FR2606411A1 - Imidazopyridineacetamides, their preparation and their application in therapeutics - Google Patents
Imidazopyridineacetamides, their preparation and their application in therapeutics Download PDFInfo
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- FR2606411A1 FR2606411A1 FR8615534A FR8615534A FR2606411A1 FR 2606411 A1 FR2606411 A1 FR 2606411A1 FR 8615534 A FR8615534 A FR 8615534A FR 8615534 A FR8615534 A FR 8615534A FR 2606411 A1 FR2606411 A1 FR 2606411A1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
Description
La présente invention a pour objet des imidazopyridine-acétamides, leur préparation et leur application en thérapeutique.The present invention relates to imidazopyridine acetamides, their preparation and their therapeutic application.
Les composés de l'invention répondent à la formule (I)
dans laquelle
Y et X représentent chacun indépendamment l'un de l'autre un atome de chlore ou le radical méthyle, et
R représente un atome d'hydrogene, un radical (C13)alkyle ou le radical oxo-2 propyle.The compounds of the invention correspond to formula (I)
in which
Y and X are each independently of one another a chlorine atom or the methyl radical, and
R represents a hydrogen atom, a (C13) alkyl radical or the oxo-2 propyl radical.
Les sels d'addition que forment les composés avec les acides pharmaceutiquement acceptables font partie de l'invention.The addition salts formed by the compounds with pharmaceutically acceptable acids form part of the invention.
Les composés de l'invention peuvent être préparés par oxydation des alcools secondaires correspondants qui sont décrits dans le brevet français 80.22537 (2 492 382).The compounds of the invention may be prepared by oxidation of the corresponding secondary alcohols which are described in French patent 80.22537 (2 492 382).
Les exemples suivants illustrent l'invention.The following examples illustrate the invention.
ExemPle 1. Chloro-6 (chloro-4 phényl)-2 N-propyl N-(oxo-2 propyl)imidazo[l,2-a]pyridine-3-acétamide et son chlorhydrate.EXAMPLE 1. 6-Chloro-4- (4-chlorophenyl) -N-propyl N- (2-oxo-propyl) imidazo [1,2-a] pyridine-3-acetamide and its hydrochloride.
1. On met en suspension 30 g (0,093 mole) d'acide (chloro-4 phényl) -2 chloro-6 imidazo[l,2-a]pyridine-3-acétique dans 500 ml de tétrahydrofuranne (THF). On ajoute, tout en agitant, sous argon, 20 g de carbonyldiimidazole. On tiédit à 600C pendant 2 h 30 mn. On laisse revenir à la température ambiante puis on ajoute 22 g (0,19 mole) de N-propyl N (hydroxy-2 propyl)amine distillée dans 25 ml de tétrahydrofu ranne. On chauffe le mélange à 600C pendant une heure puis on ajoute de l'eau et on évapore le THF sous vide.On verse dans de l'eau, on extrait quatre fois au chloroforme, on lave une fois à l'eau, on sèche sur sulfate de sodium puis on évapore à sec pour obtenir le N-propyl N-(hydroxy-2 propyl) chloro-6 (chloro-4 phényl)-2 imidazol,2-a]pyridine-3-acétamide. Le composé est purifié par chromatographie.1. 30 g (0.093 mole) of 2-chloro-4-phenyl-6-chloroimidazo [1,2-a] pyridine-3-acetic acid are suspended in 500 ml of tetrahydrofuran (THF). 20 g of carbonyldiimidazole are added under stirring under argon. It is heated at 600C for 2 hours 30 minutes. The mixture is allowed to return to ambient temperature and then 22 g (0.19 mol) of N-propyl N (2-hydroxypropyl) amine distilled in 25 ml of tetrahydrofuran are added. The mixture is heated at 600 ° C. for one hour, then water is added and the THF is evaporated under vacuum. It is poured into water, extracted four times with chloroform, washed once with water and dried. over sodium sulphate and then evaporated to dryness to obtain N-propyl N- (2-hydroxy-propyl) -6-chloro-4- (4-chlorophenyl) imidazol, 2-a] pyridine-3-acetamide. The compound is purified by chromatography.
