JP2016538281A5 - - Google Patents
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- JP2016538281A5 JP2016538281A5 JP2016530111A JP2016530111A JP2016538281A5 JP 2016538281 A5 JP2016538281 A5 JP 2016538281A5 JP 2016530111 A JP2016530111 A JP 2016530111A JP 2016530111 A JP2016530111 A JP 2016530111A JP 2016538281 A5 JP2016538281 A5 JP 2016538281A5
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- JP
- Japan
- Prior art keywords
- alkyl
- alkenyl
- alkynyl
- independently
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 201
- 125000003342 alkenyl group Chemical group 0.000 claims description 188
- 125000000304 alkynyl group Chemical group 0.000 claims description 143
- 150000001875 compounds Chemical class 0.000 claims description 105
- 238000000034 method Methods 0.000 claims description 91
- -1 alkynylheteroaryl Chemical group 0.000 claims description 55
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 51
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 44
- 206010028980 Neoplasm Diseases 0.000 claims description 37
- 201000011510 cancer Diseases 0.000 claims description 35
- 239000002246 antineoplastic agent Substances 0.000 claims description 32
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 210000004027 cell Anatomy 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 20
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- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 claims description 10
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 claims description 10
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- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims description 9
- 229960000640 dactinomycin Drugs 0.000 claims description 9
- 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 9
- 102100040018 Interferon alpha-2 Human genes 0.000 claims description 8
- 108010079944 Interferon-alpha2b Proteins 0.000 claims description 8
- 102000029749 Microtubule Human genes 0.000 claims description 8
- 108091022875 Microtubule Proteins 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 8
- 125000005217 alkenylheteroaryl group Chemical group 0.000 claims description 8
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 8
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 8
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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 7
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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 description 6
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims description 6
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 6
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- 239000012623 DNA damaging agent Substances 0.000 claims description 6
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- 208000017604 Hodgkin disease Diseases 0.000 claims description 6
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 6
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 6
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 6
- 206010061328 Ovarian epithelial cancer Diseases 0.000 claims description 6
- 206010060862 Prostate cancer Diseases 0.000 claims description 6
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- 229960002340 pentostatin Drugs 0.000 claims description 6
- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 claims description 6
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- 239000003053 toxin Substances 0.000 claims description 6
- 231100000765 toxin Toxicity 0.000 claims description 6
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 claims description 5
- HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 claims description 5
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 5
- XGQXULJHBWKUJY-LYIKAWCPSA-N (z)-but-2-enedioic acid;n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound OC(=O)\C=C/C(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C XGQXULJHBWKUJY-LYIKAWCPSA-N 0.000 claims description 5
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- 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 5
- RTQWWZBSTRGEAV-PKHIMPSTSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-[4-(methylcarbamoylamino)phenyl]propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound CNC(=O)NC1=CC=C(C[C@@H](CN(CC(C)N(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 RTQWWZBSTRGEAV-PKHIMPSTSA-N 0.000 claims description 5
- 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 5
- XAUDJQYHKZQPEU-KVQBGUIXSA-N 5-aza-2'-deoxycytidine Chemical compound O=C1N=C(N)N=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XAUDJQYHKZQPEU-KVQBGUIXSA-N 0.000 claims description 5
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| WO2010147612A1 (en) | 2009-06-18 | 2010-12-23 | Lixte Biotechnology, Inc. | Methods of modulating cell regulation by inhibiting p53 |
| CA2877167A1 (en) | 2012-06-29 | 2014-01-03 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of diabetes |
| CA2909160C (en) | 2013-04-09 | 2021-05-25 | Lixte Biotechnology, Inc. | Formulations of oxabicycloheptanes and oxabicycloheptenes |
| US10071094B2 (en) | 2014-07-24 | 2018-09-11 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Protein phosphatase 2A inhibitors for treating myelodysplastic syndromes |
| WO2016057931A1 (en) | 2014-10-10 | 2016-04-14 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| US9359373B1 (en) * | 2014-11-21 | 2016-06-07 | Taipei Veterans General Hospital | Lipophilic N-substituted norcantharimide derivatives and uses thereof |
| AU2016219853B2 (en) | 2015-02-19 | 2019-05-16 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of depressive and stress disorders |
| EP3736275B1 (en) * | 2015-05-15 | 2024-07-03 | Lixte Biotechnology, Inc. | Oxabicycloheptane prodrugs for use in treating cancer |
| CN106083877A (zh) * | 2016-06-21 | 2016-11-09 | 遵义医学院附属医院 | 不饱和去甲斑蝥素甲酯钡盐及其抗肿瘤应用 |
| CN106117236A (zh) * | 2016-06-21 | 2016-11-16 | 遵义医学院附属医院 | 不饱和去甲斑蝥素苄酯钡盐及其抗肿瘤应用 |
| JP7246309B2 (ja) | 2016-12-08 | 2023-03-27 | リクスト・バイオテクノロジー，インコーポレイテッド | 免疫応答を調節するためのオキサビシクロヘプタン |
| CA3208466A1 (en) * | 2021-01-19 | 2022-07-28 | Lixte Biotechnology, Inc. | Oxabicycloheptanes for treatment of small cell lung cancer |
| WO2024097784A2 (en) * | 2022-11-03 | 2024-05-10 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for treating refractory cancers |
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| US5206386A (en) * | 1991-03-20 | 1993-04-27 | Isp Investments Inc. | Controlled release N-substituted pyrrolidone esters and process for the use thereof |
| US7893096B2 (en) * | 2003-03-28 | 2011-02-22 | Novartis Vaccines And Diagnostics, Inc. | Use of small molecule compounds for immunopotentiation |
| US20080267947A1 (en) * | 2006-09-07 | 2008-10-30 | Cirrito Thomas P | Cancer therapy with cantharidin and cantharidin analogs |
| CN101662939B (zh) * | 2007-02-06 | 2015-11-25 | 利克斯特生物技术公司 | 氧杂双环庚烷和氧杂双环庚烯，它们的制备及用途 |
| WO2010014141A1 (en) * | 2008-08-01 | 2010-02-04 | Lixte Biotechnology, Inc. | Methods for regulating cell mitosis by inhibiting serine/threonine phosphatase |
| US8227473B2 (en) * | 2008-08-01 | 2012-07-24 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
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