JP6866043B2 - トレプロスチニルプロドラッグおよびトレプロスチニル誘導体プロドラッグの製造方法 - Google Patents

トレプロスチニルプロドラッグおよびトレプロスチニル誘導体プロドラッグの製造方法 Download PDF

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JP6866043B2
JP6866043B2 JP2017526523A JP2017526523A JP6866043B2 JP 6866043 B2 JP6866043 B2 JP 6866043B2 JP 2017526523 A JP2017526523 A JP 2017526523A JP 2017526523 A JP2017526523 A JP 2017526523A JP 6866043 B2 JP6866043 B2 JP 6866043B2
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acid
linear
branched
formula
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JP2017535555A (ja
JP2017535555A5 (enExample
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マリニン，ウラジミール
パーキンス，ウォルター
ライファー，フランツィスカ
エム． コニーチェク，ドナ
エム． コニーチェク，ドナ
リ，ジーリー
プラウント，アダム
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Insmed Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
JP2017526523A 2014-11-18 2015-11-18 トレプロスチニルプロドラッグおよびトレプロスチニル誘導体プロドラッグの製造方法 Active JP6866043B2 (ja)

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US201462081515P 2014-11-18 2014-11-18
US62/081,515 2014-11-18
PCT/US2015/061427 WO2016081658A1 (en) 2014-11-18 2015-11-18 Methods of manufacturing treprostinil and treprostinil derivative prodrugs

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JP2017535555A JP2017535555A (ja) 2017-11-30
JP2017535555A5 JP2017535555A5 (enExample) 2018-12-27
JP6866043B2 true JP6866043B2 (ja) 2021-04-28

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US (5) US10343979B2 (enExample)
EP (2) EP3904326A1 (enExample)
JP (1) JP6866043B2 (enExample)
AU (1) AU2015349969B2 (enExample)
CA (1) CA2967385C (enExample)
ES (1) ES2873873T3 (enExample)
WO (1) WO2016081658A1 (enExample)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9505737B2 (en) 2013-01-11 2016-11-29 Corsair Pharma, Inc. Treprostinil derivative compounds and methods of using same
ES2927844T3 (es) 2013-01-11 2022-11-11 Corsair Pharma Inc Profármacos de treprostinil
SI3060041T1 (sl) 2013-10-25 2021-04-30 Insmed Incorporated Spojine prostaciklina
EP3904326A1 (en) 2014-11-18 2021-11-03 Insmed Incorporated Methods of manufacturing treprostinil and treprostinil derivative prodrugs
US9643911B2 (en) 2015-06-17 2017-05-09 Corsair Pharma, Inc. Treprostinil derivatives and compositions and uses thereof
US9394227B1 (en) 2015-06-17 2016-07-19 Corsair Pharma, Inc. Treprostinil derivatives and compositions and uses thereof
WO2017223400A1 (en) * 2016-06-24 2017-12-28 Insmed Incorporated Prostacyclin compounds and compositions for treating sarcoidosis
CA3038276A1 (en) * 2016-09-26 2018-03-29 United Therapeutics Corporation Treprostinil prodrugs
CN114072136B (zh) 2019-04-29 2024-11-29 英斯梅德股份有限公司 曲前列素前药的干粉组合物及其使用方法
WO2021041320A1 (en) 2019-08-23 2021-03-04 United Therapeutics Corporation Treprostinil prodrugs
US10781160B1 (en) * 2019-10-04 2020-09-22 Chirogate International Inc. Hexadecyl Treprostinil crystals and methods for preparation thereof
IL296567A (en) 2020-04-17 2022-11-01 United Therapeutics Corp Terfostinil for use in the treatment of interstitial lung disease
US11793780B2 (en) 2020-06-09 2023-10-24 United Therapeutics Corporation Prodrugs of treprosiinil
KR20250133451A (ko) 2020-12-14 2025-09-05 유나이티드 쎄러퓨틱스 코포레이션 트레프로스티닐 프로드러그로 질환을 치료하는 방법
