BR112015013085A2 - métodos de síntese de um análogo de prostaciclina - Google Patents
métodos de síntese de um análogo de prostaciclinaInfo
- Publication number
- BR112015013085A2 BR112015013085A2 BR112015013085A BR112015013085A BR112015013085A2 BR 112015013085 A2 BR112015013085 A2 BR 112015013085A2 BR 112015013085 A BR112015013085 A BR 112015013085A BR 112015013085 A BR112015013085 A BR 112015013085A BR 112015013085 A2 BR112015013085 A2 BR 112015013085A2
- Authority
- BR
- Brazil
- Prior art keywords
- processes
- present
- generate
- methods
- traditional methods
- Prior art date
Links
- 150000003815 prostacyclins Chemical class 0.000 title abstract 2
- 238000001308 synthesis method Methods 0.000 title 1
- 238000000034 method Methods 0.000 abstract 8
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 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
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical class O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 abstract 1
- 229960001123 epoprostenol Drugs 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
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
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- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
resumo da patente de invenção para: métodos de síntese de um análogo de prostaciclina. a presente invenção proporciona processos de preparação de um análogo de prostaciclina da fórmula i ou um sal farmacêuticamente aceitável do mesmo, em que r10 é um alquila c1-6 linear ou ramificado. os processos da presente invenção compreendem etapas que geram melhores rendimentos e menor número de subprodutos do que os métodos tradicionais. os processos da presente invenção empregam reagentes (por exemplo, o reagente oxidante) que são menos tóxicos do que os usados nos métodos tradicionais (por exemplo, cloreto de oxalila). muitos dos processos da presente invenção geram intermediários com melhor e.e. e pureza química; eliminando, portanto, a necessidade de etapas de cromatografia adicionais. ademais, os processos da presente invenção são escaláveis para gerar quantidades comerciais do composto 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 (1)
Publication Number | Publication Date |
---|---|
BR112015013085A2 true BR112015013085A2 (pt) | 2017-07-11 |
Family
ID=49881039
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR112015013085A BR112015013085A2 (pt) | 2012-12-07 | 2013-12-06 | métodos de síntese de um análogo de prostaciclina |
Country Status (21)
Country | Link |
---|---|
US (4) | US20150315114A1 (pt) |
EP (2) | EP3398931B1 (pt) |
JP (2) | JP6342414B2 (pt) |
KR (1) | KR20150091170A (pt) |
CN (3) | CN110590547A (pt) |
AU (2) | AU2013355130B2 (pt) |
BR (1) | BR112015013085A2 (pt) |
CA (1) | CA2893604A1 (pt) |
CL (1) | CL2015001535A1 (pt) |
DK (1) | DK2928858T3 (pt) |
EA (1) | EA034309B1 (pt) |
ES (1) | ES2664026T3 (pt) |
HK (1) | HK1212323A1 (pt) |
IL (1) | IL239172B (pt) |
MX (2) | MX369094B (pt) |
NZ (1) | NZ708130A (pt) |
PE (1) | PE20160090A1 (pt) |
PH (2) | PH12015501258B1 (pt) |
SG (2) | SG10201600303WA (pt) |
TW (1) | TWI634104B (pt) |
WO (1) | WO2014089385A2 (pt) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110590547A (zh) * | 2012-12-07 | 2019-12-20 | 开曼化学股份有限公司 | 前列环素衍生物的合成方法 |
WO2014110491A1 (en) | 2013-01-11 | 2014-07-17 | Theratrophix Llc | 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 |
HU231184B1 (hu) | 2014-10-08 | 2021-07-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Treprostinil-nátrium-monohidrát és eljárás ennek 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 |
KR102541885B1 (ko) | 2016-09-26 | 2023-06-12 | 유나이티드 쎄러퓨틱스 코포레이션 | 트레프로스티닐 프로드럭 |
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 |
EP4017588A1 (en) | 2019-08-23 | 2022-06-29 | United Therapeutics Corporation | Treprostinil prodrugs |
IL296567A (en) | 2020-04-17 | 2022-11-01 | United Therapeutics Corp | Terfostinil for use in the treatment of interstitial lung disease |
