US 5,854,280 AGranted

Antifungal sordaridin derivatives

AssigneeGlaxo Wellcome Inc.

InventorsJose R. Ruiz Gomez, Jose Maria Bueno Calderon, Silvestre Garcia-Ochoa Dorado, Maria T. Fraile Gabaldon, Julia C. Pichel, Jose M. Fiandor Roman, Domingo Gargallo Viola, Juan C. Cuevas Zurita, Jose L. Lavandera Diaz, Sophie Huss

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Abstract

A compound of formula ##STR1## wherein Z is a tetrahydro-pyrano group selected from ##STR2## having antifungal activity processes for their preparation and their use in medicines.

Claims15

Dependent claims

A compound of formula ##STR27## wherein Z is a tetrahydro-pyrano group selected from ##STR28## and pharmaceutically acceptable salts and solvates or metabolically labile derivatives thereof,

wherein R.sup.1 represents hydrogen, halogen, hydroxyl, C.sub.1-4 alkoxy or acyloxy;
R.sup.2 and R.sup.3 may each independently represent hydrogen, C.sub.1-6 alkyl or C.sub.1-4 alkoxy C.sub.1-4 alkyl or R.sup.2 and R.sup.3 may together with the carbon atom to which they are attached represent C.dbd.O, C.dbd.S or C.sub.3-8 cycloalkyl;
R.sup.4 represents hydrogen or CH.sub.2 R.sup.7 (where R.sup.7 is hydrogen, hydroxyl, C.sub.1-4 alkoxy or a group OCOR.sup.8 in which R.sup.8 is C.sub.1-4 alkyl or aryl);
R.sup.5 and R.sup.6 may each independently represent hydrogen, C.sub.1-6 alkyl or C.sub.1-4 alkoxy C.sub.1-4 alkyl or R.sup.5 and R.sup.6 may together with the carbon atom to which they are attached represent C.dbd.O, C.dbd.S or C.sub.3-8 cycloalkyl;
n represents zero or 1;
X and Y may each independently represent oxygen, sulphur or CR.sup.9 R.sup.10 (where R.sup.9 and R.sup.10 may each independently represent hydrogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy or C.sub.1-4 alkoxy C.sub.1-4 alkyl or R.sup.9 and R.sup.10 may together with the carbon atom to which they are attached represent C.dbd.O, C.dbd.S, C.sub.3-8 cycloalkyl or C.dbd.CHR.sup.11 where R.sup.11 represents hydrogen or C.sub.1-4 alkyl);
or when X or Y is oxygen and n is zero then --Y--CR.sup.2 R.sup.3 or --X--CR.sup.2 R.sup.3 -- respectively may also represent --N.dbd.CR.sup.3 -- or --NR.sup.12 --CR.sup.2 R.sup.3 -- (where CR.sup.2 and R.sup.3 are C.dbd.O and R.sup.12 is C.sub.1-4 alkyl an acyl group COR.sup.13 where R.sup.13 is C.sub.1-6 alkyl) or when Y is oxygen and n is zero X may be represent the group CR.sup.11 which is attached to the pyran ring by a double bond;
R.sup.15 represents hydrogen, halogen, azido, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy (optionally substituted by 1 or 2 hydroxy or a ketal thereof or 1 or 2 C.sub.1-3 alkoxy groups), aryl C.sub.1-4 alkoxy, C.sub.3-6 alkenyloxy, a group OCOR.sup.18 (where R.sup.18 is arylC.sub.1-4 alkoxy or a C.sub.1-10 alkyl group optionally containing one or two double bonds) or C.sub.1-6 alkoxycarbonyl C.sub.1-4 alkoxy, and R.sup.16 represents hydrogen or R.sup.15 and R.sup.16 may together with the carbon atom to which they are attached represent C.dbd.O or C.dbd.CH.sub.2 ;
R.sup.17 represents CH.sub.2 R.sup.19 where R.sup.19 is hydrogen, hydroxyl, C.sub.1-14 alkoxy or a group OCOR.sup.20 in which R.sup.20 is C.sub.1-4 alkyl);
and
W represents an oxygen or sulphur atom or a CH.sub.2 group;
and the dotted line in group (a) indicates the optional presence of an additional bond.

