JP2020510032A5 - - Google Patents
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- JP2020510032A5 JP2020510032A5 JP2019548731A JP2019548731A JP2020510032A5 JP 2020510032 A5 JP2020510032 A5 JP 2020510032A5 JP 2019548731 A JP2019548731 A JP 2019548731A JP 2019548731 A JP2019548731 A JP 2019548731A JP 2020510032 A5 JP2020510032 A5 JP 2020510032A5
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- JP
- Japan
- Prior art keywords
- cancer
- substituted
- composition according
- arylalkyl
- heteroarylalkyl
- 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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- 238000000034 method Methods 0.000 claims description 100
- 206010028980 Neoplasm Diseases 0.000 claims description 73
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 37
- -1 5-((4-ethylpiperazin-1-yl) methyl) pyridin-2-yl Chemical group 0.000 claims description 34
- 239000002246 antineoplastic agent Substances 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 201000011510 cancer Diseases 0.000 claims description 28
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 229940121727 Glutaminase inhibitor Drugs 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 23
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 22
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 22
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 22
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 21
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 20
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 13
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- 150000001875 compounds Chemical class 0.000 claims description 10
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- 150000003839 salts Chemical class 0.000 claims description 10
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
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- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 7
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- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
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- DUYJMQONPNNFPI-UHFFFAOYSA-N osimertinib Chemical group COC1=CC(N(C)CCN(C)C)=C(NC(=O)C=C)C=C1NC1=NC=CC(C=2C3=CC=CC=C3N(C)C=2)=N1 DUYJMQONPNNFPI-UHFFFAOYSA-N 0.000 claims description 6
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- 239000000126 substance Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
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- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims description 4
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- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
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- 229910052739 hydrogen Chemical group 0.000 claims description 4
- 239000001257 hydrogen Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
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- 208000032027 Essential Thrombocythemia Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
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- JLYAXFNOILIKPP-KXQOOQHDSA-N navitoclax Chemical group C([C@@H](NC1=CC=C(C=C1S(=O)(=O)C(F)(F)F)S(=O)(=O)NC(=O)C1=CC=C(C=C1)N1CCN(CC1)CC1=C(CCC(C1)(C)C)C=1C=CC(Cl)=CC=1)CSC=1C=CC=CC=1)CN1CCOCC1 JLYAXFNOILIKPP-KXQOOQHDSA-N 0.000 claims description 3
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- FAQDUNYVKQKNLD-UHFFFAOYSA-N olaparib Chemical group FC1=CC=C(CC2=C3[CH]C=CC=C3C(=O)N=N2)C=C1C(=O)N(CC1)CCN1C(=O)C1CC1 FAQDUNYVKQKNLD-UHFFFAOYSA-N 0.000 claims description 3
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- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 3
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 3
