EP0091436A1 - Nouveaux medicaments presentant une activite sur le systeme nerveux central - Google Patents

Nouveaux medicaments presentant une activite sur le systeme nerveux central

Info

Publication number
EP0091436A1
EP0091436A1 EP19820901502 EP82901502A EP0091436A1 EP 0091436 A1 EP0091436 A1 EP 0091436A1 EP 19820901502 EP19820901502 EP 19820901502 EP 82901502 A EP82901502 A EP 82901502A EP 0091436 A1 EP0091436 A1 EP 0091436A1
Authority
EP
European Patent Office
Prior art keywords
alanine
hydroxy
acid
naphthyl
nervous system
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.)
Withdrawn
Application number
EP19820901502
Other languages
German (de)
English (en)
Inventor
Hans Georg Schlossberger
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.)
Max Planck Gesellschaft zur Foerderung der Wissenschaften eV
Original Assignee
Max Planck Gesellschaft zur Foerderung der Wissenschaften eV
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 Max Planck Gesellschaft zur Foerderung der Wissenschaften eV filed Critical Max Planck Gesellschaft zur Foerderung der Wissenschaften eV
Publication of EP0091436A1 publication Critical patent/EP0091436A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen

Definitions

  • L-tryptophan an essential amino acid, is known to have sleep-promoting properties. It is therefore used in medicines that induce sleep.
  • D L- ⁇ - (naphthy1-1) alanine has a similar activity (cf. Pharmacol. Biochem. Behav. 1979, Vol. 11, 319-323).
  • the present invention relates to medicaments with an effect on the central nervous system, in particular with sleep-promoting activity, which act as
  • ⁇ -f (7-hydroxy-naphthyl- (1) J -alanine and its lower alkyl esters have a pronounced effect on the central nervous system with a broad spectrum of activity. They show above all a strong general hypnotic activity with in particular sleep-promoting effects Effect, but also effectiveness against overactivity, antidepressant, antispasmodic and analgesic effect, especially for headaches. detrimental effect outperforms in various ways, e.g. B.
  • Alkyl esters are esters with 1 to 4 carbon atoms in the alkyl radical, and in particular the ethyl ester.
  • the active substances can also be used in the form of their salts with physiologically tolerable inorganic or organic acids and bases.
  • the lower alkyl esters are preferably used in the form of their salts with physiologically compatible acids, in particular with HCl.
  • the salt with glutamic acid in particular has proven to be expedient in order to achieve an improvement in solubility.
  • optically inactive D L form of ⁇ -
  • the antipodes can be separated by the methods known per se for antipode separations.
  • the compounds used according to the invention showed a pronounced effect on the central nervous system in the sense of a hypnotic effect after intraperitoneal (i.p.) administration.
  • ⁇ -7-hydroxy-naphthyl- (l) J-alanine 30 mg / kg, suspended in physiological sodium chloride solution, 2 ml each, and 150 mg / kg, suspended in 40% aqueous propylene glycol, 2 ml each, for ß- 7-hydroxy-naphthyl- (l) J-alanine ethyl ester hydrochloride: 120 mg / kg, aqueous solution, 2 ml each.
  • Dragees, suppositories, syrups, injection solutions, etc. The preparations are prepared according to the usual known methods.
  • ⁇ -7-hydroxy-naphthyl- (l) _J-alanine is sparingly soluble in water and is therefore preferably administered intraperitoneally, subcutaneously or orally, while the lower alkyl esters are due to their water solubility can also be administered intracardially and intravenously.
  • the pharmaceutical preparations generally contain ⁇ -7-hydroxy-naphthyl- (l)]] - alanine and / or its lower alkyl esters as the sole active ingredients in addition to the usual pharmaceutical carriers;
  • active substances in the medicinal product which do not influence the desired effect and possibly even support it, and which do not lead to an intolerance reaction, such as.
  • B. vitamins, analgesic Substances, etc. In order to support the effectiveness, the presence of a decarboxylase inhibitor has proven to be particularly advantageous.
  • a dosage unit of the drug contains 10 to 1000 mg, in particular 100 to 500 mg of active ingredient.
  • 1 to 5 dosage units are generally administered, preferably approximately 30 to 60 minutes before bedtime. The dosage depends primarily on the severity of the sleep disorder and the general condition of the patient.
  • the starting substance for the synthesis of ß-j_7-hydroxy-naphthyl- (l) J-alanine and its lower alkyl esters is 7-benzyloxy-l-hydroxymethyl-naphthalene (V), which is derived from 7-hydroxynaphthoic acid- (1) (I ) Karol Dziew ⁇ nski, H. Galitzerowna and A. Kocwa, Bull.Intern, de l'Acad. Polon. des Sciences et Lettres, Classe D. 0 Sc. Math, et Naturelles, Ser.A, 1926, 209-242, Univ.
  • X-HC1 crystallizes from a solution of X in ethanolic HCl in the form of colorless needles at mp 230 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Medicament presentant une activite sur le systeme nerveux central; il est caracterise par le fait qu'il contient en tant que substance active la (Beta)-(7-hydroxy-naphihyle-(1))-alanine et/ou son ester alcoylique presentant 1 a 4 atomes de carbone dans le residu alkyle.
EP19820901502 1981-05-20 1982-05-14 Nouveaux medicaments presentant une activite sur le systeme nerveux central Withdrawn EP0091436A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3120099 1981-05-20
DE19813120099 DE3120099A1 (de) 1981-05-20 1981-05-20 Neues arzneimittel mit wirkung auf das zentralnervensystem

Publications (1)

Publication Number Publication Date
EP0091436A1 true EP0091436A1 (fr) 1983-10-19

Family

ID=6132817

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19820901502 Withdrawn EP0091436A1 (fr) 1981-05-20 1982-05-14 Nouveaux medicaments presentant une activite sur le systeme nerveux central

Country Status (4)

Country Link
EP (1) EP0091436A1 (fr)
JP (1) JPS58500760A (fr)
DE (1) DE3120099A1 (fr)
WO (1) WO1982004045A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ213986A (en) * 1984-10-30 1989-07-27 Usv Pharma Corp Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4169108A (en) * 1973-08-16 1979-09-25 Sterling Drug Inc. 5(OR 6)-[(Substituted-amino)alkyl]-2,3-naphthalenediols

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8204045A1 *

Also Published As

Publication number Publication date
DE3120099A1 (de) 1982-12-09
JPS58500760A (ja) 1983-05-12
WO1982004045A1 (fr) 1982-11-25

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Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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AK Designated contracting states

Designated state(s): AT BE CH DE FR GB LI LU NL SE

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18D Application deemed to be withdrawn

Effective date: 19831128

RIN1 Information on inventor provided before grant (corrected)

Inventor name: SCHLOSSBERGER, HANS GEORG