Synthesis of diindolylmethanes and indolo[3,2-b]carbazoles, compounds formed thereby, and pharmaceutical compositions containing them
US9969686B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Aug 5, 2015 |
| Grant date | May 15, 2018 |
| Priority date | — |
| Expiry date | Aug 5, 2035 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D405/14
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or unsubstituted indol or a substituted or unsubstituted pyrrole, in the presence of a metal-containing catalyst, for a time and at a temperature to cause an annulation/arylation cascade reaction that yields a diindolylmethane or a indolyl/pyrrolylmethane. The resulting compounds are effective to modulate activity of arylhydrocarbon receptors, to inhibit activity of PCSK9, and to stimulate secretion of glucagon-like peptide 1 in mammals.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.