FR2696745A1 - Prepn. of derivs. of phenyl-tetrazole - by reacting benzeneboronic acid deriv. with aryl halide in presence of a palladium catalyst - Google Patents
Prepn. of derivs. of phenyl-tetrazole - by reacting benzeneboronic acid deriv. with aryl halide in presence of a palladium catalyst Download PDFInfo
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- FR2696745A1 FR2696745A1 FR9212167A FR9212167A FR2696745A1 FR 2696745 A1 FR2696745 A1 FR 2696745A1 FR 9212167 A FR9212167 A FR 9212167A FR 9212167 A FR9212167 A FR 9212167A FR 2696745 A1 FR2696745 A1 FR 2696745A1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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 un procédé de préparation de dérivés de phényltétrazole répondant à la formule (I) dans laquelle
R1, R2 et R3 représentent chacun indépendamment l'un de l'autre, soit un groupe (C1-C2)alkyle, soit un groupe aryle et
Ar représente soit un groupe aryle éventuellement substitué, soit un groupe naphtyle éventuellement substitué, soit un hétérocycle choisi parmi les groupes pyridinyle, pyrimidinyle, thiényle, imidazolyle, quinoléinyle et imidazopyridinyle éventuellement substitués.R1, R2 and R3 each represent, independently of one another, either a (C1-C2) alkyl group or an aryl group and
Ar represents either an optionally substituted aryl group, or an optionally substituted naphthyl group, or a heterocycle chosen from the pyridinyl, pyrimidinyl, thienyl, imidazolyl, quinolinyl and imidazopyridinyl groups optionally.
Le groupe -CR1R2R3 qui est de préférence le groupe 1,1-dimé thyléthyle, peut être en position 1 ou 2 du cycle tétrazole. The group -CR1R2R3 which is preferably the 1,1-dimethylethyl group, may be in position 1 or 2 of the tetrazole ring.
Le procédé de l'invention permet un couplage direct arylearyle, aryle-naphtyle ou aryle-hétérocycle en présence d'un catalyseur au palladium.The process of the invention allows direct arylearyl, aryl-naphthyl or aryl-heterocycle coupling in the presence of a palladium catalyst.
Le procédé selon l'invention est décrit dans le schéma suivant
On fait réagir un dérivé de l'acide benzèneboronique de formule (II) dans laquelle R1, R2 et R3 sont tels que définis précédemment avec un dérivé de formule (III) dans laquelle Z représente un atome d'halogène choisi parmi les atomes de chlore, d'iode ou de brome; la réaction est réalisée en présence d'une base telle que par exemple, le carbonate de sodium, le carbonate de potassium, le dihydrogènophosphate de potassium ou une amine tertiaire comme la triéthylamine et d'un catalyseur tel le palladiumtétrakis(triphénylphosphine), dans un solvant tel que par exemple, le toluène, le benzène, le xylène, le diméthylformamide ou un éther commme le 1,2-diméthoxyéthane.A benzeneboronic acid derivative of formula (II) in which R1, R2 and R3 are as defined above is reacted with a derivative of formula (III) in which Z represents a halogen atom chosen from chlorine atoms , iodine or bromine; the reaction is carried out in the presence of a base such as for example, sodium carbonate, potassium carbonate, potassium dihydrogen phosphate or a tertiary amine such as triethylamine and a catalyst such as palladiumtetrakis (triphenylphosphine), in a solvent such as, for example, toluene, benzene, xylene, dimethylformamide or an ether such as 1,2-dimethoxyethane.
Les composés de formule (II) sont décrits dans la demande de brevet français 9203114 de la demanderesse et sont préparés à partir du 2-(1,1-diméthyléthyl)-5-phényl-2H-tétrazole que l'on fait réagir avec un alkyllithium dans un solvant aprotique à une température comprise entre - 500C et + 200C.The compounds of formula (II) are described in French patent application 9203114 by the applicant and are prepared from 2- (1,1-dimethylethyl) -5-phenyl-2H-tetrazole which is reacted with a alkyllithium in an aprotic solvent at a temperature between - 500C and + 200C.
