- LIPOXYGENASE INHIBITORS
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Various embodiments of the present disclosure are directed to compounds having Formula (I), Formula (IA), Formula (IB), Formula (IC), Formula (ID), Formula (IE), and/or pharmaceutically acceptable salts thereof. The compounds can be suitable for inhibiting lipoxygenases, and/or treating associated diseases, such as Alzheimer's disease. In some embodiments, the compounds may be administered to a patient as part of a pharmaceutical formulation.
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- Synthesis method for (R)-3-amino-1,2,3,4-tetrahydrocarbazole
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The invention discloses a synthesis method for a Ramatroban intermediate (R)-3-amino-1,2,3,4-tetrahydrocarbazole.The synthesis method includes the steps that 1,4-cyclohexanedione monoethylene acetal and phenylhydrazine are subjected to aldehyde ketone amine condensation, then cyclization is conducted to obtain 3,3-vinyl dioxo-1,2,4,9-tetrahydrocarbazole-3-ketone, then protecting groups are removed to obtain 1,2,4,9-tetrahydrocarbazole-3-ketone, 1,2,4,9-tetrahydrocarbazole-3-ketone and O-hydroxylamine hydrochloride react to obtain oxime ether, and oxime ether is subjected to low-temperature chiral selective reduction to directly obtain (R)-3-amino-1,2,3,4-tetrahydrocarbazole.A new synthesis route of the important intermediate (R)-3-amino-1,2,3,4-tetrahydrocarbazole of medicine Ramatroban is provided.The synthesis method is simple and convenient, operation conditions are mild, the reaction yield is high, an amplification reaction can be conducted, and the synthesis method is applied to industrial production.
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- HETEROARYL COMPOUNDS FOR KINASE INHIBITION
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Compounds and pharmaceutical compositions that modulate kinase activity, including mutant EGFR and mutant HER2 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including mutant EGFRand mutant HER2 activity, are described herein.
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Paragraph 00409
(2016/12/01)
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- Metal-free, mild, nonepimerizing, chemo- and enantio- or diastereoselective N-alkylation of amines by alcohols via oxidation/imine-iminium formation/reductive amination: A pragmatic synthesis of octahydropyrazinopyridoindoles and higher ring analogues
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A mild step and atom-economical nonepimerizing chemo- and enantioselective N-alkylating procedure has been developed via oxidation/imine-iminium formation/reduction cascade using TEMPO-BAIB-HEH-Bronsted acid catalysis in DMPU as solvent and a stoichiometric amount of amine. The optimized conditions were further extended for the nonenzymatic kinetic resolution of the chiral amine thus formed under nonenzymatic in situ hydrogen-transfer conditions using VAPOL-derived phosphoric acid (VAPOL-PA) as the Bronsted acid catalyst. The enantioselective cascade of the presented reaction was successfully utilized in the synthesis of octahydropyrazinopyridoindole and its higher ring analogues.
- Khan, Imran A.,Saxena, Anil K.
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p. 11656 - 11669
(2014/01/06)
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- Asymmetric chemoenzymatic synthesis of ramatroban using lipases and oxidoreductases
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A chemoenzymatic asymmetric route for the preparation of enantiopure (R)-ramatroban has been developed for the first time. The action of lipases and oxidoreductases has been independently studied, and both were found as excellent biocatalysts for the production of adequate chiral intermediates under very mild reaction conditions. CAL-B efficiently catalyzed the resolution of (±)-2,3,4,9-tetrahydro-1H-carbazol-3-ol that was acylated with high stereocontrol. On the other hand, ADH-A mediated bioreduction of 4,9-dihydro-1H-carbazol-3(2H)-one provided an alternative access to the same enantiopure alcohol previously obtained through lipase-catalyzed resolution, a useful synthetic building block in the synthesis of ramatroban. Inversion of the absolute configuration of (S)-2,3,4,9-tetrahydro-1H-carbazol-3-ol has been identified as a key point in the synthetic route, optimizing this process to avoid racemization of the azide intermediate, finally yielding (R)-ramatroban in enantiopure form by the formation of the corresponding amine and the convenient functionalization of both exocyclic and indole nitrogen atoms.
- Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
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p. 4842 - 4848
(2012/07/31)
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- TRICYCLIC CYTOPROTECTIVE COMPOUNDS
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Compounds of formula (I): in which: X is a group of formula >CR1R2 or >SO2; Y is a group of formula >NH or >CR1R2; Z is a group of formula >C=O or >CH2 or a direct bond; R1 hydrogen and R2 is hydrogen, carboxy or hydroxy; or R1 and R2 together represent an oxo group, a methylenedioxy group or a hydroxyimino group; R3 is hydrogen or lower alkyl; R4 represents two hydrogen atoms, or an oxo or hydroxyimino group; R5 is hydrogen, lower alkyl or halogen; R6 is hydrogen, lower alkoxy or carboxy; R7 and R8 are each hydrogen, lower alkyl or halogen; and pharmaceutically acceptable salts and esters thereof can be used for the treatment or prophylaxis of acute or chronic neurodegenerative diseases or conditions such as Alzheimer’s Disease, Parkinson’s Disease, Huntington’s Chorea, Multiple Sclerosis or the sequelae to acute ischaemic events such as heart attack, stroke or head injury and for protection against ischaemic damage to tissues of peripheral organs.
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Page/Page column 19
(2008/06/13)
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- Tetrahydrocarbazol derivatives as ligands for G-protein-coupled receptors (GPCR)
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This invention provides new tetrahydrocarbazole derivatives that act as ligands for G-protein-coupled receptors (GPCR), especially as antagonists of the gonadotropin-releasing hormone (GnRH). A pharmaceutical composition that contains these new tetrahydro
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- Synthesis of aspidospermidine alkaloids from 1,2,3,4- tetrahydrocarbazole: Total stereoselective synthesis of (±)-18- noraspidospermidine
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The reactivity of the 1,2,3,4-tetraliydrocarbazol-4-one derivatives has been analysed and applied to the synthesis of (±)-18-noraspidospennidine (1b). Tiffs was synthesised, starting from 4-(1',3'-dioxolan-2'- yl)cyclohexanone which was successively trans
- Urrutia, Anahi,Rodriguez, J. Gonzalo
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p. 11095 - 11108
(2007/10/03)
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- Studies in the Synthesis of Brevianamides A and B: Pilot Investigations and the Preparation of 1,1-Dimethyl-1,2,4,9-tetrahydrocarbazol-3-one
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In preliminary investigations directed ultimately at the synthesis of the indoxyl mould metabolites, brevianamides A and B, routes to the synthesis of 4,4-dimethyl-1,3,4,9-tetrahydrocarbazol-2-one and 1,1-dimethyl-1,2,4,9-tetrahydrocarbazol-3-one have bee
- Ritchie, Robert,Saxton, J. Edwin
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p. 528 - 545
(2007/10/02)
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- Cycloalkyl-one-containing benzenesulphonamides
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Cycloalkanol[1,2-b]indole-sulphonamides of the formula STR1 where appropriate in an isomeric form, and their salts are disclosed. These compounds are useful to inhibit platelet aggregation and to antagonize thromboxane A2.
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- The Reactions of Some Tetrahydro-β-Carbolines, of Hexahydroazepinoindoles, and of Tetrahydrocarbazolones with Arenesulphonyl Azides
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2,9-Dimethyl-1,2,3,4-tetrahydro-1-oxo-β-carboline and 2,9-dimethyl-1,2,3,4-tetrahydro-β-carboline react with arenesulphonyl azides forming indoline-3-spiropyrrolidines; 2,10-dimethyl-3,4,5,10-tetrahydroazepinoindol-1(2H)-0ne and 2,10-dimethyl-1,2,3
- Bailey, A. Sydney,Vandrevala, Marazban H.
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p. 1512 - 1515
(2007/10/02)
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