91934-95-1

Usage

Uses

Used in Pharmaceutical Industry:
(5α,11β,17α)-11-[4-(diMethylaMino)phenyl]-5,17-dihydroxy-19-norpregn-9-en-20-yn-3-one Cyclic 1,2-Ethanediyl Acetal is used as an intermediate in the synthesis of 17β-side chain mifepristone analogues. These analogues act as progesterone receptor antagonists, which have potential applications in the development of contraceptives and treatments for hormone-dependent disorders.
As a key intermediate in the synthesis of mifepristone analogues, (5α,11β,17α)-11-[4-(diMethylaMino)phenyl]-5,17-dihydroxy-19-norpregn-9-en-20-yn-3-one Cyclic 1,2-Ethanediyl Acetal contributes to the advancement of pharmaceutical research and the development of new therapeutic agents. Its unique structure and functional groups enable the design and synthesis of novel compounds with improved pharmacological properties and therapeutic potential.

Upstream product

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 137532-55-9 3-(ethylenedioxy)estra-5α,10α-epoxy-17α-ethynyl-17β-hydroxy-9(11)-ene 
• 39931-88-9 (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one 
• 5571-36-8 ethylene deltenone 
• 5173-46-6 4,9-Androstadiene-3,17-dione 
• 5490-76-6 (8S,13S,14S,17R)-17-ethynyl-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2’-[1,3]dioxolan]-17-ol 
• 786698-67-7 3-(ethylenedioxy)estra-5,10-epoxy-9⁽¹¹⁾-ene-17-one 

Downstream Products

• 196881-37-5 C₃₇H₄₅NO₆S 
• 948907-54-8 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester 
• 159811-51-5 CDB-3236 
• 126784-99-4 ulipristal acetate 

Relevant academic research and scientific papers

Acetic acid wu lisi he and its intermediate preparation method

The invention discloses a preparation method of ulipristal acetate and an intermediate thereof, and belongs to the field of pharmaceutical synthesis. The preparation method of the ulipristal acetate comprises the following steps: by taking 3,3-(ethylenedioxy)-19-methylestra-5(10),9(11)-diene-3,17-diketone as raw material, enabling the raw material to react with sodium acetylide or potassium acetylide to obtain a compound III, carrying out high-selectivity epoxidation by oxide to obtain a compound IV, subsequently enabling the compound IV to react with 4-(N,N-dimethyl amino) phenyl magnesium bromide Grignard reagent to obtain a compound V, then enabling the compound V to react with phenyl sulfonic acid chloride to obtain a compound VI, enabling the compound VI to respectively react with sodium methoxide and trimethyl phosphate to obtain a compound VII, hydrolyzing and removing a protection group to obtain a compound VIII, finally carrying out acetylation reaction to obtain the ulipristal acetate, wherein the reaction formulae are as shown in the description. The method is short in synthetic route, mild in reaction conditions, high in yield and purity of products, low in cost, stable and controllable in quality, and is suitable for industrial production.

A simple and convenient synthetic route to Ulipristal acetate

We set out to describe a new and efficient route for preparing Ulipristal acetate with a good yield. The selected epoxidization conditions gave out 80% of 5α,10α-epoxide 2a in the two diastereoisomers which greatly improved the yield of 11β-substituted isomer 4a. And phenyl-sulfinyl compound 6 was synthesized from ketone 5 directly treated with phenylsulfenyl chloride in the presence of triethylamine. These synthetic procedures is only 8 steps, less than currently reported in the literature, but more suitable for industrial process.

Novel phosphorus-containing 17β-side chain mifepristone analogues as progesterone receptor antagonists

A novel series of steroidal compounds were designed and synthesized with various phosphorus-containing groups on the 17β-side chain as progesterone receptor antagonists. The structure-activity relationships of these compounds are discussed. Selected compo

11,21-Bisphenyl-19-norpregnane derivatives are selective antiglucocorticoids

An efficient eight-step synthesis of 11,21-bisphenyl-19-norpregnane derivatives (10) starting from 19-norandrosta-4,9-diene-3,17-dione (5) is described. It is shown that specific combinations of polar substitutions on the 11- and the 21-phenylring in compounds (10) lead to selective antiglucocorticoids with relative high binding to the glucocorticoid receptor and almost negligible binding to the progesterone receptor.