JP2016516724A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016516724A5 JP2016516724A5 JP2016503187A JP2016503187A JP2016516724A5 JP 2016516724 A5 JP2016516724 A5 JP 2016516724A5 JP 2016503187 A JP2016503187 A JP 2016503187A JP 2016503187 A JP2016503187 A JP 2016503187A JP 2016516724 A5 JP2016516724 A5 JP 2016516724A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methyl
- oxy
- carbamoyl
- pyrazol
- 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 46
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 33
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims 27
- -1 Heptanyl Chemical group 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 19
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 10
- DGOYLVBDCVINQZ-UHFFFAOYSA-N oxane-4-carboxamide Chemical compound NC(=O)C1CCOCC1 DGOYLVBDCVINQZ-UHFFFAOYSA-N 0.000 claims 9
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 claims 9
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 8
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 claims 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- MFNYBOWJWGPXFM-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1CCC1 MFNYBOWJWGPXFM-UHFFFAOYSA-N 0.000 claims 6
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 6
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- VEKIYFGCEAJDDT-UHFFFAOYSA-N 2-pyridin-3-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1 VEKIYFGCEAJDDT-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229940047889 isobutyramide Drugs 0.000 claims 3
- NJYYWQHQUOODDL-UHFFFAOYSA-N oxetane-3-carboxamide Chemical compound NC(=O)C1COC1 NJYYWQHQUOODDL-UHFFFAOYSA-N 0.000 claims 3
- DUXPFRRFZLRICX-UHFFFAOYSA-N oxolane-3-carboxamide Chemical compound NC(=O)C1CCOC1 DUXPFRRFZLRICX-UHFFFAOYSA-N 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- BRTPVCOSAMSGGP-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(1-methylimidazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CN1C=NC(C=2N=CC=C(OC=3C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=3)C=2)=C1 BRTPVCOSAMSGGP-UHFFFAOYSA-N 0.000 claims 2
- NYLABMCASIBMHG-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(2-methyl-1,3-oxazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound O1C(C)=NC=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)=CC=N1 NYLABMCASIBMHG-UHFFFAOYSA-N 0.000 claims 2
- ZRFHSNCTTQYYMI-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(4-methylimidazol-1-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(C)=CN1C1=CC(OC=2C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)=CC=N1 ZRFHSNCTTQYYMI-UHFFFAOYSA-N 0.000 claims 2
- WYLCQKJYTVNVCY-UHFFFAOYSA-N 2,2-dimethyl-n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)(C)C)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 WYLCQKJYTVNVCY-UHFFFAOYSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 210000000988 bone and bone Anatomy 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 230000009401 metastasis Effects 0.000 claims 2
- 208000037819 metastatic cancer Diseases 0.000 claims 2
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims 2
- JBPWJPNLAGHYOY-UHFFFAOYSA-N n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxane-4-carboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(C)=NC=1NC(=O)NC(=O)C1CCOCC1 JBPWJPNLAGHYOY-UHFFFAOYSA-N 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 239000008177 pharmaceutical agent Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- INYOCBFRHKLUEG-UHFFFAOYSA-N 2,2-dimethyl-n-[[4-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=CC(NC(=O)NC(=O)C(C)(C)C)=NC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 INYOCBFRHKLUEG-UHFFFAOYSA-N 0.000 claims 1
- CBCSZVKFKFFDGE-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(1,3-oxazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)(C)C)=CC=C1OC1=CC=NC(C=2OC=NC=2)=C1 CBCSZVKFKFFDGE-UHFFFAOYSA-N 0.000 claims 1