AU2022229367A1 (en) 2021-03-03 2023-09-14 United Therapeutics Corporation A dry powder composition of trestinil and its prodrug thereof and further comprising comprising (e)-3,6-bis[4-(n-carbonyl-2-propenyl)amidobutyl]-2,5-diketopiperazine (fdkp)
US20230263807A1 (en) 2022-02-08 2023-08-24 United Therapeutics Corporation Treprostinil iloprost combination therapy
AU2024208919A1 (en) 2023-01-19 2025-07-17 United Therapeutics Corporation Treprostinil analogs
US20250197338A1 (en) 2023-11-09 2025-06-19 United Therapeutics Corporation Syntheses of compounds useful for producing treprostinil

Family Cites Families (96)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2947526A1 (de) 1978-11-29 1980-06-12 Ono Pharmaceutical Co Prostacyclin-analoge
US4668814A (en) 1984-03-08 1987-05-26 The Upjohn Company Interphenylene carbacyclin derivatives
JPS61289034A (ja) 1985-06-17 1986-12-19 Teijin Ltd イソカルバサイクリン類脂肪乳剤
US4837342A (en) 1986-02-28 1989-06-06 Sagami Chemical Research Center Prostacyclin analogue, and blood circulation improving agent and anti-ulcer composition containing it as active ingredient
GB8814438D0 (en) 1988-06-17 1988-07-20 Wellcome Found Compounds for use in medicine
GB9011588D0 (en) 1990-05-24 1990-07-11 Wellcome Found Prostaglandin analogues for use in medicine
US6165500A (en) 1990-08-24 2000-12-26 Idea Ag Preparation for the application of agents in mini-droplets
CA2056039A1 (en) 1991-01-22 1992-07-23 Philip L. Fuchs Carbacyclin analogs
US5190972A (en) 1992-01-27 1993-03-02 The University Of Melbourne Method of combatting cyclosporine organ toxicity with prostaglandin analogs
CA2091152C (en) 1993-03-05 2005-05-03 Kirsten Westesen Solid lipid particles, particles of bioactive agents and methods for the manfuacture and use thereof
US5576016A (en) 1993-05-18 1996-11-19 Pharmos Corporation Solid fat nanoemulsions as drug delivery vehicles
US6638621B2 (en) 2000-08-16 2003-10-28 Lyotropic Therapeutics, Inc. Coated particles, methods of making and using
US6441245B1 (en) 1997-10-24 2002-08-27 United Therapeutics Corporation Process for stereoselective synthesis of prostacyclin derivatives
KR100638684B1 (ko) 1997-11-14 2006-10-27 유나이티드 세러퓨틱스 코오포레이션 말초 혈관 질환의 치료를 위한 9-데옥시-2',9-알파-메타노-3-옥사-4,5,6-트리노르-3,7-(1',3'-인터페닐렌)-13,14-디하이드로-프로스타글란딘 에프1의 용도
AU742250B2 (en) 1997-12-26 2001-12-20 Astellas Pharma Inc. Sustained release medicinal compositions
WO2000006120A1 (en) 1998-07-31 2000-02-10 Korea Institute Of Science And Technology Lipid emulsion and solid lipid nanoparticle as a gene or drug carrier
US6265495B1 (en) * 1998-09-22 2001-07-24 Nippon Shokubai Co., Ltd. Method for production of esterified product
US6521212B1 (en) 1999-03-18 2003-02-18 United Therapeutics Corporation Method for treating peripheral vascular disease by administering benzindene prostaglandins by inhalation
EP1164846A1 (en) 1999-03-31 2002-01-02 United Therapeutics Corporation Prostaglandin compounds, compositions and methods of treating peripheral vascular disease and pulmonary hypertension
US6242482B1 (en) 2000-06-05 2001-06-05 United Therapeutics Corporation Prostaglandin compounds and derivatives thereof, compositions containing the same and method of using the same for the treatment of congestive heart failure
