JP2013510876A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013510876A5 JP2013510876A5 JP2012539028A JP2012539028A JP2013510876A5 JP 2013510876 A5 JP2013510876 A5 JP 2013510876A5 JP 2012539028 A JP2012539028 A JP 2012539028A JP 2012539028 A JP2012539028 A JP 2012539028A JP 2013510876 A5 JP2013510876 A5 JP 2013510876A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrrol
- pyrimidin
- fluoropyrimidin
- dimethylphenylamino
- 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
- 229920006395 saturated elastomer Polymers 0.000 claims 47
- 125000005842 heteroatom Chemical group 0.000 claims 38
- 229910052757 nitrogen Inorganic materials 0.000 claims 36
- 125000003118 aryl group Chemical group 0.000 claims 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000002619 bicyclic group Chemical group 0.000 claims 17
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 239000001301 oxygen Substances 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 239000011593 sulfur Substances 0.000 claims 14
- 150000003457 sulfones Chemical class 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 150000003462 sulfoxides Chemical class 0.000 claims 12
- -1 amino, hydroxy Chemical group 0.000 claims 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000003857 carboxamides Chemical class 0.000 claims 4
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- HIIHXLNMDAYCKQ-HSZRJFAPSA-N 2-[4-[[5-fluoro-4-[3-[[(3r)-3-hydroxypyrrolidin-1-yl]methyl]-4-methylpyrrol-1-yl]pyrimidin-2-yl]amino]-2,6-dimethylphenoxy]-1-morpholin-4-ylethanone Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(OCC(=O)N4CCOCC4)=C(C)C=3)N=2)F)C=C1CN1CC[C@@H](O)C1 HIIHXLNMDAYCKQ-HSZRJFAPSA-N 0.000 claims 2
- XAXIEMHZTRILQF-UHFFFAOYSA-N 2-[[1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-3-methylpyrazol-4-yl]methylamino]ethanol Chemical compound C1=C(CNCCO)C(C)=NN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F XAXIEMHZTRILQF-UHFFFAOYSA-N 0.000 claims 2
- DBWIEHCNYCUCAU-UHFFFAOYSA-N 4-[3-[(dimethylamino)methyl]-4-methylpyrrol-1-yl]-n-(3,5-dimethylphenyl)-5-methylpyrimidin-2-amine Chemical compound C1=C(C)C(CN(C)C)=CN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1C DBWIEHCNYCUCAU-UHFFFAOYSA-N 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- NVJQOZIENRVIML-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[3-methyl-4-(pyrrolidin-1-ylmethyl)pyrazol-1-yl]pyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CN1CCCC1 NVJQOZIENRVIML-UHFFFAOYSA-N 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- MKFMUFBNISHSOA-AWEZNQCLSA-N (2s)-2-[[1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-3-methylpyrazol-4-yl]methylamino]propan-1-ol Chemical compound N1=C(C)C(CN[C@H](CO)C)=CN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F MKFMUFBNISHSOA-AWEZNQCLSA-N 0.000 claims 1
- FJONTPGLWAYNIG-INIZCTEOSA-N (2s)-2-[[1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methylamino]propan-1-ol Chemical compound C1=C(C)C(CN[C@H](CO)C)=CN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F FJONTPGLWAYNIG-INIZCTEOSA-N 0.000 claims 1
- BDKKSQQENDGMGD-LJQANCHMSA-N (3r)-1-[[1-[2-(3,5-dimethylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)C(F)(F)F)C=C1CN1CC[C@@H](O)C1 BDKKSQQENDGMGD-LJQANCHMSA-N 0.000 claims 1
- CADFQOFOGSXHSQ-GOSISDBHSA-N (3r)-1-[[1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]pyrrol-3-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=CC(C)=CC(NC=2N=C(C(F)=CN=2)N2C=C(CN3C[C@H](O)CC3)C=C2)=C1 CADFQOFOGSXHSQ-GOSISDBHSA-N 0.000 claims 1
- APIGRKGHKBCGNE-HXUWFJFHSA-N (3r)-1-[[1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=CN(C=2N=C(NC=3C=C(C)C=C(C)C=3)N=CC=2)C=C1CN1CC[C@@H](O)C1 APIGRKGHKBCGNE-HXUWFJFHSA-N 0.000 claims 1
- PHZPJTBURBIEBX-MRXNPFEDSA-N (3r)-1-[[1-[2-[(4,6-dimethylpyrimidin-2-yl)amino]-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3N=C(C)C=C(C)N=3)N=2)F)C=C1CN1CC[C@@H](O)C1 PHZPJTBURBIEBX-MRXNPFEDSA-N 0.000 claims 1
- SWLZSBQVAQKAQR-QGZVFWFLSA-N (3r)-1-[[1-[2-[3,5-bis(trifluoromethyl)anilino]-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)N=2)F)C=C1CN1CC[C@@H](O)C1 SWLZSBQVAQKAQR-QGZVFWFLSA-N 0.000 claims 1
- JVPBZTOHNHBKKP-XMMPIXPASA-N (3r)-1-[[1-[2-[3,5-dimethyl-4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidin-4-yl]-3-methylpyrazol-4-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=NN(C=2N=C(NC=3C=C(C)C(OCCN4CCCC4)=C(C)C=3)N=CC=2)C=C1CN1CC[C@@H](O)C1 JVPBZTOHNHBKKP-XMMPIXPASA-N 0.000 claims 1
- ISOMVEODAPOIBJ-QGZVFWFLSA-N (3r)-1-[[1-[5-fluoro-2-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C=CC=3)C(F)(F)F)N=2)F)C=C1CN1CC[C@@H](O)C1 ISOMVEODAPOIBJ-QGZVFWFLSA-N 0.000 claims 1
- OSONANZITXBMIW-HXUWFJFHSA-N (3r)-1-[[1-[5-fluoro-2-[4-(2-hydroxyethoxy)-3,5-dimethylanilino]pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]pyrrolidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(OCCO)=C(C)C=3)N=2)F)C=C1CN1CC[C@@H](O)C1 OSONANZITXBMIW-HXUWFJFHSA-N 0.000 claims 1
- HYBHVIMICJZKEG-IBGZPJMESA-N (3s)-1-[4-[[4-[3-(hydroxymethyl)-4-methylpyrrol-1-yl]-5-methylpyrimidin-2-yl]amino]-2-methylphenyl]pyrrolidin-3-ol Chemical compound C1=C(CO)C(C)=CN1C1=NC(NC=2C=C(C)C(N3C[C@@H](O)CC3)=CC=2)=NC=C1C HYBHVIMICJZKEG-IBGZPJMESA-N 0.000 claims 1
- GJIZSZDBGLKUSJ-SFHVURJKSA-N (3s)-1-[[1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]pyrrolidine-3-carboxylic acid Chemical compound CC1=CN(C=2N=C(NC=3C=C(C)C=C(C)C=3)N=CC=2)C=C1CN1CC[C@H](C(O)=O)C1 GJIZSZDBGLKUSJ-SFHVURJKSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- WBYSTGDVDPOKJW-UHFFFAOYSA-N 1-[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]-n-(3,5-dimethylphenyl)pyrazole-4-carboxamide Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2N=CC(=C2)C(=O)NC=2C=C(C)C=C(C)C=2)=C1 WBYSTGDVDPOKJW-UHFFFAOYSA-N 0.000 claims 1
- OLRDGJPEIGJRCG-NSHDSACASA-N 1-[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]-n-[(2s)-1-hydroxypropan-2-yl]-3-methylpyrazole-4-carboxamide Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2N=C(C)C(C(=O)N[C@@H](C)CO)=C2)=C1 OLRDGJPEIGJRCG-NSHDSACASA-N 0.000 claims 1
- NQVOVOHDIKUYAG-UHFFFAOYSA-N 1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-3-methylpyrazole-4-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=NN1C1=CC=NC(NC=2C=C(C)C=C(C)C=2)=N1 NQVOVOHDIKUYAG-UHFFFAOYSA-N 0.000 claims 1
