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Details for Patent: 7,638,529

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Details for Patent: 7,638,529

Title:Heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-bacterial agents
Abstract: The invention relates to new heterocyclic compounds of general formula (I), and their salts with a base or an acid: ##STR00001## The invention also relates to a process for the preparation of these compounds as well as their use as medicaments, in particular as anti-bacterial agents.
Inventor(s): Lampilas; Maxime (Romainville, FR), Aszodi; Jozsef (Tucson, AZ), Rowlands; David Alan (Poissy, FR), Fromentin; Claude (Paris, FR)
Assignee: Aventis Pharma S.A. (Antony, FR)
Filing Date:Sep 14, 2005
Application Number:11/226,749
Claims:1. A compound of general formula, or one of its salts with a base or an acid: ##STR00013## R.sub.1 is selected from the group consisting of hydrogen, --COOH, --CN, --COOR, --CONR.sub.6, R.sub.7, --(CH.sub.2).sub.n'R.sub.5 and ##STR00014## R is selected from the group consisting of alkyl of 1 to 6 carbon atoms optionally substituted by a member selected from the group consisting of pyridyl and carbamoyl, --CH.sub.2-alkenyl of 3 to 9 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl of 7 to 11 carbon atoms, the ring of the aryl or aralkyl unsubstituted or substituted by a member selected from the group consisting of --OH, --NH.sub.2, --NO.sub.2, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and one halogen, R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, an aryl of 1 to 6 carbon atoms and aralkyl of 7 to 11 carbon atoms, unsubstituted or substituted by a member selected from the group consisting of carbamoyl, ureido and dimethylamino, and alkyl of 1 to 6 carbon atoms substituted by pyridyl, n' is equal to 1 or 2, R.sub.5 is selected from the group consisting of a --COOH, --CN, --OH, --NH.sub.2, --CO--NR.sub.6R.sub.7, --COOR, --OR, --OCOH, --OCOR, --OCOOR, --OCONHR, --OCONH.sub.2, --NHR, --NHCOH, --NHCOR, --NHSO.sub.2R, --NH--COOR, --NH--CO--NHR and --NHCONH.sub.2, R, R.sub.6 and R.sub.7 being as defined above; R.sub.2 is hydrogen or --(CH.sub.2).sub.n'1R.sub.5 , n'.sub.1 being equal to 0, 1 or 2 and R.sub.5 being as defined above; R.sub.3 is hydrogen or alkyl of 1 to 6 carbon atoms; A represents a bond between the two carbon carriers of R.sub.1 and R.sub.2 n is 1; X is --C(O)--B-- attached to the nitrogen atom by the carbon atom, B is --O--(CH.sub.2).sub.n''-- attached to the carbonyl by the oxygen, or --NR.sub.8--(CH.sub.2).sub.n''-- or --NR.sub.8--O-- attached to the carbonyl by the nitrogen, n'' is equal to 0 and R.sub.8 is selected from the group consisting of hydrogen, --OH, --R, --OR, --Y, --OY, --Y.sub.1, --OY.sub.1, --Y.sub.2, --OY.sub.2, --Y.sub.3, --OCH.sub.2CH.sub.2SO.sub.mR, --OSiR.sub.aR.sub.bR.sub.c and SiR.sub.aR.sub.bR.sub.c, R.sub.a, R.sub.b and R.sub.c are individually alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms, R being as defined above and m being equal to 0, 1 or 2; Y is selected from the group consisting of --COH, --COR, --COOR, --CONH.sub.2, --CONHR, --CONHOH, --CONHSO.sub.2R, --CH.sub.2COOH, --CH.sub.2COOR, --CH.sub.2CONHOH, --CH.sub.2CONHCN, --CH.sub.2tetrazole, --CH.sub.2SO.sub.3H, --CH.sub.2SO.sub.2R, --CH.sub.2PO(OR).sub.2, --CH.sub.2PO(OR)(OH), --CH.sub.2PO(R)(OH) and --CH.sub.2PO(OH).sub.2, Y.sub.1 is selected from the group consisting of the --SO.sub.2R, --SO.sub.2NHCOH, --SO.sub.2NHCOR, --SO.sub.2NHCOOR, --SO.sub.2NHCONHR, --SO.sub.2NHCONH.sub.2 and --SO.sub.3H, Y.sub.2 is selected from the group consisting of --PO(OH).sub.2, --PO(OR).sub.2, --PO(OH) (OR) and --PO(OH)R, Y.sub.3 is selected from the group consisting of tetrazole, tetrazole substituted by R, squarate, --NH or --NR tetrazole, --NH and --NR tetrazole substituted by R, --NRSO.sub.2R and --NRSO.sub.2R, R being as defined above.

