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DE2902160A1 - Medicaments for treating lipid metabolism disorders - contg. unsatd. aldehyde cpds., 8-hexadecenoic acid, or 2-hydroxy-8-16-tetracosa:dien-oic acid - Google Patents

Medicaments for treating lipid metabolism disorders - contg. unsatd. aldehyde cpds., 8-hexadecenoic acid, or 2-hydroxy-8-16-tetracosa:dien-oic acid

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DE2902160A1
DE2902160A1 DE19792902160 DE2902160A DE2902160A1 DE 2902160 A1 DE2902160 A1 DE 2902160A1 DE 19792902160 DE19792902160 DE 19792902160 DE 2902160 A DE2902160 A DE 2902160A DE 2902160 A1 DE2902160 A1 DE 2902160A1
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DE2902160C2 (en
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Wilhelm Dr Med Hoerrmann
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    • 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
    • A61K31/11—Aldehydes
    • 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
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C47/263—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • 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
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups

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

Abstract

New medicaments contain as active substance >=1 straight-chain, unsatd. 12-24C aldehyde or pharmaceutically acceptable deriv., opt. together with usual carriers and/or adjuvants. Alternative new medicaments contain as active substance 8-hexadecenoic acid (I) and/or 2-hydroxy-8,16-tetracosadienoic acid (II) or their pharmaceutically acceptable deriv., opt. together with usual carriers and/or adjuvants. The following unsatd. aldehydes and their optical and geometric isomers are new: O=CH-(CH2)4CH=CH(CH2)4-CH3;o=CH-(CH2)6CH=CH(CH2)6CH3; O=CH-(CH2)4CH=CH(CH2)4CH=CH(CH2)4CH3; and O=CH-CHOH-(CH2)5CH=CH(CH2)6CH=CH(CH2)6CH3. Also new are 2-hydroxy-8,16-tetracosadienoic acid and its optical and geometric isomers. Medicaments are of use in treatment of lipid metabolism disorders such as atherosclerosis (in which a deficiency of plasmalogens is observed) and multiple sclerosis. The effect of the medicaments in atherosclerosis is attributed to the replacement of deficient lipids, while the effect in multiple sclerosis is attributed to replacement of similar but not identical lipids.

Description

Langkettige Aldehyde oder KarbonsäurenLong chain aldehydes or carboxylic acids

enthaltendes Arzneimittel Die Erfindung betrifft-ein Arzneimittel, das als Wirksubstanz mindestens einen gradkettigen ungesättigten Aldehyd mit 12 bis 24 C-Atomen, bevorzugt diejenigen mit gerader Anzahl an C-Atomen, insbesondere 6-n-Dodecenaldehyd, 8-n-Hexadecenaldehyd, 6, 12-n-Octadecadienaldehyd und/oder 8, 16-n-Tetracosadien-2-hydroxyaldehyd oder dessen pharmazeutisch annehmbares Derivat, ggf. zusammen mit üblichen Trägern und/oder Hilfsmitteln, enthält.containing medicinal product The invention relates to a Medicinal product that has at least one straight-chain unsaturated aldehyde as its active substance with 12 to 24 carbon atoms, preferably those with an even number of carbon atoms, in particular 6-n-dodecenaldehyde, 8-n-hexadecenaldehyde, 6, 12-n-octadecadienaldehyde and / or 8, 16-n-tetracosadiene-2-hydroxyaldehyde or its pharmaceutically acceptable derivative, possibly together with customary carriers and / or auxiliaries.

Die Erfindung betrifft ferner ein Arzneimittel, das als Wirksubstanz 8-n-Hexadecensäure und/oder 8,16-n-Tetracosadien-2-Hydro-xysäure oder ihre pharmazeutisch annehmbaren Derivate, ggf. zusammen mit üblichen Trägern und/oder Hilfsmitteln, enthält.The invention also relates to a medicament which is used as an active substance 8-n-hexadecenoic acid and / or 8,16-n-tetracosadiene-2-hydroxy acid or their pharmaceuticals acceptable derivatives, if necessary together with customary carriers and / or auxiliaries, contains.