- DIEZYKBKDPYDRO-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(1,3-thiazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)(C)C)=CC=C1OC1=CC=NC(C=2SC=NC=2)=C1 DIEZYKBKDPYDRO-UHFFFAOYSA-N 0.000 claims 1
- XZASYTCIZJBGEJ-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyrazin-2-yl]carbamoyl]propanamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2N=CC(NC(=O)NC(=O)C(C)(C)C)=NC=2)=CC=N1 XZASYTCIZJBGEJ-UHFFFAOYSA-N 0.000 claims 1
- MKDGTXKQCIZABO-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)=CC=N1 MKDGTXKQCIZABO-UHFFFAOYSA-N 0.000 claims 1
- NBPDPKZMZSVBEA-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(2-methyl-1,3-thiazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound S1C(C)=NC=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)=CC=N1 NBPDPKZMZSVBEA-UHFFFAOYSA-N 0.000 claims 1
- JXQMKLWLSBXRRW-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(2-methylpyridin-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(C)=CC(C=2N=CC=C(OC=3C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=3)C=2)=C1 JXQMKLWLSBXRRW-UHFFFAOYSA-N 0.000 claims 1
- YGLZANSXSZTVCB-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(2-propan-2-yl-1h-imidazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound N1C(C(C)C)=NC(C=2N=CC=C(OC=3C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=3)C=2)=C1 YGLZANSXSZTVCB-UHFFFAOYSA-N 0.000 claims 1
- BSODMZFPWQTRAC-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-(6-methylpyridin-3-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(C)=CC=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)=CC=N1 BSODMZFPWQTRAC-UHFFFAOYSA-N 0.000 claims 1
- WAPRLBOJLJINDO-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-[2-(trifluoromethyl)pyridin-4-yl]pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)(C)C)=CC=C1OC1=CC=NC(C=2C=C(N=CC=2)C(F)(F)F)=C1 WAPRLBOJLJINDO-UHFFFAOYSA-N 0.000 claims 1
- SZIYVAADDQWKPT-UHFFFAOYSA-N 2,2-dimethyl-n-[[5-[2-[6-(methylamino)pyridin-3-yl]pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC)=CC=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)=CC=N1 SZIYVAADDQWKPT-UHFFFAOYSA-N 0.000 claims 1
- NFNARGXPERSTRO-UHFFFAOYSA-N 2,2-dimethyl-n-[[6-methyl-5-[2-(1,3-thiazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)(C)C)=CC=C1OC1=CC=NC(C=2SC=NC=2)=C1 NFNARGXPERSTRO-UHFFFAOYSA-N 0.000 claims 1
- ADDLUHNUHVANBB-UHFFFAOYSA-N 2,2-dimethyl-n-[[6-methyl-5-[2-(2-methylpyridin-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(C)=CC(C=2N=CC=C(OC=3C(=NC(NC(=O)NC(=O)C(C)(C)C)=CC=3)C)C=2)=C1 ADDLUHNUHVANBB-UHFFFAOYSA-N 0.000 claims 1
- NDJZLUADNRFQLF-UHFFFAOYSA-N 2,2-dimethyl-n-[[6-methyl-5-[2-(2h-triazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)(C)C)=CC=C1OC1=CC=NC(C=2N=NNC=2)=C1 NDJZLUADNRFQLF-UHFFFAOYSA-N 0.000 claims 1
- ZOILYTDFDBVEJB-UHFFFAOYSA-N 2,2-dimethyl-n-[[6-methyl-5-[2-(3-methyl-1,2-oxazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound O1N=C(C)C=C1C1=CC(OC=2C(=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)C)=CC=N1 ZOILYTDFDBVEJB-UHFFFAOYSA-N 0.000 claims 1
- KIHSCGHJPZKOHN-UHFFFAOYSA-N 2,2-dimethyl-n-[[6-methyl-5-[2-(6-methylpyridin-3-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(C)=CC=C1C1=CC(OC=2C(=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)C)=CC=N1 KIHSCGHJPZKOHN-UHFFFAOYSA-N 0.000 claims 1
- IELZFJBBJXHQIN-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)pyridine Chemical compound C1=NN(C)C=C1C1=CC=CC=N1 IELZFJBBJXHQIN-UHFFFAOYSA-N 0.000 claims 1
- KSSHHZCXNZJPHQ-UHFFFAOYSA-N 2-(4-methylimidazol-1-yl)pyridine Chemical compound C1=NC(C)=CN1C1=CC=CC=N1 KSSHHZCXNZJPHQ-UHFFFAOYSA-N 0.000 claims 1
