FR2502621A1 - - Google Patents
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- FR2502621A1 FR2502621A1 FR8106171A FR8106171A FR2502621A1 FR 2502621 A1 FR2502621 A1 FR 2502621A1 FR 8106171 A FR8106171 A FR 8106171A FR 8106171 A FR8106171 A FR 8106171A FR 2502621 A1 FR2502621 A1 FR 2502621A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
NOUVEAU PROCEDE DE PREPARATION DES PRODUITS DE FORMULE GENERALE (1): (CF DESSIN DANS BOPI)NEW PROCESS FOR THE PREPARATION OF GENERAL FORMULA (1): (CF DRAWING IN BOPI)
Description
-1 - La présente invention concerne un nouveau procédé de préparationThe present invention relates to a new preparation process
d'imidazobenzo-diazépines, ainsi que de leurs imidazobenzo-diazepines, as well as their
sels d'addition avec les acides.addition salts with acids.
L'invention a plus précisément pour objet un nouveau procédé de préparation des produits de formule générale: R R3 The subject of the invention is more specifically a new process for the preparation of the products of general formula: R 3 R 3
CH-N XCH-N X
R4 (I) R1 R2 dans laquelle R1 représente un.atome d'hydrogène, un atome d'halogène, un radical nitro ou un radical trifluorométhyle R2 représente un atome d'hydrogène ou un atome d'halogène R3 etR4 représentent ensemble avec l'atome d'azote auxquels Wherein R 1 represents a hydrogen atom, a halogen atom, a nitro radical or a trifluoromethyl radical R 2 represents a hydrogen atom or a halogen atom R 3 and R 4 represent together with nitrogen atom to which
ils sont liés un radical 4-alcoyl-pipérazin -1-yl, 4-cyclo- they are linked to a 4-alkylpiperazine-1-yl, 4-cycloalkyl radical.
alcoyl alcoyl pipérazin-1-yl, 4-phényl-pipérazin-lyl ou pipéridino, ainsi que de leurs sels d'addition avec les alkylpiperazin-1-yl, 4-phenylpiperazinyl or piperidino, as well as their addition salts with the
acides minéraux ou organiques.mineral or organic acids.
Dans la formule I et dans ce qui suit, In formula I and in the following,
- lorsque R1 représente un atome d'halogène, il s'agit de préfé- when R 1 represents a halogen atom, it is preferable
rence d'un atome de fluor, de chlore ou de brome et plus parti- fluorine, chlorine or bromine atom and, in particular,
culièrement d'un atome de chlore;especially a chlorine atom;
- lorsque R2 représente un atome d'halogène, il s'agit de pré- when R2 represents a halogen atom, it is a matter of
férence d'un atome de fluor, de chlore ou de brome, et plus particulièrement d'un atome de fluor ou de chlore. De plus lorsque R2 est un atome d'halogène, il est, de préférence, en position ortho; -lorsque R3 et R représentent ensemble avec l'atome d'azote 3.4 auxquels ils sont liés un radical 4-alcoyl-pipérazin-1-yl, il s'agit de préférence d'un radical 4-méthyl-pipérazin-1-yl 4 - éthyl-pipérazin-1-yl ou 4 -propyl- pipérazin 1-yl et plus particulièrement du radical 4 - méthyl-pipérazin-1- yl, lorsque R3 et R4 représentent ensemble avec l'atome d'azote preferably a fluorine, chlorine or bromine atom, and more particularly a fluorine or chlorine atom. In addition, when R2 is a halogen atom, it is preferably in the ortho position; when R 3 and R 3 together with the nitrogen atom 3 to which they are attached form a 4-alkylpiperazin-1-yl radical, it is preferably a 4-methyl-piperazin-1-yl radical; 4-ethyl-piperazin-1-yl or 4-propyl-piperazin-1-yl and more particularly the 4-methyl-piperazin-1-yl radical, when R3 and R4 together with the nitrogen atom represent
auxquels ils sont liés un radical 4 - cyclo-alcoyl alcoyl- to which they are bound is a 4-cycloalkylalkyl radical.
