BE651900A - - Google Patents

Info

Publication number
BE651900A
BE651900A BE651900DA BE651900A BE 651900 A BE651900 A BE 651900A BE 651900D A BE651900D A BE 651900DA BE 651900 A BE651900 A BE 651900A
Authority
BE
Belgium
Prior art keywords
emi
compounds
general formula
straight
branched
Prior art date
Application number
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
Publication of BE651900A publication Critical patent/BE651900A/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring

Landscapes

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

Description

  

   <EMI ID=1.1> 

  
 <EMI ID=2.1> 

  
2  
 <EMI ID=3.1> 
 <EMI ID=4.1> 

  
indépendante l'un de l'autre des atomes d'hydrogène ou des

  
 <EMI ID=5.1> 

  
A représente un groupe hydrocarbure aliphatiqua saturé ou non satura à chaîne droite ou ramifiée comportant 2 à 8 atomes de carbone; m est un nombre entier compris entre

  
 <EMI ID=6.1> 

  
composés ont des propriétés thérapeutiques précieuses, ils

  
 <EMI ID=7.1> 

  
Les composés Médicamenteux ayant la formula généra-

  
 <EMI ID=8.1> 

  
 <EMI ID=9.1> 

  

 <EMI ID=10.1> 


  
 <EMI ID=11.1> 

  

 <EMI ID=12.1> 
 

  
 <EMI ID=13.1> 

  

 <EMI ID=14.1> 


  
 <EMI ID=15.1> 

  
la formule générale V : , 

  

 <EMI ID=16.1> 


  
 <EMI ID=17.1> 

  
mélange réactionnel. La décomposition du complexe obtenu

  
 <EMI ID=18.1>  d'un agent alcalin de condensation, par exemple d'amidure de sodium, 

  
Selon une autre caractéristique de l'invention, on

  
 <EMI ID=19.1> 

  
 <EMI ID=20.1> 

  

 <EMI ID=21.1> 


  
 <EMI ID=22.1> 

  
 <EMI ID=23.1> 

  
 <EMI ID=24.1> 

  

 <EMI ID=25.1> 


  
 <EMI ID=26.1> 

  
vin 

  

 <EMI ID=27.1> 


  
 <EMI ID=28.1> 

  
 <EMI ID=29.1> 

  
tient do la façon précitée;: peuvent être transformée par

  
 <EMI ID=30.1> 

  

 <EMI ID=31.1> 


  
représenta un groupe amino cyclique substi-

  
tué

  
1 &#65533;,. 

  
 <EMI ID=32.1> 

  

 <EMI ID=33.1> 


  
 <EMI ID=34.1>  <EMI ID=35.1> 

  
 <EMI ID=36.1> 

  

 <EMI ID=37.1> 


  
 <EMI ID=38.1> 

  
en position 4 du noyau pi-pérazinique.

  
 <EMI ID=39.1> 

  
présentent des propriétés pharmacologiques très avantagea-  ses. leur caractéristique la plus importante réside dans <EMI ID=40.1>   <EMI ID=41.1> 

  
en même temps leur toxicité et leur pouvoir de liaison 

  
 <EMI ID=42.1> 

  
ne; en outre, leur pouvoir de résorption orale est bien

  
 <EMI ID=43.1> 

  
 <EMI ID=44.1> 

  
 <EMI ID=45.1> 

  
veaux, essayée sur des fragments .de tissu intestinal, est

  
 <EMI ID=46.1> 

  
excellente sur des tissas' intestinaux isoles du cochon

  
 <EMI ID=47.1>  composes conformes à l'invention ne sont même liés sur une <EMI ID=48.1>   <EMI ID=49.1> 

  
chez le cochon d'inde selon Brock et Lorenz une action spasmolytique similaire à l'activité do la papavérine con-

  
 <EMI ID=50.1> 

  
cardiogrammes. Des doses de 1,5 mg/kg in vivo augmentent la circulation sanguine du chien dans l'artère coronaire

  
 <EMI ID=51.1> 

  
n'exercent pas d'influence notable sur les transmissions

  
 <EMI ID=52.1> 

  
nerveux central; leur effet d'inhibition sur la motilité spontanée et l'excitation causée par l'amphétamine, ainsi que leur effet dépressif sur la, température est d'une im-

  
 <EMI ID=53.1> 

  
tranquillisants faibles; la doce nécessaire pour obtenir .1 <EMI ID=54.1> 

  
spasmolytiques efficaces. 

