JP2014526499A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014526499A5 JP2014526499A5 JP2014530361A JP2014530361A JP2014526499A5 JP 2014526499 A5 JP2014526499 A5 JP 2014526499A5 JP 2014530361 A JP2014530361 A JP 2014530361A JP 2014530361 A JP2014530361 A JP 2014530361A JP 2014526499 A5 JP2014526499 A5 JP 2014526499A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pharmaceutically acceptable
- triazolo
- pyrazol
- acceptable salt
- 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
- 150000003839 salts Chemical class 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- -1 1-methyl-1H-pyrazol-4-yl Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- RQZASYHLVWNLOK-UHFFFAOYSA-N 1-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]piperidin-4-ol Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(O)CC3)=NN=C2C=C1 RQZASYHLVWNLOK-UHFFFAOYSA-N 0.000 claims description 3
- OCUFWFWPMTVLOB-CALCHBBNSA-N 3-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 OCUFWFWPMTVLOB-CALCHBBNSA-N 0.000 claims description 3
- URAMORWCRRAYRG-UHFFFAOYSA-N 4-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCOCC3)=NN=C2C=C1 URAMORWCRRAYRG-UHFFFAOYSA-N 0.000 claims description 3
- GGSJKYXMTHZWFU-UHFFFAOYSA-N 4-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCOCC3)=NN=C2C(F)=C1 GGSJKYXMTHZWFU-UHFFFAOYSA-N 0.000 claims description 3
- ZRUDAHOWOHKQAO-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-methoxypiperidin-1-yl)quinoline Chemical compound C1CC(OC)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 ZRUDAHOWOHKQAO-UHFFFAOYSA-N 0.000 claims description 3
- 230000004968 inflammatory condition Effects 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- PUWKUQQXKAHOFP-UHFFFAOYSA-N 1-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]piperidin-4-ol Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(O)CC3)=NN=C2C(F)=C1 PUWKUQQXKAHOFP-UHFFFAOYSA-N 0.000 claims description 2
- UJHKEEXPTFPJNG-UHFFFAOYSA-N 3-(4-methoxypiperidin-1-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1CC(OC)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 UJHKEEXPTFPJNG-UHFFFAOYSA-N 0.000 claims description 2
- GUQCOZKYQUTLJM-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1CN(C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 GUQCOZKYQUTLJM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- XELQJFZPZDIESZ-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-methylpiperazin-1-yl)quinoline Chemical compound C1CN(C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 XELQJFZPZDIESZ-UHFFFAOYSA-N 0.000 claims description 2
- OJMCEDPZTBVMKX-IYBDPMFKSA-N 3-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 OJMCEDPZTBVMKX-IYBDPMFKSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 description 19
- 229920006395 saturated elastomer Polymers 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- INPAZULREKEJFI-IBGZPJMESA-N (3s)-1-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 INPAZULREKEJFI-IBGZPJMESA-N 0.000 description 1
- JFUJCFQHJLAUFM-IBGZPJMESA-N (3s)-n,n-dimethyl-1-[6-[[6-(1-methylpyrazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]pyrrolidin-3-amine Chemical compound C1[C@@H](N(C)C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=NN(C)C=C2)=C2)C2=C1 JFUJCFQHJLAUFM-IBGZPJMESA-N 0.000 description 1
- ZYPGNMBTYZEVSF-AFUMVMLFSA-N (ne)-n-[1-[3-(3-morpholin-4-ylquinolin-6-yl)sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]ethylidene]hydroxylamine Chemical compound N12C=C(C(=N/O)/C)C=CC2=NN=C1SC(C=C1C=2)=CC=C1N=CC=2N1CCOCC1 ZYPGNMBTYZEVSF-AFUMVMLFSA-N 0.000 description 1
- PSNYRIOHVUOFPW-FLOSOGMCSA-N (ne)-n-[1-[3-[3-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]quinolin-6-yl]sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]ethylidene]hydroxylamine Chemical compound C1[C@@H](N(C)C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C(\C)=N\O)=C2)C2=C1 PSNYRIOHVUOFPW-FLOSOGMCSA-N 0.000 description 1
- ZTEMQDXNBKSGLA-UHFFFAOYSA-N 1-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]piperidin-3-amine Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CC(N)CCC3)=NN=C2C=C1 ZTEMQDXNBKSGLA-UHFFFAOYSA-N 0.000 description 1
- RFBXKLIIPVQMDB-UHFFFAOYSA-N 1-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]piperidin-4-amine Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(N)CC3)=NN=C2C=C1 RFBXKLIIPVQMDB-UHFFFAOYSA-N 0.000 description 1
- OBLFFFKSZZMQJH-UHFFFAOYSA-N 1-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]pyrrolidin-3-amine Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CC(N)CC3)=NN=C2C=C1 OBLFFFKSZZMQJH-UHFFFAOYSA-N 0.000 description 1
- ZXABHOBAANBQOO-LQKURTRISA-N 1-[6-[[6-[(e)-n-(2-hydroxyethoxy)-c-methylcarbonimidoyl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]piperidin-4-ol Chemical compound N12C=C(C(=N/OCCO)/C)C=CC2=NN=C1SC(C=C1C=2)=CC=C1N=CC=2N1CCC(O)CC1 ZXABHOBAANBQOO-LQKURTRISA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- JEWZQZFYIBRIBC-UHFFFAOYSA-N 2,6-dimethyl-4-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound C1C(C)OC(C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 JEWZQZFYIBRIBC-UHFFFAOYSA-N 0.000 description 1