On obtient alors un organolithien que l'on fait réagir avec du trialkylborate dans un solvant aprotique pour obtenir un benzèneboronate d'alkyle que l'on soumet à une réaction d'hydrolyse.An organolithian is then obtained which is reacted with trialkylborate in an aprotic solvent to obtain an alkyl benzeneboronate which is subjected to a hydrolysis reaction.
Les composés de formule (II) peuvent également être préparés à partir d'un organomagnésien comme décrit ci-dessous.The compounds of formula (II) can also be prepared from an organomagnesium as described below.
Les composés de formule (III) sont disponibles dans le commerce ou décrits dans la littérature ou peuvent être préparés selon des méthodes qui y sont décrites ou qui sont connues de l'homme du métier.The compounds of formula (III) are commercially available or described in the literature or can be prepared according to methods which are described therein or which are known to those skilled in the art.
Ainsi, la 2-chloro-6-méthylquinoléine est préparée selon la méthode décrite dans Hétérocycles, 28, 1085, (1989).Thus, 2-chloro-6-methylquinoline is prepared according to the method described in Hétérocycles, 28, 1085, (1989).
La 3-bromo-2-(4-éthylphényl)-6-méthylimidazof1,2-a]pyridine est préparée selon la méthode décrite dans J. Org. Chem., 30, 4081, (1965).3-Bromo-2- (4-ethylphenyl) -6-methylimidazof1,2-a] pyridine is prepared according to the method described in J. Org. Chem., 30, 4081, (1965).
Les exemples qui suivent illustrent en détail la préparation des composés selon l'invention.The examples which follow illustrate in detail the preparation of the compounds according to the invention.
Les microanalyses et les spectres IR et RMN confirment la structure des composés obtenus.Microanalyses and IR and NMR spectra confirm the structure of the compounds obtained.
Exemple 1 2-(1 , 1-dimethylethyl)-5-(2-(naphtalèn-1-yl)phenyl]-2H- tétrazole 1.1. acide t2-[2-(1,1-diméthyléthyl)-2H-tétrazol-5-yl]- phenyl Jboronique
Dans un ballon tricol de 100 ml, muni d'un réfrigérant, sous azote, on introduit 0,37 g (15 mmoles) de magnésium en tournures dans 5 ml de tétrahydrofurane anhydre. On ajoute ensuite, goutte à goutte, à la température de reflux, 3,28 g (10 mmoles) de 2-(1,1-diméthyléthyl)-5-(2-iodophényl)-2H- tétrazole dans 20 ml de tétrahydrofurane anhydre. On agite la solution, à 50 OC, pendant 30 minutes et on la refroidit à - 50 OC. On l'ajoute à une solution de 5,4 ml (20 mmoles) de triéthylborate dans 15 ml de tétrahydrofurane anhydre.On laisse le mélange une nuit, sous agitation, à la température ambiante puis on le verse sur 50 ml d'une solution d'acide chlorhydrique à 10 %. On extrait le mélange par 100 ml d'acétate d'éthyle, on lave la phase organique avec 30 ml d'eau et on la sèche sur du sulfate de magnésium. Après filtration et évaporation, on recueille un résidu que l'on purifie par chromatographie sur colonne de gel de silice.Example 1 2- (1, 1-dimethylethyl) -5- (2- (naphthalen-1-yl) phenyl] -2H- tetrazole 1.1. T2- [2- (1,1-dimethylethyl) -2H-tetrazol- acid 5-yl] - phenyl Jboronique
0.37 g (15 mmol) of magnesium in turnings are introduced into 5 ml of anhydrous tetrahydrofuran into a 100 ml three-necked flask equipped with a condenser under nitrogen. 3.28 g (10 mmol) of 2- (1,1-dimethylethyl) -5- (2-iodophenyl) -2H- tetrazole in 20 ml of anhydrous tetrahydrofuran are then added dropwise at reflux temperature . The solution is stirred at 50 OC for 30 minutes and cooled to -50 OC. It is added to a solution of 5.4 ml (20 mmol) of triethylborate in 15 ml of anhydrous tetrahydrofuran. The mixture is left overnight, with stirring, at room temperature and then poured into 50 ml of a solution. 10% hydrochloric acid. The mixture is extracted with 100 ml of ethyl acetate, the organic phase is washed with 30 ml of water and dried over magnesium sulfate. After filtration and evaporation, a residue is collected which is purified by chromatography on a column of silica gel.
