JP2016502544A5 - - Google Patents
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- JP2016502544A5 JP2016502544A5 JP2015545510A JP2015545510A JP2016502544A5 JP 2016502544 A5 JP2016502544 A5 JP 2016502544A5 JP 2015545510 A JP2015545510 A JP 2015545510A JP 2015545510 A JP2015545510 A JP 2015545510A JP 2016502544 A5 JP2016502544 A5 JP 2016502544A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- independently
- arylalkyl
- alkyl
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims description 216
- 125000000217 alkyl group Chemical group 0.000 claims description 165
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 145
- 201000011510 cancer Diseases 0.000 claims description 122
- 206010028980 Neoplasm Diseases 0.000 claims description 120
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 120
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 98
- 125000001072 heteroaryl group Chemical group 0.000 claims description 98
- 125000003545 alkoxy group Chemical group 0.000 claims description 97
- 125000000623 heterocyclic group Chemical group 0.000 claims description 92
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 88
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 88
- 125000004104 aryloxy group Chemical group 0.000 claims description 88
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 88
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 88
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 88
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 84
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 82
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 76
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 72
- 125000003342 alkenyl group Chemical group 0.000 claims description 72
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 56
- 206010006187 Breast cancer Diseases 0.000 claims description 55
- 208000026310 Breast neoplasm Diseases 0.000 claims description 55
- 210000004027 cell Anatomy 0.000 claims description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 33
- 230000036210 malignancy Effects 0.000 claims description 29
- 125000004442 acylamino group Chemical group 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- -1 rather than the H Chemical compound 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 23
- 239000002246 antineoplastic agent Substances 0.000 claims description 20
- 229940127089 cytotoxic agent Drugs 0.000 claims description 20
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 19
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 18
- 208000029559 malignant endocrine neoplasm Diseases 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 206010009944 Colon cancer Diseases 0.000 claims description 13
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 13
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 13
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 13
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
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- 229960002438 carfilzomib Drugs 0.000 claims description 6
- BLMPQMFVWMYDKT-NZTKNTHTSA-N carfilzomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(C)OC1)NC(=O)CN1CCOCC1)CC1=CC=CC=C1 BLMPQMFVWMYDKT-NZTKNTHTSA-N 0.000 claims description 6
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- UVSMNLNDYGZFPF-UHFFFAOYSA-N pomalidomide Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UVSMNLNDYGZFPF-UHFFFAOYSA-N 0.000 claims description 6
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- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 5
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 4
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 4
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims description 4
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 4
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims description 4
- 102000009127 Glutaminase Human genes 0.000 claims description 4
- 108010073324 Glutaminase Proteins 0.000 claims description 4
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 4
- 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
- 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 4
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- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 4
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| US8604016B2 (en) | 2011-11-21 | 2013-12-10 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| US10793535B2 (en) | 2012-11-16 | 2020-10-06 | Calithera Biosciences, Inc. | Heterocyclic glutaminase inhibitors |
| KR20220013017A (ko) | 2014-01-06 | 2022-02-04 | 리젠 파마슈티컬스 소시에떼 아노님 | 신규한 글루타미나제 저해제 |
| WO2015138902A1 (en) * | 2014-03-14 | 2015-09-17 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| AU2015254943B2 (en) | 2014-04-30 | 2019-04-04 | Pfizer Inc. | Cycloalkyl-linked diheterocycle derivatives |