- STWYWDMBNVHQIZ-JVWAILMASA-N 2-[(e)-1-[3-(3-morpholin-4-ylquinolin-6-yl)sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]ethylideneamino]oxyethanol Chemical compound N12C=C(C(=N/OCCO)/C)C=CC2=NN=C1SC(C=C1C=2)=CC=C1N=CC=2N1CCOCC1 STWYWDMBNVHQIZ-JVWAILMASA-N 0.000 description 1
- IYSRDIPKAXCGSE-XSZJBBQGSA-N 2-[(e)-1-[3-[3-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]quinolin-6-yl]sulfanyl-8-fluoro-[1,2,4]triazolo[4,3-a]pyridin-6-yl]ethylideneamino]oxyethanol Chemical compound C1[C@@H](N(C)C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C(\C)=N\OCCO)=C2)C2=C1 IYSRDIPKAXCGSE-XSZJBBQGSA-N 0.000 description 1
- XOSWEUYBKJZODE-CGKHLXHRSA-N 2-[(e)-1-[3-[3-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]quinolin-6-yl]sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]ethylideneamino]oxyethanol Chemical compound C1[C@@H](N(C)C)CCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C(\C)=N\OCCO)=C2)C2=C1 XOSWEUYBKJZODE-CGKHLXHRSA-N 0.000 description 1
- JZIKZJCBYAYGEA-UHFFFAOYSA-N 2-[4-[3-(3-morpholin-4-ylquinolin-6-yl)sulfanyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCOCC3)=NN=C2C=C1 JZIKZJCBYAYGEA-UHFFFAOYSA-N 0.000 description 1
- RECGTOTUFYGHJY-UHFFFAOYSA-N 2-[4-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-1,4-diazepan-1-yl]ethanol Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCN(CCO)CCC3)=NN=C2C=C1 RECGTOTUFYGHJY-UHFFFAOYSA-N 0.000 description 1
- QXMNTGNVLMNHEO-UHFFFAOYSA-N 2-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-8-oxa-2-azaspiro[4.5]decane Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CC4(CC3)CCOCC4)=NN=C2C=C1 QXMNTGNVLMNHEO-UHFFFAOYSA-N 0.000 description 1
- WHWAOQDLIBFTNE-UHFFFAOYSA-N 2-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-8-oxa-2-azaspiro[4.5]decane Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CC4(CC3)CCOCC4)=NN=C2C(F)=C1 WHWAOQDLIBFTNE-UHFFFAOYSA-N 0.000 description 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 description 1
- KSZWVRDXHXOEKN-UHFFFAOYSA-N 2-methyl-4-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound C1COC(C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 KSZWVRDXHXOEKN-UHFFFAOYSA-N 0.000 description 1
- KCSVVCQNVWNDNF-UHFFFAOYSA-N 3-(1,4-diazepan-1-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCNCCC3)=NN=C2C=C1 KCSVVCQNVWNDNF-UHFFFAOYSA-N 0.000 description 1
- OHQMOXPQJBEGOZ-UHFFFAOYSA-N 3-(4,4-difluoropiperidin-1-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(F)(F)CC3)=NN=C2C=C1 OHQMOXPQJBEGOZ-UHFFFAOYSA-N 0.000 description 1
- IABXEOYJCXGIMD-UHFFFAOYSA-N 3-(4,4-difluoropiperidin-1-yl)-6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(F)(F)CC3)=NN=C2C(F)=C1 IABXEOYJCXGIMD-UHFFFAOYSA-N 0.000 description 1
- XHWNFTZGGRJFLV-UHFFFAOYSA-N 3-(4-cyclohexylpiperazin-1-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCN(CC3)C3CCCCC3)=NN=C2C=C1 XHWNFTZGGRJFLV-UHFFFAOYSA-N 0.000 description 1
- KODNKVYGOJLHDP-UHFFFAOYSA-N 3-(4-methyl-1,4-diazepan-1-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1CN(C)CCCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 KODNKVYGOJLHDP-UHFFFAOYSA-N 0.000 description 1
- MAEFTXPFQHILHT-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinoline Chemical compound C1CN(C)CCN1CC1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 MAEFTXPFQHILHT-UHFFFAOYSA-N 0.000 description 1
- MDINHUDZVSNDEL-UHFFFAOYSA-N 3-methyl-4-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound CC1COCCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 MDINHUDZVSNDEL-UHFFFAOYSA-N 0.000 description 1
- PYICCQVWUOKFSY-UHFFFAOYSA-N 4-[6-[[6-(1h-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound C1COCCN1C1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CNN=C2)=C2)C2=C1 PYICCQVWUOKFSY-UHFFFAOYSA-N 0.000 description 1
- CKHSZGOIKJWYLP-UHFFFAOYSA-N 4-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 CKHSZGOIKJWYLP-UHFFFAOYSA-N 0.000 description 1
- NLRBOMANTTVJTI-UHFFFAOYSA-N 4-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-2-methylmorpholine Chemical compound C1COC(C)CN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 NLRBOMANTTVJTI-UHFFFAOYSA-N 0.000 description 1
- KUYMCRLOLWIWOI-UHFFFAOYSA-N 4-[6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-3-methylmorpholine Chemical compound CC1COCCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 KUYMCRLOLWIWOI-UHFFFAOYSA-N 0.000 description 1
- XVVKQPOCKFTKCR-UHFFFAOYSA-N 4-[6-[[8-fluoro-6-(1h-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]morpholine Chemical compound N=1N=C2C(F)=CC(C3=CNN=C3)=CN2C=1SC(C=C1C=2)=CC=C1N=CC=2N1CCOCC1 XVVKQPOCKFTKCR-UHFFFAOYSA-N 0.000 description 1
- ARFVFRRCPKPXGP-UHFFFAOYSA-N 4-[[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]methyl]morpholine Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(CN5CCOCC5)C=NC4=CC=3)=NN=C2C=C1 ARFVFRRCPKPXGP-UHFFFAOYSA-N 0.000 description 1
