AU2015349969B2 - Methods of manufacturing treprostinil and treprostinil derivative prodrugs - Google Patents

Methods of manufacturing treprostinil and treprostinil derivative prodrugs Download PDF

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Publication number
AU2015349969B2
AU2015349969B2 AU2015349969A AU2015349969A AU2015349969B2 AU 2015349969 B2 AU2015349969 B2 AU 2015349969B2 AU 2015349969 A AU2015349969 A AU 2015349969A AU 2015349969 A AU2015349969 A AU 2015349969A AU 2015349969 B2 AU2015349969 B2 AU 2015349969B2
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alkyl
linear
treprostinil
formula
branched
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AU2015349969A1 (en
Inventor
Donna M. Konicek
Franziska LEIFER
Zhili Li
Vladimir Malinin
Walter Perkins
Adam PLAUNT
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Insmed Inc
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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)
AU2015349969A 2014-11-18 2015-11-18 Methods of manufacturing treprostinil and treprostinil derivative prodrugs Active AU2015349969B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
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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AU2015349969A1 AU2015349969A1 (en) 2017-05-25
AU2015349969B2 true AU2015349969B2 (en) 2020-02-06

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AU2015349969A Active AU2015349969B2 (en) 2014-11-18 2015-11-18 Methods of manufacturing treprostinil and treprostinil derivative prodrugs

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US (5) US10343979B2 (enExample)
EP (2) EP3221291B1 (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
JP6542128B2 (ja) 2013-01-11 2019-07-10 コルセア ファーマ インコーポレイテッド トレプロスチニルのプロドラッグ
US9505737B2 (en) 2013-01-11 2016-11-29 Corsair Pharma, Inc. Treprostinil derivative compounds and methods of using same
EA031604B1 (ru) 2013-10-25 2019-01-31 Инсмед Инкорпорейтед Трепростинильные соединения, композиции и способы их использования
EP3221291B1 (en) 2014-11-18 2021-03-31 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
KR102541885B1 (ko) 2016-09-26 2023-06-12 유나이티드 쎄러퓨틱스 코포레이션 트레프로스티닐 프로드럭
KR20220002600A (ko) 2019-04-29 2022-01-06 인스메드 인코포레이티드 트레프로스티닐 전구약물의 건조 분말 조성물 및 이의 사용 방법
CA3149358A1 (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
CN115916212A (zh) 2020-04-17 2023-04-04 联合治疗公司 曲前列尼尔用于治疗间质性肺病
WO2021252446A1 (en) 2020-06-09 2021-12-16 United Therapeutics Corporation Fumaryl diketopiperidine prodrugs of treprostinil
IL303668A (en) 2020-12-14 2023-08-01 United Therapeutics Corp Stable treprostinil prodrugs and their uses for the treatment of diseases
WO2022187352A1 (en) 2021-03-03 2022-09-09 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)
JP2025506019A (ja) 2022-02-08 2025-03-05 ユナイテッド セラピューティクス コーポレイション トレプロスチニルイロプロスト併用療法
IL322116A (en) 2023-01-19 2025-09-01 United Therapeutics Corp Analogues of treprostinil
US20250197338A1 (en) 2023-11-09 2025-06-19 United Therapeutics Corporation Syntheses of compounds useful for producing treprostinil

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7417070B2 (en) * 2003-05-22 2008-08-26 United Therapeutics Corporation Compounds and methods for delivery of prostacyclin analogs
US20140256730A1 (en) * 2013-01-11 2014-09-11 Corsair Pharma, Inc. Treprostinil derivative compounds and methods of using same
WO2015061720A2 (en) * 2013-10-25 2015-04-30 Insmed Incorporated Prostacyclin compounds, compositions and methods of use thereof

Family Cites Families (93)