pipérazin-1-yl, il s'agit de préférence d'un radical cyclo piperazin-1-yl, it is preferably a cyclo radical
alcoyl comportant de 3 à 6 atomes de carbone tel que les radi- alkyl having from 3 to 6 carbon atoms such that the radicals
caux cyclopropyle, cyclobutyle ou cyclopentyle. Parmi lés radicaux 4 cyclo-alcoyl alcoyl-pipérazin-1-yl on retient cyclopropyl, cyclobutyl or cyclopentyl. Among the 4-cycloalkylalkyl-piperazin-1-yl radicals,
plus particulièrement le radical 4 - cyclopropyle méthyl- more particularly the radical 4-cyclopropyl methyl-
pipérazin-1-yl. Les sels d'addition avec les acides minéraux ou organiques peuvent être, par exemple, les sels formés avec les acides chlorhydrique, bromhydrique, iodhydrique,;nitrique, sulfurique, phosphorique, propionique, acétique, formique, piperazin-1-yl. The addition salts with inorganic or organic acids may be, for example, the salts formed with hydrochloric, hydrobromic, hydroiodic, nitric, sulfuric, phosphoric, propionic, acetic, formic acids,
benzo!que, maléique, fumarique, succinique, tartrique, citri- benzoic, maleic, fumaric, succinic, tartaric, citric,
que, oxalique, glyoxylique, aspartique, alcanesulfoniques tels que l'acide méthane sulfonique et arylsufoniques, tels as, oxalic, glyoxylic, aspartic, alkanesulfonic such as methanesulfonic acid and arylsufonic, such
que l'acide benzène sulfonique.as benzene sulfonic acid.
Les produits de formule générale (I) et leurs sels ainsi qu'un procédé de préparation de ceux-ci ont été décrits The products of general formula (I) and their salts and a process for the preparation thereof have been described.
dans le brevet français ne 2300 569 déposé par la demanderesse. in French Patent No. 2,300,569 filed by the Applicant.
Ainsi qu4il est indiqué dans ce brevet, les produits de formule générale (I) possèdent d'intéressantes propriétés As indicated in this patent, the products of the general formula (I) have interesting properties
sédatives, hypnotiques, anxiolytiques tranquillisantes, anti- sedatives, hypnotics, anxiolytic tranquillizers, anti-
convulsivantee et myorelaxantes.convulsive and muscle relaxants.
Le nouveau procédé de l'invention permet de prépa- The new method of the invention makes it possible to
rer les produits de la formule (I) avec de bons rendements en un nombre de stades inférieur à celui des procédés décrits the products of the formula (I) with good yields in a number of stages lower than that of the described processes.
dans le brevet français précité.in the aforementioned French patent.
La présente demande a ainsi pour objet un nouveau procédé de préparation des produits de formule générale I, ainsi que de leurs sels d'addition avec les acides minéraux ou organiques, caractérisé en ce que l'on fait réagir un produit de formule: - 2 - Rl (l The subject of the present application is therefore a new process for the preparation of the products of general formula I and their addition salts with mineral or organic acids, characterized in that a product of formula: - Rl (l
N â2N2
dans laquelle R1 et R2 ont la signification déjà indiquée, avec une amine de formule alkO in which R1 and R2 have the meaning already indicated, with an amine of formula alkO
CH - N(III)CH - N (III)
alkO / 4 dans laquelle alk représente un radical alcoyle renfermant de 1 à 3 atomes de carbone, R3 et R4 ont la signification déjà indiquée, au sein d'un solvant organique pour obtenir le produit de formule I recherché, que l'on peut salifier le cas échéant. Dans des conditions préférentielles de mise en oeuvre du procédé de l'invention, la réaction du produit de formule(II)avec le produit de formule(III)est effectuée au sein d'un solvant organique tel que le chlorure de méthylène alkO / 4 in which alk represents an alkyl radical containing from 1 to 3 carbon atoms, R3 and R4 have the meaning already indicated, in an organic solvent to obtain the desired product of formula I, which can be salified where appropriate. Under preferential conditions for carrying out the process of the invention, the reaction of the product of formula (II) with the product of formula (III) is carried out in an organic solvent such as methylene chloride.
et en présence d'une amine telle que la triéthylamine. and in the presence of an amine such as triethylamine.
