JP2019529445A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019529445A5 JP2019529445A5 JP2019515477A JP2019515477A JP2019529445A5 JP 2019529445 A5 JP2019529445 A5 JP 2019529445A5 JP 2019515477 A JP2019515477 A JP 2019515477A JP 2019515477 A JP2019515477 A JP 2019515477A JP 2019529445 A5 JP2019529445 A5 JP 2019529445A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dihydro
- thiazol
- amino
- oxo
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- -1 oxetane-3-yl Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- BNXOEOMQSLPCKM-KRWDZBQOSA-N C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=CC=CC(=C2)N2CCCC2=O)S1 Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=CC=CC(=C2)N2CCCC2=O)S1 BNXOEOMQSLPCKM-KRWDZBQOSA-N 0.000 claims 2
- 102000007399 Nuclear hormone receptor Human genes 0.000 claims 2
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 230000003637 steroidlike Effects 0.000 claims 2
- DHEKPZQWFVQYSO-DLBZAZTESA-N (2R)-N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]-2-methoxy-N-methylpropanamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC1=CC=CC(=N1)N(C([C@@H](C)OC)=O)C)C)S(NC)(=O)=O)=O DHEKPZQWFVQYSO-DLBZAZTESA-N 0.000 claims 1
- DHEKPZQWFVQYSO-IRXDYDNUSA-N (2S)-N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]-2-methoxy-N-methylpropanamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC1=CC=CC(=N1)N(C([C@H](C)OC)=O)C)C)S(NC)(=O)=O)=O DHEKPZQWFVQYSO-IRXDYDNUSA-N 0.000 claims 1
- DMIIPYYADLDKAX-HNNXBMFYSA-N 2-[(1S)-1-cyclopropylethyl]-5-[4-methyl-2-[[6-(2-oxoimidazolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-7-methylsulfonyl-3H-isoindol-1-one Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=NC(=CC=C2)N2CCNC2=O)S1 DMIIPYYADLDKAX-HNNXBMFYSA-N 0.000 claims 1
- ZSEKNBCKQHQTBI-INIZCTEOSA-N 2-[(1S)-1-cyclopropylethyl]-5-[4-methyl-2-[[6-(2-oxopiperazin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-7-methylsulfonyl-3H-isoindol-1-one Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=NC(=CC=C2)N2CCNCC2=O)S1 ZSEKNBCKQHQTBI-INIZCTEOSA-N 0.000 claims 1
- SFTPPASPRIXXIN-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-5-[4-methyl-2-[[6-(2-oxopiperidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-7-methylsulfonyl-3H-isoindol-1-one Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=NC(=CC=C2)N2CCCCC2=O)S1 SFTPPASPRIXXIN-KRWDZBQOSA-N 0.000 claims 1
- KVKANZTYGYFKQY-INIZCTEOSA-N 2-[(1S)-1-cyclopropylethyl]-5-[4-methyl-2-[[6-(3-methyl-2-oxoimidazolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-7-methylsulfonyl-3H-isoindol-1-one Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(N(CC1)C)=O)C)S(=O)(=O)C)=O KVKANZTYGYFKQY-INIZCTEOSA-N 0.000 claims 1
- RQZYVAOSDVOURA-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-6-[2-[[6-(3,3-dimethyl-2-oxopiperazin-1-yl)pyridin-2-yl]amino]-4-methyl-1,3-thiazol-5-yl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(C(NCC1)(C)C)=O)C RQZYVAOSDVOURA-KRWDZBQOSA-N 0.000 claims 1
