FR2462M - - Google Patents

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Publication number
FR2462M
FR2462M FR911703A FR911703A FR2462M FR 2462 M FR2462 M FR 2462M FR 911703 A FR911703 A FR 911703A FR 911703 A FR911703 A FR 911703A FR 2462 M FR2462 M FR 2462M
Authority
FR
France
Prior art keywords
betaine
sodium
aspartate
aspartic acid
animals
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
FR911703A
Other languages
French (fr)
Inventor
Yvonne Thuillier
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.)
ROLLAND LAB A
Laboratoires Albert Rolland SA
Original Assignee
ROLLAND LAB A
Laboratoires Albert Rolland SA
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 ROLLAND LAB A, Laboratoires Albert Rolland SA filed Critical ROLLAND LAB A
Priority to FR911703A priority Critical patent/FR2462M/fr
Priority to BE638361A priority patent/BE638361A/en
Priority to GB39901/63A priority patent/GB1045969A/en
Application granted granted Critical
Publication of FR2462M publication Critical patent/FR2462M/fr
Expired legal-status Critical Current

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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
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • 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
    • C07C229/06—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 having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—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 having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/12—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 having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
    • 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
    • C07C229/24—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 having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Description

REPUBLIQUE FRANÇAISEFRENCH REPUBLIC

MINISTÈRE DE L'INDUSTRIEMINISTRY OF INDUSTRY

SERVICE de la PROPRIÉTÉ INDUSTRIELLEINDUSTRIAL PROPERTY SERVICE

BREVET SPÉCIAL DE MÉDICAMENTSPECIAL MEDICINAL PATENT

P.V. n° 911.703 Classification internationale :P.V. n ° 911.703 International Classification:

N° 2.462 M A 61 k — C 07 cN ° 2.462 M A 61 k - C 07 c

Nouveau médicament lipotrope. (Invention : Yvonne Thuillier.)New lipotropic drug. (Invention: Yvonne Thuillier.)

Société dite: LES LABORATOIRES ALBERT ROLLAND résidant en France (Seine).Company known as: LES LABORATOIRES ALBERT ROLLAND residing in France (Seine).

Demandé le 9 octobre 1962, à 15h 51m, à Paris.Requested on October 9, 1962, at 3:51 p.m., in Paris.

Délivré par arrêté du 13 avril 1964.Issued by decree of April 13, 1964.

(Bulletin officiel de la Propriété industrielle [B.S.M.], n° 20 de 1964.)(Official Bulletin of Industrial Property [B.S.M.], No. 20 of 1964.)

Le présent brevet spécial de médicament a pour objet le nouveau médicament constitué par le sel double de l'acide aspartique avec la bétaïne et le sodium ayant pour formule développée :The subject of this special patent for medicinal products is the new medicinal product consisting of the double salt of aspartic acid with betaine and sodium having the structural formula:

(CH3)3(CH3) 3

II

COO-N-CHa-COOHCOO-N-CHa-COOH

II

GH2GH2

II

CH-NHsCH-NHs

!!

COONaCOONa

Sa formule brute est : Cg^HivOeNa, son poids moléculaire de 272 et sa composition centésimale correspond à :Its crude formula is: Cg ^ HivOeNa, its molecular weight of 272 and its percentage composition corresponds to:

C = 39,70 %;C, 39.70%;

N -10,30%;N -10.30%;

H = 6,25%;H = 6.25%;

O = 35,30 %;O = 35.30%;

Na = 8,45 %.Na = 8.45%.

Le sel double de l'acide aspartique avec la bétaïne et le sodium ou aspartate de bétaïne et sodium est préparé en ajoutant à n molécules d'acide aspartique un peu moins de n molécules de soude. On obtient ainsi l'aspartate acide de sodium auquel on ajoute n molécules (ou un poids légèrement supérieur) de bétaïne. On concentre ensuite la solution à 600 ml par molécule d'acide aspartique mise en œuvre et ajoute cinq fois le volume d'acétone. Après agitation, on décante le précipité. On reprend ensuite une ou deux fois par l'acétone et on obtient des cristaux qui sont le sel double de l'acide aspartique avec la bétaïne et le sodium. Ces cristaux sont ensuite séchés à basse température.The double salt of aspartic acid with betaine and sodium or betaine and sodium aspartate is prepared by adding to n molecules of aspartic acid a little less than n molecules of soda. Sodium acid aspartate is thus obtained to which n molecules (or a slightly greater weight) of betaine are added. The solution is then concentrated to 600 ml per molecule of aspartic acid used and five times the volume of acetone added. After stirring, the precipitate is decanted. It is then taken up once or twice with acetone and crystals are obtained which are the double salt of aspartic acid with betaine and sodium. These crystals are then dried at low temperature.

