GB792576A - N-acyl derivatives of glutamine and asparagine and compositions containing them - Google Patents

N-acyl derivatives of glutamine and asparagine and compositions containing them

Info

Publication number
GB792576A
GB792576A GB25451/55A GB2545155A GB792576A GB 792576 A GB792576 A GB 792576A GB 25451/55 A GB25451/55 A GB 25451/55A GB 2545155 A GB2545155 A GB 2545155A GB 792576 A GB792576 A GB 792576A
Authority
GB
United Kingdom
Prior art keywords
asparagine
glutamine
acyl
glutamines
acetyl
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
GB25451/55A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB792576A publication Critical patent/GB792576A/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/195Carboxylic acids, e.g. valproic acid having an amino group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups

Landscapes

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

Abstract

The invention comprises N-butyryl-, N-benzoyl- and N-palmitoyl-glutamines and N-butyryl-, N-palmitoyl- and N-diphenylacetylasparagines. These compounds, and other N-acyl-glutamines and asparagines such as the N-formyl, N-acetyl, N-propionyl, N-valeryl, N-isobutyryl, N-phenylacetyl, N-trimethylacetyl, N-stearoyl and N-sulphonyl compounds, may be prepared by reacting glutamine or asparagine with an acylating agent such as an acyl halide or acid anhydride, conveniently in a liquid reaction medium at 0 DEG C. under substantially neutral conditions, such conditions being conveniently achieved by first neutralizing the glutamine or asparagine with a base e.g. aqueous sodium hydroxide, and then adding, simultaneously, a solution of the acylating agent and a solution of a base. Salts of the N-acylated glutamines and asparagines may be prepared by conventional methods. Examples describe the preparation of the L-forms of the compounds of the invention and also the preparation of N-acetyl - L - glutamine, N - p - toluenesulphonyl-L - glutamine, N - acetyl - L - asparagine and N-phenylacetyl-L-asparagine.ALSO:An anticonvulsant composition comprises at least one compound selected from N-acyl derivatives of glutamine and of asparagine and salts of such derivatives and a solid pharmaceutical carrier, or a sterile liquid suitable for parenteral injection or an orally administrable oil. A liquid carrier may be accompanied by a solubilizer and/or dispersing agent, a liquid composition may be contained in a capsule and a solid composition may be in the form of a tablet or powder and may contain flavouring and disintegrating agents. Suitable solid carriers include corn starch, sugar, talc, and magnesium carbonate, and suitable oils include olive oil and sesame oil. Preferably the N-acyl group has 20 carbon atoms or less and is derived from a monocarboxylic acid, but it may be, for example, an N-sulphonyl group. Compositions in unit dosage form may contain from 500 mg. to 75 g. of active ingredient. A composition containing benzoyl-L-asparagine, veegum H.V., glycerine, methyl p-hydroxybenzoate, propyl p-hydroxybenzoate and water is described.
GB25451/55A 1954-09-22 1955-09-05 N-acyl derivatives of glutamine and asparagine and compositions containing them Expired GB792576A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US792576XA 1954-09-22 1954-09-22

Publications (1)

Publication Number Publication Date
GB792576A true GB792576A (en) 1958-04-02

Family

ID=22149406

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25451/55A Expired GB792576A (en) 1954-09-22 1955-09-05 N-acyl derivatives of glutamine and asparagine and compositions containing them

Country Status (1)

Country Link
GB (1) GB792576A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3364253A (en) * 1963-05-07 1968-01-16 Lab D Analyses Et De Rech S Ma Arginine n-acetyl-asparaginate and arginine n-acetyl-glutaminate
WO1999029814A2 (en) * 1997-12-10 1999-06-17 Keminova Italiana S.R.L. Method of preparing lipoproteins, lipoaminoacids, lipid esters, and glucolipids from olive oil and/or its constituents which are condensed with vegetal protein hydrolysates or aminoacids or esterificated with fatty alcohols or sugars
RU2632713C2 (en) * 2016-02-18 2017-10-09 Общество с ограниченной ответственностью "Фармамед" Delayed release pharmaceutical composition containing asparaginates
RU2632715C2 (en) * 2016-03-15 2017-10-09 Общество с ограниченной ответственностью "Фармамед" Sustained-release pharmaceutical composition containing asparaginates

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3364253A (en) * 1963-05-07 1968-01-16 Lab D Analyses Et De Rech S Ma Arginine n-acetyl-asparaginate and arginine n-acetyl-glutaminate
WO1999029814A2 (en) * 1997-12-10 1999-06-17 Keminova Italiana S.R.L. Method of preparing lipoproteins, lipoaminoacids, lipid esters, and glucolipids from olive oil and/or its constituents which are condensed with vegetal protein hydrolysates or aminoacids or esterificated with fatty alcohols or sugars
WO1999029814A3 (en) * 1997-12-10 1999-09-02 Keminova Italiana S R L Method of preparing lipoproteins, lipoaminoacids, lipid esters, and glucolipids from olive oil and/or its constituents which are condensed with vegetal protein hydrolysates or aminoacids or esterificated with fatty alcohols or sugars
US6512093B1 (en) 1997-12-10 2003-01-28 Keminova Italiana S.R.L. Method of preparing lipoproteins from fatty acids present in olive oil
RU2632713C2 (en) * 2016-02-18 2017-10-09 Общество с ограниченной ответственностью "Фармамед" Delayed release pharmaceutical composition containing asparaginates
RU2632715C2 (en) * 2016-03-15 2017-10-09 Общество с ограниченной ответственностью "Фармамед" Sustained-release pharmaceutical composition containing asparaginates

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