- GNCNEAGBGRHTAT-UHFFFAOYSA-N 6-[6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-yl]-2-oxa-6-azaspiro[3.3]heptane Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CC4(COC4)C3)=NN=C2C=C1 GNCNEAGBGRHTAT-UHFFFAOYSA-N 0.000 description 1
- WAZOXVCSFBYHOO-UHFFFAOYSA-N 6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-phenylpiperazin-1-yl)quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCN(CC3)C=3C=CC=CC=3)=NN=C2C=C1 WAZOXVCSFBYHOO-UHFFFAOYSA-N 0.000 description 1
- QTDCAXYCFZXWPG-UHFFFAOYSA-N 6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-piperidin-1-ylpiperidin-1-yl)quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(CC3)N3CCCCC3)=NN=C2C=C1 QTDCAXYCFZXWPG-UHFFFAOYSA-N 0.000 description 1
- TWVWCIKZBQUKNQ-UHFFFAOYSA-N 6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCN(CC(F)(F)F)CC3)=NN=C2C=C1 TWVWCIKZBQUKNQ-UHFFFAOYSA-N 0.000 description 1
- LQLJOSBZSDCEPQ-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-piperidin-1-ylpiperidin-1-yl)quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(CC3)N3CCCCC3)=NN=C2C(F)=C1 LQLJOSBZSDCEPQ-UHFFFAOYSA-N 0.000 description 1
- IFBRUUOIKYNFQU-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline Chemical compound C1=NN(C)C=C1C1=CN2C(SC=3C=C4C=C(C=NC4=CC=3)N3CCC(CC3)N3CCCC3)=NN=C2C(F)=C1 IFBRUUOIKYNFQU-UHFFFAOYSA-N 0.000 description 1
- CIPJSPNNLSDSSM-HNNXBMFYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-3-[(2s)-2-methylpiperazin-1-yl]quinoline Chemical compound C[C@H]1CNCCN1C1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 CIPJSPNNLSDSSM-HNNXBMFYSA-N 0.000 description 1
- IMTTXYPMOVLULF-UHFFFAOYSA-N 6-[[8-fluoro-6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]-n-(1-methylpiperidin-4-yl)quinolin-3-amine Chemical compound C1CN(C)CCC1NC1=CN=C(C=CC(SC=2N3C=C(C=C(F)C3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 IMTTXYPMOVLULF-UHFFFAOYSA-N 0.000 description 1
- IVGLGVJCVDBHBJ-UHFFFAOYSA-N CC=NOCCO Chemical compound CC=NOCCO IVGLGVJCVDBHBJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229940079593 drug Drugs 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- ZBAAKUHERHHMAH-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl]sulfanyl]quinolin-3-amine Chemical compound C1CN(C)CCC1NC1=CN=C(C=CC(SC=2N3C=C(C=CC3=NN=2)C2=CN(C)N=C2)=C2)C2=C1 ZBAAKUHERHHMAH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011079695 | 2011-09-15 | ||
| CNPCT/CN2011/079695 | 2011-09-15 | ||
| CN2012079055 | 2012-07-23 | ||
| CNPCT/CN2012/079055 | 2012-07-23 | ||
| PCT/IB2012/054775 WO2013038362A1 (en) | 2011-09-15 | 2012-09-13 | 6 - substituted 3 - (quinolin- 6 - ylthio) - [1,2,4] triazolo [4, 3 -a] pyradines as tyrosine kinase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014526499A JP2014526499A (ja) | 2014-10-06 |
| JP2014526499A5 true JP2014526499A5 (enExample) | 2015-11-05 |
| JP5957526B2 JP5957526B2 (ja) | 2016-07-27 |
Family
ID=46981017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014530361A Expired - Fee Related JP5957526B2 (ja) | 2011-09-15 | 2012-09-13 | チロシンキナーゼとしての６−置換３−（キノリン−６−イルチオ）−［１，２，４］トリアゾロ［４，３−ａ］ピラジン |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US9062045B2 (enExample) |
| EP (1) | EP2755976B1 (enExample) |
| JP (1) | JP5957526B2 (enExample) |
| KR (1) | KR20140077916A (enExample) |
| AR (1) | AR087868A1 (enExample) |
| AU (1) | AU2012310168B2 (enExample) |
| BR (1) | BR112014006223A8 (enExample) |
| CA (1) | CA2848809A1 (enExample) |
| EA (1) | EA026655B1 (enExample) |
| ES (1) | ES2691650T3 (enExample) |
| MX (1) | MX339302B (enExample) |
| TW (1) | TW201319067A (enExample) |
| UY (1) | UY34329A (enExample) |
| WO (1) | WO2013038362A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112015027440B1 (pt) * | 2013-05-10 | 2023-04-11 | Jiangsu Hansoh Pharmaceutical Co., Ltd | Derivado de [1,2,4]triazol[4,3-a]piridina, seus usos e seu processo de preparação, e composição farmacêutica |
| EP3013825B1 (en) | 2013-06-24 | 2019-08-07 | Amgen Inc. | Method for the preparation of (1,2,4)-triazolo(4,3-a)pyridines |
| GB201321742D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| AU2015296117B2 (en) * | 2014-08-01 | 2019-05-16 | Jiangsu Hansoh Pharmaceutical Group Co., Ltd. | Crystalline free bases of C-Met inhibitor or crystalline acid salts thereof, and preparation methods and uses thereof |
| CN105272995B (zh) | 2015-09-24 | 2017-10-27 | 上海海聚生物科技有限公司 | 喹啉类衍生物、其药物组合物、制备方法及应用 |
| CN106883250B (zh) * | 2015-12-15 | 2021-05-18 | 江苏豪森药业集团有限公司 | C-Met酪氨酸激酶抑制剂的制备方法 |
| UA127065C2 (uk) | 2018-04-25 | 2023-03-29 | Баєр Акціенгезельшафт | Нові гетероарил-триазольні та гетероарил-тетразольні сполуки як пестициди |
| MX2022000954A (es) | 2019-07-23 | 2022-02-14 | Bayer Ag | Novedosos compuestos de heteroaril-triazol como plaguicidas. |
| CN114502545B (zh) | 2019-07-23 | 2024-06-28 | 拜耳公司 | 作为农药的新的杂芳基-三唑化合物 |
| CN111440174B (zh) * | 2020-04-02 | 2021-07-09 | 广州医科大学 | 一种吡啶酰胺类化合物及其制备方法与应用 |
Family Cites Families (193)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1219606A (en) | 1968-07-15 | 1971-01-20 | Rech S Et D Applic Scient Soge | Quinuclidinol derivatives and preparation thereof |
| GB1524747A (en) | 1976-05-11 | 1978-09-13 | Ici Ltd | Polypeptide |