- RQLVMAYHFPSXMR-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-6-[2-[[6-(5,5-dimethyl-2-oxopiperazin-1-yl)pyridin-2-yl]amino]-4-methyl-1,3-thiazol-5-yl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CNC(C1)(C)C)=O)C RQLVMAYHFPSXMR-KRWDZBQOSA-N 0.000 claims 1
- IKNJUYUINPOVDE-OXJNMPFZSA-N 2-[(1S)-1-cyclopropylethyl]-6-[2-[[6-[(2R)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]pyridin-2-yl]amino]-4-methyl-1,3-thiazol-5-yl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1[C@H](CCC1=O)CO)C IKNJUYUINPOVDE-OXJNMPFZSA-N 0.000 claims 1
- IKNJUYUINPOVDE-JXFKEZNVSA-N 2-[(1S)-1-cyclopropylethyl]-6-[2-[[6-[(2S)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]pyridin-2-yl]amino]-4-methyl-1,3-thiazol-5-yl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1[C@@H](CCC1=O)CO)C IKNJUYUINPOVDE-JXFKEZNVSA-N 0.000 claims 1
- UCWFGTHMIDAVDE-HNAYVOBHSA-N 2-[(1S)-1-cyclopropylethyl]-6-[2-[[6-[(3R)-3-hydroxy-2-oxopyrrolidin-1-yl]pyridin-2-yl]amino]-4-methyl-1,3-thiazol-5-yl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C([C@@H](CC1)O)=O)C UCWFGTHMIDAVDE-HNAYVOBHSA-N 0.000 claims 1
- UCWFGTHMIDAVDE-KXBFYZLASA-N 2-[(1S)-1-cyclopropylethyl]-6-[2-[[6-[(3S)-3-hydroxy-2-oxopyrrolidin-1-yl]pyridin-2-yl]amino]-4-methyl-1,3-thiazol-5-yl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C([C@H](CC1)O)=O)C UCWFGTHMIDAVDE-KXBFYZLASA-N 0.000 claims 1
- IUKKLFSDRNELCN-HNAYVOBHSA-N 2-[(1S)-1-cyclopropylethyl]-6-[2-[[6-[(4R)-4-hydroxy-2-oxopyrrolidin-1-yl]pyridin-2-yl]amino]-4-methyl-1,3-thiazol-5-yl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(C[C@H](C1)O)=O)C IUKKLFSDRNELCN-HNAYVOBHSA-N 0.000 claims 1
- RNKHOYDAZIEJFF-SFHVURJKSA-N 2-[(1S)-1-cyclopropylethyl]-6-[2-[[6-[4-(2-hydroxyethyl)-2-oxopiperazin-1-yl]pyridin-2-yl]amino]-4-methyl-1,3-thiazol-5-yl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CN(CC1)CCO)=O)C RNKHOYDAZIEJFF-SFHVURJKSA-N 0.000 claims 1
- JCXVWMWEFKRQCE-INIZCTEOSA-N 2-[(1S)-1-cyclopropylethyl]-6-[4-methyl-2-[[6-(2-oxo-1,3-oxazolidin-3-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-N-(oxetan-3-yl)-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC1COC1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(OCC1)=O)C JCXVWMWEFKRQCE-INIZCTEOSA-N 0.000 claims 1
- VFBCXKOMIUXVNH-INIZCTEOSA-N 2-[(1S)-1-cyclopropylethyl]-6-[4-methyl-2-[[6-(2-oxoimidazolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-N-(oxetan-3-yl)-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC1COC1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(NCC1)=O)C VFBCXKOMIUXVNH-INIZCTEOSA-N 0.000 claims 1
- XLRIOJGDWOEVMT-SFHVURJKSA-N 2-[(1S)-1-cyclopropylethyl]-6-[4-methyl-2-[[6-(2-oxopiperazin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-N-propan-2-yl-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC(C)C)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CNCC1)=O)C XLRIOJGDWOEVMT-SFHVURJKSA-N 0.000 claims 1
- BHFJVMZATJXYCO-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-6-[4-methyl-2-[[6-(2-oxopyrrolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-N-(oxetan-3-yl)-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC1COC1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CCC1)=O)C BHFJVMZATJXYCO-KRWDZBQOSA-N 0.000 claims 1