- IVBYFSNLTLRYDN-UHFFFAOYSA-N 1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-n,n-bis(2-hydroxyethyl)-3-methylpyrazole-4-carboxamide Chemical compound C1=C(C(=O)N(CCO)CCO)C(C)=NN1C1=CC=NC(NC=2C=C(C)C=C(C)C=2)=N1 IVBYFSNLTLRYDN-UHFFFAOYSA-N 0.000 claims 1
- FKAOPDLENPQYRV-UHFFFAOYSA-N 1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-n-(2-hydroxyethyl)-n,3-dimethylpyrazole-4-carboxamide Chemical compound N1=C(C)C(C(=O)N(CCO)C)=CN1C1=CC=NC(NC=2C=C(C)C=C(C)C=2)=N1 FKAOPDLENPQYRV-UHFFFAOYSA-N 0.000 claims 1
- ZATGKRCEPPRZRL-UHFFFAOYSA-N 1-[[1-[2-(2,3-dihydro-1h-inden-5-ylamino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]azetidin-3-ol Chemical compound CC1=CN(C=2N=C(NC=3C=C4CCCC4=CC=3)N=CC=2)C=C1CN1CC(O)C1 ZATGKRCEPPRZRL-UHFFFAOYSA-N 0.000 claims 1
- SQZWCZPTDDIDGB-UHFFFAOYSA-N 1-[[1-[2-(3,4-dimethylanilino)-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]azetidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(C)=CC=3)N=2)F)C=C1CN1CC(O)C1 SQZWCZPTDDIDGB-UHFFFAOYSA-N 0.000 claims 1
- CEWDMUSFPREMTN-UHFFFAOYSA-N 1-[[1-[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]piperidin-4-ol Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2C=C(CN3CCC(O)CC3)C(C)=C2)=C1 CEWDMUSFPREMTN-UHFFFAOYSA-N 0.000 claims 1
- PEHATVLTXRELKI-UHFFFAOYSA-N 1-[[1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-3-methylpyrazol-4-yl]methyl]piperidin-4-ol Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CN1CCC(O)CC1 PEHATVLTXRELKI-UHFFFAOYSA-N 0.000 claims 1
- GBKFVAZZSJYFHT-UHFFFAOYSA-N 1-[[1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]piperidin-4-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CN1CCC(O)CC1 GBKFVAZZSJYFHT-UHFFFAOYSA-N 0.000 claims 1
- QDSBDIJLEMPKIN-UHFFFAOYSA-N 1-[[1-[2-(3,5-dimethylanilino)-5-methylpyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]piperidin-4-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)C)C=C1CN1CCC(O)CC1 QDSBDIJLEMPKIN-UHFFFAOYSA-N 0.000 claims 1
- RTQYLJBPAHAXPW-UHFFFAOYSA-N 1-[[1-[2-[3,5-bis(trifluoromethyl)anilino]-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]piperidin-4-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)N=2)F)C=C1CN1CCC(O)CC1 RTQYLJBPAHAXPW-UHFFFAOYSA-N 0.000 claims 1
- KBOXMEIXTPIOIE-UHFFFAOYSA-N 1-[[1-[5-chloro-2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]azetidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C4OCCOC4=CC=3)N=2)Cl)C=C1CN1CC(O)C1 KBOXMEIXTPIOIE-UHFFFAOYSA-N 0.000 claims 1
- IHPNQSHTXWPFQG-UHFFFAOYSA-N 1-[[1-[5-chloro-2-[4-(2-hydroxyethoxy)-3,5-dimethylanilino]pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]azetidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(OCCO)=C(C)C=3)N=2)Cl)C=C1CN1CC(O)C1 IHPNQSHTXWPFQG-UHFFFAOYSA-N 0.000 claims 1
- CYLUHHQGTYMADN-UHFFFAOYSA-N 1-[[1-[5-fluoro-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]-4-(furan-3-yl)pyrrol-3-yl]methyl]azetidin-3-ol Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(F)=CN=2)N2C=C(C(CN3CC(O)C3)=C2)C2=COC=C2)=C1 CYLUHHQGTYMADN-UHFFFAOYSA-N 0.000 claims 1
- NLHRNSWKEOUBND-UHFFFAOYSA-N 1-[[1-[5-fluoro-2-(naphthalen-2-ylamino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]azetidin-3-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C4C=CC=CC4=CC=3)N=2)F)C=C1CN1CC(O)C1 NLHRNSWKEOUBND-UHFFFAOYSA-N 0.000 claims 1
- SSNCUUYJMQQMHT-UHFFFAOYSA-N 1-[[1-[5-fluoro-2-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]piperidin-4-ol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C=CC=3)C(F)(F)F)N=2)F)C=C1CN1CCC(O)CC1 SSNCUUYJMQQMHT-UHFFFAOYSA-N 0.000 claims 1
- KZBAZWAWQWUVBG-UHFFFAOYSA-N 1-[[4-cyclopropyl-1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]pyrrol-3-yl]methyl]azetidin-3-ol Chemical compound CC1=CC(C)=CC(NC=2N=C(C=CN=2)N2C=C(C(CN3CC(O)C3)=C2)C2CC2)=C1 KZBAZWAWQWUVBG-UHFFFAOYSA-N 0.000 claims 1
- SQHWWNVCKUOHOU-UHFFFAOYSA-N 1-[[4-methyl-1-[2-(3-methyl-4-phenylanilino)pyrimidin-4-yl]pyrrol-3-yl]methyl]azetidin-3-ol Chemical compound CC1=CN(C=2N=C(NC=3C=C(C)C(=CC=3)C=3C=CC=CC=3)N=CC=2)C=C1CN1CC(O)C1 SQHWWNVCKUOHOU-UHFFFAOYSA-N 0.000 claims 1
- UBVUHNLTWFRDMU-UHFFFAOYSA-N 1-[[4-methyl-1-[2-[(1-methylindol-5-yl)amino]pyrimidin-4-yl]pyrrol-3-yl]methyl]azetidin-3-ol Chemical compound CC1=CN(C=2N=C(NC=3C=C4C=CN(C)C4=CC=3)N=CC=2)C=C1CN1CC(O)C1 UBVUHNLTWFRDMU-UHFFFAOYSA-N 0.000 claims 1
- ZZENAAYBRXROCX-UHFFFAOYSA-N 2,2-dimethyl-1-[4-[[4-methyl-1-[5-methyl-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]pyrrol-3-yl]methyl]-1,4-diazepan-1-yl]propan-1-one Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(CN3CCN(CCC3)C(=O)C(C)(C)C)C(C)=C2)=C1 ZZENAAYBRXROCX-UHFFFAOYSA-N 0.000 claims 1
- QAZLVTUPZYIOQR-UHFFFAOYSA-N 2-[4-[4-[[4-[3-(hydroxymethyl)-4-methylpyrrol-1-yl]-5-methylpyrimidin-2-yl]amino]-2-methylphenyl]piperazin-1-yl]ethanol Chemical compound C1=C(CO)C(C)=CN1C1=NC(NC=2C=C(C)C(N3CCN(CCO)CC3)=CC=2)=NC=C1C QAZLVTUPZYIOQR-UHFFFAOYSA-N 0.000 claims 1
- VEUPGYNVVUMJPB-UHFFFAOYSA-N 2-[4-[[1-[2-[4-[4-(2-hydroxyethyl)piperazin-1-yl]-3-methylanilino]-5-methylpyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]piperazin-1-yl]ethanol Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(N4CCN(CCO)CC4)=CC=3)N=2)C)C=C1CN1CCN(CCO)CC1 VEUPGYNVVUMJPB-UHFFFAOYSA-N 0.000 claims 1
- CSFPCQGTIYXGCB-UHFFFAOYSA-N 2-[4-[[1-[5-chloro-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]piperazin-1-yl]ethanol Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(Cl)=CN=2)N2C=C(CN3CCN(CCO)CC3)C(C)=C2)=C1 CSFPCQGTIYXGCB-UHFFFAOYSA-N 0.000 claims 1
- INCIASVNZBIWSR-UHFFFAOYSA-N 2-[4-[[4-[3-(2,5-diazabicyclo[2.2.1]heptan-2-ylmethyl)-4-methylpyrrol-1-yl]-5-methylpyrimidin-2-yl]amino]-2,6-dimethylphenoxy]ethanol;trihydrochloride Chemical compound Cl.Cl.Cl.C1=C(CN2C3CC(NC3)C2)C(C)=CN1C(C(=CN=1)C)=NC=1NC1=CC(C)=C(OCCO)C(C)=C1 INCIASVNZBIWSR-UHFFFAOYSA-N 0.000 claims 1
- DFHFNGJJBVRENX-UHFFFAOYSA-N 2-[4-[[4-[3-(hydroxymethyl)-4-methylpyrrol-1-yl]-5-methylpyrimidin-2-yl]amino]-2,6-dimethoxyphenoxy]ethanol Chemical compound COC1=C(OCCO)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(CO)C(C)=C2)=C1 DFHFNGJJBVRENX-UHFFFAOYSA-N 0.000 claims 1
