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FR2519986A1

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[5][_]
Molecule
(29/ 88)
[6][_]
piperazine
(28)
[7][_]
BENZODIOXINE
(10)
[8][_]
chloromethyl-6-benzodioxine
(7)
[9][_]
(benzodioxinyl-6-methyl)-1-piperazine
(6)
[10][_]
dihydrochloride
(4)
[11][_]
formyl-6-benzodioxine
(3)
[12][_]
thiadiazol
(3)
[13][_]
methanol
(2)
[14][_]
chloro-2-pyridine
(2)
[15][_]
ethanol
(2)
[16][_]
oxadiazol
(2)
[17][_]
carbon
(2)
[18][_]
CF
(1)
[19][_]
DES
(1)
[20][_]
dihydrochloride dihydrate
(1)
[21][_]
thiazole
(1)
[22][_]
chloro-2-thiadiazole
(1)
[23][_]
chloro-2-pyrazine
(1)
[24][_]
perazine
(1)
[25][_]
methoxy-6-chloro-2-pyridine
(1)
[26][_]
chloro-5-oxadiazole
(1)
[27][_]
methyl-4-triazol
(1)
[28][_]
chloro-3-methyl-4-triazole
(1)
[29][_]
triazol
(1)
[30][_]
oxygen
(1)
[31][_]
nitrogen
(1)
[32][_]
sulfur
(1)
[33][_]
chlorine
(1)
[34][_]
bromine
(1)
[35][_]
Substituent
(17/ 40)
[36][_]
benzodioxinyl-6-methyl
(12)
[37][_]
pyridyl
(4)
[38][_]
thiazol-1,3-yl
(4)
[39][_]
methyl
(3)
[40][_]
pyrazinyl
(2)
[41][_]
methyl-14-pyridyl
(2)
[42][_]
formyl
(2)
[43][_]
pyrimidinyl
(2)
[44][_]
methyl-4-pyridyl
(1)
[45][_]
methoxy-6-pyridyl
(1)
[46][_]
oxadiazol-1,2,4-yl
(1)
[47][_]
triazol-1,2,4-Yl
(1)
[48][_]
thiazolyl
(1)
[49][_]
thiadiazolyl
(1)
[50][_]
oxadiazolyl
(1)
[51][_]
triazolyl
(1)
[52][_]
thiadiazol-1,3,4-yl
(1)
[53][_]
Generic
(12/ 25)
[54][_]
radical
(5)
[55][_]
alkyl
(4)
[56][_]
alkoxy
(4)
[57][_]
HETEROcyclic
(2)
[58][_]
salts
(2)
[59][_]
halogen
(2)
[60][_]
five- or six-membered heterocyclic
(1)
[61][_]
acid addition salts
(1)
[62][_]
addition salts
(1)
[63][_]
acids
(1)
[64][_]
aldehyde
(1)
[65][_]
alkali metal
(1)
[66][_]
Gene Or Protein
(5/ 9)
[67][_]
DANS
(3)
[68][_]
LEURS
(2)
[69][_]
Pyri
(2)
[70][_]
CES
(1)
[71][_]
ETRE
(1)
[72][_]
Physical
(3/ 6)
[73][_]
4 l
(3)
[74][_]
3,4 l
(2)
[75][_]
2 N
(1)
[76][_]
Disease
(2/ 2)
[77][_]
Psychoses
(1)
[78][_]
Rale
(1)
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Publication
_________________________________________________________________
Number FR2519986A1
Family ID 5111953
Probable Assignee Adir Srl
Publication Year 1983
Title
_________________________________________________________________
FR Title NOUVEAUX DERIVES DE BENZODIOXINE, LEURS PROCEDES DE
PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES LES RENFERMANT
Abstract
_________________________________________________________________
Benzodioxine compounds of the formula: in which Het is a five- or
six-membered heterocyclic radical containing from one to three hetero
atoms, and from one to three double bonds, optionally substituted by
one or more alkyl or alkoxy radicals each from C1 to C5. These
compounds and physiologically tolerable acid addition salts thereof
may be used as medicines, especially in the treatment of psychoses.
