CA2684479C - Amine salts of lipoic acid derivative and use thereof in the treatment of cancer - Google Patents

Amine salts of lipoic acid derivative and use thereof in the treatment of cancer Download PDF

Info

Publication number
CA2684479C
CA2684479C CA2684479A CA2684479A CA2684479C CA 2684479 C CA2684479 C CA 2684479C CA 2684479 A CA2684479 A CA 2684479A CA 2684479 A CA2684479 A CA 2684479A CA 2684479 C CA2684479 C CA 2684479C
Authority
CA
Canada
Prior art keywords
lipoic acid
pharmaceutical formulation
acid derivative
cancer
present
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
CA2684479A
Other languages
English (en)
French (fr)
Other versions
CA2684479A1 (en
Inventor
Robert G.L. Shorr
Rajinder Bhasin
Robert J. Rodriguez
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.)
Cornerstone Pharmaceuticals Inc
Original Assignee
Cornerstone Pharmaceuticals Inc
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 Cornerstone Pharmaceuticals Inc filed Critical Cornerstone Pharmaceuticals Inc
Publication of CA2684479A1 publication Critical patent/CA2684479A1/en
Application granted granted Critical
Publication of CA2684479C publication Critical patent/CA2684479C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K31/185—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
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61K31/185—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
    • 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
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Oncology (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)
CA2684479A 2007-04-18 2008-04-17 Amine salts of lipoic acid derivative and use thereof in the treatment of cancer Active CA2684479C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US91260507P 2007-04-18 2007-04-18
US60/912,605 2007-04-18
PCT/US2008/060650 WO2008131114A2 (en) 2007-04-18 2008-04-17 Pharmaceutical formulations containing lipoic acid derivatives

Publications (2)

Publication Number Publication Date
CA2684479A1 CA2684479A1 (en) 2008-10-30
CA2684479C true CA2684479C (en) 2017-11-14

Family

ID=39872894

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2684479A Active CA2684479C (en) 2007-04-18 2008-04-17 Amine salts of lipoic acid derivative and use thereof in the treatment of cancer

Country Status (19)

Country Link
US (4) US20080262077A1 (enExample)
EP (1) EP2144609B1 (enExample)
JP (1) JP5480804B2 (enExample)
KR (1) KR101539785B1 (enExample)
CN (1) CN101820875B (enExample)
AR (1) AR067309A1 (enExample)
AU (1) AU2008242827B2 (enExample)
BR (1) BRPI0810439B1 (enExample)
CA (1) CA2684479C (enExample)
CL (1) CL2008001124A1 (enExample)
ES (1) ES2528414T3 (enExample)
IL (1) IL201581A (enExample)
MX (1) MX2009011165A (enExample)
NZ (1) NZ580973A (enExample)
PL (1) PL2144609T3 (enExample)
PT (1) PT2144609E (enExample)
SA (1) SA08290240B1 (enExample)
TW (1) TWI459944B (enExample)
WO (1) WO2008131114A2 (enExample)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2009011165A (es) 2007-04-18 2009-12-09 Cornerstone Pharmaceuticals In Formulaciones farmaceuticas que contienen derivados del acido lipoico.
EP2139321B1 (en) * 2007-04-18 2013-11-06 Cornerstone Pharmaceuticals, Inc. Lipoic acid derivatives
US8263653B2 (en) * 2007-04-18 2012-09-11 Cornerstone Pharmaceuticals, Inc. Pharmaceutical formulations containing lipoic acid derivatives
MX2010009673A (es) * 2008-03-04 2011-03-15 Robert Shorr Modulacion de la estructura, actividad y/o nivel de expresion enzimaticos.
WO2009123597A1 (en) * 2008-04-04 2009-10-08 Robert Shorr Pharmaceutical composition
EP2389178A4 (en) * 2008-12-01 2012-06-06 Invasc Therapeutic Inc COMPOSITIONS CONTAINING INHIBITORS OF THE RENIN-ANGIOTENSIN-ALDOSTERONE SYSTEM AND LIPOIC ACID COMPOUNDS, AND THEIR USE FOR THE TREATMENT OF RENIN-ANGIOTENSIN-ALDOSTERONE ASSOCIATED DISORDERS
WO2010110771A2 (en) * 2009-03-25 2010-09-30 Frank Gibson Substituted thiol-containing alkyl fatty acids and process for synthesizing derivatives thereof
SI3338765T1 (sl) 2009-12-01 2019-05-31 Translate Bio, Inc. Derivat steroida za dostavo MRNA pri humanih genetskih boleznih
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
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
WO2012170930A1 (en) 2011-06-08 2012-12-13 Shire Human Genetic Therapies, Inc Lipid nanoparticle compositions and methods for mrna delivery
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
WO2013185067A1 (en) 2012-06-08 2013-12-12 Shire Human Genetic Therapies, Inc. Nuclease resistant polynucleotides and uses thereof
EP2934542A4 (en) * 2012-12-19 2016-08-10 Robert Shorr PHARMACEUTICAL COMPOUNDS
KR20150128687A (ko) 2013-03-14 2015-11-18 샤이어 휴먼 지네틱 테라피즈 인크. 메신저 rna의 정제 방법
MX393573B (es) 2013-03-14 2025-03-21 Shire Human Genetic Therapies Composiciones de acido ribonucleico mensajero del regulador transmembrana de fibrosis quistica y metodos y usos relacionados
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
EP3574923A1 (en) 2013-10-22 2019-12-04 Translate Bio, Inc. Mrna therapy for phenylketonuria
JP6608815B2 (ja) 2013-10-22 2019-11-20 トランスレイト バイオ， インコーポレイテッド アルギニノコハク酸合成酵素欠損症のｍＲＮＡ治療
EP3636742B1 (en) 2014-04-25 2025-11-05 Translate Bio, Inc. Methods for purification of messenger rna
ES2819175T3 (es) * 2014-06-19 2021-04-15 Rafael Pharmaceuticals Inc Compuestos farmacéuticos
EP3188726B1 (en) 2014-06-19 2019-08-07 Rafael Pharmaceuticals, Inc. Pharmaceutical compounds
EP3585417B1 (en) 2017-02-27 2023-02-22 Translate Bio, Inc. Method of making a codon-optimized cftr mrna
AU2018268859B2 (en) 2017-05-16 2024-07-25 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
WO2020106946A1 (en) 2018-11-21 2020-05-28 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
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
TW202233172A (zh) * 2020-11-03 2022-09-01 美商拉斐爾製藥公司 使用德弗米司特（ｄｅｖｉｍｉｓｔａｔ）治療膽道癌的治療方法及組合物
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

