JP2013518925A5 - - Google Patents
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- Publication number
- JP2013518925A5 JP2013518925A5 JP2012552884A JP2012552884A JP2013518925A5 JP 2013518925 A5 JP2013518925 A5 JP 2013518925A5 JP 2012552884 A JP2012552884 A JP 2012552884A JP 2012552884 A JP2012552884 A JP 2012552884A JP 2013518925 A5 JP2013518925 A5 JP 2013518925A5
- Authority
- JP
- Japan
- Prior art keywords
- abdnaz
- solvent
- dnaz
- dichloromethane
- reaction mixture
- 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
Links
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 24
- 239000002904 solvent Substances 0.000 claims 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 18
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 14
- 238000000034 method Methods 0.000 claims 14
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 claims 8
- 239000011541 reaction mixture Substances 0.000 claims 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- 239000008346 aqueous phase Substances 0.000 claims 6
- 239000012074 organic phase Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 239000000725 suspension Substances 0.000 claims 4
- YNVDAIOEJHCEQA-UHFFFAOYSA-N 1-tert-butyl-3,3-dinitroazetidine Chemical compound CC(C)(C)N1CC([N+]([O-])=O)([N+]([O-])=O)C1 YNVDAIOEJHCEQA-UHFFFAOYSA-N 0.000 claims 3
- JODKFOVZURLVTG-UHFFFAOYSA-N 2-bromo-1-(3,3-dinitroazetidin-1-yl)ethanone Chemical compound [O-][N+](=O)C1([N+]([O-])=O)CN(C(=O)CBr)C1 JODKFOVZURLVTG-UHFFFAOYSA-N 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 239000002274 desiccant Substances 0.000 claims 2
- 238000011084 recovery Methods 0.000 claims 2
- 239000011877 solvent mixture Substances 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/702,782 | 2010-02-09 | ||
| US12/702,782 US8471041B2 (en) | 2010-02-09 | 2010-02-09 | Methods of synthesizing and isolating N-(bromoacetyl)-3,3-dinitroazetidine and a composition including the same |
| PCT/US2011/021500 WO2011100090A1 (en) | 2010-02-09 | 2011-01-18 | Methods of synthesizing and isolating n-(bromoacetyl)-3,3-dinitroazetidine and a composition including the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013518925A JP2013518925A (ja) | 2013-05-23 |
| JP2013518925A5 true JP2013518925A5 (enExample) | 2013-08-29 |
| JP5461712B2 JP5461712B2 (ja) | 2014-04-02 |
Family
ID=43875262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012552884A Active JP5461712B2 (ja) | 2010-02-09 | 2011-01-18 | Ｎ−（ブロモアセチル）−３，３−ジニトロアゼチジンの合成及び単離法並びにそれを含む組成物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8471041B2 (enExample) |
| EP (1) | EP2534131B1 (enExample) |
| JP (1) | JP5461712B2 (enExample) |
| KR (1) | KR101456438B1 (enExample) |
| CN (1) | CN102762535B (enExample) |
| AU (1) | AU2011216176B2 (enExample) |
| CA (1) | CA2788459C (enExample) |
| DK (1) | DK2534131T3 (enExample) |
| ES (1) | ES2460040T3 (enExample) |
| IL (1) | IL221141A (enExample) |
| MX (1) | MX2012008989A (enExample) |
| WO (1) | WO2011100090A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7507842B2 (en) | 2005-08-12 | 2009-03-24 | Radiorx, Inc. | Cyclic nitro compounds, pharmaceutical compositions thereof and uses thereof |
| US20070135380A1 (en) | 2005-08-12 | 2007-06-14 | Radiorx, Inc. | O-nitro compounds, pharmaceutical compositions thereof and uses thereof |
| US8664247B2 (en) | 2011-08-26 | 2014-03-04 | Radiorx, Inc. | Acyclic organonitro compounds for use in treating cancer |
| EP2763667B1 (en) | 2011-10-07 | 2022-10-26 | EpicentRx, Inc. | Organonitro thioether compounds and medical uses thereof |
| WO2013052803A2 (en) | 2011-10-07 | 2013-04-11 | Radiorx, Inc. | Methods and compositions comprising a nitrite-reductase promoter for treatment of medical disorders and preservation of blood products |
