BE471555A - - Google Patents

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Publication number
BE471555A
BE471555A BE471555DA BE471555A BE 471555 A BE471555 A BE 471555A BE 471555D A BE471555D A BE 471555DA BE 471555 A BE471555 A BE 471555A
Authority
BE
Belgium
Prior art keywords
emi
type
condense
soda
distilled
Prior art date
Application number
Other languages
English (en)
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.)
Publication of BE471555A publication Critical patent/BE471555A/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

Description


  Procédé de préparation de diamines substituées

  
Dans de précédentes demandes de brevets, on a décrit la préparation de diamines substituées du type

  

 <EMI ID=1.1> 


  
 <EMI ID=2.1> 

  
Ces produits avaient été reconnus d'activité physiologique intéressante. 

  
Il a maintenant été trouvé que les diamines du type, : 

  

 <EMI ID=3.1> 


  
dans lesquelles Het représente un noyau hétérocyclique, R un reste alcoyle, aralcoyle ou hétérocyclique relié à l'azote 

  
 <EMI ID=4.1> 

  
 <EMI ID=5.1>   <EMI ID=6.1> 

  
alcoyles, présentent également des propriétés physiologiques susceptibles d'emplois thérapeutiques, en particulier en raison de l'activité anti-histaminique de la plupart d'entre eux..

  
Selon la présente invention, les produits ainsi définis peuvent, être obtenus par application des méthodes généralement connues pour la préparat ion des diamines et, nommément, par condensation des amines secondaires du type : het - NH - R, éventuellement sodées, avec une amine tertiaire halogénée du type :

  

 <EMI ID=7.1> 


  
dans laquelle X est un atome d'halogène et où tous les autres signes représentatifs ont la même signification que dans la formule générale ci-dessus; ou par condensation d'une diamine substituée du type :

  

 <EMI ID=8.1> 


  
 <EMI ID=9.1> 

  
On peut également condenser une diamine -du type :

  

 <EMI ID=10.1> 


  
avec un dérivé halogéné d'un hétérocycle,

  
Enfin, les mêmes produits peuvent être obtenus par condensation avec une amine secondaire du type :

  
 <EMI ID=11.1> 

  
 <EMI ID=12.1> 

  
Dans les formules précédemment citées, les différents indices et signes ont toujours la même signification qu'indiqué au début,

  
Les exemples ,suivants montrent, à titre non limitatif,  <EMI ID=13.1> 

  
On chauffe vers 80[deg.] dans 50 ce de toluène sec 46 gr

  
 <EMI ID=14.1> 

  
ajoute peu à peu 9,5 gr d'amidure de sodium à 85 %. Après dégagement de l'ammoniac, on distille la majeure partie du toluène.

  
 <EMI ID=15.1> 

  
 <EMI ID=16.1> 

  
140[deg.] puis termine par 1/2 h de chauffage sous vide à 150 mm. On! reprend par l'acide chlorhydrique dilué et l'éther. On décanta

  
 <EMI ID=17.1> 

  
hygroscopique, facilement soluble dans l'eau.

Exemple 2 

  
 <EMI ID=18.1> 

  
4,5 gr d'amidure de sodium à 85 % dans' 30 ce de toluène. On distille la majeure partie du toluène puis on coule lentement une solution éthérée de 10 gr de diméthylaminochloréthane en une heure, en agitant et distillait l'éther. On chauffe ensuite en-

  
 <EMI ID=19.1>

Claims (1)

  1. <EMI ID=20.1>
    puis on la libère par la soude, extrait à l'éther et distille.
    <EMI ID=21.1>
    - REVENDICATIONS -
    Procédé de préparation de diamines substituées du type
    <EMI ID=22.1>
    dans lesquelles Het représente un noyaa hétérocyclique, R un
    <EMI ID=23.1>
    éventuellement sodées, avec une amine tertiaire halogénée,du dans laquelle X est un atome d&#65533;halogène; <EMI ID=24.1>
    <EMI ID=25.1> <EMI ID=26.1> - ou à condenser une domine du type <EMI ID=27.1> éventuellement sodée, avec un dérivé halogéné d'un hétérocycle: - ou enfin à condenser une aminé secondaire dutype :
    <EMI ID=28.1>
    <EMI ID=29.1>
    <EMI ID=30.1>
BE471555D 1943-06-22 BE471555A (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR913931T 1943-06-22

Publications (1)

Publication Number Publication Date
BE471555A true BE471555A (fr)

Family

ID=37401009

Family Applications (1)

Application Number Title Priority Date Filing Date
BE471555D BE471555A (fr) 1943-06-22

Country Status (3)

Country Link
BE (1) BE471555A (fr)
DE (1) DE880749C (fr)
FR (1) FR913931A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE476794A (fr) * 1946-10-17
DE931828C (de) * 1947-08-19 1955-08-18 Geigy Ag J R Verfahren zur Herstellung von AEthylendiaminderivaten
FR2579208B1 (fr) * 1985-03-22 1987-05-07 Sanofi Sa Nouveaux derives de le 5-h pyrido (3', 4' : 4,5) pyrrolo (3,2-c) pyridine, leur procede de preparation et leur activite antitumorale
EP0226508A1 (fr) * 1985-12-02 1987-06-24 Sanofi Dérivés de l'indolo(3,2-c)quinoléine, leur procédé de préparation et leur activité antitumorale
FR2590898B1 (fr) * 1985-12-02 1987-12-11 Sanofi Sa Derives de l'indolo (3-2-c) quinoleine, leur procede de preparation et leur activite antitumorale
FR2656610B1 (fr) * 1989-12-29 1992-05-07 Sanofi Sa Derives d'amino-2 phenyl-4 thiazole, leur procede de preparation et leur application therapeutique.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH258138A (fr) * 1943-06-22 1948-11-15 Rhone Poulenc Chemicals Procédé de préparation de la diméthylaminoéthyl-N-benzyl-N-a-aminopyridine.

Also Published As

Publication number Publication date
FR913931A (fr) 1946-09-24
DE880749C (de) 1953-06-25

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