Cycloalkyl substituted polyamines for cancer therapy and methods of synthesis therefor
AssigneeSLIL Biomedical Corporation
InventorsBenjamin Frydman, Aldonia L. Valasinas, Andrei V. Blokhin, Aparajita Sarkar, Hirak S. Basu, Venodhar K. Reddy, Laurence J. Marton, Yu Wang
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Abstract
Conformationally restricted polyamine compounds useful in treatment of cancer and other diseases marked by abnormal cell proliferation are disclosed. Improved methods of synthesizing such compounds are also disclosed. In one method of the invention, a carbene-bearing or carbene equivalent-bearing compound is reacted with the double bond of an alkene compound to form a cyclopropyl ring as the first step in the synthesis.
Claims35
A method for making a polyamine containing a cyclopropyl group, comprising:
- adding a carbene-bearing or carbene equivalent-bearing compound across a double bond of an alkene compound to form a cyclopropyl ring, where the carbene-bearing or carbene equivalent-bearing compound, or the alkene compound, or both have additional functional groups which can be reacted in further steps;
- optionally performing further chemical reactions on the additional functional groups incorporated into the cyclopropane ring from the carbene-bearing or carbene equivalent-bearing compound, or from the alkene compound, or both;
- and
- reacting amino-bearing groups with the additional functional groups incorporated into the cyclopropane ring from the carbene-bearing or carbene equivalent-bearing compound, or from the alkene compound, or both.
A compound of the formula:
- E-NH—B-A-B—NH—B-A-B—NH—B-A-B—NH(—B-A-B—NH)x-E
- wherein A is independently selected from the group consisting of a single bond,
- C2-C6 alkyl, C2-C6 hydroxyalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloaryl, and C3-C6 cycloalkenyl;
- B is independently selected from the group consisting of a single bond, C1-C6 alkyl, C1-C6 hydroxyalkyl, and C2-C6 alkenyl;
- E is independently selected from the group consisting of H, C1-C6 alkyl, C1-C6 hydroxyalkyl, C2-C6 alkenyl, and C2-C6 alkynyl;
- and
- x is an integer from 0 to 16;
- with the proviso that at least one A moiety is cyclopropyl, and that each —B-A-B— subunit contains at least two carbon atoms;
- and all salts and stereoisomers thereof.
Dependencies are inferred from the claim text.