JP2019529445A5 - - Google Patents
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- 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.)
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 239000003085 diluting agent Substances 0.000 claims 1
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- 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
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| 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 |
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| US11161838B2 (en) | 2018-11-13 | 2021-11-02 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
| WO2020102216A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Substituted heterocyclic derivatives as pi3k inhibitors |
| US11078204B2 (en) | 2018-11-13 | 2021-08-03 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
| EP3952870B1 (en) * | 2019-04-10 | 2025-09-24 | Nanjing Zenshine Pharmaceuticals Co., Ltd. | Phosphatidylinositol 3-kinase inhibitors |
| KR20220047247A (ko) | 2019-06-04 | 2022-04-15 | 아르커스 바이오사이언시즈 인코포레이티드 | 2,3,5-삼치환 피라졸로[1,5-a]피리미딘 화합물 |
| WO2022017371A1 (zh) * | 2020-07-21 | 2022-01-27 | 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 |
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| AU2006258101A1 (en) * | 2005-06-09 | 2006-12-21 | Merck Sharp & Dohme Corp. | Inhibitors of checkpoint kinases |
| AU2008282728B2 (en) * | 2007-08-02 | 2012-04-19 | Amgen Inc. | Pl3 kinase modulators and methods of use |
| 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 |
| MX2014000648A (es) | 2011-07-19 | 2014-09-25 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y sus usos. |
| WO2013012915A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| KR20140075693A (ko) | 2011-08-29 | 2014-06-19 | 인피니티 파마슈티칼스, 인코포레이티드 | 헤테로사이클릭 화합물 및 그의 용도 |
| JP2014528451A (ja) | 2011-10-04 | 2014-10-27 | ギリアード カリストガ エルエルシー | Ｐｉ３ｋの新規キノキサリン阻害剤 |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| TW201446767A (zh) | 2013-02-15 | 2014-12-16 | Almirall Sa | 作為磷脂肌醇3-激酶抑製劑之吡咯並三嗪衍生物 |
| CN105431437B (zh) | 2013-07-02 | 2020-03-10 | 理森制药股份公司 | PI3K蛋白激酶抑制剂，特别是δ抑制剂和/或γ抑制剂 |
| UY35675A (es) | 2013-07-24 | 2015-02-27 | Novartis Ag | Derivados sustituidos de quinazolin-4-ona |
| AU2015278699B2 (en) | 2014-06-27 | 2019-10-31 | Rhizen Pharmaceuticals Sa | Substituted chromene derivatives as selective dual inhibitors of PI3 delta and gamma protein kinases |
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