JP2012505872A5 - - Google Patents
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- Publication number
- JP2012505872A5 JP2012505872A5 JP2011531571A JP2011531571A JP2012505872A5 JP 2012505872 A5 JP2012505872 A5 JP 2012505872A5 JP 2011531571 A JP2011531571 A JP 2011531571A JP 2011531571 A JP2011531571 A JP 2011531571A JP 2012505872 A5 JP2012505872 A5 JP 2012505872A5
- Authority
- JP
- Japan
- Prior art keywords
- coupling agent
- cdi
- dcc
- molar equivalents
- organic solvent
- 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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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 32
- PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 26
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 24
- 239000007822 coupling agent Substances 0.000 claims 24
- 239000000203 mixture Substances 0.000 claims 20
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 16
- 239000003960 organic solvent Substances 0.000 claims 13
- 238000000034 method Methods 0.000 claims 12
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims 12
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims 8
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 claims 8
- 229960000237 vorinostat Drugs 0.000 claims 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 6
- 239000012190 activator Substances 0.000 claims 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 claims 4
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 claims 4
- 201000005962 mycosis fungoides Diseases 0.000 claims 4
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 claims 4
- YNBDVONJRSJFLP-UHFFFAOYSA-N 8-(hydroxyamino)-8-oxooctanoic acid Chemical compound ONC(=O)CCCCCCC(O)=O YNBDVONJRSJFLP-UHFFFAOYSA-N 0.000 claims 3
- PAXDAFSGJPGLGR-UHFFFAOYSA-N 8-anilino-8-oxooctanoic acid Chemical compound OC(=O)CCCCCCC(=O)NC1=CC=CC=C1 PAXDAFSGJPGLGR-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical group ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims 2
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 201000000849 skin cancer Diseases 0.000 claims 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1746KO2008 | 2008-10-15 | ||
| IN1746/KOL/2008 | 2008-10-15 | ||
| PCT/GB2009/051376 WO2010043904A2 (en) | 2008-10-15 | 2009-10-14 | Improved process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012505872A JP2012505872A (ja) | 2012-03-08 |
| JP2012505872A5 true JP2012505872A5 (enExample) | 2012-11-29 |
| JP5769627B2 JP5769627B2 (ja) | 2015-08-26 |
Family
ID=41822438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011531571A Expired - Fee Related JP5769627B2 (ja) | 2008-10-15 | 2009-10-14 | ボリノスタットの調製方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8883851B2 (enExample) |
| EP (1) | EP2349985A2 (enExample) |
| JP (1) | JP5769627B2 (enExample) |
| CN (1) | CN102264694B (enExample) |
| AU (1) | AU2009305214B2 (enExample) |
| CA (1) | CA2740559C (enExample) |
| NZ (1) | NZ592686A (enExample) |
| WO (1) | WO2010043904A2 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1391812B1 (it) * | 2008-07-29 | 2012-01-27 | Maria Grazia Rimoli | Profarmaco galattosilato del ketorolac ad uso analgesico e antinfiammatorio con migliori caratteristiche farmacocinetiche e profilo tossicologico del farmaco di partenza |
| EP2362869A2 (en) * | 2008-11-26 | 2011-09-07 | Generics [UK] Limited | Polymorphs |
| WO2011061545A1 (en) | 2009-11-23 | 2011-05-26 | Generics [Uk] Limited | Hplc method for analyzing vorinostat |
| US20110313044A1 (en) * | 2010-06-18 | 2011-12-22 | Urquima S.A. | Polymorphs of Suberoylanilide Hydroxamic Acid |
| CN103018346A (zh) * | 2011-09-20 | 2013-04-03 | 北京本草天源药物研究院 | 伏立诺他及其药物组合物中的杂质的高效液相色谱分析方法 |
| CN104693071A (zh) * | 2013-12-04 | 2015-06-10 | 山东新时代药业有限公司 | 一种n- 羟基-n’- 苯基辛二酰胺制备方法 |
| CN103922967B (zh) * | 2014-04-15 | 2016-06-01 | 北京化工大学 | 一种异羟肟酸类化合物及其在制备抑制癌细胞增殖和/或治疗癌症的药物中的应用 |
| CN104292133B (zh) * | 2014-09-29 | 2016-06-01 | 烟台市华文欣欣医药科技有限公司 | 一种抗癌药物伏立诺他的合成方法 |
| CN104649925A (zh) * | 2015-02-13 | 2015-05-27 | 山东新时代药业有限公司 | 一种伏立诺他中间体的制备方法 |
