DE916290C - Process for the preparation of therapeutically valuable salts of N-aminoalkyl-phenothiazines substituted in the amino group - Google Patents

Process for the preparation of therapeutically valuable salts of N-aminoalkyl-phenothiazines substituted in the amino group

Info

Publication number
DE916290C
DE916290C DEC5140A DEC0005140A DE916290C DE 916290 C DE916290 C DE 916290C DE C5140 A DEC5140 A DE C5140A DE C0005140 A DEC0005140 A DE C0005140A DE 916290 C DE916290 C DE 916290C
Authority
DE
Germany
Prior art keywords
substituted
phenothiazines
amino group
aminoalkyl
preparation
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
DEC5140A
Other languages
German (de)
Inventor
Dr Walther Persch
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur AG
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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC5140A priority Critical patent/DE916290C/en
Application granted granted Critical
Publication of DE916290C publication Critical patent/DE916290C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Verfahren zur Herstellung therapeutisch wertvoller Salze von in der Aminogruppe substituierten N-Amin;oalkyl-phenothiazinen Bei der Verwendung von in der Aminogruppe substituierten N-Aminoalkyl-phenothiazinen. als Antihistaminica hat es sich für spezielle- Zwecke als vorteilhaft erwiesen, sie mit Gentisinsäure vereint anzuwenden.Process for the preparation of therapeutically valuable salts in the Amino group-substituted N-amine; oalkyl-phenothiazines When using in the amino group-substituted N-aminoalkyl-phenothiazines. as antihistamines it has proven advantageous for special purposes to use gentisic acid to apply in unison.

Es wurde nun gefunden, daß die genannten basischen Phenothiazinderivate mit Gentisinsäure echte Salze geben. Diese Salze lassen sich nach den für diese Art der Umsetzung gebräuchlichen Methoden herstellen, nämlich durch. einfaches Zusammengeben der freien Komponenten, vorzugsweise in geeigneten. Lösungsmitteln, oder durch doppelte Umsetzung eines üblichen Salzes eines Phenothiazinderivats der genannten Art mit einem Salz der Gentisinsäure, z. B. des salzsauren Salzes des substituierten Aminoalkyl-phenothiazins mit gentisinsaurem Natrium.It has now been found that the basic phenothiazine derivatives mentioned give real salts with gentisic acid. These salts can be classified according to the for this Type of implementation to produce common methods, namely through. easy putting together of the free components, preferably in suitable ones. Solvents, or by double Implementation of a common salt of a phenothiazine derivative of the type mentioned with a salt of gentisic acid, e.g. B. the hydrochloric acid salt of the substituted aminoalkyl-phenothiazine with sodium gentisate.

Beispiel 14,9 g N-(Diäthylaminoäthyl)-phenothiazin und 7,7 g Gentisinsäure werden in 2o ccm Alkohol 1/2 Stunde gekocht. Der Alkohol wird verdampft. Das rückständige C51 kristallisiert langsam. Der harte Kristallkuchen wird; aus 25o ccm Essigester und 1o ccm Alkohol umkristallisiert. Das auskristallisierte Produkt ist das chemisch reine gentisinsaure Salz des N-(Diäthyl,aminoäthy l)-phenothiazins vom Schmelzpunkt 148 bis 1q.9°.Example 14.9 g of N- (diethylaminoethyl) phenothiazine and 7.7 g of gentisic acid are boiled in 2o cc alcohol for 1/2 hour. The alcohol is evaporated. The backward one C51 slowly crystallizes. The hard crystal cake will; from 25o cc of ethyl acetate and 1o cc of alcohol recrystallized. The product that crystallizes out is chemical pure gentisic acid salt of N- (diethyl, aminoethyl) phenothiazine from melting point 148 to 1q.9 °.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung therapeutisch wertvoller Salze von in der Aminogruppe substituierten I\T-Aminoa-fkyl-phenothiazinen, dadurch gekennzeichnet, daß man die genannten Phenothiazinderivate in Form ihrer freien Basen mit Gentisinsäure umsetzt oder übliche Salze dieser Phenothiazinderivate mit Salzen der Gentisinsäure reagieren läßt.PATENT CLAIM: Process for the production of therapeutically valuable Salts of I \ T-Aminoa-fkyl-phenothiazines substituted in the amino group, thereby characterized in that one said phenothiazine derivatives in the form of their free Reacts bases with gentisic acid or common salts of these phenothiazine derivatives with Salts of gentisic acid can react.
DEC5140A 1951-12-22 1951-12-22 Process for the preparation of therapeutically valuable salts of N-aminoalkyl-phenothiazines substituted in the amino group Expired DE916290C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC5140A DE916290C (en) 1951-12-22 1951-12-22 Process for the preparation of therapeutically valuable salts of N-aminoalkyl-phenothiazines substituted in the amino group

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC5140A DE916290C (en) 1951-12-22 1951-12-22 Process for the preparation of therapeutically valuable salts of N-aminoalkyl-phenothiazines substituted in the amino group

Publications (1)

Publication Number Publication Date
DE916290C true DE916290C (en) 1954-08-09

Family

ID=7013598

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC5140A Expired DE916290C (en) 1951-12-22 1951-12-22 Process for the preparation of therapeutically valuable salts of N-aminoalkyl-phenothiazines substituted in the amino group

Country Status (1)

Country Link
DE (1) DE916290C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2752345A (en) * 1956-06-26 Gentisic acid salts of aminoalkyl-
DE1095282B (en) * 1958-06-06 1960-12-22 Rhone Poulenc Sa Process for the preparation of a phenthiazine derivative

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2752345A (en) * 1956-06-26 Gentisic acid salts of aminoalkyl-
DE1095282B (en) * 1958-06-06 1960-12-22 Rhone Poulenc Sa Process for the preparation of a phenthiazine derivative

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