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WO2006117995A1 - Agent thérapeutique contre la perte des cheveux - Google Patents

Agent thérapeutique contre la perte des cheveux Download PDF

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Publication number
WO2006117995A1
WO2006117995A1 PCT/JP2006/307814 JP2006307814W WO2006117995A1 WO 2006117995 A1 WO2006117995 A1 WO 2006117995A1 JP 2006307814 W JP2006307814 W JP 2006307814W WO 2006117995 A1 WO2006117995 A1 WO 2006117995A1
Authority
WO
WIPO (PCT)
Prior art keywords
dimercaptootatanyl
metal chelate
acid
hair loss
active ingredient
Prior art date
Application number
PCT/JP2006/307814
Other languages
English (en)
Japanese (ja)
Inventor
Kazumi Ogata
Chikanori Katano
Original Assignee
Iwaki & Co., Ltd.
Oga Research, Incorporated
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 Iwaki & Co., Ltd., Oga Research, Incorporated filed Critical Iwaki & Co., Ltd.
Publication of WO2006117995A1 publication Critical patent/WO2006117995A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid

Definitions

  • the present invention relates to a treatment for hair loss comprising lipoic acid or a lipoic acid derivative, a method for treating hair loss by administering a compound thereof, and a method for producing a therapeutic agent for hair loss. It relates to the use of compounds.
  • Lipoic acid also known as a-lipoic acid, thiotate or 6,8 dithiooctanoate
  • its reduced form includes oxidized dartathione and oxidized vitamin C.
  • the reduced form of lipoic acid is very unstable in the air and quickly oxidizes to return to lipoic acid. Therefore, when it can come into contact with air (oxygen), it remains as a reduced form. I can't leave it!
  • the present inventor uses a derivative of lipoic acid and an amino acid as a reduced form (that is, a dihydro form in which an SS bond is cleaved), and chelates the metal to stabilize the reduced form.
  • a derivative of lipoic acid and an amino acid as a reduced form (that is, a dihydro form in which an SS bond is cleaved)
  • Successful and thus obtained compounds ie, (6,8-dimercaptootatanyl) amino acid metal chelate compounds, have an antioxidant action, a free radical inhibitory action, a melanin production inhibitory action, and an elastase inhibitory action.
  • it has also been found in an international application that it has a therapeutic Z-removing effect on spots, freckles, and moles (see Patent Document 1).
  • the present inventor further added a metal chelate compound of 6,8-dimercaptooctanoic acid (and its derivatives with alcohols, amino acids, amines and peptides) to remove melanin such as stains, freckles, and moles.
  • a metal chelate compound of 6,8-dimercaptooctanoic acid and its derivatives with alcohols, amino acids, amines and peptides
  • melanin such as stains, freckles, and moles.
  • the male hormone (testosterone) is transformed into 5a-dihydrotestosterone (5a-DHT) by the reducing action of an enzyme called 5a reductase present in the hair papilla and sebaceous glands.
  • 5a-DHT 5a-dihydrotestosterone
  • 5a reductase an enzyme called 5a reductase present in the hair papilla and sebaceous glands.
  • 5a-DHT suppresses the division of hair matrix cells, and there is a theory that this causes hair loss.
  • the theory that excessive secretion of sebum in the scalp promotes hair loss, that is, sebum on the scalp is air and light.
  • Patent Document 1 WO2002 / 076935
  • Patent Document 1 WO2004 / 024139
  • the present invention first aims to provide means for suppressing hair loss from the viewpoint of preventing hair loss from promoting hair growth. And for this purpose, the present inventor conducted research to find a substance that suppresses hair loss, and as a result, lipoic acid and its derivatives and their salts have the effect of inhibiting testosterone 5a reductase, The present invention has been completed through further investigations, which have been found to be effective in preventing hair loss.
  • the present invention provides the following.
  • a therapeutic agent for hair loss comprising a lipoic acid or lipoic acid derivative or a pharmaceutically acceptable salt thereof as an active ingredient.
  • the active ingredient is 6,8-dimercaptooctanoic acid amide metal chelate, N- (6,8-dimercaptootatanyl) 2 aminoethanol metal chelate, N- (6,8 dimercaptootatanyl) isopropylamine metal Chelate, N- (6,8-dimercaptootatanyl) melatonin metal chelate and N- (6,8 dimercaptootatanyl) 2 aminobilidine metal chelate.
  • amino acid is selected from the group power of ⁇ -amino acid, ⁇ amino acid, and special amino acid power.
  • the active ingredient is ⁇ — (6,8-dimercaptootatanyl) -a-amino acid metal chelate, N— (6,8-dimercaptootathanyl) ⁇ amino acid metal chelate and ⁇ — ( 6,