US6306435B1 (en) 2000-06-26 2001-10-23 Yung Shin Pharmaceutical Industrial Co. Ltd. Oral pharmaceutical preparation embedded in an oily matrix and methods of making the same
CA2451432A1 (en) 2001-06-23 2003-01-03 Lyotropic Therapeutics, Inc. Particles with improved solubilization capacity
US20030108512A1 (en) 2001-12-10 2003-06-12 Robert Shorr Modified prostaglandin compounds and analogs thereof, compositions containing the same useful for the treatment of cancer
US6803386B2 (en) 2002-01-16 2004-10-12 United Therapeutics Corporation Prostacyclin derivative containing compositions and methods of using the same for the treatment of cancer
WO2004012680A2 (en) 2002-08-06 2004-02-12 Lyotropic Therapeutics, Inc. Lipid-drug complexes in reversed liquid and liquid crystalline phases
CN1791386A (zh) 2003-05-19 2006-06-21 巴克斯特国际公司 抗癫痫和抗痴呆药物以及免疫抑制剂的小－颗粒药物制剂
ATE341312T1 (de) 2003-05-20 2006-10-15 Ethypharm Sa Orale pharmazeutische zusammensetzung mit verzögerter freisetzung
ES2670872T3 (es) 2003-05-22 2018-06-01 United Therapeutics Corporation Polimorfo de una sal de dietanolamina de treprostinil
JP4906514B2 (ja) 2003-12-16 2012-03-28 ユナイテッド セラピューティクス コーポレイション 腎臓機能改善のためのトレプロスチニルの用途
US8765813B2 (en) 2003-12-16 2014-07-01 United Therapeutics Corporation Use of treprostinil to treat and prevent ischemic lesions
CA2562614C (en) 2004-04-12 2013-09-17 United Therapeutics, Inc. Use of treprostinil to treat neuropathic diabetic foot ulcers
GB0416328D0 (en) 2004-07-21 2004-08-25 Univ Cardiff Use of dry powder compositions for pulmonary delivery
EP1796653A2 (en) 2004-07-26 2007-06-20 Actelion Pharmaceuticals Ltd. Treatment of pulmonary hypertension by inhaled iloprost with a microparticle formulation
WO2006043655A1 (ja) 2004-10-22 2006-04-27 Ono Pharmaceutical Co., Ltd. 吸入用医薬組成物
JP2009519972A (ja) 2005-12-15 2009-05-21 アキュスフィア， インコーポレイテッド 粒子ベースの経肺投与または経鼻投与用製薬の製造方法
JP5797376B2 (ja) 2006-05-15 2015-10-21 ユナイテッド セラピューティクス コーポレーション 定量吸入器を用いたトレプロスチニル投与
US20090036465A1 (en) 2006-10-18 2009-02-05 United Therapeutics Corporation Combination therapy for pulmonary arterial hypertension
US20080280986A1 (en) 2007-02-09 2008-11-13 United Therapeutics Corporation Treprostinil treatment for interstitial lung disease and asthma
WO2008124632A1 (en) 2007-04-04 2008-10-16 Massachusetts Institute Of Technology Amphiphilic compound assisted nanoparticles for targeted delivery
EP2711024B1 (en) 2007-09-07 2019-03-06 United Therapeutics Corporation Buffer solutions having selective bactericidal activity against gram negative bacteria and methods of using same
WO2009078965A1 (en) 2007-12-17 2009-06-25 United Therapeutics Corporation An improved process to prepare treprostinil, the active ingredient in remodulin
KR20110010753A (ko) 2008-05-08 2011-02-07 유나이티드 세러퓨틱스 코오포레이션 트레프로스티닐 일수화물
WO2009152160A1 (en) 2008-06-10 2009-12-17 Gilead Sciences, Inc. Inhaled carbaprostacyclin and prostacyclin prodrugs for the treatment of pulmonary arterial hypertension
US20110294815A1 (en) 2008-06-27 2011-12-01 Harbeson Scott L Prostacyclin analogs
WO2010039531A1 (en) 2008-09-23 2010-04-08 Resolvyx Pharmaceuticals, Inc. Therapeutic compounds