Die Erfindung betrifft weiterhin geradkettige, ungesättigte Aldehyde der Formel und ihre optischen und geometrischen Isomeren sowie 8, 16-n-Tetracosadien-2-hydroxysäure und ihre optischen und geometrischen Isomeren.The invention also relates to straight-chain, unsaturated aldehydes of the formula and its optical and geometric isomers and 8, 16-n-tetracosadiene-2-hydroxy acid and its optical and geometric isomers.

Untersuchungen über Fettstoffwechselstörungen, die in großer ZahUdurchgeführt wurden und werden, richteten sich zumeist auf Cholesterin und Triglyceride, während die fettaldehydhaltigen Lipide, auch als Plasmalogene bezeichnet, bisher wenig Beachtung fanden. Es ist allerdings bekannt (vgl.Studies on lipid metabolism disorders, which are carried out in large numbers were, and are, focused mostly on cholesterol and triglycerides while the fatty aldehyde-containing lipids, also known as plasmalogens, have received little attention so far found. However, it is known (cf.

Journal of Gerontology, Bd. 13, 430-434 (1964)), daß der Gehalt an Plasmalogen in atherosklerotischem Gewebe signifikant niedriger ist als in normalem Gewebe. Außer bei der Arteriosklerose liegen Fettstoffwechselstörungen auch bei anderen schweren Erkrankungen, wie z.B. der multiplen Sklerose vor.Journal of Gerontology, Vol. 13, 430-434 (1964)) that the content of Plasmalogen in atherosclerotic tissue is significantly lower than in normal Tissue. Apart from arteriosclerosis, disorders of the lipid metabolism are also involved other serious illnesses, such as multiple sclerosis.

Der Ausdruck "Arteriosklerose" bezeichnet die Vermehrung von Binde- und Muskelgewebe in den Arterien, während der häufig synonym gebrauchte zu chte Ausdruck "Therosklerose" auf die Ablagerung fettiger Substanzen in den Gefäßwänden hinweist. Eine Arteriosklerose braucht anfänglich jedoch keineswegs mit .einer Sklerose oder Atheromatose in den Blutgefäßen einherzugehen. Tatsächlich Ist nämlich die Bildung von Spalten und Hohlräumen vor allem in der Tunica Intima als die primäre und wesentliche Veränderung der Arteriosklerose anzusehen.The term "arteriosclerosis" refers to the increase in connective tissue and muscle tissue in the arteries, while often used interchangeably Term "therosclerosis" on the deposition of fatty substances in the vessel walls indicates. At first, however, atherosclerosis does not need to be accompanied by sclerosis or atheromatosis in the blood vessels. In fact, it is Formation of crevices and cavities in particular in the tunica intima to be regarded as the primary and major change in arteriosclerosis.

In den akuten Fällen werden diese Spalten und Hohlräume durch Ödeme, in den chronischen Fällen durch Ablagerung von fettigen Substanzen, wie Cholesterin, aufgetrieben, was zur Einengung des Gefäßlumens und weiteren degenerativen Prozessen, wie Sklerose, Calcinose und sogar Ulceration führt. Greift der Intimaprozeß auf das Endothel über, kommt es zur arteriellen Thrombose.In acute cases, these crevices and cavities are caused by edema, in chronic cases due to the deposition of fatty substances such as cholesterol, distended, which leads to the narrowing of the vascular lumen and further degenerative processes, such as sclerosis, calcinosis and even ulceration. The intimal process takes up over the endothelium, arterial thrombosis occurs.

Dagegen geht die multiple Sklerose in charakteristischer Weise mit einer Zerstörung der Protein-Lipid-Schichten der Markscheiden im Zentralen Nervensystem einher.On the other hand, multiple sclerosis goes along in a characteristic way a destruction of the protein-lipid layers of the medullary sheaths in the central nervous system hand in hand.

Obige Erkrankungen und generell solche, die mit Störungen des Fettstoffwechsels, insbesondere der Plasmalogene, verlaufen, können bisher weder zuverlässig geheilt noch zuverlässig in ihrem progressiven Verlauf aufgehalten werden.The above diseases and in general those with disorders of the lipid metabolism, in particular the plasma genes, run, can neither be reliably cured up to now can still reliably be stopped in their progressive course.