  • the active ingredient is ⁇ reboylglycine, ⁇ ⁇ reboylalanine, ⁇ ⁇ lipoyl threonine, ⁇ ⁇ lipoyl serine, ⁇ reboylaspartic acid, ⁇ reboyl glutamic acid, ⁇ -Riboylphenylalanine, N-riboylmethionine, N-riboylnorleucine, N-riboylleucine, N-riboylcystine, N-riboylproline, N-riboylhydride xyproline, N-riboylhistidine, N-riboylhydroxytryptophan, N-ri 8.
  • the hair loss treatment agent according to 8 above, wherein the group power consisting of boiled-silamine and N lipoyllysine is also selected.
  • the active ingredient is N lipoyl-3-aminopropionic acid, N lipoyl-4-aminobutyric acid, N-riboyl-6-aminohexanoic acid, N-riboyl-4-transaminomethyl-1-cyclohexanecarboxylic acid, N-riboyl mono 8.
  • the hair loss treatment agent according to 8 above which is selected from the group consisting of 2-aminoethanesulfonic acid, N lipoylsulfuric acid and N lipoylanthral acid.
  • the active ingredient is N— (6,8 dimercaptootatanyl) glycine metal chelate, N- (6,8-dimercaptootatanyl) alanin metal chelate, N— (6,8-dimercaptootatanyl) ) Threonine metal chelate, N— (6,8-dimercaptootatanyl) serine metal chelate, N— (6,8-dimercaptootatanyl) aspartate metal chelate, N— (6,8— Dimercaptootatanyl) glutamic acid metal chelate, N— (6,8-dimercaptooctanoyl) ferroalanine metal chelate, N— (6,8-dimercaptootatanyl) methionine metal chelate, N— (6, 8—Dimercaptootatanyl) norleucine metal chelate, N— (6,8-dimercaptootatanyl)
  • the active ingredient is N— (6,8 dimercaptootatanyl) 3 aminopropionic acid metal chelate, N— (6,8 dimercaptootatanyl) -4-aminobutyric acid metal chelate, N— (6,8-dimercaptootathanyl) 6-aminohexanoic acid metal chelate, N— (6,8 dimercaptootathanyl) 4 transaminomethyl 1 cyclohexanecarboxylic acid metal chelate, N— ( 6, 8 Dimercaptootatanyl) 2 Aminoethanesulfonic acid Selected from the group consisting of metal chelates, N— (6,8-dimercaptootatanyl) sulfuric acid metal chelates and N— (6,8-dimercaptootatanyl) anthral acid metal chelates 9.
  • the hair loss treatment agent according to 9 above.
  • the active ingredient is N- (6,8-dimercaptootatanyl) aspatiruglycine metal chelate and N- (6,8-dimercaptootatanyl) threoglycine metal chelate 5.
  • the hair loss treatment agent according to 5 above, wherein a group strength that can be combined is selected.
  • the therapeutic agent for hair loss according to any one of 1 to 16, which is an external preparation for skin.
  • the hair loss treatment agent according to 17 above which is a hair styling agent or a hair wash.
  • the present invention also provides a method for preventing human hair loss and a therapeutic agent for hair loss comprising applying an effective amount of the active ingredient defined in 1 to 16 above to the human scalp surface. Also provided is the use of an active ingredient as defined in 1-16 above for the manufacture.
  • the hair loss treatment agent of the present invention exhibits an excellent therapeutic effect on human hair loss.
  • the present inventors reduced lipoic acid or lipoic acid amide with zinc and acetic acid (or hydrochloric acid), respectively, as a lipoic acid derivative, to obtain a 6,8-dimercaptooctanoic acid zinc chelate and 6, 8 —Dimercaptooctanoic acid zinc chelate compound was synthesized. Further, 6,8-dimercaptooctanoic acid ethyl ester dumbbell chelate was obtained by reducing lipoic acid ethyl ester in the same manner.
  • N— (6,8-dimercaptootatanyl) amine zinc chelate N— (6,8-dimercaptootatanyl) amino acid zinc chelate or N— (6,8-dimercaptoocta) (Neyl) peptide zinc chelate is prepared by first dissolving lipoic acid in chloroform or acetonitrile to couple amines, amino acids or peptides by mixed acid anhydride method using chloroethyl carbonate in the presence of triethylamine. N-riboylamines, N-riboylamino acids or N-riboyl peptides were obtained.
  • each zinc chelate compound when these are reduced with zinc and acetic acid (or hydrochloric acid) to obtain each zinc chelate compound, and further converted into an alkali salt, the free acid is dissolved or suspended in water and placed in water. After neutralizing with an acid-alkali solution, the solution is concentrated and then concentrated, and an alcohol is added, and the precipitated crystals are collected by filtration to obtain an alkali salt of each zinc chelate compound in high yield.
  • zinc and acetic acid or hydrochloric acid
  • metal of the metal chelate compound of the present invention zinc, cobalt, iron, germanium, and selenium are listed. Of these, zinc is preferable.
  • substituent R as the “lower alkyl”, those having 1 to 6 carbon atoms are preferred, those having 1 to 4 carbon atoms are more preferred, and those having 1 to 3 carbon atoms are particularly preferred. preferable.
  • Examples of the pharmacologically acceptable salt of the present compound include alkali metal salts such as sodium salt and potassium salt, and alkaline earth metal salts such as calcium salt and magnesium salt. Any salt can be appropriately used for the purpose of the present invention as long as it is a pharmacologically acceptable salt.