| US4358453A (en) | 1982-01-08 | 1982-11-09 | Schering Corporation | 1,2,4-Triazolo[4,3-a]pyridines |
| EP0100172B1 (en) | 1982-07-23 | 1987-08-12 | Imperial Chemical Industries Plc | Amide derivatives |
| GB8327256D0 (en) | 1983-10-12 | 1983-11-16 | Ici Plc | Steroid derivatives |
| FR2601952B1 (fr) | 1986-07-23 | 1988-11-25 | Carpibem | Nouveaux derives amino alkyl thio de triazolopyridine ou triazoloquinoline, leurs procedes de preparation, medicaments les contenant, utiles notamment comme antalgiques |
| US5093330A (en) | 1987-06-15 | 1992-03-03 | Ciba-Geigy Corporation | Staurosporine derivatives substituted at methylamino nitrogen |
| GB8916480D0 (en) | 1989-07-19 | 1989-09-06 | Glaxo Group Ltd | Chemical process |
| US5010099A (en) | 1989-08-11 | 1991-04-23 | Harbor Branch Oceanographic Institution, Inc. | Discodermolide compounds, compositions containing same and method of preparation and use |
| GB8923590D0 (en) | 1989-10-19 | 1989-12-06 | Pfizer Ltd | Antimuscarinic bronchodilators |
| US5395855A (en) | 1990-05-07 | 1995-03-07 | Ciba-Geigy Corporation | Hydrazones |
| PT100441A (pt) | 1991-05-02 | 1993-09-30 | Smithkline Beecham Corp | Pirrolidinonas, seu processo de preparacao, composicoes farmaceuticas que as contem e uso |
| US5451700A (en) | 1991-06-11 | 1995-09-19 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and methods of treatment |
| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| JP3192424B2 (ja) | 1992-04-02 | 2001-07-30 | スミスクライン・ビーチャム・コーポレイション | アレルギーまたは炎症疾患の治療用化合物 |
| WO1993019749A1 (en) | 1992-04-02 | 1993-10-14 | Smithkline Beecham Corporation | Compounds useful for treating allergic and inflammatory diseases |
| WO1993019751A1 (en) | 1992-04-02 | 1993-10-14 | Smithkline Beecham Corporation | Compounds useful for treating inflammatory diseases and inhibiting production of tumor necrosis factor |
| TW225528B (enExample) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| AU687727B2 (en) | 1992-10-28 | 1998-03-05 | Genentech Inc. | Vascular endothelial cell growth factor antagonists |
| GB9301000D0 (en) | 1993-01-20 | 1993-03-10 | Glaxo Group Ltd | Chemical compounds |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| DE4326758A1 (de) | 1993-08-10 | 1995-02-16 | Basf Ag | [1,3,4]Triazolo[1,5-a]pyridine |
| DE4329296A1 (de) | 1993-08-31 | 1995-03-02 | Basf Ag | Azofarbstoffe mit einer Diazokomponente aus der Anilinreihe und Kupplungskomponente aus der Triazolopyridinreihe |
| GB9414208D0 (en) | 1994-07-14 | 1994-08-31 | Glaxo Group Ltd | Compounds |
| GB9414193D0 (en) | 1994-07-14 | 1994-08-31 | Glaxo Group Ltd | Compounds |
| EP0817775B1 (en) | 1995-03-30 | 2001-09-12 | Pfizer Inc. | Quinazoline derivatives |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US5843901A (en) | 1995-06-07 | 1998-12-01 | Advanced Research & Technology Institute | LHRH antagonist peptides |
| ATE212993T1 (de) | 1995-07-06 | 2002-02-15 | Novartis Erfind Verwalt Gmbh | Pyrolopyrimidine und verfahren zu ihrer herstellung |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| EP0892789B2 (en) | 1996-04-12 | 2009-11-18 | Warner-Lambert Company LLC | Irreversible inhibitors of tyrosine kinases |
| DE69734513T2 (de) | 1996-06-24 | 2006-07-27 | Pfizer Inc. | Phenylamino-substituierte tricyclische derivate zur behandlung hyperproliferativer krankheiten |
| NZ334821A (en) | 1996-08-30 | 2000-12-22 | Novartis Ag | Method for producing epothilones |
| EP0938597B1 (en) | 1996-09-06 | 2003-08-20 | Obducat Aktiebolag | Method for anisotropic etching of structures in conducting materials |
| DE19638745C2 (de) | 1996-09-11 | 2001-05-10 | Schering Ag | Monoklonale Antikörper gegen die extrazelluläre Domäne des menschlichen VEGF - Rezeptorproteins (KDR) |
| AU4342997A (en) | 1996-09-13 | 1998-04-02 | Sugen, Inc. | Use of quinazoline derivatives for the manufacture of a medicament in the reatment of hyperproliferative skin disorders |
| EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
| GB9622386D0 (en) | 1996-10-28 | 1997-01-08 | Sandoz Ltd | Organic compounds |
| HU229833B1 (en) | 1996-11-18 | 2014-09-29 | Biotechnolog Forschung Gmbh | Epothilone d production process, and its use as cytostatic as well as phytosanitary agents |
| US6441186B1 (en) | 1996-12-13 | 2002-08-27 | The Scripps Research Institute | Epothilone analogs |
| TW528755B (en) | 1996-12-24 | 2003-04-21 | Glaxo Group Ltd | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
| CO4950519A1 (es) | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| US6166037A (en) | 1997-08-28 | 2000-12-26 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| WO1999016766A1 (en) | 1997-10-01 | 1999-04-08 | Kyowa Hakko Kogyo Co., Ltd. | Benzodioxole derivatives |
| GB9721069D0 (en) | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Polymeric derivatives of camptothecin |
| GB9723566D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723590D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723589D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| YU44900A (sh) | 1998-01-31 | 2003-01-31 | Glaxo Group Limited | Derivati 2-(purin-9-il)tetrahidrofuran-3,4-diola |