- SJEOYDLPQUJSER-UHFFFAOYSA-N 2-[4-[[4-[3-[(dimethylamino)methyl]-4-methylpyrrol-1-yl]-5-methylpyrimidin-2-yl]amino]-2,6-dimethylphenoxy]ethanol Chemical compound C1=C(C)C(CN(C)C)=CN1C1=NC(NC=2C=C(C)C(OCCO)=C(C)C=2)=NC=C1C SJEOYDLPQUJSER-UHFFFAOYSA-N 0.000 claims 1
- ZGZGSJNUWKNUCV-UHFFFAOYSA-N 2-[4-[[4-[4-[(3-hydroxyazetidin-1-yl)methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-2,6-dimethylphenoxy]-1-morpholin-4-ylethanone Chemical compound CC1=NN(C=2N=C(NC=3C=C(C)C(OCC(=O)N4CCOCC4)=C(C)C=3)N=CC=2)C=C1CN1CC(O)C1 ZGZGSJNUWKNUCV-UHFFFAOYSA-N 0.000 claims 1
- GJGIVGDUHWXPED-HSZRJFAPSA-N 2-[4-[[4-[4-[[(3r)-3-hydroxypyrrolidin-1-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-2,6-dimethylphenoxy]-1-morpholin-4-ylethanone Chemical compound CC1=NN(C=2N=C(NC=3C=C(C)C(OCC(=O)N4CCOCC4)=C(C)C=3)N=CC=2)C=C1CN1CC[C@@H](O)C1 GJGIVGDUHWXPED-HSZRJFAPSA-N 0.000 claims 1
- ZZILMEKMXGZKEX-UHFFFAOYSA-N 2-[4-[[4-methyl-1-[5-methyl-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]pyrrol-3-yl]methyl]piperazin-1-yl]ethanol Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(CN3CCN(CCO)CC3)C(C)=C2)=C1 ZZILMEKMXGZKEX-UHFFFAOYSA-N 0.000 claims 1
- SDPNUXRSQIXWRV-UHFFFAOYSA-N 2-[4-[[5-fluoro-4-[3-(hydroxymethyl)-4-methylpyrrol-1-yl]pyrimidin-2-yl]amino]-2,6-dimethylphenoxy]ethanol Chemical compound C1=C(CO)C(C)=CN1C1=NC(NC=2C=C(C)C(OCCO)=C(C)C=2)=NC=C1F SDPNUXRSQIXWRV-UHFFFAOYSA-N 0.000 claims 1
- QVFHPRLROKAQAU-UHFFFAOYSA-N 2-[4-[[5-fluoro-4-[3-[(3-hydroxyazetidin-1-yl)methyl]-4-methylpyrrol-1-yl]pyrimidin-2-yl]amino]-2,6-dimethylphenoxy]-1-pyrrolidin-1-ylethanone Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(OCC(=O)N4CCCC4)=C(C)C=3)N=2)F)C=C1CN1CC(O)C1 QVFHPRLROKAQAU-UHFFFAOYSA-N 0.000 claims 1
- CQLCZFQSVHTFCG-UHFFFAOYSA-N 3-[4-[[4-methyl-1-[5-methyl-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]pyrrol-3-yl]methyl]piperazin-1-yl]-3-oxopropanenitrile Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(CN3CCN(CC3)C(=O)CC#N)C(C)=C2)=C1 CQLCZFQSVHTFCG-UHFFFAOYSA-N 0.000 claims 1
- USQDYGMBJJENCS-UHFFFAOYSA-N 4-[3-(1,4-diazepan-1-ylmethyl)-4-methylpyrrol-1-yl]-5-methyl-n-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine;trihydrochloride Chemical compound Cl.Cl.Cl.COC1=C(OC)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(CN3CCNCCC3)C(C)=C2)=C1 USQDYGMBJJENCS-UHFFFAOYSA-N 0.000 claims 1
- RCPHNUYCPFHUHR-UHFFFAOYSA-N 4-[3-[(4,4-difluoropiperidin-1-yl)methyl]-4-methylpyrrol-1-yl]-n-(3,5-dimethylphenyl)pyrimidin-2-amine Chemical compound CC1=CN(C=2N=C(NC=3C=C(C)C=C(C)C=3)N=CC=2)C=C1CN1CCC(F)(F)CC1 RCPHNUYCPFHUHR-UHFFFAOYSA-N 0.000 claims 1
- AKEHZVFAVRKUMX-UHFFFAOYSA-N 4-[3-[(benzylamino)methyl]-4-methylpyrrol-1-yl]-n-(3,5-dimethoxyphenyl)-5-fluoropyrimidin-2-amine Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2C=C(CNCC=3C=CC=CC=3)C(C)=C2)=C1 AKEHZVFAVRKUMX-UHFFFAOYSA-N 0.000 claims 1
- FLYSGYJTLKECFX-UHFFFAOYSA-N 4-[3-[(dimethylamino)methyl]-4-(furan-3-yl)pyrrol-1-yl]-5-fluoro-n-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(F)=CN=2)N2C=C(C(CN(C)C)=C2)C2=COC=C2)=C1 FLYSGYJTLKECFX-UHFFFAOYSA-N 0.000 claims 1
- JOSIRONTTLQHMP-UHFFFAOYSA-N 4-[3-[(dimethylamino)methyl]-4-methylpyrrol-1-yl]-5-fluoro-n-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound C1=C(C)C(CN(C)C)=CN1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=NC=C1F JOSIRONTTLQHMP-UHFFFAOYSA-N 0.000 claims 1
- IXMORULGPBSZDJ-UHFFFAOYSA-N 4-[3-[(dimethylamino)methyl]-4-methylpyrrol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound C1=C(C)C(CN(C)C)=CN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F IXMORULGPBSZDJ-UHFFFAOYSA-N 0.000 claims 1
- XSZBXSSLZJLZIR-UHFFFAOYSA-N 4-[3-[(dimethylamino)methyl]-4-phenylpyrrol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound CN(C)CC1=CN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1C1=CC=CC=C1 XSZBXSSLZJLZIR-UHFFFAOYSA-N 0.000 claims 1
- WUGBZZXTIKERPP-UHFFFAOYSA-N 4-[3-[(dimethylamino)methyl]pyrrol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound C1=C(CN(C)C)C=CN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F WUGBZZXTIKERPP-UHFFFAOYSA-N 0.000 claims 1
- LMTHMRFKJRDWPQ-GOSISDBHSA-N 4-[3-[[(3r)-3-aminopyrrolidin-1-yl]methyl]-4-methylpyrrol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CN1CC[C@@H](N)C1 LMTHMRFKJRDWPQ-GOSISDBHSA-N 0.000 claims 1
- IQTZXQVUPVUZOE-UHFFFAOYSA-N 4-[4-(3,4-dihydro-1h-isoquinolin-2-ylmethyl)-3-methylpyrazol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound C1=C(CN2CC3=CC=CC=C3CC2)C(C)=NN1C(C(=CN=1)F)=NC=1NC1=CC(C)=CC(C)=C1 IQTZXQVUPVUZOE-UHFFFAOYSA-N 0.000 claims 1
- NMHHMIMJUXQMAW-UHFFFAOYSA-N 4-[4-(anilinomethyl)-3-methylpyrazol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CNC1=CC=CC=C1 NMHHMIMJUXQMAW-UHFFFAOYSA-N 0.000 claims 1
- RVZVSRKUTRJMSV-UHFFFAOYSA-N 4-[4-[(benzylamino)methyl]-3-methylpyrazol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CNCC1=CC=CC=C1 RVZVSRKUTRJMSV-UHFFFAOYSA-N 0.000 claims 1
- ZWOUBSYJRHCSJZ-UHFFFAOYSA-N 4-[4-[(benzylamino)methyl]-3-methylpyrazol-1-yl]-n-(3,5-dimethylphenyl)pyrimidin-2-amine Chemical compound CC1=NN(C=2N=C(NC=3C=C(C)C=C(C)C=3)N=CC=2)C=C1CNCC1=CC=CC=C1 ZWOUBSYJRHCSJZ-UHFFFAOYSA-N 0.000 claims 1
- LVCBSDNAOLXBRA-UHFFFAOYSA-N 4-[4-[(cyclohexylamino)methyl]-3-methylpyrazol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CNC1CCCCC1 LVCBSDNAOLXBRA-UHFFFAOYSA-N 0.000 claims 1
- KKNWPMSVADHHTH-UHFFFAOYSA-N 4-[4-[(cyclopropylamino)methyl]-3-methylpyrazol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CNC1CC1 KKNWPMSVADHHTH-UHFFFAOYSA-N 0.000 claims 1
- ORAGPVSEVBIZDE-UHFFFAOYSA-N 4-[4-[(dimethylamino)methyl]-3-methylpyrazol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound N1=C(C)C(CN(C)C)=CN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F ORAGPVSEVBIZDE-UHFFFAOYSA-N 0.000 claims 1
- PEWZSBXUKVGMEI-UHFFFAOYSA-N 4-[4-[[benzyl(methyl)amino]methyl]-3-methylpyrazol-1-yl]-n-(3,5-dimethylphenyl)-5-fluoropyrimidin-2-amine Chemical compound C=1C=CC=CC=1CN(C)CC(C(=N1)C)=CN1C(C(=CN=1)F)=NC=1NC1=CC(C)=CC(C)=C1 PEWZSBXUKVGMEI-UHFFFAOYSA-N 0.000 claims 1
- LWVPUUQUVPSFDB-UHFFFAOYSA-N 4-[[1-[2-[4-(2-hydroxyethoxy)-3,5-dimethylanilino]-5-methylpyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]-1,4-diazepane-1-carboxamide Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(OCCO)=C(C)C=3)N=2)C)C=C1CN1CCCN(C(N)=O)CC1 LWVPUUQUVPSFDB-UHFFFAOYSA-N 0.000 claims 1
