Synthesis of cyclopropyl indoles and cyclohepta[b]indoles, pharmaceutical compositions containing them and method of using them
AssigneeWisconsin Alumni Research Foundation
InventorsWeiping Tang, Xiaoxun Li
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Abstract
Methods of making indole analogs using a rhodium-containing catalyst are described, along with methods of using the compounds to treat hyperglycemic, hyperlipidemic, or autoimmune disorders in mammals, and corresponding pharmaceutical compositions. Disclosed herein is a method of making indoles. The method comprises contacting a reactant of formula I wherein E is a protecting group, —SO2-Aryl, or —SO2-substituted-Aryl; and R and R2 are independently selected from the group consisting of hydrogen, halo, C1-C12-alkyl and aryl; with a rhodium(l)-containing catalyst.
Claims20
A method of making indoles, the method comprising:
- contacting a reactant of formula I:
- wherein E is a protecting group, —SO2-Aryl, or —SO2-substituted-Aryl;
- and
- R1 and R2 are independently selected from the group consisting of hydrogen, halo, C1-C12-alkyl, and aryl;
- with a rhodium(I)-containing catalyst, in the presence or absence of an alkene-containing co-reactant, for a time and at a temperature to yield a product mixture comprising a compound selected from the group consisting of formula (II), (III), and (IV):
- wherein R1, R2, and E are as defined previously, and R3 is hydrogen in the absence of the alpha-alkene-containing co-reactant, and R3 is a substituent corresponding to the alkene-containing co-reactant in the presence of the alkene-containing co-reactant.
A method of treating hyperglycemic, hyperlipidemic, or autoimmune disorders in mammals, the method comprising administering to a mammal an anti-hyperglycemic-effective, anti-hyperlipidemic-effective, or anti-autoimmune-effective amount of one or more compounds selected from the group consisting of:
- wherein R1 and R2 are independently selected from the group consisting of hydrogen, halo, C1-C12-alkyl, and aryl;
- and R3 is selected from the group consisting of:
- wherein R4, R5, and R6 are each independently selected from the group consisting of hydrogen, C1-C12-alkyl, C1-C12-alkyloxy, C1-C12-haloalkyl, and C1-C12-hydroxyalkyl;
- E is a protecting group or a hydrogen atom;
- or a pharmaceutically suitable salt thereof.
Dependencies are inferred from the claim text.