Alfuzosin hydrochloride synthesis

8synthesis methods

Product Name:Alfuzosin hydrochloride
CAS Number:81403-68-1
Molecular formula:C19H28ClN5O4
Molecular Weight:425.91

Alfuzosin HCl is a pharmaceutical drug of the alpha-1 blocker class. As an antagonist of the alpha-1 adrenergic receptor, it works by relaxing the muscles in the prostate and bladder neck, making it easier to urinate. It is thus used to treat benign prostatic hyperplasia (BPH). Alfuzosin is marketed in the United States by Sanofi Aventis under the brand name Uroxatral and elsewhere under the tradename Xat or Xatral, and in Egypt under name of Prostetrol. Alfuzosin was approved by the FDA for treatment of BPH in June 2003.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

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ROUTE 8

ROUTE 9

ROUTE 10

Manoury, Philippe M.; Binet, Jean L.; Dumas, Andre P.; Lefevre-Borg, Francoise; Cavero, Icilio. Synthesis and antihypertensive activity of a series of 4-amino-6,7-dimethoxyquinazoline derivatives. Journal of Medicinal Chemistry. Volume 29. Issue 1. Pages 19-25. 1986.

81403-80-7 Synthesis

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81403-68-1
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Yield:81403-68-1 88%

Reaction Conditions:

with hydrogenchloride in ethanol at 20 - 25;

Steps:

4
Example 4:Preparation of anhydrous Alfuzosin hydrochloride: Alfuzosin base (5g, 0.013mol) is charged to a flask and ethanol (110ml) added. The mixture is refluxed for 15 min. and the solid dissolved. Activated charcoal is added to this solution and the suspension is stirred for lOmin., filtered and washed with 5ml hot ethanol. The filtrate is cooled down to 20-25⁰C and the ethanol saturated by hydrogen chloride gas (1.5ml) is added. Then diethyl ether (25ml) and water (0.09ml) were slowly added to the mixture. The mixture is then stirred at room temperature for 20 hours. The mixture is then cooled down to 0-5⁰C and after stirring for one hour the product is filtered off and washed with 7.5ml of diethyl ether. The crystalline product is dried in a vacuum drier at 12O⁰C for minimum 8 hours. The yield of alfuzosin hydrochloride is 4.85g (88%).

References:

UNICHEM LABORATORIES LIMITED WO2008/84493, 2008, A2 Location in patent:Page/Page column 9-10

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