Der Erfindung liegt daher die Aufgabe zugrunde, ein Arzneimittel zur Verfügung zu stellen, das die krankhaften Erscheinungsbilder von Fettstoffwechselstörungen, wie sie den genannten Krankheiten zugrundeliegen oder mit ihnen einhergehen, mildern ode heilen kann.The invention is therefore based on the object of a medicament for To provide that the pathological manifestations of lipid metabolism disorders, how they underlie or go hand in hand with the diseases mentioned or can heal.

Diese Aufgabe wird durch ein Arzneimittel der eingangs genannten Art gelöst.This task is achieved by a drug of the type mentioned at the beginning solved.

Ohne die Erfindung ef bestimmte Wirkmechanismen beschränken zu wollen, wird angenommen, daß die günstige Wirkung der erfindungsgemäßen Arzneimittel bei Arteriosklerose auf der Verhinderung bzw. Verminderung der Bildung von Spalten und Hohlräumen, vor allem in der Tunica Intima, beruht. Die vorgeschIagenen langkettigen Aldehyde und Karbonsäuren beheben also einen Mangel im erkrankten Organismus (quantitative Substitution).Without wanting to restrict the invention ef certain mechanisms of action, it is believed that the beneficial effect of the drugs according to the invention Atherosclerosis on the prevention or reduction of the formation of crevices and Cavities, especially in the tunica intima. The proposed long-chain Aldehydes and carboxylic acids thus remedy a deficiency in the diseased organism (quantitative Substitution).

Dagegen gleichen sie bei der Multiplen Sklerose eine molekulare Deformation im Sinne einer qualitativen Substitution aus. Weiterhin finden sie Anwendung beim Ausgleich von Störungen des Verhältnisses der Isomeren zueinander.In contrast, they resemble a molecular deformation in multiple sclerosis in terms of a qualitative substitution. Continue to find she Use to compensate for disturbances in the ratio of the isomers to one another.

Die erfindungsgemäßen Arzneimittel können die genannten Aldehyde und/oder Säuren in Form von reinen geometrischen oder optischen Isomeren oder in Form von Gemischen ihrer isomere enthalten. Die bevorzugten Verbindungen weisen folgende Zahl geometrischer und optischer Isomere auf: 6-n-Dodecenaldehyd ; 2 2 Isomere 8-n-Xexadecenaldehyd 2 Isomere 6,12-n-Octadecadienaldehyd 4 Isomere 8,16-n-Tetracosadien-2-hydroxyaldehyd 8 Isomere 8-n-Hexadecensäure 2 Isomere HOOC-CcH2)6cH=CH-(CH2)6cH3 (V) 8,16-n-Tetracosadien-2-hydroxysäure 8 Isomere HOOC.CHOH.(CH2)5.CH=CH.(CH2)6.CH=CH.(CH2)6.CH3 (VI) Besonders bevorzugt werden die Verbindungen (I) bis (IV).The medicaments according to the invention can contain the aldehydes and / or acids mentioned in the form of pure geometric or optical isomers or in the form of mixtures of their isomers. The preferred compounds have the following number of geometric and optical isomers: 6-n-dodecenaldehyde; 2 2 isomers 8-n-Xexadecenaldehyde 2 isomers 6,12-n-octadecadienaldehyde 4 isomers 8,16-n-tetracosadiene-2-hydroxyaldehyde 8 isomers 8-n-hexadecenoic acid 2 isomers HOOC-CcH2) 6cH = CH- (CH2) 6cH3 (V) 8,16-n-tetracosadiene-2-hydroxy acid 8 isomers HOOC.CHOH. (CH2) 5 .CH = CH. (CH2 ) 6.CH = CH. (CH2) 6.CH3 (VI) The compounds (I) to (IV) are particularly preferred.

VorzuwweiSe enthält das Arzneimittel die genannten Verbindungen in Form ihrer Gemische. Diese Gemische sollen bevorzugt alle Isomeren der Verbindungen enthalten. Vorzugsweise liegen die Verbindungen in äquimolarer Menge vor; ausgenommen Dodecenaldehyd und Hexadecenaldehyd, die in doppelter molarer Menge zugemischt werden. -Die erfindungemäßen Arzneimittel können die Aldehyde und Karbonsäuren auch in Form von pharmazeutisch verträglichen Derivaten enthalten, die leicht wieder in die Aldehyde bzw.Karbonsäuren überführbar sind.The medicinal product preferably contains the compounds mentioned in Form of their mixtures. These mixtures should preferably contain all isomers of the compounds contain. The compounds are preferably present in an equimolar amount; except Dodecenaldehyde and hexadecenaldehyde, which are mixed in in double the molar amount. The medicaments according to the invention can also use the aldehydes and carboxylic acids in the form Contained from pharmaceutically acceptable derivatives that easily convert back to the aldehydes or carboxylic acids are transferable.

