TWI459944B - 含有硫辛酸衍生物之醫藥調配物 - Google Patents
含有硫辛酸衍生物之醫藥調配物 Download PDFInfo
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- TWI459944B TWI459944B TW097114308A TW97114308A TWI459944B TW I459944 B TWI459944 B TW I459944B TW 097114308 A TW097114308 A TW 097114308A TW 97114308 A TW97114308 A TW 97114308A TW I459944 B TWI459944 B TW I459944B
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- Prior art keywords
- lipoic acid
- pharmaceutical formulation
- group
- cancer
- acid derivative
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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- A—HUMAN NECESSITIES
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
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- A—HUMAN NECESSITIES
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A61K47/50—Medicinal 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
- A61K47/51—Medicinal 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
- A61K47/54—Medicinal 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
- A61K47/541—Organic ions forming an ion pair complex with the pharmacologically or therapeutically active agent
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- A—HUMAN NECESSITIES
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- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Oncology (AREA)
- Hematology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Medicinal Preparation (AREA)
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| US8263653B2 (en) | 2007-04-18 | 2012-09-11 | Cornerstone Pharmaceuticals, Inc. | Pharmaceutical formulations containing lipoic acid derivatives |
| MX2009011165A (es) | 2007-04-18 | 2009-12-09 | Cornerstone Pharmaceuticals In | Formulaciones farmaceuticas que contienen derivados del acido lipoico. |
| ES2442901T3 (es) * | 2007-04-18 | 2014-02-14 | Cornerstone Pharmaceuticals, Inc. | Derivados de ácido lipoico |
| CN102089276A (zh) * | 2008-03-04 | 2011-06-08 | 罗伯特·绍尔 | 酶结构、活性和/或表达水平的调节 |
| KR20110025168A (ko) * | 2008-04-04 | 2011-03-09 | 로버트 쇼어 | 약학적 조성물 |
| BRPI0916476A2 (pt) * | 2008-12-01 | 2016-02-16 | Invasc Therapeutics Inc | composição, método de tratamento para um distúrbio relacionado ao sistema renina-angiotensina-aldosterona, método para reduzir a resistência à insulina, método para tratar um distúrbio relacionado à síndrome metabólica |
| WO2010110771A2 (en) * | 2009-03-25 | 2010-09-30 | Frank Gibson | Substituted thiol-containing alkyl fatty acids and process for synthesizing derivatives thereof |
| SI2506857T1 (en) | 2009-12-01 | 2018-08-31 | Translate Bio, Inc. | Delivery of mRNA for the enrichment of proteins and enzymes in human genetic diseases |
| WO2011143590A1 (en) * | 2010-05-14 | 2011-11-17 | Cornerstone Pharmaceuticals, Inc. | Combination therapy compositions and methods using lipoic acid derivatives and an anti-proliferation agent |
| WO2011143593A1 (en) * | 2010-05-14 | 2011-11-17 | Cornerstone Pharmaceuticals, Inc. | Conjugates of a lipoic acid derivative and anti-proliferation agent and medical uses thereof |
| KR20220025112A (ko) | 2011-06-08 | 2022-03-03 | 샤이어 휴먼 지네틱 테라피즈 인크. | Mrna 전달을 위한 지질 나노입자 조성물 및 방법 |
| CN102657606B (zh) * | 2012-05-25 | 2014-01-01 | 江苏神龙药业有限公司 | 一种供静脉给药用的硫辛酸注射液 |
| EP3536787A1 (en) | 2012-06-08 | 2019-09-11 | Translate Bio, Inc. | Nuclease resistant polynucleotides and uses thereof |
| BR112015014327A2 (pt) * | 2012-12-19 | 2020-01-28 | Cornerstone Pharmaceuticals Inc | compostos farmacêuticos |
| KR102311614B1 (ko) | 2013-03-14 | 2021-10-08 | 샤이어 휴먼 지네틱 테라피즈 인크. | Cftr mrna 조성물 및 관련 방법 및 사용 |
| EA201591229A1 (ru) | 2013-03-14 | 2016-01-29 | Шир Хьюман Дженетик Терапис, Инк. | Способы очистки матричной рнк |
| CN103360437B (zh) * | 2013-04-27 | 2015-10-21 | 江苏教育学院 | 一种硫辛酸糖类衍生物及其制备方法和在制备抗肿瘤药物中的应用 |
| CN103497344B (zh) * | 2013-09-25 | 2015-09-23 | 深圳先进技术研究院 | 用于负载贵金属颗粒的纳米凝胶及其制备方法与应用 |
