JP2019507788A5 - - Google Patents
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- Publication number
- JP2019507788A5 JP2019507788A5 JP2018547461A JP2018547461A JP2019507788A5 JP 2019507788 A5 JP2019507788 A5 JP 2019507788A5 JP 2018547461 A JP2018547461 A JP 2018547461A JP 2018547461 A JP2018547461 A JP 2018547461A JP 2019507788 A5 JP2019507788 A5 JP 2019507788A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- oxo
- methyl
- acetamide
- thiazol
- 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
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- -1 3,3-dimethylbutan-2-yl Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- DPDJXTANWGNJOE-UHFFFAOYSA-N n-(4-methyl-1,3-thiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NC(C)=CS1 DPDJXTANWGNJOE-UHFFFAOYSA-N 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 102000007399 Nuclear hormone receptor Human genes 0.000 claims 3
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- PAQUFWFUOVDUIO-NSHDSACASA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-methylsulfonyl-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C[C@@H](C1CC1)N1Cc2cc(cc(c2C1=O)S(C)(=O)=O)-c1sc(NC(C)=O)nc1C PAQUFWFUOVDUIO-NSHDSACASA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000003637 steroidlike Effects 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
- SJEXQETYPPZBHL-NSHDSACASA-N 6-(8-aminoimidazo[1,2-a]pyrazin-3-yl)-2-[(1S)-1-cyclopropylethyl]-N-methyl-3-oxo-1H-isoindole-4-sulfonamide Chemical compound NC=1C=2N(C=CN=1)C(=CN=2)C=1C=C(C=2C(N(CC=2C=1)[C@@H](C)C1CC1)=O)S(=O)(=O)NC SJEXQETYPPZBHL-NSHDSACASA-N 0.000 claims 1
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 1
- SPHSTKAWSDHNTR-UHFFFAOYSA-N N-[4-methyl-5-[7-(methylsulfamoyl)-1-oxo-2-propan-2-yl-3H-isoindol-5-yl]-1,3-thiazol-2-yl]acetamide Chemical compound C(C)(=O)NC=1SC(=C(N=1)C)C=1C=C2CN(C(C2=C(C=1)S(NC)(=O)=O)=O)C(C)C SPHSTKAWSDHNTR-UHFFFAOYSA-N 0.000 claims 1
- OVIDTSZSCQBFIR-UHFFFAOYSA-N N-[5-[2-(2-cyclopropylpropan-2-yl)-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound CNS(=O)(=O)C1=C2C(CN(C2=O)C(C)(C)C2CC2)=CC(=C1)C1=C(C)N=C(NC(C)=O)S1 OVIDTSZSCQBFIR-UHFFFAOYSA-N 0.000 claims 1
- XYBWLKSKPRPPLU-ZDUSSCGKSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-1-oxo-7-(propylsulfonylamino)-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC(C)=O)C)NS(=O)(=O)CCC)=O XYBWLKSKPRPPLU-ZDUSSCGKSA-N 0.000 claims 1
- BUSUJVPSSIGJOU-VIFPVBQESA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-1-oxo-7-sulfamoyl-3H-isoindol-5-yl]-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=CN=C(S1)NC(C)=O)S(N)(=O)=O)=O BUSUJVPSSIGJOU-VIFPVBQESA-N 0.000 claims 1
- NHFRWRZPNNFBRN-JTQLQIEISA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-1-oxo-7-sulfamoyl-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C[C@@H](C1CC1)N1Cc2cc(cc(c2C1=O)S(N)(=O)=O)-c1sc(NC(C)=O)nc1C NHFRWRZPNNFBRN-JTQLQIEISA-N 0.000 claims 1
- CYXPQVSTQNRNSH-ZDUSSCGKSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(2-methoxyethylsulfonylamino)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound COCCS(=O)(=O)NC1=C2C(=O)N(CC2=CC(=C1)C1=C(C)N=C(NC(C)=O)S1)[C@@H](C)C1CC1 CYXPQVSTQNRNSH-ZDUSSCGKSA-N 0.000 claims 1
