CA2526534C - Compounds and methods for delivery of prostacyclin analogs - Google Patents

Compounds and methods for delivery of prostacyclin analogs Download PDF

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Publication number
CA2526534C
CA2526534C CA2526534A CA2526534A CA2526534C CA 2526534 C CA2526534 C CA 2526534C CA 2526534 A CA2526534 A CA 2526534A CA 2526534 A CA2526534 A CA 2526534A CA 2526534 C CA2526534 C CA 2526534C
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Prior art keywords
treprostinil
compound
groups
group
substituted
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Expired - Lifetime
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CA2526534A
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English (en)
French (fr)
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CA2526534A1 (en
Inventor
Ken Phares
David Mottola
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United Therapeutics Corp
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United Therapeutics Corp
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Application filed by United Therapeutics Corp filed Critical United Therapeutics Corp
Priority to CA2736406A priority Critical patent/CA2736406C/en
Publication of CA2526534A1 publication Critical patent/CA2526534A1/en
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
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    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/125Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
    • C07C59/13Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups containing rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • 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
    • AHUMAN NECESSITIES
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    • 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 
    • AHUMAN NECESSITIES
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    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/21Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • AHUMAN NECESSITIES
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    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/21Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/223Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
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    • A61K31/215Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/08Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C235/04Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/08Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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    • C07C259/04Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07C59/40Unsaturated compounds
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    • C07C59/64Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
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    • C07C69/67Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708Ethers
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CA2526534A 2003-05-22 2004-05-24 Compounds and methods for delivery of prostacyclin analogs Expired - Lifetime CA2526534C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2736406A CA2736406C (en) 2003-05-22 2004-05-24 Compositions comprising diethanolamine salts of trepostinil in the treatment of pulmonary hypertension and other cardiovascular diseases

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US47240703P 2003-05-22 2003-05-22
US60/472,407 2003-05-22
PCT/US2004/016401 WO2005007081A2 (en) 2003-05-22 2004-05-24 Compounds and methods for delivery of prostacyclin analogs

Related Child Applications (1)

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CA2736406A Division CA2736406C (en) 2003-05-22 2004-05-24 Compositions comprising diethanolamine salts of trepostinil in the treatment of pulmonary hypertension and other cardiovascular diseases

Publications (2)

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CA2526534A1 CA2526534A1 (en) 2005-01-27
CA2526534C true CA2526534C (en) 2011-07-12

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Family Applications (4)

Application Number Title Priority Date Filing Date
CA2526534A Expired - Lifetime CA2526534C (en) 2003-05-22 2004-05-24 Compounds and methods for delivery of prostacyclin analogs
CA2851309A Expired - Lifetime CA2851309C (en) 2003-05-22 2004-05-24 Compositions comprising diethanolamine salts of treprostinil in the treatment of pulmonary hypertension and other cardiovascular diseases
CA2959852A Abandoned CA2959852A1 (en) 2003-05-22 2004-05-24 Compounds and methods for delivery of prostacyclin analogs
CA2736406A Expired - Lifetime CA2736406C (en) 2003-05-22 2004-05-24 Compositions comprising diethanolamine salts of trepostinil in the treatment of pulmonary hypertension and other cardiovascular diseases

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CA2851309A Expired - Lifetime CA2851309C (en) 2003-05-22 2004-05-24 Compositions comprising diethanolamine salts of treprostinil in the treatment of pulmonary hypertension and other cardiovascular diseases
CA2959852A Abandoned CA2959852A1 (en) 2003-05-22 2004-05-24 Compounds and methods for delivery of prostacyclin analogs
CA2736406A Expired - Lifetime CA2736406C (en) 2003-05-22 2004-05-24 Compositions comprising diethanolamine salts of trepostinil in the treatment of pulmonary hypertension and other cardiovascular diseases

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US (19) US7417070B2 (https=)
EP (2) EP1628654B2 (https=)
JP (2) JP5043433B2 (https=)
KR (1) KR101072339B1 (https=)
CN (4) CN101265226B (https=)
CA (4) CA2526534C (https=)
ES (2) ES2670872T3 (https=)
WO (1) WO2005007081A2 (https=)

