Bicyclic compounds and their use as antibacterial agents and β-lactamase inhibitors
A compound of formula (I): wherein: M is hydrogen or a pharmaceutically acceptable salt-forming cation; and R 1 and M are as defined herein. Also, methods of treating bacterial infection, pharmaceutical compositions, molecular complexes and processes for preparing compounds.
1. A compound of formula (I):
wherein:
M is hydrogen or a pharmaceutically acceptable salt-forming cation;
R 1 is a radical selected from the group consisting of:
(1) C 1-6 straight or branched chain alkyl which is optionally substituted; and
(2) C 3-7 cycloalkyl which is optionally substituted;
or a deuterated compound of any such compound.
2. A compound as recited in claim 1 , wherein R 1 is optionally substituted with one or two substituents independently selected from the following: lower alkyl, amino, substituted amino, amidino, and guanidino.
3. A compound as recited in claim 1 , which is selected from the following group of compounds:
and pharmaceutically acceptable salts of such compounds, and deuterated compounds of such compounds and salts.
4. A compound of formula (I) as defined in claim 1 , wherein the compound is selected from the group consisting of:
(2S,5R)—N-(2-aminoethoxy)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)—N-[(2-aminocyclopropyl)oxy]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)—N-[(2-(methylamino)ethoxy]-7-oxo-6-(sulfoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)—N-(3-aminopropoxy)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)—N-[3-(methylamino)propoxy]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)—N-[(2S)-2-aminopropoxy]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)—N-[(2R)-2-aminopropoxy]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)—N-[(2-aminocyclobutyl)oxy]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)—N-[(2-aminocyclopentyl)oxy]-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
or a deuterated compound of any such compound.
5. A pharmaceutical composition containing as an active ingredient, at least one compound as recited in claim 1 .
6. A molecular complex comprising a compound as recited claim 1 and at least one solvent.
7. A molecular complex as recited in claim 6 , wherein the solvent comprises water.
8. A compound of the following formula:
and pharmaceutically acceptable salts thereof, and deuterated compounds thereof and salts.
9. (2S,5R)—N-(2-aminoethoxy)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide or a deuterated compound thereof.
10. A pharmaceutical composition containing as an active ingredient, the compound of claim 8 .
11. A pharmaceutical composition containing as an active ingredient, the compound of claim 9 .
12. A molecular complex comprising the compound of claim 8 and at least one solvent.
13. The molecular complex as recited in claim 12 , wherein the solvent comprises water.
14. A molecular complex comprising the compound of claim 9 and at least one solvent.
15. The molecular complex as recited in claim 14 , wherein the solvent comprises water.