MX369094B - Metodos para sintetizar un analogo de prostaciclina. - Google Patents
Metodos para sintetizar un analogo de prostaciclina.Info
- Publication number
- MX369094B MX369094B MX2015006972A MX2015006972A MX369094B MX 369094 B MX369094 B MX 369094B MX 2015006972 A MX2015006972 A MX 2015006972A MX 2015006972 A MX2015006972 A MX 2015006972A MX 369094 B MX369094 B MX 369094B
- Authority
- MX
- Mexico
- Prior art keywords
- processes
- present
- generate
- traditional methods
- methods
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 8
- 150000003815 prostacyclins Chemical class 0.000 title abstract 2
- 230000002194 synthesizing effect Effects 0.000 title 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000011210 chromatographic step Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 231100001231 less toxic Toxicity 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/44—Separation; Purification; Stabilisation; Use of additives by treatments giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La presente invención proporciona procesos para preparar un análogo de la prostaciclina de Fórmula I (ver Fórmula) o una de sus sales farmacéuticamente aceptables, donde R10 es un alquilo C1-6 lineal o ramificado. Los procesos de la presente invención comprenden pasos para generar rendimientos mejorados y menos subproductos que los métodos tradicionales. Los procesos de la presente invención emplean reactivos (p. ej., el reactivo oxidante) que son menos tóxicos que los que se emplean en los métodos tradicionales (p. ej., cloruro de oxalilo). Muchos de los procesos de la presente invención generan intermediarios con un e.e. y una pureza química mejorados; mediante los cuales se prescinde de pasos cromatográficos adicionales. Además, los procesos de la presente invención se pueden escalar para generar cantidades comerciales del compuesto final.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261734672P | 2012-12-07 | 2012-12-07 | |
| US201361777882P | 2013-03-12 | 2013-03-12 | |
| PCT/US2013/073474 WO2014089385A2 (en) | 2012-12-07 | 2013-12-06 | Methods of synthesizing a prostacyclin analog |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2015006972A MX2015006972A (es) | 2016-02-11 |
| MX369094B true MX369094B (es) | 2019-10-29 |
Family
ID=49881039
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2015006972A MX369094B (es) | 2012-12-07 | 2013-12-06 | Metodos para sintetizar un analogo de prostaciclina. |
| MX2019009102A MX2019009102A (es) | 2012-12-07 | 2015-06-02 | Metodos para sintetizar un analogo de prostaciclina. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2019009102A MX2019009102A (es) | 2012-12-07 | 2015-06-02 | Metodos para sintetizar un analogo de prostaciclina. |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US20150315114A1 (es) |
| EP (2) | EP3398931B1 (es) |
| JP (2) | JP6342414B2 (es) |
| KR (1) | KR20150091170A (es) |
| CN (3) | CN104837806A (es) |
| AU (2) | AU2013355130B2 (es) |
| BR (1) | BR112015013085A2 (es) |
| CA (1) | CA2893604A1 (es) |
| CL (1) | CL2015001535A1 (es) |
| DK (1) | DK2928858T3 (es) |
| EA (1) | EA034309B1 (es) |
| ES (1) | ES2664026T3 (es) |
| HK (1) | HK1212323A1 (es) |
| IL (1) | IL239172B (es) |
| MX (2) | MX369094B (es) |
