JP2011504510A5 - - Google Patents
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- JP2011504510A5 JP2011504510A5 JP2010535108A JP2010535108A JP2011504510A5 JP 2011504510 A5 JP2011504510 A5 JP 2011504510A5 JP 2010535108 A JP2010535108 A JP 2010535108A JP 2010535108 A JP2010535108 A JP 2010535108A JP 2011504510 A5 JP2011504510 A5 JP 2011504510A5
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- JP
- Japan
- Prior art keywords
- composition
- item
- acceptable salt
- compound
- cation
- 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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- 150000001768 cations Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 8
- -1 combretastatin compound Chemical class 0.000 claims description 8
- 206010061187 Haematopoietic neoplasm Diseases 0.000 claims description 7
- 201000005787 hematologic cancer Diseases 0.000 claims description 7
- LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 4
- GSOXMQLWUDQTNT-WAYWQWQTSA-N [3-methoxy-2-phosphonooxy-6-[(z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl] dihydrogen phosphate Chemical compound OP(=O)(O)OC1=C(OP(O)(O)=O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 GSOXMQLWUDQTNT-WAYWQWQTSA-N 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 229940127089 cytotoxic agent Drugs 0.000 claims description 3
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical group O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
- 229960001231 choline Drugs 0.000 claims description 2
- 229960004397 cyclophosphamide Drugs 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide 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](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 2
- 229960005420 etoposide Drugs 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 201000000050 myeloid neoplasm Diseases 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960003087 tioguanine Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 13
- 241000512259 Ascophyllum nodosum Species 0.000 claims 1
- 239000012829 chemotherapy agent Substances 0.000 claims 1
- 239000001177 diphosphate Substances 0.000 claims 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 1
- 235000011180 diphosphates Nutrition 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 238000000034 method Methods 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 125000004151 quinonyl group Chemical group 0.000 description 3
- 239000003642 reactive oxygen metabolite Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical group O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
- 206010066476 Haematological malignancy Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 208000019420 lymphoid neoplasm Diseases 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98978607P | 2007-11-21 | 2007-11-21 | |
| US60/989,786 | 2007-11-21 | ||
| PCT/US2008/084427 WO2009067706A1 (en) | 2007-11-21 | 2008-11-21 | Method for treating hematopoietic neoplasms |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011504510A JP2011504510A (ja) | 2011-02-10 |
| JP2011504510A5 true JP2011504510A5 (https=) | 2012-12-27 |
| JP5302328B2 JP5302328B2 (ja) | 2013-10-02 |
Family
ID=40667883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010535108A Expired - Fee Related JP5302328B2 (ja) | 2007-11-21 | 2008-11-21 | 造血性新生物を治療するための方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US20090264382A1 (https=) |
| EP (1) | EP2219451B1 (https=) |
| JP (1) | JP5302328B2 (https=) |
| AU (1) | AU2008326251B2 (https=) |
| CA (1) | CA2703283C (https=) |
| DK (1) | DK2219451T3 (https=) |
| ES (1) | ES2529434T3 (https=) |
| HR (1) | HRP20150040T1 (https=) |
| PL (1) | PL2219451T3 (https=) |
| PT (1) | PT2219451E (https=) |
| SI (1) | SI2219451T1 (https=) |
| WO (1) | WO2009067706A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1481249A1 (en) * | 2002-03-07 | 2004-12-01 | Cambridge University Technical Services Limited | Scd fingerprints |
| WO2009067706A1 (en) | 2007-11-21 | 2009-05-28 | Oxigene, Inc. | Method for treating hematopoietic neoplasms |