Aldehyde können in verschiedenen Formen, wie Z.B. in der Enol-Form oder in der Form von Aldol-Additionsverbindungen vcrliegen.Aldehydes can be in various forms, such as in the enol form or in the form of aldol addition compounds.

Typische Beispiel für Aldehydderivate sind die Acetale, z.B. von Äthanol, Glykol, Glycerin, und anderen mit leicht abspaltbaren Molekülen gebundene Aldehyde.Typical examples of aldehyde derivatives are the acetals, e.g. from ethanol, Glycol, glycerine, and other aldehydes bound with easily cleavable molecules.

Beispiele für einsetzbare Säurederivate sind Salze und Ester der Karbonsäuren. Typische Beispiele sind die-Alkalisalze, wie Natrium-, Kaliumsalze, Calciumsalze, und die Äthanol- und Glycerinester.Examples of acid derivatives that can be used are salts and esters of carboxylic acids. Typical examples are the alkali salts, such as sodium, potassium salts, calcium salts, and the ethanol and glycerol esters.

So lassen sich z.B. die Ätkrderivate und die Derivate mit physiologischen Gallensäuren, nämlich der Glykocholsäure, der Taurocholsäure, der Cholsäure-desoxycholsäure und Lithocholsäure oder die Glycerinderivate verwenden.For example, the ether derivatives and the derivatives with physiological Bile acids, namely glycolic acid, taurocholic acid, cholic acid-deoxycholic acid and use lithocholic acid or the glycerol derivatives.

Die in den erfindungsgemäßen Arzneimitteln verwendeten Verbindungen sind nach an sich bekannten Verfahren synthetisierbar. Im folgenden werden zur Erläuterung Syntheseverfahren für einige der Verbindungen aufgeführt.The compounds used in the medicaments according to the invention can be synthesized by methods known per se. The following are explanatory Synthetic procedures for some of the compounds are listed.

Herstellung von cis- und trans-6-Dodecenaldiäthylacetal: trans-CH3 . (CH2)4 . CH = CH . (CH2)4 . CH(OC2H5)2.Production of cis- and trans-6-dodecenal diethyl acetal: trans-CH3. (CH2) 4. CH = CH. (CH2) 4. CH (OC2H5) 2.

