Process for preparation of irbesartan

Abstract

A process for the preparation of Irbesartan of formula (I) using the step of, reacting biphenyl derivative of formula (VIa) wherein R represents a group selected from —CONH 2 or compound of formula wherein X represents H or C 1-4 alkyl, preferably methyl; or any other such group which can be converted to cyano group, with 1-veleramido cyclopentane carboxylic acid of formula (V) in the presence of an acid in an organic solvent to give biphenyl derivative of formula (VIIa) wherein R has the same meaning as mentioned hereinabove.

1 . A process for the preparation of Irbesartan of formula (I) comprising step of, 
     
       
         
         
             
             
         
       
       reacting biphenyl derivative of formula (VIa) 
     
     
       
         
         
             
             
         
       
       wherein R represents a group selected from —CONH 2  or compound of formula 
     
     
       
         
         
             
             
         
       
       wherein X represents H or C 1-4  alkyl, preferably methyl; 
       or any other such group which can be converted to cyano group, 
       with 1-veleramido cyclopentane carboxylic acid of formula (V) 
     
     
       
         
         
             
             
         
       
       in the presence of an acid in an organic solvent to give biphenyl derivative of formula (VIIa) 
     
     
       
         
         
             
             
         
       
       wherein R has the same meaning as mentioned hereinabove. 
     
   
   
       2 . The process as claimed in  claim 1 , wherein said acid is selected from the group consisting of organic and inorganic acids or mixture thereof. 
   
   
       3 . The process as claimed in  claim 2 , wherein the organic acid is selected from the group comprising methane sulfonic acid and p-toluene sulfonic acid. 
   
   
       4 . The process as claimed in  claim 2 , wherein the inorganic acid is sulfuric acid. 
   
   
       5 . The process as claimed in  claim 1 , wherein said organic solvent is selected from the group consisting of C 1-8  aromatic hydrocarbons or mixture thereof. 
   
   
       6 . The process as claimed in  claim 5  wherein C 1-8  aromatic hydrocarbons is toluene. 
   
   
       7 . A process for the preparation of Irbesartan of formula (I) comprising steps of: 
     
       
         
         
             
             
         
       
       (i) reacting biphenyl derivative of formula (Via) 
     
     
       
         
         
             
             
         
       
       
         wherein R represents a group selected from —CONH 2  or compound of formula 
       
     
     
       
         
         
             
             
         
       
       
         wherein X represents H or C 1-4  alkyl, preferably methyl; 
         or any other such group which can be converted to cyano group, 
         with 1-veleramido cyclopentane carboxylic acid of formula (V), 
       
     
     
       
         
         
             
             
         
       
       
         in the presence of an acid in an organic solvent to give biphenyl derivative of formula (VIIa); 
       
     
     
       
         
         
             
             
         
       
       
         wherein R has the same meaning as mentioned hereinabove; 
       
       (ii) converting the compound of formula (VIIa) to compound of formula (VII); 
     
     
       
         
         
             
             
         
       
       (iii) converting the compound of formula (VII) obtained in step (ii) to Irbesartan of formula (I) by reacting the compound of the formula (VII) with tributyl tin azide in o-xylene to give Irbesartan of formula (I). 
     
   
   
       8 . The process as claimed in  claim 7 , wherein said acid is selected from the group consisting of organic and inorganic acids or mixture thereof. 
   
   
       9 . The process as claimed in  claim 8 , wherein the organic acid is selected from the group comprising methane sulfonic acid and p-toluene sulfonic acid. 
   
   
       10 . The process as claimed in  claim 8 , wherein the inorganic acid is sulfuric acid. 
   
   
       11 . The process as claimed in  claim 7 , wherein said organic solvent is selected from the group consisting of C 1-8  aromatic hydrocarbons or mixture thereof. 
   
   
       12 . The process as claimed in  claim 11  wherein C 1-8  aromatic hydrocarbons is toluene. 
   
   
       13 . A process for the preparation of Irbesartan of formula (I) comprising step of, 
     
       
         
         
             
             
         
       
       reacting biphenyl derivative of formula (Vib) 
     
     
       
         
         
             
             
         
       
       wherein A represents protected tetrazolyl group 
       with 1-veleramido cyclopentane carboxylic acid of formula (V) 
     
     
       
         
         
             
             
         
       
       in the presence of an acid in an organic solvent to give biphenyl derivative of formula (VIIb) 
     
     
       
         
         
             
             
         
       
       wherein A has the same meaning as mentioned hereinabove. 
     
   
   
       14 . The process as claimed in  claim 13 , wherein said acid is selected from the group consisting of organic and inorganic acids or mixture thereof. 
   
   
       15 . The process as claimed in  claim 14 , wherein the organic acid is selected from the group comprising methane sulfonic acid and p-toluene sulfonic acid. 
   
   
       16 . The process as claimed in  claim 14 , wherein the inorganic acid is sulfuric acid. 
   
   
       17 . The process as claimed in  claim 13 , wherein said organic solvent is selected from the group consisting of C 1-8  aromatic hydrocarbons or mixture thereof. 
   
   
       18 . The process as claimed in  claim 17  wherein C 1-8  aromatic hydrocarbons is toluene. 
   
   
       19 . A process for the preparation of Irbesartan of formula (I) comprising steps of: 
     
       
         
         
             
             
         
       
       (i) reacting biphenyl derivative of formula (Vib) 
     
     
       
         
         
             
             
         
       
       
         wherein A represents protected tetrazolyl group 
         with 1-veleramido cyclopentane carboxylic acid of formula (V) 
       
     
     
       
         
         
             
             
         
       
       
         in the presence of an acid in an organic solvent to give biphenyl derivative of formula (VIIb). 
       
