- PROCESS FOR MAKING THE 17-TRIFLATE INTERMEDIATE OF ABIRATERONE-3-ACETATE
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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.
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Page/Page column 16; 17
(2014/05/24)
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- METHANESULFONATE SALTS OF ABIRATERONE-3-ESTERS AND RECOVERY OF SALTS OF ABIRATER ONE-3-ESTERS FROM SOLUTION IN METHYL TERT-BUTYL ETHER
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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).
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Page/Page column 17-20
(2008/06/13)
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- 17-substituted steroids useful in cancer treatment
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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.
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- Novel Steroidal Inhibitors of Human Cytochrome P45017α (17α-Hydroxylase-C17,20-lyase): Potential Agents for the Treatment of Prostatic Cancer
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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.
- Potter, Gerard A.,Barrie, S. Elaine,Jarman, Michael,Rowlands, Martin G.
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p. 2463 - 2471
(2007/10/02)
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