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US 2010/0137282 A1Published application
Tricyclic nitrogen containing compounds as antibacterial agents
AssigneeGlaxo Group Limited
InventorsDavid Evan Davies, David Thomas Davies, Ilaria Giordano, Alan Joseph Hennessy, Neil David Pearson
Life of this patent
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Abstract
Tricyclic nitrogen containing compounds and their use as antibacterials. Z1 and Z2 are independently selected from CH and N.
Claims13
A compound of formula (I) or a pharmaceutically acceptable salt and/or N-oxide thereof:
- wherein:
- Z1 and Z2 are independently selected from CH and N;
- R1a and R1b are independently selected from hydrogen;
- halogen;
- cyano;
- (C1-6)alkyl;
- (C1-6)alkylthio;
- trifluoromethyl;
- trifluoromethoxy;
- carboxy;
- hydroxy optionally substituted with (C1-6)alkyl or (C1-6)alkoxy-substituted(C1-6)alkyl;
- (C1-6)alkoxy-substituted(C1-6)alkyl;
- hydroxy (C1-6)alkyl;
- an amino group optionally N-substituted by one or two (C1-6)alkyl, formyl, (C1-6)alkylcarbonyl or (C1-6)alkylsulphonyl groups;
- and aminocarbonyl wherein the amino group is optionally substituted by (C1-4)alkyl;
- provided that R1a and R1b are H when Z2 or Z1 is N, respectively;
- R2 is hydrogen, or (C1-4)alkyl, or together with R6 forms Y as defined below;
- A is a group (i):
- in which:
- R3 is as defined for R1a and R1b or is oxo and n is 1 or 2:
- or A is a group (ii)
- W1, W2 and W3 are CR4R8
- or W2 and W3 are CR4R8 and W1 represents a bond between W3 and N.
- X is O, CR4R8, or NR6;
- one R4 is as defined for R1a and R1b and the remainder and R8 are hydrogen or one R4 and R8 are together oxo and the remainder are hydrogen;
- R6 is hydrogen or (C1-6)alkyl;
- or together with R2 forms Y;
- R7 is hydrogen;
- halogen;
- hydroxy optionally substituted with (C1-6)alkyl;
- or (C1-6)alkyl;
- Y is CR4R8CH2;
- CH2CR4R8;
- (C═O);
- CR4R8;
- CR4R8(C═O);
- or (C═O)CR4R8;
- or when X is CR4R8, R8 and R7 together represent a bond;
- U is selected from CO, and CH2 and
- R5 is an optionally substituted bicyclic carbocyclic or heterocyclic ring system (B):
- containing up to four heteroatoms in each ring in which
- at least one of rings (a) and (b) is aromatic;
- X1 is C or N when part of an aromatic ring, or CR14 when part of a non-aromatic ring;
- X2 is N, NR13, O, S(O)x, CO or CR14 when part of an aromatic or non-aromatic ring or may in addition be CR14R15 when part of a non aromatic ring;
- X3 and X5 are independently N or C;
- Y1 is a 0 to 4 atom linker group each atom of which is independently selected from N, NR13, O, S(O)x, CO and CR14 when part of an aromatic or non-aromatic ring or may additionally be CR14R15 when part of a non aromatic ring;
- Y2 is a 2 to 6 atom linker group, each atom of Y2 being independently selected from N, NR13, O, S(O)x, CO, CR14 when part of an aromatic or non-aromatic ring or may additionally be CR14R15 when part of a non aromatic ring;
- each of R14 and R15 is independently selected from:
- H;
- (C1-4)alkylthio;
- halo;
- carboxy(C1-4)alkyl;
- (C1-4)alkyl;
- (C1-4)alkoxycarbonyl;
- (C1-4)alkylcarbonyl;
- (C1-4)alkoxy (C1-4)alkyl;
- hydroxy;
- hydroxy(C1-4)alkyl;
- (C1-4)alkoxy;
- nitro;
- cyano;
- carboxy;
- amino or aminocarbonyl optionally mono- or di-substituted by (C1-4)alkyl;
- or
- R14 and R15 may together represent oxo;
- each R13 is independently H;
- trifluoromethyl;
- (C1-4)alkyl optionally substituted by hydroxy, (C1-6)alkoxy, (C1-6)alkylthio, halo or trifluoromethyl;
- (C2-4)alkenyl;
- (C1-4)alkoxycarbonyl;
- (C1-4)allylcarbonyl;
- (C1-6)alkylsulphonyl;
- aminocarbonyl wherein the amino group is optionally mono or disubstituted by (C1-4)alkyl;
- and
- each x is independently 0, 1 or 2.
72 more elements
11-13. (canceled)
Dependencies are inferred from the claim text.