- FAQLOOPIJIVZDY-UHFFFAOYSA-N 4-[[1-[2-[4-(2-hydroxyethoxy)-3,5-dimethylanilino]-5-methylpyrimidin-4-yl]-4-methylpyrrol-3-yl]methyl]-n-methyl-1,4-diazepane-1-carboxamide Chemical compound C1CN(C(=O)NC)CCCN1CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(OCCO)=C(C)C=3)N=2)C)C=C1C FAQLOOPIJIVZDY-UHFFFAOYSA-N 0.000 claims 1
- QXWSWPYVDQSMFY-UHFFFAOYSA-N 5-bromo-4-[3-(2,5-diazabicyclo[2.2.1]heptan-2-ylmethyl)-4-methylpyrrol-1-yl]-n-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine;trihydrochloride Chemical compound Cl.Cl.Cl.COC1=C(OC)C(OC)=CC(NC=2N=C(C(Br)=CN=2)N2C=C(CN3C4CC(NC4)C3)C(C)=C2)=C1 QXWSWPYVDQSMFY-UHFFFAOYSA-N 0.000 claims 1
- PFZAIGJCFXXVJQ-UHFFFAOYSA-N 5-chloro-4-[3-(1,4-diazepan-1-ylmethyl)-4-methylpyrrol-1-yl]-n-(2,3-dihydro-1,4-benzodioxin-6-yl)pyrimidin-2-amine Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C4OCCOC4=CC=3)N=2)Cl)C=C1CN1CCCNCC1 PFZAIGJCFXXVJQ-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010002329 Aneurysm Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 200000000007 Arterial disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- UFRBMWGYXRSAHS-UHFFFAOYSA-N CC=1C=C(C=C(C1OCCN1CCCC1)C)NC1=NC=C(C(=N1)N1C=CC(=C1)C)C Chemical compound CC=1C=C(C=C(C1OCCN1CCCC1)C)NC1=NC=C(C(=N1)N1C=CC(=C1)C)C UFRBMWGYXRSAHS-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 102000008186 Collagen Human genes 0.000 claims 1
- 108010035532 Collagen Proteins 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims 1
- 208000004196 Heart Aneurysm Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000011200 Kawasaki disease Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000029725 Metabolic bone disease Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 208000010191 Osteitis Deformans Diseases 0.000 claims 1
- 206010049088 Osteopenia 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
- 208000027868 Paget disease Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 241001303601 Rosacea Species 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000032450 Surgical Shock Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 206010044541 Traumatic shock Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 206010047139 Vasoconstriction Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- FDMMRQLYPWUWLO-UHFFFAOYSA-N [1-[2-(2,3-dihydro-1h-inden-5-ylamino)pyrimidin-4-yl]pyrrol-3-yl]methanol Chemical compound C1=C(CO)C=CN1C1=CC=NC(NC=2C=C3CCCC3=CC=2)=N1 FDMMRQLYPWUWLO-UHFFFAOYSA-N 0.000 claims 1
- OFBMORSMHMQDEK-UHFFFAOYSA-N [1-[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]-3-methylpyrazol-4-yl]methanol Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2N=C(C)C(CO)=C2)=C1 OFBMORSMHMQDEK-UHFFFAOYSA-N 0.000 claims 1
- YIZPCRJFBQPRAZ-UHFFFAOYSA-N [1-[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2C=C(CO)C(C)=C2)=C1 YIZPCRJFBQPRAZ-UHFFFAOYSA-N 0.000 claims 1
- PAKRTYHXDQVJRA-UHFFFAOYSA-N [1-[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]pyrazol-4-yl]-piperidin-1-ylmethanone Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2N=CC(=C2)C(=O)N2CCCCC2)=C1 PAKRTYHXDQVJRA-UHFFFAOYSA-N 0.000 claims 1
- DUNWFQSFQOCCLL-UHFFFAOYSA-N [1-[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]pyrazol-4-yl]methanol Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2N=CC(CO)=C2)=C1 DUNWFQSFQOCCLL-UHFFFAOYSA-N 0.000 claims 1
- JJAQKABFPOWJHJ-UHFFFAOYSA-N [1-[2-(3,5-dimethyl-4-phenoxyanilino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound C1=C(CO)C(C)=CN1C1=CC=NC(NC=2C=C(C)C(OC=3C=CC=CC=3)=C(C)C=2)=N1 JJAQKABFPOWJHJ-UHFFFAOYSA-N 0.000 claims 1
- NADOBMYCKJYASY-UHFFFAOYSA-N [1-[2-(3,5-dimethylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound C1=C(CO)C(C)=CN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1C(F)(F)F NADOBMYCKJYASY-UHFFFAOYSA-N 0.000 claims 1
- ZHVWWWSMWGZZKX-UHFFFAOYSA-N [1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-3-methylpyrazol-4-yl]methanol Chemical compound C1=C(CO)C(C)=NN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F ZHVWWWSMWGZZKX-UHFFFAOYSA-N 0.000 claims 1
- KEXKKJAUJRSRPQ-UHFFFAOYSA-N [1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound C1=C(CO)C(C)=CN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F KEXKKJAUJRSRPQ-UHFFFAOYSA-N 0.000 claims 1
- NQXCGNXAORVBME-UHFFFAOYSA-N [1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-4-phenylpyrrol-3-yl]methanol Chemical compound CC1=CC(C)=CC(NC=2N=C(C(F)=CN=2)N2C=C(C(CO)=C2)C=2C=CC=CC=2)=C1 NQXCGNXAORVBME-UHFFFAOYSA-N 0.000 claims 1
- MZQOUWRZDQREOV-UHFFFAOYSA-N [1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]pyrazol-4-yl]methanol Chemical compound CC1=CC(C)=CC(NC=2N=C(C(F)=CN=2)N2N=CC(CO)=C2)=C1 MZQOUWRZDQREOV-UHFFFAOYSA-N 0.000 claims 1
- FVOFKQIUYZXUGS-UHFFFAOYSA-N [1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]pyrrol-3-yl]methanol Chemical compound CC1=CC(C)=CC(NC=2N=C(C(F)=CN=2)N2C=C(CO)C=C2)=C1 FVOFKQIUYZXUGS-UHFFFAOYSA-N 0.000 claims 1
- SEMPIICIPSVDGH-QGZVFWFLSA-N [1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-3-methylpyrazol-4-yl]-[(3r)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound CC1=NN(C=2N=C(NC=3C=C(C)C=C(C)C=3)N=CC=2)C=C1C(=O)N1CC[C@@H](O)C1 SEMPIICIPSVDGH-QGZVFWFLSA-N 0.000 claims 1
- SEMPIICIPSVDGH-KRWDZBQOSA-N [1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-3-methylpyrazol-4-yl]-[(3s)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound CC1=NN(C=2N=C(NC=3C=C(C)C=C(C)C=3)N=CC=2)C=C1C(=O)N1CC[C@H](O)C1 SEMPIICIPSVDGH-KRWDZBQOSA-N 0.000 claims 1
- NLXQPNURLWHHQH-UHFFFAOYSA-N [1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-3-methylpyrazol-4-yl]methanol Chemical compound C1=C(CO)C(C)=NN1C1=CC=NC(NC=2C=C(C)C=C(C)C=2)=N1 NLXQPNURLWHHQH-UHFFFAOYSA-N 0.000 claims 1
- ONGGGUGVMJUZEW-UHFFFAOYSA-N [1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]pyrrol-3-yl]methanol Chemical compound CC1=CC(C)=CC(NC=2N=C(C=CN=2)N2C=C(CO)C=C2)=C1 ONGGGUGVMJUZEW-UHFFFAOYSA-N 0.000 claims 1
- PSLJBLOXPMIIKC-UHFFFAOYSA-N [1-[2-[3,5-bis(trifluoromethyl)anilino]-5-fluoropyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound C1=C(CO)C(C)=CN1C1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=NC=C1F PSLJBLOXPMIIKC-UHFFFAOYSA-N 0.000 claims 1
