CA2513463A1 - Gyrase inhibitors and uses thereof - Google Patents
Gyrase inhibitors and uses thereof Download PDFInfo
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- CA2513463A1 CA2513463A1 CA002513463A CA2513463A CA2513463A1 CA 2513463 A1 CA2513463 A1 CA 2513463A1 CA 002513463 A CA002513463 A CA 002513463A CA 2513463 A CA2513463 A CA 2513463A CA 2513463 A1 CA2513463 A1 CA 2513463A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Abstract
The present invention relates to compounds which inhibit bacterial gyrase and/or Topo IV and pharmaceutically acceptable compositions comprising said compounds. These compounds, and compositions thereof, are useful in treating bacterial infection. Accordingly, the present invention also relates to methods for treating bacterial infections in mammals. Formula (I).
Claims (31)
1. A compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein:
W is selected from nitrogen, CH, or CF;
X is selected from CH or CF;
Z is O or NH;
R1 is phenyl or a 5-6 membered heteroaryl ring having 1-3 heteroatoms independently selected from oxygen, nitrogen, or sulfur, wherein:
R1 is substituted with 0-3 groups independently selected from -(T)y-Ar, R', oxo, C(O)R', CO2R', OR', N(R')2, SR', NO2, halogen, CN, C(O)N(R')2, NR'C(O)R', SO2R', SO2N(R')2, or NR'SO2R';
y is 0 or 1;
T is a straight or branched C1-4 alkylidene chain, wherein one methylene unit of T is optionally replaced by -O-, -NH-, or -S-;
each R' is independently selected from hydrogen, C1-4 aliphatic, or a 5-6 membered saturated, unsaturated, or aryl ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, wherein:
R' is substituted with 0-3 groups independently selected from halogen, oxo, R
o, N(R o)2, OR o, CO2R o, NR o C(O)R o, C(O)N(R o)2, SO2R o, SO2N(R o)2, or NR o SO2R o, wherein:
each R o is independently selected from hydrogen, C1-4 aliphatic, or a 5-6 membered saturated, unsaturated, or aryl ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, and wherein:
two substituents on adjacent positions of R1 may be taken together to form a 5-membered saturated, partially unsaturated, or aryl ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
Ar is a 3-8 membered saturated, unsaturated, or aryl ring, a 3-7 membered heterocyclic ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or a 5-6 membered heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, wherein:
Ar is substituted with 0-3 groups independently selected from R', oxo, CO2R', OR', N(R')2, SR', NO2, halogen, CN, C(O)N(R')2, NR'C(O)R', SO2R', C(O)R', SO2N(R')2, or NR'SO2R';
R2 is selected from hydrogen or a C1-3 aliphatic group; and Ring A is a 5-6 membered heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, provided that said ring has a hydrogen-bond acceptor in the position adjacent to the point of attachment to Ring B, wherein:
Ring A is substituted with 0-3 groups independently selected from R', oxo, CO2R', OR', N(R')2, SR', NO2, halogen, CN, C(O)N(R')2, NR'C(O)R', SO2R', SO2N(R')2, or NR'SO2R', and wherein:
two substituents on adjacent positions of Ring A may be taken together to form a 5-7 membered saturated, partially unsaturated, or aryl ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur.
