910-99-6Relevant academic research and scientific papers
Preparation method of betamethasone epoxide
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Paragraph 0098; 0099; 0115; 0116; 0122; 0123; 0129; 0130, (2020/12/15)
The invention provides a preparation method of a betamethasone epoxide, which comprises the steps of step 1, preparing a first reaction solution containing a compound II by using a compound I based onan esterification reaction; step 2, based on a bromine hydroxylation reaction, preparing a second reaction solution containing a compound III by using the first reaction solution; and 3, based on a hydrolysis reaction, preparing a betamethasone epoxide IV crude product by using the second reaction solution. The betamethasone epoxide IV is synthesized from the compound I by adopting a one-pot method, the method has the advantages of high yield, simplicity and safety in operation, low cost, small pollution and the like, and the method is stable and easy to realize industrial production.
Non-hormonal steroid modulators of NF-κβ for treatment of disease
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Page/Page column 43-44, (2019/11/18)
The present invention relates to compounds and methods which may be useful as treatments of diseases.
Betamethasone intermediates or its preparation method of the analogue
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, (2016/12/22)
The invention relates to a preparation method of a steroid hormone medicinal intermediate, in particular to a preparation method for a betamethasone intermediate or its analogue. The betamethasone intermediate or its analogue is prepared from a compound I by means of elimination reaction, methylation reaction, cyano-group substitution reaction, siloxy protective reaction, intramolecular nucleophilic substitution reaction and esterification reaction. The method provided by the invention has the characteristics of cheap raw materials, and high and stable yield. The reaction route is as the following, wherein R1 is Cl or Br, and R is H or hydrocarbonyl of C1-C10.
NON-HORMONAL STEROID MODULATORS OF NF-KAPPA BETA FOR TREATMENT OF DISEASE
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Paragraph 0240-0242, (2017/01/19)
The present invention relates to compounds and methods which may be useful as treatments of diseases.
NON-HORMONAL STEROID MODULATORS OF NF-KB FOR TREATMENT OF DISEASE
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Paragraph 0165; 0166, (2015/09/23)
The present invention relates to compounds and methods which may be useful as treatments of neuromuscular diseases such as muscular dystrophy, and as inhibitors of NF-κB for the treatment or prevention of muscular wasting disease, including muscular dystrophy.
VBP15: Preclinical characterization of a novel anti-inflammatory delta 9,11 steroid
Reeves, Erica K.M.,Hoffman, Eric P.,Nagaraju, Kanneboyina,Damsker, Jesse M.,McCall, John M.
, p. 2241 - 2249 (2013/05/22)
Δ9,11 modifications of glucocorticoids (21-aminosteroids) have been developed as drugs for protection against cell damage (lipid peroxidation; lazaroids) and inhibition of neovascularization (anecortave). Part of the rationale for developing these compounds has been the loss of glucocorticoid receptor binding due to the Δ9,11 modification, thus avoiding many immunosuppressive activities and deleterious side effect profiles associated with binding to glucocorticoid and mineralocorticoid receptors. We recently demonstrated that anecortave acetate and its 21-hydroxy analog (VBP1) do, in fact, show glucocorticoid and mineralocorticoid receptor binding activities, with potent translocation of the glucocorticoid receptor to the cell nucleus. We concluded that Δ9,11 steroids showed novel anti-inflammatory properties, retaining NF-κB inhibition, but losing deleterious glucocorticoid side effect profiles. Evidence for this was developed in pre-clinical trials of chronic muscle inflammation. Here, we describe a drug development program aimed at optimizing the Δ9,11 chemistry. Twenty Δ9,11 derivatives were tested in in vitro screens for NF-κB inhibition and GR translocation to the nucleus, and low cell toxicity. VBP15 was selected as the lead compound due to potent NF-κB inhibition and GR translocation similar to prednisone and dexamethasone, lack of transactivation properties, and good bioavailability. Phamacokinetics were similar to traditional glucocorticoid drugs with terminal half-life of 0.35 h (mice), 0.58 h (rats), 5.42 h (dogs), and bioavailability of 74.5% (mice), and 53.2% (dogs). Metabolic stability showed ≥80% remaining at 1 h of VBP6 and VBP15 in human, dog, and monkey liver microsomes. Solubility, permeability and plasma protein binding were within acceptable limits. VBP15 moderately induced CYP3A4 across the three human hepatocyte donors (24-42%), similar to other steroids. VBP15 is currently under development for treatment of Duchenne muscular dystrophy.
NON-HORMONAL STEROID MODULATORS OF NF-KB FOR TREATMENT OF DISEASE
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Paragraph 0207, (2013/06/27)
The present invention relates to compounds and methods which may be useful as treatments of diseases.
A CONVENIENT ACCESS TO 16-METHYLENE AND 16β-METHYL CORTICOSTEROIDS BY A NOVEL TRANSFORMATION OF GEMINAL BIS(PHENYLSULPHINYL) INTERMEDIATES
Boivin, Jean,Chauvet, Christine,Zard, Samir Z.
, p. 4913 - 4916 (2007/10/02)
16α-Bis(phenylsulphinyl) methyl pregnane derivative 7 gives, by a series of eliminations and rearrangements, the corresponding 16-methylene intermediate 4 on heating in the presence of triphenylphosphine.Regio- and stereoselective hydrogenation of the latter using Wilkinson's catalyst furnishes 16β-methyl corticosteroid 5.
A Corticoid Synthesis from 9α-Hydroxyandrost-4-ene-3,17-dione via a Steroidal Oxazoline
Carruthers, Nicholas I.,Andrews, David R.,Garshasb, Sohaila,Giusto, Robert A.
, p. 1195 - 1196 (2007/10/02)
The synthesis of 21-acetoxy-17α-hydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione from 9α-hydroxyandrost-4-ene-3,17-dione via a 17-cyanohydrin and a 17-oxazoline is described.
17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one
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, (2008/06/13)
The invention is the compound 17β-cyano-9α, 17α-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17α-halo silyl ethers (II).
