Novel synthesis of salcaprozic acid by amide formation
OwnerNiels Krogsgaard-Larsen, Michael Raunkjaer +3inventors
InventorsNiels Krogsgaard-Larsen, Michael Raunkjaer, Christian Walter Risinger, Rolf Hejle Taaning, Vitaly Komnatnyy
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Abstract
The present invention relates to a chemical process for the synthesis of the compound 8-[(2-hydroxybenzoyl)amino]octanoic acid or a derivative thereof useful in the process of making sodium 8-[(2-hydroxybenzoyl)amino]octanoate (SNAC), a delivery agent used in solid pharmaceutical compositions. The invention provides an efficient synthesis using less hazardous chemicals and/or a reproducible process that is easier to handle on production scale.
Claims19
A method for producing a compound of formula (I),
- wherein R1 is selected from hydrogen, C1-C6-alkyl, phenyl, benzyl, Mg2+, Ca2+, Li+, Na+ and K+,
- comprising a step of reacting a compound of formula (II),
- wherein R2 is selected from hydrogen, C1-C6-alkyl, phenyl, benzyl, Mg2+, Ca2+, Li+, Na+ and K+,
- and a compound of formula (III),
- wherein X is selected from O-alkyl, O-phenyl, O-benzyl and N-hydroxysuccimide (NHS).
A method for producing a compound of formula (I-a),
- comprising the steps of
- a) reacting the compound of formula (II-a),
- and the compound of formula (III-a),
- obtaining the compound of formula (I-b),
- as an intermediate, and
- b) obtaining the compound of formula (I-a) by precipitation.
Dependencies are inferred from the claim text.