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WO2003066573A1 - Sels metalliques de carnitines, supplements dietetiques contenant ces sels et necessaires dietetiques destines a traiter des troubles sexuels chez l'homme - Google Patents

Sels metalliques de carnitines, supplements dietetiques contenant ces sels et necessaires dietetiques destines a traiter des troubles sexuels chez l'homme Download PDF

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Publication number
WO2003066573A1
WO2003066573A1 PCT/IT2003/000050 IT0300050W WO03066573A1 WO 2003066573 A1 WO2003066573 A1 WO 2003066573A1 IT 0300050 W IT0300050 W IT 0300050W WO 03066573 A1 WO03066573 A1 WO 03066573A1
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WO
WIPO (PCT)
Prior art keywords
carnitine
acetyl
pharmacologically acceptable
zinc citrate
alc
Prior art date
Application number
PCT/IT2003/000050
Other languages
English (en)
Inventor
Aldo Fassi
Original Assignee
Aldo Fassi
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 Aldo Fassi filed Critical Aldo Fassi
Priority to AU2003209693A priority Critical patent/AU2003209693A1/en
Publication of WO2003066573A1 publication Critical patent/WO2003066573A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/76—Metal complexes of amino carboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/16—Inorganic salts, minerals or trace elements
    • A23L33/165—Complexes or chelates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds 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
    • C07C229/04—Compounds 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
    • C07C229/22—Compounds 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 the carbon skeleton being further substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/265—Citric acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to novel metal salts of carnitines, dietary/nutritional supplements, drugs and dietary kits containing said salts.
  • the present invention relates to the citrates of carnitines and zinc which are stable, non hygroscopic and water- soluble compounds. Therefore, these salts especially lend themselves to the production of both solid compositions suitable for oral administration and, owing to their water-solubility, to the formulation of liquid or fluid compositions, such as dermatological preparations, as described hereinbelow.
  • the present invention also relates to dietary/nutritional supplements and drugs comprising the aforesaid citrates which are effective in all those situations wherein zinc supplementation reverses or prevents the onset of the prejudicial effects brought about by zinc deficiency.
  • These dietary/nutritional supplements are especially, although not exclusively, suitable to enhance sperm motility and concentration in the seminal fluid of sub-fertile males and treat idiopathic astheno- spermia, owing to the joint action of carnitine, zinc and citrate.
  • the present invention further relates to dietary kits which contain doses of the aforesaid dietary supplements and doses of the aminoacid arginine. These kits are especially, even though not exclusively, effective for counteracting sexual disorders in male subjects.
  • non-hygroscopic reference is herein made to the ability endowed by certain carnitine salts (particularly, those of the present invention) when they occur as powders or granules, to withstand a relative humidity of at least 60%, at 25°C, for 24 hours, without giving rise to adverse phenomena of clotting, agglomeration or even deliquescence which result in loss of their flowability.
  • hygroscopic reference is herein made to the property shown by most carnitine salts (particularly by their “inner salts”) to undergo when they occur as powders or granules, significant alteration of their flowability due to their clotting, agglomeration or even deliquescence, following exposure to an assemblage of relative humidity lower than 50-60%, at 25°C, for 24 hours.
  • Carnitine citrates are already known. Carnitine citrate is disclosed in the UK patent 1,153,640 (Societe d'etudes de wall chimiques). L- carnitine and magnesium citrate and its utility in sports nutrition are disclosed in US patent 5,071,874 (Lonza Ltd.). Both these citrates are considerably hygroscopic.
  • the US patent 6,090,848 discloses the unexpected synergistic effect on sperm motility and concentration in the seminal fluid of sub- fertile males, and the therapeutical effect in the treatment of idiopathic asthenospermia, achieved by administering a combination composition of L-carnitine/acetyl L-carnitine wherein their molar ratio is preferably about 3:1, in contrast with the monopharmacological treatment.
  • the human body contains 2 to 3 grams of zinc and in males a relevant part thereof is found in testes.
  • the sign and symptoms of zinc deficiency include, among others, "delayed sexual maturation, hypogonadism and hypospermia” (The Merck Manual, loc. cit. page 53).
