DE2655326C2 - Process for improving the solubility and stability of basic medicinal products in mono- and diglycerides of medium-chain fatty acids (C 6 -C 1 2) for the purpose of oral administration - Google Patents

Process for improving the solubility and stability of basic medicinal products in mono- and diglycerides of medium-chain fatty acids (C 6 -C 1 2) for the purpose of oral administration

Info

Publication number
DE2655326C2
DE2655326C2 DE19762655326 DE2655326A DE2655326C2 DE 2655326 C2 DE2655326 C2 DE 2655326C2 DE 19762655326 DE19762655326 DE 19762655326 DE 2655326 A DE2655326 A DE 2655326A DE 2655326 C2 DE2655326 C2 DE 2655326C2
Authority
DE
Germany
Prior art keywords
fatty acids
diglycerides
mono
medium
chain fatty
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
DE19762655326
Other languages
German (de)
Other versions
DE2655326A1 (en
Inventor
Theodor Prof. Dr.Rer.Nat. Eckert
Fritz H. Prof. Dr.med. 4400 Münster Kemper
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.)
Abbott Products GmbH
Original Assignee
Kali Chemie Pharma GmbH
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 Kali Chemie Pharma GmbH filed Critical Kali Chemie Pharma GmbH
Priority to DE19762655326 priority Critical patent/DE2655326C2/en
Publication of DE2655326A1 publication Critical patent/DE2655326A1/en
Application granted granted Critical
Publication of DE2655326C2 publication Critical patent/DE2655326C2/en
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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material 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)
  • Medicinal Preparation (AREA)

Description

Beispiel 1example 1

165 mg Hydroxyphenyl-methylaminoäthanol werden unter Zusatz von 290 mg Caprylsäure in 500 mg eines Gemisches von Mono- und Diglyceriden miltelkettiger Fettsäuren (C6-Ci2) gelöst.165 mg of hydroxyphenylmethylaminoethanol are dissolved in 500 mg of a mixture of mono- and diglycerides of medium-chain fatty acids (C 6 -Ci 2 ) with the addition of 290 mg of caprylic acid.

FormelzusammenstellungComposition of formulas

Hydroxyphenyl-methylaminoäthanolHydroxyphenyl-methylaminoethanol

HO-C >—CH-CH2-NH-CH3 HO-C> -CH-CH 2 -NH-CH 3

Claims (1)