  • lipoic acid or lipoic acid derivative ie, 6,8-dimercaptooctanoic acid or its derivative
  • a force metal that is very unstable in air, such as zinc.
  • these compounds are excellent compounds that have a strong reducing action and radical inhibiting action, and that have no safety problems.
  • the use of the hair loss preventing agent of the present invention is simple and the effect is remarkable. That is, lipoic acid or a lipoic acid derivative may be applied to the scalp, for example, mixed with a hairdressing agent.
  • a hairdressing agent When observing the healing effect, the hair loss of the scalp, which had been removed by shampooing until now, was stopped by applying this compound, about 0.3% aqueous solution for about 1 month, and in particular, the case of remarkable cases Even if the hair near the coated area was pulled lightly, no hair loss was observed, and the hair roots were long and persistent, thus showing a healing effect.
  • the present compound for example, N- (6,8 dimercaptootatanyl) -L-histidine sodium.
  • the present compound can also be used in the form of a hair styling agent (hair artic, hair liquid, hair gel, aqueous spray, etc.) and a hair shampoo (shampoo, rinse, etc.).
  • a hair styling agent hair artic, hair liquid, hair gel, aqueous spray, etc.
  • a hair shampoo shampoo, rinse, etc.
  • the concentration of the present compound used is, for example, in the case of aqueous tonic and aqueous spray, usually 0.001 to 5 (wZv)%, preferably 0.01 to L 0 (wZv)%.
  • concentration of the present compound used is usually 0.001 to 5 (wZw)%, preferably from 0.01 to: L 0 (wZw)%, and also from shampoo, rinse, etc., preferably from 0.001 to 0.5 (wZv)%.
  • the therapeutic agent for hair loss of the present invention usually includes other ingredients used for hair nourishing agents, hair restoration agents, hair growth agents, as well as excipients, pigments, fragrances, ultraviolet absorbers, gelling agents, You may mix
  • the therapeutic agent for scalp hair loss of the present invention may contain one or more of the compounds according to the purpose and necessity as appropriate.
  • DL-a-lipoic acid 6.2g was dissolved in methanol 70mL, zinc powder 3.Og and 1N-hydrochloric acid 40mL were added, and it stirred at 50 degreeC for 1 hour. Next, zinc in the end reaction was filtered off, and the filtrate was concentrated under reduced pressure, and water was added to this, and the precipitated white crystals were collected by filtration. This was suspended in 150 mL of water, dissolved in 2N sodium hydroxide to a pH of about 9, the insoluble matter was filtered off, the filtrate was concentrated, ethanol was added to this, and the precipitated white crystals were collected by filtration. Recrystallization from water Z ethanol Nore force, mp. 300 ° C or more, 6. Og was obtained.
  • DL- ⁇ -lipoic acid 4.2 g and L histidine 3.4 g were used to obtain the desired compound, mp. 300 ° C. or more, and 5.8 g of white crystals.
  • DL— ⁇ -Lipoic acid 4.2 g and triethylamine 2.4 g were dissolved in 50 mL of acetonitrile and cooled to ⁇ 5 ° C. with stirring. To this, 2.4 g of chloroethyl carbonate was gradually added dropwise. Then, 1.5 g of isopropylamine dissolved in 30 mL of acetonitrile was rapidly added, and the mixture was further stirred for 30 minutes, returned to room temperature, and stirred for 1 hour. The solvent was distilled off under reduced pressure, water was added to the residue and the mixture was cooled.
  • DL-a-Lipoic acid 4.2g, triethylamine 2.4g and chloroethyl carbonate 2.4g were mixed in 50mL of acetonitrile with cooling to a mixed acid anhydride, and this was mixed with L lysine 3.lg, copper sulfate (pentahydrate) 5) and sodium hydroxide 2.
  • Example 1 Evaluation of testosterone 5 ⁇ reductase activity inhibitory action
  • Test sample 1 Lipoic acid (molecular weight 206. 33)
  • Test sample 2 N-a-riboylaminoethanesulfonic acid sodium salt (molecular weight 335. 45) (compound of Reference Example 12)
  • Test sample 3 6,8-dimercaptooctanoic acid 'zinc monoethanolamine salt (molecular weight 3 32. 79) (compound of reference example 1)
  • Test sample 4 N— (6,8-dimercaptootatanyl) —L histidine 'zinc sodium (molecular weight 430.84) (compound of reference example 14)
  • test step prepared with propylene glycol in a V-bottom test tube with a lid.
  • test sample 1 lipoic acid
  • test sample 2 N-a-riboylaminoethanesulfonic acid Na
  • test sample 3 (6,8-dimercaptooctanoic acid zinc monoethanol) (Ammine salt) showed a very strong testosterone 5 a-reductase activity inhibitory action.
  • test sample 4 N- (6,8-dimercaptootatanyl) L histidine zinc sodium
  • tested sample 4 N- (6,8-dimercaptootatanyl) L histidine zinc sodium
  • the hair loss treatment agent containing the compound of the present invention exhibits an excellent hair loss inhibitory effect and has high utility as a hair loss treatment agent.

