Ligands for estrogen related receptors and methods for synthesis of said ligands
AssigneeCity of Hope
InventorsBarry Forman, Donna Yu
Life of this patent
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Abstract
Estrogen-Related Receptor (ERR) modulating compounds and methods for synthesis of said compounds are described.
Claims23
A method for synthesis of 4-hydroxy-benzoic acid (4-diethylamino-benzylidene)-hydrazide comprising:
- refluxing 4-diethylaminobenzaldehyde with 4-methoxybenzoic acid hydrazide in absolute ethanol wherein said refluxing is conducted in the presence of a catalytic amount of acetic acid.
A method for synthesis of 4-hydroxy-benzoic acid (4-diethylamino-benzylidene)-hydrazide comprising:
- reacting 4-methoxy-benzoic acid (4-diethylamino-benzylidene)-hydrazide with α-bromo-p-xylene to form 4-methoxy-benzoic acid N′-(4-diethylamino-benzylidene)-N-4-(methyl-benzyl)-hydrazide;
- and
- performing simultaneous demethylation and deprotection of the N-benzyl group of the product of step one by ether cleavage with boron tribromide.
A method for synthesis of 4-hydroxy-benzoic acid (4-diethylamino-benzylidene)-hydrazide comprising:
- providing a first solution of 4-methoxy-benzoic acid N′-(4-diethylamino-benzylidene)-N-4-(methyl-benzyl)-hydrazide and a solvent;
- adding a second solution of boron tribromide and a second solvent;
- mixing the first and second solutions;
- and
- treating the mixed first and second solutions with 1:1 methanol:dichromethane.
A method for synthesis of 4-hydroxy-benzoic acid (4-diethylamino-benzylidene)-hydrazide comprising:
- providing a solution of 4-hydroxy-benzoic acid hydrazide, 4-diethylaminoaldehyde and a solvent;
- adding acetic acid;
- and
- refluxing the solution.
A compound prepared by the process comprising the steps of:
- refluxing 4-diethylaminobenzaldehyde with 4-methoxybenzoic acid hydrazide in absolute ethanol wherein said refluxing is conducted in the presence of a catalytic amount of acetic acid.
A compound prepared by the process comprising the steps of:
- reacting 4-methoxy-benzoic acid (4-diethylamino-benzylidene)-hydrazide with α-bromo-p-xylene to form 4-methoxy-benzoic acid N′-(4-diethylamino-benzylidene)-N-4-(methyl-benzyl)-hydrazide;
- and
- performing simultaneous demethylation and deprotection of the N-benzyl group of the product of step one by ether cleavage with boron tribromide.
A compound prepared by the process comprising the steps of:
- providing a first solution of 4-methoxy-benzoic acid N′-(4-diethylamino-benzylidene)-N-4-(methyl-benzyl)-hydrazide and a solvent;
- adding a second solution of boron tribromide and a second solvent;
- mixing the first and second solutions;
- and
- treating the mixed first and second solutions with 1:1 methanol:dichromethane.
A compound prepared by the process comprising the steps of:
- providing a solution of 4-hydroxy-benzoic acid hydrazide, 4-diethylaminoaldehyde and a solvent;
- adding acetic acid;
- and
- refluxing the solution.
A method for the synthesis of an Estrogen-Related Receptor (ERR) ligand comprising
A method for the synthesis of an Estrogen-Related Receptor (ERR) ligand comprising
A method for the synthesis of an Estrogen-Related Receptor (ERR) ligand comprising
A method for the synthesis of an Estrogen-Related Receptor (ERR) ligand comprising
A method for the synthesis of an Estrogen-Related Receptor (ERR) ligand comprising:
A method for the synthesis of an Estrogen-Related Receptor (ERR) ligand comprising:
A compound that modulates Estrogen-Related Receptor (ERR).
A method for modulating Estrogen-Related Receptor (ERR) in a subject by providing an Estrogen-Related Receptor (ERR) ligand to a subject.
Dependencies are inferred from the claim text.