- ZGQXHYGEONUMTE-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-6-[4-methyl-2-[[6-(3-oxomorpholin-4-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-N-(oxetan-3-yl)-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC1COC1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(COCC1)=O)C ZGQXHYGEONUMTE-KRWDZBQOSA-N 0.000 claims 1
- PZHYYDQKVVSTEG-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-N-ethyl-6-[4-methyl-2-[[6-(2-oxopiperazin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NCC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CNCC1)=O)C PZHYYDQKVVSTEG-KRWDZBQOSA-N 0.000 claims 1
- ZYJKXKZHIIVJEB-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-(2-oxo-1,4-diazepan-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CNCCC1)=O)C ZYJKXKZHIIVJEB-KRWDZBQOSA-N 0.000 claims 1
- SMSOEZUYBOCTCT-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-(2-oxopiperidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CCCC1)=O)C SMSOEZUYBOCTCT-KRWDZBQOSA-N 0.000 claims 1
- FZLQVDKBOUEZHS-INIZCTEOSA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-(3-oxomorpholin-4-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(COCC1)=O)C FZLQVDKBOUEZHS-INIZCTEOSA-N 0.000 claims 1
- QWPSEEVUQYTULG-KRWDZBQOSA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-(7-oxo-1,4-diazepan-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1CCNCCC1=O)C QWPSEEVUQYTULG-KRWDZBQOSA-N 0.000 claims 1
- TYTHLOGWHWLWET-WBVHZDCISA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-[(2R)-2-methyl-6-oxopiperazin-1-yl]pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1[C@@H](CNCC1=O)C)C TYTHLOGWHWLWET-WBVHZDCISA-N 0.000 claims 1
- TYTHLOGWHWLWET-RDJZCZTQSA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-[(2S)-2-methyl-6-oxopiperazin-1-yl]pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1[C@H](CNCC1=O)C)C TYTHLOGWHWLWET-RDJZCZTQSA-N 0.000 claims 1
- KRJCGMRLWBVONG-SJORKVTESA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-[(3R)-3-methyl-2-oxopiperazin-1-yl]pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C([C@H](NCC1)C)=O)C KRJCGMRLWBVONG-SJORKVTESA-N 0.000 claims 1
- KRJCGMRLWBVONG-IRXDYDNUSA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-[(3S)-3-methyl-2-oxopiperazin-1-yl]pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C([C@@H](NCC1)C)=O)C KRJCGMRLWBVONG-IRXDYDNUSA-N 0.000 claims 1
- YXGZTQDPLYDOCC-WBVHZDCISA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-[(5R)-5-methyl-2-oxopiperazin-1-yl]pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CN[C@@H](C1)C)=O)C YXGZTQDPLYDOCC-WBVHZDCISA-N 0.000 claims 1
- YXGZTQDPLYDOCC-RDJZCZTQSA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-6-[4-methyl-2-[[6-[(5S)-5-methyl-2-oxopiperazin-1-yl]pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CN[C@H](C1)C)=O)C YXGZTQDPLYDOCC-RDJZCZTQSA-N 0.000 claims 1