* 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
CN1142781C (zh) 1997-11-14 2004-03-24 联合治疗公司 9－脱氧－2′,9－α－亚甲基－3－氧杂－4,5,6－三去甲－3,7－(1′,3′－间亚苯基)－13,14－二氢－前列腺素F1在治疗外周血管疾病中的用途
EP1043030A4 (en) 1997-12-26 2007-05-02 Astellas Pharma Inc MEDICINAL COMPOSITIONS WITH PROLONGED RELEASE
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
WO2000057701A1 (en) 1999-03-31 2000-10-05 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
MXPA05012467A (es) 2003-05-19 2006-02-22 Baxter Int Particulas solidas que comprenden un anticonvulsivo o un inmunosupresor revestido con uno o mas modificadores de superficie.
ATE341312T1 (de) 2003-05-20 2006-10-15 Ethypharm Sa Orale pharmazeutische zusammensetzung mit verzögerter freisetzung
CN101647792B (zh) 2003-12-16 2012-11-28 联合治疗公司 曲前列环素在制备治疗和预防缺血性损害的药物中的用途
ES2331187T3 (es) 2003-12-16 2009-12-23 United Therapeutics Corporation Utilizacion de treprostinil para mejorar las funciones renales.
DE602005020269D1 (de) 2004-04-12 2010-05-12 United Therapeutics Corp Verwendung von treprostinil zur behandlung von neuropathischen diabetischen fussgeschwüren
GB0416328D0 (en) 2004-07-21 2004-08-25 Univ Cardiff Use of dry powder compositions for pulmonary delivery
CN101090714A (zh) 2004-07-26 2007-12-19 康泽里克斯公司 通过吸入伊洛前列素和微粒制剂治疗肺动脉高血压症
US7858650B2 (en) 2004-10-22 2010-12-28 Ono Pharmaceutical Co., Ltd. Medicinal composition for inhalation
CA2631493A1 (en) 2005-12-15 2007-06-21 Acusphere, Inc. Processes for making particle-based pharmaceutical formulations for pulmonary or nasal administration
KR101390579B1 (ko) 2006-05-15 2014-05-19 유나이티드 세러퓨틱스 코오포레이션 정량 흡입기를 사용한 트레프로스티닐 투여
WO2008049000A2 (en) 2006-10-18 2008-04-24 United Therapeutics Corporation Combination therapy for pulmonary arterial hypertension
EP2120961A1 (en) 2007-02-09 2009-11-25 United Therapeutics Corporation Treprostinil treatment for interstitial lung disease and asthma
WO2008124639A2 (en) 2007-04-04 2008-10-16 Massachusetts Institute Of Technology Poly (amino acid) targeting moieties
EP2200650B1 (en) 2007-09-07 2016-01-06 United Therapeutics Corporation Buffer solutions having selective bactericidal activity against gram negative bacteria and methods of using same
CN101903324B (zh) 2007-12-17 2013-07-03 联合治疗公司 一种制备Remodulin中的活性成分曲前列素的改良方法
US8350079B2 (en) 2008-05-08 2013-01-08 United Therapeutics Corporation Treprostinil formulation
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
JP2012503668A (ja) 2008-09-25 2012-02-09 アラダイム コーポレーション 肺深部へのトレプロスチニルの肺送達
WO2010100656A2 (en) 2009-02-20 2010-09-10 Micro Labs Limited Storage stable prostaglandin product
KR101544246B1 (ko) 2009-05-07 2015-08-12 유나이티드 세러퓨틱스 코오포레이션 프로스타시클린 유사체의 고체 제제
US8519178B2 (en) 2009-06-22 2013-08-27 Johnson Matthey Public Limited Company Method for the purification of prostaglandins
WO2011003058A1 (en) 2009-07-03 2011-01-06 Concert Pharmaceuticals, Inc. Prostacyclin derivatives
HRP20140277T1 (hr) 2009-08-07 2014-04-25 Scipharm Sàrl Kompozicija za lijeäśenje cistiäśne fibroze
MX336482B (es) 2009-08-21 2016-01-21 Henk-Andre Kroon Formulaciones vesiculares.
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
DK2525830T3 (en) 2010-01-22 2016-08-15 Ascendis Pharma As DIPEPTID-BASED PRODRUG LINKERS TO ALIFATIC AMINE-CONTAINING MEDICINES
WO2011089215A1 (en) 2010-01-22 2011-07-28 Ascendis Pharma As Dipeptide-based prodrug linkers for aromatic amine-containing drugs
KR20160132501A (ko) 2010-03-15 2016-11-18 유나이티드 세러퓨틱스 코오포레이션 폐고혈압의 치료
CN103261142B (zh) 2010-06-03 2014-12-10 联合治疗公司 曲前列环素的制备
EP2582235A4 (en) 2010-06-15 2014-04-30 United Therapeutics Corp 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
US8461393B2 (en) 2011-03-02 2013-06-11 United Therapeutics Corporation Synthesis of intermediate for treprostinil production
WO2012124688A1 (ja) 2011-03-14 2012-09-20 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
IN2014CN00989A (enExample) 2011-08-12 2015-04-10 Ascendis Pharma As
HK1198913A1 (en) 2011-08-12 2015-06-19 Ascendis Pharma A/S Carrier-linked prodrugs having reversible carboxylic ester linkages
CA2843881C (en) 2011-08-12 2020-05-26 Ascendis Pharma A/S Sustained release composition of prostacyclin
US20140323402A1 (en) 2011-08-12 2014-10-30 Ascendis Phama A/S Protein Carrier-Linked Prodrugs
WO2013024047A1 (en) 2011-08-12 2013-02-21 Ascendis Pharma A/S High-loading water-soluble carrier-linked prodrugs
US20140243254A1 (en) 2011-08-12 2014-08-28 Ascendis Pharma A/S Polymeric Hyperbranched 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
ES2639823T3 (es) 2012-06-15 2017-10-30 Scipharm Sàrl Proceso para la preparación de treprostinilo y derivados del mismo
AU2013296611B2 (en) 2012-08-01 2017-11-23 United Therapeutics Corporation Treatment of pulmonary arterial hypertension with mesenchymal stem cells
WO2014022376A2 (en) 2012-08-01 2014-02-06 United Therapeutics Corporation Treatment of pulmonary arterial hypertension with prostacyclin-treated endothelial progenitor cells
WO2014085813A1 (en) 2012-11-30 2014-06-05 Insmed Incorporated Prostacylin compositions and methods for using the same
EP2943069B1 (en) 2013-01-09 2018-08-15 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
JP2016517410A (ja) 2013-03-14 2016-06-16 ユナイテッド セラピューティクス コーポレイション トレプロスチニルの固体形態
US20140275616A1 (en) 2013-03-15 2014-09-18 United Therapeutics Corporation Salts of treprostinil
KR102238501B1 (ko) 2013-03-25 2021-04-08 유나이티드 세러퓨틱스 코오포레이션 링커 티올 및 peg화된 형태를 갖는 프로스타시클린 화합물의 제조 방법
CA2911172C (en) 2013-04-30 2021-10-19 United Therapeutics Corporation Controlled release pharmaceutical formulations
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
CA2926793C (en) 2013-10-11 2022-11-22 Lawrence S. ZISMAN Spray-dry formulations for treating pulmonary arterial hypertension
WO2015138423A1 (en) 2014-03-11 2015-09-17 Insmed Incorporated Prostacylin compositions and methods for using the same
EP3164155B1 (en) 2014-06-13 2022-02-09 United Therapeutics Corporation Treprostinil formulations
JP6224872B1 (ja) 2014-10-20 2017-11-01 ユナイテッド セラピューティクス コーポレイション プロスタサイクリン誘導体を生成するための中間体の合成
EP3221291B1 (en) 2014-11-18 2021-03-31 Insmed Incorporated Methods of manufacturing treprostinil and treprostinil derivative prodrugs
US20160318844A1 (en) 2015-04-29 2016-11-03 Insmed Incorporated Prostacyclin compounds, compositions and methods of use thereof
IL262720B2 (en) 2016-05-05 2024-06-01 Liquidia Tech 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
KR102541885B1 (ko) 2016-09-26 2023-06-12 유나이티드 쎄러퓨틱스 코포레이션 트레프로스티닐 프로드럭
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
KR20220002600A (ko) 2019-04-29 2022-01-06 인스메드 인코포레이티드 트레프로스티닐 전구약물의 건조 분말 조성물 및 이의 사용 방법

