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WO2003032751A1 - Sels metalliques d'alcanoyles l-carnitine, supplements dietetiques les contenant, et supplements dietetiques - Google Patents

Sels metalliques d'alcanoyles l-carnitine, supplements dietetiques les contenant, et supplements dietetiques Download PDF

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Publication number
WO2003032751A1
WO2003032751A1 PCT/IT2002/000639 IT0200639W WO03032751A1 WO 2003032751 A1 WO2003032751 A1 WO 2003032751A1 IT 0200639 W IT0200639 W IT 0200639W WO 03032751 A1 WO03032751 A1 WO 03032751A1
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WIPO (PCT)
Prior art keywords
carnitine
alc
acetyl
acceptable salt
pharmacologically acceptable
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Ceased
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PCT/IT2002/000639
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English (en)
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Aldo Fassi
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    • 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
    • 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
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino 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
    • A61K31/185—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
    • A61K31/28—Compounds containing heavy metals
    • A61K31/315—Zinc compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/30—Zinc; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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 non-hygroscopic and water- soluble metal salts of lower alkanoyl L-carnitines, dietary/nutritional supplements and drugs containing same and dietary kits containing said supplements.
  • the present invention relates to the chlorides of acetyl-L-carnitine and zinc, propionyl L-carnitine and zinc, and isovaleryl L-carnitine 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.
  • acetyl, propionyl and isovaleryl groups shall be collectively referred to as "lower alkanoyls”.
  • the present invention also relates to dietary/nutritional supplements and drugs comprising the aforesaid salts, 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 asthenospermia.
  • 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 lower alkanoyl L-carnitine salts, 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 of lower alkanoyl L-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 environment of relative humidity lower than 50-60%, at 25°C, for 24 hours.
  • administration forms such as tablets and capsules represent the preferred presentation forms inasmuch as they make it particularly easy for users to take the active ingredient and comply with optimal dosage regimens.
  • the problem of L-carnitine and alkanoyl L-carnitine inner salts hygroscopicity has been satisfactorily solved by converting these inner salts into salts of pharmacologically acceptable acids, based on the assumption that such salts maintain the same therapeutical/nutritional activities of the inner salts and do not exhibit unwanted toxic or side effects.
  • Zinc deficiencies may bring about multiform disturbances.
  • 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.
  • Dietary supplements wherein zinc is particularly useful and which are, therefore, particularly preferred, are those aimed at enhancing sperm motility and concentration and, consequently, improving the infertility conditions affecting sub-fertile male subjects.
  • the aforesaid solid compositions can be prepared with conventional apparatuses and avoiding to resort to dehumidified facilities. This object can only be achieved if the aforesaid salts are stable and non- hygroscopic.
  • compositions comprising salts of zinc and alkanoyl L-carnitines can be advantageously used as drugs.
  • alkanoyl L-carnitines and zinc chlorides having formula
  • R is acetyl, propionyl or isovaleryl are stable, non hygroscopic and water-soluble compounds which fully comply with the aforesaid prerequisites.
  • the following non-limiting example shows the preparation of a compound according to the present invention and its main physico- chemical characteristics.
  • compositions which comprise as active ingredient at least one of the aforesaid chlorides and, optionally, a 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.
  • Particularly preferred pharmacologically acceptable salts of L-carnitine are the acid fumarate, the tartrate and the galactarate.
  • Those of acetyl L-carnitine are the chloride, the acid fumarate and galactarate.
  • 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 alkanoyl L-carnitine and zinc chlorides 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 HSN-2.
  • the aforesaid chlorides 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. In case of 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 acetyl L-carnitine and zinc chloride 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 Be, vitamin B12 and folic acid), coenzymes (e.g. coenzyme Q10) and ferulic acid.
  • a selenium compound e.g. selenomethionine
  • vitamins e.g. vitamin C, vitamin E, vitamin Be, vitamin B12 and folic acid
  • coenzymes e.g. coenzyme Q10
  • ferulic acid e.g. coenzyme Q10
  • compositions of the invention in unit dosage form also comprise about 20-35 ⁇ g/day of selenium (preferably as selenomethionine).
  • selenium preferably as selenomethionine
  • 70 ⁇ g of selenomethionine contain 28 ⁇ g of selenium.
  • 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 comprising the capsules.
  • 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.
  • the L-carnitine/acetyl L-carnitine molar ratio is from 4:1 to 1:1, preferably about 3.
  • LC L-carnitine
  • ALC acetyl L-carnitine
  • ALC:Zn:Cl2 acetyl L-carnitine and zinc chloride.
  • compositions further comprising at least one of t thhee f fooUlloowwiinn.g? i innggrreeddiieennttss::
  • the present invention finally relates to a dietary kit which comprises:
  • the first container further contains a pharmacologically acceptable salt of L- carnitine, the LC/ALC molar ratio ranging from 4:1 to 1:1.
  • the preferred LC/ALC molar ratio is about 3.
  • 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 argine/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 consumer 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.
  • antioxidants are coenzyme Q 10 and lipoic acid.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Inorganic Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des chlorures d'alcanoyles inférieurs L-carnitine et de zinc. L'invention se rapporte également à des compositions contenant lesdits sels, qui sont particulièrement utiles pour améliorer la motilité et le nombre des spermatozoïdes chez les sujets stériles.
PCT/IT2002/000639 2001-10-18 2002-10-08 Sels metalliques d'alcanoyles l-carnitine, supplements dietetiques les contenant, et supplements dietetiques Ceased WO2003032751A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2001RM000621A ITRM20010621A1 (it) 2001-10-18 2001-10-18 Sali metallici non igroscopici e idrosolubili di alcanoil l-carnitine, integratori dietetici che li contengono e kit dietetici, per contrast
ITRM01A000621 2001-10-18