Families Citing this family (87)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10214983A1 (de) * 2002-04-04 2004-04-08 TransMIT Gesellschaft für Technologietransfer mbH Vernebelbare Liposomen und ihre Verwendung zur pulmonalen Applikation von Wirkstoffen
CN101265226B (zh) * 2003-05-22 2013-04-24 联合治疗公司 化合物和释放前列环素类似物的方法
CA2549801C (en) * 2003-12-16 2012-10-16 United Therapeutics Corporation Use of treprostinil to improve kidney functions
US20090124697A1 (en) 2003-12-16 2009-05-14 United Therapeutics Corporation Inhalation formulations of treprostinil
CN1917866B (zh) * 2003-12-16 2010-12-15 联合治疗公司 曲前列环素或它的衍生物,或其药学上可接受的盐在制备治疗和预防缺血性损害的药物中的用途
ATE462427T1 (de) 2004-04-12 2010-04-15 United Therapeutics Corp Verwendung von treprostinil zur behandlung von neuropathischen diabetischen fussgeschwüren
US8623917B2 (en) * 2005-06-02 2014-01-07 The Regents Of The University Of Colorado, A Body Corporate Uses of prostacyclin analogs
US8747897B2 (en) 2006-04-27 2014-06-10 Supernus Pharmaceuticals, Inc. Osmotic drug delivery system
CN101495122B (zh) * 2006-05-15 2011-10-05 联合治疗公司 使用定量吸入器给予曲前列尼
DE102006026786A1 (de) 2006-06-07 2007-12-13 Joachim Kern Dosierinhalator
US20090036465A1 (en) * 2006-10-18 2009-02-05 United Therapeutics Corporation Combination therapy for pulmonary arterial hypertension
US20100048693A1 (en) * 2006-12-04 2010-02-25 The Regents Of The University Of Colorado, A Body Corporate Treatment of COPD
CA2678258A1 (en) * 2007-02-09 2008-08-14 United Therapeutics Corporation Treprostinil treatment for interstitial lung disease and asthma
KR20160048222A (ko) 2007-12-17 2016-05-03 유나이티드 세러퓨틱스 코오포레이션 레모둘린?의 활성 성분인 트레프로스티닐의 개선된 제조 방법
US8350079B2 (en) * 2008-05-08 2013-01-08 United Therapeutics Corporation Treprostinil formulation
US20110294815A1 (en) * 2008-06-27 2011-12-01 Harbeson Scott L Prostacyclin analogs
JP5649645B2 (ja) * 2009-05-07 2015-01-07 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アナログの固形製剤
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
DE102009031274A1 (de) 2009-06-30 2011-01-13 Justus-Liebig-Universität Giessen Liposomen zur pulmonalen Applikation
RS53234B (sr) * 2009-08-07 2014-08-29 Scipharm Sàrl Kompozicija za lečenje cistične fibroze
EP3108888B1 (en) 2010-03-15 2020-02-12 United Therapeutics Corporation Treatment for pulmonary hypertension
WO2011153363A1 (en) 2010-06-03 2011-12-08 United Therapeutics Corporation Treprostinil production
WO2011159693A2 (en) * 2010-06-15 2011-12-22 United Therapeutics Corporation Oral treatment of digital ischemic lesions
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
US10920242B2 (en) 2011-02-25 2021-02-16 Recombinetics, Inc. Non-meiotic allele introgression
EP2681204B1 (en) 2011-03-02 2016-04-27 United Therapeutics Corporation Synthesis of intermediate for treprostinil production
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
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
