865231-46-5Relevant academic research and scientific papers
Synthetic method of AMG837 and chiral gamma-methyl benzene pentanol
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Paragraph 0027; 0029; 0039-0040, (2021/01/29)
The invention discloses a synthetic method of AMG837 and chiral gamma methyl benzene pentanol, and the method comprises the following steps: by using racemic propargyl carbonate and a methane triformate compound as initial raw materials, using bis-(1, 5-c
Method for synthesizing AMG837
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, (2020/01/03)
The invention relates to a method for synthesizing a compound, in particular to a method for synthesizing AMG837. The method comprises the following steps: a step of preparing an intermediate D by a reaction of an intermediate E with propyne; a step of de
Asymmetric synthesis of chiral β-alkynyl carbonyl and sulfonyl derivatives: Via sequential palladium and copper catalysis
Trost, Barry M.,Masters, James T.,Taft, Benjamin R.,Lumb, Jean-Philip
, p. 6217 - 6231 (2016/08/31)
We present a full account detailing the development of a sequential catalysis strategy for the synthesis of chiral β-alkynyl carbonyl and sulfonyl derivatives. A palladium-catalyzed cross coupling of terminal alkyne donors with acetylenic ester, ketone, a
Discovery of the imidazole-derived GPR40 agonist AM-3189
Ma, Zhihua,Lin, Daniel C.-H.,Sharma, Rajiv,Liu, Jinqian,Zhu, Liusheng,Li, An-Rong,Kohn, Todd,Wang, Yingcai,Liu, Jiwen,Bartberger, Michael D.,Medina, Julio C.,Zhuang, Run,Li, Frank,Zhang, Jane,Luo, Jian,Wong, Simon,Tonn, George R.,Houze, Jonathan B.
, p. 15 - 20 (2015/12/18)
As a follow-up to the GPR40 agonist AMG 837, which was evaluated in clinical trials for the treatment of type II diabetes, further optimization led to the discovery of AM-3189 (13k). AM-3189 is representative of a new class of compounds with minimal CNS penetration, superior pharmacokinetic properties and in vivo efficacy comparable to AMG 837.
Iridium-catalyzed enantioselective allylic alkynylation
Hamilton, James Y.,Sarlah, David,Carreira, Erick M.
supporting information, p. 7532 - 7535 (2013/07/26)
No leaving group needed: With an Ir(P,olefin) complex as catalyst, the direct enantioselective allylic alkynylation of secondary allylic alcohols with potassium alkynyltrifluoroborates as alkynylating reagents has been achieved. High levels of enantiosele
AMG 837: A potent, orally bioavailable GPR40 agonist
Houze, Jonathan B.,Zhu, Liusheng,Sun, Ying,Akerman, Michelle,Qiu, Wei,Zhang, Alex J.,Sharma, Rajiv,Schmitt, Michael,Wang, Yingcai,Liu, Jiwen,Liu, Jinqian,Medina, Julio C.,Reagan, Jeff D.,Luo, Jian,Tonn, George,Zhang, Jane,Lu, Jenny Ying-Lin,Chen, Michael,Lopez, Edwin,Nguyen, Kathy,Yang, Li,Tang, Liang,Tian, Hui,Shuttleworth, Steven J.,Lin, Daniel C.-H.
supporting information; experimental part, p. 1267 - 1270 (2012/03/26)
The discovery that certain long chain fatty acids potentiate glucose stimulated insulin secretion through the previously orphan receptor GPR40 sparked interest in GPR40 agonists as potential antidiabetic agents. Optimization of a series of β-substituted p
Cooperative activation of alkyne and thioamide functionalities; Direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides
Yazaki, Ryo,Kumagai, Naoya,Shibasaki, Masakatsu
, p. 1778 - 1790 (2012/02/02)
A detailed study of the direct catalytic asymmetric conjugate addition of terminal alkynes to α,β-unsaturated thioamides is described. A soft Lewis acid/hard Bronsted base cooperative catalyst, comprising [Cu(CH3CN)4]PF6,
Development of a scalable synthesis of a GPR40 receptor agonist
Walker, Shawn D.,Borths, Christopher J.,Divirgilio, Evan,Huang, Liang,Liu, Pingli,Morrison, Henry,Sugi, Kiyoshi,Tanaka, Masahide,Woo, Jacqueline C. S.,Faul, Margaret M.
, p. 570 - 580 (2011/12/04)
Early process development and salt selection for AMG 837, a novel GPR40 receptor agonist, is described. The synthetic route to AMG 837 involved the convergent synthesis and coupling of two key fragments, (S)-3-(4-hydroxyphenyl) hex-4-ynoic acid (1) and 3-
Enantioselective synthesis of a GPR40 agonist AMG 837 via catalytic asymmetric conjugate addition of terminal alkyne to α,β-unsaturated thioamide
Yazaki, Ryo,Kumagai, Naoya,Shibasaki, Masakatsu
, p. 952 - 955 (2011/04/25)
A concise enantioselective synthetic route to a potent GPR40 agonist AMG 837 is described. The crucial catalytic asymmetric conjugate addition of terminal alkyne was promoted by a soft Lewis acid/hard Bronsted base cooperative catalyst, allowing efficient
Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders
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Page/Page column 28, (2010/02/15)
The present invention provides compounds useful, for example, for modulating insulin levels in a subject and that have the general formula [in-line-formulae]Q-L1-P-L2-M-X-L3-A [/in-line-formulae] wherein the definitions of