On obtient 1,62 g de produit.1.62 g of product are obtained.
Point de fusion = 115-118 OC Rendement = 66 % 1.2. 2-(1,1-dimethylethyl)-5-[2-(naphtalèn-1-yl)phenyl]-2H- tétrazole
Dans un ballon tricol de 100 ml, muni d'un réfrigérant, on introduit successivement 2 g (8,13 mmoles) de l'acide obtenu précédemment en 1.1, 1,6 g (7,75 mmoles) de l-bromo-naphta- lène, 0,447 g de palladium tétrakis(triphénylphosphine) et 8,2 ml d'une solution 2 M de carbonate de sodium dans 30 ml de toluène. On porte le milieu réactionnel à la température de reflux pendant 4 heures, puis on verse le mélange dans 20 ml d'une solution saturée en chlorure d'ammonium. On extrait par de l'acétate d'éthyle et on recueille la phase organique. On la lave successivement par 20 ml d'eau et par 20 ml d'une solution saturée en chlorure de sodium.On la sèche sur du sulfate de magnésium et on évapore sous vide. On purifie le résidu obtenu, par chromatographie sur colonne de gel de silice.Melting point = 115-118 OC Yield = 66% 1.2. 2- (1,1-dimethylethyl) -5- [2- (naphthalen-1-yl) phenyl] -2H- tetrazole
2 g (8.13 mmol) of the acid previously obtained in 1.1, 1.6 g (7.75 mmol) of l-bromo-naphta are successively introduced into a 100 ml three-necked flask equipped with a condenser. - lene, 0.447 g of tetrakis palladium (triphenylphosphine) and 8.2 ml of a 2 M solution of sodium carbonate in 30 ml of toluene. The reaction medium is brought to reflux temperature for 4 hours, then the mixture is poured into 20 ml of a saturated solution of ammonium chloride. Extraction is carried out with ethyl acetate and the organic phase is collected. It is washed successively with 20 ml of water and with 20 ml of a saturated solution of sodium chloride. It is dried over magnesium sulphate and evaporated under vacuum. The residue obtained is purified by chromatography on a column of silica gel.
On obtient 1,45 g de produit.1.45 g of product are obtained.