- AICUMEFERAKQDF-KRWDZBQOSA-N 2-[(2S)-3,3-dimethylbutan-2-yl]-N-methyl-6-[4-methyl-2-[[6-(3-oxomorpholin-4-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound CC([C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(COCC1)=O)C)(C)C AICUMEFERAKQDF-KRWDZBQOSA-N 0.000 claims 1
- NDSSKUUMDINTDG-HNNXBMFYSA-N 2-[(2S)-butan-2-yl]-N-methyl-6-[4-methyl-2-[[6-(3-oxomorpholin-4-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C[C@@H](CC)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(COCC1)=O)C NDSSKUUMDINTDG-HNNXBMFYSA-N 0.000 claims 1
- LOYIOALZAFIRRM-UHFFFAOYSA-N 2-tert-butyl-N-methyl-6-[4-methyl-2-[[6-(2-oxo-1,3-oxazinan-3-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-1H-isoindole-4-sulfonamide Chemical compound C(C)(C)(C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(OCCC1)=O)C LOYIOALZAFIRRM-UHFFFAOYSA-N 0.000 claims 1
- TWLBPEXRIJIDLQ-ZDUSSCGKSA-N 3-[6-[[4-methyl-5-[7-methylsulfonyl-1-oxo-2-[(2S)-1,1,1-trifluoropropan-2-yl]-3H-isoindol-5-yl]-1,3-thiazol-2-yl]amino]pyridin-2-yl]-1,3-oxazolidin-2-one Chemical compound C[C@H](N1Cc2cc(cc(c2C1=O)S(C)(=O)=O)-c1sc(Nc2cccc(n2)N2CCOC2=O)nc1C)C(F)(F)F TWLBPEXRIJIDLQ-ZDUSSCGKSA-N 0.000 claims 1
- VLRSVMBPXWKSNE-INIZCTEOSA-N 4-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-methylsulfonyl-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]morpholin-3-one Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(COCC1)=O)C)S(=O)(=O)C)=O VLRSVMBPXWKSNE-INIZCTEOSA-N 0.000 claims 1
- JFUAWXPBHXKZGA-IBGZPJMESA-N 4-fluoro-2-[(4r)-5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C([C@@](O)(CC=1NC2=CN=CC=C2C=1)C(F)(F)F)C(C)(C)C1=CC(F)=CC=C1O JFUAWXPBHXKZGA-IBGZPJMESA-N 0.000 claims 1
- BMEVMMHSZQHXGB-ZDUSSCGKSA-N 5-[4-methyl-2-[[6-(2-oxoimidazolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-7-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]-3H-isoindol-1-one Chemical compound CC=1N=C(SC=1C=1C=C2CN(C(C2=C(C=1)S(=O)(=O)C)=O)[C@H](C(F)(F)F)C)NC1=NC(=CC=C1)N1C(NCC1)=O BMEVMMHSZQHXGB-ZDUSSCGKSA-N 0.000 claims 1
- LLUGOCWVLNJQNI-AWEZNQCLSA-N 5-[4-methyl-2-[[6-(2-oxopyrrolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-7-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]-3H-isoindol-1-one Chemical compound CC=1N=C(SC=1C=1C=C2CN(C(C2=C(C=1)S(=O)(=O)C)=O)[C@H](C(F)(F)F)C)NC1=NC(=CC=C1)N1C(CCC1)=O LLUGOCWVLNJQNI-AWEZNQCLSA-N 0.000 claims 1
- TWMIPMSAUTYVGK-HNNXBMFYSA-N 6-[4-methyl-2-[[6-(2-oxoimidazolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-N-propan-2-yl-2-[(2S)-1,1,1-trifluoropropan-2-yl]-1H-isoindole-4-sulfonamide Chemical compound CC=1N=C(SC=1C=1C=C(C=2C(N(CC=2C=1)[C@H](C(F)(F)F)C)=O)S(=O)(=O)NC(C)C)NC1=NC(=CC=C1)N1C(NCC1)=O TWMIPMSAUTYVGK-HNNXBMFYSA-N 0.000 claims 1
- ZTXDHUWPUMVZCM-INIZCTEOSA-N 6-[4-methyl-2-[[6-(2-oxopiperidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-N-(oxetan-3-yl)-3-oxo-2-[(2S)-1,1,1-trifluoropropan-2-yl]-1H-isoindole-4-sulfonamide Chemical compound CC=1N=C(SC=1C=1C=C(C=2C(N(CC=2C=1)[C@H](C(F)(F)F)C)=O)S(=O)(=O)NC1COC1)NC1=NC(=CC=C1)N1C(CCCC1)=O ZTXDHUWPUMVZCM-INIZCTEOSA-N 0.000 claims 1