  • Zinc is an essential mineral for proper prostate gland function whose secretions comprise approximately 40% of seminal fluid wherein zinc levels are directly related to sperm motility and concentration.
  • Deficiency of dietary zinc reduces both sperm count and seminal plasma volume and results in delayed spermatozoal maturation and impaired sperm motility. Diet supplementation with zinc has been shown to reverse these phenomena.
  • the World Health Organization in pointing out the normal and pathological values of the various parameters characterizing the seminal fluid of human beings, has fixed to 52 ⁇ m/ejaculate (sperm total amount of a single ejaculation) the minimum amount of citric acid needed to warrant an effective sperm motility following one hour after ejaculation (http://www.il-st-acad-sci.org/androll.html). Citric acid concentrations lower than that previously indicated are generally liked to sub-fertility condition brought about by insufficient sperm motility and count.
  • Preferred dietary supplements because of the presence therein of salts which combine the efficacy of carnitine with that of zinc and citrate anion are those aimed at enhacing sperm motility and concentration and, consequently, improving the infertility conditions affecting sub- fertile male subjects.
  • compositions comprising salts of zinc and carnitines can be advantageously used as drugs.
  • R hydrogen or straight or branched-chain (C2-C5) alkanoyl are stable, non-hygroscopic and water-soluble compounds which fully comply with the aforesaid prerequisites.
  • Preferred alkanoyls are acetyl, propionyl, butyryl, valeryl and isovaleryl.
  • citrates are non-hygroscopic in view of the considerable hygroscopicity of the only two known citrates, i.e. L- carnitine citrate and L-carnitine magnesium citrate.
  • Example 2 The procedures of Example 1 were repeated by substituting 0.1 moles of propionyl L-carnitine inner salt for acetyl L-carnitine. The compound having the following formula was obtained with a yield of 95%:
  • Example 1 The procedures of Example 1 were repeated starting from 16.1 g (0.1 moles) of L-carnitine inner salt.
  • the present invention also relates to compositions which comprise as active ingredient one of the aforesaid carnitine zinc citrates and, optionally, at least one pharmacologically acceptable excipient.
  • compositions can present themselves as pharmaceuticals, OTC compositions, nutritional supplements and dietary supplements.
  • compositions according to the present invention can also comprise further nutritional or pharmacological active ingredients.
  • the dietary/nutritional supplements suitable for enhancing sperm motility and concentration may comprise further pharmacologically acceptable salts of L-carnitine and/or acetyl L-carnitine and/or propionyl L-carnitine.
  • compositions can also comprise fillers, binders, lubricants, mold release agents, flow-regulating agents, dispersing agents, colorants, flavoring agents and the like as it will be apparent to any expert in pharmaceutical technology or pharmacy.
  • the aforesaid carnitine and zinc citrates can be advantageously used, owing to their water-solubility, for manufacturing topically applicable, dermatological preparations, such as ointments, lotions and creams.
  • the water-soluble zinc salts have long since been known to be effective against a variety of viruses, particularly those which bring about skin disorders, such as e.g. the herpes simplex viruses, HSV-1 and HSV-2. Because of this activity, L-carnitine zinc citrate can be effectively compounded in the lubricants for the external genital organs disclosed in US patent 5,208,031 (which is incorporated herein by reference.
  • the orally administrable, solid forms comprise tablets, chewable tablets, pills, troches, lozenges, capsules, powders or granulates.
  • the presentation form can occur as sachets.
  • compositions of the present invention in unit dosage form, suitably contain the whole zinc's RDA, i.e. 12-15 mg, or a lower amount (from about 1/3 to about 1/2 of RDA) such as e.g. about 4-8 mg of zinc as carnitine zinc citrate for those individuals who stay on a multiple dose administration regimen.
  • RDA Recommended Dietary Allowance
  • the aforesaid dietary/nutritional supplements of the present invention can also suitably comprise a selenium compound (e.g. selenomethionine), vitamins (e.g. vitamin C, vitamin E, vitamin B6, vitamin B12 and folic acid), coenzymes (e.g. coenzyme Qio), ferulic acid and citric acid.
  • a selenium compound e.g. selenomethionine
  • vitamins e.g. vitamin C, vitamin E, vitamin B6, vitamin B12 and folic acid
  • coenzymes e.g. coenzyme Qio
  • ferulic acid and citric acid e.g. coenzyme Qio
  • compositions of the invention in unit dosage form also comprise about 20-35 ⁇ g/day of selenium (preferably as selenomethionine). For instance, 70 ⁇ g of selenomethionine contain 28 ⁇ g of selenium.
