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 (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2534131B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5461712B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR101456438B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102762535B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2011216176B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2788459C (cg-RX-API-DMAC7.html) |
| DK (1) | DK2534131T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2460040T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL221141A (cg-RX-API-DMAC7.html) |
| MX (1) | MX2012008989A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011100090A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070135380A1 (en) | 2005-08-12 | 2007-06-14 | Radiorx, Inc. | O-nitro compounds, pharmaceutical compositions thereof and uses thereof |
| US7507842B2 (en) | 2005-08-12 | 2009-03-24 | Radiorx, Inc. | Cyclic 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 |
| US20140308260A1 (en) | 2011-10-07 | 2014-10-16 | Radiorx, Inc. | Methods and compositions comprising a nitrite-reductase promoter for treatment of medical disorders and preservation of blood products |
| ES2935573T3 (es) | 2011-10-07 | 2023-03-08 | Epicentrx Inc | Compuestos de organonitro tioéter y usos médicos de estos |
| 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 |
| KR20190040931A (ko) | 2016-01-11 | 2019-04-19 | 에피센트알엑스, 인코포레이티드 | 2-브로모-1-(3,3-디니트로아제티딘-1-일)에타논의 정맥내 투여를 위한 조성물 및 방법 |
| EP3526195A4 (en) | 2016-10-14 | 2020-05-20 | EpicentRx, Inc. | SULFOXYALKYLE ORGANONITRO, RELATED COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR USE IN MEDICINE |
| IL271777B2 (en) | 2017-07-07 | 2024-09-01 | Epicentrx Inc | Compositions for parenteral administration of therapeutic agents |
| US11510901B2 (en) | 2018-01-08 | 2022-11-29 | Epicentrx, Inc. | Methods and compositions utilizing RRx-001 combination therapy for radioprotection |
| MX2023014676A (es) * | 2021-06-09 | 2024-02-06 | Epicentrx Inc | Composiciones de abdnaz cristalinas y metodos de elaboracion y uso de estas. |
| WO2024145484A1 (en) | 2022-12-29 | 2024-07-04 | Epicentrx, Inc. | Rrx-001 for treating reproductive-related disorders |
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| 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 |
| ES2092460T3 (es) | 1994-05-27 | 2001-02-01 | Cellegy Pharma Inc | Composicion dadora de oxido nitrico para el tratamiento de trastornos anales. |
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| 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 |
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| HRP20020808A2 (en) | 2000-04-10 | 2004-12-31 | Pfizer Prod Inc | Benzoamide piperidine containing compounds and related compounds |
| US6861530B2 (en) * | 2000-07-07 | 2005-03-01 | Kyowa Hakko Kogyo Co., Ltd. | Piperidine derivatives |
| 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 |
| AU2003247792B2 (en) * | 2002-07-03 | 2009-09-24 | Nicox S.A. | 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) |
| AU2004237574A1 (en) | 2003-03-13 | 2004-11-18 | Nitromed, Inc. | Nitrosated and nitrosylated compounds, compositions and methods of use |
| EP1646608B1 (en) | 2003-06-25 | 2011-03-02 | 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 |
| JP2008512490A (ja) * | 2004-09-08 | 2008-04-24 | チェルシー・セラピューティクス，インコーポレイテッド | 異常細胞増殖および炎症の障害を治療するための代謝的に不活性な葉酸拮抗剤 |
| 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 |
| BRPI0616755A2 (pt) * | 2005-09-27 | 2011-06-28 | Novartis Ag | compostos de carboxiamina e métodos de uso dos mesmos |
| KR100967848B1 (ko) * | 2008-05-28 | 2010-07-05 | 국방과학연구소 | 분자화약이 도입된, 고에너지 결합제용1-글리시딜-3,3-디니트로아제티딘 및 그의 제조방법 |
| WO2012078992A1 (en) * | 2010-12-09 | 2012-06-14 | Radiorx, Inc. | 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 CN CN201180008968.3A patent/CN102762535B/zh active Active
- 2011-01-18 WO PCT/US2011/021500 patent/WO2011100090A1/en not_active Ceased
- 2011-01-18 AU AU2011216176A patent/AU2011216176B2/en active Active
- 2011-01-18 CA CA2788459A patent/CA2788459C/en active Active
- 2011-01-18 KR KR1020127022598A patent/KR101456438B1/ko active Active
- 2011-01-18 ES ES11700989.4T patent/ES2460040T3/es active Active
- 2011-01-18 JP JP2012552884A patent/JP5461712B2/ja active Active
- 2011-01-18 MX MX2012008989A patent/MX2012008989A/es active IP Right Grant
- 2011-01-18 EP EP11700989.4A patent/EP2534131B1/en active Active
- 2011-01-18 DK DK11700989.4T patent/DK2534131T3/da active
-
2012
- 2012-07-26 IL IL221141A patent/IL221141A/en active IP Right Grant
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