<P>NOUVEAUX DERIVES DE BENZODIOXINE, UTILISABLES COMME MEDICAMENT ET
REPONDANT A LA FORMULE GENERALE:
(CF DESSIN DANS BOPI)
DANS LAQUELLE HET EST UN RADICAL HETEROcyclic PENTA- OU HEXAGONAL
CONTENANT DE UNE A TROIS DOUBLES LIAISONS ET DE UN A TROIS
HETEROATOMES EVENTUELLEMENT SUBSTITUE PAR UN OU PLUSIEURS RADICAUX
ALKyl OU ALKOXY DE C A C.</P><P>CES NOUVEAUX COMPOSES ET LEURS salts
PHYSIOLOGIQUEMENT TOLERABLES PEUVENT ETRE UTILISES EN THERAPEUTIQUE,
NOTAMMENT DANS LE TRAITEMENT DES TROUBLES EXTRAPYRAMIDAUX.</P>
Description
_________________________________________________________________
La presente invention a pour objet des derives de benzodioxine, leurs
procedes de preparation et leur ap- plication en therapeutique.
Elle concerne particulierement les derives de benzodioxine de formule
generale: o (250 C avec decomposi- tion (methanol anhydre), a partir:
de chloromethyl-6-benzodioxine et de (pyridyl-2)-1 piperazine, ou de
chloro-2-pyridine et de (benzodioxinyl-6-methyl)-1-piperazine, ou de
formyl-6-benzodioxine et de (pyridyl-2)-1 piperazine.
3) (benzodioxinyl-6-methyl)-I (thiazol-1,3-yl-2)-4 piperazine, P F de
son dihydrochloride dihydrate and #x003E; 220 C (methanol anhydre) a
partir: -_ de chloromethyl-6-benzodioxine et de (thiazol-1,3-yl-2)-1
piperazine, ou -8 de ohloro-2 thiazole-1,3 et de
(benzodioxinyl-6-methyl)-1-piperazine, ou
-de formyl-6-benzodioxine et de (thiazol-1,3-yl-2)-l piperazine. 41)
(benzodioxinyl-6-methyl)-l (thiadiazol-1, 3, 4 l yl-2)-4 piperazine,
P' F de son dichlorbydrate and #x003E; 250 OC avec de- coimposition-
and #x003C;ethanol anhydre), a partir de chloromethyl-6-benzodioxine
et de (thiadiazol-1,3,4 l yl-2)-l piperazine, ou de
chloro-2-thiadiazole-1,3,4 l et de
(benzodioxinyl-6-methyl)-1-piperazine, ou de tormyl-6 benzodioxine et
de (thiadiazol-1,3,4 I yl-2)-l piperazine.) 2580 C avec decomposition
(ethanol anhydre), a partir de chloromethyl-6-benzodioxine et de
(pyrazinyl-2)-l -piperazine, ou -de chloro-2-pyrazine et de
(benzodioxinyl-6-methyl)-l p 1 perazine, ou
-deformyl-6 benzodioxine et de (pyrazinyl'-2)-l piperazine.
6) and #x003C;benzodioxinyl-6-methyl)-l(methyl-14-pyridyl-2)-4 l
piperazine, a partir: de chloromethyl-6-benzodioxine et de
(methyl-14-pyridyl-2)-l piperazine, ou -de methyl-4 l
chloro-2-pyridine et de (benzodioxinyl-6-methyl)-1-piperazine, ou de
formyl-6-benzodioxine et de (methyl-4-pyridyl-2)-l piperazine.