Herstellung von cis- und trans-8-Hexadecenaldiäthylacetal und cis- und trans-8-Hexadecensäure: cis-CH3.(CH2)6.CH=CH(CH2)6.MgBr trans-CH3.(CH2)6.CH=CH(CH2)6.COOH Herstellung von Pyranacetal-1-butan-4-natriumacetylidcis- und trans-1,10-dibrom-dec-5-en: Br.(CH2)4.CH=CH.(CH2)4.Br Herstellung von cis,trans- und trans,trans- und cis,cis-6,12-Octadecdienal-diäthylacetal (wenn cis zu cis eis führt) CH3.(CH2)4.CH=CH(CH2)4.CH=CH(CH2)4.Br CH3.(CH2)4.CH=CH(CH2)4.CH=CH(CH2)4.CH(OC2H5)2 CH3.(CH2)4.CH=CH(CH2)4.CH=CH(CH2)4.CH(OC2H5)2 Herstellung von cis,cis- und trans,cis- und trans,trans-6,12-Octadecdienal-diäthylacetal: CH3.(CH2)4.CH=CH(CH2)4.Br cis CH3.(CH2)4.CH=CH(CH2)4.Br - NaC#C.(CH2)4.O.PY CH3.(CH2)4.CH=CH(CH2)4.CH=CH(CH2)4.CH(OC2H5)2 cis cis CH3.(CH2)4.CH=CH(CH2)4.Br trans CH3.(CH2)4.CH=CH(CH2)4.Br - NaC#C.(CH2)4.O PY trans CH3.(CH2)4.CH=CH(CH2)4.CH=CH(CH2)4.CH(OC2H5)2 Herstellung von Pyranacetal-1 -pentan-5-natrium-acetylid und cis- und trans-Brom-1-tridec-7-en-13-pyranacetal: PY O.(CH2)5.CH=CH.(CH2)6.Br trans Herstellung von cis, cis-, trans, cis- und trans, trans-1-Brom-dicosa-6,14-dien: CH3.(CH2)6.CH=CH.(CH2)6.Br trans CH3.(CH2)6.CH=CH.(CH2)6.Br - Na C=C.(CH2)5 O PY cis/trans CH3.(CH2)6.CH=CH.(CH2)6.CH=CH.(CH2)5 Br cis/trans cis CH3.(CH2)6.CH=CH.(CH2)6.CH=CH.(CH2)5 Br trans cis Herstellung von cis,cis-, cis,trans- und trans,trans-1-Brom-docosa-6,14-dien: CH3.(CH2)6.CH=CH.(CH2)6.CH=CH.(CH2)5 Br cis cis/trans CH3.(CH2)6.CH=CH.(CH2)6.CH=CH.(CH2)5 Br trans trans Herstellung von cis,cis-, cis, trans-, trans,trans-optisch-α- und ß-8,16-Tetraqcosadien-2-hydroxy-aldehyd diäthylacetal; und der entsprechenden Carbonsäure: CH3.(CH2)6.CH=CH.(CH2)6.CH=CH.CHOH.CH(OC2H5)2 cis/trans cis/trans α,ß In den zuvor erwähnten Synthesen können auch anstelle der Dihalogenverbindungen des Typs Br (CH2)x Br (zwel Halogenatome der gleichen Art) Dihalogenverbindungen des Typs Cl (CH2)x.Br oder andere (zwei Halogenatome unterschiedlicher Arten) verwendet werden.Production of cis- and trans-8-hexadecenal diethyl acetal and cis- and trans-8-hexadecenoic acid: cis-CH3. (CH2) 6.CH = CH (CH2) 6.MgBr trans-CH3. (CH2) 6.CH = CH (CH2) 6.COOH Preparation of pyranacetal-1-butane-4-sodium acetylidecis- and trans-1,10-dibromo-dec-5-ene: Br. (CH2) 4.CH = CH. (CH2) 4.Br Preparation of cis, trans and trans, trans and cis, cis-6,12-octadecdienal diethyl acetal (if c sharp leads to c sharp ice) CH3. (CH2) 4.CH = CH (CH2) 4.CH = CH (CH2) 4.Br CH3. (CH2) 4.CH = CH (CH2) 4.CH = CH (CH2) 4.CH (OC2H5) 2 CH3. (CH2) 4.CH = CH (CH2) 4.CH = CH (CH2) 4.CH (OC2H5) 2 Preparation of cis, cis- and trans, cis- and trans, trans-6,12-octadecdienal- dietary acetal: CH3. (CH2) 4.CH = CH (CH2) 4.Br cis CH3. (CH2) 4.CH = CH (CH2) 4.Br - NaC # C. (CH2) 4.O.PY CH3. (CH2) 4.CH = CH (CH2) 4.CH = CH (CH2) 4.CH (OC2H5) 2 cis cis CH3. (CH2) 4.CH = CH (CH2) 4.Br trans CH3. (CH2) 4.CH = CH (CH2) 4.Br - NaC # C. (CH2) 4.O PY trans CH3. (CH2) 4.CH = CH (CH2) 4.CH = CH (CH2) 4.CH (OC2H5) 2 Preparation of pyranacetal-1-pentane-5-sodium acetylide and cis- and trans-bromo-1 -tridec-7-en-13-pyranacetal: PY O. (CH2) 5.CH = CH. (CH2) 6.Br trans Preparation of cis, cis-, trans, cis- and trans, trans-1-bromo-dicosa-6,14-diene: CH3. (CH2) 6.CH = CH. (CH2) 6.Br trans CH3. (CH2) 6.CH = CH. (CH2) 6.Br - Na C = C. (CH2) 5 O PY cis / trans CH3. (CH2) 6.CH = CH. (CH2) 6.CH = CH. (CH2) 5 Br cis / trans cis CH3. (CH2) 6.CH = CH. (CH2) 6.CH = CH. (CH2) 5 Br trans cis Preparation of cis, cis-, cis, trans- and trans, trans-1-bromo-docosa-6 , 14-dien: CH3. (CH2) 6.CH = CH. (CH2) 6.CH = CH. (CH2) 5 Br cis cis / trans CH3. (CH2) 6.CH = CH. (CH2) 6.CH = CH. (CH2) 5 Br trans trans Production of cis, cis-, cis, trans-, trans, trans-optical-α- and ß- 8,16-tetraqcosadiene-2-hydroxy-aldehyde diethylacetal; and the corresponding carboxylic acid: CH3. (CH2) 6.CH = CH. (CH2) 6.CH = CH.CHOH.CH (OC2H5) 2 cis / trans cis / trans α, ß In the aforementioned syntheses, instead of the dihalogen compounds of the Br (CH2) x Br type (two halogen atoms of the same kind), dihalogen compounds of the Cl (CH2) x.Br type or others (two halogen atoms of different kinds) can be used.