- NHOGIGRHHZKFTF-HNNXBMFYSA-N 6-[4-methyl-2-[[6-(2-oxopyrrolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-N-(oxetan-3-yl)-3-oxo-2-[(2S)-1,1,1-trifluoropropan-2-yl]-1H-isoindole-4-sulfonamide Chemical compound CC=1N=C(SC=1C=1C=C(C=2C(N(CC=2C=1)[C@H](C(F)(F)F)C)=O)S(=O)(=O)NC1COC1)NC1=NC(=CC=C1)N1C(CCC1)=O NHOGIGRHHZKFTF-HNNXBMFYSA-N 0.000 claims 1
- VFRMCSHREULMEB-INIZCTEOSA-N 6-[4-methyl-2-[[6-(3-oxomorpholin-4-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-N-propan-2-yl-2-[(2S)-1,1,1-trifluoropropan-2-yl]-1H-isoindole-4-sulfonamide Chemical compound CC=1N=C(SC=1C=1C=C(C=2C(N(CC=2C=1)[C@H](C(F)(F)F)C)=O)S(=O)(=O)NC(C)C)NC1=NC(=CC=C1)N1C(COCC1)=O VFRMCSHREULMEB-INIZCTEOSA-N 0.000 claims 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 1
- RVJDAOWTYAVAHK-INIZCTEOSA-N C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(OCCC1)=O)C Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(OCCC1)=O)C RVJDAOWTYAVAHK-INIZCTEOSA-N 0.000 claims 1
- UUXKXNLWIZYSGT-KRWDZBQOSA-N C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC1COC1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(OCCC1)=O)C Chemical compound C1(CC1)[C@H](C)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC1COC1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(OCCC1)=O)C UUXKXNLWIZYSGT-KRWDZBQOSA-N 0.000 claims 1
- KFNBJCXUFADQNW-INIZCTEOSA-N CC=1N=C(SC=1C=1C=C(C=2C(N(CC=2C=1)[C@H](C(F)(F)F)C)=O)S(=O)(=O)NC(C)C)NC1=NC(=CC=C1)N1C(OCCC1)=O Chemical compound CC=1N=C(SC=1C=1C=C(C=2C(N(CC=2C=1)[C@H](C(F)(F)F)C)=O)S(=O)(=O)NC(C)C)NC1=NC(=CC=C1)N1C(OCCC1)=O KFNBJCXUFADQNW-INIZCTEOSA-N 0.000 claims 1
- XCOQTFFMFTWVMC-INIZCTEOSA-N C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=NC(=CC=C2)N2CCCOC2=O)S1 Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=NC(=CC=C2)N2CCCOC2=O)S1 XCOQTFFMFTWVMC-INIZCTEOSA-N 0.000 claims 1
- NTZMWNKORQPPBL-HNNXBMFYSA-N C[C@@H](CC)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(OCCC1)=O)C Chemical compound C[C@@H](CC)N1CC=2C=C(C=C(C=2C1=O)S(=O)(=O)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(OCCC1)=O)C NTZMWNKORQPPBL-HNNXBMFYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 1
- TZUURZCAUFJVTJ-KRWDZBQOSA-N N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-(ethylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]-2-methoxy-N-methylacetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC1=CC=CC(=N1)N(C(COC)=O)C)C)S(NCC)(=O)=O)=O TZUURZCAUFJVTJ-KRWDZBQOSA-N 0.000 claims 1
- FLUPYHUXCIWKAE-KRWDZBQOSA-N N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]-2-ethoxy-N-methylacetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC1=CC=CC(=N1)N(C(COCC)=O)C)C)S(NC)(=O)=O)=O FLUPYHUXCIWKAE-KRWDZBQOSA-N 0.000 claims 1
- YAOHUGMVFAJBNE-INIZCTEOSA-N N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]-2-methoxy-N-methylacetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC1=CC=CC(=N1)N(C(COC)=O)C)C)S(NC)(=O)=O)=O YAOHUGMVFAJBNE-INIZCTEOSA-N 0.000 claims 1
