33301-41-6Relevant academic research and scientific papers
A Single-Step Synthesis of Azetidine-3-amines
Wang, Brian J.,Duncton, Matthew A. J.
, p. 13317 - 13323 (2020)
The azetidine group is frequently encountered within contemporary medicinal chemistry. However, the introduction of an azetidine can be synthetically challenging. Herein, a straightforward synthesis of azetidine-3-amines, starting from a bench stable, commercial material is presented. The reaction tolerates common functionality and proceeds in moderate-to-high yield with secondary amines, and moderate-to-low yield with primary amines. The methodology compares favorably to alternative procedures and can be utilized in "any-stage"functionalization, including late-stage azetidinylation of approved drugs and other compounds with pharmacological activity.
An efficient two-step synthesis of 3-amino-1-benzhydrylazetidine
Li, Bryan,Witt, Michael F.,Brandt, Thomas A.,Whritenour, David
, p. 478 - 480 (2006)
A streamlined process for the synthesis of 3-amino-1-benzhydrylazetidine is described. Commercially available 1-benzhydrylazetidin-3-ol was reacted with methanesulfonyl chloride in the presence of triethylamine in acetonitrile, upon quench with water, the
INHIBITOR CONTAINING BICYCLIC DERIVATIVE, PREPARATION METHOD THEREFOR AND USE THEREOF
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Paragraph 0753; 0760-0762; 0819-0822, (2022/04/03)
Provided are an inhibitor containing a bicyclic derivative, a preparation method therefor and the use thereof. In particular, involved are a compound shown by general formula (I), a preparation method therefor, a pharmaceutical composition thereof, and the use thereof as an RET inhibitor in the treatment of cancers, inflammations, chronic liver diseases, diabetes, cardiovascular diseases, AIDS, and other related diseases, wherein each substituent in general formula (I) has the same definition as that given in the description.
NEW TRIAZOLYL DERIVATIVES AS GABA A ALPHA5 PAM
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Page/Page column 73, (2021/11/20)
The invention provides novel compounds having the general formula (I) or (II) wherein R1, R2, R3, X, Y and Z are as described herein, compositions including the compounds and methods of using the compounds.
Efficient Manufacturing Process for the Selective Estrogen Receptor Degrader GDC-9545 (Giredestrant) via a Crystallization-Driven Diastereoselective Pictet-Spengler Condensation
Chung, Cheol K.,Clagg, Kyle,Dalziel, Michael E.,Fettes, Alec,Finet, Laure,Gosselin, Francis,Jenny, Christian,Kammerer, Michael,Lim, Ngiap-Kie,Mack, Kyle A.,McClory, Andrew,Wuitschik, Georg,Xu, Jie,Zhang, Haiming,Angelaud, Rémy
, (2021/11/24)
GDC-9545 is a selective estrogen receptor degrader that is being developed as a treatment for ER+/HER2- breast cancer. A robust, convergent manufacturing process for GDC-9545 was developed. The process features a Wenker aziridine synthesis to produce the key starting material tryptamine 11, a highly efficient C-N coupling between aminoazetidine 9 and 2,6-difluoro-4-bromobenzaldehyde diethyl acetal (33) to construct key intermediate 10, and a crystallization-driven diastereoselective Pictet-Spengler reaction to furnish the active pharmaceutical ingredient GDC-9545·tartrate.
Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines
Roagna, Giulia,Ascough, David M. H.,Ibba, Francesco,Vicini, Anna Chiara,Fontana, Alberto,Christensen, Kirsten E.,Peschiulli, Aldo,Oehlrich, Daniel,Misale, Antonio,Trabanco, Andrés A.,Paton, Robert S.,Pupo, Gabriele,Gouverneur, Véronique
supporting information, p. 14045 - 14051 (2020/09/16)
Ammonium salts are used as phase-Transfer catalysts for fluorination with alkali metal fluorides. We now demonstrate that these organic salts, specifically azetidinium triflates, are suitable substrates for enantioselective ring opening with CsF and a chiral bis-urea catalyst. This process, which highlights the ability of hydrogen bonding phase-Transfer catalysts to couple two ionic reactants, affords enantioenriched γ-fluoroamines in high yields. Mechanistic studies underline the role of the catalyst for phase-Transfer, and computed transition state structures account for the enantioconvergence observed for mixtures of achiral azetidinium diastereomers. The N-substituents in the electrophile influence the reactivity, but the configuration at nitrogen is unimportant for the enantioselectivity.
NEW ISOXAZOLYL ETHER DERIVATIVES AS GABA A ALPHA5 PAM
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Page/Page column 129, (2020/01/08)
The invention provides novel compounds having the general formula (I) or (II) wherein R2, R3, R5, R99, W, Y and Z are as described herein, compositions including the compounds and methods of using the compounds.
3-((Hetera)cyclobutyl)azetidines, "stretched" Analogues of Piperidine, Piperazine, and Morpholine: Advanced Building Blocks for Drug Discovery
Feskov, Illia O.,Chernykh, Anton V.,Kuchkovska, Yuliya O.,Daniliuc, Constantin G.,Kondratov, Ivan S.,Grygorenko, Oleksandr O.
, p. 1363 - 1371 (2019/02/07)
Four 3-((hetera)cyclobutyl)azetidine-based isosteres of piperidine, piperazine, and morpholine were designed and synthesized on up to gram scale. The key step of the synthetic sequence included cyclization of N-protected 2-(azetidin-3-yl)propane-1,3-diol
TARGETING COMPOUNDS
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Paragraph 0226, (2019/07/19)
The disclosure provides, at least in part, liver, intestine and/or kidney-targeting compounds and their use in treating liver, intestine and/or kidney disorders, such as non-alcoholic steatohepatitis, alcoholic steatohepatitis, hepatocellular carcinoma, liver cirrhosis, and hepatitis B; and/or chronic kidney disease, glomerular disease such as IGA nephropathy, lupus nephritis, or polycystic kidney disease. The compounds are contemplated to have activity against methionyl aminopeptidase 2.
COMBINATION THERAPIES FOR TREATMENT OF CANCER
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Paragraph 319, (2016/04/09)
Combination therapies for treatment of cancers associated with mutations in the KRAS gene are provided. Compositions comprising therapeutic agents for treatment of cancers associated with mutations in the KRAS gene are also provided.