| CN105259261A (zh) * | 2015-10-09 | 2016-01-20 | 扬子江药业集团江苏海慈生物药业有限公司 | 一种药物中苯胺含量的测定方法 |
| CN106008267B (zh) * | 2016-06-27 | 2018-04-06 | 马腾 | 一种抗癌药物伏立诺他的制备方法 |
| CN106187818B (zh) * | 2016-06-27 | 2017-12-08 | 刘美新 | 一种制备抗癌药物伏立诺他的方法 |
| US11554123B2 (en) * | 2017-03-01 | 2023-01-17 | Saint Joseph's University | Compositions and methods for reactivating latent HIV-1 infections |
| TWI650139B (zh) | 2017-10-11 | 2019-02-11 | 行政院原子能委員會核能硏究所 | 含有放射性同位素氟的異羥肟酸類造影劑、其製備方法及其用途 |
| CN109134313B (zh) * | 2018-10-16 | 2021-05-25 | 新昌县勤勉生物医药科技有限公司 | 一种利用改性介孔材料催化制备伏立诺他的方法 |
| CN110283102B (zh) * | 2019-05-31 | 2022-09-27 | 宿州亿帆药业有限公司 | 一种伏林司他ⅰ晶型的制备方法 |
| CN113943232A (zh) * | 2021-11-25 | 2022-01-18 | 汤斌 | 一种从大鲵肽中提取伏立诺他的方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5369108A (en) | 1991-10-04 | 1994-11-29 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and methods of use thereof |
| GB9504084D0 (en) * | 1995-03-01 | 1995-04-19 | British Biotech Pharm | Synthesis of carboxylic and hydroxamic acid derivatives |
| IT1283637B1 (it) * | 1996-05-14 | 1998-04-23 | Italfarmaco Spa | Composti ad attivita' antinfiammatoria ed immunosoppressiva |
| US6497820B1 (en) | 1998-02-03 | 2002-12-24 | Arqule, Inc. | Rapid method for separation of small molecules using reverse phase high performance liquid chromatography |
| US6541661B1 (en) * | 1999-11-23 | 2003-04-01 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US7456219B2 (en) * | 2002-03-04 | 2008-11-25 | Merck Hdac Research, Llc | Polymorphs of suberoylanilide hydroxamic acid |
| MXPA04008577A (es) | 2002-03-04 | 2005-07-13 | Aton Pharma Inc | Metodos para inducir diferenciacion terminal. |
| UA83065C2 (ru) * | 2003-08-26 | 2008-06-10 | МЕРК ЕйчДиЕйСи РІСЕРЧ, ЛЛС | Способ лечения мезотелиомы с использованием ингибитора hdac - субероиланилидгидроксаминовой кислоты (saha) |
| EP2201947A3 (en) | 2003-08-26 | 2010-08-11 | Merck HDAC Research, LLC | Use of SAHA for treating mesothelioma |
| EP1541549A1 (en) | 2003-12-12 | 2005-06-15 | Exonhit Therapeutics S.A. | Tricyclic hydroxamate and benzaminde derivatives, compositions and methods |
| UA93355C2 (ru) | 2005-05-20 | 2011-02-10 | Mepk Шарп Энд Доме Корп. | Композиция субероиланилид-гидроксаминовой кислоты и способы ee получения |
| TWI365068B (en) | 2005-05-20 | 2012-06-01 | Merck Sharp & Dohme | Formulations of suberoylanilide hydroxamic acid and methods for producing same |
| EP2079304A4 (en) | 2006-09-28 | 2010-01-06 | Merck & Co Inc | AMINBASE SALTS FROM SAHA AND POLYMORPHE DAVON |
| AU2007300532A1 (en) | 2006-09-28 | 2008-04-03 | Merck Sharp & Dohme Corp. | Pharmaceutical compositions of HDAC inhibitors and chelatable metal compounds, and metal-HDAC inhibitor chelate complexes |
| AU2008337304A1 (en) | 2007-12-14 | 2009-06-25 | Generics [Uk] Limited | HPLC method for analysing clopidogrel |
| AU2009211157A1 (en) * | 2008-02-07 | 2009-08-13 | Generics [Uk] Limited | Novel process for the preparation of vorinostat |
| US20090223286A1 (en) | 2008-02-13 | 2009-09-10 | Vandana Singh | Analytical method for determination of related substances of imipenem and cilastatin |
| CZ2008167A3 (cs) | 2008-03-14 | 2010-02-24 | Zentiva, A. S. | Specifické necistoty montelukastu |
| EP2362869A2 (en) | 2008-11-26 | 2011-09-07 | Generics [UK] Limited | Polymorphs |
| CA2744458A1 (en) | 2008-11-26 | 2010-06-03 | Generics [Uk] Limited | Novel processes and pure polymorphs |
-
2009
- 2009-10-14 AU AU2009305214A patent/AU2009305214B2/en not_active Ceased
- 2009-10-14 US US13/124,337 patent/US8883851B2/en active Active
- 2009-10-14 JP JP2011531571A patent/JP5769627B2/ja not_active Expired - Fee Related
- 2009-10-14 CN CN200980150218.2A patent/CN102264694B/zh not_active Expired - Fee Related
- 2009-10-14 EP EP09748455A patent/EP2349985A2/en not_active Withdrawn
- 2009-10-14 WO PCT/GB2009/051376 patent/WO2010043904A2/en not_active Ceased
- 2009-10-14 NZ NZ592686A patent/NZ592686A/xx not_active IP Right Cessation
- 2009-10-14 CA CA2740559A patent/CA2740559C/en not_active Expired - Fee Related
-
2014
- 2014-10-06 US US14/506,741 patent/US9162974B2/en active Active