  
Ces nouveaux composés ont également ces' effets 

  
 <EMI ID=55.1> 

  
anesthésiques local en surface n'est pas important. Cer- <EMI ID=56.1> 

  
Les nouveaux composes de la formule générale 1 peuvent être utilises en thérapie tels que sous forme de leurs sels avec. des acides miné*-aux ou organiques acceptables en pharmacie. Ces composés ^peuvent être administrés par voie orale, parentale ou rectale sous forme de compositions habituelles pharmaceutiques, -ces dernières pouvant conte. nir les ingrédients actifs précités seuls ou en combinai-

  
 <EMI ID=57.1> 

  
ques courants ou d'autres additifs et, en outre éventuellement avec d'autres ingrédients actifs en thérapie qui peuvent accentuer l'effet des composés nouveaux conformée  l'invention. les compositions pharmaceutiques peuvent être obtenues sous forme de comprimés ou de dragées enrobés con-

  
 <EMI ID=58.1> 

  
On va'décrire maintenant en détail le procédé de préparation conforme à l'invention,

  
 <EMI ID=59.1> 

  
 <EMI ID=60.1>   <EMI ID=61.1> 

  
 <EMI ID=62.1> 

  
 <EMI ID=63.1>   <EMI ID=64.1> 

  
 <EMI ID=65.1> 

  
 <EMI ID=66.1> 

  
Le chlorhydrate du produite recristallisé dans un

  
 <EMI ID=67.1> 

  
chloro-propane ; on chauffe ce composé modérément dans un 

  
 <EMI ID=68.1>  

  
 <EMI ID=69.1> 

  
la produit obtenu et on distille sous vide on obtient ainsi

  
 <EMI ID=70.1> 

  
décompose complexe par addition d'une solution de ' 

  
 <EMI ID=71.1> 

  
 <EMI ID=72.1> 

  
 <EMI ID=73.1> 

  
 <EMI ID=74.1>   <EMI ID=75.1>   <EMI ID=76.1>  

  
 <EMI ID=77.1> 

  
 <EMI ID=78.1> 

  
le laisse reposer la nuit et on décompose finalement le 

  
 <EMI ID=79.1> 

  
'-Boue forme d'une  huile jaune pâle qui bout à 141 - 1440 sous-une pression 

  
 <EMI ID=80.1> 

  
 <EMI ID=81.1> 

  
 <EMI ID=82.1> 

  
 <EMI ID=83.1> 

  
 <EMI ID=84.1>   <EMI ID=85.1> 

  
on le laisse reposer une nuit et on décomposa le complexe

  
 <EMI ID=86.1> 

  
on extrait le phase aqueuse avec de l'éther et on évapora les extraits éthérés combinés-, juin on fractionne le réel-

  
 <EMI ID=87.1> 

  
 <EMI ID=88.1> 

  
'

  
 <EMI ID=89.1>   <EMI ID=90.1>  . mélange pendant 3 heures,!! on le laisse reposer pendant une  <EMI ID=91.1> 

  
 <EMI ID=92.1> 

  
aqueuse avec de l'éther et on évapore les extraits combi- 

  
 <EMI ID=93.1> 

  
 <EMI ID=94.1> 

  
 <EMI ID=95.1> 

  
 <EMI ID=96.1> 

  
 <EMI ID=97.1> 

  
 <EMI ID=98.1> 

  
 <EMI ID=99.1>   <EMI ID=100.1> 

  
 <EMI ID=101.1> 

  
 <EMI ID=102.1> 

  
 <EMI ID=103.1> 

  
Par recristallisation dans de l'essence légère on obtient des cristaux blancs sous force d'aiguilles qui ont un point