2. Dans un ballon, on introduit, tout en agitant, 1,2 g du composé précédent, 100 ml de chlorure de méthylène, 1 g d'acétate de sodium et 1,2 g de chlorochromate de pyridinium.2. 1.2 g of the above compound, 100 ml of methylene chloride, 1 g of sodium acetate and 1.2 g of pyridinium chlorochromate are introduced into a flask with stirring.
On agite le mélange à la température ambiante pendant 2 heures, puis a 450 pendant 1 heure. On verse le mélange dans de l'eau, on extrait 3 fois au chlorure de méthylène, on lave 1 fois à l'eau, on sèche sur sulfate de sodium, on filtre et on évapore à sec. On obtient le produit après chromatographie.The mixture is stirred at room temperature for 2 hours and then at 450 for 1 hour. The mixture is poured into water, extracted 3 times with methylene chloride, washed once with water, dried over sodium sulfate, filtered and evaporated to dryness. The product is obtained after chromatography.
On le transforme en chlorhydrate en le solubilisant dans de l'éthanol et en ajoutant de l'éther chlorhydrique puis de l'éther. Le chlorhydrate cristallise. On le filtre et on le sèche à 50"C. It is converted into hydrochloride by solubilizing it in ethanol and adding hydrochloric ether and then ether. The hydrochloride crystallizes. It is filtered and dried at 50 ° C.
F = 230-2320C.F = 230-2320C.
Exemple 2. N,N-bis(oxo-2 propyl) chloro-6 (chloro-4 phényl)-2 imidazo[1,2-a]pyridine-3-acétamide.Example 2. N, N-bis (2-oxo-propyl) -6-chloro-4- (4-chlorophenyl) imidazo [1,2-a] pyridine-3-acetamide.
1. Dans un ballon tricol, tout en agitant et sous argon, on introduit, 10 g d'acide (chloro-4 phényl)-2 chloro-6 imida zo[l,2-a]pyridine-3-acétique dans 200 ml de tétrahydrofuranne et 6,2 g de carbonyldiimidazole. On tiédit le mélange à 60OC pendant 3 heures, on le laisse revenir à la température ambiante.1. In a three-necked flask, while stirring and under argon, 10 g of 2-chloro-4-phenyl-6-chloroimidazo [1,2-a] pyridine-3-acetic acid are introduced into 200 ml. of tetrahydrofuran and 6.2 g of carbonyldiimidazole. The mixture is heated at 60 ° C for 3 hours, allowed to warm to room temperature.
On ajoute 6,2 g de N,N-(hydroxy-2 propyl)amine et on chauffe le mélange à 600C pendant 1 h.6.2 g of N, N- (2-hydroxypropyl) amine are added and the mixture is heated at 600 ° C. for 1 hour.
On évapore le tétrahydrofuranne, on verse dans de l'eau, on extrait 4 fois au chloroforme, on lave 1 fois à l'eau, on sèche sur sulfate de sodium, on filtre et on évapore à sec.The tetrahydrofuran is evaporated, poured into water, extracted 4 times with chloroform, washed once with water, dried over sodium sulfate, filtered and evaporated to dryness.
On purifie le composé obtenu qui est le N,N-di(hydroxy-2 propyl) chloro-6 (chloro-4 phényl) -2 imidazo[1,2-a]pyridine- 3-acétamide.The resulting compound, N, N-di (2-hydroxypropyl) -6-chloro-4- (4-chlorophenyl) imidazo [1,2-a] pyridine-3-acetamide, is purified.