Patentanspruch:Claim: Verfahren zur Verbesserung der Löslichkeit und Stabilität basischer Arzneistoffe in Gemischen aus Mono- und Diglyceriden mittelkettiger Fettsäuren [Cb-Cn) zum Zwecke der besseren Resorption der Arzneistoffe im Magen-Darm-Trakt, dadurch gekennzeichnet, daß den basischen Arzneistoffen freie Fettsäuren der Kettenlänge Ce-Cig, vorzugsweise C6-Cu, zugesetzt werden, und die so erhaltenen Salze in Gemischen aus Mono- und Diglyceriden mittelkettiger Fettsäuren (C6-Cu) gelöst werden.Process for improving the solubility and stability of basic medicinal substances in mixtures of mono- and diglycerides of medium-chain fatty acids [Cb-Cn) for the purpose of better absorption of the medicinal substances in the gastrointestinal tract, characterized in that the basic medicinal substances contain free fatty acids of chain length Ce Cig, preferably C 6 -Cu, are added, and the salts thus obtained are dissolved in mixtures of mono- and diglycerides of medium-chain fatty acids (C 6 -Cu) . Die Erfindung betrifft ein Verfahren zur Verbesserung der Löslichkeit und Stabilität basischer Arzneistoffe in Gemischen aus Mono- und Diglyceriden mittelkettiger Fettsäuren der Kettenlänge C6-Cu zum Zwecke der besseren Resorption der Arzneistoffe im Magen-Darm-TrakL The invention relates to a method for improving the solubility and stability of basic medicinal substances in mixtures of mono- and diglycerides of medium-chain fatty acids of chain length C 6 -Cu for the purpose of better absorption of the medicinal substances in the gastrointestinal tract Viele Arzneistoffe, die basische Gruppen tragen, liegen aus Gründen ihrer Löslichkeit in wäßrigen Medien oder aus Gründen ihrer Haltbarkeit vielfach in Form von Salzen, meist in Form von Hydrochloriden, vor. Diese Salze zeigen jedoch in Gemischen aus Mono- und Diglyceriden mittelkettiger Fettsäuren (Ce-C12) nur eine schlechte Löslichkeit und sind im Magen-Darm-Trakt häufig nur schwer resorbieirbar. Auch die Löslichkeit der freien Basen in den Mono- und Diglyceriden mittelkettiger Fettsäuren (C6-C12) ist häufig nur schlechL Soweit sie als Basen in diesem Lösungsmittel löslich sind, ist die Stabilität solcher Lösungen häufig nur gering, beispielsweise wegen der Möglichkeit von Umamidierungsvorgängen mit dem Lösungsmittel.For reasons of their solubility in aqueous media or for reasons of their shelf life, many medicinal substances which carry basic groups are often in the form of salts, mostly in the form of hydrochlorides. However, these salts show poor solubility in mixtures of mono- and diglycerides of medium-chain fatty acids (Ce-C12) and are often difficult to absorb in the gastrointestinal tract. The solubility of the free bases in the mono- and diglycerides of medium-chain fatty acids (C 6 -C 12) is also often poor. In so far as they are soluble as bases in this solvent, the stability of such solutions is often only low, for example because of the possibility of transamidation processes the solvent. Die Erfindung ist durch den Patentanspruch gekennzeichnet und besteht darin, die Basen mit Hilfe von Capronsäure (Ce) oder Caprylsäure (Ce) oder Caprinsäure (Cio) oder L&urinsäure (Ci 2) oder einer längerkettigen Fettsäure in ihre Salze zu überführen. Diese Salze zeigen nun gute Lösungs- und Sabilitätseigenschaften in den Mono- und Diglyceriden mittetkettiger Fettsäuren (C6-Cu) sowie in dieser Lösung gute Resorptionseigenschaften im Magen-Darm-TraktThe invention is characterized by the patent claim and consists in converting the bases into their salts with the aid of caproic acid (Ce) or caprylic acid (Ce) or capric acid (Cio) or luuric acid (Ci 2) or a longer-chain fatty acid. These salts now show good dissolving and stability properties in the mono- and diglycerides of medium-chain fatty acids (C 6 -Cu) and, in this solution, good absorption properties in the gastrointestinal tract Die Herstellung solcher Lösungen kann in der Weise erfolgen, daß den freien Basen äquivalente Mengen oder auch ein Oberschuß der obengenannten Fettsäuren, gegebenenfalls unter Erwärmen, hinzugefügt wird und die entstandenen Salze in einem Gemisch von Mono- und Diglyceriden mittelkettiger Fettsäuren (C6-Cu) gelöst werden. Die so erhaltenen .Väparaiionen zeigen für die Arzneistoffe gute Rcsorptionseigcnschäften im Magen-Darm-TrakLSuch solutions can be prepared in such a way that amounts equivalent to the free bases or an excess of the abovementioned fatty acids, if necessary with heating, are added and the resulting salts are mixed in a mixture of mono- and diglycerides of medium-chain fatty acids (C 6 -Cu) be solved. The preparations thus obtained show good absorption properties for the medicinal substances in the gastrointestinal tract Das folgende Beispiel erläutert idie Erfindung:The following example illustrates the invention:
DE19762655326 1976-12-07 1976-12-07 Process for improving the solubility and stability of basic medicinal products in mono- and diglycerides of medium-chain fatty acids (C 6 -C 1 2) for the purpose of oral administration Expired DE2655326C2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19762655326 DE2655326C2 (en) 1976-12-07 1976-12-07 Process for improving the solubility and stability of basic medicinal products in mono- and diglycerides of medium-chain fatty acids (C 6 -C 1 2) for the purpose of oral administration

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19762655326 DE2655326C2 (en) 1976-12-07 1976-12-07 Process for improving the solubility and stability of basic medicinal products in mono- and diglycerides of medium-chain fatty acids (C 6 -C 1 2) for the purpose of oral administration

Publications (2)

Publication Number Publication Date
DE2655326A1 DE2655326A1 (en) 1978-06-08
DE2655326C2 true DE2655326C2 (en) 1985-08-14

Family

ID=5994859

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19762655326 Expired DE2655326C2 (en) 1976-12-07 1976-12-07 Process for improving the solubility and stability of basic medicinal products in mono- and diglycerides of medium-chain fatty acids (C 6 -C 1 2) for the purpose of oral administration

Country Status (1)

Country Link
DE (1) DE2655326C2 (en)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICHTS-ERMITTELT

Also Published As

Publication number Publication date
DE2655326A1 (en) 1978-06-08

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Legal Events

Date Code Title Description
8110 Request for examination paragraph 44
D2 Grant after examination
8364 No opposition during term of opposition
8339 Ceased/non-payment of the annual fee