Method for producing 3-amidinophenylalanine derivatives

Details Method for producing 3-amidinophenylalanine derivatives Method for producing 3-amidinophenylalanine derivatives

2007-05-01

2007-05-01

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

active

10506256

ABSTRACT:
The present invention describes a method for the synthesis of enantiomerically pure 3-amidinophenylalanine derivatives, which are used as pharmaceutically effective urokinase inhibitors, by starting from 3-cyanophenylalanine derivatives. The methods of manufacture comprising only one synthesis step lead to new intermediates, namely 3-hydroxyamidino- and 3-amidrazonophenylalanine derivatives. These intermediates or their acetyl derivatives can be reduced into the desired 3-amidinophenylalanine derivatives under gentle conditions (H2or ammonium formiate, Pd/C (approx. 10%), ethanol/water, room temperature, normal pressure or also H2, Pd/C, AcOH or HOI/ethanol, 1–3 bar) in excellent yields and in an enantiomeric excess of up to 99.9%.

REFERENCES:
Sturzebecher et al. Bioorganic & Medicinal Chemistry Letters 9 (1999) 3147-52.
Smith, Organic Synthesis, (1994), 658-664.
Wikipedia, Protecting group, on-line publication.

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