2. On solubilise 2,4 g de N,N-di(hydroxy-2 propyl) chloro-6 (chloro-4 phényl) -2 imidazo[l,2-a]pyridine-3-acétamide dans 200 ml de chlorure de méthylène. On ajoute 1,5 g d'acétate de sodium et 2,4 g de chlorochromate de pyridinium.2. 2.4 g of N, N-di (2-hydroxy-propyl) -6-chloro-1- (4-chlorophenyl) imidazo [1,2-a] pyridine-3-acetamide are solubilized in 200 ml of sodium chloride. methylene. 1.5 g of sodium acetate and 2.4 g of pyridinium chlorochromate are added.
On agite le mélange à la température ambiante pendant 3 heures. On ajoute de l'eau, on extrait 3 fois au chlorure de méthylène, on lave une fois à l'eau, on sèche sur sulfate de sodium, on filtre et on évapore à sec. On obtient le produit que l'on purifie par chromatographie.The mixture is stirred at room temperature for 3 hours. Water is added, extracted 3 times with methylene chloride, washed once with water, dried over sodium sulfate, filtered and evaporated to dryness. The product is obtained which is purified by chromatography.
F = 194-1950C.Mp 194-1950 ° C.
Exemple 3. Chloro-6 (chloro-4 phényl)-2 N-(oxo-2 propyl) imidazo[1,2-a]pyridine-3-acétamide.Example 3. 6-Chloro-4- (4-chlorophenyl) -N- (oxo-2-propyl) imidazo [1,2-a] pyridine-3-acetamide.
1. Dans un ballon de 100 ml, à l'abri de l'humidité de l'air, on introduit 3,21 g (10 mM) d'acide (chloro-4 phényl)-2 chloro-6 imidazof1,2-a3pyridine-3-acétique en supension dans 35 ml de tétrahydrofuranne sec. On y ajoute 1,95 g (12 mM) de carbonyldiimidazole. La suspension est agitée une heure à la température ambiante puis chauffée à50CC pendant une heure.1. In a 100-ml flask, protected from the humidity of the air, 3.21 g (10 mM) of 4-chloro-4-phenyl-6-chloroimidazol 3-pyridine-3-acetic acid supension in 35 ml of dry tetrahydrofuran. 1.95 g (12 mM) of carbonyldiimidazole are added. The suspension is stirred for one hour at room temperature and then heated at 50 ° C. for one hour.
Le mélange est refroidi à 00C puis on ajoute 3 g (40 mM) d'amino-2 propanol-1 fraichement redistillé. Le mélange est agité pendant 15 minutes à la température ambiante. En fin de réaction, le THF est évaporé sous pression réduite. Le résidu solide est repris par 50 ml d'une solution de bicarbonate de sodium à 10 % puis agité vigoureusement. L'amide est extrait au chloroforme (4 x 100 ml). Les phases chloroformiques sont rassemblées, lavées à l'eau jusqu'a neutralité, séchées sur sulfate de sodium et filtrées. Le filtrat est évaporé à sec.The mixture is cooled to 0 ° C. and then 3 g (40 mM) of 2-amino-1-propanol freshly redistilled is added. The mixture is stirred for 15 minutes at room temperature. At the end of the reaction, the THF is evaporated under reduced pressure. The solid residue is taken up in 50 ml of a 10% sodium bicarbonate solution and then stirred vigorously. The amide is extracted with chloroform (4 x 100 ml). The chloroform phases are combined, washed with water until neutral, dried over sodium sulphate and filtered. The filtrate is evaporated to dryness.
Le produit brut est purifié par chromatographie liquide haute pression.The crude product is purified by high pressure liquid chromatography.
On obtient le N-(hydroxy-2 propyl) chloro-6 (chloro-4 phényl) -2 imidazo[l,2-a]pyridine-3-acétamide. N- (2-Hydroxypropyl) -6-chloro-4- (4-chlorophenyl) imidazo [1,2-a] pyridine-3-acetamide is obtained.
F = 210-2120C. Mp 210-2120C.
