- A Short and Efficient Synthetic Method for the Corticosteroid Side-Chain from 17-Keto Steroids
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21-Acyloxy-16(17)-ene-20-keto steroids were synthesized from 17-keto steroids in 4 steps using palladium(II)-catalyzed oxidative rearrangement of propargyl esters as a key reaction.
- Kataoka, Hideaki,Watanabe, Kiyoshi,Miyazaki, Ken-ichi,Tahara, Shin-ichiro,Ogu, Ken-ichi,et al.
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- A method for synthesis of alkyne progesterone
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The invention discloses a synthesis method of ethisterone which is prepared by adopting 4AD namely soybean oil tailings as a raw material, carrying out etherification protection as well as two-step reaction, namely, ethynylation and hydrolysis, and then refining. According to the invention, the raw material is replaced, that is the industrial tailing fermentation product 4AD of the soybean oil is used to replace diene; the raw material is wide in supply, low in cost and little in pollution; the reaction route is short; the process is simple; the auxiliary materials are commonly used chemical products; the generation amount of waste gas, waste water and waste solid is small and is a quarter of that generated in the traditional process.
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Paragraph 0025; 0037-0040; 0043-0046
(2017/12/28)
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- Method for preparing 17alpha-hydroxyprogesterone
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The invention discloses a method for preparing 17alpha-hydroxyprogesterone. According to the method, 4-androstenedione I serves as the raw material, a 17-site branched chain is introduced through ethynylation reaction, a 17-site beta-hydroxyl group is converted into an alpha-hydroxyl group through catalytic reaction, and finally 17alpha-hydroxyprogesterone is prepared through carbonylation reaction. The reaction formula is shown in the description. Four steps of reaction are conducted with 4-androstenedione as the raw material, a 17-site side chain is introduced through ethynylation reaction, the 17beta-hydroxyl group is converted into the 17alpha-hydroxyl group through transposition reaction, the weight yield of each step ranges from 85% to 109%, the total weigh yield is 85% or above, use of virulent acetone cyanohydrin is avoided, the raw material conversion rate is high, selectivity is good, production cost of 17alpha-hydroxyprogesterone is reduced, the process is safe, and large-scale industrial production is easy.
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Paragraph 0028; 0030
(2017/08/27)
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- Process for the preparation of danazol
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The invention discloses preparation methods of danazol and an intermediate thereof. The preparation method of danazol is prepared by the steps of taking androstenedione as a starting raw material, and carrying out 3-site enol etherification, 17-site carbonyl ethinylation, 3-site hydrolysis, 2-site methylidynel hydroxylation and oximation to obtain danazol. The 3-site enol etherification comprises firstly carrying out a reaction of androstenedione and triethyl orthoformate for 4-10 h in the presence of absolute ethyl alcohol and p-toluenesulfonic acid and at the temperature of 30-50 DEG C, then adding triethylamine at the temperature of 0-10 DEG C, and continuing to carry out a reaction for 0.2-1 h; the 17-site carbonyl ethinylation comprises firstly carrying out a reaction of a potassium hydroxide powder for 1-2 h in an acetylene airflow and at the temperature of 5-10 DEG C, and then carrying out a reaction with the 3-site enol etherified product for 2-4 h in the presence of tetrahydrofuran and a catalyst, at the temperature of 15-30 DEG C and in the acetylene airflow. The 3-site enol etherification is mild in reaction conditions and relatively high in yield, and the 17-site carbonyl ethynylation is relatively high in reaction yield and relatively short in time.
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- 17β-ethynylsteroids and process for preparing same
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This is disclosed novel intermediates, i.e. 17β-ethynylsteroids, which are useful for the preparation of corticoids such as hydrocortisone and prednisolone, and a process for preparing the same.
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- Process for preparing 17α-hydroxy-pregn-4-en-3,20-dione derivatives
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The invention relates to a novel process for the preparation of pregnane derivatives of formula I, STR1 wherein R1 stands for a methyl or an ethyl group, R2 represents a hydrogen atom or a methyl group, and X is a hydrogen atom or a formyl or acetyl group, and the bond indicated by a dotted and a continuous line stands for a single or a double bond between the two neighboring carbon atoms. According to the invention a trifluoroacetate ester of formula II, STR2 wherein R1 and R2 are as defined above, is reacted with formic acid or acetic acid in the presence of a catalytic amount of a mercury salt in a dipolar proton-free or basic solvent. The formyl or acetyl group being in the place of X can be split off in a way known per se. The process provides a novel advantageous method for building up the pregnane side chain characteristic of corticoids.
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- Water-soluble steroid compounds
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Beta-cyclodextrin forms a water-soluble complex or inclusion compound with steroid compounds having a molecular structure smaller than the interior cavity in the doughnut-shaped molecular structure of beta-cyclodextrin. The resulting inclusion compounds can be used for a variety of applications including aqueous topical ophthalmic preparations and topical dermatological ointments.
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- Process for the preparation of 17β-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone
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A new process for the preparation of 17β-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone is described herein. The process makes use of androst-4-ene-3,17-dione as the starting material and 17α-ethynyl-17β-hydroxyandrost-4-en-3-one as an early intermediate.
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- Process for the preparation of 17α-hydroxyprogesterones and corticoids from androstenes
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This invention discloses a general process for the production of corticoids from androstenes. This invention provides an economically viable alternative synthesis of 17α-hydroxyprogesterones and the corticoids.
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