- SRNXEDDTIMPMGE-UHFFFAOYSA-N [1-[2-[3,5-dimethyl-4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound C1=C(CO)C(C)=CN1C1=CC=NC(NC=2C=C(C)C(OCCN3CCCC3)=C(C)C=2)=N1 SRNXEDDTIMPMGE-UHFFFAOYSA-N 0.000 claims 1
- AIMFUILTSKAMAT-UHFFFAOYSA-N [1-[5-chloro-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(Cl)=CN=2)N2C=C(CO)C(C)=C2)=C1 AIMFUILTSKAMAT-UHFFFAOYSA-N 0.000 claims 1
- YSJGLGYAFPZGQE-UHFFFAOYSA-N [1-[5-fluoro-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]-4-(furan-3-yl)pyrrol-3-yl]methanol Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(F)=CN=2)N2C=C(C(CO)=C2)C2=COC=C2)=C1 YSJGLGYAFPZGQE-UHFFFAOYSA-N 0.000 claims 1
- VFQCDXAGUUEUMA-UHFFFAOYSA-N [1-[5-fluoro-2-(4-methylsulfonylanilino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound C1=C(CO)C(C)=CN1C1=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=NC=C1F VFQCDXAGUUEUMA-UHFFFAOYSA-N 0.000 claims 1
- QMWRVAOSPSCBSO-UHFFFAOYSA-N [1-[5-fluoro-2-(naphthalen-2-ylamino)pyrimidin-4-yl]-4-methylpyrrol-3-yl]methanol Chemical compound C1=C(CO)C(C)=CN1C1=NC(NC=2C=C3C=CC=CC3=CC=2)=NC=C1F QMWRVAOSPSCBSO-UHFFFAOYSA-N 0.000 claims 1
- SSBDNSYZIRKWKU-UHFFFAOYSA-N [1-[[4-methyl-1-[5-methyl-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]pyrrol-3-yl]methyl]piperidin-4-yl]methanol Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(CN3CCC(CO)CC3)C(C)=C2)=C1 SSBDNSYZIRKWKU-UHFFFAOYSA-N 0.000 claims 1
- MGSGLWKIRPGDFO-LJQANCHMSA-N [4-[[5-fluoro-4-[3-[[(3R)-3-hydroxypyrrolidin-1-yl]methyl]-4-methylpyrrol-1-yl]pyrimidin-2-yl]amino]-2,6-dimethylphenyl]methanesulfonic acid Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C(CS(O)(=O)=O)=C(C)C=3)N=2)F)C=C1CN1CC[C@@H](O)C1 MGSGLWKIRPGDFO-LJQANCHMSA-N 0.000 claims 1
- XDYVNLFSFSSVQB-UHFFFAOYSA-N [4-cyclopropyl-1-[5-methyl-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]pyrrol-3-yl]methanol Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(C(CO)=C2)C2CC2)=C1 XDYVNLFSFSSVQB-UHFFFAOYSA-N 0.000 claims 1
- SNZHQCIBLWFKIT-UHFFFAOYSA-N [4-methyl-1-[5-methyl-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]pyrrol-3-yl]methanol Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(CO)C(C)=C2)=C1 SNZHQCIBLWFKIT-UHFFFAOYSA-N 0.000 claims 1
- IESAYDJBNANVHB-UHFFFAOYSA-N [4-methyl-1-[5-methyl-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]pyrrol-3-yl]methylurea Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(C)=CN=2)N2C=C(CNC(N)=O)C(C)=C2)=C1 IESAYDJBNANVHB-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229920001436 collagen Polymers 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002158 endotoxin Substances 0.000 claims 1
- KHPPMZICHKGGAL-UHFFFAOYSA-N ethyl 1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-3-methylpyrazole-4-carboxylate Chemical compound N1=C(C)C(C(=O)OCC)=CN1C1=CC=NC(NC=2C=C(C)C=C(C)C=2)=N1 KHPPMZICHKGGAL-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 208000018578 heart valve disease Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 201000010982 kidney cancer 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
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 208000027202 mammary Paget disease Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- WVLHTLKMSJXKKK-UHFFFAOYSA-N methyl 1-[5-methyl-2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]pyrrole-3-carboxylate Chemical compound C1=C(C(=O)OC)C=CN1C1=NC(NC=2C=C(OC)C(OC)=C(OC)C=2)=NC=C1C WVLHTLKMSJXKKK-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- XJRRQPWFEPPNFW-UHFFFAOYSA-N n'-[[1-[2-(3,5-dimethylanilino)-5-fluoropyrimidin-4-yl]-3-methylpyrazol-4-yl]methyl]ethane-1,2-diamine Chemical compound C1=C(CNCCN)C(C)=NN1C1=NC(NC=2C=C(C)C=C(C)C=2)=NC=C1F XJRRQPWFEPPNFW-UHFFFAOYSA-N 0.000 claims 1
- KLODLWYYSGBBHA-UHFFFAOYSA-N n-(2-aminoethyl)-1-[2-(3,5-dimethylanilino)pyrimidin-4-yl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(C)=CC(NC=2N=C(C=CN=2)N2N=C(C(C(=O)NCCN)=C2)C(F)(F)F)=C1 KLODLWYYSGBBHA-UHFFFAOYSA-N 0.000 claims 1
- AVHQSZSYVKUKIO-UHFFFAOYSA-N n-(3,5-dimethoxyphenyl)-4-[3-[(dimethylamino)methyl]-4-methylpyrrol-1-yl]-5-fluoropyrimidin-2-amine Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2C=C(CN(C)C)C(C)=C2)=C1 AVHQSZSYVKUKIO-UHFFFAOYSA-N 0.000 claims 1
- NSQSXLLYMRVGEE-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[3-[(3-sulfonylpyrrolidin-1-yl)methyl]pyrrol-1-yl]pyrimidin-2-amine Chemical compound CC1=CC(C)=CC(NC=2N=C(C(F)=CN=2)N2C=C(CN3CC(CC3)=S(=O)=O)C=C2)=C1 NSQSXLLYMRVGEE-UHFFFAOYSA-N 0.000 claims 1
- RFGVWPVYUBMKTR-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[3-methyl-4-(morpholin-4-ylmethyl)pyrrol-1-yl]pyrimidin-2-amine Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CN1CCOCC1 RFGVWPVYUBMKTR-UHFFFAOYSA-N 0.000 claims 1
- NHKPVYLHEYEVFU-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[3-methyl-4-(piperidin-1-ylmethyl)pyrazol-1-yl]pyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CN1CCCCC1 NHKPVYLHEYEVFU-UHFFFAOYSA-N 0.000 claims 1
- ADSVKOIDIMKMPL-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[3-methyl-4-(piperidin-1-ylmethyl)pyrrol-1-yl]pyrimidin-2-amine Chemical compound CC1=CN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CN1CCCCC1 ADSVKOIDIMKMPL-UHFFFAOYSA-N 0.000 claims 1
- IPGVJPQTGKKICQ-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[3-methyl-4-[(4-methylpiperazin-1-yl)methyl]pyrazol-1-yl]pyrimidin-2-amine Chemical class C1CN(C)CCN1CC1=CN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)N=C1C IPGVJPQTGKKICQ-UHFFFAOYSA-N 0.000 claims 1
- WSDMPEZXHUBLOP-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[3-methyl-4-[(piperidin-4-ylamino)methyl]pyrazol-1-yl]pyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CNC1CCNCC1 WSDMPEZXHUBLOP-UHFFFAOYSA-N 0.000 claims 1
- DBFLUZPALSPMFB-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[3-methyl-4-[(pyridin-4-ylmethylamino)methyl]pyrazol-1-yl]pyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CNCC1=CC=NC=C1 DBFLUZPALSPMFB-UHFFFAOYSA-N 0.000 claims 1
- IMQGPPKTXMFNCK-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-5-fluoro-4-[4-[[2-(4-fluorophenyl)ethylamino]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-amine Chemical compound CC1=NN(C=2C(=CN=C(NC=3C=C(C)C=C(C)C=3)N=2)F)C=C1CNCCC1=CC=C(F)C=C1 IMQGPPKTXMFNCK-UHFFFAOYSA-N 0.000 claims 1
