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US 2015/0148533 A1Published application
New Synthetic Route For The Preparation Of Beta-aminobutyryl Substituted 5,6,7,8-tetrahydro[1,4]diazolo[4,3-alpha]Pyrazin-7-yl Compounds
AssigneeLek Pharmaceuticals D.D.
InventorsStefan Starcevic, Peter Mrak, Gregor Kopitar
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Abstract
The present invention relates to a process for preparing □-aminobutyryl substituted 5,6,7,8-tetrahydro[1,4]diazolo[4,3-α]pyrazin-7-yl compounds.
Claims15
A process for the preparation of a compound of formula IV,
- wherein Ar denotes unsubstituted or substituted C6-C12-aryl, Q denotes N, CH or a carbon substituted with unsubstituted or substituted C1-C6-alkyl, C6-C12-aryl or C7-C12-alkylaryl, and R denotes H or unsubstituted or substituted C1-C6-alkyl, C6-C12-aryl or C7-C12-alkylaryl,
- comprising a step of coupling a compound of formula II,
- wherein Ar is defined as above,
- with a compound of formula III or a salt thereof,
- wherein R and Q are defined as above,
- in the presence of a catalyst in an organic solvent.
3 more elements
A process for preparing a substantially enantiopure compound of formula IIa″,
- wherein chiral center is in R-configuration,
- in which process a racemic or enantioenriched compound of formula IIa
- is subjected to kinetic resolution by means of a hydrolytic enzyme in the presence of an organic solvent, wherein the S-enantiomer of compound of formula IIa′ is converted to a compound of formula Ia′
- while the R-enantiomer of compound of formula IIa″ remains substantially unreacted.
1 more element
A process for preparing compound of formula I
- in racemic form, the process comprising the steps of:
- i) oxidation of a compound of formula I in enantioenriched or enantiopure form to its C—N double bonded intermediates by means of an oxidizing agent, and
- ii) reduction of the C—N double bonded intermediates obtained in step i) by means of a reducing agent,
- in order to obtain compound of formula I in racemic form.
1 more element
Dependencies are inferred from the claim text.