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US 9,434,680 B2Granted
Methods for synthesizing and purifying aminoalkyl tetracycline compounds
AssigneeParatek Pharmaceuticals, Inc.
InventorsSean Johnston, Tadeusz Warchol
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Abstract
Methods for the synthesis and purification of 9-amino alkyl tetracycline compounds are described.
Claims44
A method for the synthesis of a 9-aminomethyl minocycline compound of the following structural formula:
- the method comprising:
- a) contacting minocycline with a N-hydroxymethyl pthalimide compound (Pht) in the presence of a water scavenger and an acid under a reaction temperature of 20-35° C. to form a first 9-aminomethyl minocycline intermediate of the following structural formula:
- b) reacting said first 9-aminomethyl minocycline intermediate formed in step a) with methylamine in the presence of ether and alkyl alcohol to form a second 9-aminomethyl minocycline intermediate of the following structural formula:
- and
- c) treating said second 9-aminomethyl minocycline intermediate formed in step b) through hydrogenation to form said 9-aminomethyl minocycline compound.
2 more elements
A method for the synthesis of a 9-aminomethyl minocycline compound of the following structural formula:
- the method comprising:
- a) contacting minocycline with a N-hydroxymethyl pthalimide compound (Pht) in the presence of an acid under a reaction temperature of 20-35° C. to form a first 9-aminomethyl minocycline intermediate of the following structural formula:
- b) reacting said first 9-aminomethyl minocycline intermediate formed in step a) with methylamine in the presence of ether and alkyl alcohol to form a second 9-aminomethyl minocycline intermediate of the following structural formula:
- and
- c) treating said second 9-aminomethyl minocycline intermediate formed in step b) through hydrogenation to form said 9-aminomethyl minocycline compound.
2 more elements
Dependencies are inferred from the claim text.