- IFXJTSUVTOQZBW-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]acetamide Chemical compound C1CN(C)CCN1CC(=O)NC(=O)NC(N=C1)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 IFXJTSUVTOQZBW-UHFFFAOYSA-N 0.000 claims 1
- PQWTZOBWEFDCBW-UHFFFAOYSA-N 2-cyano-2-methyl-n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C(C)(C)C#N)=CC=2)=CC=N1 PQWTZOBWEFDCBW-UHFFFAOYSA-N 0.000 claims 1
- IVCPMLJAAZSIJH-UHFFFAOYSA-N 2-methoxy-2-methyl-n-[[5-[2-(1-prop-2-enylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)(C)OC)=CC=C1OC1=CC=NC(C2=CN(CC=C)N=C2)=C1 IVCPMLJAAZSIJH-UHFFFAOYSA-N 0.000 claims 1
- OLNMYSWEQROCQP-UHFFFAOYSA-N 2-methoxy-2-methyl-n-[[5-[2-(2-propan-2-yl-1h-imidazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)(C)OC)=CC=C1OC1=CC=NC(C=2NC(=NC=2)C(C)C)=C1 OLNMYSWEQROCQP-UHFFFAOYSA-N 0.000 claims 1
- FJHKXJRUWMFKAQ-UHFFFAOYSA-N 2-methoxy-n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]acetamide Chemical compound C1=NC(NC(=O)NC(=O)COC)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 FJHKXJRUWMFKAQ-UHFFFAOYSA-N 0.000 claims 1
- ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 2-methyl-1,3-oxazole Chemical compound CC1=NC=CO1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 claims 1
- HKYYIBYHSLENRI-UHFFFAOYSA-N 2-methyl-n-[[4-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)C)=CC(C)=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 HKYYIBYHSLENRI-UHFFFAOYSA-N 0.000 claims 1
- KVFPOPHEODUHNQ-UHFFFAOYSA-N 2-methyl-n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxy-6-(trifluoromethyl)pyridin-2-yl]carbamoyl]propanamide Chemical compound FC(F)(F)C1=NC(NC(=O)NC(=O)C(C)C)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 KVFPOPHEODUHNQ-UHFFFAOYSA-N 0.000 claims 1
- XFNDWSBFMWBPKL-UHFFFAOYSA-N 2-methyl-n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)C)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 XFNDWSBFMWBPKL-UHFFFAOYSA-N 0.000 claims 1
- HVZYXMRMYSBLOJ-UHFFFAOYSA-N 2-methyl-n-[[5-[2-[4-(1-methylpiperidin-4-yl)phenyl]pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)C)=CC=C1OC1=CC=NC(C=2C=CC(=CC=2)C2CCN(C)CC2)=C1 HVZYXMRMYSBLOJ-UHFFFAOYSA-N 0.000 claims 1
- LDFPZTVJHCRSKV-UHFFFAOYSA-N 2-methyl-n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)C)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 LDFPZTVJHCRSKV-UHFFFAOYSA-N 0.000 claims 1
- ALOOSUWFQSUMTE-UHFFFAOYSA-N 2-methyl-n-[[6-methyl-5-[2-(2-methylpyridin-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)C)=CC=C1OC1=CC=NC(C=2C=C(C)N=CC=2)=C1 ALOOSUWFQSUMTE-UHFFFAOYSA-N 0.000 claims 1
- ODJAXFWFGLUMHX-UHFFFAOYSA-N 2-methyl-n-[[6-methyl-5-[2-(2-morpholin-4-ylpyridin-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)C)=CC=C1OC1=CC=NC(C=2C=C(N=CC=2)N2CCOCC2)=C1 ODJAXFWFGLUMHX-UHFFFAOYSA-N 0.000 claims 1
- KSPXNHRXBOCKPK-UHFFFAOYSA-N 2-methyl-n-[[6-methyl-5-[2-(4-methylimidazol-1-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)C)=CC=C1OC1=CC=NC(N2C=C(C)N=C2)=C1 KSPXNHRXBOCKPK-UHFFFAOYSA-N 0.000 claims 1
- HUPNQNOWXCVQSW-UHFFFAOYSA-N 2h-pyran-4-carboxamide Chemical group NC(=O)C1=CCOC=C1 HUPNQNOWXCVQSW-UHFFFAOYSA-N 0.000 claims 1
- PXHUOXDIABIOMP-UHFFFAOYSA-N 3,3-dimethyl-n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]cyclobutane-1-carboxamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3CC(C)(C)C3)=CC=2)=CC=N1 PXHUOXDIABIOMP-UHFFFAOYSA-N 0.000 claims 1
- OKPFGTDSHOBKHS-UHFFFAOYSA-N 3,3-dimethyl-n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]cyclobutane-1-carboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(C)=NC=1NC(=O)NC(=O)C1CC(C)(C)C1 OKPFGTDSHOBKHS-UHFFFAOYSA-N 0.000 claims 1
- JUCFTBRYHOEXJD-UHFFFAOYSA-N 3,3-dimethyl-n-[[6-methyl-5-[2-(3-methyl-1,2-oxazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]cyclobutane-1-carboxamide Chemical compound O1N=C(C)C=C1C1=CC(OC=2C(=NC(NC(=O)NC(=O)C3CC(C)(C)C3)=CC=2)C)=CC=N1 JUCFTBRYHOEXJD-UHFFFAOYSA-N 0.000 claims 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 1
