CA3036304A1 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- CA3036304A1 CA3036304A1 CA3036304A CA3036304A CA3036304A1 CA 3036304 A1 CA3036304 A1 CA 3036304A1 CA 3036304 A CA3036304 A CA 3036304A CA 3036304 A CA3036304 A CA 3036304A CA 3036304 A1 CA3036304 A1 CA 3036304A1
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- Canada
- Prior art keywords
- methyl
- dihydro
- thiazol
- oxo
- pyridin
- 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.)
- Abandoned
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- 108091007960 PI3Ks Proteins 0.000 title abstract description 16
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 title abstract description 14
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 title abstract 3
- 239000003112 inhibitor Substances 0.000 title description 16
- 230000009977 dual effect Effects 0.000 title description 10
- JTEFIQCSVCKGDP-UHFFFAOYSA-N 5-[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]-2,3-dihydroisoindol-1-one Chemical class N1=C(C=CC=C1)NC=1SC(=CN=1)C=1C=C2CNC(C2=CC=1)=O JTEFIQCSVCKGDP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 227
- 150000003839 salts Chemical class 0.000 claims abstract description 77
- 238000000034 method Methods 0.000 claims abstract description 53
- 208000006673 asthma Diseases 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 22
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 118
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 68
- -1 2-oxopyrrolidin-1-yl Chemical group 0.000 claims description 40
- 239000003814 drug Substances 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
- 230000003637 steroidlike Effects 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 239000000048 adrenergic agonist Substances 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000003149 muscarinic antagonist Substances 0.000 claims description 4
- 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 description 3
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims description 3
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims description 2
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 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
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 2
- 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
- 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
- ZWZBXYCUIUOCOO-INIZCTEOSA-N 2-[(1S)-1-cyclopropylethyl]-N-methyl-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)NC)C1=C(N=C(S1)NC1=NC(=CC=C1)N1C(CNCC1)=O)C ZWZBXYCUIUOCOO-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
- 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
- ZAWKCTQNKKDNMQ-YJBOKZPZSA-N 6-[2-[[6-[(3S)-3-hydroxy-2-oxopyrrolidin-1-yl]pyridin-2-yl]amino]-4-methyl-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 O[C@@H]1C(N(CC1)C1=CC=CC(=N1)NC=1SC(=C(N=1)C)C=1C=C(C=2C(N(CC=2C=1)[C@H](C(F)(F)F)C)=O)S(=O)(=O)NC(C)C)=O ZAWKCTQNKKDNMQ-YJBOKZPZSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA3036304A1 true CA3036304A1 (en) | 2018-03-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3036304A Abandoned CA3036304A1 (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 |
Country Status (36)
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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 |
| WO2020102198A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Heterocyclic derivatives as pi3k inhibitors |
| WO2020210379A1 (en) * | 2019-04-10 | 2020-10-15 | Hangzhou Zhengxiang Pharmaceuticals Co., Ltd. | Phosphatidylinositol 3-kinase inhibitors |
| AU2020288610A1 (en) | 2019-06-04 | 2022-01-27 | Arcus Biosciences, Inc. | 2,3,5-trisubstituted pyrazolo[1,5-a]pyrimidine compounds |
| 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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| 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 |
| JP2008543754A (ja) * | 2005-06-09 | 2008-12-04 | メルク エンド カムパニー インコーポレーテッド | チェックポイントキナーゼの阻害剤 |
| US7928140B2 (en) * | 2007-08-02 | 2011-04-19 | Amgen Inc. | Benzothiazole PI3 kinase modulators for cancer treatment |
| 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 |
| EP2734520B1 (en) | 2011-07-19 | 2016-09-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US9056877B2 (en) | 2011-07-19 | 2015-06-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| PE20141371A1 (es) | 2011-08-29 | 2014-10-13 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos |
| EP2763994A4 (en) | 2011-10-04 | 2015-08-26 | Gilead Calistoga Llc | NEW QUINOXALINE INHIBITORS OF THE PI3K PATH |
| 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 |
| ES2672018T3 (es) | 2013-07-02 | 2018-06-12 | Rhizen Pharmaceuticals S.A. | Inhibidores de proteína cinasa PI3K, particularmente inhibidores delta y/o gamma |
| UY35675A (es) | 2013-07-24 | 2015-02-27 | Novartis Ag | Derivados sustituidos de quinazolin-4-ona |
| CN106661029B (zh) | 2014-06-27 | 2019-04-05 | 理森制药股份公司 | 作为PI3δ和γ蛋白激酶的选择性双重抑制剂的取代色烯衍生物 |
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2017
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- 2017-09-21 UA UAA201903648A patent/UA123558C2/uk unknown
- 2017-09-21 CR CR20190200A patent/CR20190200A/es unknown
- 2017-09-21 PT PT177723814T patent/PT3515910T/pt unknown
- 2017-09-21 CN CN201780057289.2A patent/CN109715623A/zh active Pending
- 2017-09-21 PE PE2019000702A patent/PE20190909A1/es unknown
- 2017-09-21 US US16/332,620 patent/US10961236B2/en not_active Expired - Fee Related
- 2017-09-21 RS RS20201077A patent/RS60764B1/sr unknown
- 2017-09-21 PL PL17772381.4T patent/PL3515910T3/pl 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 SI SI201730357T patent/SI3515910T1/sl unknown
- 2017-09-21 MX MX2019003194A patent/MX381898B/es unknown
- 2017-09-21 MA MA46268A patent/MA46268B1/fr unknown
- 2017-09-21 HR HRP20201175TT patent/HRP20201175T1/hr unknown
- 2017-09-21 SM SM20200481T patent/SMT202000481T1/it unknown
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- 2017-09-21 DK DK17772381.4T patent/DK3515910T3/da active
- 2017-09-21 CA CA3036304A patent/CA3036304A1/en not_active Abandoned
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2019
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2020
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2021
- 2021-02-11 US US17/173,826 patent/US20210246130A1/en not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20240103 |