| GB201409624D0 (en) | 2014-05-30 | 2014-07-16 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| WO2015192014A1 (en) * | 2014-06-13 | 2015-12-17 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| JP6619758B2 (ja) | 2014-07-03 | 2019-12-11 | ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム | 疾患を処置するためのｇｌｓ１阻害薬 |
| US20160002204A1 (en) * | 2014-07-03 | 2016-01-07 | Board Of Regents, The University Of Texas System | Gls1 inhibitors for treating disease |
| US10660861B2 (en) | 2014-07-09 | 2020-05-26 | The Johns Hopkins University | Glutaminase inhibitor discovery and nanoparticle-enhanced delivery for cancer therapy |
| WO2016014890A1 (en) * | 2014-07-24 | 2016-01-28 | Calithera Biosciences, Inc. | Treatment of multiple myeloma with heterocyclic inhibitors of glutaminase |
| SG11201700816YA (en) | 2014-08-07 | 2017-02-27 | Calithera Biosciences Inc | Crystal forms of glutaminase inhibitors |
| US10245254B2 (en) | 2014-10-03 | 2019-04-02 | University of Pittsburgh—of the Commonwealth System of Higher Education | Glutaminase inhibitors |
| EA037152B1 (ru) * | 2015-03-30 | 2021-02-11 | Калитера Байосайенсиз, Инк. | Способ лечения рака |
| JP6944377B2 (ja) * | 2015-04-06 | 2021-10-06 | 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 | グルタミナーゼの阻害剤を用いる肺がんの処置 |
| CA2990457C (en) | 2015-06-30 | 2024-07-02 | Board Of Regents, University Of Texas System | PYRROLIDINYL AND PIPERIDINYL DERIVATIVES AND RELATED PHARMACEUTICAL COMPOSITIONS USEFUL AS GLS1 INHIBITORS |
| JP6971239B2 (ja) * | 2015-10-05 | 2021-11-24 | 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イムノオンコロジー薬剤との併用療法 |
| CN106890184B (zh) * | 2015-12-18 | 2019-06-25 | 诺言医药科技(上海)有限公司 | 抗肿瘤的谷氨酰胺酶抑制剂和肿瘤血管生成抑制剂药物组合物及其应用 |
| JP6976248B2 (ja) | 2015-12-22 | 2021-12-08 | ボード オブ リージェンツ、ザ ユニバーシテイ オブ テキサス システム | （ｒ）−１−（４−（６−（２−（４−（３，３−ジフルオロシクロブトキシ）−６−メチルピリジン−２−イル）アセトアミド）ピリダジン−３−イル）−２−フルオロブチル）−ｎ−メチル−１ｈ−１，２，３−トリアゾール−４−カルボキサミドの塩形態および多形体 |
| PT3423105T (pt) | 2016-03-02 | 2021-07-19 | Eisai R&D Man Co Ltd | Conjugados de anticorpo-fármaco à base de eribulina e métodos de utilização |
| CN107474024B (zh) * | 2016-06-08 | 2022-12-13 | 北京赛林泰医药技术有限公司 | 一种谷氨酰酶抑制剂及其组合物和用途 |
| MX2019002108A (es) | 2016-08-25 | 2019-07-08 | Calithera Biosciences Inc | Terapia de combinacion con inhibidores de glutaminasa. |
| US10195197B2 (en) | 2016-08-25 | 2019-02-05 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| US20180055825A1 (en) * | 2016-08-25 | 2018-03-01 | Yu Liang | Treatment of cancer with inhibitors of glutaminase |
| US10086987B2 (en) * | 2016-10-13 | 2018-10-02 | Altria Client Services Llc | Reseal label for box in a box re-sealable pack |
| CN107137401A (zh) * | 2017-03-28 | 2017-09-08 | 刘纪君 | 一种治疗产后抑郁症的药物组合物 |
| CN106860460B (zh) * | 2017-03-29 | 2019-04-23 | 上海市第一人民医院 | 谷氨酰胺酶抑制剂cb-839在制备治疗雌激素敏感型子宫内膜癌的药物中的应用 |
| CN111225903B (zh) | 2017-10-18 | 2024-08-16 | 德州大学系统董事会 | 谷氨酰胺酶抑制剂疗法 |
| CN110746416A (zh) * | 2019-09-05 | 2020-02-04 | 中国药科大学 | 含有三氮唑结构的谷氨酰胺酶gls1抑制剂或其可药用的盐、其制备方法及用途 |
| 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 |
| KR20230001587A (ko) * | 2021-06-28 | 2023-01-05 | 연세대학교 산학협력단 | 암의 예방 또는 치료용 약학 조성물 |
| CN114805346A (zh) * | 2021-07-08 | 2022-07-29 | 成都硕德药业有限公司 | 杂环类衍生物、其制备方法及用途 |
| KR102649592B1 (ko) * | 2021-08-18 | 2024-03-20 | 한국화학연구원 | 신규한 마크로사이클 화합물, 이의 제조방법, 이를 유효성분으로 포함하는 암 또는 자가면역질환의 예방 또는 치료용 약학적 조성물 |
| CN116023375A (zh) * | 2021-10-25 | 2023-04-28 | 成都苑东生物制药股份有限公司 | 一种杂环类衍生物、其制备方法及用途 |
| CN114057601B (zh) * | 2021-12-14 | 2024-11-08 | 重庆腾泽化学有限公司 | 一种丁二酸二酰肼的制备方法 |
| CN114805334B (zh) * | 2022-05-24 | 2023-06-09 | 深圳大学 | 一种QC和GSK-3β多靶向抑制剂及其制备方法与应用 |
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| US6451828B1 (en) * | 2000-08-10 | 2002-09-17 | Elan Pharmaceuticals, Inc. | Selective inhibition of glutaminase by bis-thiadiazoles |
| CA2578680C (en) * | 2004-04-15 | 2011-06-14 | University Of Florida Research Foundation, Inc. | Proteolytic markers as diagnostic biomarkers for cancer, organ injury and muscle rehabilitation/exercise overtraining |
| EP2255818B1 (en) * | 2008-02-19 | 2018-08-22 | Earnest Medicine Co., Ltd. | Oral or enteral composition useful for recovery of physical functions |
| US20130109643A1 (en) * | 2010-05-10 | 2013-05-02 | The Johns Hopkins University | Metabolic inhibitor against tumors having an idh mutation |
| WO2012006506A1 (en) * | 2010-07-09 | 2012-01-12 | Massachusetts Institute Of Technology | Metabolic gene, enzyme, and flux targets for cancer therapy |
| AU2012340866B2 (en) * | 2011-11-21 | 2017-03-16 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| US10793535B2 (en) * | 2012-11-16 | 2020-10-06 | Calithera Biosciences, Inc. | Heterocyclic glutaminase inhibitors |
| WO2014079011A1 (en) * | 2012-11-22 | 2014-05-30 | Agios Pharmaceuticals, Inc. | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
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