7) and #x003C;benzodioxinyl-6-methyl)-1 (methoxy-6-pyridyl-2)-4
piperazIne, apartir
-519986
-9-
-de chloromethyl-6-benzodioxine et de (mnethoxy-6 pyri- dyl-2)-l
piperazine, ou de methoxy-6-chloro-2-pyridine et de
(benzodioxinyl-6-methyl)-1-piperazine, ou -de formyl-,6 benzodioxirne
et de (methoxye-6 pyridyl-2)-1 piperazine. 8)
(benzodioxinyl-6-methyl)-l (oxadiazol-1,2,4-yl-5)- 14 piperazine, a
partir: de ohloromethyl-6 benzodioxine et d'(oxadiazol-1,2,4 I yl-5)-l
piperazine, ou de chloro-5-oxadiazole-1,2,41 et de
(benzodioxinyl-6-methyl)-1-piperazine, ou de formyl-6 benzodioxinie et
d'(oxadiazol-1,2-4 yl5)-l pipeerazinie. 9) (benzodioxinyl-6-methyl)-1
(methyl-4 I triazol-1,2,4-Yl-3)-4 piperazine, a partir: de
chloromethyl-6-benzodioxine et de (methyl-4-triazol-1,2 I 4 Yl-3)-l
piperazirne, ou de chloro-3-methyl-4-triazole-1,2,4 et de and
#x003C;benzodioxinyl-6-methyl)-1 piperazine, ou de tormyl6
benzodioxine-2 et de (methyl-4 t triazol-1,2,41
Yl-3)-l piperazine.
* 519986
-
Claims
_________________________________________________________________
REVENDICATIONS
1) Les derives de benzodioxine de formule generale: CH 2 Het I dans
laquelle Het represente un radical heterocyclic penta ou hexagonal
comprenant de une a trois dou- bles liaisons et de un a trois
heteroatomes tels que les atomes d'oxygen d'nitrogen et de sulfur, et
eventuellement substitue par un ou plusieurs radicaux alkyl ou alkoxy
contenant chacun de 1 a 5 atomes de carbon.
2) Les composes de la revendication 1 de formule generale I dans
laquelle Het represente un radical pyri- dyle, pyrimidinyl, pyrazinyl,
thiazolyl, thiadiazolyl, oxadiazolyl ou triazolyl, ou un de ces
radicaux substi- tue par un ou plusieurs groupes alkyl ou alkoxy ayant
chacun de 1 a 5 atomes de carbon.
3) Les addition salts des composes selon les reven- dications 1 et 2
avec des acidsappropries.
4) Les salts selon la revendication 3 qui sont physio- logiquement
tolerables.
5) La (benzodioxinyl-6-methyl)-1 (pyrimidinyl-2)-4 piperazine et son
dihydrochloride.
6) La (benzodioxinyl-6-methyl)-1 (pyridyl-2)-4 piperazine et son
dihydrochloride. 11 -
7) La (benzodioxinyl-6-methyl)-1, (thiazol-1,3-yl-2)-4 piperazine et
son dihydrochloride.
8) La (benzodioxinyl-6-methyl)-1 (thiadiazol-1,3,4-yl-2)-4 piperazine
et son dihydrochloride.
9) Un procede de preparation des composes de la revendication 1,
caracterise en ce que l'on condense un derive halogen de formule
generale: CH 2 Hal II dans laquelle Hal est un atome de chlorine ou de
bromine, avec une piperazine N-monosubstituee de formule gene- rale:
EN J Het III dans laquelle Het a la signification definie dans la
revendication 1.
10) Un procede de preparation des composes de la revendication 1,
caracterise en ce que l'on condense un derive halogen de formule
generale: Het-Hal IV dans laquelle Het et Hal ont les significations
e- noncees respectivement dans les revendications 1 et 9, avec une
piperazine N-monosubstituee de formule: 12 - C CH 2 N H V
11) Un procede de preparation des composes de la revendication 1,
caracterise en ce que l'on soumet un melange de l'aldehyde de formule
H O v C== and #x003E; VI et d'une piperazine N-monosubstituee de
formule generale III telle que definie dans la revendication 9, a une
alkylation reductive a l'aide d'un cyanoborohy- drure de formule BH 3
CN M dans laquelle M represente un alkali metal.
12) Les compositions pharmaceutiques contenant comme principe actif au
moins un compose selon les revendications 1, 2 et 4 a 8 avec les
supports pharmaceutiques appropries.
13) Les compositions pharmaceutiques selon la reven- dication 12
presentees sous une forme convenant pour l'administration par voie
orale, rectale ou parenterale, notamment dans le traitement des
troubles extrapyramidaux.
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