- WEMBXYLJGBGCSQ-HNNXBMFYSA-N N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]-N-methylacetamide Chemical compound CNS(=O)(=O)C1=C2C(CN([C@@H](C)C3CC3)C2=O)=CC(=C1)C1=C(C)N=C(NC2=CC=CC(=N2)N(C)C(C)=O)S1 WEMBXYLJGBGCSQ-HNNXBMFYSA-N 0.000 claims 1
- KWHLMLQDUKNHBO-HNNXBMFYSA-N N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-methylsulfonyl-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]-N-methylacetamide Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=CC=CC(=N2)N(C)C(C)=O)S1 KWHLMLQDUKNHBO-HNNXBMFYSA-N 0.000 claims 1
- VGBZVXNIRCSRBK-AWEZNQCLSA-N N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-methylsulfonyl-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]acetamide Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=CC=CC(NC(C)=O)=N2)S1 VGBZVXNIRCSRBK-AWEZNQCLSA-N 0.000 claims 1
- XDWSNPNGAFALHJ-HNNXBMFYSA-N N-ethyl-6-[4-methyl-2-[[6-(3-oxomorpholin-4-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-2-[(2S)-1,1,1-trifluoropropan-2-yl]-1H-isoindole-4-sulfonamide Chemical compound C(C)NS(=O)(=O)C=1C=2C(N(CC=2C=C(C=1)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(COCC1)=O)C)[C@H](C(F)(F)F)C)=O XDWSNPNGAFALHJ-HNNXBMFYSA-N 0.000 claims 1
- GFTIJVHUHAMPLS-AWEZNQCLSA-N N-methyl-6-[4-methyl-2-[[6-(2-oxopyrrolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-3-oxo-2-[(2S)-1,1,1-trifluoropropan-2-yl]-1H-isoindole-4-sulfonamide Chemical compound CNS(=O)(=O)c1cc(cc2CN([C@@H](C)C(F)(F)F)C(=O)c12)-c1sc(Nc2cccc(n2)N2CCCC2=O)nc1C GFTIJVHUHAMPLS-AWEZNQCLSA-N 0.000 claims 1
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000003149 muscarinic antagonist Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662398006P | 2016-09-22 | 2016-09-22 | |
| US62/398,006 | 2016-09-22 | ||
| PCT/EP2017/073916 WO2018055040A1 (en) | 2016-09-22 | 2017-09-21 | 5-[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]-2,3-dihydro-1 h-isoindol-1 -one derivatives and their use as dual inhibitors of phosphatidylinositol 3-kinase delta & gamma |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019529445A JP2019529445A (ja) | 2019-10-17 |
| JP2019529445A5 true JP2019529445A5 (enExample) | 2020-05-14 |
| JP6765516B2 JP6765516B2 (ja) | 2020-10-07 |
Family
ID=59966739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019515477A Expired - Fee Related JP6765516B2 (ja) | 2016-09-22 | 2017-09-21 | ５−［２−（ピリジン−２−イルアミノ）−１，３−チアゾール−５−イル］−２，３−ジヒドロ−１ｈ−イソインドール−１−オン誘導体ならびにホスファチジルイノシトール３−キナーゼデルタおよびガンマの二重阻害剤としてのその使用 |
Country Status (36)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11161838B2 (en) | 2018-11-13 | 2021-11-02 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
| US11396502B2 (en) | 2018-11-13 | 2022-07-26 | Incyte Corporation | Substituted heterocyclic derivatives as PI3K inhibitors |
| US11078204B2 (en) | 2018-11-13 | 2021-08-03 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
| CN115677692A (zh) * | 2019-04-10 | 2023-02-03 | 南京征祥医药有限公司 | 磷脂酰肌醇3-激酶抑制剂 |
| JP7665534B2 (ja) | 2019-06-04 | 2025-04-21 | アーカス バイオサイエンシーズ インコーポレイテッド | ２，３，５－三置換ピラゾロ［１，５－ａ］ピリミジン化合物 |