| US10342778B1 (en) | 2015-10-20 | 2019-07-09 | Epicentrx, Inc. | Treatment of brain metastases using organonitro compound combination therapy |
| US9987270B1 (en) | 2015-10-29 | 2018-06-05 | Epicentrix, Inc. | Treatment of gliomas using organonitro compound combination therapy |
| AU2017207304B2 (en) | 2016-01-11 | 2022-05-26 | Epicentrx, Inc. | Compositions and methods for intravenous administration of 2-bromo-1-(3,3-dinitroazetidin-1-yl)ethanone |
| CA3040479A1 (en) | 2016-10-14 | 2018-04-19 | Epicentrx, Inc. | Sulfoxyalkyl organonitro and related compounds and pharmaceutical compositions for use in medicine |
| IL311727A (en) | 2017-07-07 | 2024-05-01 | Epicentrx Inc | Preparations for intravenous administration of medical substances |
| WO2019164593A2 (en) | 2018-01-08 | 2019-08-29 | Epicentrx, Inc. | Methods and compositions utilizing rrx-001 combination therapy for radioprotection |
| TW202313001A (zh) * | 2021-06-09 | 2023-04-01 | 美商埃皮辛特瑞科斯公司 | 結晶abdnaz組合物及其製造及使用方法 |
| WO2024145484A1 (en) | 2022-12-29 | 2024-07-04 | Epicentrx, Inc. | Rrx-001 for treating reproductive-related disorders |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US4935450A (en) | 1982-09-17 | 1990-06-19 | Therapeutical Systems Corporation | Cancer therapy system for effecting oncolysis of malignant neoplasms |
| JPS60116642A (ja) | 1983-11-29 | 1985-06-24 | Nippon Kayaku Co Ltd | ２−モノ−置換メチル−５，５−ジメチル−シクロ−２−ヘキセノン誘導体 |
| GB8504253D0 (en) | 1985-02-19 | 1985-03-20 | Ici Plc | Electrostatic spraying apparatus |
| GB8728418D0 (en) | 1987-12-04 | 1988-01-13 | Jenkins T C | Nitro-substituted aromatic/hetero-aromatic compounds for use in cancer treatment |
| DE3815221C2 (de) | 1988-05-04 | 1995-06-29 | Gradinger F Hermes Pharma | Verwendung einer Retinol- und/oder Retinsäureester enthaltenden pharmazeutischen Zubereitung zur Inhalation zur Einwirkung auf die Schleimhäute des Tracheo-Bronchialtraktes einschließlich der Lungenalveolen |
| US5693794A (en) | 1988-09-30 | 1997-12-02 | The United States Of America As Represented By The Secretary Of The Navy | Caged polynitramine compound |
| JP2659614B2 (ja) | 1990-11-13 | 1997-09-30 | 株式会社日立製作所 | 表示制御装置 |
| US5698155A (en) | 1991-05-31 | 1997-12-16 | Gs Technologies, Inc. | Method for the manufacture of pharmaceutical cellulose capsules |
| US5336784A (en) | 1993-06-07 | 1994-08-09 | The Regents Of The University Of California | Synthesis of 1,3,3-trinitroazetidine |
| JP3211892B2 (ja) | 1994-05-27 | 2001-09-25 | セイジィ ファーマスーティカルス インコーポレーテッド | 肛門疾患を治療する窒素酸化物供与体及び方法 |
| ATE186222T1 (de) | 1995-03-14 | 1999-11-15 | Siemens Ag | Ultraschallzerstäuber mit abnehmbarer präzisionsdosiereinheit |
| ES2177771T3 (es) | 1995-03-14 | 2002-12-16 | Siemens Ag | Dispositivo atomizador ultrasonico con unidad desmontable de dosificacion de precision. |
| AU5798996A (en) | 1995-05-15 | 1996-11-29 | Sachs, Michael C. | Adnaz, compositions and processes |
| US5580988A (en) | 1995-05-15 | 1996-12-03 | The United States Of America As Represented By The Secretary Of The Army | Substituted azetidines and processes of using them |
| US5898038A (en) | 1996-03-19 | 1999-04-27 | Board Of Regents, The University Of Texas System | Treatment of osteoporosis and metabolic bone disorders with nitric oxide substrate and/or donors |
| JP2001501159A (ja) | 1996-10-15 | 2001-01-30 | イーストマン ケミカル カンパニー | 爆薬配合物 |
| GB9720797D0 (en) | 1997-09-30 | 1997-12-03 | Rhodes John | Pharmaceutical composition for the treatment of inflammatory bowel disease and irritable bowel syndrome |
| US5954047A (en) | 1997-10-17 | 1999-09-21 | Systemic Pulmonary Development, Ltd. | Methods and apparatus for delivering aerosolized medication |
| US6056966A (en) | 1998-05-18 | 2000-05-02 | Baker Norton Pharmaceuticals, Inc. | Method and compositions for treating impotence |
| US7635722B1 (en) | 1998-07-27 | 2009-12-22 | Saint Jude Pharmaceuticals, Inc. | Chemical induced intracellular hyperthermia |