| ES2707966T3 (es) | 2013-10-22 | 2019-04-08 | Translate Bio Inc | Terapia de ARNm para la deficiencia en síntesis de argininosuccinato |
| EP3574923A1 (en) | 2013-10-22 | 2019-12-04 | Translate Bio, Inc. | Mrna therapy for phenylketonuria |
| EP4729528A3 (en) | 2014-04-25 | 2026-06-24 | Translate Bio, Inc. | Methods for purification of messenger rna |
| ES2747702T3 (es) * | 2014-06-19 | 2020-03-11 | Rafael Pharmaceuticals Inc | Compuestos farmacéuticos |
| EP3189033B1 (en) * | 2014-06-19 | 2020-08-05 | Rafael Pharmaceuticals, Inc. | Pharmaceutical compounds |
| MX2019010155A (es) | 2017-02-27 | 2020-12-10 | Translate Bio Inc | Arnm de cftr optimizado por codón novedoso. |
| IL270631B2 (en) | 2017-05-16 | 2024-03-01 | Translate Bio Inc | Treatment of cystic fibrosis by delivery of codon-optimized mrna encoding cftr |
| US11174500B2 (en) | 2018-08-24 | 2021-11-16 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| AU2019384557B2 (en) | 2018-11-21 | 2025-07-17 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of nebulized mRNA encoding CFTR |
| TW202114651A (zh) * | 2019-08-16 | 2021-04-16 | 美商拉斐爾製藥公司 | 用於治療癌症之方法及含有４，６—雙（苄硫基）己酸之藥物組成物 |
| CA3155003A1 (en) | 2019-09-20 | 2021-03-25 | Translate Bio, Inc. | Mrna encoding engineered cftr |
| EP4110308A4 (en) * | 2020-02-28 | 2024-03-20 | University Of Florida Research Foundation, Incorporated | ANTI-TUMOR IMMUNITY MODULATING COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| JP2023549086A (ja) * | 2020-11-03 | 2023-11-22 | コーナーストーン ファーマシューティカルズ，インコーポレーテッド | デビミスタットを使用して胆道癌を治療するための治療法及び組成物 |
| CN119770650A (zh) * | 2025-01-09 | 2025-04-08 | 华中科技大学 | 一种硫辛酸-胆碱离子液体溶液及其制备方法和应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5569670A (en) * | 1992-06-05 | 1996-10-29 | Asta Medica Aktiengesellschaft | Combination medications containing alpha-lipoic acid and related |
| WO2000024734A1 (en) * | 1998-10-26 | 2000-05-04 | The Research Foundation Of State University Of New York | Lipoic acid derivatives and their use in treatment of disease |
| US20050048008A1 (en) * | 2003-08-29 | 2005-03-03 | Bioderm Research | Antiaging Cosmetic Delivery Systems |
| JP2007077066A (ja) * | 2005-09-14 | 2007-03-29 | Shiseido Co Ltd | 不全角化抑制剤、毛穴縮小剤 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2805251A (en) * | 1953-07-22 | 1957-09-03 | Ethyl Corp | Preparation of aryloxyaliphatic acids and salts thereof |
| GB758897A (en) | 1953-10-19 | 1956-10-10 | Merck & Co Inc | Thio-substituted aliphatic carboxylic acids and their preparation |
| US3002011A (en) * | 1953-12-04 | 1961-09-26 | Merck & Co Inc | Intermediates and processes for producing alpha-lipoic acid |
| US2809978A (en) * | 1953-12-04 | 1957-10-15 | Merck & Co Inc | Intermediates useful in the synthesis of alpha-lipoic acid |
| US2980716A (en) * | 1954-06-11 | 1961-04-18 | Research Corp | Method for preparing 6, 8-dihalooctanoic esters |
| US2975198A (en) * | 1954-07-08 | 1961-03-14 | Research Corp | Lipoic acid intermediates |
| US2852531A (en) * | 1954-09-24 | 1958-09-16 | Merck & Co Inc | Tris-(2-tetrahydropyranyl) esters of 6, 8-bis (hydrocarbonmercapto)-4, 4-dicarboxy-5-ocaprylic acid and preparation thereof |
| US2875238A (en) * | 1957-02-19 | 1959-02-24 | Merck & Co Inc | Intermediates useful in the synthesis of alpha-lipoic acid |
| US2875239A (en) * | 1957-02-19 | 1959-02-24 | Merck & Co Inc | Intermediates useful in the synthesis of alpha-lipoic acid |
| US2985685A (en) * | 1959-01-26 | 1961-05-23 | American Cyanamid Co | Alkanolamine aluminates as catalysts for ester redistribution |
| US3453312A (en) * | 1966-04-27 | 1969-07-01 | Merck & Co Inc | (beta - (substituted-thio) - acylphenoxy)-alkanoic acids and (beta-(substitutedthio) acylphenylmercapto) alkanoic acids and derivatives thereof |
| US3345368A (en) * | 1967-02-15 | 1967-10-03 | American Cyanamid Co | Substituted 7-acetylamino cephalosporanic acids |
