154229-36-4

Usage

Uses

Used in Pharmaceutical Industry:
Androsta-3,5,16-trien-17-ol Trifluoromethanesulfonate is used as an intermediate in the synthesis of Abiraterone Acetate, a drug used for the treatment of metastatic castration-resistant prostate cancer. Its role in the pharmaceutical industry is crucial for the production of this life-saving medication.
Used in Chemical Research:
Due to its unique chemical properties, Androsta-3,5,16-trien-17-ol Trifluoromethanesulfonate can be utilized in various chemical research applications. It may serve as a starting material or a catalyst in the development of new compounds and pharmaceuticals, contributing to the advancement of scientific knowledge and innovation in the field.
Used in Drug Synthesis:
Androsta-3,5,16-trien-17-ol Trifluoromethanesulfonate is used as a key component in the synthesis of other drugs and pharmaceutical compounds. Its unique structure and properties make it a valuable asset in the development of novel therapeutic agents, potentially leading to the discovery of new treatments for various diseases and conditions.

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 853-23-6 prasterone acetate 
• 115375-60-5 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 154229-20-6 17-(3-pyridyl)androsta-3,5,16-triene 

Relevant academic research and scientific papers

PROCESS FOR MAKING THE 17-TRIFLATE INTERMEDIATE OF ABIRATERONE-3-ACETATE

The present invention relates to a process for making the compound 3β-acetoxy- androsta-5,16-dien-17-yl trifluoromethanesulfonate of formula (5) and is characterized in that dehydroepiandrosterone-3-acetate of formula (2) is reacted with a triflating agent, preferably trifluoromethanesulfonic anhydride, in an inert solvent in the absence of an organic base.

METHANESULFONATE SALTS OF ABIRATERONE-3-ESTERS AND RECOVERY OF SALTS OF ABIRATER ONE-3-ESTERS FROM SOLUTION IN METHYL TERT-BUTYL ETHER

A salt of a compound of formula (I) may be made with methanesulfonic acid. The salt and salts with other acids may be prepared by recovering from methyl tert-butyl ether (MTBE).

17-substituted steroids useful in cancer treatment

Compounds of the general formula (1) STR1 wherein X represents the residue of the A, B and C rings of a steroid, R represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, R 14 represents a hydrogen atom and R 15 represents a hydrogen atom or an alkyl or alkoxy group of 1-4 carbon atoms, or a hydroxy or alkylcarbonyloxy group of 2 to 5 carbon atoms or R 14 and R 15 together represent a double bond, and R 16 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, in the form of the free bases or phannaceutically acceptable acid addition salts, are useful for treatment of androgen-dependent disorders, especially prostatic cancer, and also oestrogen-dependent disorders such as breast cancer.

Novel Steroidal Inhibitors of Human Cytochrome P45017α (17α-Hydroxylase-C17,20-lyase): Potential Agents for the Treatment of Prostatic Cancer

Steroidal compounds having a 17-(3-pyridyl) substituent together with a 16,17-double bond have been synthesized, using a palladium-catalyzed cross-coupling reaction of a 17-enol triflate with diethyl(3-pyridyl)borane, which are potent inhibitors of human testicular 17α-hydroxylase-C17,20-lyase.The requirement for these structural features is stringent: compounds having 2-pyridyl (9), 4-pyridyl (10), or 2-pyridylmethyl (11) substituents instead of the 3-pyridyl substituent were either poor inhibitors or noninhibitory.Reduction of the 16,17-double bond to give 17β-pyridyl derivatives diminished potency with 3-pyridyl substitution (327; IC50 for lyase, 2.923 nM) but increased it with a 4-pyridyl substituent present (1028; IC50 1 μM53 nM).In contrast, a variety of substitution patterns in rings A-C of the steroid skeleton afforded inhibitors having potencies similar to those most closely related structurally to the natural substrates pregnenolone and progesterone, respectively 17-(3-pyridyl)androsta-5,16-dien-3β-ol (3, Kiapp 1 nM; IC50 for lyase, 2.9 nM) and 17-(3-pyridyl)androsta-4,16-dien-3-one (15; IC50 for lyase, 2.1 nM).Thus compounds having variously aromatic ring A (18), saturated rings A/B (21,22), and oxygenated ring C (26) exhibited IC50 values for lyase (1.8-3.0 nM) falling within a 2-fold range.The most potent compounds are candidates for development as drugs for the treatment of hormone-dependent prostatic carcinoma.