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US 8,044,215 B2Granted
Methods for the preparation of amphillic nitrogen containing imidazolinium derivative compounds
AssigneeJuvaris BioTherapeutics, Inc.
InventorsCheng-Sein Yu, Lee B. Bussey
Life of this patent
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Abstract
The disclosure provides new methods for preparing nitrogen-containing amphiphiles and their use in the preparation of liposomes and other lipid-containing carriers of pharmaceutical substances, including nucleic acids used in gene therapy.
Claims21
A method for preparing a compound of formula (I):
- comprising the step of heating a compound of formula (II) between about 30° C. to about 60° C. in a trihaloalkyl/alcohol solvent, and in the presence of molecular sieves, to produce the compound of formula (I):
- wherein:
- R and R1 are each independently a C11-C29 straight-chain aliphatic hydrocarbyl group;
- and
- Y is a halogen, acetate, succinate or citrate.
2 more elements
A method for preparing a compound of formula (I):
- comprising the steps of:
- a) protecting the secondary amino groups in the compound of formula (IV) to provide the compound of formula (V):
- b) protecting the primary alcohol groups in the compound of formula (V) to provide the compound of formula (VI):
- c) deprotecting the compound of formula (VI) to provide the compound of formula (II):
- d) heating the compound of formula (II) between about 30° C. to about 60° C. in a trihaloalkyl/alcohol solvent, and in the presence of molecular sieves, to produce the compound of formula (I):
- wherein:
- R and R1 are each independently a C11-C29 straight-chain aliphatic hydrocarbyl group;
- X′ is di-tert-butyldicarbonate ((BOC)2O);
- X is tert-butyloxycarbonyl (BOC);
- Y is a halogen, acetate, succinate or citrate;
- Z in OCOR or OCOR1.
8 more elements
Dependencies are inferred from the claim text.