NZ592686A - Process for the preparation of vorinostat from aniline, hydroxylamine and suberic acid starting materials - Google Patents
Process for the preparation of vorinostat from aniline, hydroxylamine and suberic acid starting materialsInfo
- Publication number
- NZ592686A NZ592686A NZ592686A NZ59268609A NZ592686A NZ 592686 A NZ592686 A NZ 592686A NZ 592686 A NZ592686 A NZ 592686A NZ 59268609 A NZ59268609 A NZ 59268609A NZ 592686 A NZ592686 A NZ 592686A
- Authority
- NZ
- New Zealand
- Prior art keywords
- hydroxylamine
- aniline
- vorinostat
- salt
- suberic acid
- Prior art date
Links
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title abstract 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 title abstract 6
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 title abstract 5
- 229960000237 vorinostat Drugs 0.000 title abstract 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000007858 starting material Substances 0.000 title 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 abstract 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 abstract 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 abstract 2
- YNBDVONJRSJFLP-UHFFFAOYSA-N 8-(hydroxyamino)-8-oxooctanoic acid Chemical compound ONC(=O)CCCCCCC(O)=O YNBDVONJRSJFLP-UHFFFAOYSA-N 0.000 abstract 2
- PAXDAFSGJPGLGR-UHFFFAOYSA-N 8-anilino-8-oxooctanoic acid Chemical compound OC(=O)CCCCCCC(=O)NC1=CC=CC=C1 PAXDAFSGJPGLGR-UHFFFAOYSA-N 0.000 abstract 2
- 239000007822 coupling agent Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1746KO2008 | 2008-10-15 | ||
| PCT/GB2009/051376 WO2010043904A2 (en) | 2008-10-15 | 2009-10-14 | Improved process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ592686A true NZ592686A (en) | 2012-12-21 |
Family
ID=41822438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ592686A NZ592686A (en) | 2008-10-15 | 2009-10-14 | Process for the preparation of vorinostat from aniline, hydroxylamine and suberic acid starting materials |
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 |
| AU2009321384A1 (en) | 2008-11-26 | 2011-06-23 | 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 |
| EP2322160A1 (en) | 2002-03-04 | 2011-05-18 | Merck HDAC Research, LLC | Methods of inducing terminal differentiation |
| PT1663194E (pt) | 2003-08-26 | 2010-07-06 | Merck Hdac Res Llc | Utilizaão de saha para o tratamento de mesotelioma |
| CN1870985B (zh) * | 2003-08-26 | 2011-11-30 | 默克Hdac研究有限责任公司 | 用hdac抑制剂治疗癌症的方法 |
| EP1541549A1 (en) | 2003-12-12 | 2005-06-15 | Exonhit Therapeutics S.A. | Tricyclic hydroxamate and benzaminde derivatives, compositions and methods |
| RU2354362C2 (ru) | 2005-05-20 | 2009-05-10 | Мерк Энд Ко., Инк. | Композиции субероиланилид-гидроксаминовой кислоты и способы их получения |
| TWI415603B (zh) * | 2005-05-20 | 2013-11-21 | Merck Sharp & Dohme | １，８－辛二醯基苯胺羥胺酸（ｓｕｂｅｒｏｙｌａｎｉｌｉｄｅ ｈｙｄｒｏｘａｍｉｃ ａｃｉｄ）之調配物及其製配方法 |
| JP2010504969A (ja) | 2006-09-28 | 2010-02-18 | メルク エンド カムパニー インコーポレーテッド | Ｓａｈａのアミン塩基塩及びその多形 |
| MX2009003405A (es) | 2006-09-28 | 2009-04-09 | Merck & Co Inc | Composiciones farmaceuticas de inhibidores de la histona desacetilasa y compuestos quelantes de metal, y complejos de quelato de metal-inhibidor de histona desacetilasa. |
| US20110041589A1 (en) | 2007-12-14 | 2011-02-24 | Generics [Uk] Limited | New hpcl method |
| WO2009098515A1 (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 |
| AU2009321384A1 (en) | 2008-11-26 | 2011-06-23 | Generics [Uk] Limited | Polymorphs |
| US20110269838A1 (en) | 2008-11-26 | 2011-11-03 | Vinayak Gore | Novel processes and pure polymorphs |
-
2009
- 2009-10-14 AU AU2009305214A patent/AU2009305214B2/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
- 2009-10-14 EP EP09748455A patent/EP2349985A2/en not_active Withdrawn
- 2009-10-14 JP JP2011531571A patent/JP5769627B2/ja not_active Expired - Fee Related
- 2009-10-14 WO PCT/GB2009/051376 patent/WO2010043904A2/en not_active Ceased
- 2009-10-14 CN CN200980150218.2A patent/CN102264694B/zh not_active Expired - Fee Related
- 2009-10-14 US US13/124,337 patent/US8883851B2/en active Active
-
2014
- 2014-10-06 US US14/506,741 patent/US9162974B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012505872A (ja) | 2012-03-08 |
| US9162974B2 (en) | 2015-10-20 |
| WO2010043904A3 (en) | 2010-09-16 |
| AU2009305214A1 (en) | 2010-04-22 |
| CN102264694A (zh) | 2011-11-30 |
| US20150018424A1 (en) | 2015-01-15 |
| CN102264694B (zh) | 2015-11-25 |
| EP2349985A2 (en) | 2011-08-03 |
| US20110263712A1 (en) | 2011-10-27 |
| JP5769627B2 (ja) | 2015-08-26 |
| CA2740559A1 (en) | 2010-04-22 |
| CA2740559C (en) | 2016-02-16 |
| WO2010043904A2 (en) | 2010-04-22 |
| US8883851B2 (en) | 2014-11-11 |
| AU2009305214B2 (en) | 2015-06-25 |
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