Le corps obtenu se présente sous forme de cristaux blancs, hygroscopiques, contenant environ 15 % d'eau. Les cristaux sont insolubles dans l'acétone et très solubles dans l'eau. Le dosage d'azote total par la méthode de Kjeldahl révèle la présence de 2 molécules d'azote pour une molécule d'aspar-tate de bétaïne et sodium. Le pH de la solutionThe body obtained is in the form of white, hygroscopic crystals, containing about 15% water. The crystals are insoluble in acetone and very soluble in water. The determination of total nitrogen by the Kjeldahl method reveals the presence of 2 molecules of nitrogen for one molecule of betaine sodium aspartate. The pH of the solution

M/10 est de 5,04. Le titrage électrométrique dont les courbes sont représentées dans la figure ci-jointe met en évidence la fonction acide et aminé.M / 10 is 5.04. The electrometric titration, the curves of which are shown in the attached figure, demonstrates the acid and amino function.

L'étude pharmacologique sur des rats a montré une action lipotrope. La dite étude a été effectuée suivant le protocole d'expérimentation décrit ci-après :The pharmacological study in rats showed lipotropic action. The said study was carried out according to the experimental protocol described below:

1° Une série d'animaux témoins a été soumise à un régime hyperlipidique, hypercalorique et carencé en bétaïne pour provoquer une stéatose du foie;1 ° A series of control animals were subjected to a high fat, high calorie and betaine deficient diet to cause steatosis of the liver;

2° Une série a été soumise au même régime et recevait trois fois par semaine une injection sous-cutanée de 10 mg de l'aspartate de bétaïne et sodium. Cette série a été sacrifiée au bout d'un mois avec un sacrifice précoce de trois animaux (un chaque semaine) et examen histologique;2 ° A series was subjected to the same regimen and received three times a week a subcutaneous injection of 10 mg of betaine sodium aspartate. This series was sacrificed after one month with an early sacrifice of three animals (one each week) and histological examination;

3° Une troisième série a reçu le même régime et une injection sous-cutanée du même volume de solvant (1 ml). Les animaux ont été sacrifiés au bout d'un mois et ont fait l'objet d'un examen histologique;3 ° A third series received the same regime and a subcutaneous injection of the same volume of solvent (1 ml). The animals were sacrificed after one month and were subjected to histological examination;

4° Une quatrième série a été soumise au même régime et au bout de ce temps a reçu 10 mg de l'aspartate de bétaïne et sodium en injections sous-cutanées et les animaux ont été sacrifiés à des temps étagés pour en faire l'examen histologique.4 ° A fourth series was subjected to the same regime and at the end of this time received 10 mg of betaine and sodium aspartate in subcutaneous injections and the animals were sacrificed at staggered times for examination. histological.

On a pu constater l'effet préventif sur le lot n° 2 et curatif sur le lot n° 4 par rapport aux animaux témoins tous atteints d'infiltrations graisseuses importantes.The preventive effect on batch No. 2 and the curative effect on batch No. 4 compared with the control animals, all affected by significant fatty infiltrations, were observed.

On a procédé à l'étude biochimique afin de déterminer si la consommation aérobie d'oxygène et le dégagement de CO2 en anaérobiose par un homo-génat de foie de rat sont modifiés lorsqu'on ajoute au milieu de l'aspartate de bétaïne et sodium.The biochemical study was carried out to determine whether the aerobic oxygen uptake and the anaerobically released CO2 by a rat liver homogenate are modified when sodium betaine aspartate is added to the medium. .

On fait un homogénat du foie de rat mis à jeun vingt-quatre heures auparavant dans du saccharose M/4 refroidi. L'homogénat est réalisé par passage pendant une minute dans un broyeur Yirtis (40 000 t/mn). On l'amène ensuite à une concentration de 10 % avec du saccharose M/4.A homogenate is made from the fasting rat liver twenty-four hours previously in cooled M / 4 sucrose. The homogenate is produced by passing for one minute through a Yirtis mill (40,000 rpm). It is then brought to a concentration of 10% with M / 4 sucrose.