- VLABTWADXZLQMK-ZDUSSCGKSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(cyclopropylmethylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC(C)=O)C)S(NCC1CC1)(=O)=O)=O VLABTWADXZLQMK-ZDUSSCGKSA-N 0.000 claims 1
- ZKNGXRWHBHUFFL-ZDUSSCGKSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(cyclopropylmethylsulfonylamino)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC(C)=O)C)NS(=O)(=O)CC1CC1)=O ZKNGXRWHBHUFFL-ZDUSSCGKSA-N 0.000 claims 1
- FAJGOXNQQGYUDP-LBPRGKRZSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(cyclopropylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC(C)=O)C)S(NC1CC1)(=O)=O)=O FAJGOXNQQGYUDP-LBPRGKRZSA-N 0.000 claims 1
- CHJGVMAJIMJZLF-LBPRGKRZSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(cyclopropylsulfonylamino)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC(C)=O)C)NS(=O)(=O)C1CC1)=O CHJGVMAJIMJZLF-LBPRGKRZSA-N 0.000 claims 1
- BSKVHKARSUYCGJ-LBPRGKRZSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(dimethylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C[C@@H](C1CC1)N1Cc2cc(cc(c2C1=O)S(=O)(=O)N(C)C)-c1sc(NC(C)=O)nc1C BSKVHKARSUYCGJ-LBPRGKRZSA-N 0.000 claims 1
- HAQLVYJPYSPVRP-LBPRGKRZSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(ethylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC(C)=O)C)S(NCC)(=O)=O)=O HAQLVYJPYSPVRP-LBPRGKRZSA-N 0.000 claims 1
- HAGXXLPBUWREIV-LBPRGKRZSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(ethylsulfonylamino)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC(C)=O)C)NS(=O)(=O)CC)=O HAGXXLPBUWREIV-LBPRGKRZSA-N 0.000 claims 1
- HCUUTTWVCUCZBP-JTQLQIEISA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(methanesulfonamido)-1-oxo-3H-isoindol-5-yl]-1,3-thiazol-2-yl]acetamide Chemical compound C1(CC1)[C@H](C)N1C(C2=C(C=C(C=C2C1)C1=CN=C(S1)NC(C)=O)NS(=O)(=O)C)=O HCUUTTWVCUCZBP-JTQLQIEISA-N 0.000 claims 1
- RMZMULPZUXWJGE-NSHDSACASA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(methanesulfonamido)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C[C@@H](C1CC1)N1Cc2cc(cc(NS(C)(=O)=O)c2C1=O)-c1sc(NC(C)=O)nc1C RMZMULPZUXWJGE-NSHDSACASA-N 0.000 claims 1
- XMXMALSWJFWHNV-JTQLQIEISA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-1,3-thiazol-2-yl]acetamide Chemical compound CNS(=O)(=O)c1cc(cc2CN([C@@H](C)C3CC3)C(=O)c12)-c1cnc(NC(C)=O)s1 XMXMALSWJFWHNV-JTQLQIEISA-N 0.000 claims 1
- LHKIAELCKQHVBI-NSHDSACASA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound CNS(=O)(=O)c1cc(cc2CN([C@@H](C)C3CC3)C(=O)c12)-c1sc(NC(C)=O)nc1C LHKIAELCKQHVBI-NSHDSACASA-N 0.000 claims 1
- WAZBHQMUCRGFMW-AWEZNQCLSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-[(1,3-dimethylpyrazol-4-yl)sulfonylamino]-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(NS(=O)(=O)C3=CN(C)N=C3C)=C2C1=O)C1=C(C)N=C(NC(C)=O)S1 WAZBHQMUCRGFMW-AWEZNQCLSA-N 0.000 claims 1
- KLBWDODQEVMJRQ-HNNXBMFYSA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-[[1-(2-fluoroethyl)cyclopropyl]methylsulfamoyl]-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound CC1=C(SC(=N1)NC(=O)C)C2=CC3=C(C(=C2)S(=O)(=O)NCC4(CC4)CCF)C(=O)N(C3)[C@@H](C)C5CC5 KLBWDODQEVMJRQ-HNNXBMFYSA-N 0.000 claims 1
