51372-29-3

Usage

Uses

Used in Pharmaceutical Industry:
16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione is used as a pharmaceutical compound for its potential therapeutic applications. 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione's unique structure and functional groups may allow it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Steroid Research:
In the field of steroid research, 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione can be used as a starting material or a reference compound for the synthesis and evaluation of novel steroidal compounds. Its structural features may provide insights into the design and optimization of new steroids with improved pharmacological properties.
Used in Drug Delivery Systems:
Similar to gallotannin, 16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione may also be employed in the development of drug delivery systems. Its unique structural features could be utilized to improve the solubility, stability, and bioavailability of other drugs, potentially enhancing their therapeutic efficacy.
Used in Budesonide (B689490) Epimer R:
16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione is used as a key intermediate in the synthesis of Budesonide (B689490) epimer R. Budesonide is a glucocorticoid with anti-inflammatory properties, used in the treatment of various inflammatory conditions, such as asthma and allergies.
Used in Labelled Triamcinolone:
16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione can also be used in the preparation of labelled Triamcinolone, a glucocorticoid with antiasthmatic and antiallergic properties. Labelled Triamcinolone can be employed in research and diagnostic applications, such as tracking the distribution and metabolism of the drug in the body.
Chemical Properties:
16a(R),17-(Butylidenebis(oxy))-11b,21-dihydroxypregna-1,4-diene-3,20-dione is a light beige solid, indicating its stability and suitability for various pharmaceutical applications. Its solid-state properties may also influence its formulation and delivery in drug development.

InChI:InChI=1/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21+,22+,23-,24-,25+/m0/s1

Upstream product

• 13951-70-7 desonide 
• 123-72-8 butyraldehyde 
• 638-94-8 desonide 
• 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 
• 77017-20-0 16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate 
• 91160-89-3 9α-bromo-11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate 
• 64945-47-7 21-acetoxy-17α-hydroxy-11β-trifluoroacetoxy-1,4-pregnadiene-3,20-dione 
• 52-21-1 prednisolone 21-acetate 
• 51333-05-2 2-((6aR,6bS,7S,8aS,8bS,11aR,12aS,12bS)-7-hydroxy-6a,8a-dimethyl-4-oxo-10-propyl-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl acetate 

Downstream Products

• 51372-28-2 (22S)-Budesonide 

Relevant academic research and scientific papers

Preparation method of budesonide

The invention discloses a preparation method of budesonide, and belongs to the technical field of preparation and processing of medicines. According to the method, prednisolone acetate is used as an initial raw material, and is subjected to five steps of protection, dehydration, dihydroxy, hydrolysis and condensation to prepare the budesonide. According to the preparation method, the reaction process can be effectively shortened by improving the defects of a traditional process, reaction conditions are mild, osmium tetroxide which is high in toxicity and not environmentally friendly is avoided, environmental pollution is reduced, and the method is high in overall conversion rate, easy and convenient to operate, suitable for industrial production and wide in market prospect.

A budesonide industrial preparation method (by machine translation)

The invention relates to a cloth budesonide industrial preparation method. Specifically, the invention relates to a hydrochloric acid aqueous solution, dichloromethane and in acetonitrile, 16 α - hydroxy prednisolone with butyraldehyde by the reaction of the budesonide. In the method of the present invention has the industrial can be implemented on, repeatability and the like. (by machine translation)

INDUSTRIAL ECOLOGICAL PROCESS OF MANUFACTURING OF BUDESONIDE

Disclosed herein is an improved process for the preparation of Budesonide using Perchloric acid catalyst in water as a major medium.

A preparation method of budesonide

The invention discloses a budesonide preparing method. Prednisone I and acetic anhydride II react to produce 17,21-diacetoxy-1,4-pregnane diene-3,11,20-triketone III, the III is degreased in an anhydrous solvent to obtain 21-acetoxyl group-1,4,16-pregnane diene-3,11,20-triketone IV, the IV is oxidized to obtain 16alpha,17alpha-dyhydroxy-21-acetoxyl-1,4-pregnane diene-3,11,20-triketone V, the V and n-butyl aldehyde VI are condensed to obtain 16alpha,17alpha-22(R,S) propyl methylenedioxy-21-acetoxyl group-1,4-pregnane diene-3,11,20-triketone VII, the VII is reduced to obtain 16alpha,17alpha-22(R,S) propyl methylenedioxy-11beta-hydroxyl-21-acetoxyl group-1,4-pregnane diene-3,20-diketone VIII, the VIII is subjected to base catalysis to obtain budesonide IX. The budesonide preparing method is suitable for industrial production.

The preparation method of the budesonide

The invention discloses a preparation method of budesonide. The preparation method comprises the following steps: (1) carrying out n-butyraldehyde aldolization for 16 alpha-hydroxyl prednisolone acetate as shown in formula (1) to obtain a budesonide crude prodct; (2) then hydrolyzing 21-acetates; and (3) collecting the product budesonide from reactant. By adopting the preparation method, the unstable midbody 16 alpha-hydroxyl prednisolone is avoided. The preparation method is easy to operate and control, and the total yield of the budesonide is greatly increased. The reaction formula is shown in the specification.

PROCESS FOR PREPARING BUDESONIDE

A process is described for preparing budesonide which comprises the steps of: a) preparing an aqueous hydrochloric acid solution; b) reacting 16α-hydroxyprednisolone and butyraldehyde within the solution prepared in step a), in an inert atmosphere; c) quenching the reaction of step b) with water. The process of the invention enables the ratio between the A and B epimers of budesonide to be controlled.

ACETALIZATION PROCESS FOR PREPARATION OF STEROID COMPOUNDS

The present invention provides acetalization process for preparation of 16,17-acetals of pregnane derivatives from corresponding 16,17-dihydroxy compounds in phosphoric acid.

A mild method of deprotection of corticosteroidal esters

The effect of microwave radiation and ultrasounds on the reaction of transesterification of corticosteroidal esters were investigated.