51372-28-2

Usage

Uses

Used in Pharmaceutical Industry:
(S)-16alpha,17-(butylidenedioxy)-11beta,21-dihydroxypregna-1,4-diene-3,20-dione is used as an active pharmaceutical ingredient for the treatment of various inflammatory conditions. Its anti-inflammatory properties make it effective in managing asthma, allergic rhinitis, and other respiratory disorders. It is also used for the treatment of certain gastrointestinal conditions, such as Crohn's disease and ulcerative colitis.
Brand names:
(S)-16alpha,17-(butylidenedioxy)-11beta,21-dihydroxypregna-1,4-diene-3,20-dione is marketed under various brand names, including Entocort (AstraZeneca), Pulmicort (AstraZeneca), and Rhinocort (AstraZeneca), which are used in different formulations and dosages to cater to the specific needs of patients with various conditions.

Upstream product

• 51372-29-3 budesonide 
• 13951-70-7 desonide 
• 123-72-8 butyraldehyde 
• 86401-80-1 11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate 
• 91160-89-3 9α-bromo-11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate 
• 77017-20-0 16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate 
• 37413-91-5 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 

Relevant academic research and scientific papers

STEROIDS AND PROTEIN-CONJUGATES THEREOF

Described herein protein steroid conjugates that are useful, for example, for the target-specific delivery of glucocorticoids (GCs) to cells.

Pregnane derivatives 16, 17 - acetal (ketone) preparation method

Disclosed is a method for preparing a pregnane derivative 16,17-acetal (ketal) compound shown in the general formula I, the method comprising the step of reacting a compound of a general formula II with a compound of a general formula III or a general formula IV in the presence of boron trifluoride, wherein the dotted line between site 1 and site 2 denotes a saturated or unsaturated bond; R is hydroxyl, halogen or -OCOR7, wherein R7 is a C1-C12 linear chain or branched alkyl, a C3-C10 cycloalkyl, a C2-C8 alkenyl or a C2-C8 alkynyl; R1 and R2 are each hydrogen, a C1-C12 linear chain or branched alkyl, a C3-C10 cycloalkyl, a C2-C8 alkenyl or a C2-C8 alkynyl, or R1, R2 and the carbon to which they are connected form a C3-C10 cycloalkyl together, with the provision that R1 and R2 are not hydrogen simultaneously; R3 is hydrogen or -OCOR8, wherein R8 is a C1-C12 linear chain or branched alkyl, or a C3-C10 cycloalkyl; R4 is hydrogen, fluorine or chlorine; R5 is hydrogen, fluorine, chlorine or methyl; and R6 is a C1-C12 linear chain or branched alkyl. Compared with current processes, the method causes little pollution to the environment, has relatively mild reaction conditions, ease of control, reduced energy consumption and low production costs.

NOVEL PROCESS FOR PREPARATION OF GLUCOCORTICOID STEROIDS

The present invention discloses a process for the preparation of 16, 17-acetals of pregnane derivatives having formula (I) wherein each substituent is independently selected from; R1 is H or CH3; R2 is C1-C6 linear or branched alkyl, alkynyl group or cycloalkyl group; aryl or heteroaryl group; or R1 and R2 combine to form saturated, unsaturated C3-C6 cyclic or heterocyclic ring; R3 and R4 are same or different and each independently represents H or halogen; R5 is -OH or –OCOR wherein R represents H or C1-C6 linear, branched or cyclic alkyl group that may be substituted.

Azo-reductase activated budesodine prodrugs for colon targeting

Budesodine is a synthetic glurocorticoid that undergoes substantial first pass metabolism, limiting systemic exposure. Its use in treatment of inflammatory bowel disease would benefit from a targeting strategy that could lead to a local topical effect, improving safety and increasing anti-inflammatory efficacy. A two-step prodrug strategy involving azoreduction/cyclization that we developed previously for prednisolone is here applied with some variations to budesonide. The budesodine prodrugs were tested using an in vitro azoreductase assay simulating human colonic microflora. The kinetics of amino steroid ester cyclization and its pH dependence was also evaluated. The stability of the prodrugs systems in simulated human duodenal and gastric fluid was evaluated to determine the likelihood of intact intestinal transit. The propionic acid derived prodrug 3 undergoes rapid activation by Clostridium perfingens and its putative reduction product cyclizes with acceptable rapidity when synthesized independently. These properties of 3 suggest that it has potential in management of ulcerative colitis.

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.

Preparative separation of steroids by reverse phase HPLC

Budesonide C22R epimer is more active than C22S epimer. In so far the preparative separation of the two molecules from the mixture has not been made suitable at industrial level. The present invention describes the procedure to separate at preparative scale the epimers of certain synthetic steroid mixture. The present invention has based on isocratic reverse phase HPLC method and some devices as the procedure to dissolve the mixture and load it on the column, the choice of solvent and the physic-chemical condition of the chromatography, the recovery of the solvents. The whole of these devices to make the process to separate epimers from steroid mixtures, practicable at industrial level. More in particular the present invention describes the separation of the (22 R, S) 16α,17α-butyldenedioxy-11β, 21-dihydroxypregna-1,4-diene-3,20-dione (Budesonide), at preparative scale, into C22R and C22S epimers. The Budesonide has dissolved in a some organic solvent and each epimer has eluted in a water solution, permitting a highly easily recovery of the molecules also useful to pharmaceutical formulations.