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

La présente invention a pour objet un agent thérapeutique contre la perte des cheveux qui comprend un acide lipoïque ou un dérivé d'acide lipoïque de formule (1), ou un sel de qualité pharmaceutique de l’acide ou de son dérivé, au titre de principe actif : (1) où R représente un groupement OH, un groupement O-alkyle, une amine liée par l'azote, un acide aminé lié par l'azote ou un peptide lié par l'azote ; et A représente une liaison simple ou un métal M.
PCT/JP2006/307814 2005-04-28 2006-04-13 Agent thérapeutique contre la perte des cheveux WO2006117995A1 (fr)

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JP2005160423A JP2008174453A (ja) 2005-04-28 2005-04-28 頭皮脱毛治療剤
JP2005-160423 2005-04-28

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2114397A2 (fr) * 2006-12-20 2009-11-11 Medwell Laboratories Ltd. Nouveaux conjugués d'acides gras poly-insaturés avec des amines et utilisations thérapeutiques de ceux-ci
CN101786975A (zh) * 2009-01-22 2010-07-28 杭州民生药业有限公司 硫辛酰胺系列衍生物、制备方法及所述衍生物的制药用途
US7928067B2 (en) 2009-05-14 2011-04-19 Ischemix Llc Compositions and methods for treating ischemia and ischemia-reperfusion injury
CN102256970A (zh) * 2008-10-17 2011-11-23 因瓦斯科医疗有限公司 用于治疗肾活素-血管紧张素醛固酮系统(raas)相关性障碍的组合物以及方法
ITMI20102296A1 (it) * 2010-12-15 2012-06-16 Sigea Srl Uso di esteri lipoati di glicosamminoglicani in campo tricologico
US8815937B2 (en) 2010-11-18 2014-08-26 Ischemix Llc Lipoyl compounds and their use for treating ischemic injury
US10744115B2 (en) 2017-04-25 2020-08-18 Ischemix Llc Compositions and methods for treating traumatic brain injury

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JP5578997B2 (ja) * 2010-09-16 2014-08-27 国立大学法人 大分大学 がん化学療法誘発脱毛に対する抗脱毛用組成物
JP6453546B2 (ja) * 2014-02-19 2019-01-16 株式会社サロン・ド・リジュー 育毛用組成物
EA025550B1 (ru) * 2014-08-08 2017-01-30 Кыргызско-Российский Славянский Университет Способ лечения алопеции
US10632089B2 (en) * 2015-04-18 2020-04-28 Jo Cosmetics Co., Ltd. Tyrosinase activity inhibitor and external preparation for skin

