- PROCESS FOR THE PREPARATION OF 17-DESOXY-CORTICOSTEROIDS
-
The present invention provides an improved process for the preparation of 17-desoxy corticosteroid derivatives in a single chemical step by reacting the 17-hydroxy starting material with an excess of Trimethylsilyl Iodide. The present invention is specifically advantageous in preparing 17-desoxy corticosteroid derivatives having one or more halogen groups at positions 2, 6, 7 or 9 of the corticosteroid such as Clocortolone or Desoximetasone.
- -
-
Page/Page column 15-16
(2012/02/05)
-
- Process for the synthesis of the hydroxyacetyl side-chain of steroids of the pregnane type, novel 21-hydroxy-20-oxo-17α-pregnane compounds and pharmaceutical preparations containing them
-
The present invention relates to a novel general process for synthesizing a α- or β-oriented hydroxyacetyl side chain of steroids of the pregnane type, which comprises treating a corresponding steroid carbaldehyde in succession with formaldehyde dimethylmercaptal-S-oxide in the form of an alkali metal salt thereof, and with a strongly acid hydrolysing agent.Preferred final products are compounds of the formula STR1 wherein n is 1 or 2, R 2 represents methyl or difluoromethyl, and R 1 represents hydroxymethyl, methoxymethyl, acetoxymethyl or hydrogen, and, if n is 2 and/or R 2 is difluoromethyl, R 1 also represents methyl. These compounds act as agonists or antagonists of natural steroid hormones. The antigestagenic 19,21-dihydroxy-17α-pregn-4-ene-3,20-dione and its 6,7-dehydro derivatives and diacetates are of particular interest.
- -
-
-
- Cytotoxic nucleoside-corticosteroid phosphodiesters
-
Nucleotides of nucleosides or bases having known cytotoxic activity are reacted with steroids, preferably corticosteroids, to form corresponding cytotoxic nucleoside-corticosteroid phosphodiester analogues of the formula: STR1 wherein: steroid is the residue formed by removal of a hydroxyl hydrogen atom from a natural or synthetic adrenal corticosteroid containing the characteristic cyclopentanophenanthrene nucleus which is esterified to the phosphate moiety at the 21-position; sugar is a naturally occurring pentose or deoxypentose in the furanose form, preferably ribose, deoxyribose, lyxose, xylose or arabinose and especially ribose, deoxyribose or arabinose, which is esterified to the phosphate moiety at the 5'-position and covalently bonded to the heterocycle moiety at the 1'-position to form a nucleoside; and heterocycle is a purine, pyrimidine, hydrogenated pyrimidine, triazolopurine or similar nucleoside base. The conjugates exhibit an enhanced therapeutic index as compared to the parent nucleoside or base compounds, and are thus useful cytotoxic, antiviral and antineoplastic agents.
- -
-
-
