Anti-inflammatory androstane derivative
AssigneeGlaxo Group Limited
InventorsKeith Biggadike, Steven John Coote, Rosalyn Kay Nice
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Abstract
According to one aspect of the invention, there is provided a compound of formula (I) and solvates thereof. There are also provided compositions containing the compound, processes for preparing it, and its use in therapy.
Claims206
A compound of formula (I)
- or solvates thereof.
A compound of formula (I)
- in unsolvated form in the form of Form 1 polymorph, said Form 1 polymorph characterized by an XRPD profile having a peak at around 18.9 degrees 2Theta.
A compound of formula (I)
- in unsolvated form in the form of Form 2 polymorph, said Form 1 polymorph characterized by an XRPD profile having a peak at around 18.9 degrees 2Theta.
A compound of formula (I)
- in unsolvated form in the form of Form 3 polymorph, said Form 1 polymorph characterized by an XRPD profile having a peak at around 18.9 degrees 2Theta.
A compound of formula (II)
- or a salt thereof.
A process for preparing a compound of formula (II)
- which comprises:
- (a) reacting a compound of formula (III)
- with an activated derivative of 2-furoic acid in an amount of at least 2 moles of activated derivative per mole of compound of formula (III) to yield a compound of formula (IIA)
- ;
- and
- (b) removal of the sulphur-linked 2-furoyl moiety from compound of formula (IIA) by reaction of the product of step (a) with a further mole of compound of formula (III) to give two moles of compound of formula (II).
A compound of formula (IIA)
A compound of formula (IXA)
- wherein X represents halogen.
A compound of formula (XV)
- wherein P represents a hydroxy protecting group.
A compound of formula (XVI)
A compound of formula (XVII)
- or a salt thereof wherein P represents a hydroxy protecting group.
A compound of formula (XX)
- or a salt thereof or a derivative wherein the 11-carbonyl group is masked.
A compound of formula (XXIII)
- wherein L represents a leaving group other than fluorine.
A process for preparing a compound of formula (I) or a solvate thereof which comprises:
- (a) providing a compound of formula (I)
- or a solvate thereof in which the 11-β-hydroxy group is protected or masked and
- (b) deprotecting or unmasking said compound to yield the compound of formula (I) or a solvate thereof.
A process for the preparation of a compound of formula (I) or a solvate thereof which comprises:
- (a) providing a derivative of a compound of formula (I)
- or a solvate thereof in which the 3-carbonyl group is protected or masked, and
- (b) deprotecting or unmasking said derivative of a compound of formula (I).
A process for preparing a compound of formula (II)
- which comprises treating a compound of formula (X)
- with a reagent suitable for converting a carboxylic acid to a carbothioic acid.
Dependencies are inferred from the claim text.