Colchicine derivatives, methods and uses thereof

Patent metadata

Field	Value
Publication number	US-9458101-B2
Application number	US-201013392454-A
Country	US
Kind code	B2
Filing date	Jul 30, 2010
Priority date	Aug 26, 2009
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

The invention relates to colchicine derivatives, methods and uses thereof for treatment of cancer. In certain embodiments, the colchicine derivative comprises a compound of Formula I:

First claim

What is claimed is:

1. A compound of Formula XE and/or XF:

a pharmaceutically-acceptable salt, hydrate, solvate, tautomer, optical isomer, or combination thereof,
wherein:
when the compound is Formula XE, R 3 is selected from a halo group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic;
when the compound is Formula XF, R 3 is selected from H, a halo group, a substituted or unsubstituted hydrocarbon group, a substituted or unsubstituted heterogeneous group, a substituted or unsubstituted carbocyclic group, a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aromatic, or a substituted or unsubstituted heteroaromatic; and
wherein R 10 is a methyl group.

2. The compound according to claim 1 , wherein R 3 is selected from a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 2 -C 6 alkenyl, or C 1 -C 6 alkylene-O-alkyl.

3. The compound according to claim 1 , wherein R 3 is selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted carbocyclic group, or a substituted or unsubstituted heterocyclic group.

4. The compound according to claim 1 ,
wherein R 3 is selected from a substituted or unsubstituted alkyl, CH 2 OH, a substituted or unsubstituted haloalkyl, a substituted or unsubstituted hydroxyalkyl, a substituted or unsubstituted cyanoalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, a substituted or unsubstituted alkylcycloalkyl, a substituted or unsubstituted alkylcycloalkenyl, a substituted or unsubstituted heterocycloalkyl, a substituted or unsubstituted alkylheterocycloalkyl, a substituted or unsubstituted heterocycloalkenyl, a substituted or unsubstituted alkylheterocycloalkenyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkylaryl, a substituted or unsubstituted alkylheteroaryl, alkylene-O-alkyl, alkylene-O-cycloalkyl, alkylene-O-heterocycloalkyl, alkylene-O-alkylene-cycloalkyl, or alkylene-O-alkyleneheterocycloalkyl.

5. The compound according to claim 1 , wherein R 3 is selected from a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 2 -C 6 alkenyl, a substituted or unsubstituted C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylene-O-alkyl, a substituted or unsubstituted alkylcycloalkyl, a substituted or unsubstituted alkylaryl, or a substituted or unsubstituted alkylheteroaryl.

6. A method for treating a cancer in a mammal, comprising administering to the mammal a therapeutically effective amount of the compound according to claim 1 .

7. The method according to claim 6 , wherein the cancer is selected from lung cancer, cervical cancer, ovarian cancer, cancer of CNS, skin cancer, prostate cancer, sarcoma, breast cancer, leukemia, colorectal cancer, head cancer, neck cancer or kidney cancer.

Assignees

• Tuszynski Jack
• Mane Jonathan Y
• Huzil John Torin
• Tomanek Boguslaw
• Bartusik Dorota
• Nat Res Council Canada

Inventors

• Tuszynski Jack
• Mane Jonathan Y
• Huzil John Torin
• Tomanek Boguslaw
• Bartusik Dorota

Classifications

• A61P35/02

  specific for leukemia · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• G01N2500/10

  involving cells · CPC title

• C07C323/61

  having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton · CPC title

• G01N33/5088

  of vertebrates · CPC title