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WO2003032751A1 true WO2003032751A1 (fr) 2003-04-24

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IT (1) ITRM20010621A1 (fr)
WO (1) WO2003032751A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1754478A1 (fr) 2005-08-04 2007-02-21 Extarma AG Formulation solide contenant un donneur d'oxyde nitrique (no) et un ditholane pour améliorer la fonction sexuelle
WO2007087667A3 (fr) * 2006-02-03 2008-02-28 Fapa Vital Anstalt Préparation combinée destinée à améliorer la qualité du sperme
EP2135621A1 (fr) * 2008-06-18 2009-12-23 Roberto Fasani Formulations combinées pour le traitement de l'infertilité masculine
ES2333842A1 (es) * 2009-11-30 2010-03-01 Laboratorios Q Pharma S.L. Composicion farmaceutica destinada a mejorar la calidad del esperma.
US8003652B2 (en) * 2004-11-11 2011-08-23 Sigma-Tau Industrie Farmaceutiche Riunite, S.P.A. Use of acetyl L-carnitine in combination with propionyl L-carnitine and Sildenafil for the treatment of erectile dysfunction
WO2018039297A1 (fr) * 2016-08-26 2018-03-01 Dabdoub Atif Complément alimentaire macro/micronutritionnel pour patients subissant une dialyse rénale
RU2686334C2 (ru) * 2017-08-31 2019-04-25 Общество с ограниченной ответственностью "ЦитоНИР" (ООО "ЦитоНИР") Ректальное лекарственное средство коррекции нарушений сперматогенеза при мужской инфертильности
JP2019532098A (ja) * 2016-08-26 2019-11-07 ダブドゥブ, アティフDABDOUB, Atif 腎臓透析を受けている患者のための食餌性多量／微量栄養補給剤

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999027925A1 (fr) * 1997-12-01 1999-06-10 Sigma-Tau Healthscience S.P.A. Compositions et procedes pour accroitre la concentration et/ou la mobilite des spermatozoides humains

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999027925A1 (fr) * 1997-12-01 1999-06-10 Sigma-Tau Healthscience S.P.A. Compositions et procedes pour accroitre la concentration et/ou la mobilite des spermatozoides humains

