- A Modular Approach to Dibenzo-fused ?-Lactams: Palladium-Catalyzed Bridging-C?H Activation
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Tricyclic ring systems possessing a dibenzo structure joined to a seven-membered heterocyclic ring frequently show important biological activities. However, a modular approach to these molecules based on efficient intermolecular reaction of readily available chemicals is lacking. Herein, an unprecedented palladium-catalyzed formal [4+3] annulation for modular construction of these tricyclic systems is described. This reaction features easily accessible reactants (o-haloarylaldehydes and N-tosylhydrazones), broad substrate scope, and excellent functional group compatibility. The synthetic potential is demonstrated by the easy scale-up reactions, late-stage modification of complex molecules, and collective synthesis of bioactive molecules and approved drugs.
- Huang, Xueliang,Ma, Liyao,Xia, Jiajin,Xin, Luoting,Yu, Yinghua,Zhu, Lei
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supporting information
p. 18261 - 18266
(2020/08/21)
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- 2,3,4,9-TETRAHYDRO-1H-CARBAZOLE DERIVATIVES AS CRTH2 RECEPTOR ANTAGONISTS
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The invention relates to novel tetrahydro-lH-carbazole derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and methods of treatment comprising administration of said compounds to patients.
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Page/Page column 51-52
(2008/06/13)
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- INDOL-1-YL-ACETIC ACID DERIVATIVES
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The invention relates to indol-1-yl-acetic acid derivatives and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and methods of treatment comprising administration of said compounds.
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Page/Page column 70
(2010/02/14)
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- Novel derivatives and analogues of galanthamin
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New compounds of general formula I 1
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- Synthesis and structure-activity relationship of 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives: A novel series of 5-HT2A/2C receptor antagonists. Part 1
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The synthesis of a series of novel 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives as well as their 5-HT2A/2C and H1 receptor binding affinities are described. The in vivo activity as potential anxiolytics of the synthesised compounds was measured in a mCPP challenge test. One of the compounds, 2a, proved to be a potent 5-HT2A/2C receptor antagonist showing as well oral activity and therefore could be considered as a potential anxiolytic/antidepressant agent.
- Andres,Alcazar, Jesus,Alonso, Jose M.,Diaz, Adolfo,Fernandez, Javier,Gil, Pilar,Iturrino, Laura,Matesanz, Encarna,Meert, Theo F.,Megens, Anton,Sipido, Victor K.
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p. 243 - 248
(2007/10/03)
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- Development of a safe and scalable amine-to-nitrone oxidation: A key step in the synthesis of R107500
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The stepwise optimization towards a safe, reproducible, and high-yielding oxidation of azepine 2 into the prochiral nitrone 4 is described, with emphasis on the elimination of Davis reagent 3. m-Chloroperoxybenzoic acid (mCPBA) was found to be an elegant and scalable alternative oxidant regarding safety, yield, and easy workup procedures. Nitrone 4 was obtained in 95% yield and used without purification or isolation in the cycload-dition step to provide oxazolidone 6 in high yield. The process was scaled up successfully to an 800-L scale (60 mol of starting material).
- Stappers, Fred,Broeckx, Rudy,Leurs, Stef,Den Bergh, Leo Van,Agten, Jos,Lambrechts, Annemie,Van den Heuvel, Dirk,De Smaele, Dirk
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p. 911 - 914
(2013/09/06)
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- Substituted tetracyclic azepine derivatives
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This invention concerns the compounds of formula (I), the pharmaceutically acceptable salts and stereoisomeric forms thereof, and also the N-oxide forms thereof. STR1 wherein: R1 and R2 each independently are hydrogen; C1-6 alkyl; C1-6 alkylcarbonyl; trihalomethylcarbonyl; C1-6 alkyl substituted with hydroxy, C1-6 alkyloxy, carboxyl, C1-6 alkylcarbonyloxy, C1-6 alkyloxycarbonyl or aryl; or R1 and R2 taken together with the nitrogen atom to which they are attached may form a morpholinyl ring or an optionally substituted heterocycle; R3, R4, R5, R6, R9, R10, R11 or R12 each independently are hydrogen, halo, cyano, hydroxy, trifluoromethyl, trifluoromethoxy, carboxyl, nitro, amino, mono- or di(C1-6 alkyl)-amino, C1-6 alkylcarbonylamino, aminosulfonyl, mono- or di(C1-6 alkyl)-aminosulfonyl, C1-6 alkyl, C1-6 alkyloxy, C1-6 alkylcarbonyl, C1-6 alkyloxy-carbonyl; R7 and R8 are each independently hydrogen, hydroxy, C1-6 alkyl, C1-6 alkyloxy or R7 and R8 taken together may form mono- or di(cyano)methylene, or together with the carbon atom to which they are attached form a carbonyl or a spiro substituent; or R7 and R8 taken together may form methylene; R13 is hydrogen, C1-6 alkyl, or trifluoromethyl; R14 is hydrogen, C1-6 alkyl, cyano, or trifluoromethyl; n is zero to 6. These compounds were tested as mCPP-antagonists in rats. The compounds of formula (I) may be used as therapeutic agents in the treatment or the prevention of CNS disorders, cardiovascular disorders or gastrointestinal disorders.
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