Point de fusion = 83-85 OC Rendement = 57 %
Exemple 2 3-[2-[2-(1,1-diméthyléthyl)-2H-tétrazol-5-yl]phényl]pyridine
Dans un ballon tricol muni d'un réfrigérant et d'un thermomètre, on introduit successivement 1,71 g (6,96 mmoles) du composé préparé selon la méthode décrite dans l'exemple 1.1, 1 g (6.32 mmoles) de 3-bromopyridine, 0,37 g de palladium tétrakis(triphényphosphine), 6,3 ml d'une solution 2 M de carbonate de sodium dans 25 ml de toluène. On porte le mélange au reflux pendant 6 heures. On verse la solution dans 20 ml d'une solution saturée de chlorure d'ammonium. On extrait avec de l'acétate d'éthyle. On lave la phase organique avec 20 ml d'eau puis avec 20 ml d'une solution saturée en chlorure de sodium. On la sèche sur du sulfate de magnésium et on évapore sous vide. On purifie le résidu par chromatographie sur colonne de gel de silice.Melting point = 83-85 OC Yield = 57%
Example 2 3- [2- [2- (1,1-dimethylethyl) -2H-tetrazol-5-yl] phenyl] pyridine
1.71 g (6.96 mmol) of the compound prepared according to the method described in Example 1.1, 1 g (6.32 mmol) of 3- are successively introduced into a three-necked flask fitted with a condenser and a thermometer. bromopyridine, 0.37 g of palladium tetrakis (triphenyphosphine), 6.3 ml of a 2 M solution of sodium carbonate in 25 ml of toluene. The mixture is brought to reflux for 6 hours. The solution is poured into 20 ml of a saturated ammonium chloride solution. Extraction is carried out with ethyl acetate. The organic phase is washed with 20 ml of water and then with 20 ml of a saturated sodium chloride solution. It is dried over magnesium sulphate and evaporated under vacuum. The residue is purified by chromatography on a column of silica gel.
On obtient 1,03 g de produit.1.03 g of product are obtained.
Point de fusion = 204 C Rendement = 58 %
ExemPle 3 4-chloro-2- (2- (2- (1 , 1 -dimethylethyl) -2H-tetrazol-5-yl] phényl]pyrimidine
Dans un ballon tricol muni d'un réfrigérant, on introduit successivement 2 g (8,13 mmoles) du composé préparé selon la méthode décrite dans l'exemple 1.1, 1,15 g (7,74 mmoles) de 2,4-dichloropyrimidine, 8,2 ml d'une solution 2 M de carbonate de sodium et 0,447 g de palladium tétrakis(triphénylphosphine) dans 30 ml de toluène. On porte le mélange réactionnel au reflux pendant 6 heures. On verse la solution dans 20 ml d'une solution saturée en chlorure d'ammonium. On extrait avec de l'acétate d'éthyle. On lave la phase orga nique avec 20 ml d'eau puis avec 20 ml d'une solution saturée en chlorure de sodium. On la sèche sur du sulfate de magnésium et on évapore sous vide.On purifie le résidu par chromatographie sur colonne de gel de silice.Melting point = 204 C Yield = 58%
Example 3 4-chloro-2- (2- (2- (1, 1 -dimethylethyl) -2H-tetrazol-5-yl] phenyl] pyrimidine
2 g (8.13 mmol) of the compound prepared according to the method described in Example 1.1, 1.15 g (7.74 mmol) of 2,4-dichloropyrimidine are successively introduced into a three-necked flask fitted with a condenser. , 8.2 ml of a 2 M solution of sodium carbonate and 0.447 g of tetrakis palladium (triphenylphosphine) in 30 ml of toluene. The reaction mixture is brought to reflux for 6 hours. The solution is poured into 20 ml of a saturated ammonium chloride solution. Extraction is carried out with ethyl acetate. The organic phase is washed with 20 ml of water and then with 20 ml of a saturated sodium chloride solution. It is dried over magnesium sulphate and evaporated under vacuum. The residue is purified by chromatography on a column of silica gel.
On obtient 1,52 g de produit.1.52 g of product are obtained.