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SINCLAIR S.: "MALE INFERTILITY: NUTRITIONAL AND ENVIRONMENTAL CONSIDERATIONS", ALTERN. MED. REV., vol. 5, no. 1, 2000, pages 28 - 38, XP008014042 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8003652B2 (en) * 2004-11-11 2011-08-23 Sigma-Tau Industrie Farmaceutiche Riunite, S.P.A. Use of acetyl L-carnitine in combination with propionyl L-carnitine and Sildenafil for the treatment of erectile dysfunction
WO2007017191A3 (fr) * 2005-08-04 2007-05-24 Extarma Ag Compositions contenant un donneur de no et un dithiolane, et leur utilisation pour ameliorer la fonction sexuelle
US9107889B2 (en) 2005-08-04 2015-08-18 Encrypta Gmbh Compositions comprising an NO donor and a dithiolane and their use for improvement of sexual function
CN102670591B (zh) * 2005-08-04 2014-08-06 英柯瑞普塔有限公司 包含一氧化氮供体和二硫戊环的组合物及其在制备性功能改善的药物中的用途
CN101237862B (zh) * 2005-08-04 2012-03-21 英柯瑞普塔有限公司 包含一氧化氮供体和二硫戊环的组合物及其在制备性功能改善的药物中的用途
EP1754478A1 (fr) 2005-08-04 2007-02-21 Extarma AG Formulation solide contenant un donneur d'oxyde nitrique (no) et un ditholane pour améliorer la fonction sexuelle
RU2423120C2 (ru) * 2005-08-04 2011-07-10 Энкрипта гмбХ Композиции, содержащие донор no и дитиолан, и их применение для улучшения сексуальной функции
EA015422B1 (ru) * 2006-02-03 2011-08-30 Фапа Витал Анштальт Комбинированный препарат для улучшения качества сперматозоидов
WO2007087667A3 (fr) * 2006-02-03 2008-02-28 Fapa Vital Anstalt Préparation combinée destinée à améliorer la qualité du sperme
US9623042B2 (en) 2006-02-03 2017-04-18 Fapa Vital Anstalt Combination preparation for improving sperm quality
EP2502635A1 (fr) * 2008-06-18 2012-09-26 Roberto Fasani Formulations combinées pour le traitement de la stérilité masculine
EP2135621A1 (fr) * 2008-06-18 2009-12-23 Roberto Fasani Formulations combinées pour le traitement de l'infertilité masculine
ES2333842B1 (es) * 2009-11-30 2011-02-10 Laboratorios Q Pharma S.L. Composicion farmaceutica destinada a mejorar la calidad del esperma.
ES2333842A1 (es) * 2009-11-30 2010-03-01 Laboratorios Q Pharma S.L. Composicion farmaceutica destinada a mejorar la calidad del esperma.
WO2018039297A1 (fr) * 2016-08-26 2018-03-01 Dabdoub Atif Complément alimentaire macro/micronutritionnel pour patients subissant une dialyse rénale
JP2019532098A (ja) * 2016-08-26 2019-11-07 ダブドゥブ, アティフDABDOUB, Atif 腎臓透析を受けている患者のための食餌性多量／微量栄養補給剤
US11077085B2 (en) 2016-08-26 2021-08-03 Atif Dabdoub Dietary macro/micronutritional supplement for patients undergoing kidney dialysis
JP7012724B2 (ja) 2016-08-26 2022-02-14 ダブドゥブ，アティフ 腎臓透析を受けている患者のための食餌性多量／微量栄養補給剤
RU2686334C2 (ru) * 2017-08-31 2019-04-25 Общество с ограниченной ответственностью "ЦитоНИР" (ООО "ЦитоНИР") Ректальное лекарственное средство коррекции нарушений сперматогенеза при мужской инфертильности

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Publication number Publication date
ITRM20010621A1 (it) 2003-04-18
ITRM20010621A0 (it) 2001-10-18

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