  
 <EMI ID=104.1> 

  
 <EMI ID=105.1> 



   <EMI ID = 1.1>

  
 <EMI ID = 2.1>

  
2
 <EMI ID = 3.1>
 <EMI ID = 4.1>

  
independent from each other of hydrogen atoms or

  
 <EMI ID = 5.1>

  
A represents a straight or branched chain saturated or unsaturated aliphatic hydrocarbon group having 2 to 8 carbon atoms; m is an integer between

  
 <EMI ID = 6.1>

  
compounds have valuable therapeutic properties, they

  
 <EMI ID = 7.1>

  
Medicinal compounds having the general formula

  
 <EMI ID = 8.1>

  
 <EMI ID = 9.1>

  

 <EMI ID = 10.1>


  
 <EMI ID = 11.1>

  

 <EMI ID = 12.1>
 

  
 <EMI ID = 13.1>

  

 <EMI ID = 14.1>


  
 <EMI ID = 15.1>

  
the general formula V:,

  

 <EMI ID = 16.1>


  
 <EMI ID = 17.1>

  
reaction mixture. The decomposition of the complex obtained

  
 <EMI ID = 18.1> of an alkaline condensing agent, for example sodium amide,

  
According to another characteristic of the invention, it is

  
 <EMI ID = 19.1>

  
 <EMI ID = 20.1>

  

 <EMI ID = 21.1>


  
 <EMI ID = 22.1>

  
 <EMI ID = 23.1>

  
 <EMI ID = 24.1>

  

 <EMI ID = 25.1>


  
 <EMI ID = 26.1>

  
wine

  

 <EMI ID = 27.1>


  
 <EMI ID = 28.1>

  
 <EMI ID = 29.1>

  
takes the aforementioned way ;: can be transformed by

  
 <EMI ID = 30.1>

  

 <EMI ID = 31.1>


  
represented a cyclic amino group substituted

  
kill

  
1 &#65533;,.

  
 <EMI ID = 32.1>

  

 <EMI ID = 33.1>


  
 <EMI ID = 34.1> <EMI ID = 35.1>

  
 <EMI ID = 36.1>

  

 <EMI ID = 37.1>


  
 <EMI ID = 38.1>

  
in position 4 of the pi-perazin nucleus.

  
 <EMI ID = 39.1>

  
exhibit very advantageous pharmacological properties. their most important feature is <EMI ID = 40.1> <EMI ID = 41.1>

  
at the same time their toxicity and their binding power

  
 <EMI ID = 42.1>

  
born; in addition, their power of oral absorption is well

  
 <EMI ID = 43.1>

  
 <EMI ID = 44.1>

  
 <EMI ID = 45.1>

  
calves, tested on fragments of intestinal tissue, is

  
 <EMI ID = 46.1>

  
excellent on isolated intestinal tissues from pigs

  
 <EMI ID = 47.1> compounds according to the invention are not even linked on an <EMI ID = 48.1> <EMI ID = 49.1>

  
in the guinea pig according to Brock and Lorenz a spasmolytic action similar to the activity of papaverine con-

  
 <EMI ID = 50.1>

  
cardiograms. Doses of 1.5 mg / kg in vivo increase the blood circulation of the dog in the coronary artery

  
 <EMI ID = 51.1>

  
do not exert any significant influence on the transmissions

  
 <EMI ID = 52.1>

  
central nervous; their inhibiting effect on spontaneous motility and arousal caused by amphetamine, as well as their depressive effect on temperature is immeasurably

  
 <EMI ID = 53.1>

  
weak tranquilizers; the doce necessary to obtain .1 <EMI ID = 54.1>

  
effective spasmolytics.

