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US 6,638,924 B2Granted
Metallotexaphyrin derivatives
AssigneePharmacyclics, Inc.
InventorsTarak D. Mody, Joshua Galanter
Life of this patent
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Abstract
Novel derivatives of metallotexaphyrins are prepared by modifying the apical ligands associated with the central metal component of a metallotexaphyrin.
Claims37
A compound of the Formula:
- wherein:
- M is a monovalent, divalent, trivalent, or tetravalent metal cation;
- AL is an apical ligand;
- with the proviso that AL is not derived from acetic acid, nitric acid, or hydrochloric acid;
- n is 1 when M is a divalent cation, or n is 2 when M is a trivalent cation;
- R1, R2, R3, R4, R5, R6, R7, R8, and R9, are independently chosen from the group consisting of hydrogen, halogen, hydroxyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted haloalkyl;
- alkylalkoxy, nitro, acyl, optionally substituted alkoxy, saccharide, optionally substituted amino, carboxyl, optionally substituted carboxyalkyl, optionally substituted carboxyamide, optionally substituted carboxyamidealkyl, optionally substituted heterocycle, optionally substituted cycloalkyl, optionally substituted arylalkyl, optionally substituted heteroarylalkyl, optionally substituted heterocycloalkylalkyl;
- and a group —X—Y, in which X is a covalent bond or a linker and Y is a catalytic group, a chemotherapeutic agent, or a site-directing molecule, and;
- R5, R10, R11, and R12 are independently hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted carboxyalkyl, or optionally substituted carboxyamidealkyl;
- with the proviso that the halogen is other than iodide and the haloalkyl is other than iodoalkyl.
7 more elements
A process for preparing a metallotexaphyrin having the formula:
- (T−M)n+(AL−)n
- wherein:
- T is a texaphyrin;
- M is a divalent or trivalent metal cation constrained within the binding cavity of the texaphyrin;
- AL is an apical ligand;
- and
- n is an integer of 1-5;
- comprising:
- a) contacting an apical ligand (AL)H with a quartenary amine resin;
- b) contacting the resin complex produced in step a) with a metallotexaphyrin of the formula:
- (T−M)n+(AL1−)n
- in which T and M are as defined above;
- (AL1) represents a displaceable apical ligand;
- and
- n is an integer of 1-5.
12 more elements
A process for preparing a metallotexaphyrin having the formula:
- (T−M)n+(AL−)n
- wherein:
- T is a texaphyrin;
- M is a divalent or trivalent metal cation constrained within the binding cavity of the texaphyrin;
- AL is an apical ligand;
- and
- n is an integer of 1-5;
- comprising:
- contacting a metallotexaphyrin of the formula:
- (T−M)n+(AL1−)n
- in which T and M are as defined above;
- (AL1) represents a displaceable apical ligand;
- and
- n is an integer of 1-5;
- with an excess of an apical ligand (AL)H;
- at a temperature of 20-100° C.
13 more elements
Dependencies are inferred from the claim text.