     
     
       
         
         
             
             
         
       
       
         wherein A has the same meaning as mentioned hereinabove; 
       
       (ii) deprotecting the protected tetrazolyl group present in the compound of formula (VIIb) to Irbesartan of formula (I) by hydrolysis or hydrogenolysis. 
     
   
   
       20 . The process as claimed in  claim 19 , wherein said acid is selected from the group consisting of organic and inorganic acids or mixture thereof. 
   
   
       21 . The process as claimed in  claim 20 , wherein the organic acid is selected from the group comprising methane sulfonic acid and p-toluene sulfonic acid. 
   
   
       22 . The process as claimed in  claim 20 , wherein the inorganic acid is sulfuric acid. 
   
   
       23 . The process as claimed in  claim 19 , wherein said organic solvent is selected from the group consisting of C 1-8  aromatic hydrocarbons or mixture thereof. 
   
   
       24 . The process as claimed in  claim 23  wherein C 1-8  aromatic hydrocarbons is toluene. 
   
   
       25 . A process for the preparation of 1-veleramidocyclopentane carboxylic acid of formula (V) comprising, 
     
       
         
         
             
             
         
       
       reacting Aminocyclopentane carboxylic acid hydrochloride salt of formula (IV) 
     
     
       
         
         
             
             
         
       
       with valeroyl chloride in the presence of a base and a phase transfer catalyst (PTC) in a suitable solvent and water to give 1-veleramido cyclopentane carboxylic acid of formula (V). 
     
   
   
       26 . The process as claimed in  claim 25 , wherein the phase transfer catalyst is selected from the group comprising quarternery ammonium compound, phosphonium compound and cyclic polyethers. 
   
   
       27 . The process as claimed in  claim 26 , wherein the phase transfer catalyst is selected from the group tetrabutyl ammonium bromide (TBAB), tetrabutyl ammonium hydrogensulfate, benzalkonium chloride, cetyl trimethyl ammonium chloride or mixture thereof. 
   
   
       28 . The process as claimed in  claim 25 , wherein the suitable solvent is selected from the group comprising non polar water immiscible solvent. 
   
   
       29 . The process as claimed in  claim 28 , wherein the suitable solvent is selected from toluene, xylene, benzene, dichloromethane, cyclohexane, hexane, heptane and the mixture thereof. 
   
   
       30 . The process as claimed in  claim 25 , wherein the base is selected from alkali metal hydroxide, alkaline earth metal carbonate or bicarbonate. 
   
   
       31 . The process as claimed in  claim 30 , wherein the base is selected from NaOH or KOH, LiOH, Na 2 CO 3 , K 2 CO 3 , KHCO 3 , NaHCO 3 , CaCO 3  or mixture thereof. 
   
   
       32 . A process of preparation of Irbesartan comprising the steps of:
 (i) reacting Aminocyclopentane carboxylic acid hydrochloride salt of formula (IV)   
     
       
         
         
             
             
         
       
       
         with valeroyl chloride in the presence of a base and a phase transfer catalyst (PTC) in a suitable solvent and water to give 1-veleramido cyclopentane carboxylic acid of formula (V) 
       
     
     
       
         
         
             
             
         
       
       (ii) reacting 4′ aminomethyl-2-cyano biphenyl of formula (VI) with 1-veleramido cyclopentane carboxylic acid of formula (V) 
     
     
       
         
         
             
             
         
       
       
         in the presence of an acid in an organic solvent to give 1-(2′cyanobiphenyl-4-yl-methylaminocarbonyl)-1-pentanoylamino cyclopentane of formula (VII). 
       
     
     
       
         
         
             
             
         
       
     
   
   
       33 . The process as claimed in  claim 32 , wherein the phase transfer catalyst is selected from the group comprising quarternery ammonium compound, phosphonium compound and cyclic polyethers. 
   
   
       34 . The process as claimed in  claim 33 , wherein the phase transfer catalyst is selected from the group tetrabutyl ammonium bromide (TBAB), tetrabutyl ammonium hydrogensulfate, benzalkonium chloride, cetyl trimethyl ammonium chloride or mixture thereof. 
   
   
       35 . The process as claimed in  claim 32 , wherein the suitable solvent is selected from the group comprising non polar water immiscible solvent. 
   
   
       36 . The process as claimed in  claim 35 , wherein the suitable solvent is selected from toluene, xylene, benzene, dichloromethane, cyclohexane, hexane, heptane and the mixture thereof. 
   
   
       37 . The process as claimed in  claim 32 , wherein the base is selected from alkali metal hydroxide, alkaline earth metal carbonate or bicarbonate. 
   
   
       38 . The process as claimed in  claim 37 , wherein the base is selected from NaOH or KOH, LiOH, Na 2 CO 3 , K 2 CO 3 , KHCO 3 , NaHCO 3 , CaCO 3  or mixture thereof. 
   
   
       39 . The process as claimed in  claim 32 , wherein said acid is selected from the group consisting of organic and inorganic acids or mixture thereof. 
   
   
       40 . The process as claimed in  claim 39 , wherein the organic acid is selected from the group comprising methane sulfonic acid and p-toluene sulfonic acid. 
   
   
       41 . The process as claimed in  claim 39 , wherein the inorganic acid is sulfuric acid. 
   
   
       42 . The process as claimed in  claim 32 , wherein said organic solvent is selected from the group consisting of C 1-8  aromatic hydrocarbons or mixture thereof. 
   
   
       43 . The process as claimed in  claim 42  wherein C 1-8  aromatic hydrocarbons is toluene.