  
These new compounds also have these '

  
 <EMI ID = 55.1>

  
local anesthetics on the surface is not important. Cer- <EMI ID = 56.1>

  
The novel compounds of the general formula 1 can be used in therapy such as in the form of their salts with. pharmacy acceptable mineral or organic acids. These compounds can be administered orally, parentally or rectally in the form of customary pharmaceutical compositions, the latter possibly containing. the aforementioned active ingredients alone or in combination

  
 <EMI ID = 57.1>

  
currents or other additives and also optionally with other active ingredients in therapy which may enhance the effect of the new compounds according to the invention. the pharmaceutical compositions can be obtained in the form of tablets or coated dragees con-

  
 <EMI ID = 58.1>

  
The preparation process according to the invention will now be described in detail,

  
 <EMI ID = 59.1>

  
 <EMI ID = 60.1> <EMI ID = 61.1>

  
 <EMI ID = 62.1>

  
 <EMI ID = 63.1> <EMI ID = 64.1>

  
 <EMI ID = 65.1>

  
 <EMI ID = 66.1>

  
The hydrochloride of the product recrystallized in a

  
 <EMI ID = 67.1>

  
chloropropane; this compound is heated moderately in a

  
 <EMI ID = 68.1>

  
 <EMI ID = 69.1>

  
the product obtained and distilled under vacuum thus obtaining

  
 <EMI ID = 70.1>

  
decomposes complex by adding a solution of '

  
 <EMI ID = 71.1>

  
 <EMI ID = 72.1>

  
 <EMI ID = 73.1>

  
 <EMI ID = 74.1> <EMI ID = 75.1> <EMI ID = 76.1>

  
 <EMI ID = 77.1>

  
 <EMI ID = 78.1>

  
let it sit overnight and we finally break down the

  
 <EMI ID = 79.1>

  
'-Mud form of a pale yellow oil which boils at 141 - 1440 under pressure

  
 <EMI ID = 80.1>

  
 <EMI ID = 81.1>

  
 <EMI ID = 82.1>

  
 <EMI ID = 83.1>

  
 <EMI ID = 84.1> <EMI ID = 85.1>

  
we let it stand overnight and we decompose the complex

  
 <EMI ID = 86.1>

  
the aqueous phase is extracted with ether and the combined ethereal extracts are evaporated off - the real - is fractionated.

  
 <EMI ID = 87.1>

  
 <EMI ID = 88.1>

  
'

  
 <EMI ID = 89.1> <EMI ID = 90.1>. mixing for 3 hours, !! let it sit for an <EMI ID = 91.1>

  
 <EMI ID = 92.1>

  
aqueous with ether and the combined extracts evaporated.

  
 <EMI ID = 93.1>

  
 <EMI ID = 94.1>

  
 <EMI ID = 95.1>

  
 <EMI ID = 96.1>

  
 <EMI ID = 97.1>

  
 <EMI ID = 98.1>

  
 <EMI ID = 99.1> <EMI ID = 100.1>

  
 <EMI ID = 101.1>

  
 <EMI ID = 102.1>

  
 <EMI ID = 103.1>

  
By recrystallization in light gasoline, white crystals are obtained under the force of needles which have a point

  
 <EMI ID = 104.1>

  
 <EMI ID = 105.1>

Claims (1)

