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US 12,077,487 B2Granted
Methods of manufacturing benzoquinoline compounds
AssigneeAuspex Pharmaceuticals, Inc.
InventorChengzhi Zhang
Life of this patent
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Abstract
The present invention relates to new methods of manufacturing benzoquinoline inhibitors of vesicular monoamine transporter 2 (VMAT2), and intermediates thereof.
Claims21
A process of preparing (cis)-d6-tetrabenazine having a diastereomeric purity of at least 99%, comprising:
- a) reacting d6-6,7-dimethoxy-3,4-dihydroisoquinoline, or a salt thereof,
- d6-6,7-dimethoxy-3,4-dihydroisoquinoline
- with a salt of 2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium:
- 2-acetyl-N,N,N,4-tetramethyl-1-pentanaminium salt
- wherein X is halogen, alkyl sulfate, alkyl sulfonate, halosulfonate, perhaloalkyl sulfonate, aryl sulfonate, alkylaryl sulfonate, dialkyloxonium, alkylphosphate, or alkyl carbonate;
- and an optional base;
- in the presence of water and methanol;
- for a period of time and at a temperature sufficient to produce crude (cis)-d6-tetrabenazine;
- and
- b) recrystallizing the crude (cis)-d6-tetrabenazine from ethanol to produce the (cis)-d6-tetrabenazine having a diastereomeric purity of at least 99%.
7 more elements
Dependencies are inferred from the claim text.