- PIPERAZINE SUBSTITUTED AZAPINE DERIVATIVES AND USES THEREOF
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The present disclosure relates to compounds of Formula (I) and (II): and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for modulating H1 and 5-HT2A receptors and are to be used in the treatment of sleep disorders, such as sleep fragmentation, disturbed sleep/arousals, and arousal threshold.
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Paragraph 1020-1022
(2021/04/23)
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- 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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- Synthetic method of epinastine hydrochloride
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The invention relates to a synthesis method of epinastine hydrochloride. The method comprises the following steps: reacting phthalic anhydride with aniline to obtain a compound 1, reacting the compound 1 with polyphosphoric acid under certain conditions to perform cyclization to obtain a compound 2, reducing carbonyl of the compound 2 under certain conditions to obtain a compound 3, and carrying out chlorination reaction on the compound 3 to obtain a compound 4, carrying out cyano substitution reaction on the compound 4 to obtain a compound 5, reducing the compound 5 by using a carbon-nitrogenunsaturated bond to obtain a compound 6, reacting the compound 6 with cyanogen bromide, and forming hydrochloride by using hydrochloric acid to obtain a compound 7; according to the method, the epinastine hydrochloride is prepared from bulk chemical products, is extremely low in price and mild in reaction condition, avoids the use of azide compounds, and the method is suitable for large-scale industrial production. The prepared epinastine hydrochloride is high in purity and low in cost, and has higher market competitiveness.
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Paragraph 0035-0036
(2020/12/15)
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- Preparing method for 5,11-dihydro-6H-dibenzo[b,e]azepine-6 ketone
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The invention discloses a preparing method for 5,11-dihydro-6H-dibenzo[b,e]azepine-6 ketone. The preparing method includes the steps that raw materials of 5H-dibenzo[b,e]azepine-6 and 11-diketone are added into a reaction container, then a reaction solvent, zinc powder, organic acid and a catalyst are sequentially added, the temperature is started to be increased, and a stirring reaction is started when the temperature is the reaction temperature; the reaction is completed, the obtained reaction liquid is subjected to pressure reduction suction filtration, filtered liquid is extracted with trichloromethane, washing and drying are sequentially carried out after extraction, a trichloromethane solvent is subjected to pressure reduction recycling, and the 5,11-dihydro-6H-dibenzo[b,e]azepine-6 ketone is obtained. Compared with the prior art, the per-kilogram cost of the 5,11-dihydro-6H-dibenzo[b,e]azepine-6 ketone prepared with the method is reduced by 800 yuan to 1,000 yuan, the total yield is increased by 3% to 5%, industrial production can be directly achieved, and the remarkable economic benefits are achieved.
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Paragraph 0064; 0065; 0066; 0067; 0032-0063; 0068-0071
(2017/04/29)
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- MeOTf- and TBD-Mediated Carbonylation of ortho-Arylanilines with CO2 Leading to Phenanthridinones
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Carbonylation of o-arylanilines utilizing CO2 as a carbonyl source for the synthesis of important phenanthridinones with a free (NH)-lactam motif has been described under metal-free condition. A range of o-arylanilines were transformed to the corresponding phenanthridinones in high yields.
- Wang, Sheng,Shao, Peng,Du, Gaixia,Xi, Chanjuan
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p. 6672 - 6676
(2016/08/16)
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- Set-up of a new series of HDAC inhibitors: The 5,11-dihydrodibenzo[b,e] azepin-6-ones as privileged structures
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We report here the strategy used in our research group to find a new class of histone deacetylase (HDAC) inhibitors. A series of 5,11-dihydrodibenzo[b,e] azepine-6-ones alkylated on the amide nitrogen with an alkyl chain bearing an hydroxamic acids moiety at the end, has been designed (based upon the general motif for HDAC inhibitors), synthesized and tested. This allowed us to identify a new series of submicromolar HDAC inhibitors, which showed antiproliferative activity on HCT-116 colon carcinoma cells.
- Bigioni, Mario,Ettorre, Alessandro,Felicetti, Patrizia,Mauro, Sandro,Rossi, Cristina,Maggi, Carlo Alberto,Marastoni, Elena,Binaschi, Monica,Parlani, Massimo,Fattori, Daniela
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scheme or table
p. 5360 - 5362
(2012/09/22)
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- Dibenzo-fused seven-membered nitrogen heterocycles by a tandem reduction-lactamization reaction
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Efficient syntheses of dibenz[b,f][1,4]oxazepin-11(10H)-one, 5,10-dihydro-11H-dibenzo[b,e][1,4]-diazepin-11-one and 5,11-dihydro-6H-dibenz[b, e]azepin-6-one are described using a tandem reduction-lactamization sequence. Precursors for these ring systems are available in 1-3 steps using nucleophilic aromatic substitution and Ullmann coupling methodology. Direct reduction-lactamization of these compounds using iron powder in acetic acid at 115° affords the target heterocycles in ≥90% yield.
- Bunce, Richard A.,Schammerhorn, James E.
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p. 1031 - 1035
(2007/10/03)
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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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- Synthesis, conformational analysis, and molecular structure of 5-ethyl-5,6-dihydro-11H-dibenzoazepine-6-thione
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5-Ethyl-5,6-dihydro-11H-dibenzoazepine-6-thione has been synthesized and studied in the solid state and in solution by X-ray diffraction and 1H DNMR, respectively.The crystals are monoclinic, P21/n, a=9.642(1), b=13.757(2), c=9.889(2) Angstroem, β=98.57(1)o, Z=4.The structure has been solved by direct methods and refined to an R value of 0.040 for 1771 reflections with I>2.5?(I).The seven-membered ring has a slightly deformed boat conformation.The activation barrier associated with the inversion ring has been determined, being ΔG = 21.6 kcal/mol.
- Irurre, J.,Marquillas, F.,Alvarez-Larena, A.,Piniella, J. F.
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p. 334 - 338
(2007/10/02)
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- Morphanthridines: Part III - A New Synthesis of 6-(4-Methyl-1-piperazinyl)-morphanthridine
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6-(4-Methyl-1-piperazinyl)morphanthridine (V) has been prepared by a new route involving Beckmann rearrangement of anthron-oxime (II) with PPA followed by treatment of the resultant 5,6-dihydro-6-oxomorphanthridine (III) with PCl5 and then with N-methylpiperazine.
- Sinha, Ashok Kumar,Nizamuddin, S.
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- 2-Chloromethylphenylcarbamic acid fluoride
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2-Chloromethylphenylcarbamic acid fluoride is prepared by reacting 2-chloromethylphenylisocyanate with anhydrous hydrofluoric acid. The product prepared can be reacted further with anhydrous hydrofluoric acid under pressure to prepare 2-aminodiphenylmethane-2'-carboxylic acid lactam.
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