| PE20000270A1 (es) | 1998-02-14 | 2000-05-20 | Glaxo Group Ltd | Derivados de 2-(purin-9-il)-tetrahidrofuran-3,4-diol |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| AU758526B2 (en) | 1998-02-25 | 2003-03-20 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues therof |
| YU81100A (sh) | 1998-06-23 | 2003-10-31 | Glaxo Group Limited | Derivati 2-(purin-9-il)tetrahidrofuran-3,4 diola |
| GB9813540D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| GB9813565D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| GB9813535D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| DE69827673T2 (de) | 1998-06-30 | 2005-04-21 | Dow Global Technologies Inc | Polymerpolyole und ein verfahren zu ihrer darstellung |
| US6303625B1 (en) | 1998-07-27 | 2001-10-16 | Ortho-Mcneil Pharmaceutical, Inc. | Triazolopyridines for the treatment of thrombosis disorders |
| CN1152031C (zh) | 1998-08-11 | 2004-06-02 | 诺瓦提斯公司 | 具有血管生成抑制活性的异喹啉衍生物 |
| EP1121372B1 (en) | 1998-10-16 | 2006-06-28 | Pfizer Limited | Adenine derivatives |
| GB9824579D0 (en) | 1998-11-10 | 1999-01-06 | Novartis Ag | Organic compounds |
| UA71587C2 (uk) | 1998-11-10 | 2004-12-15 | Шерінг Акцієнгезелльшафт | Аміди антранілової кислоти та їхнє застосування як лікарських засобів |
| CN100381566C (zh) | 1998-11-20 | 2008-04-16 | 科森生物科学公司 | 产生环氧噻酮及其衍生物的重组方法和材料 |
| ATE300957T1 (de) | 1998-12-22 | 2005-08-15 | Genentech Inc | Antagonisten von vaskular-endothelialen zellwachstumsfaktoren und ihre anwendung |
| PT1165085E (pt) | 1999-03-30 | 2006-10-31 | Novartis Ag | Derivados de ftalazina para tratar doencas inflamatorias |
| GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| EP1175402B1 (en) | 1999-05-04 | 2005-07-20 | Schering Corporation | Piperidine derivatives useful as ccr5 antagonists |
| CZ20013940A3 (cs) | 1999-05-04 | 2002-04-17 | Schering Corporation | Piperazinové deriváty uľitečné jako CCR5 antagonisté |
| YU25500A (sh) | 1999-05-11 | 2003-08-29 | Pfizer Products Inc. | Postupak za sintezu analoga nukleozida |
| GB9913932D0 (en) | 1999-06-15 | 1999-08-18 | Pfizer Ltd | Purine derivatives |
| US6322771B1 (en) | 1999-06-18 | 2001-11-27 | University Of Virginia Patent Foundation | Induction of pharmacological stress with adenosine receptor agonists |
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| US6333335B1 (en) | 1999-07-23 | 2001-12-25 | Merck & Co., Inc. | Phenyl-protein transferase inhibitors |
| SI1212089T1 (sl) | 1999-08-21 | 2006-08-31 | Altana Pharma Ag | Sinergisticna kombinacija roflumilasta in salmeterola |
| CO5180581A1 (es) | 1999-09-30 | 2002-07-30 | Pfizer Prod Inc | Compuestos para el tratamiento de la isquemia ciones farmaceuticas que los contienen para el tratamiento de la isquemia |
| GB9924361D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Ltd | Purine derivatives |
| GB9924363D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Central Res | Purine derivatives |
| GB0003960D0 (en) | 2000-02-18 | 2000-04-12 | Pfizer Ltd | Purine derivatives |
| TWI227240B (en) | 2000-06-06 | 2005-02-01 | Pfizer | 2-aminocarbonyl-9H-purine derivatives |
| GB0015727D0 (en) | 2000-06-27 | 2000-08-16 | Pfizer Ltd | Purine derivatives |
| BR0112297A (pt) | 2000-06-27 | 2003-05-06 | S A L V A T Lab Sa | Compostos carbamatos derivados de arilalquilaminas |
| GB0015876D0 (en) | 2000-06-28 | 2000-08-23 | Novartis Ag | Organic compounds |
| DE10038639A1 (de) | 2000-07-28 | 2002-02-21 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| DE10038019A1 (de) | 2000-08-04 | 2002-02-14 | Bayer Ag | Substituierte Triazolopyrid(az)ine |
| CO5310534A1 (es) | 2000-08-05 | 2003-08-29 | Glaxo Group Ltd | Nuevos derivados de androstano anti-inflamatorios |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| GB0022695D0 (en) | 2000-09-15 | 2000-11-01 | Pfizer Ltd | Purine Derivatives |
| GB0028383D0 (en) | 2000-11-21 | 2001-01-03 | Novartis Ag | Organic compounds |
| EP1345937B1 (en) | 2000-12-22 | 2005-09-28 | Almirall Prodesfarma AG | Quinuclidine carbamate derivatives and their use as m3 antagonists |
| EE05404B1 (et) | 2000-12-28 | 2011-04-15 | Almirall Prodesfarma Ag | Kinuklidiini derivaat, selle saamine ja kasutamine ravimi valmistamiseks, mis on ette nhtud respiratoorsete, kuseelundite v?i mao-soolte haiguste ravimiseks, ning seda sisaldav ravimkompositsioon |
| EP1241176A1 (en) | 2001-03-16 | 2002-09-18 | Pfizer Products Inc. | Purine derivatives for the treatment of ischemia |
| ES2314052T3 (es) | 2001-04-30 | 2009-03-16 | Glaxo Group Limited | Derivados de ester de 17beta-carbotioato de androstano con un grupo ester ciclico en la posicion 17alfa. |
| AR035885A1 (es) | 2001-05-14 | 2004-07-21 | Novartis Ag | Derivados de 4-amino-5-fenil-7-ciclobutilpirrolo (2,3-d)pirimidina, un proceso para su preparacion, una composicion farmaceutica y el uso de dichos derivados para la preparacion de una composicion farmaceutica |
