Process for preparing 3-oxo-4-aza-5-alpha-androstane-17-carboxylic acid

• US 20060046994A1
• Filed: 08/24/2005
• Published: 03/02/2006
• Est. Priority Date: 08/25/2004
• Status: Abandoned Application

• Current Assignee: Dr. Reddy's Lab., Inc. (Dr. Reddy's Laboratories Ltd.), Dr. Reddy's Laboratories Ltd.
• Original Assignee: Dr. Reddy's Lab., Inc. (Dr. Reddy's Laboratories Ltd.), Dr. Reddy's Laboratories Ltd.
• Inventors: Khunt, Mayur Devjibhai, Venkataraman, Sundaram, Sripathi, Somaiah, Bojja, Ramchandra Reddy, Godipati, Srinivasulu, Keshava, Naveenkumar Reddy
• Application Number:
  US11/210,528
• Publication Number:
  US 20060046994A1
• Time in Patent Office: Days
• US Class Current: 514/294
• CPC Class Codes: C07D 221/18 Ring systems of four or more rings
• CPC Class Codes: C07J 73/005 by nitrogen as hetero atom

Abstract

A process for preparing the compound 3-oxo-4-aza-5α-androstane-17β-carboxylic acid having Formula (I): which is an intermediate in the preparation of 4-azasteroid drug compounds like finesteride, dutasteride, etc.

Claims

1. A process for preparing a compound having Formula (I):

comprising;

(a) reacting a compound having Formula (II);

where R is a branched or unbranched C₁-C₅ alkyl group, with an oxidizing agent to form a compound having Formula (III);

(b) reacting the compound having Formula (III) with a cyclizing agent to form a compound having Formula (IV);

where R is as defined above; and

(c) reacting the compound having Formula (IV) with a reducing agent to form a compound having Formula (V);

where R is as defined above; and

(d) hydrolyzing the compound having Formula (V) to form the compound having Formula (I).

2. The process of claim 1, wherein the oxidizing agent comprises a permanganate salt, a periodate salt, or a mixture thereof.

3. The process of claim 1, wherein oxidizing agent is added in multiple portions.

4. The process of claim 1, wherein the cyclizing agent comprises ammonium acetate in the presence of acetic acid.

5. The process of claim 1, wherein the reducing agent comprises formic acid.

6. The process of claim 1, wherein hydrolyzing occurs under basic conditions.

7. A process for preparing a compound having formula (I):

comprising;

(a) reacting a compound having Formula (II);

where R is a branched or unbranched C₁-C₅ alkyl group, with an oxidizing agent comprising potassium permanganate and sodium metaperiodate to form a compound having Formula (III);

(b) reacting the compound having Formula (III) with a cyclizing agent comprising ammonium acetate and acetic acid to form a compound having Formula (IV);

where R is as defined above; and

(c) reacting the compound having Formula (IV) with a reducing agent comprising formic acid to form a compound having Formula (V);

where R is as defined above; and

(d) hydrolyzing the compound having Formula (V) with a base to form the compound having Formula (I).