3308-02-9Relevant academic research and scientific papers
1-Phenyl-8-azabicyclo[3.2.1]octane ethers: A novel series of neurokinin (NK1) antagonists
Huscroft, Ian T.,Carlson, Emma J.,Chicchi, Gary G.,Kurtz, Marc M.,London, Clare,Raubo, Piotr,Wheeldon, Alan,Kulagowski, Janusz J.
, p. 2008 - 2012 (2006)
1-Phenyl-8-azabicyclo[3.2.1]octane ethers are NK1 receptor antagonists. Substitution at the 6-exo-position led to high affinity NK 1 antagonists with a prolonged duration of action in vivo. Incorporation of an α-methyl substituent in
Semi-Rational Engineering of Toluene Dioxygenase from Pseudomonas putida F1 towards Oxyfunctionalization of Bicyclic Aromatics
Wissner, Julian L.,Schelle, Jona T.,Escobedo-Hinojosa, Wendy,Vogel, Andreas,Hauer, Bernhard
, p. 4905 - 4914 (2021/05/05)
Toluene dioxygenase (TDO) from Pseudomonas putida F1 was engineered towards the oxyfunctionalization of bicyclic substrates. Single and double mutant libraries addressing 27 different positions, located at the active site and entrance channel were generated. In total, 176 different variants were tested employing the substrates naphthalene, 1,2,3,4-tetrahydroquinoline, and 2-phenylpyridine. Introduced mutations in positions M220, A223 and F366, exhibited major influences in terms of product formation, chemo-, regio- and enantioselectivity. By semi-rational evolution, we lighted up the TDO capability to convert bulkier substrates than its natural substrate, at unprecedented reported conversions. Thus, the most active TDO variants were applied to biocatalytic oxyfunctionalizations of 1,2,3,4-tetrahydroquinoline, and 2-phenylpyridine, enabling the production of substantial amounts of (+)-(R)-1,2,3,4-tetrahydroquinoline-4-ol (71% isolated yield, 94% ee) and (+)-(1S,2R)-3-(pyridin-2-yl)cyclohexa-3,5-diene-1,2-diol (60% isolated yield, 98% ee), respectively. Here, we provide a set of novel TDO-based biocatalysts useful for the preparation of oxyfunctionalized bicyclic scaffolds, which are valuable to perform downstream synthetic processes. (Figure presented.).
(PYRIDIN-2-YL)AMINE DERIVATIVES AS TGF-BETA R1 (ALK5) INHIBITORS FOR THE TREATMENT OF CANCER
-
Paragraph 00260, (2020/07/15)
The present invention relates to pharmaceutical compounds, compositions and methods, especially as they are related to compositions and methods for the treatment and/or prevention of a proliferation disorder associated with ΤGFβR1 activity, such as a cancer or fibrosis. The invention provides compounds of Formula (I) and Formula (II) as further described herein having an acidic moiety that enhances tissue specificity for targeted tissues and organs. The invention includes pharmaceutical compositions, pharmaceutical combinations, and methods of use of these compounds for treating conditions including cancer or fibrosis.
Iridium-catalyzed selective hydrogenation of 3-hydroxypyridinium salts: A facile synthesis of piperidin-3-ones
Huang, Wen-Xue,Wu, Bo,Gao, Xiang,Chen, Mu-Wang,Wang, Baomin,Zhou, Yong-Gui
supporting information, p. 1640 - 1643 (2015/04/14)
The selective hydrogenation of 3-hydroxypyridinium salts has been achieved using a homogeneous iridium catalyst, providing a direct access to 2- and 4-substituted piperidin-3-one derivatives with high yields, which are important organic synthetic intermediates and the prevalent structural motifs in pharmaceutical agents. Mild reaction conditions, high chemoselectivity, and easy scalability make this reaction highly practical for the synthesis of piperidin-3-ones.