Les sels d'addition avec les acides des produits de formule I peuvent être préparés en faisant réagir les dits produits de formule I avec une quantité stoéchiométrique d'un The acid addition salts of the products of formula I may be prepared by reacting said products of formula I with a stoichiometric amount of
acide minéral ou organique. La réaction est effectuée de pré- mineral or organic acid. The reaction is carried out pre-
férence dans un solvant organique ou un mélange de solvants organiques tel que les alcools, par exemple le méthanol ou l'éthanol, les halogénures d'alcoyle, par exemple, le chlorure in an organic solvent or a mixture of organic solvents such as alcohols, for example methanol or ethanol, alkyl halides, for example chloride
de méthylène.methylene.
Comme indiqué dans le brevet français n 2300 569 les produits de formule II peuvent être préparés au départ d'un produit de formule: S As indicated in French Patent No. 2,300,569, the products of formula II may be prepared starting from a product of formula:
-- C(IV)- C (IV)
0 R_, R20 R_, R2
dans laquelle R1 et R2 ont la signification déjà indiquée, par réaction avec la glycine pour obtenir un produit de formule: in which R1 and R2 have the meaning already indicated, by reaction with glycine to obtain a product of formula:
N NH-CH2 - COOHN NH-CH2 - COOH
R1, Cv) dans laquelle R1 et R2 ont la signification déjà indiquée, que l'on déshydrate pour obtenir le produit de formule (II) recherché. La déshydratation peut avantageusement être effectuée au R1, Cv) in which R1 and R2 have the meaning already indicated, which is dehydrated to obtain the product of formula (II) sought. Dehydration can advantageously be carried out at
moyen d'un carbodiimide tel que le dicyclohexyl carbodiimide. a carbodiimide such as dicyclohexyl carbodiimide.
Les produits de formule (II) lorsqu'ils ne sont pas connus, peuvent être préparés par réaction d'un produit de formule: The products of formula (II) when they are not known may be prepared by reacting a product of formula:
HN R3HN R3
H - N X (VI)-H - N X (VI) -
R4 dans laquelle R3 et R4 ont la signification déjà indiquée avec le diméthylcétal du diméthyl formamide. Un exemple d'une R4 in which R3 and R4 have the meaning already indicated with dimethylformamide dimethylketal. An example of a
telle préparation figure dans la partie expérimentale. such preparation appears in the experimental part.
- 4 - Ilva être donné maintenant à titre non limitatif un exemple - 4 - It will be given now without limitation an example
de mise en oeuvre de l'invention.implementation of the invention.
Exemple: 8 - nitro- 1,2 - dihydro - 2 (N-méthyl-pipérazin- Example: 8-nitro-1,2-dihydro-2 (N-methyl-piperazin)
1-yl) méthylène - 6 - (o-chlorophényl) 1 H, 4 H - imidazo rl,2-al -,4ij benzodiazépine - 1- one. 1-yl) methylene-6 - (o-chlorophenyl) 1H, 4H-imidazo, 2-al-, 4H-benzodiazepin-1-one.
Stade A: 2 - carboxv_éthylamino - 7 - nitro 5 - Step A: 2 - carboxymethylamino - 7 - nitro 5 -
Lo -hlúhénl _3 H-_ = 1Xenzodiazépine. Lo-hlthen 3H-1 = 1Xenzodiazepine.
____ _ ____ _ _____ ___ _________ _ _____ _____ ___ _____
Dags 3 litres d'eau déminéralisée, on introduit 1,360 Kg de glycine puis progressivement en fonction des mousses 1,450 Kg de bicarbonate de sodium. On agite 30 minutes à température ambiante, on introduit 15 litres d'éthanol puis Dags 3 liters of demineralized water, 1.360 kg of glycine is introduced then progressively depending on the foam 1,450 kg of sodium bicarbonate. Stirred 30 minutes at room temperature, 15 liters of ethanol are introduced and
en 5 minutes environ 3 Kg de 7 - nitro 1,3, - dihydro -5- in 5 minutes about 3 Kg of 7 - nitro 1,3, - dihydro -5-
(o -, chlorophényl) - 2 H - 1, 4 - benzodiazépine -2 - thione. (o -, chlorophenyl) - 2H - 1,4 - benzodiazepine - 2 - thione.