or a pharmaceutically acceptable salt thereof, wherein:
W is selected from nitrogen, CH, or CF;
X is selected from CH or CF;
Z is O or NH;
R1 is phenyl or a 5-6 membered heteroaryl ring having 1-3 heteroatoms independently selected from oxygen, nitrogen, or sulfur, wherein:
R1 is substituted with 0-3 groups independently selected from -(T)y-Ar, R', oxo, C(O)R', CO2R', OR', N(R')2, SR', NO2, halogen, CN, C(O)N(R')2, NR'C(O)R', SO2R', SO2N(R')2, or NR'SO2R';
y is 0 or 1;
T is a straight or branched C1-4 alkylidene chain, wherein one methylene unit of T is optionally replaced by -O-, -NH-, or -S-;
each R' is independently selected from hydrogen, C1-4 aliphatic, or a 5-6 membered saturated, unsaturated, or aryl ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, wherein:
R' is substituted with 0-3 groups independently selected from halogen, oxo, R
o, N(R o)2, OR o, CO2R o, NR o C(O)R o, C(O)N(R o)2, SO2R o, SO2N(R o)2, or NR o SO2R o, wherein:
each R o is independently selected from hydrogen, C1-4 aliphatic, or a 5-6 membered saturated, unsaturated, or aryl ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, and wherein:
two substituents on adjacent positions of R1 may be taken together to form a 5-membered saturated, partially unsaturated, or aryl ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur;
Ar is a 3-8 membered saturated, unsaturated, or aryl ring, a 3-7 membered heterocyclic ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or a 5-6 membered heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur, wherein:
Ar is substituted with 0-3 groups independently selected from R', oxo, CO2R', OR', N(R')2, SR', NO2, halogen, CN, C(O)N(R')2, NR'C(O)R', SO2R', C(O)R', SO2N(R')2, or NR'SO2R';
R2 is selected from hydrogen or a C1-3 aliphatic group; and Ring A is a 5-6 membered heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, provided that said ring has a hydrogen-bond acceptor in the position adjacent to the point of attachment to Ring B, wherein:
Ring A is substituted with 0-3 groups independently selected from R', oxo, CO2R', OR', N(R')2, SR', NO2, halogen, CN, C(O)N(R')2, NR'C(O)R', SO2R', SO2N(R')2, or NR'SO2R', and wherein:
two substituents on adjacent positions of Ring A may be taken together to form a 5-7 membered saturated, partially unsaturated, or aryl ring having 0-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur.
2. The compound according to claim 1, wherein Ring A is selected from the following optionally substituted rings:
3. The compound according to claim 2, wherein Ring A is an optionally substituted ring selected from rings a, f, l, s, w, y, or z:
4. The compound according to claim 1, wherein:
R1 is selected from an optionally substituted phenyl or 5-6 membered heteroaryl ring having 1-2 nitrogens.
R1 is selected from an optionally substituted phenyl or 5-6 membered heteroaryl ring having 1-2 nitrogens.
5. The compound according to claim 4, wherein R1 is an optionally substituted ring selected from pyrid-2-yl, pyrid-3-yl, pyrid-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrimidin-6-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, or imidazol-5-yl.
6. The compound according to claim 5, wherein R1 is substituted with 0-2 groups independently selected from halogen, oxo, R', CO2R', OR', N(R')2, SR', C(O)N(R')2, NR'C(O)R', SO2R', SO2N(R')2, or NR'SO2R'.
7. The compound according to claim 6, wherein R2 is selected from methyl, ethyl, isopropyl, or cyclopropyl.
8. The compound according to claim 1, wherein said compound is of formula II-a:
or a pharmaceutically acceptable salt thereof.
or a pharmaceutically acceptable salt thereof.
9. The compound according to claim 1, wherein said compound is of formula III:
or a pharmaceutically acceptable salt thereof, wherein:
the pyridone ring depicted is substituted with 0-2 groups independently selected from halogen, oxo, R', CO2R', OR', N(R')2, SR', C(O)N(R')2, NR'C(O)R', SO2R', SO2N(R')2, or NR'SO2R'.
or a pharmaceutically acceptable salt thereof, wherein:
the pyridone ring depicted is substituted with 0-2 groups independently selected from halogen, oxo, R', CO2R', OR', N(R')2, SR', C(O)N(R')2, NR'C(O)R', SO2R', SO2N(R')2, or NR'SO2R'.
10. The compound according to claim 9, wherein said compound is of formula III-a:
or a pharmaceutically acceptable salt thereof.
or a pharmaceutically acceptable salt thereof.
11. The compound according to claim 10, wherein:
R' is hydrogen or C1-4 aliphatic, and wherein:
R' is optionally substituted with phenyl or pyridyl.
R' is hydrogen or C1-4 aliphatic, and wherein:
R' is optionally substituted with phenyl or pyridyl.
12. The compound according to claim 1, wherein said compound is of formula IV:
or a pharmaceutically acceptable salt thereof.
or a pharmaceutically acceptable salt thereof.
13. The compound according to claim 12, wherein Ar is an optionally substituted 5-6 membered saturated ring having 1-2 heteroatoms independently selected from oxygen, nitrogen, or sulfur.
14. The compound according to claim 12, wherein Ar is an optionally substituted 5-membered heteroaryl ring having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur.
15. The compound according to claim 12, wherein Ar is an optionally substituted 6-membered heteroaryl ring having 1-3 nitrogens.
16. The compound according to claim 12, wherein Ar is optionally substituted phenyl.
17. The compound according to claim 1, wherein said compound is of formula V:
or a pharmaceutically acceptable salt thereof.
or a pharmaceutically acceptable salt thereof.
