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US 2004/0024059 A1Published application
Novel pleuromutilin derivatives
AssigneeSmithKline Beecham Corporation
InventorsJohn Stephen Elder, Andrew Keith Forrest, Richard Lewis Jarvest, Robert John Sheppard
Life of this patent
Estimating the term…
Abstract
Pleuromutilin compounds of the formula (A) & (B) are of use in anti-bacterial therapy.
Claims15
A compound of formula (IA) or (IB):
- 139
- in which:
- R1 is optionally substituted C(1-6)alkyl or C(3-6)cycloalkyl or optionally substituted heterocyclyl;
- R2 is vinyl or ethyl;
- R3 is H, OH or F, and R4 is H, or R3 is H and R4 is F, and R5 and R6 together form an oxo group;
- or
- R3 and R4 is each H, R5 is OH or H and R6 is H, or R5 is H and R6 is OH or H.
4 more elements
A compound as claimed in any one of the preceding claims in which R3 and R4 are both hydrogen, and R5 and R6 together form an oxo group.
A compound of formula (1) according to any one of Examples 1 to 130.
A method of preparing a compound of formula (IA) or (IB) which process comprises:
- (a) reacting a chloroformate compound of formula (IIA) or (IIB):
- 140
- in which:
- P is hydrogen or an hydroxy-protecting group;
- R2A, R3A, R4A, R5A and R6A are R2, R3, R4, R5 and R6 as defined for formulae (IA) and (IB) or a group convertible to R2, R3, R4, R5 and R6 respectively;
- with silver cyanate, in a suitable aprotic solvent, for instance dichloromethane, followed by treating with an alcohol compound of formula (a):
- R1AOH (III)
- in which R1A is R1 as defined for formulae (IA) and (IB) or a group convertible to R1;
- in the presence of pyridine, in a carbamate forming reaction, and thereafter, and if so needed;
- converting P to hydrogen, and, if necessary, converting an R2A, R3A, R4A, R5A and R6A group to an R2, R3, R4, R5 and R6 group;
- or
- (b) chloroformate epi-mutilin compound of formula (IIC):
- 141
- wherein
- R2A is as hereinbefore defined;
- with silver cyanate and then a compound of formula (III), as hereinbefore defined;
- under carbamate forming conditions as hereinbefore described;
- and then treating the product with an acid;
- and where required or desired converting an R1A group to an R1 group and an R2A group to an R2 group;
- or
- (c) a process corresponding to (a) or (b) in which the chloroformate component comprises R1A and the alcohol component comprises the mutilin nucleus.
18 more elements
Dependencies are inferred from the claim text.