US9387214B2 (en) 2012-01-13 2016-07-12 United Therapeutics Corporation Method of identifying therapies for pulmonary hypertension
PL2674413T3 (pl) * 2012-06-15 2018-05-30 Scipharm Sàrl Sposób wytwarzania treprostynilu i jego pochodnych
AU2013351934B2 (en) * 2012-11-30 2018-03-29 Insmed Incorporated Prostacylin compositions and methods for using the same
CN104837806A (zh) * 2012-12-07 2015-08-12 开曼化学股份有限公司 前列环素类似物的合成方法
CN106831680B (zh) * 2012-12-20 2020-01-17 江苏盛迪医药有限公司 一种制备曲前列尼尔的中间体、其制备方法以及通过其制备曲前列尼尔的方法
US9505737B2 (en) 2013-01-11 2016-11-29 Corsair Pharma, Inc. Treprostinil derivative compounds and methods of using same
EP3712142B1 (en) 2013-01-11 2022-07-06 Corsair Pharma, Inc. Prodrugs of treprostinil
EP2970091A4 (en) 2013-03-14 2017-02-08 United Therapeutics Corporation Solid forms of treprostinil
US20140275616A1 (en) * 2013-03-15 2014-09-18 United Therapeutics Corporation Salts of treprostinil
EP2978313B1 (en) 2013-03-25 2018-02-21 United Therapeutics Corporation Process of making prostacyclin compounds with linker thiol and pegylated forms
CN105407883A (zh) 2013-04-30 2016-03-16 联合治疗学有限公司 控释药物制剂
LT3060041T (lt) * 2013-10-25 2021-03-25 Insmed Incorporated Prostaciklino junginiai
US9895465B2 (en) * 2014-03-12 2018-02-20 Pioneer Surgical Technology, Inc. Absorbable compositions and methods for their use in hemostasis
CN106573066A (zh) 2014-06-13 2017-04-19 联合治疗学有限公司 曲前列环素制剂
EP3828160A1 (en) 2014-07-16 2021-06-02 Corsair Pharma, Inc. Treprostinil derivative compounds and methods of using same
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
ES2778274T3 (es) 2014-10-20 2020-08-10 United Therapeutics Corp Síntesis de productos intermedios para producir derivados de prostaciclina
JP6866043B2 (ja) * 2014-11-18 2021-04-28 インスメッド インコーポレイテッド 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
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
IL252577B (en) 2014-12-03 2022-07-01 Steadymed Ltd Preservative-free treprostinil formulations and methods and devices for use with same
CN104783298A (zh) * 2015-03-24 2015-07-22 湖州珍贝羊绒制品有限公司 一种生物灭菌组合物及其纳米乳的制备与应用
WO2016176555A1 (en) * 2015-04-29 2016-11-03 Insmed Incorporated Prostacyclin compounds, compositions and methods of use thereof
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
US11069054B2 (en) 2015-12-30 2021-07-20 Visiongate, Inc. System and method for automated detection and monitoring of dysplasia and administration of immunotherapy and chemotherapy
US10898494B2 (en) 2016-05-05 2021-01-26 Liquidia Technologies, Inc. Dry powder treprostinil for the treatment of pulmonary hypertension
LT3512495T (lt) * 2016-09-15 2022-12-27 Camurus Ab Prostaciklino analogo vaisto formos
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
US20190290597A1 (en) 2016-12-05 2019-09-26 Corsair Pharma, Inc. Dermal and transdermal administration of treprostinil and salts thereof
US10799653B2 (en) 2017-01-09 2020-10-13 United Therapeutics Corporation Aerosol delivery device and method for manufacturing and operating the same