Family Cites Families (29)

* Cited by examiner, † Cited by third party
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
US2809978A (en) * 1953-12-04 1957-10-15 Merck & Co Inc Intermediates useful in the synthesis of alpha-lipoic acid
US3002011A (en) * 1953-12-04 1961-09-26 Merck & Co Inc Intermediates and processes for producing 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
US3881017A (en) * 1973-05-18 1975-04-29 Ciba Geigy Corp 9-Thiaprostaglandin compositions
DE2422498A1 (de) * 1973-05-18 1974-12-05 Ciba Geigy Ag Neue thiaprostaglandine und verfahren zu ihrer herstellung
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
US5569670A (en) * 1992-06-05 1996-10-29 Asta Medica Aktiengesellschaft Combination medications containing alpha-lipoic acid and related
US5750141A (en) * 1993-04-08 1998-05-12 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
MXPA01004152A (es) * 1998-10-26 2002-06-04 Univ New York State Res Found Derivados de acido lipoico y su uso en el tratamiento de enfermedades.
US7320797B2 (en) * 2003-08-29 2008-01-22 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
US20090036356A1 (en) * 2006-03-06 2009-02-05 Avestha Gengraine Technologies Pvt. Ltd. Octanoic acid derivatives as dipeptidyl peptidase inhibitors
US8263653B2 (en) * 2007-04-18 2012-09-11 Cornerstone Pharmaceuticals, Inc. Pharmaceutical formulations containing lipoic acid derivatives
EP2139321B1 (en) * 2007-04-18 2013-11-06 Cornerstone Pharmaceuticals, Inc. Lipoic acid derivatives
MX2009011165A (es) 2007-04-18 2009-12-09 Cornerstone Pharmaceuticals In Formulaciones farmaceuticas que contienen derivados del acido lipoico.

Also Published As

Publication number Publication date
IL201581A0 (en) 2010-05-31
US9872845B2 (en) 2018-01-23
US9320726B2 (en) 2016-04-26
PL2144609T3 (pl) 2015-04-30
CN101820875B (zh) 2014-07-23
CA2684479A1 (en) 2008-10-30
US8691873B2 (en) 2014-04-08
AR067309A1 (es) 2009-10-07
US20080262077A1 (en) 2008-10-23
HK1140424A1 (en) 2010-10-15
CL2008001124A1 (es) 2009-01-02
JP5480804B2 (ja) 2014-04-23
CN101820875A (zh) 2010-09-01
TW200901964A (en) 2009-01-16
AU2008242827A1 (en) 2008-10-30
EP2144609A4 (en) 2010-06-16
PT2144609E (pt) 2015-02-06
US20170056355A1 (en) 2017-03-02
NZ580973A (en) 2011-10-28
TWI459944B (zh) 2014-11-11
ES2528414T3 (es) 2015-02-10
KR20100029744A (ko) 2010-03-17
MX2009011165A (es) 2009-12-09
KR101539785B1 (ko) 2015-07-27
BRPI0810439A2 (pt) 2014-10-07
WO2008131114A3 (en) 2010-01-21
WO2008131114A2 (en) 2008-10-30
US20120178812A1 (en) 2012-07-12
SA08290240B1 (ar) 2012-02-22
BRPI0810439B1 (pt) 2021-06-29
IL201581A (en) 2016-04-21
EP2144609A2 (en) 2010-01-20
JP2010524963A (ja) 2010-07-22
EP2144609B1 (en) 2014-10-29
AU2008242827B2 (en) 2014-06-05
US20150011633A1 (en) 2015-01-08

Similar Documents

Publication Publication Date Title
CA2684479C (en) Amine salts of lipoic acid derivative and use thereof in the treatment of cancer
US11065335B2 (en) Methods of treating leukemia using compositions containing bis(benzylthio)octanoic acid and ion pairs thereof
JP5412423B2 (ja) リポ酸誘導体
RU2016147575A (ru) Непрерывное введение l-допа, ингибиторов допа-декарбоксилазы, ингибиторов катехол-о-метилтрансферазы и предназначенные для этого композиции
JP2010524963A5 (enExample)
HK1140424B (en) Pharmaceutical formulations containing lipoic acid derivatives
US20220184212A1 (en) Pharmaceutical formulations containing lipoic acid derivatives
CN104415033B (zh) 取代唑类化合物作为制备抗肿瘤药物的应用

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20130415