2. A compound of claim 1, wherein X is --CO--B in which B is --NR.sub.8--(CH.sub.2).sub.n''.

3. A compound of claim 1, wherein --R.sub.8 is --Y.sub.1 or --OY.sub.1 , in which Y.sub.1 is selected from the group consisting of --SO.sub.2R, --SO.sub.2NHCOR, --SO.sub.2NHCOOR, --SO.sub.2NHCONHR, --SO.sub.3H and R is as defined in claim 1.

4. A compound of claim 1, wherein R.sub.1 is --CONR.sub.6,R.sub.7.

5. A compound of claim 1, wherein R.sub.2 is H.

6. A compound of claim 1, wherein R.sub.3 is H.

7. A compound of the formula, or one of its salts with a base or an acid: ##STR00015## wherein R.sub.1 is selected from the group consisting of hydrogen, --COOH, --CN, --COOR, --CONR.sub.6,R.sub.7, --(CH.sub.2).sub.n'R.sub.5 and ##STR00016## R is selected from the group consisting of alkyl of 1 to 6 carbon atoms, optionally substituted by pyridyl or carbamoyl, --CH.sub.2-alkenyl of 3 to 9 carbon atoms, aryl of 6 to 10 carbon atoms or aralkyl of 7 to 11 carbon atoms, the ring of the aryl or aralkyl unsubstituted or substituted by a member selected from the group consisting of --OH, --NH.sub.2, --NO.sub.2, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, and by at least one halogen, R.sub.6 and R.sub.7 individually, are selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl of 7 to 11 carbon atoms, unsubstituted or substituted by a member selected from the group consisting of carbamoyl, ureido, and dimethylamino, and alkyl of 1 to 6 carbon atoms substituted by a pyridyl, n' is equal to 1 or 2, R.sub.5 is selected from the group consisting of --COOH, --CN, --OH, --NH.sub.2, --CO--NR.sub.6R.sub.7, --COOR, --OR, --OCOH, --OCOR, --OCOOR, --OCONHR, --OCONH.sub.2, --NHR, --NHCOH, --NHCOR, --NHSO.sub.2R, --NH--COOR, --NH--CO--NHR and --NHCONH.sub.2, R, R.sub.6 and R.sub.7 being as defined above; R.sub.2 is hydrogen or --(CH.sub.2).sub.n'1R.sub.5 , n'.sub.1 being equal to 0, 1 or 2 and R.sub.5 being as defined above; R.sub.3 is hydrogen or alkyl of 1 to 6 carbon atoms; A represents a bond between the two carbon carriers of R.sub.1 and R.sub.2; n is 1; X is --C(O)--B-- attached to the nitrogen by the carbon, B is --NR.sub.8--(CH.sub.2).sub.n''-- attached to the carbonyl by the nitrogen, n'' is equal to 0 or 1 and R.sub.8 is selected from the group consisting of hydrogen, --OH, --R, --OR, --Y, --OY, --Y.sub.1, --OY.sub.1, --Y.sub.2,--OY.sub.2, --Y.sub.3, --OCH.sub.2CH.sub.2SO.sub.mR, --OSiR.sub.aR.sub.bR.sub.c and SiR.sub.aR.sub.bR.sub.c, R.sub.a, R.sub.b and R.sub.c are individually alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms, R being as defined above and m being equal to 0, 1 or 2; Y is selected from the group consisting of --COH, --COR, --COOR, --CONH.sub.2, --CONHR, --CONHOH, --CONHSO.sub.2R, --CH.sub.2COOH, --CH.sub.2COOR, --CH.sub.2CONHOH, --CH.sub.2CONHCN, --CH.sub.2tetrazole, --CH.sub.2SO.sub.3H, --CH.sub.2SO.sub.2R, --CH.sub.2PO(OR).sub.2, --CH.sub.2PO(OR)(OH), --CH.sub.2PO(R)(OH) and --CH.sub.2PO(OH).sub.2 , Y.sub.1 is selected from the group consisting of --O.sub.2R, --SO.sub.2NHCOH, --SO.sub.2NHCOR, --SO.sub.2NHCOOR, --SO.sub.2NHCONHR, --SO.sub.2NHCONH.sub.2 and --SO.sub.3H, Y.sub.2 is selected from the group consisting of --PO(OH).sub.2, --PO(OR).sub.2, --PO(OH)(OR) and --PO(OH)(R), Y.sub.3 is selected from the group consisting of tetrazole, tetrazole substituted by R, squarate, --NH or --NR tetrazole, --NH, --NR tetrazole substituted by R, --NRSO.sub.2R and --NRSO.sub.2R, R being as defined above.