US20120177693A1 (en) 2008-09-25 2012-07-12 Aradigm Corporation Deep lung pulmonary delivery of treprostinil
AU2010220061A1 (en) 2009-02-20 2010-09-10 Micro Labs Limited Storage stable prostaglandin product
EP2427054A4 (en) 2009-05-07 2014-01-15 United Therapeutics Corp SOLID COMPOSITIONS BASED ON PROSTACYCLINE ANALOGS
US8519178B2 (en) 2009-06-22 2013-08-27 Johnson Matthey Public Limited Company Method for the purification of prostaglandins
US20120270934A1 (en) 2009-07-03 2012-10-25 Concert Pharmaceuticals, Inc. Prostacyclin derivatives
US20120184622A1 (en) 2009-08-07 2012-07-19 Scipharm Sarl Composition for the treatment of cystic fibrosis
US20120232034A1 (en) 2009-08-21 2012-09-13 Henk-Andre Kroon Vesicular formulations
CN101669904B (zh) 2009-09-29 2011-06-22 北京中海康医药科技发展有限公司 一种依前列醇脂质纳米粒及制备方法
WO2011089216A1 (en) 2010-01-22 2011-07-28 Ascendis Pharma As Dipeptide-based prodrug linkers for aliphatic amine-containing drugs
WO2011089215A1 (en) 2010-01-22 2011-07-28 Ascendis Pharma As Dipeptide-based prodrug linkers for aromatic amine-containing drugs
JP5681276B2 (ja) 2010-03-15 2015-03-04 ユナイテッド セラピューティクス コーポレイション 肺高血圧症のための治療
US8481782B2 (en) 2010-06-03 2013-07-09 United Therapeutics Corporation Treprostinil production
WO2011159693A2 (en) 2010-06-15 2011-12-22 United Therapeutics Corporation Oral treatment of digital ischemic lesions
US20120010159A1 (en) 2010-07-09 2012-01-12 United Therapeutics Corporation Combination therapies with cox-2 inhibitors and treprostinil
CA2710726C (en) 2010-07-22 2016-02-23 Alphora Research Inc. Synthesis of treprostinil and intermediates useful therein
WO2012107364A1 (en) 2011-02-07 2012-08-16 Scipharm Sàrl Novel composition for the treatment of cystic fibrosis
JP5780775B2 (ja) 2011-02-18 2015-09-16 株式会社Ｌｔｔバイオファーマ プロスタグランジンｉ２誘導体を含有するナノ粒子
KR101454571B1 (ko) 2011-03-02 2014-10-23 유나이티드 세러퓨틱스 코오포레이션 트레프로스티닐 생산을 위한 중간체 합성
JP5850915B2 (ja) 2011-03-14 2016-02-03 国立大学法人北海道大学 肺送達のためのベクター、導入剤及び使用
CA2843506C (en) 2011-08-12 2020-05-12 Ascendis Pharma A/S Carrier-linked prodrugs having reversible carboxylic ester linkages
AU2012296949B2 (en) 2011-08-12 2016-09-15 Ascendis Pharma A/S High-loading water-soluble carrier-linked prodrugs
EP2741781A1 (en) 2011-08-12 2014-06-18 Ascendis Pharma A/S Carrier-linked treprostinil prodrugs
EP2741778A1 (en) 2011-08-12 2014-06-18 Ascendis Pharma A/S Polymeric hyperbranched carrier-linked prodrugs
US9872864B2 (en) 2011-08-12 2018-01-23 Ascendis Pharma A/S Sustained release composition of prostacyclin
WO2013024049A1 (en) 2011-08-12 2013-02-21 Ascendis Pharma A/S Protein carrier-linked prodrugs
US8524939B2 (en) 2011-08-24 2013-09-03 Chirogate International Inc. Intermediates for the synthesis of benzindene prostaglandins and preparations thereof
US9387214B2 (en) 2012-01-13 2016-07-12 United Therapeutics Corporation Method of identifying therapies for pulmonary hypertension
LT2674413T (lt) 2012-06-15 2017-09-25 Scipharm Sąrl Treprostinilo ir jo darinių gavimo būdas
ES2869701T3 (es) 2012-08-01 2021-10-25 United Therapeutics Corp Tratamiento de hipertensión arterial pulmonar con células progenitoras endoteliales tratadas con prostaciclina
IN2015DN00934A (enExample) 2012-08-01 2015-06-12 United Therapeutics Corp
