[go: up one dir, main page]

CH139412A - Process for the preparation of a one-sided heterocyclically acylated diamine. - Google Patents

Process for the preparation of a one-sided heterocyclically acylated diamine.

Info

Publication number
CH139412A
CH139412A CH139412DA CH139412A CH 139412 A CH139412 A CH 139412A CH 139412D A CH139412D A CH 139412DA CH 139412 A CH139412 A CH 139412A
Authority
CH
Switzerland
Prior art keywords
preparation
sided
heterocyclically
ether
reaction
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH139412A publication Critical patent/CH139412A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines einseitig     heteroeykliseh        aeylierten        Diamins.       Es wurde gefunden, dass man zu einem  einseitig     heterocyklisch        acylierten        Diamin     gelangen kann, wenn man asymmetrisches       Diäthyläthylendiamin    mit einer Verbindung  von der Formel:

    
EMI0001.0008     
    in welcher R einen bei der Reaktion sich  abspaltenden Rest bedeutet, wie zum Beispiel  die     2-Phenyl-1,    2, 3,     4-tetrahydro-4-chinolin-          carbonsäure,    ihr     Anhydrid,    ihre Ester oder  ihre     Säurehalogenide,    in letzterem Falle  zweckmässig unter Verwendung säurebindender  Mittel, zur Reaktion bringt.  



  Das     2-Phenyl-1,    2, 3,     4-tetrahydro-4-chino-          lincarbonsäure-diäthyläthylendiamid    ist fest.  Es besteht aus 2     Isomeren,    die durch Kri-         stallisation    aus Äther getrennt werden kön  nen.

   Das in Äther schwer lösliche     Isomere     bildet feine     Nädelchen    vom     Smp.    1320, das  leichter lösliche glasklare Prismen vom     Srnp.          97,51'.    Das     Bichlorhydrat    des ersteren     Iso-          meren    schmilzt bei<B>1921,</B> das des letzteren  bei<B>2250,</B> beide unter Zersetzung. Die Salze  sind in Wasser leicht löslich.  



  Die neue Verbindung soll zu therapeu  tischen Zwecken Verwendung finden.  <I>Beispiel</I>  253 Teile     2-Phenyl-1,    2, 3,     4-tetrahydro-          4-chinolirrcarbonsäure    und<B>116</B> Teile asymme  trisches     Diäthyläthylendiamin    werden zusam  men auf 200-220   erhitzt. Das gebildete       2-Phenyl    -1, 2, 3,     4-tetrahydro-4-chinolincar-          bonsäure-diäthyläthylendiamid    erstarrt allmäh  lich nach dem Auswaschen mit Wasser zu einer  festen Masse. Es besteht aus     2Isomeren,    die sich  durch Kristallisation aus Äther trennen  lasen.



  Process for the preparation of a unilaterally heteroeyclic aylated diamine. It has been found that a diamine which is heterocyclically acylated on one side can be obtained if asymmetric diethylethylenediamine is combined with a compound of the formula:

    
EMI0001.0008
    in which R denotes a radical which is split off during the reaction, such as, for example, 2-phenyl-1, 2, 3, 4-tetrahydro-4-quinoline-carboxylic acid, its anhydride, its esters or its acid halides, in the latter case it is appropriate below Use acid-binding agents to react.



  The 2-phenyl-1, 2, 3, 4-tetrahydro-4-quinolinecarboxylic acid diethylethylenediamide is solid. It consists of 2 isomers, which can be separated by crystallization from ether.

   The isomer, which is sparingly soluble in ether, forms fine needles of m.p. 1320, the more easily soluble, crystal-clear prisms of Srnp. 97.51 '. The bichlorohydrate of the former isomer melts at <B> 1921, </B> that of the latter at <B> 2250, </B> both with decomposition. The salts are easily soluble in water.



