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US 7,420,000 B2Granted
Amino phosphonate and amino bis-phosphonate derivatives
AssigneeUniversity of Southern California
InventorNicos A. Petasis
Life of this patent
Estimating the term…
Abstract
Aminophosphonate and amino bisphosphonate compounds and methods for their preparation are provided. Also provided are pharmaceutical and agricultural compositions containing the compounds. The compounds and compositions are useful in methods for treatment of various diseases, including, inflammation, autoimmune disease, cardiovascular disease, bacterial infection, viral disease, abnormal cell proliferation, bone resorption disease, osteoporosis, or parasitic disease and in various agricultural methods, including, methods of eradicating weeds.
Claims66
A compound of general formula:
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R3 is hydrogen, alkyl, alkenyl, aryl, phosphonic acid, phosphonate or phosphonamido;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, or aryl;
- R6 is hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl, aryl, pyridyl, alkenyl, alkynyl, allenyl, formyl, acyl, aminoacyl, carboxy or alkoxyacyl;
- Ra and Rb are independently hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation,
- wherein at least:
- R3 is aryl;
- or R4 is furyl, thienyl, pyrrolyl, benzofuryl, or benzothienyl;
- or R6 is hydroxyalkyl, polyhydroxyalkyl, or 2-pyridyl.
8 more elements
A compound having a general formula selected from a group consisting of:
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R3 is hydrogen, alkyl, alkenyl, or aryl;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, or aryl;
- R7 and R8 are independently hydrogen, alkyl, allyl, aryl, hydroxyl, alkoxy, aryloxy, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino or alkoxy;
- Ra and Rb are independently hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation.
- wherein at least:
- R3 is aryl;
- or R4 is furyl, thienyl, pyrrolyl, benzofuryl, or benzothienyl.
7 more elements
A compound having a general formula:
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R3 is hydrogen, alkyl, alkenyl, or aryl;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, or aryl;
- R9 is hydrogen, alkyl, aryl, alkenyl, alkynyl, allenyl, hydroxyalkyl, or polyhydroxyalkyl;
- Ra and Rb are independently hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation.
4 more elements
A compound having a general formula:
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R3 is hydrogen, alkyl, alkenyl, or aryl;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, or aryl;
- Ra and Rb are each independently hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation;
- G1-G4 are each independently hydrogen, alkyl, aryl, hydroxyl, alkoxy, aryloxy, chloro, bromo, fluoro, dialkylamino, acylamino, or sulfonylamino.
4 more elements
A compound of general formula:
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl, aryl, alkenyl, alkynyl, allenyl, formyl, acyl, aminoacyl, carboxy or alkoxyacyl;
- R6 is hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl, aryl, pyridyl, alkenyl, alkynyl, allenyl, formyl, acyl, aminoacyl, carboxy or alkoxyacyl;
- Ra-Rd are each independently hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation.
3 more elements
A compound having a general formula selected from a group consisting of:
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, or aryl;
- R7 and R8 are each independently hydrogen, alkyl, allyl, aryl, hydroxyl, alkoxy, aryloxy, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino or alkoxy;
- Ra-Rd are independently hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation.
3 more elements
A compound having a general formula:
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, or aryl;
- R9 is hydrogen, alkyl, aryl, alkenyl, alkynyl, allenyl, hydroxyalkyl, or polyhydroxyalkyl;
- Ra-Rd are independently selected from a group consisting of hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation.
3 more elements
A compound having a general formula:
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, or aryl;
- Ra-Rd are independently hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation;
- G1-G4 are independently hydrogen, alkyl, aryl, hydroxyl, alkoxy, aryloxy, chloro, bromo, fluoro, dialkylamino, acylamino, or sulfonylamino.
3 more elements
A method for the preparation of an amino phosphonate of the general formula:
- by reacting:
- an amino phosphonate of formula
- a carbonyl compound of formula
- and an organoboron compound of formula
- wherein:
- R2 is hydrogen, alkyl, allyl, aryl, acyl, sulfonyl, amino, alkylamino, dialkylamino, acylamino, sulfonylamino, or alkoxy;
- R3 is hydrogen, alkyl, alkenyl, aryl, phosphonic acid, phosphonate or phosphonamido;
- R4 is alkyl, aryl, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, allyl, alkenyl, alkynyl, or allenyl;
- R5 is hydrogen, alkyl, or aryl;
- R6 is hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl, aryl, pyridyl, alkenyl, alkynyl, allenyl, formyl, acyl, aminoacyl, carboxy or alkoxyacyl;
- Ra and Rb are independently hydrogen, alkyl, aryl, ammonium, tetraalkyl ammonium or a metal cation;
- Z1 and Z2 are independently hydroxyl, alkoxy, aryloxy, amino or sulfonylamino, provided that Z1 and Z2 can also be joined together forming a ring;
- and
- M is a cation selected from a group consisting of the cations of:
- potassium, sodium, lithium, cesium, magnesium, ammonium, tetraalkyl ammonium and aryl-alkyl ammonium,
- wherein at least:
- R3 is aryl;
- or R4 is furyl, thienyl, pyrrolyl, benzofuryl, or benzothienyl;
- or R6 is hydroxyalkyl, polyhydroxyalkyl, or 2-pyridyl.
16 more elements
Dependencies are inferred from the claim text.