- 208000036487 Arthropathies Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000012659 Joint disease Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010033701 Papillary thyroid cancer Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- CKBZJTAMRPPVSR-UHFFFAOYSA-N adamantane-1-carboxamide Chemical compound C1C(C2)CC3CC2CC1(C(=O)N)C3 CKBZJTAMRPPVSR-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- SLOPJPLJISGXPG-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3-carboxamide Chemical compound C1CC2C(C(=O)N)CC1C2 SLOPJPLJISGXPG-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 208000000516 mast-cell leukemia Diseases 0.000 claims 1
- 208000008585 mastocytosis Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- MJWRDAJAIUBORD-UHFFFAOYSA-N n-[[4,6-dimethyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]-2-methoxy-2-methylpropanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)(C)OC)=CC(C)=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 MJWRDAJAIUBORD-UHFFFAOYSA-N 0.000 claims 1
- SWAYROGPJDDZJL-UHFFFAOYSA-N n-[[5-[2-(1-ethylpyrazol-4-yl)pyridin-4-yl]oxy-6-methylpyridin-2-yl]carbamoyl]-2,2-dimethylpropanamide Chemical compound C1=NN(CC)C=C1C1=CC(OC=2C(=NC(NC(=O)NC(=O)C(C)(C)C)=CC=2)C)=CC=N1 SWAYROGPJDDZJL-UHFFFAOYSA-N 0.000 claims 1
- OBCCJEFBSGLDHV-UHFFFAOYSA-N n-[[5-[2-(1-ethylpyrazol-4-yl)pyridin-4-yl]oxy-6-methylpyridin-2-yl]carbamoyl]-2-methylpropanamide Chemical compound C1=NN(CC)C=C1C1=CC(OC=2C(=NC(NC(=O)NC(=O)C(C)C)=CC=2)C)=CC=N1 OBCCJEFBSGLDHV-UHFFFAOYSA-N 0.000 claims 1
- CPJVNCFEWBCEMO-UHFFFAOYSA-N n-[[5-[2-(1-ethylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]-2-methoxy-2-methylpropanamide Chemical compound C1=NN(CC)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C(C)(C)OC)=CC=2)=CC=N1 CPJVNCFEWBCEMO-UHFFFAOYSA-N 0.000 claims 1
- YUSGQAXWYNBVPF-UHFFFAOYSA-N n-[[5-[2-(1-methylimidazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)CC)=CC=C1OC1=CC=NC(C=2N=CN(C)C=2)=C1 YUSGQAXWYNBVPF-UHFFFAOYSA-N 0.000 claims 1
- XSVIDMSIUPEDST-UHFFFAOYSA-N n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]-3-[1-(trifluoromethyl)cyclopropyl]propanamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)CCC3(CC3)C(F)(F)F)=CC=2)=CC=N1 XSVIDMSIUPEDST-UHFFFAOYSA-N 0.000 claims 1
- CHLMGVCSHPBDFV-UHFFFAOYSA-N n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]bicyclo[2.2.2]octane-3-carboxamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3C4CCC(CC4)C3)=CC=2)=CC=N1 CHLMGVCSHPBDFV-UHFFFAOYSA-N 0.000 claims 1
- CYYZUMIHIONXRB-UHFFFAOYSA-N n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]cyclopentanecarboxamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3CCCC3)=CC=2)=CC=N1 CYYZUMIHIONXRB-UHFFFAOYSA-N 0.000 claims 1
- WTUUFVYRXMCOMT-UHFFFAOYSA-N n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]cyclopropanecarboxamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3CC3)=CC=2)=CC=N1 WTUUFVYRXMCOMT-UHFFFAOYSA-N 0.000 claims 1
- PQKLXEKKGWRTFF-UHFFFAOYSA-N n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxolane-3-carboxamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3COCC3)=CC=2)=CC=N1 PQKLXEKKGWRTFF-UHFFFAOYSA-N 0.000 claims 1
- PFYNHMCXAHRAPA-UHFFFAOYSA-N n-[[5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]spiro[3.3]heptane-2-carboxamide Chemical compound C1=NN(C)C=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3CC4(CCC4)C3)=CC=2)=CC=N1 PFYNHMCXAHRAPA-UHFFFAOYSA-N 0.000 claims 1
- KZMHNXRQTFMRLH-UHFFFAOYSA-N n-[[5-[2-(2,3-dimethylimidazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]-2-methoxy-2-methylpropanamide Chemical compound C1=NC(NC(=O)NC(=O)C(C)(C)OC)=CC=C1OC1=CC=NC(C=2N(C(C)=NC=2)C)=C1 KZMHNXRQTFMRLH-UHFFFAOYSA-N 0.000 claims 1