2. On introduit 16,3 g du composé précédent dans 400 ml de dichlorométhane. On ajoute 10,5 g d'acétate de sodium et 16,3 g de chlorochromate de pyridinium.2. Introduce 16.3 g of the above compound in 400 ml of dichloromethane. 10.5 g of sodium acetate and 16.3 g of pyridinium chlorochromate are added.
On agite le mélange à la température ambiante pendant 4 heures. On verse dans de l'eau, on extrait 4 fois au chloroforme, on lave 1 fois à l'eau, on sèche sur sulfate de sodium, on filtre et on évapore à sec.The mixture is stirred at room temperature for 4 hours. It is poured into water, extracted 4 times with chloroform, washed once with water, dried over sodium sulfate, filtered and evaporated to dryness.
On évapore 2 fois avec du toluène.It is evaporated twice with toluene.
On purifie le composé brut obtenu par chromatographie.The crude compound obtained is purified by chromatography.
F = 184-1850C.Mp 184-1850 ° C.
Les composés préparés à titre d'exemples sont représentés dans le tableau suivant. The compounds prepared as examples are shown in the following table.
Tableau
<tb> Composé <SEP> Y <SEP> X <SEP> R <SEP> F( C) <SEP> sel
<tb> <SEP> 1 <SEP> Cl <SEP> Cl <SEP> C3H7 <SEP> 230-232 <SEP> (HC1)
<tb> <SEP> 2 <SEP> Cl <SEP> Cl <SEP> CH2COCH3 <SEP> 194-195
<tb> <SEP> 3 <SEP> Cl <SEP> Cl <SEP> H <SEP> 184-185 <SEP> - <SEP>
<tb> <SEP> 4 <SEP> CH3 <SEP> Cl <SEP> H <SEP> 240-241 <SEP> (HCl) <SEP>
<tb> <SEP> CH3 <SEP> CH3 <SEP> H <SEP> 257-258 <SEP> (HC1)
<tb>
Les composés de l'invention ont été soumis aux essais pharmacologiques suivants.<tb> Compound <SEP> Y <SEP> X <SEP> R <SEP> F (C) <SEP> salt
<tb><SEP> 1 <SEP> Cl <SEP> Cl <SEP> C3H7 <SEP> 230-232 <SEP> (HC1)
<tb><SEP> 2 <SEP> Cl <SEP> Cl <SEP> CH2COCH3 <SEP> 194-195
<tb><SEP> 3 <SEP> Cl <SEP> Cl <SEP> H <SEP> 184-185 <SEP> - <SEP>
<tb><SEP> 4 <SEP> CH3 <SEP> Cl <SEP> H <SEP> 240-241 <SEP> (HCl) <SEP>
<tb><SEP> CH3 <SEP> CH3 <SEP> H <SEP> 257-258 <SEP> (HC1)
<Tb>
The compounds of the invention have been subjected to the following pharmacological tests.
L'activité sédative ou hypnotique a été déterminée en observant l'action des composés sur l'ECoG du rat curarisé (Depoortere H., Rev. E.E.G. Neurophysiol., (1980) 10, 3, 207214). Chez le rat curarisé, les produits à étudier sont injectés par voie intrapéritonéale ou orale aux doses croissantes de 1 à 30 mg/kg. Ils induisent des tracés de sommeil aux doses égales ou supérieures à 0,3 mg/kg i.p.Sedative or hypnotic activity was determined by observing the action of the compounds on the ECoG of the curarized rat (Depoortere H., Rev.E.E.G. Neurophysiol., (1980) 10, 3, 207214). In curarized rats, the products to be studied are injected intraperitoneally or orally at increasing doses of 1 to 30 mg / kg. They induce sleep patterns at doses equal to or greater than 0.3 mg / kg i.p.