| BR0209986A (pt) | 2001-05-25 | 2004-04-06 | Pfizer | Agonista de a2a em combinação com um agente anticolinérgico, para o tratamento de doenças obstrutivas das vias respiratórias |
| US20040248867A1 (en) | 2001-06-12 | 2004-12-09 | Keith Biggadike | Novel anti-inflammatory 17.alpha.-heterocyclic-esters of 17.beta.carbothioate androstane derivatives |
| DK2327766T3 (en) | 2001-06-21 | 2016-03-07 | Basf Enzymes Llc | nitrilases |
| GB0119249D0 (en) | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| IL160896A0 (en) | 2001-10-17 | 2004-08-31 | Ucb Sa | Quinuclidine derivatives, processes for preparing them and their uses as m2 and/or m3 muscarinic receptor inhibitors |
| GB0125259D0 (en) | 2001-10-20 | 2001-12-12 | Glaxo Group Ltd | Novel compounds |
| MY130622A (en) | 2001-11-05 | 2007-07-31 | Novartis Ag | Naphthyridine derivatives, their preparation and their use as phosphodiesterase isoenzyme 4 (pde4) inhibitors |
| WO2003048181A1 (en) | 2001-12-01 | 2003-06-12 | Glaxo Group Limited | 17.alpha. -cyclic esters of 16-methylpregnan-3,20-dione as anti-inflammatory agents |
| PL211250B1 (pl) | 2001-12-20 | 2012-04-30 | Chiesi Farma Spa | Pochodne karbaminianu 1-alkilo-1-azoniabicyklo [2.2.2] oktanu, jej zastosowania, kompozycja farmaceutyczna zawierająca ten związek oraz związek pośredni |
| WO2003072592A1 (en) | 2002-01-15 | 2003-09-04 | Glaxo Group Limited | 17.alpha-cycloalkyl/cycloylkenyl esters of alkyl-or haloalkyl-androst-4-en-3-on-11.beta.,17.alpha.-diol 17.beta.-carboxylates as anti-inflammatory agents |
| WO2003062259A2 (en) | 2002-01-21 | 2003-07-31 | Glaxo Group Limited | Non-aromatic 17.alpha.-esters of androstane-17.beta.-carboxylate esters as anti-inflammatory agents |
| GB0202216D0 (en) | 2002-01-31 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| EP1490317A1 (en) | 2002-03-26 | 2004-12-29 | Boehringer Ingelheim Pharmaceuticals Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| HRP20040887A2 (en) | 2002-03-26 | 2005-04-30 | Boehringer Ingelheim Pharmaceuticals Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| US20090170803A1 (en) | 2002-04-10 | 2009-07-02 | Linden Joel M | Adjunctive treatment of biological diseases |
| ES2206021B1 (es) | 2002-04-16 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de pirrolidinio. |
| ES2201907B1 (es) | 2002-05-29 | 2005-06-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de indolilpiperidina como potentes agentes antihistaminicos y antialergicos. |
| DE10224888A1 (de) | 2002-06-05 | 2003-12-24 | Merck Patent Gmbh | Pyridazinderivate |
| US7074806B2 (en) | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| DE10225574A1 (de) | 2002-06-10 | 2003-12-18 | Merck Patent Gmbh | Aryloxime |
| DE10227269A1 (de) | 2002-06-19 | 2004-01-08 | Merck Patent Gmbh | Thiazolderivate |
| AU2003243870B2 (en) | 2002-06-25 | 2008-11-20 | Merck Frosst Canada Ltd | 8-(biaryl) quinoline PDE4 inhibitors |
| AU2003281219A1 (en) | 2002-07-02 | 2004-01-23 | Bernard Cote | Di-aryl-substituted-ethane pyridone pde4 inhibitors |
| ES2204295B1 (es) | 2002-07-02 | 2005-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de quinuclidina-amida. |
| AU2003281355A1 (en) | 2002-07-08 | 2004-01-23 | Pfizer Products Inc. | Modulators of the glucocorticoid receptor |
| AR040962A1 (es) | 2002-08-09 | 2005-04-27 | Novartis Ag | Compuestos derivados de tiazol 1,3-2-ona, composicion farmaceutica y proceso de preparacion del compuesto |
| BR0313330A (pt) | 2002-08-10 | 2005-06-14 | Altana Pharma Ag | Piperidina-ftalazonas substituìdas com pirrolidinadiona como inibidores de pde4 |
| AU2003260371A1 (en) | 2002-08-10 | 2004-03-11 | Altana Pharma Ag | Piperidine-n-oxide-derivatives |
| AU2003251693A1 (en) | 2002-08-10 | 2004-03-11 | Altana Pharma Ag | Pyridazinone-derivatives as pde4 inhibitors |
| WO2004018449A1 (en) | 2002-08-10 | 2004-03-04 | Altana Pharma Ag | Piperidine-derivatives as pde4 inhibitors |
| WO2004018431A2 (en) | 2002-08-17 | 2004-03-04 | Altana Pharma Ag | Novel phenanthridines |
| PL373598A1 (en) | 2002-08-17 | 2005-09-05 | Altana Pharma Ag | Novel benzonaphthyridines |
| SE0202483D0 (sv) | 2002-08-21 | 2002-08-21 | Astrazeneca Ab | Chemical compounds |
| ATE423769T1 (de) | 2002-08-23 | 2009-03-15 | Ranbaxy Lab Ltd | Fluor- und sulfonylaminohaltige, 3,6- disubstituierte azabicyclo 3.1.0 hexanderivate als muscarinrezeptorantagonisten |
| JP4587295B2 (ja) | 2002-08-29 | 2010-11-24 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｐｄｅ４インヒビターとしての３−ヒドロキシ−６−フェニルフェナントリジン |
| AU2003255493B8 (en) | 2002-08-29 | 2009-03-26 | Takeda Gmbh | 2-hydroxy-6-phenylphenanthridines as PDE-4 inhibitors |
| BR0313961A (pt) | 2002-08-30 | 2005-07-19 | Pfizer Prod Inc | Processos e intermediários para preparar triazolo-piridinas |
| KR20050057408A (ko) | 2002-09-18 | 2005-06-16 | 오노 야꾸힝 고교 가부시키가이샤 | 트리아자스피로[5.5]운데칸 유도체 및 이를 유효 성분으로하는 약제 |
| JP2006096662A (ja) | 2002-09-18 | 2006-04-13 | Sumitomo Pharmaceut Co Ltd | 新規６−置換ウラシル誘導体及びアレルギー性疾患の治療剤 |
| JP2004107299A (ja) | 2002-09-20 | 2004-04-08 | Japan Energy Corp | 新規１−置換ウラシル誘導体及びアレルギー性疾患の治療剤 |
