BE826668A - 3,14-DIHYDROCRIOCERINE AND METHOD OF PREPARATION. - Google Patents

3,14-DIHYDROCRIOCERINE AND METHOD OF PREPARATION.

Info

Publication number
BE826668A
BE826668A BE154312A BE154312A BE826668A BE 826668 A BE826668 A BE 826668A BE 154312 A BE154312 A BE 154312A BE 154312 A BE154312 A BE 154312A BE 826668 A BE826668 A BE 826668A
Authority
BE
Belgium
Prior art keywords
emi
vincamine
methanol
dehydro
preparation
Prior art date
Application number
BE154312A
Other languages
French (fr)
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 filed Critical
Priority to BE154312A priority Critical patent/BE826668A/en
Publication of BE826668A publication Critical patent/BE826668A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings

Landscapes

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

Description

       

  OMNIUM CHIMIQUE SOCIETE ANONYME

  
La présente invention se rapporte à la

  
 <EMI ID=1.1> 

  
propriétés vasodilatatrices et spasmolytiques , cardio:
latrices antiischèmiques.

  
La 3,14-dihydrocriocérine est un dérivé

  
 <EMI ID=2.1> 

  
structure est figurée ci-dessous
 <EMI ID=3.1> 
  <EMI ID=4.1> 

  
Ce produit est préparé à partir de la

  
 <EMI ID=5.1> 

  
 <EMI ID=6.1> 

  
demanderesse (Procédé de préparation de la dehydro-14, vincamine, de l'épi-16 déhydro-14,15 vincamine et de :  dérivés méthoxyles sur le noyau aromatique).

  
 <EMI ID=7.1> 

  
est traité par l'anhydride trifluoroacétique (réactioi polonovski) pour donner la criocérine (Bruneton et Al. Phytochemistry 14,569 (1975)).

  
La criocérine est alors selon l'inventj  traitée par un agent réducteur dans un alcool. L'ager réducteur peut être soit le borohydrure de sodium, soj

  
 <EMI ID=8.1> 

  
cool peut être soit le méthanol, l'éthanol, l'isopropc

  
 <EMI ID=9.1> 

  
non limitative, les caractéristiques de l'invention.

Exemple 1

  
5 g. de criocérine en solution dans 50 de méthanol sont agités 24 heures avec 5g. de borohydt

  
 <EMI ID=10.1> 

  
dilué par 200 ml. de chlorure de méthylène, puis 200 n d'eau distillée. La phase organique est décantée, lav à l'eau, séchée sur sulfate de sodium et évaporée à se vide. Le résidu est recristallisé dans le méthanol. obtient 2g.9 de 3,14 dihydrocriocérine

  
Fus. : 172-174[deg.]C

  
 <EMI ID=11.1> 

  
 <EMI ID=12.1> 

  
280 (3,83); 288 (3,71)

  
 <EMI ID=13.1> 



  OMNIUM CHEMICAL LIMITED COMPANY

  
The present invention relates to the

  
 <EMI ID = 1.1>

  
vasodilator and spasmolytic properties, cardio:
anti-ischemic latrices.

  
3,14-dihydrocriocerine is a derivative

  
 <EMI ID = 2.1>

  
structure is shown below
 <EMI ID = 3.1>
  <EMI ID = 4.1>

  
This product is prepared from

  
 <EMI ID = 5.1>

  
 <EMI ID = 6.1>

  
Applicant (Process for the preparation of dehydro-14, vincamine, epi-16 dehydro-14,15 vincamine and of: methoxyl derivatives on the aromatic nucleus).

  
 <EMI ID = 7.1>

  
is treated with trifluoroacetic anhydride (polonovski reaction) to give criocerin (Bruneton et al. Phytochemistry 14,569 (1975)).

  
The criocerin is then according to the invention treated with a reducing agent in an alcohol. The reducing ager can be either sodium borohydride, soj

  
 <EMI ID = 8.1>

  
cool can be either methanol, ethanol, isopropc

  
 <EMI ID = 9.1>

  
without limitation, the characteristics of the invention.

