AU2021289336B2 - Fumaryl diketopiperidine prodrugs of treprostinil - Google Patents

Fumaryl diketopiperidine prodrugs of treprostinil

Info

Publication number
AU2021289336B2
AU2021289336B2 AU2021289336A AU2021289336A AU2021289336B2 AU 2021289336 B2 AU2021289336 B2 AU 2021289336B2 AU 2021289336 A AU2021289336 A AU 2021289336A AU 2021289336 A AU2021289336 A AU 2021289336A AU 2021289336 B2 AU2021289336 B2 AU 2021289336B2
Authority
AU
Australia
Prior art keywords
compound
treprostinil
fdkp
formula
protecting group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
AU2021289336A
Other languages
English (en)
Other versions
AU2021289336A1 (en
Inventor
Hitesh Batra
Liang Guo
Elizabeth Ann Harris
Patrick Poisson
Sri Harsha Tummala
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mannkind Corp
United Therapeutics Corp
Original Assignee
Mannkind Corp
United Therapeutics Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mannkind Corp, United Therapeutics Corp filed Critical Mannkind Corp
Publication of AU2021289336A1 publication Critical patent/AU2021289336A1/en
Application granted granted Critical
Publication of AU2021289336B2 publication Critical patent/AU2021289336B2/en
Priority to AU2025271417A priority Critical patent/AU2025271417A1/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/192Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/545Heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/04Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/14Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/557Eicosanoids, e.g. leukotrienes or prostaglandins
    • A61K31/5575Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Cardiology (AREA)
  • Epidemiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AU2021289336A 2020-06-09 2021-06-08 Fumaryl diketopiperidine prodrugs of treprostinil Active AU2021289336B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2025271417A AU2025271417A1 (en) 2020-06-09 2025-11-27 Fumaryl diketopiperidine prodrugs of treprostinil

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US202063036561P 2020-06-09 2020-06-09
US63/036,561 2020-06-09
PCT/US2021/036335 WO2021252446A1 (en) 2020-06-09 2021-06-08 Fumaryl diketopiperidine prodrugs of treprostinil

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU2025271417A Division AU2025271417A1 (en) 2020-06-09 2025-11-27 Fumaryl diketopiperidine prodrugs of treprostinil

Publications (2)

Publication Number Publication Date
AU2021289336A1 AU2021289336A1 (en) 2023-01-05
AU2021289336B2 true AU2021289336B2 (en) 2025-08-28

Family

ID=76731024

Family Applications (2)

Application Number Title Priority Date Filing Date
AU2021289336A Active AU2021289336B2 (en) 2020-06-09 2021-06-08 Fumaryl diketopiperidine prodrugs of treprostinil
AU2025271417A Pending AU2025271417A1 (en) 2020-06-09 2025-11-27 Fumaryl diketopiperidine prodrugs of treprostinil

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU2025271417A Pending AU2025271417A1 (en) 2020-06-09 2025-11-27 Fumaryl diketopiperidine prodrugs of treprostinil

Country Status (9)

Country Link
US (3) US11793780B2 (enExample)
EP (1) EP4161909A1 (enExample)
JP (2) JP7608480B2 (enExample)
KR (2) KR20250057075A (enExample)
CN (1) CN116113415A (enExample)
AU (2) AU2021289336B2 (enExample)
CA (1) CA3180230A1 (enExample)
IL (1) IL298591A (enExample)
WO (1) WO2021252446A1 (enExample)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013024052A1 (en) * 2011-08-12 2013-02-21 Ascendis Pharma A/S Carrier-linked treprostinil prodrugs