WO2021252446A1 (en) | 2020-06-09 | 2021-12-16 | United Therapeutics Corporation | Fumaryl diketopiperidine prodrugs of treprostinil |
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 |
US11884640B2 (en) * | 2021-06-02 | 2024-01-30 | Chirogate International Inc. | Processes and intermediates for the preparations of benzoprostacyclin analogues and benzoprostacyclin analogues prepared therefrom |
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 |
EP2792353B1 (en) * | 2003-05-22 | 2018-02-28 | United Therapeutics Corporation | Polymorph of Treprostinil diethanolamine salt |
US8293715B2 (en) * | 2007-08-06 | 2012-10-23 | Taisho Pharmaceutical Co., Ltd. | 10a-Azalide compound crosslinked at 10a- and 12-positions |
KR20160048222A (ko) | 2007-12-17 | 2016-05-03 | 유나이티드 세러퓨틱스 코오포레이션 | 레모둘린?의 활성 성분인 트레프로스티닐의 개선된 제조 방법 |
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 |
WO2011153363A1 (en) * | 2010-06-03 | 2011-12-08 | United Therapeutics Corporation | Treprostinil production |
CA2710726C (en) | 2010-07-22 | 2016-02-23 | Alphora Research Inc. | Synthesis of treprostinil and intermediates useful therein |
CN103238070B (zh) | 2010-10-01 | 2016-06-29 | 丹麦国家医院 | 能够调节/保护内皮完整性的用于预防或治疗急性创伤性凝血病和心脏骤停复苏的化合物 |
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 |
CN110590547A (zh) * | 2012-12-07 | 2019-12-20 | 开曼化学股份有限公司 | 前列环素衍生物的合成方法 |
EP3068752A1 (en) * | 2013-11-13 | 2016-09-21 | Cayman Chemical Company Incorporated | Amine salts of a prostacyclin analog |
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2013
- 2013-12-06 CN CN201910784017.3A patent/CN110590547A/zh active Pending
- 2013-12-06 CN CN201380064046.3A patent/CN104837806A/zh active Pending
- 2013-12-06 WO PCT/US2013/073474 patent/WO2014089385A2/en active Application Filing
- 2013-12-06 BR BR112015013085A patent/BR112015013085A2/pt not_active Application Discontinuation
- 2013-12-06 ES ES13812336.9T patent/ES2664026T3/es active Active
- 2013-12-06 JP JP2015545860A patent/JP6342414B2/ja not_active Expired - Fee Related
- 2013-12-06 DK DK13812336.9T patent/DK2928858T3/en active
- 2013-12-06 SG SG10201600303WA patent/SG10201600303WA/en unknown
- 2013-12-06 EP EP18154039.4A patent/EP3398931B1/en active Active
- 2013-12-06 TW TW102144990A patent/TWI634104B/zh not_active IP Right Cessation
- 2013-12-06 AU AU2013355130A patent/AU2013355130B2/en not_active Ceased
- 2013-12-06 EA EA201591093A patent/EA034309B1/ru not_active IP Right Cessation
- 2013-12-06 KR KR1020157018095A patent/KR20150091170A/ko not_active Application Discontinuation
- 2013-12-06 PE PE2015000742A patent/PE20160090A1/es unknown
- 2013-12-06 NZ NZ708130A patent/NZ708130A/en not_active IP Right Cessation
- 2013-12-06 SG SG11201504430TA patent/SG11201504430TA/en unknown
- 2013-12-06 MX MX2015006972A patent/MX369094B/es active IP Right Grant
- 2013-12-06 EP EP13812336.9A patent/EP2928858B1/en active Active
- 2013-12-06 CN CN201710389417.5A patent/CN107098925B/zh not_active Expired - Fee Related
- 2013-12-06 US US14/650,234 patent/US20150315114A1/en not_active Abandoned
- 2013-12-06 CA CA2893604A patent/CA2893604A1/en not_active Abandoned
-
2015
- 2015-06-02 MX MX2019009102A patent/MX2019009102A/es unknown
- 2015-06-03 PH PH12015501258A patent/PH12015501258B1/en unknown
- 2015-06-03 IL IL239172A patent/IL239172B/en not_active IP Right Cessation
- 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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Legal Events
Date | Code | Title | Description |
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B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] |
Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS. |
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B07E | Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette] | ||
B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
B11B | Dismissal acc. art. 36, par 1 of ipl - no reply within 90 days to fullfil the necessary requirements |