| US6448253B1 (en) | 1998-09-16 | 2002-09-10 | King Pharmaceuticals Research And Development, Inc. | Adenosine A3 receptor modulators |
| US6245799B1 (en) | 1999-11-08 | 2001-06-12 | American Home Products Corp | [(Indol-3-yl)-cycloalkyl]-3-substituted azetidines for the treatment of central nervous system disorders |
| ES2244599T3 (es) | 2000-04-10 | 2005-12-16 | Pfizer Products Inc. | Compuestos de benzamido-piperidina como antagonistas de la sustancia p. |
| JP2002069057A (ja) | 2000-07-07 | 2002-03-08 | Kyowa Hakko Kogyo Co Ltd | ピペリジン誘導体 |
| DE10111049A1 (de) | 2001-03-06 | 2002-09-12 | Beiersdorf Ag | Verwendung von Substanzen, die verhindern, daß die NO-Synthese des warmblütigen Organismus ihre Wirkung entfaltet, zur Herstellung von kosmetischen oder dermatologischen Zubereitungen, zur Prophylaxe und Behandlung von entzündlichen Hautzuständen und/oder zum Hautschutz bei empfindlich determinierter trockener Haut |
| EP1336602A1 (en) | 2002-02-13 | 2003-08-20 | Giovanni Scaramuzzino | Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases |
| CA2491127A1 (en) | 2002-07-03 | 2004-01-15 | Nitromed, Inc. | Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use |
| AU2003282534A1 (en) | 2002-10-07 | 2004-05-04 | Radiorx, Inc. | X-nitro compounds, pharmaceutical compositions thereof and uses therof |
| US6870061B2 (en) | 2003-01-10 | 2005-03-22 | Alliant Techsystems Inc. | Continuous process and system for production of glycidyl nitrate from glycerin, nitric acid and caustic and conversion of glycidyl nitrate to poly(glycidyl nitrate) |
| EP1603933A2 (en) | 2003-03-13 | 2005-12-14 | Nitromed, Inc. | Nitrosated and nitrosylated compounds, compositions and methods of use |
| WO2004113281A1 (en) | 2003-06-25 | 2004-12-29 | Je Il Pharmaceutical Co., Ltd. | Tricyclic derivatives or pharmaceutically acceptable salts thereof, their preparations and pharmaceutical compositions containing them |
| GB0326047D0 (en) | 2003-11-07 | 2003-12-10 | Univ Sheffield | Substance |
| US7829708B2 (en) | 2004-09-08 | 2010-11-09 | Chelsea Therapeutics, Inc. | Metabolically inert antifolates for treating disorders of abnormal cellular proliferation and inflammation |
| US7507842B2 (en) * | 2005-08-12 | 2009-03-24 | Radiorx, Inc. | Cyclic nitro compounds, pharmaceutical compositions thereof and uses thereof |
| US20070135380A1 (en) | 2005-08-12 | 2007-06-14 | Radiorx, Inc. | O-nitro compounds, pharmaceutical compositions thereof and uses thereof |
| WO2007038459A2 (en) | 2005-09-27 | 2007-04-05 | Novartis Ag | Carboxyamine compounds and their use in the treatment of hdac dependent diseases |
| KR100967848B1 (ko) * | 2008-05-28 | 2010-07-05 | 국방과학연구소 | 분자화약이 도입된, 고에너지 결합제용1-글리시딜-3,3-디니트로아제티딘 및 그의 제조방법 |
| US20120149678A1 (en) | 2010-12-09 | 2012-06-14 | Oronsky Bryan T | Organonitro Compounds for Use in Treating Non-Hodgkin's Lymphoma and Leukemia, and Methods Relating Thereto |
-
2010
- 2010-02-09 US US12/702,782 patent/US8471041B2/en active Active
-
2011
- 2011-01-18 KR KR1020127022598A patent/KR101456438B1/ko active Active
- 2011-01-18 AU AU2011216176A patent/AU2011216176B2/en active Active
- 2011-01-18 CN CN201180008968.3A patent/CN102762535B/zh active Active
- 2011-01-18 MX MX2012008989A patent/MX2012008989A/es active IP Right Grant
- 2011-01-18 WO PCT/US2011/021500 patent/WO2011100090A1/en not_active Ceased
- 2011-01-18 ES ES11700989.4T patent/ES2460040T3/es active Active
- 2011-01-18 CA CA2788459A patent/CA2788459C/en active Active
- 2011-01-18 EP EP11700989.4A patent/EP2534131B1/en active Active
- 2011-01-18 DK DK11700989.4T patent/DK2534131T3/da active
- 2011-01-18 JP JP2012552884A patent/JP5461712B2/ja active Active
-
2012
- 2012-07-26 IL IL221141A patent/IL221141A/en active IP Right Grant
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