18. The compound according to claim 17, wherein said compound is of formula VI:
or a pharmaceutically acceptable salt thereof.
or a pharmaceutically acceptable salt thereof.
19. The compound according to any one of claims 8, 11, 12, or 17 wherein R2 is ethyl.
20. A compound selected from the group consisting of:
21. A composition comprising a compound according to claim 1, and a pharmaceutically acceptable carrier, adjuvant, or vehicle.
22. The composition according to claim 21, additionally comprising an additional therapeutic agent selected from an antibiotic, an anti-inflammatory agent, a matrix metalloprotease inhibitor, a lipoxygenase inhibitor, a cytokine antagonist, an immunosuppressant, an anti-cancer agent, an anti-viral agent, a cytokine, a growth factor, an immunomodulator, a prostaglandin , an anti-vascular hyperproliferation compound, or an agent which increases the susceptibility of bacterial organisms to antibiotics.
23. A method of inhibiting gyrase activity in a biological sample or in a patient, comprising the step of contacting said biological sample with:
a) a composition according to claim 21; or b) a compound according to claim 1.
a) a composition according to claim 21; or b) a compound according to claim 1.
24. A method of inhibiting TopoIV activity in a biological sample or in a patient, comprising the step of contacting said biological sample with:
a) a composition according to claim 21; or b) a compound according to claim 1.
a) a composition according to claim 21; or b) a compound according to claim 1.
25. A method of inhibiting gyrase and TopoIV activity in a biological sample or in a patient, comprising the step of contacting said biological sample with:
a) a composition according to claim 21; or b) a compound according to claim 1.
a) a composition according to claim 21; or b) a compound according to claim 1.
26. A method of decreasing bacterial quantity in a patient, comprising the step of administering to said patient:
a) a composition according to claim 21; or b) a compound according to claim 1.
a) a composition according to claim 21; or b) a compound according to claim 1.
27. A method of treating, preventing, or lessening the severity of, a bacterial infection in a patient, comprising the step of administering to said patient:
a) a composition according to claim 21; or b) a compound according to claim 1.
a) a composition according to claim 21; or b) a compound according to claim 1.
28. The method according to claim 27, wherein the bacterial infection to be treated is characterized by the presence of one or more of the following:
Streptococcus pneumoniae, Streptococcus pyogenes, Enterococcus faecalis, Enterococcus faecium, Klebsiella pneunmoniae, Enterobacter sps. Proteus sps. Pseudomonas aeruginosa, E. coli, Serratia marcesens, Staphylococcus aureus, Coag. Neg. Staph, Haemophilus influenzae, Bacillus anthracis, Mycoplasma pneumoniae, Moraxella catarralis, Chlamydia pneumoniae, Legionella pneunophila, Staphylococcus epidermidis, Mycobacterium tuberculosis, or Helcoibacter pylori.
Streptococcus pneumoniae, Streptococcus pyogenes, Enterococcus faecalis, Enterococcus faecium, Klebsiella pneunmoniae, Enterobacter sps. Proteus sps. Pseudomonas aeruginosa, E. coli, Serratia marcesens, Staphylococcus aureus, Coag. Neg. Staph, Haemophilus influenzae, Bacillus anthracis, Mycoplasma pneumoniae, Moraxella catarralis, Chlamydia pneumoniae, Legionella pneunophila, Staphylococcus epidermidis, Mycobacterium tuberculosis, or Helcoibacter pylori.
29. The method according to claim 28, wherein the bacterial infection to be treated is selected from one or more of the following: a urinary tract infection, a respiratory infection, pneumonia, prostatitis, a skin or soft tissue infection, an intra-abdominal infection, a blood stream infection, or an infection of febrile neutropenic patients.
30. The method according to claim 29, further comprising the step of administering to said patient an additional therapeutic agent either as part of a multiple dosage form together with said compound or as a separate dosage form.
