JP2016505526A5 - - Google Patents
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- JP2016505526A5 JP2016505526A5 JP2015542813A JP2015542813A JP2016505526A5 JP 2016505526 A5 JP2016505526 A5 JP 2016505526A5 JP 2015542813 A JP2015542813 A JP 2015542813A JP 2015542813 A JP2015542813 A JP 2015542813A JP 2016505526 A5 JP2016505526 A5 JP 2016505526A5
- Authority
- JP
- Japan
- Prior art keywords
- cancer
- pharmaceutically acceptable
- substituted
- acceptable salt
- compound
- 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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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims description 29
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 28
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 28
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 28
- 125000004104 aryloxy group Chemical group 0.000 claims description 27
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 24
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 23
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- -1 rather than the H Chemical compound 0.000 claims description 12
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- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
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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 2
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- 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 1
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 1
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims 1
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 claims 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims 1
- 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 1
- 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 1
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 claims 1
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- 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 1
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| US8604016B2 (en) | 2011-11-21 | 2013-12-10 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| LT2920168T (lt) | 2012-11-16 | 2021-10-25 | Calithera Biosciences, Inc. | Heterociklinis gliutaminazės inhibitorius |
| KR20150091389A (ko) * | 2012-12-03 | 2015-08-10 | 칼리테라 바이오사이언시즈 인코포레이티드 | 글루타미나제의 헤테로사이클릭 억제제에 의한 암 치료 |
| CA2934700A1 (en) | 2014-01-06 | 2015-07-09 | Rhizen Pharmaceuticals Sa | Glutaminase inhibitors |
| DK3137460T3 (da) * | 2014-04-30 | 2019-12-16 | Pfizer | Cycloalkyl-bundne diheterocyklusderivater |
| GB201409624D0 (en) | 2014-05-30 | 2014-07-16 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| EP3154590B1 (en) | 2014-06-13 | 2021-04-14 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| EP3164195B1 (en) * | 2014-07-03 | 2022-06-15 | Board of Regents, The University of Texas System | Glutaminase inhibitor therapy |
| WO2016004413A2 (en) * | 2014-07-03 | 2016-01-07 | Board Of Regents, University Of Texas System | Gls1 inhibitors for treating disease |
| 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 |
| US10660861B2 (en) | 2014-07-09 | 2020-05-26 | The Johns Hopkins University | Glutaminase inhibitor discovery and nanoparticle-enhanced delivery for cancer therapy |
| EA037738B1 (ru) * | 2014-08-07 | 2021-05-17 | Калитера Байосайенсиз, Инк. | Кристаллические формы ингибиторов глутаминазы |
| EA037152B1 (ru) * | 2015-03-30 | 2021-02-11 | Калитера Байосайенсиз, Инк. | Способ лечения рака |
| EP3280415A4 (en) * | 2015-04-06 | 2018-12-26 | Calithera Biosciences Inc. | Treatment of lung cancer with inhibitors of glutaminase |
| ES2794868T3 (es) * | 2015-06-30 | 2020-11-19 | Univ Texas | Inhibidores de GLS1 para el tratamiento de enfermedades |
| CA3000996A1 (en) | 2015-10-05 | 2017-04-13 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors and immuno-oncology agents |
| US10323028B2 (en) * | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| US9938265B2 (en) * | 2015-11-30 | 2018-04-10 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| MX384732B (es) | 2015-12-22 | 2025-03-14 | Univ Texas | Formas de sales y polimorfos de (r)-1-(4-(6-(2-(4-(3,3-difluorociclobutoxi)-6-metilpiridin-2-il)acetamido)piridazin-3-il)-2-fluorobutil)-n-metil-1h-1,2,3-triazol-4-carboxamida. |
| WO2018039441A1 (en) * | 2016-08-25 | 2018-03-01 | Calithera Biosciences, Inc. | Combination therapy with glutaminase inhibitors |
| MX2019002108A (es) * | 2016-08-25 | 2019-07-08 | Calithera Biosciences Inc | Terapia de combinacion con inhibidores de glutaminasa. |
| WO2018039442A1 (en) * | 2016-08-25 | 2018-03-01 | Calithera Biosciences, Inc. | Treatment of cancer with inhibitors of glutaminase |
| WO2018228435A1 (zh) * | 2017-06-13 | 2018-12-20 | 南京明德新药研发股份有限公司 | 作为gls1抑制剂的化合物 |
| RU2020112558A (ru) | 2017-10-18 | 2021-11-18 | Боард Оф Регентс, Зе Юниверсити Оф Тексас Систем | Терапия на основе ингибитора глутаминазы |
| 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 |
| 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 |
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