8. A compound of claim 7, wherein in group B, --R.sub.8 is --Y.sub.1 or --OY.sub.1 , in which --Y.sub.1 is selected from the group consisting of --SO.sub.2R, --SO.sub.2NHCOR, --SO.sub.2NHCOOR, --SO.sub.2NHCONHR, and --SO.sub.3H wherein R is as defined in claim 7.

9. A compound of claim 7, wherein R.sub.1 is --CONR.sub.6,R.sub.7.

10. A compound of claim 7, wherein R.sub.2 is H.

11. A compound of claim 7, wherein R.sub.3 is H.

12. A compound of the formula, or one of its salts with a base or an acid: ##STR00017## wherein R.sub.1 is --CONR.sub.6R.sub.7; R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl of 7 to 11 carbon atoms, unsubstituted or substituted on the phenyl by a member selected from the group consisting of carbamoyl, ureido and dimethylamino and alkyl of 1 to 6 carbon atoms substituted by pyridyl, R.sub.2 is hydrogen; R.sub.3 is hydrogen; A is a bond between the two carbon carriers of R.sub.1 and R.sub.2, R.sub.4 is hydrogen, or --(CH.sub.2).sub.n'1R.sub.5 , n'.sub.1 is equal to 1 or 2 and R.sub.5 is selected from the group consisting of --COOH, --CN, --OH, --NH.sub.2, --CO--NR.sub.6R.sub.7, --COOR, --OR, --OCOH, --OCOR, --OCOOR, --OCONHR, --OCONH.sub.2, --NHR, --NHCOH, --NHSO.sub.2R, --NH--COOR, --NH--CO--NHR and --NHCONH.sub.2; R is selected from the group consisting of alkyl 1 to 6 carbon atoms, optionally substituted by a pyridyl or carbamoyl, --CH.sub.2-alkenyl of 3 to 9 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl of 7 to 11 carbon atoms, the ring of the aryl or aralkyl unsubstituted or substituted by a member selected from the group consisting of --OH, --NH.sub.2, --NO.sub.2, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and at least one halogen, R.sub.6 and R.sub.7 being as defined above, n is 1; X is --C(O)--B-- attached to the nitrogen by the carbon, B is --NR.sub.8--(CH.sub.2).sub.n'' attached to the carbonyl by the nitrogen, n'' is 1 and R.sub.8 is selected from the group consisting of hydrogen, --OH, --R, --OR, --Y, --OY, --Y.sub.1, --OY.sub.1, --Y.sub.2, --OY.sub.2, --Y.sub.3, --OCH.sub.2CH.sub.2SO.sub.mR, --OSiR.sub.aR.sub.bR.sub.c and SiR.sub.aR.sub.bR.sub.c , R.sub.a, R.sub.b and R.sub.c are individually alkyl of 1 to 6 carbon atoms or aryl of 6 to 10 carbon atoms, R being as defined above and m being equal to 0, 1 or 2; Y is selected from the group consisting of --COH, --COR, --COOR, --CONH.sub.2, --CONHR, --CONHOH, --CONSO.sub.2R, --CH.sub.2COOH, --CH.sub.2COOR, --CH.sub.2CONHOH, --CH.sub.2CONHCN, --CH.sub.2tetrazole, --CH.sub.2SO.sub.3H, --CH.sub.2SO.sub.2R, --CH.sub.2PO(OR).sub.2, --CH.sub.2PO(OR)(OH), --CH.sub.2PO(R)(OH) and --CH.sub.2PO(OH).sub.2, Y.sub.1 is selected from the group consisting of --SO.sub.2R, --SO.sub.2NHCOH, --SO.sub.2NHCOR, --SO.sub.2NHCOOR, --SO.sub.2NHCONHR, --SO.sub.2NHCONH.sub.2 and --SO.sub.3H, Y.sub.2 is selected from the group consisting of --PO(OH).sub.2, --PO(OR).sub.2, --PO(OH)(OR) and --PO(OH)(R), Y.sub.3 is selected from the group consisting of tetrazole, tetrazole substituted by the R, squarate, --NH or --NR tetrazole, --NH, --NR tetrazole substituted by R, --NHSO.sub.2R and --NRSO.sub.2R, R being as defined above.

