GB758897A - Thio-substituted aliphatic carboxylic acids and their preparation - Google Patents

Thio-substituted aliphatic carboxylic acids and their preparation

Info

Publication number
GB758897A
GB758897A GB29287/54A GB2928754A GB758897A GB 758897 A GB758897 A GB 758897A GB 29287/54 A GB29287/54 A GB 29287/54A GB 2928754 A GB2928754 A GB 2928754A GB 758897 A GB758897 A GB 758897A
Authority
GB
United Kingdom
Prior art keywords
acid
acids
octanoic
acylthiol
scor
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.)
Expired
Application number
GB29287/54A
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.)
Merck and Co Inc
Original Assignee
Merck and Co 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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB758897A publication Critical patent/GB758897A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 6,8-bis-(acylthiol) octanoic acids CH2(SCOR).CH2.CH(SCOR).(CH2)4.COOH in which the acyl groups RCO correspond to alkanoic acids having 2 to 7 carbon atoms. The compounds may be prepared by reacting a thioalkanoic acid having from 2 to 7 carbon atoms in the molecule with 6,8-dithioloctanoic acid, preferably in the presence of an excess of the thioalkanoic acid as solvent or an inert organic solvent such as ethanol, ether, dioxane, chloroform, hexane or "Cellosolve" (Registered Trade Mark). The reaction may be effected at ordinary or elevated temperatures. In examples, 6,8-dithiol-octanoic acid is reacted with (1) thioacetic acid, and (2) thiobutyric acid to give the corresponding 6,8-bis-(acylthiol) octanoic acids. Other suitable thioalkanols are thiopropionic, thiovaleric and thiocaproic acids. The novel compounds have a -lipoic acid activity.
GB29287/54A 1953-10-19 1954-10-11 Thio-substituted aliphatic carboxylic acids and their preparation Expired GB758897A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US758897XA 1953-10-19 1953-10-19

Publications (1)

Publication Number Publication Date
GB758897A true GB758897A (en) 1956-10-10

Family

ID=22128587

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29287/54A Expired GB758897A (en) 1953-10-19 1954-10-11 Thio-substituted aliphatic carboxylic acids and their preparation

Country Status (1)

Country Link
GB (1) GB758897A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0110225A1 (en) * 1982-11-24 1984-06-13 BASF Aktiengesellschaft Bis-(benzoylthio)-carboxylic acids, their preparation and use in the production of active ingredients
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
US8263653B2 (en) 2007-04-18 2012-09-11 Cornerstone Pharmaceuticals, Inc. Pharmaceutical formulations containing lipoic acid derivatives
US8691873B2 (en) 2007-04-18 2014-04-08 Cornerstone Pharmaceuticals, Inc. Pharmaceutical formulations containing lipoic acid derivatives
US9150509B2 (en) 2007-04-18 2015-10-06 Cornerstone Pharmaceuticals, Inc. Lipoic acid derivatives
US10179796B2 (en) 2014-06-19 2019-01-15 Rafael Pharmaceuticals, Inc. Pharmaceutical compounds
US10450337B2 (en) 2014-06-19 2019-10-22 Rafael Pharmaceuticals, Inc. Pharmaceutical compounds

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0110225A1 (en) * 1982-11-24 1984-06-13 BASF Aktiengesellschaft Bis-(benzoylthio)-carboxylic acids, their preparation and use in the production of active ingredients
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
US6331559B1 (en) 1998-10-26 2001-12-18 The Research Foundation Of State University Of New York At Stony Brook Lipoic acid derivatives and their use in treatment of disease
JP2002528446A (en) * 1998-10-26 2002-09-03 ザ・リサーチ・ファンデーション・オブ・ステート・ユニバーシティ・オブ・ニューヨーク Lipoic acid derivatives and their use in the treatment of diseases
AU774362B2 (en) * 1998-10-26 2004-06-24 Research Foundation Of The State University Of New York, The Lipoic acid derivatives and their use in treatment of disease
EP1486495A1 (en) * 1998-10-26 2004-12-15 The Research Foundation of State University of New York Lipoic acid derivatives and their use in treatment of disease
US6951887B2 (en) 1998-10-26 2005-10-04 The Research Foundation Of State University Of New York Lipoic acid derivatives and their use in treatment of disease
JP4728481B2 (en) * 1998-10-26 2011-07-20 ザ リサーチ ファウンデーション オブ ステイト ユニバーシティ オブ ニューヨーク Lipoic acid derivatives and their use in the treatment of diseases
US9150509B2 (en) 2007-04-18 2015-10-06 Cornerstone Pharmaceuticals, Inc. Lipoic acid derivatives
US8691873B2 (en) 2007-04-18 2014-04-08 Cornerstone Pharmaceuticals, Inc. Pharmaceutical formulations containing lipoic acid derivatives
US8263653B2 (en) 2007-04-18 2012-09-11 Cornerstone Pharmaceuticals, Inc. Pharmaceutical formulations containing lipoic acid derivatives
US9320726B2 (en) 2007-04-18 2016-04-26 Cornerstone Pharmaceuticals, Inc. Methods of treating colon, lung, and liver cancers using compositions containing an ion pair of a lipoic acid derivative
US9839691B2 (en) 2007-04-18 2017-12-12 Rafael Pharmaceuticals, Inc. Methods of treating pancreatic and ovarian cancers using compositions containing an ion pair of a lipoic acid derivative
US9872845B2 (en) 2007-04-18 2018-01-23 Rafael Pharmaceuticals, Inc. Methods of treating myeloma and lymphoma using compositions containing an ion pair of a lipoic acid derivative
US10098955B2 (en) 2007-04-18 2018-10-16 Rafael Pharmaceuticals, Inc. Pharmaceutical formulations containing lipoic acid derivatives
US10391177B2 (en) 2007-04-18 2019-08-27 Rafael Pharmaceuticals, Inc. Methods for treating cancer using 6,8-bis (benzylthio) octanonic acid
US11065335B2 (en) 2007-04-18 2021-07-20 Rafael Pharmaceuticals, Inc. Methods of treating leukemia using compositions containing bis(benzylthio)octanoic acid and ion pairs thereof
US10179796B2 (en) 2014-06-19 2019-01-15 Rafael Pharmaceuticals, Inc. Pharmaceutical compounds
US10450337B2 (en) 2014-06-19 2019-10-22 Rafael Pharmaceuticals, Inc. Pharmaceutical compounds
US10526357B2 (en) 2014-06-19 2020-01-07 Rafael Pharmaceuticals, Inc. Pharmaceutical compounds

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