On porte au reflux pendant 1H30, distille sous pression réduite, ajoute 15 litres d'eau déminéralisée par 2 fois, Refluxed for 1H30, distilled under reduced pressure, added 15 liters of demineralized water twice,
puis 71,5 de chlorure de méthylène et sépare les phases. then 71.5 of methylene chloride and separates the phases.
On réextrait la phase aqueuse par 3 fois 6 litres de chlorure de méthylène puis à l'eau et recueille les solutions aqueuses A la solution aqueuse obtenue on ajoute 18 litres de chlorure The aqueous phase is re-extracted with 3 times 6 liters of methylene chloride and then with water and the aqueous solutions are collected. To the resulting aqueous solution is added 18 liters of chloride.
de méthylène, puis 1,3 litre d'acidechiorhydrique 22 Be. of methylene, then 1.3 liter of hydrochloric acid 22 Be.
On obtient une solution chlorométhylénique de 2 - carboxymé- A chloromethylenic solution of 2-carboxymethylenediamine is obtained.
thyl amino - 7 - nitro 5 - (o-chlorophényl) 3 H - 1,4 thylamino - 7 - nitro 5 - (o - chlorophenyl) 3H - 1,4
benzodiazépine que l'on utilise au stade suivant. benzodiazepine that is used in the next stage.
Stade B: 8 - nitro - 1,2 - dihydro - 6 - (o-chlorophényl) 1 H, 4 Himidazo Cl, 2 - ai E,4J benzodiazépine 1-one A la solution chlorométhylénique de 2 - carboxy méthyl amino 7 - nitro 5 - (ochlorophényl) 3 H - 1,4- benzodiazépine obtei ci-dessus, on ajoute à + 5 C en 2 minutes environ la solutioi de 1,865 kg de dicyclohexyl carbodiimide dans 3 litres de Stage B: 8 - Nitro - 1,2 - dihydro - 6 - (o - chlorophenyl) 1H, 4 Himidazo Cl, 2 - alfa, 4J benzodiazepine 1 - one To the chloromethylenic solution of 2 - carboxy methyl amino 7 - nitro 5 - (ochlorophenyl) 3 H - 1,4-benzodiazepine obtei above, is added to + 5 C in 2 minutes the solution of 1.865 kg of dicyclohexyl carbodiimide in 3 liters of
chlorure de méthylène puis agite pendant 30 minutes. methylene chloride and then stirred for 30 minutes.
On laisse une nuit au repos puis essore. On lave 2 fois par 3 litres de chlorure de méthylène et recueille la solution chlorométhylénique de 8 nitro - 1,2 - dihydro-6 (o - chlorophényl) 1 H, 4 H - imidazo E 1,2 - a _ 1,4] We leave a night at rest then squeeze. The mixture is washed twice with 3 liters of methylene chloride and the chloromethylenic solution of 8-nitro-1,2-dihydro-6 (o-chlorophenyl) 1H, 4H-imidazo E1.2-α1.4] is collected.
benzo- diazépine 1-one que l'on utilise au stade suivant. benzodiazepine 1-one which is used in the next stage.
- 6- 2502621- 6- 2502621
-6 - Stade C: 8 - Nitro - 1,2 - dihydro - 2 -(N-méthyl Stage C: 8 - Nitro - 1,2 - dihydro - 2 - (N - methyl)
pipérazin- 1-yl) méthylène - 6 -(O-chlorophényl) 1 H. 4 H - piperazin-1-yl) methylene - 6 - (O-chlorophenyl) 1H 4 H -
imidazo r1,2- i| [,41 benzodiazépine 1 - one. imidazo r1,2- i | Benzodiazepine 1-one.