| US8987271B2 (en) | 2010-12-22 | 2015-03-24 | Eutropics Pharmaceuticals, Inc. | 2,2′-biphenazine compounds and methods useful for treating disease |
| CN104276960B (zh) * | 2014-09-26 | 2016-09-28 | 安徽省逸欣铭医药科技有限公司 | 盐酸他喷他多和塞来昔布共晶及其组合物和制备方法 |
| US11419934B2 (en) | 2015-08-18 | 2022-08-23 | Oncotelic Therapeutics, Inc. | Use of VDAS to enhance immunomodulating therapies against tumors |
| US11478445B2 (en) * | 2017-10-25 | 2022-10-25 | Bionomics Ltd. | Method for treating acute myeloid leukemia |
| CA3126163A1 (en) * | 2019-01-15 | 2020-07-23 | Ptc Therapeutics, Inc. | Method for treating an acute myeloid leukemia |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4996237A (en) | 1987-01-06 | 1991-02-26 | Arizona Board Of Regents | Combretastatin A-4 |
| CA1338645C (en) | 1987-01-06 | 1996-10-15 | George R. Pettit | Isolation, structural elucidation and synthesis of novel antineoplastic substances denominated "combretastatins" |
| US4940726A (en) | 1989-04-26 | 1990-07-10 | Arizona Board Of Regents | Cell growth inhibitory macrocyclic lactones denominated Combretastatin D-1 and Combretastatin D-2 |
| GB9106177D0 (en) | 1991-03-22 | 1991-05-08 | Aston Molecules Ltd | Substituted diphenylethylenes and analogues or derivatives thereof |
| US5430062A (en) | 1992-05-21 | 1995-07-04 | Research Corporation Technologies, Inc. | Stilbene derivatives as anticancer agents |
| US6908910B2 (en) | 1993-08-06 | 2005-06-21 | The Children's Medical Center Corporation | Estrogenic compounds as anti-mitotic agents |
| US5731353A (en) | 1993-09-08 | 1998-03-24 | Ajinomoto Co., Inc. | Stilbene derivatives and pharmaceutical compositions containing them |
| TW325458B (en) | 1993-09-08 | 1998-01-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions comprising the same for anti-cancer |
| US5561122A (en) * | 1994-12-22 | 1996-10-01 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Combretastatin A-4 prodrug |
| TW334418B (en) | 1995-03-07 | 1998-06-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions |
| EP1003498A4 (en) | 1997-03-26 | 2004-07-14 | Biosource Tech Inc | DIAYLETHER AND THEIR DERIVATIVES LIKE ANTI-CANCER COMPOUNDS |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| EP1045853B1 (en) | 1998-01-09 | 2010-08-04 | ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA acting for and on behalf of ARIZONA STATE UNIVERSITY | Synthesis of combretastatin a-4 prodrugs |
| WO1999034788A1 (en) | 1998-01-09 | 1999-07-15 | Arizona Board Of Regents, A Body Corporate, Acting On Behalf Of Arizona State University | Synthesis of phenstatin and prodrugs thereof |
| GB2334256A (en) | 1998-02-12 | 1999-08-18 | Univ Montfort | Hydroxylation activated prodrugs |
| US6433012B1 (en) | 1998-03-25 | 2002-08-13 | Large Scale Biology Corp. | Method for inhibiting inflammatory disease |
| JP2002507567A (ja) | 1998-03-25 | 2002-03-12 | ラージ スケール バイオロジー コーポレイション | 血管形成を阻害するための安息香酸誘導体 |
| WO1999051246A1 (en) | 1998-04-03 | 1999-10-14 | Ajinomoto Co., Inc. | Antitumor agents |
| WO2000006556A1 (en) | 1998-07-27 | 2000-02-10 | Abbott Laboratories | Substituted oxazolines as antiproliferative agents |
| AU2190700A (en) | 1998-12-17 | 2000-07-03 | Tularik Inc. | Tubulin-binding agents |
| GB9903404D0 (en) | 1999-02-16 | 1999-04-07 | Angiogene Pharm Ltd | Methods of treatment and compositions useful for the treatment of diseases involving angiogenesis |
| GB9903403D0 (en) | 1999-02-16 | 1999-04-07 | Angiogene Pharm Ltd | Substituted stilbene compounds with vascular damaging activity |
| WO2000048606A1 (en) | 1999-02-18 | 2000-08-24 | Oxigene, Inc. | Compositions and methods for use in targeting vascular destruction |
| CO5170498A1 (es) | 1999-05-28 | 2002-06-27 | Abbott Lab | Biaril sulfonamidas son utiles como inhibidores de proliferacion celular |
| US6201001B1 (en) | 1999-08-02 | 2001-03-13 | Abbott Laboratories | Imidazole antiproliferative agents |
| GB9918912D0 (en) | 1999-08-12 | 1999-10-13 | Angiogene Pharm Ltd | New stilbenes with vascular damaging activity |
| US6849656B1 (en) | 1999-09-17 | 2005-02-01 | Baylor University | Indole-containing and combretastatin-related anti-mitotic and anti-tubulin polymerization agents |