- WQEKAPPVDIAHIO-UHFFFAOYSA-N n-[[5-[2-(2-methyl-1,3-thiazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxane-4-carboxamide Chemical compound S1C(C)=NC=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3CCOCC3)=CC=2)=CC=N1 WQEKAPPVDIAHIO-UHFFFAOYSA-N 0.000 claims 1
- VTXUQMCYQOMNSC-UHFFFAOYSA-N n-[[5-[2-(2-methyl-1,3-thiazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxolane-3-carboxamide Chemical compound S1C(C)=NC=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3COCC3)=CC=2)=CC=N1 VTXUQMCYQOMNSC-UHFFFAOYSA-N 0.000 claims 1
- PKLAIKPRJRSVBW-UHFFFAOYSA-N n-[[5-[2-(2-methyl-1,3-thiazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)CC)=CC=C1OC1=CC=NC(C=2SC(C)=NC=2)=C1 PKLAIKPRJRSVBW-UHFFFAOYSA-N 0.000 claims 1
- ITIAFEQBLVZOBG-UHFFFAOYSA-N n-[[5-[2-(2-methylpyridin-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxolane-3-carboxamide Chemical compound C1=NC(C)=CC(C=2N=CC=C(OC=3C=NC(NC(=O)NC(=O)C4COCC4)=CC=3)C=2)=C1 ITIAFEQBLVZOBG-UHFFFAOYSA-N 0.000 claims 1
- SOAMVNMBBYDIDG-UHFFFAOYSA-N n-[[5-[2-(3-ethyl-2-propan-2-ylimidazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]-2,2-dimethylpropanamide Chemical compound N1=C(C(C)C)N(CC)C(C=2N=CC=C(OC=3C=NC(NC(=O)NC(=O)C(C)(C)C)=CC=3)C=2)=C1 SOAMVNMBBYDIDG-UHFFFAOYSA-N 0.000 claims 1
- JOXWBSJXHTVBJB-UHFFFAOYSA-N n-[[5-[2-(4-methylimidazol-1-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound C1=NC(NC(=O)NC(=O)CC)=CC=C1OC1=CC=NC(N2C=C(C)N=C2)=C1 JOXWBSJXHTVBJB-UHFFFAOYSA-N 0.000 claims 1
- JLJTXSWFIUFWSK-UHFFFAOYSA-N n-[[5-[2-(6-cyanopyridin-3-yl)pyridin-4-yl]oxy-6-methylpyridin-2-yl]carbamoyl]-2,2-dimethylpropanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)(C)C)=CC=C1OC1=CC=NC(C=2C=NC(=CC=2)C#N)=C1 JLJTXSWFIUFWSK-UHFFFAOYSA-N 0.000 claims 1
- CSRQFMWMJIWJEB-UHFFFAOYSA-N n-[[5-[2-(6-cyanopyridin-3-yl)pyridin-4-yl]oxy-6-methylpyridin-2-yl]carbamoyl]-2-methoxy-2-methylpropanamide Chemical compound CC1=NC(NC(=O)NC(=O)C(C)(C)OC)=CC=C1OC1=CC=NC(C=2C=NC(=CC=2)C#N)=C1 CSRQFMWMJIWJEB-UHFFFAOYSA-N 0.000 claims 1
- OJYAXUGTMORLDI-UHFFFAOYSA-N n-[[5-[2-(6-methylpyridin-3-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxolane-3-carboxamide Chemical compound C1=NC(C)=CC=C1C1=CC(OC=2C=NC(NC(=O)NC(=O)C3COCC3)=CC=2)=CC=N1 OJYAXUGTMORLDI-UHFFFAOYSA-N 0.000 claims 1
- AYTGALDGLVMBEH-UHFFFAOYSA-N n-[[6-ethyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]-1-methoxycyclopropane-1-carboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(CC)=NC=1NC(=O)NC(=O)C1(OC)CC1 AYTGALDGLVMBEH-UHFFFAOYSA-N 0.000 claims 1
- URZFDLKDKFIRGI-UHFFFAOYSA-N n-[[6-ethyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]-2,2-dimethylpropanamide Chemical compound CCC1=NC(NC(=O)NC(=O)C(C)(C)C)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 URZFDLKDKFIRGI-UHFFFAOYSA-N 0.000 claims 1
- FEBGDFNYJZZZOY-UHFFFAOYSA-N n-[[6-ethyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]-4-methyloxane-4-carboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(CC)=NC=1NC(=O)NC(=O)C1(C)CCOCC1 FEBGDFNYJZZZOY-UHFFFAOYSA-N 0.000 claims 1
- BONUGDQBMCJPHY-UHFFFAOYSA-N n-[[6-ethyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxane-4-carboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(CC)=NC=1NC(=O)NC(=O)C1CCOCC1 BONUGDQBMCJPHY-UHFFFAOYSA-N 0.000 claims 1
- LGLOIXLLAQLSAK-UHFFFAOYSA-N n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]adamantane-1-carboxamide Chemical compound CC1=NC(NC(=O)NC(=O)C23CC4CC(CC(C4)C2)C3)=CC=C1OC(C=1)=CC=NC=1C=1C=NN(C)C=1 LGLOIXLLAQLSAK-UHFFFAOYSA-N 0.000 claims 1
- USQDNKJTXHBZRC-UHFFFAOYSA-N n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]cyclobutanecarboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(C)=NC=1NC(=O)NC(=O)C1CCC1 USQDNKJTXHBZRC-UHFFFAOYSA-N 0.000 claims 1
