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：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：US20160039754A1

公开(公告)日：2016-02-11

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: 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.

Abstract translation: 描述了制备二吲哚基甲烷和吲哚基/吡咯基甲烷的方法。该方法包括以下步骤：将包含芳基炔丙基部分和胺保护的，取代或未取代的苯胺部分的醚与取代或未取代的吲哚或取代或未取代的吡咯， 含金属催化剂的存在一段时间和在一定温度下引起产生二吲哚基甲烷或吲哚基/吡咯基甲烷的环状/芳基化级联反应。 所得化合物有效调节芳基烃受体的活性，抑制PCSK9的活性，并刺激哺乳动物中胰高血糖素样肽1的分泌。

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.