Processes for the preparation of (S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine

Patent metadata

Field	Value
Publication number	US-9688623-B2
Application number	US-201715414782-A
Country	US
Kind code	B2
Filing date	Jan 25, 2017
Priority date	Feb 21, 2012
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

Provided herein are new processes for the preparation of aminosulfone intermediates for the synthesis of 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, which is useful for preventing or treating diseases or conditions related to an abnormally high level or activity of TNF-α. Further provided herein are processes for the commercial production of (S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine.

First claim

What is claimed is:

1. A compound of Formula (IV):

or a pharmaceutically acceptable salt, hydrate, solvate, or polymorph thereof, wherein:
R is C 1 -C 6 alkyl;
R 1 is C 1 -C 6 alkyl;
each of R 2 , R 3 , R 4 , R 5 , and R 6 is at each occurrence independently hydrogen, halo, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, —CF 3 , —CN or —NO 2 ; and
Ar is aryl.

2. The compound of claim 1 , wherein the compound of Formula (IV) is racemic.

3. The compound of claim 1 , wherein the compound of Formula (IV) is the (+)- or (−)-enantiomer.

4. The compound of claim 1 , wherein R is —CH 3 ; R 1 is —CH 3 ; R 2 is H; R 3 is H; R 4 is —OCH 3 ; R 5 is —OCH 2 CH 3 ; R 6 is H; and Ar is phenyl.

5. The compound of claim 4 , wherein the compound is the hydrochloride salt.

6. The compound of claim 4 , wherein the compound is the isopropanol solvate hydrochloride salt.

7. The compound of claim 1 , wherein the compound is:

8. The compound of claim 7 , wherein the compound is the hydrochloride salt.

9. The compound of claim 7 , wherein the compound is the isopropanol solvate hydrochloride salt.

Assignees

• Celgene Corp

Inventors

• Venkateswaralu Jasti
• Rajendiran Chinnapillai
• Reddy Nallamaddi Ravikumar
• Connolly Terrence Joseph
• Ruchelman Alexander L
• Eckert Jeffrey
• Frank Anthony Joseph

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• A61P11/00

  Drugs for disorders of the respiratory system · CPC title