Family Cites Families (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2485614A (en) 1946-08-29 1949-10-25 Chicago Bridge & Iron Co Stabilizing and guide apparatus for lifter roofs
US3037116A (en) 1957-07-26 1962-05-29 Weber Georges Apparatus for irradiating liquids
US3035516A (en) 1958-08-18 1962-05-22 Lee Brothers Company Stencil device
US3646509A (en) 1969-08-08 1972-02-29 Texas Instruments Inc Method for field stacking seismic data and system using write after read bulk data storage
US4306075A (en) 1980-03-28 1981-12-15 The Upjohn Company Composition and process
US4547016A (en) 1984-08-13 1985-10-15 Eeco Incorporated Quick release mounting
GB8814438D0 (en) 1988-06-17 1988-07-20 Wellcome Found Compounds for use in medicine
IT1231076B (it) 1989-09-28 1991-11-12 Pirelli Cavi Spa Procedimento per la realizzazione di gruppo di connessione separabile per fibre ottiche riunite a nastro e gruppo di connessione con esso realizzato.
GB9011588D0 (en) 1990-05-24 1990-07-11 Wellcome Found Prostaglandin analogues for use in medicine
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
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
US6700025B2 (en) 2001-01-05 2004-03-02 United Therapeutics Corporation Process for stereoselective synthesis of prostacyclin derivatives
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
US6756117B1 (en) 2002-12-20 2004-06-29 The United States Of America As Represented By The United States Department Of Energy Photonic polymer-blend structures and method for making
ES2670872T3 (es) 2003-05-22 2018-06-01 United Therapeutics Corporation Polimorfo de una sal de dietanolamina de treprostinil
US8765813B2 (en) 2003-12-16 2014-07-01 United Therapeutics Corporation Use of treprostinil to treat and prevent ischemic lesions
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
US20090124697A1 (en) 2003-12-16 2009-05-14 United Therapeutics Corporation Inhalation formulations of treprostinil
CA2562614C (en) 2004-04-12 2013-09-17 United Therapeutics, Inc. Use of treprostinil to treat neuropathic diabetic foot ulcers
US8747897B2 (en) 2006-04-27 2014-06-10 Supernus Pharmaceuticals, Inc. Osmotic drug delivery system
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
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
EP2427054A4 (en) 2009-05-07 2014-01-15 United Therapeutics Corp SOLID COMPOSITIONS BASED ON PROSTACYCLINE ANALOGS
US20120184622A1 (en) 2009-08-07 2012-07-19 Scipharm Sarl Composition for the treatment of cystic fibrosis
EP2482840A4 (en) * 2009-08-07 2013-06-26 Mannkind Corp VAL (8) GLP-1 COMPOSITION AND METHOD FOR THE TREATMENT OF REAGENTS AND / OR IRRITATION SYNDROME
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
CA2710726C (en) 2010-07-22 2016-02-23 Alphora Research Inc. Synthesis of treprostinil and intermediates useful therein
CA2710725C (en) 2010-07-22 2017-08-01 Alphora Research Inc. Protected aldehydes for use as intermediates in chemical syntheses, and processes for their preparation
CA2726599C (en) 2010-12-30 2017-07-25 Alphora Research Inc. Process for treprostinil salt preparation
KR101454571B1 (ko) 2011-03-02 2014-10-23 유나이티드 세러퓨틱스 코오포레이션 트레프로스티닐 생산을 위한 중간체 합성
WO2013040068A2 (en) 2011-09-12 2013-03-21 Irix Pharmaceuticals, Inc. Process for preparing synthetic prostacyclins
CN103193627B (zh) 2012-01-10 2016-04-20 上海天伟生物制药有限公司 一种前列腺素类似物的晶型及其制备方法和用途
CN103193626B (zh) 2012-01-10 2016-05-11 上海天伟生物制药有限公司 一种前列腺素类似物的晶型及其制备方法和用途
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
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
MX369094B (es) 2012-12-07 2019-10-29 Cayman Chemical Co Inc Metodos para sintetizar un analogo de prostaciclina.
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
SI3060041T1 (sl) 2013-10-25 2021-04-30 Insmed Incorporated Spojine prostaciklina
JO3624B1 (ar) 2014-05-08 2020-08-27 Lilly Co Eli تركيبات إنسولين سريعة المفعول
JP6037085B2 (ja) 2014-05-14 2016-11-30 富士電機株式会社 半導体装置および半導体装置の製造方法
ES2908142T3 (es) 2014-06-13 2022-04-27 United Therapeutics Corp Formulaciones de treprostinil
US20160045470A1 (en) 2014-08-12 2016-02-18 Dr. Reddy's Laboratories Limited Amorphous solid dispersion of treprostinil diethanolamine
WO2016038532A1 (en) 2014-09-09 2016-03-17 Mylan Laboratories Limited Amorphous treprostinil diethanolamine
HU231184B1 (hu) 2014-10-08 2021-07-28 CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. Treprostinil-nátrium-monohidrát és eljárás ennek előállítására
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
TWI540121B (zh) 2014-12-01 2016-07-01 臺灣永光化學工業股份有限公司 曲前列環素二乙醇胺之合成方法及新穎中間體
US10837038B2 (en) 2014-12-23 2020-11-17 National Technology & Engineering Solutions Of Sandia, Llc Adjusting the pH of a pretreatment solution using carbon dioxide useful for integrating saccharification and fermentation
AU2017211410B2 (en) * 2016-01-29 2022-10-13 Mannkind Corporation Dry powder inhaler
CA3038276A1 (en) 2016-09-26 2018-03-29 United Therapeutics Corporation Treprostinil prodrugs
EP3498283A1 (en) 2017-12-14 2019-06-19 Ipsol AG Glycosidic derivatives of treprostinil
JP2021527058A (ja) 2018-06-07 2021-10-11 マンカインド コーポレイション 吸入のための組成物および方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013024052A1 (en) * 2011-08-12 2013-02-21 Ascendis Pharma A/S Carrier-linked treprostinil prodrugs

Also Published As

Publication number Publication date
JP2025041731A (ja) 2025-03-26
JP7608480B2 (ja) 2025-01-06
US20250302786A1 (en) 2025-10-02
CN116113415A (zh) 2023-05-12
AU2021289336A1 (en) 2023-01-05
WO2021252446A1 (en) 2021-12-16
US11793780B2 (en) 2023-10-24
CA3180230A1 (en) 2021-12-16
US20210378996A1 (en) 2021-12-09
US20240058287A1 (en) 2024-02-22
JP2023529828A (ja) 2023-07-12
KR20250057075A (ko) 2025-04-28
KR20230049613A (ko) 2023-04-13
IL298591A (en) 2023-01-01
AU2025271417A1 (en) 2025-12-18
KR102796323B1 (ko) 2025-04-16
US12357599B2 (en) 2025-07-15
EP4161909A1 (en) 2023-04-12

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