| CN114258393B (zh) * | 2020-07-21 | 2024-11-22 | 中国医药研究开发中心有限公司 | 具有磷脂酰肌醇3-激酶δ和γ的双重抑制剂活性的杂环化合物及其医药用途 |
| WO2022023456A1 (en) | 2020-07-29 | 2022-02-03 | Astrazeneca Ab | Pharmaceutical compositions comprising nano embedded microparticles and methods of use |
| CN116813608B (zh) * | 2023-06-08 | 2024-03-22 | 英矽智能科技(上海)有限公司 | 噻唑类化合物及其应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2257461T3 (es) * | 2000-12-21 | 2006-08-01 | Bristol-Myers Squibb Company | Inhibidores de tiazolilo de tirosina quinasas de la familia tec. |
| GB0305152D0 (en) * | 2003-03-06 | 2003-04-09 | Novartis Ag | Organic compounds |
| GB0320197D0 (en) * | 2003-08-28 | 2003-10-01 | Novartis Ag | Organic compounds |
| CA2610884A1 (en) * | 2005-06-09 | 2006-12-21 | Merck & Co., Inc. | Inhibitors of checkpoint kinases |
| JP5561702B2 (ja) * | 2007-08-02 | 2014-07-30 | アムジエン・インコーポレーテツド | Ｐｉ３キナーゼ調節剤および使用方法 |
| UY33337A (es) | 2010-10-18 | 2011-10-31 | Respivert Ltd | DERIVADOS SUSTITUIDOS DE 1H-PIRAZOL[ 3,4-d]PIRIMIDINA COMO INHIBIDORES DE LAS FOSFOINOSITIDA 3-QUINASAS |
| CA2842190A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| JP6027610B2 (ja) | 2011-07-19 | 2016-11-16 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | 複素環式化合物及びその使用 |
| CN103998442B (zh) | 2011-08-29 | 2016-09-14 | 无限药品股份有限公司 | 杂环化合物及其用途 |
| CA2850763A1 (en) | 2011-10-04 | 2013-04-11 | Gilead Calistoga Llc | Novel quinoxaline inhibitors of pi3k |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| AR094797A1 (es) | 2013-02-15 | 2015-08-26 | Almirall Sa | Derivados de pirrolotriazina como inhibidores de pi3k |
| JP6371838B2 (ja) | 2013-07-02 | 2018-08-08 | ライゼン・ファーマシューティカルズ・エスアー | Ｐｉ３ｋタンパク質キナーゼ阻害剤、特に、デルタ及び／またはガンマ阻害剤 |
| UY35675A (es) | 2013-07-24 | 2015-02-27 | Novartis Ag | Derivados sustituidos de quinazolin-4-ona |
| EA031135B1 (ru) | 2014-06-27 | 2018-11-30 | Ризен Фармасьютикалз Са | Замещенные производные хромена как селективные двойные ингибиторы протеинкиназ pi3 дельта и гамма |
-
2017
- 2017-06-16 JO JOP/2019/0052A patent/JOP20190052A1/ar unknown
- 2017-09-21 DK DK17772381.4T patent/DK3515910T3/da active
- 2017-09-21 EA EA201990664A patent/EA036176B1/ru not_active IP Right Cessation
- 2017-09-21 HU HUE17772381A patent/HUE051634T2/hu unknown
- 2017-09-21 TW TW106132359A patent/TW201813967A/zh unknown
- 2017-09-21 WO PCT/EP2017/073916 patent/WO2018055040A1/en not_active Ceased
- 2017-09-21 AU AU2017331940A patent/AU2017331940B2/en not_active Ceased
- 2017-09-21 KR KR1020197010973A patent/KR102226098B1/ko not_active Expired - Fee Related
- 2017-09-21 MX MX2019003194A patent/MX381898B/es unknown
- 2017-09-21 PE PE2019000702A patent/PE20190909A1/es unknown
- 2017-09-21 EP EP17772381.4A patent/EP3515910B1/en active Active
- 2017-09-21 LT LTEP17772381.4T patent/LT3515910T/lt unknown
- 2017-09-21 US US16/332,620 patent/US10961236B2/en not_active Expired - Fee Related
- 2017-09-21 MA MA46268A patent/MA46268B1/fr unknown
- 2017-09-21 CA CA3036304A patent/CA3036304A1/en not_active Abandoned
