- Carbon transfer reactions of functionalized oxazolidines and their open chain enamine tautomers to enamine nucleophiles. A facile synthesis of substituted pyridines and ring annulated derivatives
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Oxazolidines substituted at C-2 with -CH2-EW(-CO-, etc.) and capable of existing as ring-chain (enamine) tautomers react with cyclic, acyclic and heterocyclic enamine derivatives in a 1:1 stoi-chiometric manner to provide a versatile synthesis of substituted pyridines and their ring annulated derivatives.
- Singh, Kamaljit,Singh, Jasbir,Singh, Harjit
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- TRICYCLIC SULFONES AS ROR GAMMA MODULATORS
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There are described ROR? modulators of the formula (I), or stereoisomers, pharmaceutically acceptable salts thereof, wherein all substituents are defined herein.
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Page/Page column 16
(2021/07/31)
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- SHP2 INHIBITORS, COMPOSITIONS AND USES THEREOF
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Provided are compounds of Formula (I), methods of using the compounds as SHP2 inhibitors, and pharmaceutical compositions comprising such compounds. The compounds are useful in treating SHP2-mediated diseases.
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Page/Page column 108-109
(2021/12/30)
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- Preparation method and intermediate of hexahydroquinolinedione compound
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The invention discloses a preparation method and an intermediate of a hexahydroquinolinedione compound. A compound represented by formula I undergoes a hydrolysis reaction shown in the description inthe presence of an acid to obtain the compound represent
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Paragraph 0054; 0062-0065
(2020/02/29)
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- Preparation method of 2-chloro-7, 8-dihydro-6H-quinolin-5-ketone
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The invention relates to a preparation method of 2-chloro-7, 8-dihydro-6H-quinolin-5-ketone. 2-chloro-7, 8-dihydro-6H-quinolin-5-ketone comprises preparation components of a component as shown in thedescription, anhydrous ethanol, anhydrous ammonium acetate, anhydrous sodium carbonate, methyl acrylate, DMF, acetonitrile, phosphorus oxychloride and ethyl acetate, and by adopting the preparation method, the existing situation of g-class production is overcome, so that the technical level reaches the industry leading position. Furthermore, the optimized process enables the order batch output ofa project to reach 15 kg, the product quality is improved obviously, the product purity reaches 99.5%, single impurities are lower than 0.1%, and heavy metal, burning residues and residual solvents meet the standards of pharmacopoeia. Technically, the process is optimized, therefore the overall yield of the process is increased by 30%, and the discharge of three wastes (waste water, waste gas andwaste residues) is reduced through the recovery of the solvents.
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Paragraph 0056; 0066-0072
(2018/07/30)
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- HETEROARYLCARBOXAMIDE DERIVATIVES AS PLASMA KALLIKREIN INHIBITORS
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The present invention relates to compounds of general formula I, wherein D1 to D3, A, R1, R2, Y and n are defined as in claim 1, which have valuable pharmacological properties, in particular are inhibitors of pl
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Page/Page column 65
(2017/05/21)
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- SUBSTITUTED TETRAHYDROQUINOLINONE COMPOUNDS AS ROR GAMMA MODULATORS
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The present invention provides substituted tetrahydroquinolinone and related compounds of formula (I), which are therapeutically useful as modulators of Retinoic acid receptor-related orphan receptors (RORs), more particularly as RORγ modulators. These co
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Page/Page column 52; 53
(2016/12/07)
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- Novel 5-aminotetrahydroquinoline-2-carboxylic acids and their use
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The present application relates to novel 5-amino-5,6,7,8-tetrahydroquinoline-2-carboxylic acids, to processes for their preparation, to their use for the treatment and/or prevention of diseases, and to their use for producing medicaments for the treatment and/or prevention of diseases, especially for the treatment and/or prevention of cardiovascular and cardiopulmonary disorders.
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Paragraph 0365; 0366; 0367
(2014/02/16)
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- Discovery of pyrrolidine-based β-secretase inhibitors: Lead advancement through conformational design for maintenance of ligand binding efficiency
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We have developed a novel series of pyrrolidine derived BACE-1 inhibitors. The potency of the weak initial lead structure was enhanced using library-based SAR methods. The series was then further advanced by rational design while maintaining a minimal ligand binding efficiency threshold. Ultimately, the co-crystal structure was obtained revealing that these inhibitors interacted with the enzyme in a unique fashion. In all, the potency of the series was enhanced by 4 orders of magnitude from the HTS lead with concomitant increases in physical properties needed for series advancement. The progression of these developments in a systematic fashion is described.
- Stachel, Shawn J.,Steele, Thomas G.,Petrocchi, Alessia,Haugabook, Sharie J.,McGaughey, Georgia,Katharine Holloway,Allison, Timothy,Munshi, Sanjeev,Zuck, Paul,Colussi, Dennis,Tugasheva, Katherine,Wolfe, Abigail,Graham, Samuel L.,Vacca, Joseph P.
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scheme or table
p. 240 - 244
(2012/03/10)
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- HETEROCYCLIC COMPOUNDS AND THEIR USE AS GLYCOGEN SYNTHASE KINASE-3 INHIBITORS
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The present invention relates to novel heterocyclic compounds which are useful for inhibiting glycogen synthase kinase 3 (GSK-3), methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.
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Page/Page column 75
(2012/04/05)
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- TRICYCLIC HETEROCYCLIC COMPOUNDS
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Disclosed are compounds of Formula (I) or stereoisomers or salts thereof, wherein: X1, X2, X3, W, Q1, Q2, and G2 are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.
