Process for the preparation of chiral 8-(3-aminopiperidin-1-yl)-xanthines

• US 9,751,855 B2
• Filed: 01/25/2017
• Issued: 09/05/2017
• Est. Priority Date: 11/05/2004
• 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: Pfrengle, Waldemar, Pachur, Thorsten, Nicola, Thomas, Duran, Adil
• Primary Examiner(s): SAEED, KAMAL A
• Application Number:
  US15/414,694
• Publication Number:
  US 20170129872A1
• Time in Patent Office: 223 Days
• Field of Search: None
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/08 for glucose homeostasis pancreatic hormones A61P5/48
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 37/06 Immunosuppressants, e.g. drugs for graft rejection
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07B 2200/07 Optical isomers
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 473/04 two oxygen atoms
• CPC Class Codes: C07D 473/06 with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3

Abstract

The invention relates to an improved process for preparing enantiomerically pure 8-(3-aminopiperidin-1-yl)-xanthines.

Claims

1. A process for preparing (R)-3-(phthalimido)piperidine, comprising:

reacting rac-3-aminopiperidine with phthalic anhydride; and

precipitating (R)-3-(phthalimido)piperidine by adding D-tartaric acid.

2. A process for preparing (S)-3-(phthalimido)piperidine, comprising:

reacting rac-3-aminopiperidine with phthalic anhydride;

precipitating (S)-3-(phthalimido)piperidine by adding L-tartaric acid.

3. A process for preparing (R)-3-(phthalimido)piperidine and (S)-3-(phthalimido)piperidine, comprising:

reacting rac-3-aminopiperidine with phthalic anhydride; and

precipitating (R)-3-(phthalimido)piperidine by adding D-tartaric acid; and

precipitating (S)-3-(phthalimido)piperidine by adding L-tartaric acid.