Die erfindungsgemäßen Arzneimittel können peroral, rektal, intramuskulär oder u.U. auch intravenös verabreicht werden, wobei die intramuskuläre Darreichung nach Möglichkeit vermieden werden sollte.The medicaments according to the invention can be administered orally, rectally, intramuscularly or may also be administered intravenously, the intramuscular administration should be avoided whenever possible.

Bevorzugt werden sie peroral verabreicht und liegen in einer für die perorale Verabreichung geeigneten Form vor. Sie können z.B. in Form von Lösungen, Tabletten oder Kapseln yorliegen oder auch in Form von Emulsionen. Solche Zubereitungen können unter Zuhilfenahme von üblichen Trägern, Streckmitteln und erforderlichenfalls Formulierungshilfsmitteln mit oder ohne Zusatz von ergänzenden Arzneimitteln hergestellt werden. Die verwendeten Träger können fest oder flüssig sein. Ein bevorzugtes Trägermaterial ist raffiniertes Pflanzenöl oder sonstige Speise- oder Diätfette. Im ersteren Fall kann das erfindungsgemäße Mittel z.B. in Form von Kapseln, Suppositorien oder Tabletten vorliegen, die Bindemittel und Schmiermittel enthalten können und beschichtet sein können.They are preferably administered orally and are in one for the oral administration suitable form. You can e.g. in the form of solutions, Tablets or capsules are available or in the form of emulsions. Such preparations can with the help of customary carriers, extenders and if necessary Formulation auxiliaries produced with or without the addition of supplementary drugs will. The carriers used can be solid or liquid. A preferred carrier material is refined vegetable oil or other edible or dietary fats. In the former case For example, the agent according to the invention can be in the form of capsules, suppositories or tablets are present, which can contain binders and lubricants and be coated can.

Wenn der Träger oder das Verdünnungsmittel eine Flüssigkeit ist, dann kann das Mittel in Form von Emulsionen oder Suspensionen vorliegen.If the carrier or diluent is a liquid, then the agent can be in the form of emulsions or suspensions.

Die Mittel können in Dosiseinheitsformen vorliegen, wobei jede Dosiseinheit die ganze Tagesdosis oder einen Teil davon enthalten kann.The agents may be in unit dosage forms, each unit dosage may contain all or part of the daily dose.

Die bevorzugten Dosiseinheitszubereitungen sind insbesondere Tabletten, Kapseln oder Emulsionen.The preferred unit dose preparations are in particular tablets, Capsules or emulsions.

Die Dosis der erfindungsgemäßen Arzneimittel liegt im Bereich von 20 mg/kg Körpergewicht bis 500 mg/kg Körpergewicht täglich. Bevorzugte Mengen betragen 50 bis 200 mg/kg/Tag.The dose of the medicaments according to the invention is in the range of 20 mg / kg body weight to 500 mg / kg body weight daily. Preferred amounts are 50 to 200 mg / kg / day.

Als Substitutionstherapie muß die Verabreichung in der Regel während langer Zeit weitergeführt werden, manchmal während Monaten und Jahren. Es ist ein Vorteil der erfindungsgemäßen Verbindungen, daß sie körpereigene Substanzen darstellen und somit auch bei langer Verabreichung gut verträglich sind.As a substitution therapy, the administration usually has to take place during continued for a long time, sometimes for months and years. It is a The advantage of the compounds according to the invention that they are endogenous substances and are therefore well tolerated even after long-term administration.