Example 1

  
5 g. of criocerine dissolved in 50 ml of methanol are stirred for 24 hours with 5 g. by borohydt

  
 <EMI ID = 10.1>

  
diluted by 200 ml. of methylene chloride, then 200 n of distilled water. The organic phase is decanted, washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is recrystallized from methanol. obtains 2g. 9 of 3.14 dihydrocriocerine

  
Fus. : 172-174 [deg.] C

  
 <EMI ID = 11.1>

  
 <EMI ID = 12.1>

  
280 (3.83); 288 (3.71)

  
 <EMI ID = 13.1>

Claims (1)

<EMI ID=14.1> <EMI ID = 14.1> Exemple 2 Example 2 5g. de criocérine en solution dans 50 de méthanol sont hydrogénés en présence de lg. de cha palladié à 5 %, à température et pression ordinaires, agitation. La quantité théorique d'hydrogène est abs en 2 heures. Le catalyseur est alors éliminé par fil tion sur Kieselghur et le filtrat distillé à sec four 4,8g. de dérivé hydrogéné sous forme d'une laque tran cide qui donne, par cristallisation dans le méthanol, 3,14 dihydrocriocérine. 5g. of criocerine in solution in 50 of methanol are hydrogenated in the presence of lg. of cha palladium at 5%, at ordinary temperature and pressure, stirring. The theoretical quantity of hydrogen is absent in 2 hours. The catalyst is then removed by filtration through Kieselghur and the filtrate distilled off in a dry oven 4.8 g. of hydrogenated derivative in the form of a transparent lacquer which gives, by crystallization from methanol, 3.14 dihydrocriocerine. Mêmes constantes que dans l'exemple 1. Same constants as in Example 1. REVENDICATIONS 1. A titre de nouvel alcaloïde indoli <EMI ID=15.1> 1. As a new indoli alkaloid <EMI ID = 15.1> synthèse du type vincamine et dont la structure figur <EMI ID=16.1> <EMI ID=17.1> synthesis of the vincamine type and whose structure figur <EMI ID = 16.1> <EMI ID = 17.1> 2. Procédé de préparation de l'alcalo suivant la revendication 1, caractérisé en ce que cet préparation à lieu à partir de la A 14,15 vincamine ece que le dérivé N-oxyde de la A 14,15 vincamine est 1 par l'anhydride trifluoroacétique pour donner la crio&#65533; 2. Process for the preparation of the alkali according to claim 1, characterized in that this preparation takes place from A 14.15 vincamine ece that the N-oxide derivative of A 14.15 vincamine is 1 by the trifluoroacetic anhydride to give crio &#65533; 3. Procédé suivant la revendication 2, caractérisé en ce que la A 14,15 vincamine est obtenu. 3. Method according to claim 2, characterized in that the A 14.15 vincamine is obtained. <EMI ID=18.1> <EMI ID = 18.1> 26 juillet 1974 de la demanderesse (procédé de prépare de la déhydro-14,15 vincamine de l'épi-16 déhydro-14,: vincamine et de leurs dérivés méthoxylés sur le noyau matique). July 26, 1974 by the Applicant (process for preparing dehydro-14,15 vincamine from epi-16 dehydro-14 ,: vincamine and their derivatives methoxylated on the matic nucleus). 4. Procédé suivant la revendication 2 caractérisé en ce que la criocérine est ensuite traite par un agent réducteur dans un alcool, cet agent réduc pouvant être soit le borohydrure de sodium, soit le bc hydrure de potassium, soit le charbon palladié et l'a] pouvant être soit le méthanol, l'éthanol, l'isopropanc 4. A method according to claim 2 characterized in that the criocerin is then treated with a reducing agent in an alcohol, this reducing agent can be either sodium borohydride or potassium hydride or palladium on charcoal and a ] which can be either methanol, ethanol, isopropanc
BE154312A 1975-03-14 1975-03-14 3,14-DIHYDROCRIOCERINE AND METHOD OF PREPARATION. BE826668A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BE154312A BE826668A (en) 1975-03-14 1975-03-14 3,14-DIHYDROCRIOCERINE AND METHOD OF PREPARATION.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BE826668 1975-03-14
BE154312A BE826668A (en) 1975-03-14 1975-03-14 3,14-DIHYDROCRIOCERINE AND METHOD OF PREPARATION.

Publications (1)

Publication Number Publication Date
BE826668A true BE826668A (en) 1975-06-30

Family

ID=25648453

Family Applications (1)

Application Number Title Priority Date Filing Date
BE154312A BE826668A (en) 1975-03-14 1975-03-14 3,14-DIHYDROCRIOCERINE AND METHOD OF PREPARATION.

Country Status (1)

Country Link
BE (1) BE826668A (en)

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