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
MX2020011323A (es) * 2018-05-07 2020-11-18 Pharmosa Biopharm Inc Composicion farmaceutica para liberacion controlada de treprostinil.
AU2019344541B2 (en) * 2018-09-18 2022-01-06 Eli Lilly And Company Erbumine salt of treprostinil
JP7455144B2 (ja) 2019-04-29 2024-03-25 インスメッド インコーポレイテッド トレプロスチニルプロドラッグの乾燥粉末組成物およびその使用方法
JP2020011957A (ja) * 2019-07-22 2020-01-23 コルセア ファーマ インコーポレイテッド トレプロスチニル誘導体化合物およびその使用方法
JP2022546314A (ja) * 2019-08-23 2022-11-04 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
US10781160B1 (en) * 2019-10-04 2020-09-22 Chirogate International Inc. Hexadecyl Treprostinil crystals and methods for preparation thereof
WO2021126884A1 (en) 2019-12-16 2021-06-24 Tenax Therapeutics, Inc. LEVOSIMENDAN FOR TREATING PULMONARY HYPERTENSION WITH HEART FAILURE WITH PRESERVED EJECTION FRACTION (PH-HF-pEF)
AU2021255621A1 (en) 2020-04-17 2022-10-20 United Therapeutics Corporation Treprostinil for use in the treatment of intersitial lung disease
JP7608480B2 (ja) 2020-06-09 2025-01-06 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フマリルジケトピペリジンプロドラッグ
JP7138685B2 (ja) * 2020-10-26 2022-09-16 コルセア ファーマ インコーポレイテッド トレプロスチニル誘導体化合物およびその使用方法
KR20230096998A (ko) * 2020-10-28 2023-06-30 인스메드 인코포레이티드 트레프로스티닐 전구약물의 건조 분말 조성물 및 이의 사용 방법
US11447440B2 (en) 2020-10-29 2022-09-20 Chirogate International Inc. Treprostinil monohydrate crystals and methods for preparation thereof
WO2022132655A1 (en) * 2020-12-14 2022-06-23 United Therapeutics Corporation Methods of treating disease with treprostinil prodrugs
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)
CN113552265B (zh) * 2021-09-17 2022-01-04 天地恒一制药股份有限公司 富马酸丙酚替诺福韦合成原料中杂质的检测方法及应用
EP4456897A4 (en) 2021-12-31 2025-12-10 Tenax Therapeutics Inc ORAL FORMULATIONS OF LEVOSIMENDAN FOR THE TREATMENT OF PULMONARY HYPERTENSION WITH HEART FAILURE AND PRESERVED EJECTION FRACTION
CN116444377A (zh) * 2022-01-07 2023-07-18 广州楷石医药有限公司 一种氧化氮供体型曲前列尼尔类衍生物及其药物组合物和用途
US20230263807A1 (en) 2022-02-08 2023-08-24 United Therapeutics Corporation Treprostinil iloprost combination therapy
KR20250002687A (ko) 2022-04-29 2025-01-07 자오커 파마슈티컬 (광저우) 컴퍼니., 리미티드 트레프로스티닐 소프트 미스트 흡입제
IL320516A (en) 2022-10-31 2025-06-01 United Therapeutics Corp Methods for treating pulmonary hypertension
AU2024208919A1 (en) 2023-01-19 2025-07-17 United Therapeutics Corporation Treprostinil analogs
CN117800845B (zh) * 2023-03-28 2026-04-14 广州楷石医药有限公司 一种羟基取代曲前列尼尔衍生物、合成方法及其应用
US20250049743A1 (en) 2023-08-08 2025-02-13 United Therapeutics Corporation Method of producing an oral osmotic pharmaceutical delivery system and a pharmaceutical batch produced using the same
US20250197338A1 (en) 2023-11-09 2025-06-19 United Therapeutics Corporation Syntheses of compounds useful for producing treprostinil
WO2026035705A1 (en) 2024-08-06 2026-02-12 United Therapeutics Corporation Treating pulmonary hypertension based on novel biomarker

