample) | ||
| JP2011522866A5 (enExample) | ||
| HRP20200342T1 (hr) | Derivati dihidroimidazopirazinona korisni u liječenju raka | |
| JP2016505529A5 (enExample) | ||
| JP2016525076A5 (enExample) | ||
| JP2004529926A5 (enExample) | ||
| JP2016506369A5 (enExample) | ||
| RU2017106742A (ru) | Комбинированная терапия для лечения парамиксовируса | |
| JP2016511258A5 (enExample) | ||
| JP2018508553A5 (enExample) | ||
| JP2015517566A5 (enExample) | ||
| JP2016518372A5 (enExample) | ||
| RU2010125220A (ru) | Ненуклеозидные ингибиторы обратной транскриптазы | |
| RU2013136542A (ru) | Конденсированные производные аминодигидротиазина | |
| JP2015521634A5 (enExample) | ||
| RU2016137181A (ru) | Противофиброзные пиридиноны | |
| JP2017531039A5 (enExample) |