- OGXUQXBQRHTADR-UHFFFAOYSA-N n-[3,5-bis(trifluoromethyl)phenyl]-4-[3-[(dimethylamino)methyl]-4-methylpyrrol-1-yl]-5-fluoropyrimidin-2-amine Chemical compound C1=C(C)C(CN(C)C)=CN1C1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=NC=C1F OGXUQXBQRHTADR-UHFFFAOYSA-N 0.000 claims 1
- QSNWAWYNISGDDQ-UHFFFAOYSA-N n-benzyl-1-[2-(3,5-dimethoxyanilino)-5-fluoropyrimidin-4-yl]pyrazole-4-carboxamide Chemical compound COC1=CC(OC)=CC(NC=2N=C(C(F)=CN=2)N2N=CC(=C2)C(=O)NCC=2C=CC=CC=2)=C1 QSNWAWYNISGDDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 208000005368 osteomalacia Diseases 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 206010040560 shock Diseases 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 230000006496 vascular abnormality Effects 0.000 claims 1
- 230000025033 vasoconstriction Effects 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26110009P | 2009-11-13 | 2009-11-13 | |
| US61/261,100 | 2009-11-13 | ||
| PCT/US2010/056583 WO2011060295A1 (en) | 2009-11-13 | 2010-11-12 | Kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013510876A JP2013510876A (ja) | 2013-03-28 |
| JP2013510876A5 true JP2013510876A5 (enExample) | 2014-01-09 |
| JP5740409B2 JP5740409B2 (ja) | 2015-06-24 |
Family
ID=43992073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012539028A Active JP5740409B2 (ja) | 2009-11-13 | 2010-11-12 | キナーゼ阻害剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8629132B2 (enExample) |
| EP (1) | EP2498607B1 (enExample) |
| JP (1) | JP5740409B2 (enExample) |
| KR (1) | KR101663637B1 (enExample) |
| CN (1) | CN102811619B (enExample) |
| BR (1) | BR112012011287B1 (enExample) |
| CA (1) | CA2780892C (enExample) |
| CL (1) | CL2012001221A1 (enExample) |
| EA (1) | EA024729B1 (enExample) |
| IL (1) | IL219726A (enExample) |
| MX (1) | MX2012005332A (enExample) |
| MY (1) | MY160820A (enExample) |
| NZ (1) | NZ599041A (enExample) |
| SG (1) | SG10201407453TA (enExample) |
| WO (1) | WO2011060295A1 (enExample) |
| ZA (1) | ZA201204246B (enExample) |
Families Citing this family (107)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2918588T3 (pl) | 2010-05-20 | 2017-10-31 | Array Biopharma Inc | Związki makrocykliczne jako inhibitory kinazy TRK |
| PT2576541T (pt) | 2010-06-04 | 2016-07-08 | Hoffmann La Roche | Derivados de aminopirimidina como moduladores de lrrk2 |
| CA2812669C (en) | 2010-11-10 | 2018-11-06 | F. Hoffmann-La Roche Ag | Pyrazole aminopyrimidine derivatives as lrrk2 modulators |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| WO2013054351A1 (en) * | 2011-08-08 | 2013-04-18 | Cadila Healthcare Limited | Heterocyclic compounds |
| MX2014002208A (es) | 2011-08-25 | 2014-05-28 | Hoffmann La Roche | Inhibidores de serina/treonina quinasa. |
| EP2794605A1 (en) | 2011-12-22 | 2014-10-29 | F.Hoffmann-La Roche Ag | 2, 4-diamine-pyrimidine derivative as serine/threonine kinase inhibitors |
| CA2863517C (en) * | 2012-01-20 | 2019-11-05 | Genosco | Substituted pyrimidine compounds and their use as syk inhibitors |
| US9096579B2 (en) * | 2012-04-20 | 2015-08-04 | Boehringer Ingelheim International Gmbh | Amino-indolyl-substituted imidazolyl-pyrimidines and their use as medicaments |
| BR112014027181A2 (pt) | 2012-05-15 | 2017-06-27 | Novartis Ag | derivados de benzamida para a inibição da atividade de abl1, abl2 e bcr-abl1 |
| PE20150669A1 (es) | 2012-05-15 | 2015-05-17 | Novartis Ag | Derivados de benzamida para la inhibicion de la actividad de abl1, abl2 y bcr-abl1 |
| ES2646777T3 (es) * | 2012-05-15 | 2017-12-15 | Novartis Ag | Derivados de pirimidina, piridina y pirazina amida sustituidos con tiazol o imidazol y compuestos relacionados como inhibidores de ABL1, ABL2 y BCR-ABL1 para el tratamiento del cáncer, infecciones víricas específicas y trastornos específicos del CNS |
| BR112014027244A2 (pt) | 2012-05-15 | 2017-06-27 | Novartis Ag | derivados de benzamida para inibição da atividade de abl1, abl2 e bcr-abl1 |
| HUE042374T2 (hu) | 2012-06-13 | 2019-06-28 | Incyte Holdings Corp | Szubsztituált triciklusos vegyületek mint FGFR inhibitorok |
| JP6189948B2 (ja) | 2012-06-29 | 2017-08-30 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規な４−（置換アミノ）−７Ｈ−ピロロ［２，３−ｄ］ピリミジン |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| WO2017156493A1 (en) | 2016-03-11 | 2017-09-14 | Denali Therapeutics Inc. | Compounds, compositions, and methods |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| ES2649156T3 (es) | 2013-01-14 | 2018-01-10 | Incyte Holdings Corporation | Compuestos bicíclicos de carboxamida aromática útiles como inhibidores de quinasas Pim |
| ES2941292T3 (es) | 2013-01-15 | 2023-05-19 | Incyte Holdings Corp | Tiazolecarboxamidas y compuestos de piridinecarboxamida útiles como inhibidores de PIM quinasa |
| WO2014134772A1 (en) * | 2013-03-04 | 2014-09-12 | Merck Sharp & Dohme Corp. | Compounds inhibiting leucine-rich repeat kinase enzyme activity |
| HUE036571T2 (hu) | 2013-04-19 | 2018-07-30 | Incyte Holdings Corp | Biciklusos heterociklusok mint FGFR inhibitorok |
| CN103232394B (zh) * | 2013-05-14 | 2014-09-24 | 浙江医药高等专科学校 | 含吡唑类化合物、其制备方法和用途 |
| CN103387569B (zh) * | 2013-07-16 | 2014-09-24 | 浙江医药高等专科学校 | 一类抗肿瘤化合物、其制备方法和用途 |
| CN103382202B (zh) * | 2013-07-16 | 2014-11-26 | 浙江医药高等专科学校 | 含呋喃取代的化合物、其制备方法和用途 |
| CN103387568B (zh) * | 2013-07-16 | 2014-11-05 | 浙江医药高等专科学校 | 一类化合物、其制备方法和用途 |
| CN103396400B (zh) * | 2013-07-16 | 2014-12-17 | 浙江医药高等专科学校 | 含吡唑酰胺类化合物、其制备方法和用途 |
| CN103420993B (zh) * | 2013-07-16 | 2014-12-17 | 浙江医药高等专科学校 | 含噻吩取代的化合物、其制备方法和用途 |
| CN103382198B (zh) * | 2013-07-16 | 2014-11-19 | 浙江医药高等专科学校 | 吡唑酰胺类化合物、其制备方法和用途 |
| CN104341437A (zh) * | 2013-07-30 | 2015-02-11 | 山东亨利医药科技有限责任公司 | 含有双环基团的syk抑制剂 |
| AR097431A1 (es) | 2013-08-23 | 2016-03-16 | Incyte Corp | Compuestos de carboxamida de furo y tienopiridina útiles como inhibidores de quinasas pim |
| PT3060562T (pt) * | 2013-10-21 | 2021-09-02 | Genosco | Compostos de pirimidina substituídos e sua utilização como inibidores da syk |
| TW201601632A (zh) * | 2013-11-20 | 2016-01-16 | 杜邦股份有限公司 | １－芳基－３－烷基吡唑殺蟲劑 |