<EMI ID=106.1> <EMI ID = 106.1> <EMI ID=107.1> <EMI ID = 107.1> <EMI ID=108.1> <EMI ID = 108.1> <EMI ID=109.1> <EMI ID = 109.1> <EMI ID=110.1> <EMI ID = 110.1> <EMI ID=111.1> <EMI ID = 111.1> <EMI ID=112.1> <EMI ID = 112.1> ré à chaîne droite où ramifiée'et à 2 à 8 atomes de car- bone: m est un nombre entier compris entre 0 et 4 et n D straight chain or branched 'and 2 to 8 carbon atoms: m is an integer between 0 and 4 and n <EMI ID=113.1> <EMI ID = 113.1> <EMI ID=114.1> <EMI ID = 114.1> <EMI ID=115.1> <EMI ID = 115.1> <EMI ID=116.1> <EMI ID=117.1> <EMI ID = 116.1> <EMI ID = 117.1> <EMI ID=118.1> <EMI ID = 118.1> <EMI ID=119.1> <EMI ID = 119.1> <EMI ID=120.1> <EMI ID = 120.1> <EMI ID=121.1> <EMI ID = 121.1> <EMI ID=122.1> <EMI ID = 122.1> <EMI ID=123.1> <EMI ID = 123.1> <EMI ID=124.1> <EMI ID = 124.1> <EMI ID=125.1> <EMI ID = 125.1> <EMI ID=126.1> <EMI ID=127.1> <EMI ID = 126.1> <EMI ID = 127.1> <EMI ID=128.1> <EMI ID = 128.1> <EMI ID=129.1> <EMI ID = 129.1> <EMI ID=130.1> <EMI ID = 130.1> ques ou différents, puis on fait réagir l'éther obtenu qui ques or different, then react the ether obtained which <EMI ID=131.1> <EMI ID = 131.1> <EMI ID=132.1> <EMI ID = 132.1> <EMI ID=133.1> <EMI ID = 133.1> <EMI ID=134.1> <EMI ID = 134.1> <EMI ID=135.1> <EMI ID = 135.1> <EMI ID=136.1> dérivés du type cycloalkanol ayant la formule générale <EMI ID = 136.1> derivatives of the cycloalkanol type having the general formula <EMI ID=137.1> <EMI ID = 137.1> <EMI ID=138.1> <EMI ID=139.1> <EMI ID = 138.1> <EMI ID = 139.1> ré ou non &#65533;aturé à chaîne droite ou ramifiée comportant D or not &#65533; atured straight or branched chain comprising <EMI ID=140.1> <EMI ID = 140.1>
BE651900D 1963-08-18 1964-08-17 BE651900A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HUEE001033 1963-08-18

Publications (1)

Publication Number Publication Date
BE651900A true BE651900A (en) 1964-12-16

Family

ID=10995158

Family Applications (1)

Application Number Title Priority Date Filing Date
BE651900D BE651900A (en) 1963-08-18 1964-08-17

Country Status (6)

Country Link
AT (1) AT264495B (en)
BE (1) BE651900A (en)
DE (1) DE1443813A1 (en)
FR (1) FR4468M (en)
NL (1) NL6409519A (en)
SE (1) SE334349B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1792788A1 (en) * 1966-01-15 1976-10-21 Egyt Gyogyszervegyeszeti Gyar PERIPHERALLY VASODILATORY MEDICINAL PRODUCT
DE1618297C3 (en) 1966-01-15 1977-03-10 Egyt Gyogyszervegyeszeti Gyar, Budapest Process for the production of basic ethers

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU179164B (en) * 1979-12-14 1982-08-28 Egyt Gyogyszervegyeszeti Gyar Process for producing cycloalkyl-ethers of alkanolamines
US12274703B2 (en) 2017-12-21 2025-04-15 Gliapharm Sa Compositions and methods of treatment for neurological disorders comprising a dementia
US12310967B2 (en) 2017-12-21 2025-05-27 Gliapharm Sa Compositions and methods of treatment for neurological disorders comprising motor neuron diseases
WO2020132378A2 (en) 2018-12-22 2020-06-25 Gliapharm Sa Compositions and methods of treatment for neurological disorders comprising depression

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1792788A1 (en) * 1966-01-15 1976-10-21 Egyt Gyogyszervegyeszeti Gyar PERIPHERALLY VASODILATORY MEDICINAL PRODUCT
DE1618297C3 (en) 1966-01-15 1977-03-10 Egyt Gyogyszervegyeszeti Gyar, Budapest Process for the production of basic ethers

Also Published As

Publication number Publication date
AT264495B (en) 1968-09-10
SE334349B (en) 1971-04-26
NL6409519A (en) 1965-02-19
DE1443813A1 (en) 1968-11-28
FR4468M (en) 1966-10-03

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