| NZ (1) | NZ708130A (es) |
| PE (1) | PE20160090A1 (es) |
| PH (2) | PH12015501258A1 (es) |
| SG (2) | SG10201600303WA (es) |
| TW (1) | TWI634104B (es) |
| WO (1) | WO2014089385A2 (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG10201600303WA (en) * | 2012-12-07 | 2016-02-26 | Cayman Chemical Co Inc | Methods Of Synthesizing A Prostacyclin Analog |
| EP3712142B1 (en) | 2013-01-11 | 2022-07-06 | Corsair Pharma, Inc. | Prodrugs of treprostinil |
| US9505737B2 (en) | 2013-01-11 | 2016-11-29 | Corsair Pharma, Inc. | Treprostinil derivative compounds and methods of using same |
| EP3068752A1 (en) * | 2013-11-13 | 2016-09-21 | Cayman Chemical Company Incorporated | Amine salts of a prostacyclin analog |
| HU231186B1 (hu) | 2014-10-08 | 2021-06-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás treprostinil és sói előállítására |
| US9394227B1 (en) | 2015-06-17 | 2016-07-19 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| US9643911B2 (en) | 2015-06-17 | 2017-05-09 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| JP7220650B2 (ja) | 2016-09-26 | 2023-02-10 | ユナイテッド セラピューティクス コーポレイション | トレプロスチニルプロドラッグ |
| EP3498283A1 (en) | 2017-12-14 | 2019-06-19 | Ipsol AG | Glycosidic derivatives of treprostinil |
| HU231296B1 (hu) * | 2018-03-09 | 2022-09-28 | Chinoin Zrt | Eljárás treprostinil-dietanol-amin só B polimorf formájának előállítására |
| CA3149358A1 (en) | 2019-08-23 | 2021-03-04 | United Therapeutics Corporation | Treprostinil prodrugs |
| KR20230011929A (ko) | 2020-04-17 | 2023-01-25 | 유나이티드 쎄러퓨틱스 코포레이션 | 간질성 폐 질환의 치료에 사용하기 위한 트레프로스티닐 |
| CN116113415A (zh) | 2020-06-09 | 2023-05-12 | 联合治疗公司 | 曲前列尼尔的富马酰基二酮哌啶前药 |
| KR20220030006A (ko) | 2020-09-02 | 2022-03-10 | 바이오플러스 주식회사 | 미용 조성물을 포함하는 마스크 및 그 제조 방법 |
| WO2022132655A1 (en) | 2020-12-14 | 2022-06-23 | United Therapeutics Corporation | Methods of treating disease with treprostinil prodrugs |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4306075A (en) | 1980-03-28 | 1981-12-15 | The Upjohn Company | Composition and process |
| CA2039857A1 (en) * | 1990-04-26 | 1991-10-27 | Wilfred Po-Sum Shum | Process for producing epoxyalcohols of high optical purity |
| US6441245B1 (en) | 1997-10-24 | 2002-08-27 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| US6700025B2 (en) | 2001-01-05 | 2004-03-02 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| CN101780092B (zh) * | 2003-05-22 | 2012-07-04 | 联合治疗公司 | 化合物和释放前列环素类似物的方法 |
| EP2177526A4 (en) * | 2007-08-06 | 2012-08-22 | Taisho Pharmaceutical Co Ltd | 10A-AZALIDE COMPOUND CROSS-LINKED IN POSITION 10A AND POSITION 12 |
| ES2630407T3 (es) | 2007-12-17 | 2017-08-21 | United Therapeutics Corporation | Procedimiento mejorado para preparar treprostinil, el principio activo en Remodulin® |
| WO2010039531A1 (en) * | 2008-09-23 | 2010-04-08 | Resolvyx Pharmaceuticals, Inc. | Therapeutic compounds |
| CN101891596B (zh) * | 2009-05-22 | 2013-12-11 | 上海天伟生物制药有限公司 | 一种化合物及其制备方法和用途 |
| CN103261142B (zh) | 2010-06-03 | 2014-12-10 | 联合治疗公司 | 曲前列环素的制备 |
| CA2710726C (en) * | 2010-07-22 | 2016-02-23 | Alphora Research Inc. | Synthesis of treprostinil and intermediates useful therein |