  • compositions for sachets may comprise suitable excipients such as fructose, citric acid, saccharin sodium, tonic water flavour, D-mannitol and colloidal silicon dioxide.
  • compositions for tablets and chewable tablets may comprise excipients such as mint essence, saccharin sodium, sorbitol solution, sorbitol, magnesium stearate, talc, pregelatinized corn starch, mannitol and saccharose.
  • excipients such as mint essence, saccharin sodium, sorbitol solution, sorbitol, magnesium stearate, talc, pregelatinized corn starch, mannitol and saccharose.
  • compositions for capsules can be entirely free of excipients, in view of the chemical inertness of the ingredients towards the gelatinous material the capsules are made of.
  • compositions for dietary supplements in unit dosage form are given hereinbelow, wherein all the carnitine salts are non-hygroscopic and, therefore, lend themselves to the production not only of sachets, but also tablets, chewable tablets, pills, troches, lozenges and capsules.
  • LC L-carnitine
  • ALC acetyl L-carnitine
  • the present invention finally relates to a dietary kit which comprises: a) at least one first container containing a dose of L-carnitine zinc citrate and a dose of a further pharmacologically acceptable salt of L-carnitine; and b) at least one second container containing a dose of arginine.
  • the first container further contains a pharmacologically acceptable salt of acetyl L-carnitine, the LC/ALC molar ratio ranging from 4:1 to 1:1.
  • the preferred LC/ALC molar ratio is about 3.
  • the kit comprises: al) at least one first container containing acetyl L-carnitine zinc citrate and a further pharmacologically acceptable salt of acetyl L-carnitine; and bl) at least one second container containing arginine.
  • Container al can further contain a pharmacologically acceptable salt of L-carnitine, the molar ratio LC/ALC ranging from 4:1 to 1:4.
  • the first container a) or al) can also contain a pharmacologically acceptable salt of propionyl L- carnitine (PLC), the molar ratio LC/ALC/PLC ranging from 4:1:0.5 to 1:4:2.
  • PLC propionyl L- carnitine
  • arginine-containing dietary supplements have become increasingly widespread because not only the nutritionally oriented doctors but also cardiologists and endocrinologists have ascertained the valuable therapeutic properties of this aminoacid.
  • arginine selectively lowers LDL cholesterol without reducing the beneficial HCL cholesterol and does so without producing unwanted side effects. It also promotes coronary micro-circulation and inhibits the formation of blood clots, a key etiological factor leading to heart attacks and strokes.
  • Arginine is a precursor/modulator of nitric oxide (NO). NO plays essential physiological roles which range from neurotransmission to vasodilation.
  • NO By relaxing arteries, NO can improve inadequate circulation-related conditions such as angina, intermittent claudication, hypertension and impaired brain circulation. NO is, moreover, the decisive factor in a man's ability to achieve and maintain an erection during sexual intercourse. Administration of 3 grams of arginine/day was reported to be effective in the treatment of erectile failure and impotence.
  • the users who particularly — although not exclusively — may benefit from the kit of the present invention are those male consumers who are in need of both improving their ability to achieve and maintain an erection during sexual intercourse and enhancing sperm motility and count in the seminal fluid.
  • the first container may contain any one of the preceding compositions 1-5, and the second container 1.0-2.0 g of arginine. It is advisable that the contents of a first container and the contents of a second container are ingested by the user substantially at the same time, twice-three times a day.
  • the arginine container also contains an antioxidant which can be selected from a broad spectrum of known antioxidants.
  • an antioxidant which can be selected from a broad spectrum of known antioxidants.
  • Preferred examples of antioxidants are coenzyme Qio and lipoic acid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Mycology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des citrates de zinc et de carnitines stables et non hygroscopiques qui se prêtent avantageusement à la préparation de compositions solides pouvant être administrées par voie orale et de compositions fluides à usage dermatologique. Des suppléments diététiques comprenant ces sels permettent d'améliorer efficacement la motilité et le nombre des spermatozoïdes chez des sujets hypofertiles.
PCT/IT2003/000050 2002-02-04 2003-02-03 Sels metalliques de carnitines, supplements dietetiques contenant ces sels et necessaires dietetiques destines a traiter des troubles sexuels chez l'homme WO2003066573A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003209693A AU2003209693A1 (en) 2002-02-04 2003-02-03 Metal salts of carnitines, dietary supplements containing same and dietary kits for counteracing sexual disorders in male subjects