Family Cites Families (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US515322A (en) * 1894-02-27 Railroad-car
US3515222A (en) * 1968-06-19 1970-06-02 American Tractor Equip Corp Cable plow mounting
US4490537A (en) 1977-04-19 1984-12-25 The Upjohn Company Enlarged-hetero-ring prostacyclin analogs
CA1201712A (en) 1980-02-28 1986-03-11 Paul A. Aristoff Carbacyclin analogs
US4338457A (en) 1980-02-28 1982-07-06 The Upjohn Company Composition and process
US4525586A (en) 1980-02-28 1985-06-25 The Upjohn Company Composition and process
US4306075A (en) 1980-03-28 1981-12-15 The Upjohn Company Composition and process
US4420632A (en) 1980-04-15 1983-12-13 The Upjohn Company Composition and process
US4306076A (en) 1980-04-23 1981-12-15 The Upjohn Company Inter-phenylene CBA compounds
US4349689A (en) * 1980-12-22 1982-09-14 The Upjohn Company Methano carbacyclin analogs
US4434164A (en) 1981-06-01 1984-02-28 Pfizer Inc. Crystalline benzothiazine dioxide salts
US4486598A (en) 1982-02-22 1984-12-04 The Upjohn Company Carbacyclin analogs
DE3315356A1 (de) 1982-04-30 1983-11-17 Ono Pharmaceutical Co. Ltd., Osaka Verwendung von prostaglandinanalogen
US4561604A (en) 1983-07-18 1985-12-31 Shimano Industrial Company Limited Spinning reel
FI67490C (fi) 1983-11-02 1985-04-10 Fluilogic Systems Oy Filtreringsenhet
US4744989A (en) 1984-02-08 1988-05-17 E. R. Squibb & Sons, Inc. Method of preparing liposomes and products produced thereby
US4668814A (en) * 1984-03-08 1987-05-26 The Upjohn Company Interphenylene carbacyclin derivatives
US4683330A (en) 1984-03-08 1987-07-28 The Upjohn Company Interphenylene carbacyclin derivatives
CA1241324A (en) 1984-03-08 1988-08-30 Paul A. Aristoff Interphenylene carbacyclin derivatives
DE3427797A1 (de) 1984-07-25 1986-02-06 Schering AG, 1000 Berlin und 4709 Bergkamen Zytoprotektive wirkung von prostacyclin-derivaten an leber, bauchspeicheldruese und niere
US5663203A (en) 1986-09-11 1997-09-02 Schering Aktiengesellschaft Agents containing prostacyclin derivatives for topical application
GB8824187D0 (en) 1988-10-14 1988-11-23 Wellcome Found Compounds for use in medicine
GB8814438D0 (en) 1988-06-17 1988-07-20 Wellcome Found Compounds for use in medicine
US5545671A (en) * 1989-10-05 1996-08-13 Schering Aktiengesellschaft Antimetastically acting agents
GB9011588D0 (en) 1990-05-24 1990-07-11 Wellcome Found Prostaglandin analogues for use in medicine
DE4104606C1 (https=) 1991-02-12 1992-10-15 Schering Ag Berlin Und Bergkamen, 1000 Berlin, De
US5496850A (en) * 1991-04-11 1996-03-05 Toray Industries, Inc. Antimetastasis agent of malignant tumors
DE4135193C1 (https=) 1991-10-22 1993-03-11 Schering Ag Berlin Und Bergkamen, 1000 Berlin, De
US5190972A (en) 1992-01-27 1993-03-02 The University Of Melbourne Method of combatting cyclosporine organ toxicity with prostaglandin analogs
DE4202665A1 (de) 1992-01-28 1993-07-29 Schering Ag Prostacyclin- und carbacyclinderivate als mittel zur behandlung von multipler sklerose
US6171786B1 (en) 1992-09-17 2001-01-09 Board Of Trustees Of University Of Illinois Methods for preventing multidrug resistance in cancer cells
US5466203A (en) * 1994-03-30 1995-11-14 Chen; George Magnetically controlled load adjusting structure of gymnastic apparatus
ATE314054T1 (de) 1996-10-25 2006-01-15 Shire Lab Inc Osmotisches verabreichungssystem für lösliche dosen
JP3744941B2 (ja) 1997-03-14 2006-02-15 東レ株式会社 プロスタグランジンi誘導体徐放性製剤