| DE2422498A1 (de) * | 1973-05-18 | 1974-12-05 | Ciba Geigy Ag | Neue thiaprostaglandine und verfahren zu ihrer herstellung |
| US3881017A (en) * | 1973-05-18 | 1975-04-29 | Ciba Geigy Corp | 9-Thiaprostaglandin compositions |
| JPS5323539Y2 (enExample) * | 1973-11-30 | 1978-06-17 | ||
| DE3512911A1 (de) * | 1985-04-11 | 1986-10-16 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von 1,2-dithiolan-3-pentansaeure (thioctsaeure) |
| US5344941A (en) * | 1986-09-03 | 1994-09-06 | Samour Carlos M | Water soluble salts of thionaphthene-2-carboxylic acid |
| DE4000397A1 (de) * | 1990-01-09 | 1991-07-11 | Hoechst Ag | Lipidselektive antioxidantien sowie deren herstellung und verwendung |
| WO1994023748A1 (en) * | 1993-04-08 | 1994-10-27 | The University Of Queensland | Administration of vaso-active agent and therapeutic agent |
| US5463093A (en) * | 1993-11-26 | 1995-10-31 | Garnett; Merrill | Palladium complexes and methods for using same in the treatment of tumors or Psoriasis |
| FR2777001B1 (fr) * | 1998-04-01 | 2000-06-09 | Cird Galderma | Derives de l'acide 6,8-dimercaptooctanoique substitues en 6-s et/ou en 8-s par le radical (3-methylthiopropanoyl) et compositions pharmaceutiques destinees au traitement des tumeurs cancereuses |
| US20090036356A1 (en) * | 2006-03-06 | 2009-02-05 | Avestha Gengraine Technologies Pvt. Ltd. | Octanoic acid derivatives as dipeptidyl peptidase inhibitors |
| ES2442901T3 (es) * | 2007-04-18 | 2014-02-14 | Cornerstone Pharmaceuticals, Inc. | Derivados de ácido lipoico |
| US8263653B2 (en) * | 2007-04-18 | 2012-09-11 | Cornerstone Pharmaceuticals, Inc. | Pharmaceutical formulations containing lipoic acid derivatives |
| MX2009011165A (es) | 2007-04-18 | 2009-12-09 | Cornerstone Pharmaceuticals In | Formulaciones farmaceuticas que contienen derivados del acido lipoico. |
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2008
- 2008-04-17 MX MX2009011165A patent/MX2009011165A/es active IP Right Grant
- 2008-04-17 ES ES08780538.8T patent/ES2528414T3/es active Active
- 2008-04-17 AU AU2008242827A patent/AU2008242827B2/en not_active Ceased
- 2008-04-17 BR BRPI0810439-5A patent/BRPI0810439B1/pt not_active IP Right Cessation
- 2008-04-17 EP EP08780538.8A patent/EP2144609B1/en not_active Not-in-force
- 2008-04-17 NZ NZ580973A patent/NZ580973A/en not_active IP Right Cessation
- 2008-04-17 JP JP2010504247A patent/JP5480804B2/ja not_active Expired - Fee Related
- 2008-04-17 PL PL08780538T patent/PL2144609T3/pl unknown
- 2008-04-17 KR KR1020097023900A patent/KR101539785B1/ko not_active Expired - Fee Related
- 2008-04-17 PT PT87805388T patent/PT2144609E/pt unknown
- 2008-04-17 CA CA2684479A patent/CA2684479C/en active Active
- 2008-04-17 US US12/105,100 patent/US20080262077A1/en not_active Abandoned
- 2008-04-17 CN CN200880017628.5A patent/CN101820875B/zh not_active Expired - Fee Related
- 2008-04-17 WO PCT/US2008/060650 patent/WO2008131114A2/en not_active Ceased
- 2008-04-18 TW TW097114308A patent/TWI459944B/zh not_active IP Right Cessation
- 2008-04-18 AR ARP080101607A patent/AR067309A1/es not_active Application Discontinuation
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2014
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2016
- 2016-04-21 US US15/134,896 patent/US9872845B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5569670A (en) * | 1992-06-05 | 1996-10-29 | Asta Medica Aktiengesellschaft | Combination medications containing alpha-lipoic acid and related |
| WO2000024734A1 (en) * | 1998-10-26 | 2000-05-04 | The Research Foundation Of State University Of New York | Lipoic acid derivatives and their use in treatment of disease |
| US20050048008A1 (en) * | 2003-08-29 | 2005-03-03 | Bioderm Research | Antiaging Cosmetic Delivery Systems |
| JP2007077066A (ja) * | 2005-09-14 | 2007-03-29 | Shiseido Co Ltd | 不全角化抑制剤、毛穴縮小剤 |
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