La consommation d'oxygène est mesurée dans un appareil de Warburg à température et à volumeOxygen consumption is measured in a Warburg apparatus at temperature and volume

65 2191 0 73 222 365 2191 0 73 222 3

Prix du fascicule : 2 francsPrice of the booklet: 2 francs

[2.462 M] —[2.462 M] -

constants par les différences de pression enregistrées sur des manomètres gradués.constant by the pressure differences recorded on graduated manometers.

Composition des fioles de WarburgComposition of Warburg vials

Fiole 1Vial 1

Fiole 2Vial 2

Cavité principaleMain cavity

0,1 ml tampon K+M 0,1 ml Cia Mg M/10 1,1 ml eau0.1 ml K + M buffer 0.1 ml Cia Mg M / 10 1.1 ml water

0,1 ml tampon K+ M 0,1 ml Cia Mg M/10 1 ml = 20 [x moles d'aspartate de bétaïne et sodium 0,1 ml eau0.1 ml K + M buffer 0.1 ml Cia Mg M / 10 1 ml = 20 [x moles of betaine sodium aspartate 0.1 ml water

Diverticule latéralLateral diverticulum

0,5 ml homogénat de foie.0.5 ml liver homogenate.

0,5 ml homogénat de foie.0.5 ml liver homogenate.

CentreCenter

0,2mlNaOH5N.0.2mlNaOH5N.

0,2 ml Na OH 5 N0.2 ml Na OH 5 N

Atmosphère de OaAtmosphere of Oa

Le diverticule est renversé après dix minutes pour équilibrer la température.The diverticulum is inverted after ten minutes to balance the temperature.

La quantité d'oxygène QO2 consommée en quarante-cinq minutes, avec déduction du substrat endogène, est déterminée par la différence des consommations mesurées dans les deux fioles. QO2 = 11,6 [il.The quantity of oxygen QO2 consumed in forty-five minutes, with deduction of the endogenous substrate, is determined by the difference in consumption measured in the two flasks. QO2 = 11.6 [il.

La même expérience a été reprise en présence de 5 [x moles de succinate qui est un catalyseur de respiration. On a alors obtenu un QO2 pour quarante-cinq minutes (substrat endogène déduit) de 11 [il.The same experiment was repeated in the presence of 5 µmoles of succinate which is a respiration catalyst. A QO2 for forty-five minutes (deduced endogenous substrate) of 11 µl was then obtained.

Cette expérience montre que l'aspartate de bétaïne et sodium catalyse faiblement la respiration du foie dans les mêmes proportions, que le milieu contienne ou non du succinate.This experiment shows that betaine sodium aspartate weakly catalyzes liver respiration in the same proportions, whether or not the medium contains succinate.

Les essais de toxicité ont permis de conclure à l'absence totale de toxicité aiguë ou chronique. Ils ont été rédisés successivement sur des lots d'animaux divers : souris, rats Wistar, cobayes, lapins. Par injection intra-péritonéale à doses croissantes de 100, 300, 500 et 1 000 mg/kg on n'a constaté aucune mortalité. Le produit injecté par voie intraveineuse, même à une dose de 300 mg/kg dans 5 ml de solvant, a été bien toléré.The toxicity tests made it possible to conclude that there was no acute or chronic toxicity. They were written successively on batches of various animals: mice, Wistar rats, guinea pigs, rabbits. By intraperitoneal injection in increasing doses of 100, 300, 500 and 1000 mg / kg no mortality was observed. The product injected intravenously, even at a dose of 300 mg / kg in 5 ml of solvent, was well tolerated.

Les essais de toxicité chronique ont été rédisés sur des rats Wistar, chaque lot recevant quotidiennement 100 mg/kg de solution d'aspartate de bétaïne et sodium. Ces doses ont été parfaitement tolérées et n'ont amené aucune lésion chez les animaux traités.Chronic toxicity tests were performed on Wistar rats, each batch receiving 100 mg / kg of betaine sodium aspartate solution daily. These doses were perfectly tolerated and produced no lesions in the treated animals.