Claims (6)

Patentansprüche 1. Arzneimittel, enthaltend als Wirksubstanz mindestens einen gradkettigen ungesättigten Aldehyd mit 12 bis 24 C-Atomen oder dessen pharmazeutisch annehmbares Derivat, ggf. Claims 1. Medicaments containing at least as active ingredient a straight-chain unsaturated aldehyde with 12 to 24 carbon atoms or its pharmaceutical acceptable derivative, if applicable zusammen mit üblichen Trägern und/oder Hilfsmitteln. together with the usual carriers and / or aids. 2. Arzneimittel nach Anspruch 1, dadurch gekennzeichnet, daß der Aldehyd 6-n-Dodecenaldehyd, 8-n-Hexadecenaldehyd, 6, 12-n-Octadecadienaldehyd und/oder 8-16-n-Tetracosadien-2-hydroxyaldehyd ist.2. Medicament according to claim 1, characterized in that the aldehyde 6-n-dodecenaldehyde, 8-n-hexadecenaldehyde, 6, 12-n-octadecadienaldehyde and / or 8-16-n-tetracosadiene-2-hydroxyaldehyde is. 3. Arzneimittel, enthaltend als Wirksubstanz mindestens eine der Verbindungen: 8-n-Hexadecensäure, 8-16-n-Tetracosadien-2-hydroxysäure oder ihre pharmazeutisch annehmbaren Derivate, ggf. zusammen mit üblichen Trägern und/oder Hilfsmitteln.3. Medicinal products containing at least one of the compounds as an active ingredient: 8-n-hexadecenoic acid, 8-16-n-tetracosadiene-2-hydroxy acid or their pharmaceuticals acceptable derivatives, optionally together with customary carriers and / or auxiliaries. 4. Arzneimittel nach einem der Ansprüche 1 - 3, dadurch gekennzeichnet, daß es die Verbindungen in Form von Gemischen der Isomeren enthält.4. Medicament according to one of claims 1-3, characterized in that that it contains the compounds in the form of mixtures of the isomers. 5. Geradkettiger ungesättigter Aldehyd der Formel: und ihre optischen und geometrischen Isomeren.5. Straight-chain unsaturated aldehyde of the formula: and their optical and geometric isomers. 6. 8,16-n-Tetracosadien-2-hydroxysäure und ihre optischen und geometrischen Isomeren.6. 8,16-n-tetracosadiene-2-hydroxy acid and its optical and geometrical properties Isomers.
DE19792902160 1979-01-20 1979-01-20 Medicaments for treating lipid metabolism disorders - contg. unsatd. aldehyde cpds., 8-hexadecenoic acid, or 2-hydroxy-8-16-tetracosa:dien-oic acid Granted DE2902160A1 (en)

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DE19792902160 DE2902160A1 (en) 1979-01-20 1979-01-20 Medicaments for treating lipid metabolism disorders - contg. unsatd. aldehyde cpds., 8-hexadecenoic acid, or 2-hydroxy-8-16-tetracosa:dien-oic acid

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DE2902160C2 DE2902160C2 (en) 1991-09-26

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987004926A2 (en) * 1986-02-14 1987-08-27 Nagy Adly Habib Method of modifying the lipid structure of cell membranes and pharmaceutical compositions for use therein
WO1992001450A1 (en) * 1990-07-16 1992-02-06 Lipotech Partners Limited Partnership Food and pharmaceutical compositions containing short chain monounsaturated fatty acids and methods of using

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
C.A., 89, 1978, 3407m *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987004926A2 (en) * 1986-02-14 1987-08-27 Nagy Adly Habib Method of modifying the lipid structure of cell membranes and pharmaceutical compositions for use therein
WO1987004926A3 (en) * 1986-02-14 1988-05-19 Nagy Adly Habib Method of modifying the lipid structure of cell membranes and pharmaceutical compositions for use therein
WO1992001450A1 (en) * 1990-07-16 1992-02-06 Lipotech Partners Limited Partnership Food and pharmaceutical compositions containing short chain monounsaturated fatty acids and methods of using

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Publication number Publication date
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