- CFJLBFJSVLACGY-JTQLQIEISA-N N-[5-[2-[(1S)-1-cyclopropylethyl]-7-methylsulfonyl-1-oxo-3H-isoindol-5-yl]-1,3-thiazol-2-yl]acetamide Chemical compound C(C)(=O)NC=1SC(=CN=1)C=1C=C2CN(C(C2=C(C=1)S(=O)(=O)C)=O)[C@@H](C)C1CC1 CFJLBFJSVLACGY-JTQLQIEISA-N 0.000 claims 1
- OFCXXWXNDOBWNJ-LBPRGKRZSA-N N-[5-[2-[(2S)-3,3-dimethylbutan-2-yl]-7-(methylsulfamoyl)-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound CC([C@H](C)N1C(C2=C(C=C(C=C2C1)C1=C(N=C(S1)NC(C)=O)C)S(NC)(=O)=O)=O)(C)C OFCXXWXNDOBWNJ-LBPRGKRZSA-N 0.000 claims 1
- NCZPTALQUZPCMT-ZDUSSCGKSA-N N-[5-[7-(cyclobutylsulfamoyl)-2-[(1S)-1-cyclopropylethyl]-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound C1(CCC1)NS(=O)(=O)C=1C=C(C=C2CN(C(C=12)=O)[C@@H](C)C1CC1)C1=C(N=C(S1)NC(C)=O)C NCZPTALQUZPCMT-ZDUSSCGKSA-N 0.000 claims 1
- UZLFZCSKAVBUNG-NSHDSACASA-N N-[6-(2-acetamido-4-methyl-1,3-thiazol-5-yl)-2-[(1S)-1-cyclopropylethyl]-3-oxo-1H-isoindol-4-yl]acetamide Chemical compound C(C)(=O)NC=1C=C(C=C2CN(C(C=12)=O)[C@@H](C)C1CC1)C1=C(N=C(S1)NC(C)=O)C UZLFZCSKAVBUNG-NSHDSACASA-N 0.000 claims 1
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 1
- 229940124639 Selective inhibitor Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 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
- 230000001022 anti-muscarinic effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000003149 muscarinic antagonist Substances 0.000 claims 1
- WXPLRSVMGRAIGW-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NC=CS1 WXPLRSVMGRAIGW-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662306328P | 2016-03-10 | 2016-03-10 | |
| US62/306,328 | 2016-03-10 | ||
| PCT/EP2017/055552 WO2017153527A1 (en) | 2016-03-10 | 2017-03-09 | Novel inhibitors of phosphatidylinositol 3-kinase gamma |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019507788A JP2019507788A (ja) | 2019-03-22 |
| JP2019507788A5 true JP2019507788A5 (https=) | 2020-03-05 |
| JP6893520B2 JP6893520B2 (ja) | 2021-06-23 |
Family
ID=58264542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018547461A Expired - Fee Related JP6893520B2 (ja) | 2016-03-10 | 2017-03-09 | ホスファチジルイノシトール３−キナーゼガンマの新規の阻害剤 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10858355B2 (https=) |
| EP (1) | EP3426652B1 (https=) |
| JP (1) | JP6893520B2 (https=) |
| KR (1) | KR20180117693A (https=) |
| CN (1) | CN108779110B (https=) |
| AR (1) | AR107840A1 (https=) |
| AU (1) | AU2017229445B2 (https=) |
| BR (1) | BR112018068075A2 (https=) |
| CA (1) | CA3015893C (https=) |
| EA (1) | EA036388B1 (https=) |
| MX (1) | MX387125B (https=) |
| TW (1) | TWI746525B (https=) |
| WO (1) | WO2017153527A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020102198A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Heterocyclic derivatives as pi3k inhibitors |
| WO2020102150A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Heterocyclic derivatives as pi3k inhibitors |
| WO2020102216A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Substituted 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 |