Ces diverses propriétés font de l'aspartate de bétaïne et sodium un agent thérapeutique intéressant en raison de son action lipotrope. Il protège la cellule hépatique contre l'intoxication graisseuse et régularise le métabolisme des lipides.These various properties make betaine sodium aspartate an interesting therapeutic agent because of its lipotropic action. It protects the liver cell against fatty poisoning and regulates lipid metabolism.

Il est indiqué notamment dans tous les cas d'insuffisance hépatique.It is particularly indicated in all cases of hepatic insufficiency.

Le nouveau médicament peut être administré sous toutes les formes usuelles telles que poudres, comprimés, granulés, cachets, sirops, solutés buvables et injectables, suppositoires.The new medicament can be administered in all the usual forms such as powders, tablets, granules, cachets, syrups, drinkable and injectable solutions, suppositories.

Dans les différentes formules l'aspartate de bétaïne et sodium peut se trouver comme seul principe actif ou être associé à d'autres principes actifs.In the various formulas, betaine sodium aspartate can be found as the only active principle or be combined with other active principles.

A titre d'exemple on peut citer, dans le cas d'une insuffisance hépatique, le traitement avec une posologie de 2 à 3 comprimés par jour de formule :By way of example, there may be mentioned, in the case of hepatic insufficiency, treatment with a dosage of 2 to 3 tablets per day of the formula:

Aspartate de bétaïne et sodium 0,250 gBetaine sodium aspartate 0.250 g

Excipient, q.s.p 0,350 gExcipient, q.s.p 0.350 g

BÉSUMÉBESUMED

Le présent brevet spécial de médicament a pour objet :The subject of this special medicinal product is:

1° Le médicament constitué par le sel double de l'acide aspartique avec la bétaïne et le sodium de formule développée :1 ° The drug consisting of the double salt of aspartic acid with betaine and sodium of structural formula:

(CH3)3(CH3) 3

II

COO-N-CH2-COOH ICOO-N-CH2-COOH I

CH2 ICH2 I

CH-NH2 ICH-NH2 I

COONaCOONa

2° Les médicaments contenant, parmi leurs principes actifs, le sel double de l'acide aspartique avec la bétaïne et le sodium;2 ° Medicines containing, among their active principles, the double salt of aspartic acid with betaine and sodium;

3° Les médicaments selon 1° et 2° ci-dessus présentés sous forme de poudres, comprimés, granulés, cachets, sirops, solutés buvables et injectables ou suppositoires.3 ° Medicines according to 1 ° and 2 ° above presented in the form of powders, tablets, granules, cachets, syrups, drinkable and injectable solutions or suppositories.

Société dite :Company known as:

LES LABORATOIRES ALBERT ROLLAND Par procuration :ALBERT ROLLAND LABORATORIES By proxy:

A. LEMO NOTERA. LEMO NOTE

AVIS DOCUMENTAIRE SUR LA NOUVEAUTÉDOCUMENTARY NOTICE ON THE NEW FEATURE

Documents susceptibles de porter atteinte à la nouveauté du médicament : néant.Documents likely to affect the novelty of the medicinal product: none.

Documents illustrant l'état de la technique en la matière :Documents illustrating the state of the art in this area:

— Brevet français n° 1.176.116.- French patent n ° 1,176,116.

FR911703A 1962-10-09 1962-10-09 Expired FR2462M (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FR911703A FR2462M (en) 1962-10-09 1962-10-09
BE638361A BE638361A (en) 1962-10-09 1963-10-08 New lipotropic drug.
GB39901/63A GB1045969A (en) 1962-10-09 1963-10-09 Sodium betaine aspartate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR911703A FR2462M (en) 1962-10-09 1962-10-09

Publications (1)

Publication Number Publication Date
FR2462M true FR2462M (en) 1964-05-15

Family

ID=8788336

Family Applications (1)

Application Number Title Priority Date Filing Date
FR911703A Expired FR2462M (en) 1962-10-09 1962-10-09

Country Status (3)

Country Link
BE (1) BE638361A (en)
FR (1) FR2462M (en)
GB (1) GB1045969A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19956772A1 (en) * 1999-11-25 2001-06-07 Basf Ag Use of y-butyrobetaine salts for the preparation of preparations for human and animal nutrition
CN111517970A (en) * 2020-05-22 2020-08-11 安徽安力肽生物科技有限公司 Preparation method of L-aspartic acid sodium salt monohydrate

Also Published As

Publication number Publication date
GB1045969A (en) 1966-10-19
BE638361A (en) 1964-02-03

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