9 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/669,441Filed 18 Oct 1996
Priority: EP 945001738 Nov 1994
Granted: 29 Dec 1998
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 493/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
A61P 31/10
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antimycotics
C07D 311/02
Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings: ortho- or…

Family

No related US applications are recorded in the indexed filing history.

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Antifungal sordaridin derivatives

AssigneeGlaxo Wellcome Inc.

Life of this patent

Estimating the term…

Abstract

A compound of formula ##STR1## wherein Z is a tetrahydro-pyrano group selected from ##STR2## having antifungal activity processes for their preparation and their use in medicines.

A compound of formula ##STR27## wherein Z is a tetrahydro-pyrano group selected from ##STR28## and pharmaceutically acceptable salts and solvates or metabolically labile derivatives thereof,

wherein R.sup.1 represents hydrogen, halogen, hydroxyl, C.sub.1-4 alkoxy or acyloxy;
R.sup.2 and R.sup.3 may each independently represent hydrogen, C.sub.1-6 alkyl or C.sub.1-4 alkoxy C.sub.1-4 alkyl or R.sup.2 and R.sup.3 may together with the carbon atom to which they are attached represent C.dbd.O, C.dbd.S or C.sub.3-8 cycloalkyl;
R.sup.4 represents hydrogen or CH.sub.2 R.sup.7 (where R.sup.7 is hydrogen, hydroxyl, C.sub.1-4 alkoxy or a group OCOR.sup.8 in which R.sup.8 is C.sub.1-4 alkyl or aryl);
R.sup.5 and R.sup.6 may each independently represent hydrogen, C.sub.1-6 alkyl or C.sub.1-4 alkoxy C.sub.1-4 alkyl or R.sup.5 and R.sup.6 may together with the carbon atom to which they are attached represent C.dbd.O, C.dbd.S or C.sub.3-8 cycloalkyl;
n represents zero or 1;
X and Y may each independently represent oxygen, sulphur or CR.sup.9 R.sup.10 (where R.sup.9 and R.sup.10 may each independently represent hydrogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy or C.sub.1-4 alkoxy C.sub.1-4 alkyl or R.sup.9 and R.sup.10 may together with the carbon atom to which they are attached represent C.dbd.O, C.dbd.S, C.sub.3-8 cycloalkyl or C.dbd.CHR.sup.11 where R.sup.11 represents hydrogen or C.sub.1-4 alkyl);
or when X or Y is oxygen and n is zero then --Y--CR.sup.2 R.sup.3 or --X--CR.sup.2 R.sup.3 -- respectively may also represent --N.dbd.CR.sup.3 -- or --NR.sup.12 --CR.sup.2 R.sup.3 -- (where CR.sup.2 and R.sup.3 are C.dbd.O and R.sup.12 is C.sub.1-4 alkyl an acyl group COR.sup.13 where R.sup.13 is C.sub.1-6 alkyl) or when Y is oxygen and n is zero X may be represent the group CR.sup.11 which is attached to the pyran ring by a double bond;
R.sup.15 represents hydrogen, halogen, azido, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy (optionally substituted by 1 or 2 hydroxy or a ketal thereof or 1 or 2 C.sub.1-3 alkoxy groups), aryl C.sub.1-4 alkoxy, C.sub.3-6 alkenyloxy, a group OCOR.sup.18 (where R.sup.18 is arylC.sub.1-4 alkoxy or a C.sub.1-10 alkyl group optionally containing one or two double bonds) or C.sub.1-6 alkoxycarbonyl C.sub.1-4 alkoxy, and R.sup.16 represents hydrogen or R.sup.15 and R.sup.16 may together with the carbon atom to which they are attached represent C.dbd.O or C.dbd.CH.sub.2 ;
R.sup.17 represents CH.sub.2 R.sup.19 where R.sup.19 is hydrogen, hydroxyl, C.sub.1-14 alkoxy or a group OCOR.sup.20 in which R.sup.20 is C.sub.1-4 alkyl);
and
W represents an oxygen or sulphur atom or a CH.sub.2 group;
and the dotted line in group (a) indicates the optional presence of an additional bond.

9 more elements

Facts

Application

08/669,441Filed 18 Oct 1996

Priority

EP 945001738 Nov 1994

Granted

29 Dec 1998

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 493/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
A61P 31/10
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antimycotics
C07D 311/02
Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings: ortho- or…