Process for the preparation of 5-{2-[benzyl-(1-(4-hydroxyphenyl)-1-methylethyl)amino]-1-hydroxyethyl}benzene-1,3-diol hemifumarate
FR3148237B1Active Publication Date: 2025-10-17IND CHEM SRL
View PDF 0 Cites 0 Cited by
Patent Information
- Application Number
- FR2024004346
- Authority / Receiving Office
- FR · FR
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2023-04-26
- Filing Date
- 2024-04-25
- Publication Date
- 2025-10-17
- Estimated Expiration
- 2044-04-25
AI Technical Summary
Technical Problem
Existing methods for synthesizing fenoterol hydrobromide result in an unacceptable ratio of RR,SS to RS,SR isomers, leading to low industrial yield and the need for lengthy purification processes.
Method used
A process involving the preparation of a solution with a protic acid, reduction of the carbonyl function, treatment with a base, and precipitation of a hemifumarate salt, followed by purification to achieve a desired isomer ratio.
Benefits of technology
The process achieves a high yield of the RR,SS isomer, meeting European Pharmacopoeia specifications without requiring extensive purification, such as column chromatography or repeated crystallizations.
✦ Generated by Eureka AI based on patent content.
Abstract
The present invention relates to a process for the industrial-scale preparation of 5-{2-[benzyl-(1-(4-hydroxyphenyl)-1-methylethyl)amino]-1-hydroxyethyl}benzene-1,3-diol hemifumarate, a salt consisting of two molecules of 5-{2-[benzyl-(1-(4-hydroxyphenyl)-1-methylethyl)amino]-1-hydroxyethyl}benzene-1,3-diol and one molecule of fumaric acid, having the following formula:5-{2-[benzyl-(1-(4-hydroxyphenyl)-1-methylethyl)amino]-1-hydroxyethyl}benzene-1,3-diol hemifumarate is a useful intermediate in the synthesis of 5-[(1RS)-2-[(1RS)-2-(4-hydroxyphenyl)-1-methylethyl]-amino-1-hydroxyethyl]benzene-1,3-diol hydrobromide, known in the pharmaceutical field under the common name fenoterol hydrobromide.
Need to check novelty before this filing date? Find Prior Art