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US 2012/0232047 A1Published application
Substituted clavulanic acid
AssigneeNabriva Therapeutics AG
InventorAtchyuta Rama Chandra Murty Bulusu
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Abstract
The present invention relates to compounds of formula I and to compounds of formula II wherein the substituents have various meanings. These compounds are useful as beta lactamase inhibitors.
Claims17
A compound of formula I
- wherein
- X is COOH or salts thereof,
- COOR1, wherein R1 is C1-4 alkyl which is optionally substituted,
- CONR2R3, wherein R2 and R3 independently represent H or C1-5 alkyl which optionally contains one or more hetero atoms selected from O, S and N and/or is optionally substituted, or
- CON(R2)—CH(R4)—R5, wherein
- R2 is as defined above,
- R4 is a group usually found in the α position of α-amino acids, and
- R5 is COOH or a salt thereof;
- COOR1, wherein R1 is as defined above;
- or
- CONR2R3, wherein R2 and R3 are as defined above,
- Y and Y′ are both H or together represent ═O,
- Z is O, NR2 or N—CH(R4)—R5, wherein R2, R4 and R5 are as defined above,
- n is 1 or 2,
- m is a number from 0 to 4, and
- R is H, or
- a saturated or unsaturated chain containing 1 to 8 carbon atoms, which is optionally substituted by a 5 or 6-membered nonaromatic ring containing one or more hetero atoms selected from O, S and N, or by aryl, alkyl or cycloalkyl, optionally containing one or more hetero atoms selected from O, S and N, and/or is optionally substituted with one or more heteroatoms selected from O, S and N, halogens Cl, Br, I and F and/or azido N3.
14 more elements
An intermediate of formula II
- wherein
- X is COOH or salts thereof,
- COOR1, wherein R1 is C1-4 alkyl which is optionally substituted,
- CONR2R3, wherein R2 and R3 independently represent H or C1-5 alkyl which optionally contains one or more hetero atoms selected from O, S and N and/or is optionally substituted, or
- CON(R2)—CH(R4)—R5, wherein
- R2 is as defined above,
- R4 is a group usually found in the α position of α-amino acids, and
- R5 is COOH or a salt thereof;
- COOR1, wherein R1 is as defined above;
- or
- CONR2R3, wherein R2 and R3 are as defined above,
- either R6 or R7 is H, with the proviso that
- if R7 is H, R6 is a saturated or unsaturated chain containing 1 to 11 carbon atoms, which is optionally substituted by a 5 or 6-membered nonaromatic ring containing one or more heteroatoms selected from O, S and N, or by aryl, alkyl or cycloalkyl, optionally containing one or more hetero atoms selected from O, S and N, and/or is optionally substituted by one or more hetero atoms selected from O, S and N, halogens Cl, Br, I and F and/or azido N3,
- and vice versa;
- and
- R8 is COOH, CH2OH or CHO.
13 more elements
Dependencies are inferred from the claim text.