31. The method according to claim 28, further comprising the step of administering to said patient an agent that increases the susceptibility of bacterial organisms to antibiotics.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44391703P | 2003-01-31 | 2003-01-31 | |
| US60/443,917 | 2003-01-31 | ||
| PCT/US2004/002541 WO2005012292A1 (en) | 2003-01-31 | 2004-01-29 | Gyrase inhibitors and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2513463A1 true CA2513463A1 (en) | 2005-02-10 |
| CA2513463C CA2513463C (en) | 2012-07-10 |
Family
ID=34115255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2513463A Expired - Fee Related CA2513463C (en) | 2003-01-31 | 2004-01-29 | Gyrase inhibitors and uses thereof |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US7495014B2 (en) |
| EP (1) | EP1592686B1 (en) |
| JP (2) | JP4691033B2 (en) |
| KR (1) | KR20060056270A (en) |
| CN (1) | CN100393714C (en) |
| AR (1) | AR042956A1 (en) |
| AT (1) | ATE435859T1 (en) |
| AU (1) | AU2004261545B2 (en) |
| CA (1) | CA2513463C (en) |
| CY (1) | CY1109385T1 (en) |
| DE (1) | DE602004021904D1 (en) |
| DK (1) | DK1592686T3 (en) |
| ES (1) | ES2327642T3 (en) |
| HK (1) | HK1087699A1 (en) |
| IL (1) | IL169720A (en) |
| MX (1) | MXPA05008126A (en) |
| MY (1) | MY139124A (en) |
| NO (1) | NO20053845L (en) |
| NZ (1) | NZ541885A (en) |
| PT (1) | PT1592686E (en) |
| RU (1) | RU2350612C2 (en) |
| SI (1) | SI1592686T1 (en) |
| TW (1) | TWI334416B (en) |
| WO (1) | WO2005012292A1 (en) |
| ZA (1) | ZA200505773B (en) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101052433B1 (en) * | 2002-06-13 | 2011-07-29 | 버텍스 파마슈티칼스 인코포레이티드 | 2-ureido-6-heteroaryl-3H-benzoimidazole-4-carboxylic acid derivatives as gyrase and / or topoisomerase IV inhibitors and pharmaceutical compositions for treating bacterial infections comprising the same |
| AR042956A1 (en) | 2003-01-31 | 2005-07-13 | Vertex Pharma | GIRASA INHIBITORS AND USES OF THE SAME |
| US8193352B2 (en) | 2003-01-31 | 2012-06-05 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7582641B2 (en) | 2003-01-31 | 2009-09-01 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US8404852B2 (en) | 2003-01-31 | 2013-03-26 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7618974B2 (en) | 2003-01-31 | 2009-11-17 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US7569591B2 (en) * | 2003-01-31 | 2009-08-04 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| WO2006025978A2 (en) * | 2004-07-23 | 2006-03-09 | University Of Medicine And Dentistry Of New Jersey | Non-antibiotic intervention of chlamydial infection |
| CA2608116A1 (en) | 2005-05-10 | 2006-11-16 | Intermune, Inc. | Method of modulating stress-activated protein kinase system |
| DE102005028862A1 (en) * | 2005-06-22 | 2007-01-11 | Sanofi-Aventis Deutschland Gmbh | Substituted heterocycles, their use as medicament and pharmaceutical compositions containing them |
| AU2006311729A1 (en) * | 2005-11-07 | 2007-05-18 | Vertex Pharmaceuticals Incorporated | Benzimidazole derivatives as gyrase inhibitors |
| GB0724349D0 (en) * | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Antibacterial agents |
| US8481544B2 (en) | 2006-06-22 | 2013-07-09 | Biota Europe Limited | Antibacterial compositions |
| GB0612428D0 (en) * | 2006-06-22 | 2006-08-02 | Prolysis Ltd | Antibacterial agents |
| WO2009001915A1 (en) * | 2007-06-28 | 2008-12-31 | Takeda Pharmaceutical Company Limited | Substituted imidazole compound and use thereof |
| WO2009027733A1 (en) * | 2007-08-24 | 2009-03-05 | Astrazeneca Ab | (2-pyridin-3-ylimidazo[1,2-b]pyridazin-6-yl) urea derivatives as antibacterial agents |
| CA2708241A1 (en) * | 2007-12-07 | 2009-06-18 | Vertex Pharmaceuticals Incorporated | Solid forms of 1-ethyl-3-(5-(5-fluoropyridin-3-yl)-7-(pyrimidin-2-yl)-1h-benzo[d]imidazol-2-yl)urea |
| GB0724342D0 (en) | 2007-12-13 | 2008-01-30 | Prolysis Ltd | Anitbacterial compositions |
| JP5520831B2 (en) * | 2007-12-19 | 2014-06-11 | アムジエン・インコーポレーテツド | Inhibitors of PI3 kinase |
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