- NCPIMEOPSFOWKB-UHFFFAOYSA-N n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]cyclohexanecarboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(C)=NC=1NC(=O)NC(=O)C1CCCCC1 NCPIMEOPSFOWKB-UHFFFAOYSA-N 0.000 claims 1
- KJAYIINCKQSQGA-UHFFFAOYSA-N n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]cyclopropanecarboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(C)=NC=1NC(=O)NC(=O)C1CC1 KJAYIINCKQSQGA-UHFFFAOYSA-N 0.000 claims 1
- BKRXMWPXDQLCFW-UHFFFAOYSA-N n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxolane-3-carboxamide Chemical compound C=1C=C(OC=2C=C(N=CC=2)C2=CN(C)N=C2)C(C)=NC=1NC(=O)NC(=O)C1CCOC1 BKRXMWPXDQLCFW-UHFFFAOYSA-N 0.000 claims 1
- GVVUWWVPVSPFNT-UHFFFAOYSA-N n-[[6-methyl-5-[2-(1-methylpyrazol-4-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]propanamide Chemical compound CC1=NC(NC(=O)NC(=O)CC)=CC=C1OC1=CC=NC(C2=CN(C)N=C2)=C1 GVVUWWVPVSPFNT-UHFFFAOYSA-N 0.000 claims 1
- XMAFTYGJAJOGAU-UHFFFAOYSA-N n-[[6-methyl-5-[2-(2-methyl-1,3-thiazol-5-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxane-4-carboxamide Chemical compound S1C(C)=NC=C1C1=CC(OC=2C(=NC(NC(=O)NC(=O)C3CCOCC3)=CC=2)C)=CC=N1 XMAFTYGJAJOGAU-UHFFFAOYSA-N 0.000 claims 1
- CIWWPSFWDAVLGU-UHFFFAOYSA-N n-[[6-methyl-5-[2-(4-methylimidazol-1-yl)pyridin-4-yl]oxypyridin-2-yl]carbamoyl]oxane-4-carboxamide Chemical compound C1=NC(C)=CN1C1=CC(OC=2C(=NC(NC(=O)NC(=O)C3CCOCC3)=CC=2)C)=CC=N1 CIWWPSFWDAVLGU-UHFFFAOYSA-N 0.000 claims 1
- 201000008383 nephritis Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- RAJQGFBSDVPCSD-UHFFFAOYSA-N spiro[3.3]heptane-2-carboxamide Chemical compound C1C(C(=O)N)CC11CCC1 RAJQGFBSDVPCSD-UHFFFAOYSA-N 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361789971P | 2013-03-15 | 2013-03-15 | |
| US61/789,971 | 2013-03-15 | ||
| PCT/US2014/029664 WO2014145028A2 (en) | 2013-03-15 | 2014-03-14 | N-acyl-n'-(pyridin-2-yl) ureas and analogs exhibiting anti-cancer and anti-proliferative activities |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018126337A Division JP2018184416A (ja) | 2013-03-15 | 2018-07-02 | 抗がんおよび抗増殖活性を示すｎ−アシル−ｎ’−（ピリジン−２−イル）尿素および類似体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016516724A JP2016516724A (ja) | 2016-06-09 |
| JP2016516724A5 true JP2016516724A5 (enExample) | 2017-04-20 |
| JP6364472B2 JP6364472B2 (ja) | 2018-07-25 |
Family
ID=51529946
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016503187A Active JP6364472B2 (ja) | 2013-03-15 | 2014-03-14 | 抗がんおよび抗増殖活性を示すｎ−アシル−ｎ’−（ピリジン−２−イル）尿素および類似体 |
| JP2018126337A Pending JP2018184416A (ja) | 2013-03-15 | 2018-07-02 | 抗がんおよび抗増殖活性を示すｎ−アシル−ｎ’−（ピリジン−２−イル）尿素および類似体 |
| JP2020068792A Active JP6985448B2 (ja) | 2013-03-15 | 2020-04-07 | 抗がんおよび抗増殖活性を示すｎ−アシル−ｎ’−（ピリジン−２−イル）尿素および類似体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018126337A Pending JP2018184416A (ja) | 2013-03-15 | 2018-07-02 | 抗がんおよび抗増殖活性を示すｎ−アシル−ｎ’−（ピリジン−２−イル）尿素および類似体 |
| JP2020068792A Active JP6985448B2 (ja) | 2013-03-15 | 2020-04-07 | 抗がんおよび抗増殖活性を示すｎ−アシル−ｎ’−（ピリジン−２−イル）尿素および類似体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9382228B2 (enExample) |
| EP (1) | EP2968287B1 (enExample) |
| JP (3) | JP6364472B2 (enExample) |
| KR (2) | KR102386952B1 (enExample) |
| CN (3) | CN112047927A (enExample) |
| AU (2) | AU2014233414B2 (enExample) |
| BR (1) | BR112015022263B1 (enExample) |
| CA (1) | CA2903288C (enExample) |
| ES (1) | ES2817902T3 (enExample) |
| IL (2) | IL241523B (enExample) |
| MX (2) | MX366429B (enExample) |
| PH (2) | PH12015502336B1 (enExample) |
| RU (1) | RU2769607C2 (enExample) |
| SG (1) | SG11201508532VA (enExample) |
| WO (1) | WO2014145028A2 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5335056B2 (ja) | 2011-11-16 | 2013-11-06 | 住友電気工業株式会社 | ボルト用アルミニウム合金線及びボルト並びにそれらの製造方法 |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| CN112047927A (zh) * | 2013-03-15 | 2020-12-08 | 德西费拉制药有限责任公司 | 展现抗癌和抗增殖活性的n-酰基-n′-(吡啶-2-基)脲及类似物 |
