JP2014526499A5 - - Google Patents
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- 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
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- 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
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| WO2014180182A1 (zh) * | 2013-05-10 | 2014-11-13 | 江苏豪森药业股份有限公司 | [1,2,4]三唑并[4,3-a]吡啶类衍生物，其制备方法或其在医药上的应用 |
| AU2014302595B2 (en) | 2013-06-24 | 2018-08-02 | 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 |
| WO2016015653A1 (zh) * | 2014-08-01 | 2016-02-04 | 江苏豪森药业股份有限公司 | C-Met抑制剂结晶型游离碱或其结晶型酸式盐及其制备方法和应用 |
| WO2017049711A1 (zh) | 2015-09-24 | 2017-03-30 | 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 |
| KR102709679B1 (ko) | 2018-04-25 | 2024-09-26 | 바이엘 악티엔게젤샤프트 | 살충제로서의 신규 헤테로아릴-트리아졸 및 헤테로아릴-테트라졸 화합물 |
| CN118561817A (zh) | 2019-07-23 | 2024-08-30 | 拜耳公司 | 作为农药的新的杂芳基-三唑化合物 |
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| 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 |
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2012
- 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 EA EA201490630A patent/EA026655B1/ru not_active IP Right Cessation
- 2012-09-13 US US13/613,291 patent/US9062045B2/en active Active
- 2012-09-13 AU AU2012310168A patent/AU2012310168B2/en not_active Ceased
- 2012-09-13 MX MX2014003194A patent/MX339302B/es active IP Right Grant
- 2012-09-13 WO PCT/IB2012/054775 patent/WO2013038362A1/en not_active Ceased
- 2012-09-13 BR BR112014006223A patent/BR112014006223A8/pt not_active IP Right Cessation
- 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 UY UY0001034329A patent/UY34329A/es not_active Application Discontinuation
- 2012-09-13 EP EP12769172.3A patent/EP2755976B1/en not_active Not-in-force
- 2012-09-14 TW TW101133879A patent/TW201319067A/zh unknown
- 2012-09-14 AR ARP120103386A patent/AR087868A1/es unknown
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2015
- 2015-05-19 US US14/716,159 patent/US9474762B2/en active Active
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