Point de fusion = 115-117 OC Rendement = 64 %
Exemple 4 2-[2-[2-(1,1-diméthyléthyl)-2H-tétrazol-5-yl]phényl] quinoléine
Dans un ballon tricol muni d'un réfrigérant, on introduit successivement 2 g (8,13 mmoles) du composé préparé selon la méthode décrite dans l'exemple 1.1, 1,33 g (8,13 mmoles) de 2-chloroquinoléine, 8,2 ml d'une solution 2 M de carbonate de sodium, 0,470 g de palladium tétrakis(triphénylphosphine) dans 25 ml de toluène. On porte le mélange réactionnel au reflux pendant 6 heures. Après retour à la température ambiante, on décante la phase aqueuse et on l'extrait avec 100 ml d'acétate d'éthyle. On réunit les phases organiques et on les lave successivement avec 40 ml d'eau puis 50 ml d'une solution saturée en chlorure de sodium . On les sèche sur du sulfate de magnésium.Après évaporation du solvant, on obtient 2,15 g de produit sous forme d'une huile que l'on solidifie par chlorhydratation dans l'éther.Melting point = 115-117 OC Yield = 64%
Example 4 2- [2- [2- (1,1-dimethylethyl) -2H-tetrazol-5-yl] phenyl] quinoline
2 g (8.13 mmol) of the compound prepared according to the method described in Example 1.1, 1.33 g (8.13 mmol) of 2-chloroquinoline, 8 are successively introduced into a three-necked flask equipped with a condenser , 2 ml of a 2 M solution of sodium carbonate, 0.470 g of tetrakis palladium (triphenylphosphine) in 25 ml of toluene. The reaction mixture is brought to reflux for 6 hours. After returning to room temperature, the aqueous phase is decanted and extracted with 100 ml of ethyl acetate. The organic phases are combined and washed successively with 40 ml of water and then 50 ml of a saturated sodium chloride solution. They are dried over magnesium sulphate. After evaporation of the solvent, 2.15 g of product are obtained in the form of an oil which is solidified by hydrochlorination in ether.
Point de fusion = 68 OC Rendement = 80 %
ExemPle 5 2-[2-[2-(1,1-dimethyléthyl)-2H-tetrazol-5-yl]phenyl]6-methyl- quinoléine
Dans un ballon tricol muni d'un réfrigérant, on introduit successivement 1,52 g (6,17 mmoles) du composé préparé selon la méthode décrite dans l'exemple 1.1, 1 g (5,62 mmoles) de 2-chloro-6-méthyl-quinoléine, 6 ml d'une solution 2 M de carbonate de sodium, 0,33 g de palladium tétrakis(triphénylphosphine) dans 25 ml de toluène. On porte le mélange réactionnel à reflux pendant 6 heures. Après retour à la température ambiante, on décante la phase aqueuse et on l'extrait avec 100 ml d'acétate d'éthyle. On réunit les phases organiques, on les lave successivement avec 40 ml d'eau puis 60 ml d'une solution de chlorure de sodium saturée et on les sèche sur du sulfate de magnésium.On évapore les solvants puis on purifie le résidu obtenu, par chromatographie sur gel de silice.Melting point = 68 OC Yield = 80%
Example 5 2- [2- [2- (1,1-dimethylethyl) -2H-tetrazol-5-yl] phenyl] 6-methyl- quinoline
1.52 g (6.17 mmol) of the compound prepared according to the method described in Example 1.1 are successively introduced into a three-necked flask fitted with a condenser. 1 g (5.62 mmol) of 2-chloro-6 -methyl quinoline, 6 ml of a 2 M solution of sodium carbonate, 0.33 g of tetrakis palladium (triphenylphosphine) in 25 ml of toluene. The reaction mixture is brought to reflux for 6 hours. After returning to room temperature, the aqueous phase is decanted and extracted with 100 ml of ethyl acetate. The organic phases are combined, washed successively with 40 ml of water and then 60 ml of a saturated sodium chloride solution and dried over magnesium sulfate. The solvents are evaporated off and the residue obtained is purified by chromatography on silica gel.
On obtient 1,58 g de produit.1.58 g of product are obtained.
