公开(公告)号：US10730833B2

公开(公告)日：2020-08-04

申请号：US15946066

申请日：2018-04-05

Applicant: Wisconsin Alumni Research Foundation

Inventor： Weiping Tang ,  Xiaoxun Li ,  Dongxu Shu ,  Gabrielle N. Winston-McPherson

IPC: C07D209/14 ,  C07D403/06 ,  C07D405/14 ,  C07D209/12

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.

公开(公告)号：US10174008B2

公开(公告)日：2019-01-08

申请号：US15545858

申请日：2015-12-03

Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATION

Inventor： Weiping Tang ,  Xiaoxun Li

IPC: B01J31/22 ,  B01J31/40 ,  C07B37/10 ,  C07B51/00 ,  C07D209/08 ,  C07D405/08

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(1)-containing catalyst.

公开(公告)号：US09969686B2

公开(公告)日：2018-05-15

申请号：US14818960

申请日：2015-08-05

Applicant: Wisconsin Alumni Research Foundation

Inventor： Weiping Tang ,  Xiaoxun Li ,  Dongxu Shu ,  Gabrielle N. Winston-McPherson

IPC: C07D403/06 ,  C07D209/14 ,  C07D405/14

CPC classification number: C07D209/14 ,  C07D209/12 ,  C07D403/06 ,  C07D405/14

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.

公开(公告)号：US20180002318A1

公开(公告)日：2018-01-04

申请号：US15545858

申请日：2015-12-03

Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATION

Inventor： Weiping Tang ,  Xiaoxun Li

IPC: C07D405/08 ,  B01J31/40 ,  B01J31/22 ,  C07B37/10 ,  C07D209/08 ,  C07B51/00

CPC classification number: C07D405/08 ,  B01J31/2265 ,  B01J31/4046 ,  B01J2231/325 ,  C07B37/10 ,  C07B51/00 ,  C07D209/08 ,  Y02P20/55

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.

公开(公告)号：US20180222861A1

公开(公告)日：2018-08-09

申请号：US15946066

申请日：2018-04-05

Applicant: Wisconsin Alumni Research Foundation

Inventor： Weiping Tang ,  Xiaoxun Li ,  Dongxu Shu ,  Gabrielle N. Winston-McPherson

IPC: C07D209/14 ,  C07D405/14 ,  C07D403/06

CPC classification number: C07D209/14 ,  C07D209/12 ,  C07D403/06 ,  C07D405/14

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.