13. A compound of claim 12, wherein in group B --R.sub.8 is --Y.sub.1 or --OY.sub.1 , in which --Y.sub.1 is selected from the group consisting of --SO.sub.2R, --SO.sub.2NHCOR, --SO.sub.2NHCOOR, --SO.sub.2NHCONHR, and --SO.sub.3H wherein R is as defined in claim 12.

14. A pharmaceutical compositions comprising, as active ingredient, at least one product of claim 1 and a pharmaceutical acceptable carrier.

15. A pharmaceutical composition comprising, as active ingredient, at least one product of claim 7 and a pharmaceutical acceptable carrier.

16. A pharmaceutical composition comprising, as active ingredient, at least one product of claim 12 and a pharmaceutical acceptable carrier.

17. A method of treating bacterial infections in warm-blooded animals comprising administering to warm-blooded animals in need thereof a antibacterially effective amount of a compound of claim 1.

18. A compound of claim 1 selected from the group consisting of 3-benzoyl-1,3-diazabicyclo[2,2,1]heptan-2-one, methyl trans-3-benzoyl-2-oxo-1,3-diazabicyclo[2,2,1]heptane-6-carboxylate, phenylmethyl trans-2-oxo-3-(phenylsulfonyl)-1,3-diaza bicyclo[2,2,1]heptane-6-carboxylate, phenylmethyl trans-3-benzoyl-4-methyl-2-oxo-1,3-diaza-bicyclo[2,2,1]heptane-6-carboxyl- ate, 1-propenyltriphenyiphosphonium salt of phenylmethyl trans-2-oxo-3-(sulfooxy)-1,3-diazabicyclo[2,2,1]heptane-6-carboxylate, 1-propenyltriphenyiphosphonium salt of methyl trans-2-oxo-3-(sulfooxy)-1,3,diazabicyclo[2,2,1]heptane-6-carboxylate and phenylmethyl trans-3-benzoyl-2-oxo-4-oxa-1,3-diazabicyclo[3,2,1]octane-7-carboxylate.

19. A pharmaceutical composition comprising, as active ingredient, at least one product of claim 18 and a pharmaceutical acceptable carrier.
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