| JP6487921B2 (ja) | 2013-12-17 | 2019-03-20 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規の３，４−二置換−１Ｈ−ピロロ［２，３−ｂ］ピリジンおよび４，５−二置換−７Ｈ−ピロロ［２，３−ｃ］ピリダジン |
| CN104974091B (zh) * | 2014-04-10 | 2018-01-02 | 沈阳药科大学 | 3‑甲基‑1,5‑二芳基吡唑类化合物及其制备方法和用途 |
| WO2016007540A2 (en) | 2014-07-10 | 2016-01-14 | The J. David Gladstone Institutes | Compositions and methods for treating dengue virus infection |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| US9822124B2 (en) | 2014-07-14 | 2017-11-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as Pim kinase inhibitors |
| KR101633722B1 (ko) * | 2014-10-08 | 2016-06-28 | 한국화학연구원 | 4-(1-퍼롤-3,4-디카르복시아미드)피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물 |
| HUE054848T2 (hu) | 2014-10-13 | 2021-09-28 | Yuhan Corp | Vegyületek és készítmények EGFR mutáns kináz aktivitás módosítására |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CN104788427B (zh) * | 2015-02-05 | 2017-05-31 | 上海泓博智源医药股份有限公司 | 3‑(2‑嘧啶氨基)苯基丙烯酰胺类化合物及其应用 |
| US10202365B2 (en) | 2015-02-06 | 2019-02-12 | Blueprint Medicines Corporation | 2-(pyridin-3-yl)-pyrimidine derivatives as RET inhibitors |
| MX388991B (es) | 2015-02-20 | 2025-03-20 | Incyte Corp | Heterociclos biciclicos como inhibidores de receptores del factor de crecimiento fibroblastico (fgfr) |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| PL3307727T3 (pl) * | 2015-06-15 | 2024-07-08 | Asana Biosciences, Llc | Heterocykliczne inhibitory erk1 i erk2 oraz ich zastosowanie w leczeniu nowotworów |
| WO2017011776A1 (en) | 2015-07-16 | 2017-01-19 | Array Biopharma, Inc. | Substituted pyrazolo[1,5-a]pyridine compounds as ret kinase inhibitors |
| AR105967A1 (es) | 2015-09-09 | 2017-11-29 | Incyte Corp | Sales de un inhibidor de pim quinasa |
| KR102161364B1 (ko) | 2015-09-14 | 2020-09-29 | 화이자 인코포레이티드 | LRRK2 억제제로서 이미다조[4,5-c]퀴놀린 및 이미다조[4,5-c][1,5]나프티리딘 유도체 |
| US9920032B2 (en) | 2015-10-02 | 2018-03-20 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| MX384884B (es) | 2015-11-02 | 2025-03-14 | Blueprint Medicines Corp | Inhibidores de ret. |
| US11214565B2 (en) | 2015-11-20 | 2022-01-04 | Denali Therapeutics Inc. | Compound, compositions, and methods |
| WO2017161269A1 (en) | 2016-03-17 | 2017-09-21 | Blueprint Medicines Corporation | Inhibitors of ret receptor tyrosine kinases |
| IL299415B2 (en) | 2016-06-16 | 2025-09-01 | Denali Therapeutics Inc | Pyrimidine-2-ylamino-1H-pyrazoles as LRRK2 inhibitors for use in the treatment of neurodegenerative disorders |
| WO2018017983A1 (en) * | 2016-07-22 | 2018-01-25 | Blueprint Medicines Corporation | Compounds useful for treating disorders related to ret |
| US10035789B2 (en) | 2016-07-27 | 2018-07-31 | Blueprint Medicines Corporation | Compounds useful for treating disorders related to RET |
| TWI704148B (zh) | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| JOP20190077A1 (ar) | 2016-10-10 | 2019-04-09 | Array Biopharma Inc | مركبات بيرازولو [1، 5-a]بيريدين بها استبدال كمثبطات كيناز ret |
| MX390348B (es) * | 2016-12-15 | 2025-03-20 | Ariad Pharma Inc | Compuestos de benzimidazol como inhibidores de c-kit |
| JP6888101B2 (ja) | 2017-01-18 | 2021-06-16 | アレイ バイオファーマ インコーポレイテッド | ＲＥＴキナーゼ阻害剤としての置換ピラゾロ［１，５−ａ］ピラジン化合物 |
| WO2018136663A1 (en) | 2017-01-18 | 2018-07-26 | Array Biopharma, Inc. | Ret inhibitors |
| EP3573980A4 (en) * | 2017-01-25 | 2020-08-19 | GlaxoSmithKline Intellectual Property Management Limited | LINKS |
| JOP20190213A1 (ar) | 2017-03-16 | 2019-09-16 | Array Biopharma Inc | مركبات حلقية ضخمة كمثبطات لكيناز ros1 |
| AR111469A1 (es) * | 2017-04-21 | 2019-07-17 | Yuhan Corp | Sal de un compuesto del derivado de aminopiridina, una forma cristalina de la misma, y un proceso para preparar la misma |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| US11472814B2 (en) * | 2017-06-06 | 2022-10-18 | Signalrx Pharmaceuticals, Inc. | Thienopyranones and furanopyranones as checkpoint inhibitors and modulators of anti-tumor immunity |
| MX2022008743A (es) | 2017-07-28 | 2023-02-02 | Yuhan Corp | Proceso mejorado para preparar derivados de aminopirimidina. |
| AU2018308039B2 (en) * | 2017-07-28 | 2022-04-14 | Yuhan Corporation | Novel intermediates useful for the synthesis of aminopyrimidine derivatives, process for preparing the same, and process for preparing aminopyrimidine derivatives using the same |
| MA49705A (fr) | 2017-07-28 | 2021-03-31 | Yuhan Corp | Intermédiaires utiles pour la synthèse d'un inhibiteur sélectif vis-à-vis de la protéine kinase et leurs procédés de préparation |
| TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
| TWI876442B (zh) | 2017-10-10 | 2025-03-11 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| US11472802B2 (en) | 2018-01-18 | 2022-10-18 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridine compounds as RET kinase inhibitors |
| EP3740491A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| US11524963B2 (en) | 2018-01-18 | 2022-12-13 | Array Biopharma Inc. | Substituted pyrazolo[3,4-d]pyrimidines as RET kinase inhibitors |
| EP3773589B1 (en) | 2018-04-03 | 2023-11-01 | Blueprint Medicines Corporation | Ret inhibitor for use in treating cancer having a ret alteration |
| BR112020022373A2 (pt) | 2018-05-04 | 2021-02-02 | Incyte Corporation | sais de um inibidor de fgfr |
| EP3788047B1 (en) | 2018-05-04 | 2024-09-04 | Incyte Corporation | Solid forms of an fgfr inhibitor and processes for preparing the same |
| KR20190131981A (ko) * | 2018-05-18 | 2019-11-27 | 재단법인 대구경북첨단의료산업진흥재단 | 외상성 뇌손상 또는 뇌졸중의 예방 또는 치료용 약학적 조성물 |
| CA3095609A1 (en) | 2018-06-01 | 2019-12-05 | University Of Saskatchewan | Phytochemical-antibiotic combination for the treatment of a bacterial infection |
| EP3849986B1 (en) | 2018-09-10 | 2022-06-08 | Array Biopharma, Inc. | Fused heterocyclic compounds as ret kinase inhibitors |
| CN111285882B (zh) * | 2018-12-07 | 2022-12-02 | 四川科伦博泰生物医药股份有限公司 | 稠环化合物、包含其的药物组合物及其制备方法和用途 |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| CA3137267A1 (en) | 2019-05-01 | 2020-11-05 | Clexio Biosciences Ltd. | Methods of treating pruritus |
| CN112142731B (zh) * | 2019-06-28 | 2022-07-22 | 成都赜灵生物医药科技有限公司 | 一种2，4-二取代嘧啶衍生物及其制备方法和用途 |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| TWI759829B (zh) | 2019-08-23 | 2022-04-01 | 財團法人生物技術開發中心 | 作為第iii型受體酪胺酸激酶抑制劑之雜環吡唑衍生物 |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| KR20220100879A (ko) | 2019-10-14 | 2022-07-18 | 인사이트 코포레이션 | Fgfr 저해제로서의 이환식 헤테로사이클 |
