Irbesartan

• IUPAC: 2-butyl- 3-( {4 - [ 2 - (2H -1 ,2,3,4 -tetrazol- 5-yl) phenyl] phenyl} methyl) -1,3- diazaspiro [4.4 ] non- 1 -en- 4-one

C09CA04

Antihypertensive

AT1 antagonist

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Irbesartan is a drug from the group of AT1 antagonist that is used in treatment of hypertension and mild to moderate heart failure when ACE inhibitor therapy is unsuitable used.

Areas of application (indications )

Irbesartan is used for the treatment of the following diseases:

• Essential hypertension
• Renal disease in patients with hypertension and type 2 diabetes mellitus as part of an antihypertensive treatment.

Representation and extraction

The multi-stage synthesis of irbesartan is made ​​from cyclopentanone, wherein in the first step by reaction with sodium cyanide and ammonia is obtained 1- amino-1- cyclopentancarbonitril. Via amide formation with pentanoic acid chloride and subsequent basic cyclization a spiro intermediate compound. Then, biphenyl -2-carbonitrile in the presence of added sodium hydride and dimethylformamide with 4'- (bromomethyl) the Biphenylsubstruktur into the molecule. In the last step of the synthesis of the cyano group is Tetrazolfunktion obtain the target compound by means of sodium azide by the formation.

Properties

The compound occurs in two polymorphic crystal forms. A polymorph melting at 181 ° C with a heat of fusion of 91 J · g -1, polymorph B at 186 ° C and 116 J · g -1. Both forms are monotropic each other. The polymorph B is the thermodynamically stable crystal form. The two polymorphic crystal forms differ in the tautomerism of Tetrazolstruktur. Polymorph A corresponds to the 4H- Tetrazolstruktur, polymorph B of the 2H- Tetrazolstruktur. Polymorph A crystallizes in a hexagonal crystal system, the polymorph B, however. Triclinic crystal system in a