KR100850331B1 - 이온화 방사선 독성으로부터 세포 및 조직을 보호하는데 사용되는 약학적 조성물 - Google Patents
이온화 방사선 독성으로부터 세포 및 조직을 보호하는데 사용되는 약학적 조성물 Download PDFInfo
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- KR100850331B1 KR100850331B1 KR1020037011357A KR20037011357A KR100850331B1 KR 100850331 B1 KR100850331 B1 KR 100850331B1 KR 1020037011357 A KR1020037011357 A KR 1020037011357A KR 20037011357 A KR20037011357 A KR 20037011357A KR 100850331 B1 KR100850331 B1 KR 100850331B1
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| WO2003072062A2 (en) * | 2002-02-28 | 2003-09-04 | Temple University-Of The Commonwealth System Of Higher Education | Amino-substituted (e)-2,6-dialkoxystyryl 4-substituted benzylsulfones for treating proliferative disorders |
| US7161031B2 (en) * | 2002-02-28 | 2007-01-09 | Temple University - Of The Commonwealth System Of Higher Education | Amino-substituted sulfonanilides and derivatives thereof for treating proliferative disorders |
| AU2004289281C1 (en) * | 2003-11-14 | 2011-12-08 | Onconova Therapeutics, Inc. | Alpha, beta-Unsaturated sulfoxides for treating proliferative disorders |
| CA2546445A1 (en) * | 2003-11-26 | 2005-06-16 | Arqule, Inc. | Use of beta-lapachone for protecting against radiation injury |
| EP3138832A1 (en) | 2004-03-16 | 2017-03-08 | Temple University - Of The Commonwealth System of Higher Education | Substituted phenoxy- and phenylthio- derivatives for treating proliferative disorders |
| US8058313B2 (en) | 2004-06-24 | 2011-11-15 | Temple University—Of the Commonwealth System of Higher Education | Alpha, beta-unsaturated sulfones, sulfoxides, sulfonimides, sulfinimides, acylsulfonamides and acylsulfinamides and therapeutic uses thereof |
| ATE497768T1 (de) * | 2004-07-19 | 2011-02-15 | Onconova Therapeutics Inc | Formulierungen für die parenterale verabreichung von (e)-2,6-dialkoxystryryl 4-substituierten benzylsulfonen |
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| US20090306207A1 (en) * | 2005-01-05 | 2009-12-10 | Reddy M V Ramana | Treatment of Drug-Resistant Proliferative Disorders |
| SI1896401T1 (sl) * | 2005-02-25 | 2013-07-31 | Temple University - Of The Commonwealth System Of Higher Education | Sinteza nenasičenih sulfidov, sulfonov, sulfoksidov in sulfonamidov |
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| JP2007302640A (ja) * | 2006-05-15 | 2007-11-22 | Natl Inst Of Radiological Sciences | 抗放射線被ばく障害剤 |
| CA2659222C (en) * | 2006-07-28 | 2012-01-31 | Onconova Therapeutics, Inc. | Formulations of radioprotective .alpha., .beta. unsaturated aryl sulfones |
| WO2008027049A1 (en) | 2006-08-30 | 2008-03-06 | Temple University - Of The Commonwealth System Of Higher Education | Composition and methods for the treatment of myelodysplastic syndrome and acute myeloid leukemia |
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| US20100049284A1 (en) * | 2008-05-15 | 2010-02-25 | The Catholic University Of America | Use of heat to treat biological systems exposed to damaging radiation |
| CA2738925A1 (en) * | 2008-10-01 | 2010-04-08 | The University Of North Carolina At Chapel Hill | Hematopoietic protection against chemotherapeutic compounds using selective cyclin-dependent kinase 4/6 inhibitors |
| JP2012504645A (ja) * | 2008-10-01 | 2012-02-23 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | 健康な細胞に対する電離放射線の影響を低下させる又は防止するための医薬組成物 |
| US20110250184A1 (en) * | 2008-12-16 | 2011-10-13 | Onconova Therapeutics ,Inc. | Methods for determining efficacy of a therapeutic regimen against deleterious effects of cytotoxic agents in human |
| EP3718560A3 (en) | 2009-05-13 | 2020-12-09 | The University of North Carolina at Chapel Hill | Cyclin dependent kinase inhibitors and methods of use |
| JP5882296B2 (ja) * | 2010-03-24 | 2016-03-09 | オンコノバ・セラピューティックス・インコーポレーテッド | 創傷の予防及び治療のための組成物及び方法 |