INHIBITORS OF THE KYNURENINE PATHWAY
-
, (2014/12/12)
The present application provides novel inhibitors of indoleamine 2,3-dioxygenase-1 and/or indoleamine 2,3-dioxygenase-2 and/or tryptophan 2,3-dioxygenase, metabolites thereof, and phannaceutically acceptable salts or prodrugs thereof. Also provided are methods for preparing these compounds. A therapeutically effective amount of one or more of the compounds of formula (I) is useful in treating diseases resulting from dysregulation of the kynurenine pathway. Compounds of formula (I) act by inhibiting the enzymatic activity or expression of indoleamine 2,3-dioxygenase-1 and/or indoleamine 2,3-dioxygenase-2 and/or tryptophan 2,3-dioxygenase.
Photochemical transformation of a 1,2-dihydropyridin-3-one: An original tandem retro-[4+2]/[2+2] cycloaddition process
Aitken, David J.,Frongia, Angelo,Gaucher, Xavier,Ollivier, Jean,Rafique, Hummera,Sambiagio, Carlo,Secci, Francesco
, p. 2825 - 2827 (2013/06/26)
The UV irradiation of N-benzyl-2-phenyl-1,2-dihydropyridin-3-one furnished trans-1-benzyl-4-phenyl-3-vinylazetidin-2-one, a structural isomer, as the main product. A novel tandem mechanism involving a [4+2] photocycloreversion followed by a Staudinger cycloaddition reaction is proposed, and is supported with the trapping of the purported vinylketene intermediate by other imines. This process predominates in the presence of ethylene, precluding the formation of an intermolecular [2+2] cyclobutane adduct.
Convergent and selective synthesis of pyrrolidinones, piperidinones, dihydropyridinones and pyridinols from a common intermediate - Potential precursors of bioactive products
Jida, Mouhamad,Ollivier, Jean
experimental part, p. 4041 - 4049 (2009/04/14)
Titanium-mediated cyclopropanation of natural and unnatural β-amino acid derivatives provides azabicyclo[3.1.0]hexan-1-ols as mixtures of diastereomers that are separable by silica-gel chromatography. Depending on the ring cleavage procedure employed, these compounds lead efficiently to diverse intermediates for the synthesis of pharmaceuticals. Thus, depending on the experimental conditions, basic treatment can furnish racemic pyrrolidinones as a mixture of diastereomers and piperidinones. In contrast, the synthesis of optically active dihydropyridinones was achieved through a one-pot FeCl 3/AcONa reaction or performed by using bis(sym-collidine)iodine hexafluorophosphate. Furthermore, whereas the palladium-mediated hydrogenolysis of these dihydropyridinones furnished both chiral piperidinones and original pyridinols, a CeIV-promoted radical process yielded chiral tricyclic piperidinones. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Benzoamide piperidine containing compounds and related compounds
-
, (2008/06/13)
The present invention relates to certain benzoamide piperidine containing compounds and related compounds that exhibit activity as NK-1 receptor antagonists, (e.g., substance P receptor antagonists), to pharmaceutical compositions containing them, and to their use in the treatment and prevention of central nervous system disorders, inflammatory disorders, cardiovascular disorders, ophthalmic disorders, gastrointestinal disorders, disorders caused by helicobacter pylori, disorders of the immune system, urinary incontinence, pain, migraine, emesis, angiogenesis and other disorders.
Cephalosporin antibiotics
-
, (2008/06/13)
The present invention includes novel (7R)-7-(acylamino)-3-(arylthio)-3-cephem-4-carboxylic acids or their pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to
Substituted-pyridinyl cephalosporin antibiotics active against methicillin resistant bacteria
-
, (2008/06/13)
The present invention includes (7R)-7-(acylamino)-3-(substituted-pyridinyl)-3-cephem-4-carboxylic acids or their pharmacologically acceptable salts which exhibit antibiotic activity against methicillin-resistant bacteria and are therefore useful as antiba