| WO2012041334A1 (en) | 2010-10-01 | 2012-04-05 | Rigshospitalet | Compounds capable of modulating/preserving endothelial integrity for use in prevention or treatment of acute traumatic coagulopathy and resuscitated cardiac arrest |
| JP5199519B2 (ja) * | 2010-11-30 | 2013-05-15 | 独立行政法人科学技術振興機構 | ヌクレオシド類縁体又はその塩、オリゴヌクレオチド類縁体、遺伝子発現抑制剤、及び遺伝子検出用核酸プローブ |
| US8524939B2 (en) | 2011-08-24 | 2013-09-03 | Chirogate International Inc. | Intermediates for the synthesis of benzindene prostaglandins and preparations thereof |
| CN102796134B (zh) * | 2012-08-31 | 2015-07-01 | 甘肃皓天化学科技有限公司 | 一种马沙骨化醇中间体的制备方法 |
| SG10201600303WA (en) * | 2012-12-07 | 2016-02-26 | Cayman Chemical Co Inc | Methods Of Synthesizing A Prostacyclin Analog |
| EP3068752A1 (en) * | 2013-11-13 | 2016-09-21 | Cayman Chemical Company Incorporated | Amine salts of a prostacyclin analog |
-
2013
- 2013-12-06 SG SG10201600303WA patent/SG10201600303WA/en unknown
- 2013-12-06 CN CN201380064046.3A patent/CN104837806A/zh active Pending
- 2013-12-06 EA EA201591093A patent/EA034309B1/ru not_active IP Right Cessation
- 2013-12-06 MX MX2015006972A patent/MX369094B/es active IP Right Grant
- 2013-12-06 AU AU2013355130A patent/AU2013355130B2/en not_active Ceased
- 2013-12-06 JP JP2015545860A patent/JP6342414B2/ja not_active Expired - Fee Related
- 2013-12-06 BR BR112015013085A patent/BR112015013085A2/pt not_active Application Discontinuation
- 2013-12-06 CN CN201910784017.3A patent/CN110590547A/zh active Pending
- 2013-12-06 TW TW102144990A patent/TWI634104B/zh not_active IP Right Cessation
- 2013-12-06 CN CN201710389417.5A patent/CN107098925B/zh not_active Expired - Fee Related
- 2013-12-06 SG SG11201504430TA patent/SG11201504430TA/en unknown
- 2013-12-06 DK DK13812336.9T patent/DK2928858T3/en active
- 2013-12-06 KR KR1020157018095A patent/KR20150091170A/ko not_active Application Discontinuation
- 2013-12-06 WO PCT/US2013/073474 patent/WO2014089385A2/en active Application Filing
- 2013-12-06 EP EP18154039.4A patent/EP3398931B1/en active Active
- 2013-12-06 US US14/650,234 patent/US20150315114A1/en not_active Abandoned
- 2013-12-06 CA CA2893604A patent/CA2893604A1/en not_active Abandoned
- 2013-12-06 PE PE2015000742A patent/PE20160090A1/es unknown
- 2013-12-06 ES ES13812336.9T patent/ES2664026T3/es active Active
- 2013-12-06 NZ NZ708130A patent/NZ708130A/en not_active IP Right Cessation
- 2013-12-06 EP EP13812336.9A patent/EP2928858B1/en active Active
-
2015
- 2015-06-02 MX MX2019009102A patent/MX2019009102A/es unknown
- 2015-06-03 IL IL239172A patent/IL239172B/en not_active IP Right Cessation
- 2015-06-03 PH PH12015501258A patent/PH12015501258A1/en unknown
- 2015-06-05 CL CL2015001535A patent/CL2015001535A1/es unknown
-
2016
- 2016-01-08 HK HK16100175.9A patent/HK1212323A1/xx not_active IP Right Cessation
-
2017
- 2017-05-01 US US15/583,457 patent/US9908834B2/en not_active Expired - Fee Related
-
2018
- 2018-01-18 US US15/874,093 patent/US10450257B2/en not_active Expired - Fee Related
- 2018-03-15 PH PH12018500562A patent/PH12018500562A1/en unknown
- 2018-05-16 JP JP2018094605A patent/JP2018162250A/ja not_active Ceased
- 2018-09-21 AU AU2018233009A patent/AU2018233009B2/en not_active Expired - Fee Related
-
2019
- 2019-09-11 US US16/567,471 patent/US20200002261A1/en not_active Abandoned
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