| TWI854164B (zh) * | 2016-02-01 | 2024-09-01 | 美商百歐克斯製藥公司 | 苯并吡唑化合物及其類似物 |
| KR101691954B1 (ko) * | 2016-04-26 | 2017-01-02 | 고려대학교 산학협력단 | 신규 n-아실유레아 유도체 및 이를 함유하는 심혈관질환의 예방 또는 치료용 조성물 |
| KR102374012B1 (ko) | 2017-05-24 | 2022-03-14 | 아비스코 테라퓨틱스 컴퍼니 리미티드 | N-(아자릴)시클로락탐-1-카르복사미드 유도체 및 합성법과 그 용법 |
| CN110461849B (zh) * | 2017-06-19 | 2020-09-01 | 上海和誉生物医药科技有限公司 | 一种csf1r抑制剂及其制备方法和应用 |
| KR20200040295A (ko) * | 2017-08-24 | 2020-04-17 | 메르크 파텐트 게엠베하 | 보론산 유도체 |
| CN109776401A (zh) * | 2017-11-14 | 2019-05-21 | 成都博腾药业有限公司 | 一种制备6-氯-5-三氟甲基-2-氨基吡啶的方法 |
| EP3746059A1 (en) | 2018-01-31 | 2020-12-09 | Deciphera Pharmaceuticals, LLC | Combination therapy for the treatment of gastrointestinal stromal tumors |
| WO2019152719A1 (en) | 2018-01-31 | 2019-08-08 | Deciphera Pharmaceuticals, Llc | Combination therapy for the treatment of mastocytosis |
| CN110845476B (zh) * | 2018-08-21 | 2022-11-18 | 上海和誉生物医药科技有限公司 | 一种高选择性csf1r抑制剂、其制备方法和在药学上的应用 |
| EP4303583B1 (en) | 2018-12-28 | 2025-07-23 | Deciphera Pharmaceuticals, LLC | Csf1r inhibitors for use in treating tenosynovial giant cell tumors |
| FI3921030T3 (fi) * | 2019-02-06 | 2024-01-08 | Lilly Co Eli | 1-((2-(2,2,2-trifluorietoksi)pyridin-4-yyli)metyyli)ureajohdannaisia kcnq:n tehostajina |
| US12509456B2 (en) | 2019-03-11 | 2025-12-30 | Deciphera Pharmaceuticals, Llc | Solid state forms of ripretinib |
| CN118930524A (zh) | 2019-05-10 | 2024-11-12 | 德西费拉制药有限责任公司 | 苯基氨基嘧啶酰胺自噬抑制剂及其使用方法 |
| SG11202112171XA (en) | 2019-05-10 | 2021-12-30 | Deciphera Pharmaceuticals Llc | Heteroarylaminopyrimidine amide autophagy inhibitors and methods of use thereof |
| AU2020297422B2 (en) | 2019-06-17 | 2024-03-21 | Deciphera Pharmaceuticals, Llc | Aminopyrimidine amide autophagy inhibitors and methods of use thereof |
| TWI878335B (zh) | 2019-08-12 | 2025-04-01 | 美商迪賽孚爾製藥有限公司 | 治療胃腸道基質瘤方法 |
| CA3150433A1 (en) | 2019-08-12 | 2021-02-18 | Deciphera Pharmaceuticals, Llc | Ripretinib for treating gastrointestinal stromal tumors |
| DK4084779T3 (da) | 2019-12-30 | 2024-12-16 | Deciphera Pharmaceuticals Llc | Sammensætninger af 1-(4-brom-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro- 1,6-naphthyridin-3-yl)-2-fluorphenyl)-3-phenylurea |
| CN119970649A (zh) | 2019-12-30 | 2025-05-13 | 德西费拉制药有限责任公司 | 非晶型激酶抑制剂制剂及其使用方法 |
| EP4247795A1 (en) | 2020-11-18 | 2023-09-27 | Deciphera Pharmaceuticals, LLC | Gcn2 and perk kinase inhibitors and methods of use thereof |
| WO2022247786A1 (zh) * | 2021-05-24 | 2022-12-01 | 上海和誉生物医药科技有限公司 | 一种结晶型csf-1r抑制剂酸式盐及其制备方法和应用 |
| CN115385896B (zh) * | 2021-05-24 | 2024-11-15 | 上海和誉生物医药科技有限公司 | 一种csf-1r抑制剂中间体或其酸式盐的制备方法 |
| EP4444429A1 (en) | 2021-12-09 | 2024-10-16 | Deciphera Pharmaceuticals, LLC | Raf kinase inhibitors and methods of use thereof |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
| US20250205161A1 (en) | 2023-12-08 | 2025-06-26 | Deciphera Pharmaceuticals, Llc | Formulations of vimseltinib |
| WO2025231106A1 (en) | 2024-05-01 | 2025-11-06 | Deciphera Pharmaceuticals, Llc | Csf-1r inhibitors and methods of use thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE860511L (en) * | 1985-03-01 | 1986-09-01 | Alfa Farmaceutici Spa | "Benzoyl urea derivatives having anti-tumor activity" |
| DE60233736D1 (de) * | 2001-06-22 | 2009-10-29 | Kirin Pharma K K | Chinolinderivat und chinazolinderivat, die die selbstphosphorylierung des hepatocytus-proliferator-rezeptors hemmen, und diese enthaltende medizinische zusammensetzung |
| ES2364901T3 (es) * | 2005-11-15 | 2011-09-16 | Array Biopharma, Inc. | Procesos e intermedios para la preparación de derivados de n4-fenil-quinazolin-4-amina. |
| WO2008046216A1 (en) * | 2006-10-18 | 2008-04-24 | Methylgene, Inc. | Kinase inhibitors and uses thereof |
| WO2008079291A2 (en) * | 2006-12-20 | 2008-07-03 | Amgen Inc. | Substituted heterocycles and methods of use |