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JP2003535115A (ja) * 2000-06-06 2003-11-25 ビーエーエスエフ アクチェンゲゼルシャフト 化粧品及び外皮用剤におけるリポ酸の（ｒ）−鏡像異性体の使用
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JPS62175417A (ja) * 1986-01-27 1987-08-01 Kanebo Ltd 養毛化粧料
JP2003535115A (ja) * 2000-06-06 2003-11-25 ビーエーエスエフ アクチェンゲゼルシャフト 化粧品及び外皮用剤におけるリポ酸の（ｒ）−鏡像異性体の使用
WO2002076935A1 (fr) * 2001-03-19 2002-10-03 Senju Pharmaceutical Co., Ltd. Nouveau derive de l'acide lipoique et son utilisation
WO2004024139A1 (fr) * 2002-09-13 2004-03-25 Oga Research, Incorporated Inactivateur de la melanine

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Title
NODA Y. ET AL.: "Antioxidant activities of novel .-lipoic acid derivatives: N-(6,8-dimercaptooctanoyl)-2-aminoethanesulfonate- and N-(6,8-dimercaptooctanoyl)-L-aspartate-zinc complex", RESEARCH COMMUNICATIONS IN MOLECULAR PATHOLOGY AND PHARMACOLOGY, vol. 113-114, 2003, pages 133 - 147, XP003003136 *

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2114397A2 (fr) * 2006-12-20 2009-11-11 Medwell Laboratories Ltd. Nouveaux conjugués d'acides gras poly-insaturés avec des amines et utilisations thérapeutiques de ceux-ci
EP2114397A4 (fr) * 2006-12-20 2013-06-12 Medwell Lab Ltd Nouveaux conjugués d'acides gras poly-insaturés avec des amines et utilisations thérapeutiques de ceux-ci
CN102256970A (zh) * 2008-10-17 2011-11-23 因瓦斯科医疗有限公司 用于治疗肾活素-血管紧张素醛固酮系统(raas)相关性障碍的组合物以及方法
EP2358707A4 (fr) * 2008-10-17 2012-08-22 Invasc Therapeutic Inc Compositions et procédés pour le traitement de troubles liés au système rénine-angiotensine-aldostérone (sraa)
CN101786975A (zh) * 2009-01-22 2010-07-28 杭州民生药业有限公司 硫辛酰胺系列衍生物、制备方法及所述衍生物的制药用途
CN101786975B (zh) * 2009-01-22 2013-11-13 杭州民生药业有限公司 硫辛酰胺系列衍生物、制备方法及所述衍生物的制药用途
US7928067B2 (en) 2009-05-14 2011-04-19 Ischemix Llc Compositions and methods for treating ischemia and ischemia-reperfusion injury
US9540417B2 (en) 2009-05-14 2017-01-10 Ischemix Llc Compositions and methods for treating ischemia and ischemia-reperfusion injury
US8772250B2 (en) 2009-05-14 2014-07-08 Ischemix, LLC Compositions and methods for treating ischemia and ischemia-reperfusion injury
US8772249B2 (en) 2009-05-14 2014-07-08 Ischemix, LLC Compositions and methods for treating ischemia and ischemia-reperfusion injury
US9359325B2 (en) 2010-11-18 2016-06-07 Ischemix Llc Lipoyl compounds and methods for treating ischemic injury
US8815937B2 (en) 2010-11-18 2014-08-26 Ischemix Llc Lipoyl compounds and their use for treating ischemic injury
ITMI20102296A1 (it) * 2010-12-15 2012-06-16 Sigea Srl Uso di esteri lipoati di glicosamminoglicani in campo tricologico
US9314418B2 (en) 2010-12-15 2016-04-19 Sigea S.R.L. Use of glycosaminoglycan lipoate esters in the trichology field
WO2012080223A1 (fr) 2010-12-15 2012-06-21 Sigea S.R.L. Utilisation d'esters de glycosaminoglycane lipoate dans le domaine de la tricologie
US9649269B2 (en) 2010-12-15 2017-05-16 Sigea S.R.L. Use of glycosaminoglycan lipoate esters in the trichology field
US10744115B2 (en) 2017-04-25 2020-08-18 Ischemix Llc Compositions and methods for treating traumatic brain injury
US11213509B2 (en) 2017-04-25 2022-01-04 Ischemix, LLC Compositions and methods for treating traumatic brain injury

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