A la solution chlorométhylénique de 8 - nitro-1,2 - To the chloromethylenic solution of 8-nitro-1,2 -
dihydro - 6- (o-chlorophényl) 1 H, 4 H - imidazo [1,2-ai [1,4 benzodiazépine - 1 - one obtenue ci-dessus on ajoute en minutes environ et à température ambiante 650 gr. de triethyl - amine puis 2kg,400 d'une solution de diméthylcetal de la N - formyl N - méthyl pipérazine dont la préparation dihydro-6- (o-chlorophenyl) 1H, 4H-imidazo [1,2-a] 1,4-benzodiazepin-1-one obtained above is added in about minutes and at room temperature 650 gr. of triethylamine then 2kg, 400 of a solution of dimethylcetal of N - formyl N - methyl piperazine whose preparation
est donnée ci-après.is given below.
On agite pendant 1 heure 30 minutes, concentre à sec, sous pression réduite et ajoute 6 litres d'éthanol. On distille en maintenant le niveau constant par addition d'éthanol refroidi à 0 /+2 C puis essore. On lave par clairçage avec de l'éthanol et recueille 4kg,260 de produit brut que l'on Stirred for 1 hour 30 minutes, concentrated to dryness under reduced pressure and added 6 liters of ethanol. It is distilled while maintaining the constant level by addition of ethanol cooled to 0 / + 2 C and then wrung. It is washed with ethanol, and collects 4 kg, 260 of crude product which is
purifie par chaud et froid dans l'éthanol. purifies by hot and cold in ethanol.
On recueille finalement 3,362 Kg de 8 - nitro - 1,2 - dihydro 3,362 Kg of 8 - nitro - 1,2 - dihydro is finally collected.
2 - (N - méthyl pipérazin -1 - yl) méthylène - 6- (o-chloro- 2 - (N - methyl piperazin - 1 - yl) methylene - 6- (o-chloro)
phényl) 1 H, 4 H- imidazo F1,2- F1,44 benzodiazépine phenyl) 1H, 4H-imidazo F1,2-F1,44 benzodiazepine
1- one.1- one.
Le produit obtenu est identique à celui décrit à l'exemple 30 The product obtained is identical to that described in Example 30
du brevet français précité.of the aforementioned French patent.
La solution de diméthylcetal de la N-formyl N - méthyl pipé- N-formyl N-methyl pipethyl dimethylketate solution
razine peut être préparée comme suit: Dans 2 kg. de diméthylcetal de diméthylformamide on introduit 3Kg,3 de N - méthyl pipérazine,porte au reflux pendant 15 H. On distille la N - méthyl pipérazine non combinée sous pression réduite, agite pendmt 1 heure sous pression réduite à 115 C puis refroidit à 20 C. On obtient 3,920 Kg d'une razine can be prepared as follows: In 2 kg. of dimethylformamide dimethylcetal 3 kg of N-methyl piperazine are introduced, refluxed for 15 hours. The uncombined N-methyl piperazine is distilled under reduced pressure, stirred for 1 hour under reduced pressure at 115 ° C. and then cooled to 20 ° C. We obtain 3.920 Kg of a
solution brune de diméthylcetal de N-formylN - méthyl - brown solution of N-formylN dimethylcetal - methyl -
pipérazine.piperazine.