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2002RM000055A ITRM20020055A1 (it) 2002-02-04 2002-02-04 Sali metallici di carnitine, integratori dietetici/nutritivi che li contengono e kit dietetici per contrastare disturbi sessuali in soggetti
ITRM2002A000055 2002-02-04

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WO (1) WO2003066573A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2884691A1 (fr) * 2005-04-21 2006-10-27 Formquest Ltd Complement alimentaire comprenant une combinaison d'agents antioxydants et d'agents energisants utile comme aide a la fertilite chez l'homme et chez la femme
US20110189152A1 (en) * 2010-02-02 2011-08-04 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Combination composition, comprising as active ingredients L-carnitine or propionyl L-carnitine, for the prevention or treatment of chronic venous insufficiency
US8415392B2 (en) 2002-04-09 2013-04-09 Sigma-Tau Industrie Farmaceutiche Riunite, S.P.A. Combined use of L-carnitine, acetyle L-carnitine and propionyl L-carnitine for the treatment of oligoasthenoteratospermia
CN106748732A (zh) * 2016-12-20 2017-05-31 湖北大学 一种柠檬酸锌铵的制备方法
CN109280005A (zh) * 2017-07-20 2019-01-29 辽宁科硕营养科技股份有限公司 一种复合柠檬酸锌盐、其制备方法、包含其的组合物及其用途
US20210347789A1 (en) * 2018-09-21 2021-11-11 Lae Ok PARK Zinc complex compound comprising citric acid and arginine ligand
WO2025037993A1 (fr) 2023-08-13 2025-02-20 Filip Majewski Forme posologique pour agents peptidiques

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* Cited by examiner, † Cited by third party
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US4602039A (en) * 1983-12-28 1986-07-22 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Salts of-carnitine and alkanoyl L-carnitines and process for preparing same
US5071874A (en) * 1989-06-14 1991-12-10 Lonza Ltd. L-carnitine magnesium citrate
EP0628308A1 (fr) * 1993-06-02 1994-12-14 AVANTGARDE S.p.A. Utilisation d'O-esters de L-carnitine avec des acides aromatiques
US5667791A (en) * 1996-05-31 1997-09-16 Thione International, Inc. X-ray induced skin damage protective composition
US5952379A (en) * 1996-05-31 1999-09-14 Sigma-Tau Industrie Farmaceutiche Stable, non-hygroscopic salts of L(-)carnitine and alkanoyl L(-)carnitines, a process for their preparation and solid, orally administrable compositions containing such salts
US5976568A (en) * 1997-02-21 1999-11-02 Medical Doctors' Research Institute, Inc. Modular system of dietary supplement compositions for optimizing health benefits and methods
US6271258B1 (en) * 1997-02-25 2001-08-07 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Process for the preparation of stable, non-hygroscopic salts of L(-)carnitine
US20010027214A1 (en) * 1997-04-08 2001-10-04 Nazareno Scafetta Solid compositions suitable for oral administration comprising an alkanoyl-l-carnitine magnesium citrate
WO2001082878A1 (fr) * 2000-05-02 2001-11-08 Perricone Nicholas V Traitement de lesions cutanees au moyen d'acetyl-carnitine et de phosphatidylcholine et/ou d'esters d'acide gras d'ascorbyle
WO2002058693A1 (fr) * 2001-01-23 2002-08-01 Aldo Fassi Sels metalliques de carnitines, utiles en tant que complements alimentaires/nutritionnels ou medicaments, et compositions contenant lesdits sels
US20020142052A1 (en) * 2000-12-22 2002-10-03 Trant Aileen Sontag Method and composition for improving male fertility health

Patent Citations (11)