| US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| CA3158910A1 (en) * | 2019-10-28 | 2021-05-06 | Asana Biosciences, Llc | Improved methods, kits, compositions and dosing regimens for the use of heterocyclic inhibitors of erk1 and erk2 |
| KR20220131900A (ko) | 2019-12-04 | 2022-09-29 | 인사이트 코포레이션 | Fgfr 억제제의 유도체 |
| WO2021113479A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| CN118976029A (zh) * | 2019-12-16 | 2024-11-19 | 韩国化学研究院 | 用于预防或治疗帕金森病或非酒精性脂肪性肝炎的药学组合物 |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| KR20230017234A (ko) | 2020-05-29 | 2023-02-03 | 블루프린트 메디신즈 코포레이션 | 프랄세티닙의 고체 형태 |
| US20240285621A1 (en) * | 2020-09-23 | 2024-08-29 | Nerviano Medical Sciences S.R.L. | Pyrazolyl-pyrimidine derivatives as kinase inhibitors |
| US20240174679A1 (en) * | 2021-03-17 | 2024-05-30 | Merck Sharp & Dohme Llc | Heteroaroyl amides as lrrk2 inhibitors, pharmaceutical compositions, and uses thereof |
| WO2022221170A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| CN115368364B (zh) * | 2021-05-19 | 2024-07-16 | 四川大学 | 7H-吡咯并[2,3-d]嘧啶衍生物及其制备方法和用途 |
| TW202313611A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之三環雜環 |
| EP4352060A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| JP2024532835A (ja) * | 2021-08-27 | 2024-09-10 | シャンハイ ハンソー バイオメディカル カンパニー リミテッド | 窒素含有複素環系誘導体阻害剤、その製造方法及び応用 |
| WO2023076404A1 (en) | 2021-10-27 | 2023-05-04 | Aria Pharmaceuticals, Inc. | Methods for treating systemic lupus erythematosus |
| KR102654662B1 (ko) * | 2022-06-13 | 2024-04-05 | 주식회사 이앤피 | 당뇨병 예방 및 치료를 위한 신규 약물(Plk3 억제제)과 관련 물질 개발 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000070523A (ko) * | 1997-01-27 | 2000-11-25 | 스즈키 다다시 | 피라졸 유도체 |
| WO2001060816A1 (en) | 2000-02-17 | 2001-08-23 | Amgen Inc. | Kinase inhibitors |
| EP1558753A2 (en) | 2002-10-16 | 2005-08-03 | Millennium Pharmaceuticals, Inc. | Spleen tyrosine kinase catalytic domain: crystal structure and binding pockets thereof |
| GB0308466D0 (en) * | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| ATE454152T1 (de) * | 2003-06-13 | 2010-01-15 | Novartis Pharma Gmbh | 2-aminopyrimidin-derivate als raf-kinase-hemmer |
| WO2006071644A1 (en) * | 2004-12-23 | 2006-07-06 | Vertex Pharmaceuticals Incorporated | Selective inhibitors of erk protein kinases and uses therof |
| US20080004295A1 (en) * | 2005-10-13 | 2008-01-03 | Gore Paul M | Novel compounds |
| US20100063049A1 (en) * | 2006-05-26 | 2010-03-11 | Clifford Jones | 2-carbocycloamino-4-imidazolylpyrimidines as agents for the inhbition of cell proliferation |
| US20100267707A1 (en) * | 2006-06-22 | 2010-10-21 | Merck Sharp & Dohme Corp. | Tyrosine Kinase Inhibitors |
| WO2008068171A1 (en) * | 2006-12-08 | 2008-06-12 | F. Hoffmann-La Roche Ag | Substituted pyrimidines and their use as jnk modulators |
| WO2009012647A1 (fr) * | 2007-07-20 | 2009-01-29 | Shanghai Hengrui Pharmaceutical Co., Ltd. | Procédés de préparation de dérivés de quinazoline et leurs utilisations pharmaceutiques |
| WO2009032703A1 (en) * | 2007-08-28 | 2009-03-12 | Irm Llc | 2- (het) arylamino-6-aminopyridine derivatives and fused forms thereof as anaplastic lymphoma kinase inhibitors |
| GB0719644D0 (en) * | 2007-10-05 | 2007-11-14 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
-
2010
- 2010-11-12 CA CA2780892A patent/CA2780892C/en active Active
- 2010-11-12 WO PCT/US2010/056583 patent/WO2011060295A1/en not_active Ceased
- 2010-11-12 MX MX2012005332A patent/MX2012005332A/es active IP Right Grant
- 2010-11-12 EA EA201290324A patent/EA024729B1/ru not_active IP Right Cessation
- 2010-11-12 US US12/945,629 patent/US8629132B2/en active Active
- 2010-11-12 JP JP2012539028A patent/JP5740409B2/ja active Active
- 2010-11-12 CN CN201080051548.9A patent/CN102811619B/zh active Active
- 2010-11-12 SG SG10201407453TA patent/SG10201407453TA/en unknown
- 2010-11-12 NZ NZ599041A patent/NZ599041A/en unknown
- 2010-11-12 MY MYPI2012002078A patent/MY160820A/en unknown
- 2010-11-12 BR BR112012011287-2A patent/BR112012011287B1/pt active IP Right Grant
- 2010-11-12 EP EP10830814.9A patent/EP2498607B1/en active Active
- 2010-11-12 KR KR1020127011751A patent/KR101663637B1/ko active Active
-
2012
- 2012-05-10 IL IL219726A patent/IL219726A/en active IP Right Grant
- 2012-05-10 CL CL2012001221A patent/CL2012001221A1/es unknown
- 2012-06-11 ZA ZA2012/04246A patent/ZA201204246B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013510876A5 (enExample) | ||
| RU2497813C2 (ru) | 4-(4-циано-2-тиоарил)-дигидропиримидиноны и их применение | |
| RU2401265C2 (ru) | Соединения и композиции в качестве ингибиторов протеинкиназы | |
| KR101985050B1 (ko) | 피라진카르복사미드 화합물 | |
| JP2017510555A5 (enExample) | ||
| RU2386630C2 (ru) | Соединения и композиции в качестве ингибиторов протеинтирозинкиназы | |
| RU2017104510A (ru) | Соединения, активные по отношению к бромодоменам | |
| JP2017505794A5 (enExample) | ||
| RU2436776C2 (ru) | ДИАРИЛАМИН-СОДЕРЖАЩИЕ СОЕДИНЕНИЯ, КОМПОЗИЦИИ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ МОДУЛЯТОРОВ РЕЦЕПТОРОВ с-КIT | |
| JP2014511869A5 (enExample) | ||
| JP2009541268A5 (enExample) | ||
| JP2017522346A5 (enExample) | ||
| JP2018527336A5 (enExample) | ||
| RU2010110640A (ru) | Соединения и композиции 5-(4-(галогеналкокси)фенил)пиримидин-2-амина в качестве ингибиторов киназ | |
| JP2017525757A5 (enExample) | ||
| JP2008517926A5 (enExample) | ||
| RU2009101911A (ru) | Производные пиридина и пиразина в качестве ингибиторов mnk-киназы | |
| RU2018137194A (ru) | Ингибиторы бромдомена | |
| RU2013133800A (ru) | Селективные к bcl-2 агенты, вызывающие апоптоз, для лечения рака и иммунных заболеваний | |
| JP2019505541A5 (enExample) | ||
| JP2014526549A5 (enExample) | ||
| JP2016517878A5 (enExample) | ||
| MXPA06000444A (es) | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y la profilaxis y tratamiento de desordenes relacionados con los mismos. | |
| WO2017195216A4 (en) | Cyclopropyl-amide compounds as dual lsd1/hdac inhibitors | |
| ME01507B (me) | Imidazotriazini i imidazopirimidini kao inhibitori kinaze |