- 2017-09-21 JP JP2019515477A patent/JP6765516B2/ja not_active Expired - Fee Related
- 2017-09-21 PT PT177723814T patent/PT3515910T/pt unknown
- 2017-09-21 UA UAA201903648A patent/UA123558C2/uk unknown
- 2017-09-21 ES ES17772381T patent/ES2818583T3/es active Active
- 2017-09-21 CR CR20190200A patent/CR20190200A/es unknown
- 2017-09-21 BR BR112019004719A patent/BR112019004719A2/pt not_active IP Right Cessation
- 2017-09-21 CN CN201780057289.2A patent/CN109715623A/zh active Pending
- 2017-09-21 HR HRP20201175TT patent/HRP20201175T1/hr unknown
- 2017-09-21 SM SM20200481T patent/SMT202000481T1/it unknown
- 2017-09-21 SI SI201730357T patent/SI3515910T1/sl unknown
- 2017-09-21 RS RS20201077A patent/RS60764B1/sr unknown
- 2017-09-21 PL PL17772381.4T patent/PL3515910T3/pl unknown
- 2017-09-22 AR ARP170102631A patent/AR109706A1/es unknown
-
2019
- 2019-03-11 IL IL265298A patent/IL265298B/en active IP Right Grant
- 2019-03-19 CL CL2019000707A patent/CL2019000707A1/es unknown
- 2019-03-20 MX MX2021004748A patent/MX2021004748A/es unknown
- 2019-03-20 DO DO2019000073A patent/DOP2019000073A/es unknown
- 2019-03-21 PH PH12019500615A patent/PH12019500615A1/en unknown
- 2019-03-22 SV SV2019005857A patent/SV2019005857A/es unknown
- 2019-04-08 CO CONC2019/0003440A patent/CO2019003440A2/es unknown
- 2019-04-17 EC ECSENADI201927780A patent/ECSP19027780A/es unknown
-
2020
- 2020-09-09 CY CY20201100856T patent/CY1123346T1/el unknown
-
2021
- 2021-02-11 US US17/173,826 patent/US20210246130A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019529445A5 (enExample) | ||
| HRP20201175T1 (hr) | Derivati 5-[2-(piridin-2-ilamino)-1,3-tiazol-5-il]-2,3-dihidro-1h-izoindol-1-ona i njihova upotreba kao dvostrukih inhibitora fosfatidilinozitola 3-kinaze delta i gama | |
| JP6162144B2 (ja) | ４，４−二置換−１，４−ジヒドロピリミジン、及びｂ型肝炎の処置のための医薬としてのその使用 | |
| JP2018536671A5 (enExample) | ||
| AU2012356374B2 (en) | Pyridinone and pyrimidinone derivatives as factor XIa inhibitors | |
| HRP20201469T1 (hr) | Derivati tetrahidroizokinolina | |
| JP2013545744A5 (enExample) | ||
| RU2018138707A (ru) | Замещенные гетероарилом пиридины и способы применения | |
| JP2016523911A5 (enExample) | ||
| JP2017505762A5 (enExample) | ||
| JP2011503230A5 (enExample) | ||
| RU2019132212A (ru) | Селективные ингибиторы hdac6 | |
| JP2009524670A5 (enExample) | ||
| IL187690A (en) | Derivatives 1, 2, 4 - Triazolo - 1, 6 - Naphthiridines as inhibitors of AKT activity for use in the preparation of drugs for the treatment of cancer | |
| JP2017532364A5 (enExample) | ||
| JP2020516671A5 (enExample) | ||
| JP2018535999A5 (enExample) | ||
| JP2015528022A5 (enExample) | ||
| JP2017530185A5 (enExample) | ||
| JP2012532931A5 (enExample) | ||
| HRP20211960T1 (hr) | Alosterični modulatori nikotinskih acetilcolinskih receptora | |
| RU2012105284A (ru) | Спиро-аминосоединения, пригодные для лечения нарушений сна и лекарственного привыкания | |
| RU2015111133A (ru) | Ингибиторы тирозинкиназы брутона | |
| JP2018507234A5 (enExample) | ||
| JP2018515525A5 (enExample) |