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7417070B2 (en) * 2003-05-22 2008-08-26 United Therapeutics Corporation Compounds and methods for delivery of prostacyclin analogs
US20140256730A1 (en) * 2013-01-11 2014-09-11 Corsair Pharma, Inc. Treprostinil derivative compounds and methods of using same
WO2015061720A2 (en) * 2013-10-25 2015-04-30 Insmed Incorporated Prostacyclin compounds, compositions and methods of use thereof

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US20220135513A1 (en) 2022-05-05
US11148997B2 (en) 2021-10-19
EP3221291A1 (en) 2017-09-27
EP3221291A4 (en) 2018-06-27
HK1244783A1 (en) 2018-08-17
CA2967385A1 (en) 2016-05-26
US10343979B2 (en) 2019-07-09
US20250162982A1 (en) 2025-05-22
ES2873873T3 (es) 2021-11-04
US20170320813A1 (en) 2017-11-09
EP3904326A1 (en) 2021-11-03
US20230250051A1 (en) 2023-08-10
AU2015349969A1 (en) 2017-05-25
JP6866043B2 (ja) 2021-04-28
JP2017535555A (ja) 2017-11-30
WO2016081658A1 (en) 2016-05-26
EP3221291B1 (en) 2021-03-31
CA2967385C (en) 2023-05-16
US20190337888A1 (en) 2019-11-07

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