Process for the manufacturing of betamimetics

• US 8,420,809 B2
• Filed: 02/07/2011
• Issued: 04/16/2013
• Est. Priority Date: 08/15/2005
• Status: Active Grant

• Current Assignee: Boehringer Ingelheim International GmbH (C.H. Boehringer Sohn AG & Co. KG)
• Original Assignee: Boehringer Ingelheim International GmbH (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: Krueger, Thomas, Ries, Uwe, Rall, Werner, Duran, Adil, Soyka, Rainer, Leuter, Zeno A., Schnaubelt, Juergen
• Primary Examiner(s): MCDOWELL, BRIAN E
• Application Number:
  US13/021,946
• Publication Number:
  US 20110124859A1
• Time in Patent Office: 799 Days
• Field of Search: 544/105
• US Class Current: 544/105
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07C 201/08 by substitution of hydrogen atoms by nitro groups
• CPC Class Codes: C07C 205/45 the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
• CPC Class Codes: C07C 221/00 Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
• CPC Class Codes: C07C 225/22 having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07C 233/13 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
• CPC Class Codes: C07C 233/18 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 45/71 being hydroxy groups
• CPC Class Codes: C07C 49/84 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07D 265/36 condensed with one six-membered ring
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The present invention relates to a process for preparing betamimetics of formula 1,

• • wherein
  • n denotes 1 or 2;
  • R¹ denotes hydrogen, halogen, C_1-4-alkyl or O—C_1-4-alkyl;
  • R² denotes hydrogen, halogen, C_1-4-alkyl or O—C_1-4-alkyl;
  • R³ denotes hydrogen, C_1-4-alkyl, OH, halogen, O—C_1-4-alkyl, O—C_1-4-alkylene-COOH, O—C_1-4-alkylene-COO—C_1-4-alkyl.

Claims

1. A process for preparing a compound of formula 1,

2. A process according to claim 1, said process further comprising reacting a compound of formula 3a,

3. A process according to claim 1, said process further comprising reacting a compound of formula 2b with a strong base in an organic solvent,

4. A process according to claim 3, said process further comprising reacting a compound of formula 3b with acetonitrile in the presence of an acid in an organic solvent,

5. A process according to claim 4, said process further comprising reacting in an organic solvent a compound of formula 4b with methylmagnesium bromide or methylmagnesium chloride,