| CL2008002793A1 (es) * | 2007-09-20 | 2009-09-04 | Cgi Pharmaceuticals Inc | Compuestos derivados de amidas sustituidas, inhibidores de la actividad de btk; composicion farmaceutica que los comprende; utiles en el tratamiento del cancer, trastornos oseos, enfermedades autoinmunes, entre otras |
| CA2742007C (en) * | 2008-10-29 | 2014-07-08 | Deciphera Pharmaceuticals, Llc | Cyclopropane amides and analogs exhibiting anti-cancer and anti-proliferative activities |
| CN112047927A (zh) * | 2013-03-15 | 2020-12-08 | 德西费拉制药有限责任公司 | 展现抗癌和抗增殖活性的n-酰基-n′-(吡啶-2-基)脲及类似物 |
-
2014
- 2014-03-14 CN CN202010826889.4A patent/CN112047927A/zh active Pending
- 2014-03-14 MX MX2015013404A patent/MX366429B/es active IP Right Grant
- 2014-03-14 US US14/214,185 patent/US9382228B2/en active Active
- 2014-03-14 CA CA2903288A patent/CA2903288C/en active Active
- 2014-03-14 WO PCT/US2014/029664 patent/WO2014145028A2/en not_active Ceased
- 2014-03-14 PH PH1/2015/502336A patent/PH12015502336B1/en unknown
- 2014-03-14 KR KR1020217038874A patent/KR102386952B1/ko active Active
- 2014-03-14 PH PH1/2020/550201A patent/PH12020550201A1/en unknown
- 2014-03-14 SG SG11201508532VA patent/SG11201508532VA/en unknown
- 2014-03-14 JP JP2016503187A patent/JP6364472B2/ja active Active
- 2014-03-14 RU RU2015143718A patent/RU2769607C2/ru not_active Application Discontinuation
- 2014-03-14 BR BR112015022263-3A patent/BR112015022263B1/pt active IP Right Grant
- 2014-03-14 CN CN201910586017.2A patent/CN110563700A/zh active Pending
- 2014-03-14 KR KR1020157029126A patent/KR102333718B1/ko active Active
- 2014-03-14 ES ES14764601T patent/ES2817902T3/es active Active
- 2014-03-14 EP EP14764601.2A patent/EP2968287B1/en active Active
- 2014-03-14 AU AU2014233414A patent/AU2014233414B2/en active Active
- 2014-03-14 CN CN201480026796.6A patent/CN105228620B/zh active Active
-
2015
- 2015-09-10 IL IL24152315A patent/IL241523B/en active IP Right Grant
- 2015-09-17 MX MX2019008003A patent/MX2019008003A/es unknown
-
2018
- 2018-07-02 JP JP2018126337A patent/JP2018184416A/ja active Pending
- 2018-09-24 AU AU2018236691A patent/AU2018236691B2/en active Active
-
2019
- 2019-09-19 IL IL269451A patent/IL269451B/en unknown
-
2020
- 2020-04-07 JP JP2020068792A patent/JP6985448B2/ja active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016516724A5 (enExample) | ||
| JP2020111602A5 (enExample) | ||
| RU2015143718A (ru) | N-ацил-N'-(пиридин-2-ил) карбамиды и их аналоги, проявляющие противораковую и антипролиферативную активность | |
| CN109071488B (zh) | 取代的1,2,3-三唑作为nr2b-选择性nmda调节剂 | |
| AU2024202088A1 (en) | 2-aminopyrimidin-6-ones and analogs exhibiting anti-cancer and anti-proliferative activities | |
| RU2018137194A (ru) | Ингибиторы бромдомена | |
| JP2015514794A5 (enExample) | ||
| JP2017522346A5 (enExample) | ||
| HRP20210949T1 (hr) | Spojevi i sastavi za moduliranje aktivnosti egfr mutant kinaze | |
| JP2016513660A5 (enExample) | ||
| IL274816B2 (en) | Sulfone pyridine alkyl amide-substituted heteroaryl compounds | |
| RU2012126989A (ru) | 2-амино-5,5-дифтор-5,6-дигидро-4н-оксазины в качестве ингибиторов васе 1 и(или) васе 2 | |
| JP2013505969A5 (enExample) | ||
| RU2017104510A (ru) | Соединения, активные по отношению к бромодоменам | |
| RU2015143191A (ru) | Дигидропирролопиридиновые ингибиторы бромодоменов | |
| CN110573501A (zh) | Rho相关蛋白激酶抑制剂、包含其的药物组合物及其制备方法和用途 | |
| JP2010512337A5 (enExample) | ||
| JP2013523803A5 (enExample) | ||
| IL276575B2 (en) | Inhibitors of btk and mutants thereof | |
| HRP20180272T1 (hr) | Benzamidi | |
| JP2016534134A5 (enExample) | ||
| JP2014505037A5 (enExample) | ||
| JP2016515606A5 (enExample) | ||
| JP2017512786A5 (enExample) | ||
| IL276998B2 (en) | Piperidinyl-3-(aryloxy)propanamides and propanoates |