24284-84-2

Usage

Uses

Used in Pharmaceutical Industry:
Sts 64 is used as an impurity in Dienogest (D441870), a contraceptive agent, for its role in family planning and reproductive health.
Used in Healthcare Industry:
Sts 64 is used to decrease blood cholesterol levels in women with hypercholesterolemia, contributing to the management and treatment of cardiovascular diseases.

InChI:InChI=1/C21H27NO2/c1-20-9-7-17-16-6-4-15(24-2)13-14(16)3-5-18(17)19(20)8-10-21(20,23)11-12-22/h4,6,13,17-19,23H,3,5,7-11H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1

Upstream product

• 67473-36-3 17α-Cyanomethyl-17β-hydroxyestr-4-en-3-one 
• 65928-58-7 Dienogest 
• 1624-62-0 estrone 3-methyl ether 
• 75-05-8 acetonitrile 

Relevant academic research and scientific papers

METHOD FOR SYNTHESIS OF DIENOGEST FROM ESTRONE-3-METHYLETHER

A method for the synthesis of dienogest from 3-methoxy-estra-1,3,5-trien-17-one includes the steps of a) reacting 3-methoxy-estra-1,3,5-trien-17-one with alcohol in the presence of an acid in an organic solvent to form 3-methoxy-17,17-dialkoxy-estra-1,3,5

Process for the production of unsaturated 17 α-cyanomethyl-17 β-h

The unsaturated 17α-cyanomethyl-17β-hydroxy steroids of the formula I, STR1 in which R 1 =Me, Eth; R 2 =H, Me; R 3 =H, OH, an acetoxy or alkoxy group; R 4 =H, R 5 =OH, an acetoxy, alkoxy group of R 4 and R 5 together represent a keto- or ketal group and double bonds are contained in the basic structure of the steroid, particularly between the 15 and 16 position in the steroid ring, from unsaturated 17-ketosteroids of the general formula II as described herein with the aforementioned meanings of R 1 to R 5 by reacting the unsaturated 17-ketosteroids with LiCH 2 CN and subsequently hydrolyzing.The compounds of formula I are pharmacologically interesting steroid compounds or also intermediate products for the synthesis of highly-effective steroid products which can be used in human and veterinary medicine for the treatment of endocrine disorders and for reproductive control based on their specific hormonal/anti-hormonal actions.The compounds are suitable for the treatment of endometriosis and also in combination with preparations with ethinylestradiol for fertility control.

MICROBIAL TRANSFORMATION OF 17α-CYANOMETHYL-17-HYDROXY-4,9-ESTRADIEN-3-ONE (STS 557) AND 17α-CYANOMETHYL-19-NORTESTOSTERONE BY MYCOBACTERIUM SMEGMATIS

Microbial transformation of the new progestagen STS 557 (17α-cyanomethyl-17-hydroxy-4,9-estradien-3-one) by Mycobacterium smegmatis yielded predominantly ring A-aromatized compounds. 17α-cyanomethyl-1,3,5(10),9(11)-estratetraene-3,17-diol, 17α-cyanomethyl-1,3,5(10)-estratriene-3,17-diol and the corresponding 3-methyl ethers.The analogous compound without the 9(10) double bound, 17α-cyanomethyl-19-nortestosterone, was transformed mainly to 5α-hydrogenated metabolites: 17α-cyanomethyl-17-hydroxy-5α-estran-3-one, 17α-cyanomethyl-17-hydroxy-5α-1-estren-3-one, 17α-cyanomethyl-5α-estrane-3α,17-diol, and 17α-cyanomethyl-5α-estrane- 3β,17-diol.From these results, it is concluded that 4,9-dien-3-oxo compounds are not substrates for enzymatic 5α-hydrogenation.

Synthesis and uterotrophic effect of new 'impeded estrogens', viz. estradiol 3 methyl ether derivatives of 17α substituted type

Synthesis of new types of estrogens, derivatives of estradiol 3 methyl ether with a CH2X substituent at the 17α position (X = halogen, pseudohalides, N, S, or O containing groups) is reported. Estrogenic activity of these substances was studied in a uterotrophic assay on infantile mice. The uterotrophic effect is markedly reduced by introduction of CH2X substituents at 17α. The most active compounds (X = SCN, N3, NHCH3, NAcCH3) have about 20 to 50% of the activity of estradiol when given by gavage. Like estradiol they show a flat slope of the dose response curves and are classified as 'impeded estrogens'.