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Page/Page column 206-207
(2011/06/16)
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- Heterodimers and Methods of Using Them
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Novel heterodimers of tetrahydroacridines and tetrahydroquinolinones are disclosed. The heterodimers are capable of acting as both acetylcholinesterase inhibitors and N-methyl-D-aspartate (NMDA) receptor antagonists. The heterodimers may be used to improve cognitive defects via treatment or prevention in both humans and non-humans.
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Page/Page column 11
(2008/12/07)
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- NOVEL NUCLEAR HORMONE RECEPTOR LIGANDS AND METHODS
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The present invention relates to compounds and derivatives thereof, their synthesis, and their use as nuclear hormone receptor modulators. The compounds of the instant invention are ligands for nuclear hormone receptors and as such may be useful for treat
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- A solution-phase procedure for the preparation of 4-azasteroid mimetics
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A Diels-Alder approach has been employed to make 3-oxo-octahydro-benzo[f] quinoline derivatives as ligands for nuclear hormone receptors and steroid biosynthetic enzymes. The five-step synthesis is a model for the synthesis of libraries on solid-phase.
- Ruda, Marcus C.,Bergman, Jan,Koehler, Konrad,Liu, Ye
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p. 571 - 574
(2007/10/03)
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- SYNTHESIS OF 5-METHOXY-2(1H)-QUINOLINONE
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Methylation of 5-hydroxy-2(1H)quinolinone (1) is studied.The previous protection of the amide group in 1 is proposed as the more convenient method to obtain 5-methoxy-2(1H)-quinolinone (1a).
- Fernandez, Maria,Cuesta, Elena de la,Avendano, Carmen
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p. 2615 - 2620
(2007/10/02)
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- SYNTHESIS OF 1,2,3,4-TETRAHYDROACRIDINE AND 5,6,7,8-TETRAHYDROQUINOLINE DERIVATIVES AS POTENTIAL ACETYLCHOLINESTERASE INHIBITORS
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This paper described the synthesis of 1,3,4,5-tetrahydropyrazoloacridine (2) and 11-amino-1,3,4,5-tetrahydroazepinoquinolin-2-one (3) obtained by Schmidt reaction of 9-amino-3,4-dihydroacridin-1(2H)-one (1) and the preparation of 4,5-dihydro-3H-isoxazoloacridine (7) obtained in the same manner starting from 3,4-dihydroacridine-1,9-(2H,10H)-dione (6).The corresponding pyrazoloquinoline (20) and isoxazoloquinoline (18) are also reported.The compounds have been prepared with the aim of studying their possible activity as acetylcholinesterase inhibitors.
- Gatta, Franco,Giudice, Maria Rosaria Del,Pomponi, Massimo,Marta, Maurizio
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p. 991 - 1004
(2007/10/02)
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- Pharmaceutical compositions containing quinolin-2,5-diones, new quinolin-2,5-diones and processes for the preparation thereof
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This invention relates to pharmaceutical compositions containing quinolin-2,5-diones of formula STR1 wherein A, B, R1 to R3 and X are defined hereinbelow, some of which are novel, which compounds have valuable pharmacological propert
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- ACETALES OF LACTAMS AND AMIDES. 60. N- AND O-ALKYLATION OF 5-OXO-5,6,7,8-TETRAHYDROCARBOSTYRILS. SYNTHESIS OF ISOXAZOLO- AND PYRAZOLOQUINOLINES
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The alkylation of 5-oxo-5,6,7,8-tetrahydrocarbostyrils has been examined by GLC.It has been found that, irrespective of the reaction conditions and the alkylating agent used, both N- and O-alkylation occur.When triethyloxonium fluoroborate and N,N-DMF diethyl acetal are used O-alkylation predominates, and with alkyl halides, N-alkylation.Reaction of N-ethyl-5-oxo-5,6,7,8-tetrahydrocarbostyril and 2-ethoxy-5-oxo-5,6,7,8-tetrahydroquinoline with DMF diethyl acetal gives the 6-dimethylaminomethylene derivatives, treatment of which with hydrazine hydrate or hydroxylamine affording isoxazolo- or pyrazoloquinolines.
- Shanazarov, A. K.,Kuzovkin, V. A.,Chistyakov, V. V.,Granik, V. G.
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- Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles.V. Synthesis of 5-Acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles and 1,2,5,6,7,8-Hexahydro-2,5-dioxo-3-quinolinecarboxamides
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The reaction of open-chain sym-2-dimethylaminomethylene-1,3-diones Ia-d with sodium cyanoacetamide gave, generally in good yields, 6-substituted 5-acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles IIa-d, whereas cyclohexane sym-2-dimethylaminomethylene-1,3-diones Ie-h afforded in general a mixture of 1,2,5,6,7,8-hexahydro-2,5-dioxo-3-quinolinecarbonitriles and 5,6,7,8-tetrahydro-2,5-dioxo-2H-1-benzopyran-3-carboxamides, the latter being isolated in two cases.The reaction of Ie-h with cyanoacetamide in refluxing anhydrous ethanol gave 1,2,5,6,7,8-hexahydro-2,5-dioxo-3-quinolinecarboxamides IIIe-h in excellent yields, whereas Ia-d did not react with the exception of Ia which afforded in good yield 3-pyridinecarboxamide IIIa.Other 3-pyridinecarboxamides were obtained by partial hydrolysis of nitriles IIb,d. 3-Pyridine and 3-quinoline carboxamides were hydrolyzed in satisfactory yields with hydrochloric acid to the corresponding carboxylic acids, which were decarboxylated in good yields to 5-acyl-2(1H)-pyridinones and 7,8-dihydro-2,5-(1H,6H)-quinolinediones, respectively, by reflux in quinoline containing a catalytic amount of copper powder.
- Mosti, Luisa,Schenone, Pietro,Menozzi, Giulia
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p. 1503 - 1509
(2007/10/02)
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