250262-1250262-1
Claims (2)
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8106171A FR2502621B1 (en) | 1981-03-27 | 1981-03-27 | |
SE8200271A SE448731B (en) | 1981-03-27 | 1982-01-19 | PROCEDURE FOR PREPARING IMIDAZO / 1,2-A // 1,4 / BENZODIAZEPINES |
SE8200271D SE8200271L (en) | 1981-03-27 | 1982-01-19 | NEW PROCEDURE FOR THE PREPARATION OF IMIDAZOBENZODIAZEPINES AND THEIR SALTS |
ES509284A ES509284A0 (en) | 1981-03-27 | 1982-02-03 | A NEW PROCEDURE FOR THE PREPARATION OF IMIDAZOBENZODIAZEPINAS. |
ZA821141A ZA821141B (en) | 1981-03-27 | 1982-02-22 | Process for preparing imidazobenzodiazepines and their salts |
AU80947/82A AU549222B2 (en) | 1981-03-27 | 1982-02-26 | New process for preparing imidazobenzodiazerines and salts |
MA19621A MA19416A1 (en) | 1981-03-27 | 1982-03-18 | NEW PROCESS FOR THE PREPARATION OF IMIDAZOBENZODIAZEPINES AND THEIR SALTS |
IT48036/82A IT1147917B (en) | 1981-03-27 | 1982-03-19 | PROCEDURE FOR THE PREPARATION OF IMIDAZOBENZODIAZEPINE AND THEIR SALTS |
NL8201208A NL193246C (en) | 1981-03-27 | 1982-03-23 | Process for the preparation of imazobenzodiazepines and their salts. |
JP57045728A JPS57169483A (en) | 1981-03-27 | 1982-03-24 | Manufacture of imidazobenzodiazepines and salts thereof |
MX957582A MX155260A (en) | 1981-03-27 | 1982-03-25 | PROCEDURE FOR THE PREPARATION OF IMIDA-ZODIAZEPINES |
FI821058A FI71152C (en) | 1981-03-27 | 1982-03-25 | NYTT FOERFARANDE FOER FRAMSTAELLNING AV 1,2-DIHYDRO-1H-IMIDAZO / 1,2-A / / 1,4 / BENZODIAZEPIN-1-ON-DERIVAT OCH DERAS SALTER |
GB8208933A GB2095674B (en) | 1981-03-27 | 1982-03-26 | New process for preparing imidazobenzodiazepines as well as their salts |
DK138682A DK153404C (en) | 1981-03-27 | 1982-03-26 | PROCEDURE FOR THE MANUFACTURE OF IMIDAZOBENZODIAZEPINES OR SALTS THEREOF |
PT74669A PT74669B (en) | 1981-03-27 | 1982-03-26 | NOVEL PROCESS FOR THE PREPARATION OF IMIDAZOBENZODIAZEPINES AND THEIR SALTS |
HU82939A HU185092B (en) | 1981-03-27 | 1982-03-26 | New process for preparing imidazo-benzodizephine derivatives and salts thereof |
CA000399537A CA1175823A (en) | 1981-03-27 | 1982-03-26 | Process for preparing imidazobenzodiazepins and their salts |
DE19823211243 DE3211243A1 (en) | 1981-03-27 | 1982-03-26 | NEW METHOD FOR PRODUCING IMIDAZOBENZODIAZEPINES AND THEIR SALTS |
CH1896/82A CH651565A5 (en) | 1981-03-27 | 1982-03-26 | PROCESS FOR THE PREPARATION OF IMIDAZOBENZODIAZEPINES AND THEIR SALTS. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8106171A FR2502621B1 (en) | 1981-03-27 | 1981-03-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2502621A1 true FR2502621A1 (en) | 1982-10-01 |
FR2502621B1 FR2502621B1 (en) | 1983-10-28 |
Family
ID=9256708
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR8106171A Expired FR2502621B1 (en) | 1981-03-27 | 1981-03-27 |
Country Status (17)
Country | Link |
---|---|
JP (1) | JPS57169483A (en) |
AU (1) | AU549222B2 (en) |
CA (1) | CA1175823A (en) |
CH (1) | CH651565A5 (en) |
DE (1) | DE3211243A1 (en) |
DK (1) | DK153404C (en) |
ES (1) | ES509284A0 (en) |
FI (1) | FI71152C (en) |
FR (1) | FR2502621B1 (en) |
GB (1) | GB2095674B (en) |
HU (1) | HU185092B (en) |
IT (1) | IT1147917B (en) |
