21,21-Dihalo steroids
AssigneeSyntex (U.S.A.) Inc.
InventorsTsung-tee Li, Michael Marx, Lewis J. Throop
Life of this patent
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Abstract
Novel, topically-active anti-inflammatory steroids are represented by the formula ##STR1## wherein X is fluoro, chloro or hydrogen; X.sup.1 is fluoro, chloro, bromo, or hydrogen; X.sup.2 is hydroxy or may be chloro when X.sup.1 is chloro; and X.sup.3 and X.sup.4 are independently fluoro, chloro or bromo. These steroids are prepared by formylating at the 21-position a 16.alpha.,17.beta.-isopropylidenedioxypregna-1,4,9(11)-triene-3,20-dione or the corresponding 21-fluoro compound, halogenating at the 21 position, deformylating, then reacting to add the desired components at the 9.alpha. and 11.beta. positions.
Claims29
A compound chosen from those represented by the formula ##STR22## X is hydrogen, fluoro, or chloro;
- X.sup.1 is hydrogen, fluoro, chloro or bromo;
- X.sup.2 is hydroxy or may be chloro when X.sup.1 is chloro;
- X.sup.3 and X.sup.4 are independently fluoro, chloro or bromo;
- and
- the broken line between C-1 and C-2 indicates that the bond between C-1 and C-2 is a single or a double bond.
A process for preparing 21,21-dihalosteroids which process comprises
- a. reacting a formylating agent with a compound represented by the formula ##STR23## wherein X is fluoro, chloro, or hydrogen to form a compound represented by the formula ##STR24## wherein X is previously defined;
- b. reacting the compound represented by formula (III) of this claim with a brominating or chlorinating agent to form a compound represented by the formula ##STR25## wherein X is previously defined and X.sup.3 is chloro or bromo;
- and
- c. reacting the compound represented by formula (IV) with a deformylating agent to form a compound represented by the formula ##STR26## wherein X and X.sup.3 are defined previously.
A process for preparing 21,21-dihalosteroids which process comprises
- a. reacting a formylating agent with a compound represented by the formula ##STR37## wherein X is fluoro, chloro, or hydrogen, to form a compound represented by the formula ##STR38## wherein X is previously defined;
- b. reacting the compound represented by formula (III) of this claim with a brominating or chlorinating agent to form a compound represented by the formula ##STR39## wherein X is previously defined and X.sup.3 is chloro or bromo;
- c. reacting the compound represented by formula (IV) with a brominating or chlorinating agent to form a compound represented by the formula ##STR40## wherein X and X.sup.3 are defined previously and X.sup.4 is bromo or chloro;
- and
- d. reacting the compound of step (c) with a deformylating agent to form a compound represented by the formula ##STR41## wherein X and X.sup.3 are defined previously in this claim.
Dependencies are inferred from the claim text.