Point de fusion = 104 OC Rendement = 82 %
Exemple 6 3-t2-t2-(l,l-diméthyléthyl)-2H-tétrazol-5-yl]phényl]-2-(4- éthylphényl)-6-méthylimidazotl,2-a]pyridine
Dans un ballon tricol muni d'un réfrigérant et d'un thermomètre, on introduit successivement 1,22 g (4,96 mmoles) du composé préparé selon la méthode décrite dans l'exemple 1.1, 1,5 g (4.73 mmoles) de 3-bromo-2-(4-éthylphényl)-6-méthyl imidazo[l,2-a)pyridine, 0,273 g de palladium tétrakis(triphénylphosphine) et 5 ml d'une solution 2 M de carbonate de sodium dans 20 ml de toluène. On porte le mélange réactionnel à reflux pendant 4 heures. On verse la solution dans 20 ml d'une solution saturée en chlorure d'ammonium. On extrait avec de l'acétate d'éthyle. On lave la phase organique avec 20 ml d'eau puis avec 20 ml d'une solution saturée en chlorure de sodium. On la sèche sur du sulfate de magnésium et on évapore sous vide. On purifie le résidu par chromatographie sur colonne de gel de silice.Melting point = 104 OC Yield = 82%
Example 6 3-t2-t2- (1,1-dimethylethyl) -2H-tetrazol-5-yl] phenyl] -2- (4-ethylphenyl) -6-methylimidazotl, 2-a] pyridine
1.22 g (4.96 mmol) of the compound prepared according to the method described in Example 1.1, 1.5 g (4.73 mmol) are successively introduced into a three-necked flask fitted with a condenser and a thermometer. 3-bromo-2- (4-ethylphenyl) -6-methyl imidazo [1,2-a) pyridine, 0.273 g of palladium tetrakis (triphenylphosphine) and 5 ml of a 2 M solution of sodium carbonate in 20 ml of toluene. The reaction mixture is brought to reflux for 4 hours. The solution is poured into 20 ml of a saturated ammonium chloride solution. Extraction is carried out with ethyl acetate. The organic phase is washed with 20 ml of water and then with 20 ml of a saturated sodium chloride solution. It is dried over magnesium sulphate and evaporated under vacuum. The residue is purified by chromatography on a column of silica gel.
On obtient 1,4 g de produit.1.4 g of product are obtained.
Point de fusion = 172-174 OC Rendement = 67 %
Le procédé selon l'invention permet d'obtenir des composés de formule (I) de haute pureté avec un bon rendement.Melting point = 172-174 OC Yield = 67%
The process according to the invention makes it possible to obtain compounds of formula (I) of high purity with a good yield.
Il permet le couplage des halogénures aromatiques ou hétérocycliques comportant des fonctions organiques usuelles telles que par exemple les alcools, les éthers, les amines, les aldéhydes, les cétones, les acides, les esters, les nitriles, les amides, et les dérivés nitrés ou soufrés.It allows the coupling of aromatic or heterocyclic halides comprising usual organic functions such as for example alcohols, ethers, amines, aldehydes, ketones, acids, esters, nitriles, amides, and nitrates or sulfur.
D'autre part ce procédé évite l'emploi d'azotures explosifs et contribue à la protection de l'environnement (recyclage du palladium). On the other hand, this process avoids the use of explosive azides and contributes to environmental protection (recycling of palladium).