JP6357481B2 (ja) 2012-11-30 2018-07-11 インスメッド， インコーポレイテッド プロスタサイクリン化合物およびプロスタサイクリン化合物を使用する方法
AU2014205557B2 (en) 2013-01-09 2017-08-10 United Therapeutics Corporation Treatment of vasculopathy with prostacyclin and mesenchymal stem cells
US9505737B2 (en) 2013-01-11 2016-11-29 Corsair Pharma, Inc. Treprostinil derivative compounds and methods of using same
ES2927844T3 (es) 2013-01-11 2022-11-11 Corsair Pharma Inc Profármacos de treprostinil
CA3125504C (en) 2013-03-14 2023-10-24 United Therapeutics Corporation Solid forms of treprostinil
KR20150128903A (ko) 2013-03-15 2015-11-18 유나이티드 세러퓨틱스 코오포레이션 트레프로스티닐의 염
WO2014160638A1 (en) 2013-03-25 2014-10-02 United Therapeutics Corporation Process of making prostacyclin compounds with linker thiol and pegylated forms
EP2991639A4 (en) 2013-04-30 2016-11-30 United Therapeutics Corp PHARMACEUTICAL FORMULATIONS WITH CONTROLLED RELEASE
WO2014203278A2 (en) 2013-06-19 2014-12-24 Msn Laboratories Private Limited NOVEL PROCESS FOR THE PREPARATION OF (1R,2R,3aS,9aS)-[[2,3,3a,4,9,9a-HEXAHYDRO-2-HYDROXY-1-[(3S)-3-HYDROXYOCTYL]-1H-BENZ[f]INDEN-5-YL]OXY]ACETIC ACID
WO2015054574A1 (en) 2013-10-11 2015-04-16 Zisman Lawrence S Spray dry formulations
SI3060041T1 (sl) 2013-10-25 2021-04-30 Insmed Incorporated Spojine prostaciklina
WO2015138423A1 (en) 2014-03-11 2015-09-17 Insmed Incorporated Prostacylin compositions and methods for using the same
ES2908142T3 (es) 2014-06-13 2022-04-27 United Therapeutics Corp Formulaciones de treprostinil
US9593061B2 (en) 2014-10-20 2017-03-14 United Therapeutics Corporation Synthesis of intermediates for producing prostacyclin derivatives
EP3904326A1 (en) 2014-11-18 2021-11-03 Insmed Incorporated Methods of manufacturing treprostinil and treprostinil derivative prodrugs
WO2016176555A1 (en) 2015-04-29 2016-11-03 Insmed Incorporated Prostacyclin compounds, compositions and methods of use thereof
US10898494B2 (en) 2016-05-05 2021-01-26 Liquidia Technologies, Inc. Dry powder treprostinil for the treatment of pulmonary hypertension
WO2017223400A1 (en) 2016-06-24 2017-12-28 Insmed Incorporated Prostacyclin compounds and compositions for treating sarcoidosis
CA3038276A1 (en) 2016-09-26 2018-03-29 United Therapeutics Corporation Treprostinil prodrugs
EP3673895A1 (en) 2018-12-28 2020-07-01 Université Libre de Bruxelles Dry powder inhalation formulation and its use for the therapeutic treatment of lungs
CN114072136B (zh) 2019-04-29 2024-11-29 英斯梅德股份有限公司 曲前列素前药的干粉组合物及其使用方法

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Publication number Publication date
CA2967385A1 (en) 2016-05-26
ES2873873T3 (es) 2021-11-04
US20250162982A1 (en) 2025-05-22
US20230250051A1 (en) 2023-08-10
JP2017535555A (ja) 2017-11-30
EP3221291A4 (en) 2018-06-27
EP3221291A1 (en) 2017-09-27
US20220135513A1 (en) 2022-05-05
US11148997B2 (en) 2021-10-19
AU2015349969A1 (en) 2017-05-25
CA2967385C (en) 2023-05-16
US10343979B2 (en) 2019-07-09
EP3221291B1 (en) 2021-03-31
HK1244783A1 (en) 2018-08-17
WO2016081658A1 (en) 2016-05-26
AU2015349969B2 (en) 2020-02-06
US20190337888A1 (en) 2019-11-07
EP3904326A1 (en) 2021-11-03
US20170320813A1 (en) 2017-11-09

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