13504-15-9

Usage

Uses

Used in Pharmaceutical Industry:
17,21-Dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione is used as an anti-inflammatory and immunosuppressive agent for the treatment of various conditions characterized by excessive inflammation or immune system overactivity. Its application in this industry is primarily due to its ability to suppress the immune response and reduce inflammation, providing relief to patients suffering from a wide array of disorders.
Used in Allergy Treatment:
In the field of allergy treatment, 17,21-dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione is utilized as a medication to alleviate symptoms associated with allergic reactions. Its anti-inflammatory and immunosuppressive properties help in reducing the severity and frequency of allergic responses, offering relief to patients with conditions such as asthma, rhinitis, and dermatitis.
Used in Dermatology:
17,21-Dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione is employed as a therapeutic agent in dermatology for the management of various skin conditions. Its potent anti-inflammatory effects make it suitable for treating skin disorders such as eczema, psoriasis, and contact dermatitis, promoting skin healing and reducing inflammation.
Used in Rheumatology:
In rheumatology, 17,21-dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione is used as a medication to treat inflammatory joint diseases, such as rheumatoid arthritis and lupus. Its ability to suppress the immune system and reduce inflammation helps in managing pain, swelling, and joint damage associated with these conditions.
Used in Respiratory Medicine:
17,21-Dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione is utilized in respiratory medicine for the treatment of breathing problems, including severe asthma and chronic obstructive pulmonary disease (COPD). Its anti-inflammatory properties help in reducing airway inflammation and improving lung function in patients with these respiratory disorders.
Used in Oncology:
In the field of oncology, 17,21-dihydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione is used as a medication to manage certain types of cancer, particularly those that are sensitive to corticosteroid therapy. Its immunosuppressive effects can help in controlling the growth and spread of cancer cells, as well as alleviating symptoms associated with cancer and its treatment.

Upstream product

• 37413-91-5 2-((10S,13S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 910-99-6 2-((10S,13S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 39780-55-7 17α,21-dihydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione 21-benzoate 
• 85650-69-7 C₂₆H₃₆O₉S 
• 56665-79-3 17α-hydroxy-16β-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione 

Relevant academic research and scientific papers

Non-hormonal steroid modulators of NF-κβ for treatment of disease

The present invention relates to compounds and methods which may be useful as treatments of diseases.

VBP15: Preclinical characterization of a novel anti-inflammatory delta 9,11 steroid

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

The present invention relates to compounds and methods which may be useful as treatments of diseases.

Process improvements in the synthesis of corticosteroid 9,11β-epoxides

Corticosteroid 9,11β-epoxides are key intermediates in the preparation of pharmaceutically important compounds such as betamethasone, mometasone, beclomethasone, and dexamethasone. A new process for the 9,11β-epoxide was developed using a PCl5-mediated regioselective dehydration of 11α-hydroxy-steroid to form the corresponding Δ9,11 double bond. The olefin is then converted into 9α,11β-bromoformate by treatment with 1,3-dibromo-5, 5-dimethyl hydantoin (DBH) in DMF and subsequently cyclized to produce the desired 9,11β-epoxide upon treatment with NaOH. Major process-related impurities such as 21-OH-Δ9,11-triene, 21-OH-Δ11,12-triene, 21-Cl-Δ9,11-triene, and β-epoxide-21-cathylate as well as 11β-Cl are all eliminated or minimized. This new process has been implemented in our manufacturing facility in full-scale production and proved to raise the overall yield and the quality of the product dramatically compared to the existing process.

Catalytic Epoxidation of Alkenes with Oxone

A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed.The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group.Optimal epoxidation conditions employ 10 mol percent of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant.Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables.A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96percent yield.

Process and intermediates for the preparation of 17 alphahydroxyprogesterones and corticoids from an enol steroid

This invention discloses an improved process for the production of corticoids from 17α-hydroxy steroids utilizing peroxymonosulfate.

9β,11β-Epoxy-5β-corticoids

17α-Acyloxy-5α-pregnanes (I) and 17α-acyloxy-5α-pregnanes (IV) have an excellent activity split providing high topical anti-inflammatory activity with very low systemic side effects.

17α-Acyloxy-5β-corticoids

17α-Acyloxy-5β-pregnanes (I) and 17α-acyloxy-5α-pregnanes (IV) have an excellent activity split providing high topical antiinflammatory activity with very low systemic side effects.