Claims (5)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9212167A FR2696745B1 (en) | 1992-10-12 | 1992-10-12 | Process for the preparation of phenyltetrazole derivatives. |
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| Application Number | Priority Date | Filing Date | Title |
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| FR9212167A FR2696745B1 (en) | 1992-10-12 | 1992-10-12 | Process for the preparation of phenyltetrazole derivatives. |
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| FR2696745A1 true FR2696745A1 (en) | 1994-04-15 |
| FR2696745B1 FR2696745B1 (en) | 1995-05-12 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0623611A1 (en) * | 1993-05-06 | 1994-11-09 | Bayer Ag | Pyridinylmethyl substituted pyridines and pyridones as Angiotensine II antagonists |
| EP0623610A1 (en) * | 1993-05-06 | 1994-11-09 | Bayer Ag | Substituted pyridines and 2-oxo-1,2-dihydropyridines as Angiotensine II antagonists |
| US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
| US6579876B2 (en) | 1998-07-02 | 2003-06-17 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| ES2300175A1 (en) * | 2006-02-14 | 2008-06-01 | Inke, S.A. | Method for obtaining intermediate, particularly candesartan used in preparation of active pharmaceutical compound, particularly candesartan cilexetil for treatment of hypertension or heart failure, involves forming diphenyl bond |
| WO2009086123A1 (en) * | 2007-12-21 | 2009-07-09 | Wyeth | Imidazo [1,2-a] pyridine compounds |
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| EP0455423A2 (en) * | 1990-05-02 | 1991-11-06 | Merck & Co. Inc. | Ortho-lithiation process for the synthesis of 2-substituted 1-(tetrazol-5-yl) benzenes |
| US5130439A (en) * | 1991-11-18 | 1992-07-14 | Lo Young S | Tetrazolylphenylboronic acid intermediates for the synthesis of AII receptor antagonists |
| US5149699A (en) * | 1991-10-24 | 1992-09-22 | American Home Products Corporation | Substituted pyridopyrimidines useful as antgiotensin II antagonists |
| EP0504888A1 (en) * | 1991-03-21 | 1992-09-23 | G.D. Searle & Co. | 5-Arylheteroarylalkyl-1,3,5-trisubstituted-1,2,4-triazole compounds for treatment of circulatory disorders |
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1992
- 1992-10-12 FR FR9212167A patent/FR2696745B1/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4620025A (en) * | 1984-08-01 | 1986-10-28 | Merck & Co., Inc. | Process for the preparation of biphenyl intermediates |
| EP0455423A2 (en) * | 1990-05-02 | 1991-11-06 | Merck & Co. Inc. | Ortho-lithiation process for the synthesis of 2-substituted 1-(tetrazol-5-yl) benzenes |
| EP0504888A1 (en) * | 1991-03-21 | 1992-09-23 | G.D. Searle & Co. | 5-Arylheteroarylalkyl-1,3,5-trisubstituted-1,2,4-triazole compounds for treatment of circulatory disorders |
| US5149699A (en) * | 1991-10-24 | 1992-09-22 | American Home Products Corporation | Substituted pyridopyrimidines useful as antgiotensin II antagonists |
| US5130439A (en) * | 1991-11-18 | 1992-07-14 | Lo Young S | Tetrazolylphenylboronic acid intermediates for the synthesis of AII receptor antagonists |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0623611A1 (en) * | 1993-05-06 | 1994-11-09 | Bayer Ag | Pyridinylmethyl substituted pyridines and pyridones as Angiotensine II antagonists |
| EP0623610A1 (en) * | 1993-05-06 | 1994-11-09 | Bayer Ag | Substituted pyridines and 2-oxo-1,2-dihydropyridines as Angiotensine II antagonists |
| US5414003A (en) * | 1993-05-06 | 1995-05-09 | Bayer Aktiengesellschaft | Pyridinylmethyl-substituted pyridines and pyridones |
| US5492923A (en) * | 1993-05-06 | 1996-02-20 | Bayer Aktiengesellschaft | Substituted pyridines and 2-oxo-1,2-dihydropyridines |
| US5712296A (en) * | 1993-05-06 | 1998-01-27 | Bayer Aktiengesellschaft | Substituted pyridines and 2-oxo-1,2-dihydropyridines |
| US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
| US6579876B2 (en) | 1998-07-02 | 2003-06-17 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| ES2300175A1 (en) * | 2006-02-14 | 2008-06-01 | Inke, S.A. | Method for obtaining intermediate, particularly candesartan used in preparation of active pharmaceutical compound, particularly candesartan cilexetil for treatment of hypertension or heart failure, involves forming diphenyl bond |
| WO2009086123A1 (en) * | 2007-12-21 | 2009-07-09 | Wyeth | Imidazo [1,2-a] pyridine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2696745B1 (en) | 1995-05-12 |
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