  The new connection is intended to be used for therapeutic purposes. <I> Example </I> 253 parts of 2-phenyl-1, 2, 3, 4-tetrahydro-4-quinolirecarboxylic acid and 116 parts of asymmetric diethylethylenediamine are heated together to 200-220. The 2-phenyl -1, 2, 3, 4-tetrahydro-4-quinolinecarbonsäure-diethyläthylendiamid formed gradually solidifies after washing with water to a solid mass. It consists of 2 isomers, which can be separated by crystallization from ether.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines einseitig heterocyklisch acylierten Diamins, dadurch gekennzeichnet, dass man asymmetrisches Diä- thyläthylendiamin mit einer Verbindung von der Formel: EMI0002.0006 in welcher R einen bei der Reaktion sich abspaltenden Rest bedeutet, zur Reaktion bringt. Das 2-Phenyl-1, 2, 3, 4-tetrahydro-4-chino- lincarbonsäiire-diäthyläthylendiamid ist fest. Es besteht aus 2 Isomeren, die durch Kri stallisation aus Äther getrennt werden kön nen. PATENT CLAIM: Process for the preparation of a one-sided heterocyclic acylated diamine, characterized in that asymmetric diethylethylenediamine is mixed with a compound of the formula: EMI0002.0006 in which R denotes a radical which is split off during the reaction, brings about the reaction. The 2-phenyl-1, 2, 3, 4-tetrahydro-4-quinoline carboxylic acid diethylethylenediamide is solid. It consists of 2 isomers, which can be separated by crystallization from ether. Das in Äther schwer lösliche Isomere bildet feine Nädelchen vom Snip. 132', das leichter lösliche glasklare Prismen vom Smp. <B>97,50.</B> Das Bichlorhydrat des ersteren Isoineren schmilzt bei 192 , das des letzteren bei 225 , beide unter Zersetzung. Die Salze sind in Wasser leicht löslich. Die neue Verbindung sollzutherapeutischen Zwecken Verwendung finden. The isomer, which is sparingly soluble in ether, forms fine needles from the Snip. 132 ', the more easily soluble, crystal-clear prism of m.p. <B> 97.50. </B> The bichlorohydrate of the former isomer melts at 192, that of the latter at 225, both with decomposition. The salts are easily soluble in water. The new compound is intended to be used for therapeutic purposes.
CH139412D 1927-11-19 1927-11-19 Process for the preparation of a one-sided heterocyclically acylated diamine. CH139412A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139412T 1927-11-19
CH137337T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139412A true CH139412A (en) 1930-04-15

Family

ID=25712913

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139412D CH139412A (en) 1927-11-19 1927-11-19 Process for the preparation of a one-sided heterocyclically acylated diamine.

Country Status (1)

Country Link
CH (1) CH139412A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4952573A (en) * 1988-03-23 1990-08-28 Laboratoirs Alcon S.A. Compounds having GABA like activity, and use of same in tissue irrigating solutions
US5112836A (en) * 1989-06-19 1992-05-12 Kyorin Pharmaceutical Co., Ltd. Cyclic anthranililc acid carboxylic acid derivatives and medical therapeutic use thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4952573A (en) * 1988-03-23 1990-08-28 Laboratoirs Alcon S.A. Compounds having GABA like activity, and use of same in tissue irrigating solutions
US5112836A (en) * 1989-06-19 1992-05-12 Kyorin Pharmaceutical Co., Ltd. Cyclic anthranililc acid carboxylic acid derivatives and medical therapeutic use thereof

Similar Documents

Publication Publication Date Title
CH139412A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
CH149007A (en) Process for the preparation of a halogen-containing basic ether.
CH139418A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
CH139416A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
CH139414A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
CH139420A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
CH149008A (en) Process for the preparation of a halogen-containing basic ether.
CH137337A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
AT107595B (en) Process for the preparation of 2-amino-3-nitropyridine-5-sulfonic acid.
CH139419A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
CH151888A (en) Process for the preparation of an N-substituted compound of the pyridone series.
CH139415A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
CH107780A (en) Process for the preparation of a unilaterally acylated derivative of ethylene diamine.
CH139430A (en) Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.
CH217232A (en) Process for the preparation of 2-methyl-4-ethoxymethyl-6-oxy-pyridine-5-carboxamide.
CH139442A (en) Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.
CH139425A (en) Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.
CH159875A (en) Process for the preparation of a one-sided heterocyclically acylated diamine.
CH285030A (en) Process for the manufacture of a new pain reliever drug.
CH139422A (en) Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.
CH139424A (en) Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.
CH209079A (en) Process for the preparation of a new nitrogen-containing organic compound.
CH144710A (en) Process for the preparation of the 4-ethoxy-3-aminobenzoic acid diethylamino-ethanol ester.
CH136579A (en) Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.
CH236131A (en) Process for the preparation of a salt of 4-amino-benzenesulfonylaminomethanesulfonic acid which is readily soluble in water.