| CA2407967C (en) * | 2000-03-10 | 2010-10-05 | Baylor University | Tubulin binding ligands and corresponding prodrug constructs |
| GB0007401D0 (en) | 2000-03-27 | 2000-05-17 | Cancer Res Campaign Tech | Substituted chalcones as therapeeutic compounds |
| ATE527271T1 (de) | 2000-04-27 | 2011-10-15 | Univ Arizona | Prodrugs von combretastatin a-1 phosphat und combretastatin b-1 phosphat |
| WO2001081288A1 (en) | 2000-04-27 | 2001-11-01 | Arizona Board Of Regents, A Body Corporate Of The State Of Arizona, Acting For And On Behalf Of Arizona State University | Hydroxyphenstatin and the prodrugs thereof |
| US20040122083A1 (en) | 2000-05-09 | 2004-06-24 | Pettit George R | Antitubulin assembly and cell growth inhibitor denominated "dioxostatin" |
| AU2001261474B2 (en) * | 2000-05-15 | 2006-03-09 | Celgene Corporation | Compositions and methods for the treatment of cancer |
| AU2001258628A1 (en) | 2000-05-31 | 2001-12-11 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
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| EP1351912A2 (en) | 2000-12-21 | 2003-10-15 | Cancer Research Ventures Limited | Substituted stilbenes, their reactions and anticancer activity |
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| AU2002246827B2 (en) * | 2000-12-22 | 2008-02-21 | Bristol-Myers Squibb Company | Methods for modulating tumor growth and metastasis |
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| GB2377469B (en) | 2001-07-13 | 2005-07-06 | Prismo Ltd | Method and apparatus for laying a traffic calming surface |
| EP1438281A4 (en) | 2001-10-26 | 2006-04-26 | Oxigene Inc | FUNCTIONALIZED STILBENE DERIVATIVES USEFUL AS IMPROVED VASCULAR TARGETING AGENTS |
| GB0126889D0 (en) | 2001-11-08 | 2002-01-02 | Paterson Inst For Cancer Res | Compounds and their uses |
| US7105695B2 (en) | 2001-12-21 | 2006-09-12 | Arizona Board Of Regents, Acting For And On Behalf Of Arizona State University | Synthesis of combretastatin A-2 prodrugs |
| JP2005532280A (ja) | 2002-04-03 | 2005-10-27 | アストラゼネカ アクチボラグ | 化合物 |
| US7358236B1 (en) * | 2002-06-21 | 2008-04-15 | Oxigene, Inc. | Control of acute hypertension and cardiotoxicity in patients treated with vascular targeting agents |
| US20040024696A1 (en) | 2002-08-02 | 2004-02-05 | Federico Alves | System for automatically transferring funds |
| TW549690U (en) | 2002-11-13 | 2003-08-21 | Tekcon Electronics Corp | Electrical card connector |
| EP1601348A4 (en) | 2003-02-28 | 2008-12-10 | Oxigene Inc | Compositions and methods with improved therapeutic activity |
| ITRM20030355A1 (it) | 2003-07-18 | 2005-01-19 | Sigma Tau Ind Farmaceuti | Composti ad attivita' citotossica derivati della combretastatina. |
| ES2551086T3 (es) | 2005-06-14 | 2015-11-16 | Baylor University | Análogos de combretastatina con actividad de unión a tubulina |
| WO2009067706A1 (en) | 2007-11-21 | 2009-05-28 | Oxigene, Inc. | Method for treating hematopoietic neoplasms |
-
2008
- 2008-11-21 WO PCT/US2008/084427 patent/WO2009067706A1/en not_active Ceased
- 2008-11-21 US US12/276,064 patent/US20090264382A1/en not_active Abandoned
- 2008-11-21 JP JP2010535108A patent/JP5302328B2/ja not_active Expired - Fee Related
- 2008-11-21 HR HRP20150040AT patent/HRP20150040T1/hr unknown
- 2008-11-21 SI SI200831365T patent/SI2219451T1/sl unknown
- 2008-11-21 CA CA2703283A patent/CA2703283C/en not_active Expired - Fee Related
- 2008-11-21 PT PT88517545T patent/PT2219451E/pt unknown
- 2008-11-21 DK DK08851754.5T patent/DK2219451T3/en active
- 2008-11-21 US US12/276,197 patent/US20090192098A1/en not_active Abandoned
- 2008-11-21 ES ES08851754.5T patent/ES2529434T3/es active Active
- 2008-11-21 EP EP08851754.5A patent/EP2219451B1/en not_active Not-in-force
- 2008-11-21 PL PL08851754T patent/PL2219451T3/pl unknown
- 2008-11-21 AU AU2008326251A patent/AU2008326251B2/en not_active Ceased
-
2011
- 2011-11-28 US US13/305,612 patent/US9040500B2/en not_active Expired - Fee Related
-
2015
- 2015-05-14 US US14/712,537 patent/US20150246064A1/en not_active Abandoned
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