| DE10246374A1 (de) | 2002-10-04 | 2004-04-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Betamimetika mit verlängerter Wirkungsdauer, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| ATE380185T1 (de) | 2002-10-23 | 2007-12-15 | Glenmark Pharmaceuticals Ltd | Tricyclische verbindungen zur behandlung von entzündlichen- und allergischen erkrankungen: verfahren zu deren herstellung und sie enthaltende pharmazeutische zusammensetzungen |
| GB0225540D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Medicinal compounds |
| GB0225535D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Medicinal compounds |
| DE10253282A1 (de) | 2002-11-15 | 2004-05-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittel zur Behandlung von chronisch obstruktiver Lungenerkrankung |
| DE10253426B4 (de) | 2002-11-15 | 2005-09-22 | Elbion Ag | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung |
| DE10253220A1 (de) | 2002-11-15 | 2004-05-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Dihydroxy-Methyl-Phenyl-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| JP2007524596A (ja) | 2003-02-28 | 2007-08-30 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | 共結晶医薬組成物 |
| WO2005007621A2 (en) | 2003-05-30 | 2005-01-27 | Rigel Pharmaceuticals, Inc. | Ubiquitin ligase inhibitors |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| US20050256309A1 (en) | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
| BRPI0514391A (pt) | 2004-08-18 | 2008-06-10 | Pharmacia & Upjohn Co Llc | compostos de triazolopiridina para o tratamento de inflamação |
| ATE479687T1 (de) | 2004-10-15 | 2010-09-15 | Takeda Pharmaceutical | Kinaseinhibitoren |
| US7456289B2 (en) | 2004-12-31 | 2008-11-25 | National Health Research Institutes | Anti-tumor compounds |
| US7579348B2 (en) | 2005-02-25 | 2009-08-25 | Pgxhealth, Llc | Derivatives of 8-substituted xanthines |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| US7632837B2 (en) | 2005-06-17 | 2009-12-15 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid-1 receptor modulators |
| UA98297C2 (en) | 2005-12-21 | 2012-05-10 | Янссен Фармацевтика, Н.В. | Triazolopyridazines as tyrosine kinase modulators |
| MX2008012485A (es) | 2006-03-30 | 2008-10-10 | Novartis Ag | Composiciones y metodos de uso para anticuerpos de c-met. |
| NL2000613C2 (nl) | 2006-05-11 | 2007-11-20 | Pfizer Prod Inc | Triazoolpyrazinederivaten. |
| JP2009538899A (ja) | 2006-05-30 | 2009-11-12 | ファイザー・プロダクツ・インク | トリアゾロピリダジン誘導体 |
| US8217177B2 (en) | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| PE20121506A1 (es) | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
| KR20090071612A (ko) * | 2006-10-23 | 2009-07-01 | 에스지엑스 파마슈티컬스, 인코포레이티드 | 단백질 키나제 조정제로서의 바이시클릭 트리아졸 |
| AU2007309237B2 (en) | 2006-10-23 | 2012-03-22 | Sgx Pharmaceuticals, Inc. | Triazolo-pyridazine protein kinase modulators |
| CA2669991C (en) | 2006-11-22 | 2016-01-26 | Incyte Corporation | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
| JP5548123B2 (ja) | 2007-06-21 | 2014-07-16 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ６−｛ジフルオロ［６−（１−メチル−１Ｈ−ピラゾル−４−イル）［１，２，４］トリアゾロ［４，３−ｂ］ピリダジン−３−イル］メチル｝キノリンの多形および水和物の形態、塩、ならびに製造方法 |
| PA8792501A1 (es) | 2007-08-09 | 2009-04-23 | Sanofi Aventis | Nuevos derivados de 6-triazolopiridacina-sulfanil benzotiazol y bencimidazol,su procedimiento de preparación,su aplicación como medicamentos,composiciones farmacéuticas y nueva utilización principalmente como inhibidores de met. |
| ES2635131T3 (es) | 2007-08-29 | 2017-10-02 | Methylgene Inc. | Inhibidores de la actividad de la proteína tirosina cinasa |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| US20110039856A1 (en) | 2007-11-29 | 2011-02-17 | Pfizer Inc. | Polymorphs of a c-met/hgfr inhibitor |
| CA2707712A1 (en) | 2007-12-06 | 2009-06-11 | Schering Corporation | Gamma secretase modulators |
| KR20100128305A (ko) | 2008-02-28 | 2010-12-07 | 노파르티스 아게 | Ｃ-ｍｅｔ 티로신 키나제 매개 질환의 치료를 위한 이미다조[1,2-ｂ]피리다진 유도체 |
| CA2724742C (en) | 2008-05-21 | 2016-07-19 | Incyte Corporation | Salts of 2-fluoro-n-methyl-4-[7-(quinolin-6-yl-methyl)- imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide and processes related to preparing the same |
| KR20110039558A (ko) | 2008-07-18 | 2011-04-19 | 사노피-아벤티스 | 신규 트리아졸로(4,3-ａ)피리딘 유도체, 그의 제조 방법, 의약으로서의 그의 용도, 제약 조성물, 및 특히 ｍｅｔ 억제제로서의 신규 용도 |
| UY32049A (es) | 2008-08-14 | 2010-03-26 | Takeda Pharmaceutical | Inhibidores de cmet |
| FR2941950B1 (fr) | 2009-02-06 | 2011-04-01 | Sanofi Aventis | Derives de 6-(6-o-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met. |
| FR2941951B1 (fr) | 2009-02-06 | 2011-04-01 | Sanofi Aventis | Derives de 6-(6-nh-substitue-triazolopyridazine-sulfanyl) benzothiazoles et benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met. |
| FR2941952B1 (fr) | 2009-02-06 | 2011-04-01 | Sanofi Aventis | Derives de 6-(6-substitue-triazolopyridazine-sulfanyl) 5-fluoro-benzothiazoles et 5-fluoro-benzimidazoles : preparation, application comme medicaments et utilisation comme inhibiteurs de met. |