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| GB201010359D0 (en) | 2010-06-21 | 2010-08-04 | Univ Nottingham | Compounds for treating proliferative disorders |
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| AU2013318206B2 (en) | 2012-09-20 | 2018-07-26 | Temple University - Of The Commonwealth System Of Higher Education | Substituted alkyl diaryl derivatives, methods of preparation and uses |
| CN105407723A (zh) | 2013-03-15 | 2016-03-16 | G1治疗公司 | 高效的抗赘生剂和抗增生剂 |
| WO2014144326A1 (en) | 2013-03-15 | 2014-09-18 | G1 Therapeutics, Inc. | Transient protection of normal cells during chemotherapy |
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| US10383831B2 (en) | 2015-08-03 | 2019-08-20 | Temple University—Of the Commonwealth System of Higher Education | 2,4,6-trialkoxystryl aryl sulfones, sulfonamides and carboxamides, and methods of preparation and use |
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| EP4001263B1 (en) * | 2019-07-18 | 2024-03-27 | Huaxiashengsheng Pharmaceutical Beijing Co., Ltd. | Carbamate-substituted styryl sulfone compound, preparation method, and application thereof |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6359013B1 (en) | 1997-10-03 | 2002-03-19 | Temple University-Of The Commonwealth System Of Higher Education | Styryl sulfone anticancer agents |
| US20020055530A1 (en) * | 2000-04-06 | 2002-05-09 | Neuberger Timothy J. | Compositions and methods for promoting tissue regeneration |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6201154B1 (en) * | 1999-03-31 | 2001-03-13 | Temple University-Of The Commonwealth Of Higher Education | Z-styryl sulfone anticancer agents |
| CA2366750C (en) * | 1999-04-02 | 2010-06-01 | Temple University - Of The Commonwealth System Of Higher Education | (e)-styryl sulfone anticancer agents |
| JP2002541101A (ja) * | 1999-04-02 | 2002-12-03 | テンプル・ユニバーシティ−オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション | スチリルスルホン抗癌剤 |
| WO2001026645A1 (en) * | 1999-10-12 | 2001-04-19 | Temple University-Of The Commonwealth System Of Higher Education | Method for protecting normal cells from cytotoxicity of chemotherapeutic agents |
| US6664287B2 (en) * | 2000-03-15 | 2003-12-16 | Bethesda Pharmaceuticals, Inc. | Antioxidants |
| US6486210B2 (en) | 2000-04-14 | 2002-11-26 | Temple University—Of the Commonwealth System of Higher Education | Substituted styryl benzylsulfones for treating proliferative disorders |
| ATE479657T1 (de) * | 2001-02-28 | 2010-09-15 | Univ Temple | N-(aryl)-2-arylethensulfonamide und ihre therapeutischen anwendungen |
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2002
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- 2002-02-28 CA CA2439288A patent/CA2439288C/en not_active Expired - Lifetime
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6359013B1 (en) | 1997-10-03 | 2002-03-19 | Temple University-Of The Commonwealth System Of Higher Education | Styryl sulfone anticancer agents |
| US20020055530A1 (en) * | 2000-04-06 | 2002-05-09 | Neuberger Timothy J. | Compositions and methods for promoting tissue regeneration |
Non-Patent Citations (1)
| Title |
|---|
| J. Org. Chem, 51, 5235-5240(1986.) |
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|---|---|
| EP1370253A4 (en) | 2005-08-17 |
| EP1370253A2 (en) | 2003-12-17 |
| CA2439288A1 (en) | 2002-09-12 |
| KR20030086596A (ko) | 2003-11-10 |
| IL157541A (en) | 2010-05-31 |
| EP1370253B1 (en) | 2008-09-03 |
| EP1370253B8 (en) | 2008-11-26 |
| ATE406881T1 (de) | 2008-09-15 |
| JP4302986B2 (ja) | 2009-07-29 |
| WO2002069892A3 (en) | 2002-11-07 |
| DE60228692D1 (de) | 2008-10-16 |
| US20030060505A1 (en) | 2003-03-27 |
| WO2002069892A2 (en) | 2002-09-12 |
| JP2004525908A (ja) | 2004-08-26 |
| CA2439288C (en) | 2011-08-09 |
| US6667346B2 (en) | 2003-12-23 |
| AU2002305942B2 (en) | 2006-10-26 |
| IL157541A0 (en) | 2004-03-28 |
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