| CN114206332B (zh) * | 2019-06-04 | 2024-08-23 | 艾库斯生物科学有限公司 | 2,3,5-三取代吡唑并[1,5-a]嘧啶化合物 |
| 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 |
| CN115611883B (zh) * | 2021-07-13 | 2025-03-28 | 生物岛实验室 | 一种双环结构的PI3Kα抑制剂及其制备方法和用途 |
| CN119768404A (zh) * | 2022-09-01 | 2025-04-04 | 上海海雁医药科技有限公司 | 杂芳基取代的吡啶并吡咯酮衍生物、其药物组合物及应用 |
| JP2025531798A (ja) * | 2022-09-09 | 2025-09-25 | 上海▲瑛▼黎薬業有限公司 | 含窒素複素環化合物、その医薬組成物および使用 |
| 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 |
| CN121816181A (zh) | 2023-06-30 | 2026-04-07 | 柏林合作研究学会 | 噻唑并四氢喹啉化合物作为ii类磷酸肌醇3-激酶抑制剂 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200613272A (en) * | 2004-08-13 | 2006-05-01 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
| WO2006089106A2 (en) * | 2005-02-17 | 2006-08-24 | Icos Corporation | Phosphoinositide 3-kinase inhibitors for inhibiting leukocyte accumulation |
| WO2007084391A2 (en) * | 2006-01-18 | 2007-07-26 | Amgen Inc. | Thiazole compounds as protein kinase b ( pkb) inhibitors |
| JP2009535386A (ja) * | 2006-05-03 | 2009-10-01 | アストラゼネカ アクチボラグ | チアゾール誘導体および抗腫瘍剤としてのその使用 |
| EP1894931A1 (en) * | 2006-08-30 | 2008-03-05 | Cellzome Ag | Triazole derivatives as kinase inhibitors |
| US20110230472A1 (en) * | 2008-08-29 | 2011-09-22 | Shionogi & Co., Ltd. | Ring-fused azole derivative having pi3k-inhibiting activity |
| MX2011008645A (es) * | 2009-02-17 | 2011-09-30 | Vertex Pharma | Inhibidores de tetrahidrotiazolopiridina de fosfatidilinositol 3 cinasa. |
| KR101758046B1 (ko) * | 2009-12-22 | 2017-07-14 | 버텍스 파마슈티칼스 인코포레이티드 | 포스파티딜이노시톨 3-키나제의 이소인돌리논 억제제 |
| CN104379573A (zh) * | 2012-04-20 | 2015-02-25 | 艾伯维公司 | 异吲哚酮衍生物 |
| SG11201602265PA (en) * | 2013-09-25 | 2016-04-28 | Vertex Pharma | A selective inhibitor of phosphatidylinositol 3-kinase-gamma |
| US9862711B2 (en) | 2014-04-24 | 2018-01-09 | Novartis Ag | Pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
| BR112016024484A2 (pt) | 2014-04-24 | 2017-08-15 | Novartis Ag | derivados de aminopiridina como inibidores de fosfatidilinositol 3-quinase |
| CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
-
2017
- 2017-03-09 EP EP17709681.5A patent/EP3426652B1/en active Active
- 2017-03-09 JP JP2018547461A patent/JP6893520B2/ja not_active Expired - Fee Related
- 2017-03-09 KR KR1020187028625A patent/KR20180117693A/ko not_active Abandoned
- 2017-03-09 AU AU2017229445A patent/AU2017229445B2/en not_active Ceased
- 2017-03-09 WO PCT/EP2017/055552 patent/WO2017153527A1/en not_active Ceased
- 2017-03-09 BR BR112018068075A patent/BR112018068075A2/pt not_active IP Right Cessation
- 2017-03-09 TW TW106107711A patent/TWI746525B/zh not_active IP Right Cessation
- 2017-03-09 US US16/082,880 patent/US10858355B2/en not_active Expired - Fee Related
- 2017-03-09 EA EA201891931A patent/EA036388B1/ru not_active IP Right Cessation
- 2017-03-09 CN CN201780014898.XA patent/CN108779110B/zh not_active Expired - Fee Related
- 2017-03-09 CA CA3015893A patent/CA3015893C/en active Active
- 2017-03-09 AR ARP170100589A patent/AR107840A1/es unknown
- 2017-03-09 MX MX2018010894A patent/MX387125B/es unknown
-
2020
- 2020-11-04 US US17/088,689 patent/US20210047312A1/en not_active Abandoned