L'activité anticonvulsivante des composés a été déterminée selon le test de l'inhibition des convulsions cloniques induites par le pentétrazol chez la souris selon la méthode de Worms et coll (J. Pharmacol. Exp. Ther., 220 : 660-671).The anticonvulsant activity of the compounds was determined according to the test for inhibition of pentetrazole-induced clonic convulsions in mice according to the method of Worms et al (J. Pharmacol Exp, Ther., 220: 660-671).
Chez des souris mâles (20-22 g) CDî Charles River, les convulsions cloniques sont induites par injection i.v. de 35 mg/kg de pentetrazol, 30 mn après l'injection i.p. du produit à tester.In male mice (20-22 g) CD1 Charles River, clonic convulsions are induced by i.v. injection of 35 mg / kg pentetrazol, 30 min after i.p. of the product to be tested.
La DA 50 est la dose qui protège 50 % des animaux des convulsions cloniques provoquées par le pentétrazol. La DA 50 des composés de l'invention va de 0,1 à 10 mg/kg.DA 50 is the dose that protects 50% of animals from clonic convulsions caused by pentetrazol. The DA 50 of the compounds of the invention ranges from 0.1 to 10 mg / kg.
Les résultats des essais pharmacologiques montrent que les composés de l'invention sont actifs dans le domaine du système nerveux central et possèdent des propriétés anxiolytiques, inductrices de sommeil, hypnotiques et anticonvulsivantes ; les composés de l'invention sont utiles pour le traitement des états d'anxiétés, des troubles du sommeil et autres affections neurologiques et psychiatriques.The results of the pharmacological tests show that the compounds of the invention are active in the field of the central nervous system and possess anxiolytic, sleep-inducing, hypnotic and anticonvulsant properties; the compounds of the invention are useful for the treatment of anxiety states, sleep disorders and other neurological and psychiatric conditions.
Les composés de l'invention peuvent être présentés sous toute forme appropriée pour l'administration par voie orale, ou parentérale, par exemple sous forme de comprimés, de dragées, de gélules, de solutions buvables ou injectables etc.. avec tout excipient approprié.The compounds of the invention may be presented in any form suitable for administration orally, or parenterally, for example in the form of tablets, dragees, capsules, oral or injectable solutions, etc. with any suitable excipient.
La posologie quotidienne peut aller de 0,5 à 2000 mg. The daily dosage can range from 0.5 to 2000 mg.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8615534A FR2606411B1 (en) | 1986-11-07 | 1986-11-07 | IMIDAZOPYRIDINE-ACETAMIDES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8615534A FR2606411B1 (en) | 1986-11-07 | 1986-11-07 | IMIDAZOPYRIDINE-ACETAMIDES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2606411A1 true FR2606411A1 (en) | 1988-05-13 |
| FR2606411B1 FR2606411B1 (en) | 1989-04-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8615534A Expired FR2606411B1 (en) | 1986-11-07 | 1986-11-07 | IMIDAZOPYRIDINE-ACETAMIDES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
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| Country | Link |
|---|---|
| FR (1) | FR2606411B1 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1076089A (en) * | 1965-11-09 | 1967-07-19 | Selvi & C Lab Bioterapico | New derivatives of imidazo [1,2-a]-pyridine and a process for the manufacture thereof |
| EP0050563A1 (en) * | 1980-10-22 | 1982-04-28 | Synthelabo | Imidazo(1,2-a)pyridine derivatives, process for their preparation and their therapeutical use |
-
1986
- 1986-11-07 FR FR8615534A patent/FR2606411B1/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1076089A (en) * | 1965-11-09 | 1967-07-19 | Selvi & C Lab Bioterapico | New derivatives of imidazo [1,2-a]-pyridine and a process for the manufacture thereof |
| EP0050563A1 (en) * | 1980-10-22 | 1982-04-28 | Synthelabo | Imidazo(1,2-a)pyridine derivatives, process for their preparation and their therapeutical use |
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| Publication number | Publication date |
|---|---|
| FR2606411B1 (en) | 1989-04-07 |
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