| FR2941949B1 (fr) | 2009-02-06 | 2011-04-01 | Sanofi Aventis | Derives de 6-(6-o-cycloalkyl ou 6-nh-cycloalkyl- triazolopyridazine-sulfanyl)benzothiazoles et benzimidazoles preparation, application comme medicaments et utilisation comme inhibiteurs de met. |
| SG176021A1 (en) | 2009-05-12 | 2011-12-29 | Janssen Pharmaceuticals Inc | 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
| WO2010138673A1 (en) | 2009-05-28 | 2010-12-02 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-met protein kinase |
| CN102725290B (zh) | 2009-07-27 | 2016-03-09 | 吉利德科学股份有限公司 | 作为离子通道调节剂的稠合杂环化合物 |
| UA107360C2 (en) | 2009-08-05 | 2014-12-25 | Biogen Idec Inc | Bicyclic aryl sphingosine 1-phosphate analogs |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| EA201200260A1 (ru) | 2009-08-12 | 2012-09-28 | Новартис Аг | Гетероциклические гидразоны и их применение для лечения рака и воспаления |
| KR20120089463A (ko) * | 2009-08-20 | 2012-08-10 | 노파르티스 아게 | 헤테로시클릭 옥심 화합물 |
| AU2010343102B2 (en) | 2009-12-29 | 2016-03-24 | Dana-Farber Cancer Institute, Inc. | Type II Raf kinase inhibitors |
| BR112012020273A8 (pt) | 2010-02-11 | 2017-12-26 | Univ Vanderbilt | compostos de pirazolopiridina, pirazolopirazina, pirazolopirimidina, pirazolotiofeno e pirazolotiazol como pontencializadores alostéricos de mglur4, composições e métodos de tratamento de disfunção neurológica |
| US8299117B2 (en) | 2010-06-16 | 2012-10-30 | Metabolex Inc. | GPR120 receptor agonists and uses thereof |
| EP2425830A1 (en) | 2010-09-03 | 2012-03-07 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Synergistic drug combination for the treatment of cancer |
| CA2812744A1 (en) | 2010-09-27 | 2012-04-05 | Exelixis, Inc. | Dual inhibitors of met and vegf for the treatment of castration resistant prostate cancer and osteoblastic bone metastases |
| US20120100157A1 (en) | 2010-10-11 | 2012-04-26 | Van Andel Research Institute | Biomarker and Method for Predicting Sensitivity to MET Inhibitors |
| US20130324526A1 (en) | 2011-02-10 | 2013-12-05 | Novartis Ag | [1,2,4] triazolo [4,3-b] pyridazine compounds as inhibitors of the c-met tyrosine kinase |
-
2012
- 2012-09-13 AU AU2012310168A patent/AU2012310168B2/en not_active Ceased
- 2012-09-13 EA EA201490630A patent/EA026655B1/ru not_active IP Right Cessation
- 2012-09-13 EP EP12769172.3A patent/EP2755976B1/en not_active Not-in-force
- 2012-09-13 KR KR1020147009795A patent/KR20140077916A/ko not_active Withdrawn
- 2012-09-13 ES ES12769172.3T patent/ES2691650T3/es active Active
- 2012-09-13 WO PCT/IB2012/054775 patent/WO2013038362A1/en not_active Ceased
- 2012-09-13 US US13/613,291 patent/US9062045B2/en active Active
- 2012-09-13 BR BR112014006223A patent/BR112014006223A8/pt not_active IP Right Cessation
- 2012-09-13 CA CA2848809A patent/CA2848809A1/en not_active Abandoned
- 2012-09-13 JP JP2014530361A patent/JP5957526B2/ja not_active Expired - Fee Related
- 2012-09-13 MX MX2014003194A patent/MX339302B/es active IP Right Grant
- 2012-09-13 UY UY0001034329A patent/UY34329A/es not_active Application Discontinuation
- 2012-09-14 TW TW101133879A patent/TW201319067A/zh unknown
- 2012-09-14 AR ARP120103386A patent/AR087868A1/es unknown
-
2015
- 2015-05-19 US US14/716,159 patent/US9474762B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014526499A5 (enExample) | ||
| JP7624985B2 (ja) | Ｐｒｍｔ５阻害剤の組合せ医薬 | |
| KR102534028B1 (ko) | 트리아졸로피리미딘 화합물 및 그의 용도 | |
| ES2826950T3 (es) | Métodos para tratar cáncer y afecciones no neoplásicas | |
| IL297481A (en) | Halogenated heteroaryls and other heterocyclic kinase inhibitors, and uses thereof | |
| JP2017530999A5 (enExample) | ||
| JP2020526499A5 (enExample) | ||
| RU2014151009A (ru) | Пиразолопиримидоновые и пиразолопиридоновые ингибиторы танкиразы | |
| JP2009529047A5 (enExample) | ||
| SI3083625T1 (en) | Pyrimidopyrimidinones, useful as Wee-1 kinase inhibitors | |
| JP2013539777A5 (enExample) | ||
| RU2015148189A (ru) | ПРОИЗВОДНЫЕ 2-АМИДОПИРИДО[4, 3-d]ПИРИМИДИН-5-ОНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ WEE-1 | |
| CA2683641A1 (en) | Methods of treating cancer using pyridopyrimidinone inhibitors of pi3k alpha | |
| JP2013518892A5 (enExample) | ||
| JP2017510564A5 (enExample) | ||
| EP2739616A1 (en) | Pyridin-2(1h)-one derivatives as jak inhibitors | |
| BR112012022650B1 (pt) | Derivados de imidazo[1,2-a]pirazina, seu uso no tratamento ou na prevenção de distúrbios e doenças neurológicos, psiquiátricos ou metabólicos, composição farmacêutica que os compreende processo de preparação da mesma | |
| EP3691620A1 (en) | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd | |
| SI2790705T1 (en) | Use of activity inhibitors or PI3K function | |
| HRP20210931T1 (hr) | Alkil-amin harminski derivati za poticanje rasta kostiju | |
| RU2019123319A (ru) | Пиразолопиримидины и способы их применения | |
| WO2020206035A1 (en) | Treatment of cdk4/6 inhibitor resistant neoplastic disorders | |
| WO2019136244A1 (en) | Heterocyclic compounds for the treatment of abnormal cellular proliferation | |
| JP2019505595A5 (enExample) | ||
| JP2018526391A5 (enExample) |