US6451815B1 (en) 1997-08-14 2002-09-17 Aventis Pharmaceuticals Inc. Method of enhancing bioavailability of fexofenadine and its derivatives
GB9718903D0 (en) 1997-09-05 1997-11-12 Glaxo Group Ltd Method,compositions and kits for increasing the oral bioavailability of pharmaceutical agents
US6441245B1 (en) 1997-10-24 2002-08-27 United Therapeutics Corporation Process for stereoselective synthesis of prostacyclin derivatives
ES2198760T3 (es) 1997-10-24 2004-02-01 United Therapeutics Corporation Procedimiento para la sintesis estereoselectiva de derivados de prostaciclina.
EP1045695B1 (en) 1997-11-14 2004-03-24 United Therapeutics Corporation Use of 9-deoxy-2', 9-alpha-methano-3- oxa-4,5,6- trinor-3, 7-(1',3'-interphenylene) -13,14-dihydro- prostaglandin f 1? to treat peripheral vascular disease
US20010038855A1 (en) 1998-06-05 2001-11-08 Desjardin Michael A. Dosage form for administering prescribed dose
US6706283B1 (en) 1999-02-10 2004-03-16 Pfizer Inc Controlled release by extrusion of solid amorphous dispersions of drugs
EP1163333B1 (en) * 1999-03-18 2007-11-07 Queen Mary And Westfield College Inhibitors of endothelin-1 synthesis
US6521212B1 (en) 1999-03-18 2003-02-18 United Therapeutics Corporation Method for treating peripheral vascular disease by administering benzindene prostaglandins by inhalation
CN1354622A (zh) * 1999-03-31 2002-06-19 联合治疗公司 前列腺素类化合物、组合物和治疗外周血管疾病和肺动脉高压的方法
US6570013B2 (en) 2000-02-16 2003-05-27 Pfizer Inc Salts of zopolrestat
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
AU2001278115A1 (en) * 2000-08-04 2002-02-18 Longwood Pharmaceutical Research, Inc. Formulations of mometasone and a bronchodilator for pulmonary administration
US20020090388A1 (en) 2000-12-01 2002-07-11 Humes H. David Intravascular drug delivery device and use therefor
US6700025B2 (en) 2001-01-05 2004-03-02 United Therapeutics Corporation Process for stereoselective synthesis of prostacyclin derivatives
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
US7132453B2 (en) 2002-03-15 2006-11-07 Vanderbilt University Method of using prostacyclin to treat respiratory syncytial virus infections
DE10214983A1 (de) 2002-04-04 2004-04-08 TransMIT Gesellschaft für Technologietransfer mbH Vernebelbare Liposomen und ihre Verwendung zur pulmonalen Applikation von Wirkstoffen
CN101265226B (zh) * 2003-05-22 2013-04-24 联合治疗公司 化合物和释放前列环素类似物的方法
US20050101608A1 (en) 2003-09-24 2005-05-12 Santel Donald J. Iloprost in combination therapies for the treatment of pulmonary arterial hypertension
US20050254032A1 (en) 2003-11-13 2005-11-17 Fuji Photo Film Co., Ltd. Exposure device
CN1917866B (zh) 2003-12-16 2010-12-15 联合治疗公司 曲前列环素或它的衍生物,或其药学上可接受的盐在制备治疗和预防缺血性损害的药物中的用途
CA2678258A1 (en) 2007-02-09 2008-08-14 United Therapeutics Corporation Treprostinil treatment for interstitial lung disease and asthma
KR20160048222A (ko) * 2007-12-17 2016-05-03 유나이티드 세러퓨틱스 코오포레이션 레모둘린?의 활성 성분인 트레프로스티닐의 개선된 제조 방법
US8350079B2 (en) * 2008-05-08 2013-01-08 United Therapeutics Corporation Treprostinil formulation
JP2010244388A (ja) * 2009-04-08 2010-10-28 Pioneer Electronic Corp 情報提供装置、情報提供方法、及び情報提供用プログラム
JP5649645B2 (ja) 2009-05-07 2015-01-07 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アナログの固形製剤
WO2011153363A1 (en) * 2010-06-03 2011-12-08 United Therapeutics Corporation Treprostinil production

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