MA (1) | MA19416A1 (en) |
NL (1) | NL193246C (en) |
PT (1) | PT74669B (en) |
SE (2) | SE8200271L (en) |
ZA (1) | ZA821141B (en) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2300569A1 (en) * | 1975-02-15 | 1976-09-10 | Roussel Uclaf | CNS-active imidazolobenzodiazepines - e.g. 8-chloro-1,2-dihydro-2-(N-methyl-piperazin-1-yl)methylene-6-pheny- l-1H, 4H-imidazo(1,2-a) (1,4)benzodiazepine-1-one |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3872090A (en) * | 1972-07-12 | 1975-03-18 | Boehringer Sohn Ingelheim | 3-(amino-methylene)-5-phenyl-1,4-benzodiazepin-2-ones |
-
1981
- 1981-03-27 FR FR8106171A patent/FR2502621B1/fr not_active Expired
-
1982
- 1982-01-19 SE SE8200271D patent/SE8200271L/en not_active Application Discontinuation
- 1982-01-19 SE SE8200271A patent/SE448731B/en not_active IP Right Cessation
- 1982-02-03 ES ES509284A patent/ES509284A0/en active Granted
- 1982-02-22 ZA ZA821141A patent/ZA821141B/en unknown
- 1982-02-26 AU AU80947/82A patent/AU549222B2/en not_active Expired
- 1982-03-18 MA MA19621A patent/MA19416A1/en unknown
- 1982-03-19 IT IT48036/82A patent/IT1147917B/en active
- 1982-03-23 NL NL8201208A patent/NL193246C/en not_active IP Right Cessation
- 1982-03-24 JP JP57045728A patent/JPS57169483A/en active Pending
- 1982-03-25 FI FI821058A patent/FI71152C/en not_active IP Right Cessation
- 1982-03-26 DE DE19823211243 patent/DE3211243A1/en active Granted
- 1982-03-26 PT PT74669A patent/PT74669B/en unknown
- 1982-03-26 CA CA000399537A patent/CA1175823A/en not_active Expired
- 1982-03-26 CH CH1896/82A patent/CH651565A5/en not_active IP Right Cessation
- 1982-03-26 GB GB8208933A patent/GB2095674B/en not_active Expired
- 1982-03-26 DK DK138682A patent/DK153404C/en not_active IP Right Cessation
- 1982-03-26 HU HU82939A patent/HU185092B/en not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2300569A1 (en) * | 1975-02-15 | 1976-09-10 | Roussel Uclaf | CNS-active imidazolobenzodiazepines - e.g. 8-chloro-1,2-dihydro-2-(N-methyl-piperazin-1-yl)methylene-6-pheny- l-1H, 4H-imidazo(1,2-a) (1,4)benzodiazepine-1-one |
Also Published As
Publication number | Publication date |
---|---|
PT74669B (en) | 1985-01-08 |
DE3211243C2 (en) | 1993-05-19 |
MA19416A1 (en) | 1982-10-01 |
ES8302712A1 (en) | 1983-01-16 |
AU549222B2 (en) | 1986-01-23 |
DK153404B (en) | 1988-07-11 |
IT8248036A0 (en) | 1982-03-19 |
FI71152C (en) | 1986-11-24 |
ES509284A0 (en) | 1983-01-16 |
CH651565A5 (en) | 1985-09-30 |
ZA821141B (en) | 1983-01-26 |
CA1175823A (en) | 1984-10-09 |
DE3211243A1 (en) | 1982-10-07 |
FI821058L (en) | 1982-09-28 |
HU185092B (en) | 1984-11-28 |
GB2095674A (en) | 1982-10-06 |
FR2502621B1 (en) | 1983-10-28 |
NL8201208A (en) | 1982-10-18 |
SE448731B (en) | 1987-03-16 |
DK138682A (en) | 1982-09-28 |
AU8094782A (en) | 1982-09-30 |
FI821058A0 (en) | 1982-03-25 |
SE8200271L (en) | 1982-09-28 |
FI71152B (en) | 1986-08-14 |
NL193246C (en) | 1999-04-02 |
GB2095674B (en) | 1984-10-10 |
DK153404C (en) | 1988-11-21 |
IT1147917B (en) | 1986-11-26 |
PT74669A (en) | 1982-04-01 |
JPS57169483A (en) | 1982-10-19 |
NL193246B (en) | 1998-12-01 |
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