37926-75-3Relevant academic research and scientific papers
GLUCOCORTICOID RECEPTOR AGONIST AND IMMUNOCONJUGATES THEREOF
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Paragraph 0098-0099, (2021/08/20)
Provided herein are glucocorticoid receptor agonist immunoconjugates, glucocorticoid receptor agonists, pharmaceutical compositiosn including the same, and methods of using the same.
POTENT SOFT ANTI-INFLAMMATORY CORTICOSTEROID COMPOUNDS AND USES THEROF
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Paragraph 0070; 0079; 0080, (2019/01/08)
Potent soft corticosteroid pharmaceutical compositions comprising them and method for use as anti-inflammatory agents. Also, a method for softening fluticasone propionate and similar corticosteroids to arrive at potent but safer alternatives. The compound S-fluoromethyl 17α-dichloroacetoxy-6α,9α-difluoro-11β-hydroxy-16a- methyl-3-oxoandrosta-1,4-diene-17β-carbothioate, which is equally potent to but safer than fluticasone, is among those provided. Another compound of particular interest is 2-hydroxyethyl 17α-dichloroacetoxy-6α,9α-difluoro-11β-hydroxy-16β- methyl-3-oxoandrosta-1,4-diene-17β-carboxylate.
Mechanism of base-catalyzed autooxidation of corticosteroids containing 20-keto-21-hydroxyl side chain
Li, Min,Chen, Bin,Monteiro, Stephanie,Rustum, Abu M.
scheme or table, p. 4575 - 4581 (2009/10/11)
Corticosteroids and related compounds containing the 20-keto-21-hydroxyl side chain such as betamethasone, betamethasone 9,11-epoxide, dexamethasone, and dexamethasone 9,11-epoxide have been found to undergo facile autooxidation on the 1,3-dihydroxyaceton
Novel androstane-17β-carboxylic acid esters
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, (2008/06/13)
The invention refers to compounds having anti-inflammatory activity characterized by the formula STR1 or a stereoisomeric component thereof, in which formula X1 represents a hydrogen, chlorine, bromine or fluorine atom; X2 represents a hydrogen, chlorine, bromine or fluorine atom; R1 represents a β-hydroxy group, a β-chlorine atom or an oxo group; R2 represents a hydrogen atom, a methylene group or an α- or β-methyl group; R3 represents a hydrogen atom or an acyl group of 1 through 8 carbon atoms; R4 represents a hydrogen atom, a (C1 -C5) alkyl group or a phenyl group; R5 represents a hydrogen atom, a (C1 -C5) alkyl group or a phenyl group; Y represents either CR7 R8, O, S or NR9, where R7, R8 and R9 are selected from hydrogen or from straight or branched hydrocarbon chains having 1-8 carbon atoms or from a phenyl group. R6 represents a hydrogen; a methyl group; a phenyl or an alkenyl or cycloalkylene group optionally substituted by alkyl, nitro, carboxy, alkoxy, halogen, cyano, carbalkoxy and trifluoromethyl group(s); a (C1 -C5) alkyl group substituted by at least one halogen atom; a saturated or unsaturated carbocyclic or heterocyclic (O, S, N) ring system containing 3-10 atoms in the ring system; a C1 alkyl group substituted by either one or two alicyclic or aromatic 3,4,5 or 6-numbered ring system(s) or one, two or three straight or branched alkyl or alkenyl group(s) of 1 through 18 carbon atoms; and represents a single or double bond. The invention also refers to a process and intermediates for the preparation of these compounds, a pharmaceutical preparation containing one of the compounds and a method for the treatment of inflammatory conditions.
Thiol Esters from Steroid 17β-Carboxylic Acids: Carboxylate Activation and Internal Participation by 17α-Acylates
Kertesz, Denis J.,Marx, Michael
, p. 2315 - 2328 (2007/10/02)
The chemistry of the steroid 17β-carboxylic acids derived from 16,17α-disubstituted corticosteroids was investigated with respect to thiol ester formation.Major quantities of 17-spiro byproducts were observed in the reactions of 16-methyl-17α-acyloxy acids, and the degree of 17-ester participation leading to these structures was dependent on the carboxylate activating group used and stereochemistry at C-16.Diethyl phosphate mixed anhydrides of these acids reacted with mercaptide salts to give mixtures of thiol esters with 17-spiro acylthio ortho esters, which predominated and were particularly stable in the case of 16β-methyl substrates; in addition, considerable reversion of 16α-methyl phosphate intermediates to starting acid was experienced.The use of diphenyl chlorophosphate as the activating agent greatly improved yields of thiol esters.Methanolysis of the phosphate adducts derived from 17α-acyloxy acids gave 17-spiro acyl ortho esters as the exclusive products.The reactions of 17α-acetoxy acids with 2-fluoro-N-methylpyridinium tosylate (FMPT) gave novel 17-spiro acyl fluoro ketals 32-35, whereas similar treatment of 17-hydroxy acids led to products of dehydration or of 18-methyl migration, including the novel 13,17-β-lactones 39 and 41.Activation with carbonyldiimidazole followed by addition of mercaptans allowed the preparation of thiol ester products from 17-hydroxy acids, but the method was restricted to use with these substrates.Neighbouring-group participation was not possible for the 16,17-acetonide acid 10, and activation with either cllorophosphate diesters or FMPT followed by reaction with methanethiolate gave high yields of methylthio ester 17.