- CVCLJVVBHYOXDC-IAZSKANUSA-N (2z)-2-[(5z)-5-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-methoxypyrrol-2-ylidene]indole Chemical compound COC1=C\C(=C/2N=C3C=CC=CC3=C\2)N\C1=C/C=1NC(C)=CC=1C CVCLJVVBHYOXDC-IAZSKANUSA-N 0.000 claims description 2
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 claims description 2
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 claims description 2
- MWANBLRXAQSWIK-UHFFFAOYSA-N 1-[8-cyclopentyl-5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]-7H-pyrido[2,3-d]pyrimidin-6-yl]ethanone Chemical group C(C)(=O)C1=C(C2=C(N=C(N=C2)NC2=NC=C(C=C2)N2CCNCC2)N(C1)C1CCCC1)C MWANBLRXAQSWIK-UHFFFAOYSA-N 0.000 claims description 2
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- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims description 2
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- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 2
- RHXHGRAEPCAFML-UHFFFAOYSA-N 7-cyclopentyl-n,n-dimethyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=C2N(C3CCCC3)C(C(=O)N(C)C)=CC2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 RHXHGRAEPCAFML-UHFFFAOYSA-N 0.000 claims description 2
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- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 2
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| WO2014078645A1 (en) | 2012-11-16 | 2014-05-22 | Calithera Biosciences, Inc. | Heterocyclic glutaminase inhibitors |
| KR20170082494A (ko) | 2014-08-07 | 2017-07-14 | 칼리테라 바이오사이언시즈, 인코포레이티드 | 결정 형태의 글루타미나아제 억제제 |
| CN108601767A (zh) | 2015-10-05 | 2018-09-28 | 卡利泰拉生物科技公司 | 用谷氨酰胺酶抑制剂和免疫肿瘤学药剂的组合疗法 |
| MA51823A (fr) * | 2018-02-12 | 2021-05-19 | Astrazeneca Ab | Osimertinib destiné à être utilisé dans le traitement du cancer du poumon non à petites cellules |
| WO2020132184A1 (en) * | 2018-12-19 | 2020-06-25 | University Of Maryland, Baltimore | Asparaginase-induced glutamine depletion combined with bcl-2 inhibition for treatment of hematologic and solid cancers |
| EP3931564A4 (en) * | 2019-02-26 | 2023-04-26 | Cell Response, Inc. | Methods for treating map3k8 positive cancers |
| CN111166886B (zh) * | 2019-06-26 | 2022-03-22 | 百济神州(北京)生物科技有限公司 | 谷氨酰胺酶抑制剂和Dyrk1B抑制剂用于治疗实体瘤的用途 |
| CN110804643B (zh) * | 2019-10-29 | 2022-06-21 | 同济大学 | 一种体外评价卡介苗对中性粒细胞活性影响的方法 |
| CN112891353B (zh) * | 2019-12-04 | 2024-01-30 | 苏州亚盛药业有限公司 | 药物组合及其用途 |
| CN111514460B (zh) * | 2020-05-22 | 2021-12-14 | 西安交通大学 | 大气压冷等离子体在抑制谷氨酰胺酶活性方面的用途及酶抑制剂 |
| KR20220056730A (ko) * | 2020-10-28 | 2022-05-06 | 의료법인 성광의료재단 | Abt263을 유효성분으로 포함하는 디스크 질환 예방 및 치료용 조성물 |
| KR20230001587A (ko) * | 2021-06-28 | 2023-01-05 | 연세대학교 산학협력단 | 암의 예방 또는 치료용 약학 조성물 |
| CN114107494A (zh) * | 2021-09-30 | 2022-03-01 | 浙江大学 | 用于软骨肉瘤诊治的生物标记物及谷氨酰胺酶抑制剂在制备治疗软骨肉瘤药物中的应用 |
| US20250161351A1 (en) * | 2022-06-10 | 2025-05-22 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Cancer treatment by arsenic trioxide combination therapy |
| CN116287275B (zh) * | 2023-04-10 | 2024-04-05 | 广州市第一人民医院（广州消化疾病中心、广州医科大学附属市一人民医院、华南理工大学附属第二医院） | Ptgr1作为cdk4/6抑制剂与二甲双胍联合用药指导标志物的应用 |
| CN119454681A (zh) * | 2024-11-08 | 2025-02-18 | 北京润州生物科技有限公司 | 肾型谷氨酰胺酶抑制剂及其联合用药的用途 |
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| EP3116872A4 (en) * | 2014-03-14 | 2017-08-30 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| JP6798890B2 (ja) * | 2014-06-13 | 2020-12-09 | キャリセラ バイオサイエンシーズ， インコーポレイテッド | グルタミナーゼ阻害剤との併用療法 |
| AU2016246521B2 (en) * | 2015-04-06 | 2020-07-09 | Calithera Biosciences, Inc. | Treatment of lung cancer with inhibitors of glutaminase |
| WO2017021177A1 (en) * | 2015-08-04 | 2017-02-09 | Universitat De Barcelona | Pharmaceutical combinations for use in the treatment of cancer |
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