* Cited by examiner, † Cited by third party
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US4602039A (en) * 1983-12-28 1986-07-22 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Salts of-carnitine and alkanoyl L-carnitines and process for preparing same
US5071874A (en) * 1989-06-14 1991-12-10 Lonza Ltd. L-carnitine magnesium citrate
EP0628308A1 (fr) * 1993-06-02 1994-12-14 AVANTGARDE S.p.A. Utilisation d'O-esters de L-carnitine avec des acides aromatiques
US5667791A (en) * 1996-05-31 1997-09-16 Thione International, Inc. X-ray induced skin damage protective composition
US5952379A (en) * 1996-05-31 1999-09-14 Sigma-Tau Industrie Farmaceutiche Stable, non-hygroscopic salts of L(-)carnitine and alkanoyl L(-)carnitines, a process for their preparation and solid, orally administrable compositions containing such salts
US5976568A (en) * 1997-02-21 1999-11-02 Medical Doctors' Research Institute, Inc. Modular system of dietary supplement compositions for optimizing health benefits and methods
US6271258B1 (en) * 1997-02-25 2001-08-07 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Process for the preparation of stable, non-hygroscopic salts of L(-)carnitine
US20010027214A1 (en) * 1997-04-08 2001-10-04 Nazareno Scafetta Solid compositions suitable for oral administration comprising an alkanoyl-l-carnitine magnesium citrate
WO2001082878A1 (fr) * 2000-05-02 2001-11-08 Perricone Nicholas V Traitement de lesions cutanees au moyen d'acetyl-carnitine et de phosphatidylcholine et/ou d'esters d'acide gras d'ascorbyle
US20020142052A1 (en) * 2000-12-22 2002-10-03 Trant Aileen Sontag Method and composition for improving male fertility health
WO2002058693A1 (fr) * 2001-01-23 2002-08-01 Aldo Fassi Sels metalliques de carnitines, utiles en tant que complements alimentaires/nutritionnels ou medicaments, et compositions contenant lesdits sels

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* Cited by examiner, † Cited by third party
Title
SINCLAIR S: "MALE INFERTILITY: NUTRITIONAL AND ENVIRONMENTAL CONSIDERATIONS", ALTERNATIVE MEDICINE REVIEW, THORNE RESEARCH INC., SANDPOINT,, US, vol. 5, no. 1, 2000, pages 28 - 38, XP008014042, ISSN: 1089-5159 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8415392B2 (en) 2002-04-09 2013-04-09 Sigma-Tau Industrie Farmaceutiche Riunite, S.P.A. Combined use of L-carnitine, acetyle L-carnitine and propionyl L-carnitine for the treatment of oligoasthenoteratospermia
FR2884691A1 (fr) * 2005-04-21 2006-10-27 Formquest Ltd Complement alimentaire comprenant une combinaison d'agents antioxydants et d'agents energisants utile comme aide a la fertilite chez l'homme et chez la femme
US20110189152A1 (en) * 2010-02-02 2011-08-04 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Combination composition, comprising as active ingredients L-carnitine or propionyl L-carnitine, for the prevention or treatment of chronic venous insufficiency
CN102791263A (zh) * 2010-02-02 2012-11-21 希格马托制药工业公司 用于预防或治疗慢性静脉功能不全的包含l-肉碱或丙酰基l-肉碱作为活性成分的联合组合物
US20130005670A1 (en) * 2010-02-02 2013-01-03 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. COMBINATION COMPOSITION, COMPRISING AS ACTIVE INGREDIENTS L-CARNITlNE OR PROPIONYL L-CARNITlNE, FOR THE PREVENTION OR TREATMENT OF CHRONIC VENOUS INSUFFICIENCY
US9457037B2 (en) 2010-02-02 2016-10-04 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Combination composition, comprising as active ingredients L-carnitine or propionyl L-carnitine, for the prevention or treatment of chronic venous insufficiency
CN102791263B (zh) * 2010-02-02 2016-10-12 希格马托制药工业公司 用于预防或治疗慢性静脉功能不全的包含l-肉碱或丙酰基l-肉碱作为活性成分的联合组合物
CN106748732A (zh) * 2016-12-20 2017-05-31 湖北大学 一种柠檬酸锌铵的制备方法
CN109280005A (zh) * 2017-07-20 2019-01-29 辽宁科硕营养科技股份有限公司 一种复合柠檬酸锌盐、其制备方法、包含其的组合物及其用途
US20210347789A1 (en) * 2018-09-21 2021-11-11 Lae Ok PARK Zinc complex compound comprising citric acid and arginine ligand
US11958872B2 (en) * 2018-09-21 2024-04-16 Lae Ok PARK Zinc complex compound comprising citric acid and arginine ligand
WO2025037993A1 (fr) 2023-08-13 2025-02-20 Filip Majewski Forme posologique pour agents peptidiques

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Publication number Publication date
AU2003209693A1 (en) 2003-09-02
ITRM20020055A1 (it) 2003-08-04
ITRM20020055A0 (it) 2002-02-04

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