Claims
- 1. A 2-oxa-isocephem compound of the formula (1): ##STR173## wherein R.sup.1 is a hydrogen atom, an amino group, a lower alkanoylamino group, a halogen-substituted lower alkanoylamino group, a phenyl-substituted lower alkylamino group having 1 to 3 phenyl groups, a phenyl-lower alkoxycarbonylamino group or a lower alkoxycarbonylamino group; R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a tetrahydropyranyl group or a group of the formula:
- --A--R.sup.4
- (wherein A is a lower alkylene group, R.sup.4 is a cyano group, a carboxy group, a lower alkoxycarbonyl group, a halogen-substituted lower alkyl group, a lower alkylthio group, a thiazolyl group, an imidazolyl group, a cycloalkyl group, a phenyl group, a tetrahydrofuranyl group, an oxazolyl group, a 4-lower alkyl-2,3-dioxo-1-piperazinylcarbonyl group, a trityl-substituted or unsubstituted pyrazolyl group or a lower alkyl-substituted or unsubstituted pyridyl group); R.sup.3 is a hydrogen atom, a methyl group, a lower alkanoyloxymethyl group, a carbamoyloxymethyl group, a lower alkoxymethyl group, or an unsaturated heterocycle-thiomethyl group containing 1 to 4 hetero atoms selected from the group consisting of nitrogen and sulfur atoms; in which the heterocyclic moiety of said heterocycle-thiomethyl group may optionally have 1 to 3 substituents selected from the group consisting of lower alkyl, lower alkenyl, lower alkoxycarbonyl, carboxy, phenyl-lower alkoxycarbonyl-lower alkyl having 1 to 3 phenyl groups, carboxy-lower alkyl, hydroxy-lower alkyl, hydroxy, oxo, amino, carbamoyl, cyano, lower alkyl-substituted amino-lower alkyl, piperidinyl-lower alkyl, pyrrolidinyl-lower alkyl, carbamoyl-lower alkyl, and cyano-lower alkyl groups, or a 4-lower alkyl-1-piperazinyl-lower alkyl group; provided that when R.sup.1 is an amino group, a lower alkanoylamino group, a halogen-substituted lower alkanoylamino group, a phenyl-substituted lower alkyl amino group having 1 to 3 phenyl groups, a phenyl-lower alkoxycarbonylamino group or a lower alkoxycarbonylamino group and R.sup.3 is a hydrogen atom, a methyl group or a lower alkanoyloxymethyl group, R.sup.2 means a cyclo-lower alkyl group or a tetrahydropyranyl group or R.sup.4 means a cyano group, a cycloalkyl group, a tetrahydrofuranyl group or a 4-lower alkyl-2,3-dioxo-1-piperazinylcarbonyl group; and pharmaceutically acceptable salts thereof, esters of the carboxy group in the 4-position thereof and quaternary ammonium salts thereof.
- 2. A 2-oxa-isocephem compound as claimed in claim 1, wherein R.sup.1 is a hydrogen atom.
- 3. A 2-oxa-isocephem compound as claimed in claim 1, wherein R.sup.1 is an amino group.
- 4. A 2-oxa-isocephem compound as claimed in claim 1, wherein R.sup.1 is a lower alkanoylamino group, a halogen-substituted lower alkanoylamino group, a phenylsubstituted lower alkylamino group having 1 to 3 phenyl groups, a phenyl-lower alkoxycarbonylamino group or a lower alkoxycarbonylamino group.
- 5. A 2-oxa-isocephem compound as claimed in claim 3, wherein R.sup.3 is a hydrogen atom, a methyl group, a lower alkanoyloxymethyl group, a carbamoyloxymethyl group or a lower alkoxymethyl group.
- 6. A 2-oxa-isocephem compound as claimed in claim 3, wherein R.sup.3 is an unsaturated heterocycle-thiomethyl group containing 1 to 4 hetero atoms selected from the group consisting of nitrogen and sulfur atoms; in which the heterocyclic moiety of said heterocycle-thiomethyl methyl group may optionally have 1 to 3 substituents selected from the group consisting of lower alkyl, lower alkenyl, lower alkoxycarbonyl, carboxy, phenyl-lower alkoxycarbonyl-lower alkyl having 1 to 3 phenyl groups, carboxy-lower alkyl, hydroxy-lower alkyl, hydroxy, oxo, amino, carbamoyl, cyano, lower alkyl-substituted amino-lower alkyl, piperidinyl-lower alkyl, pyrrolidinyl-lower alkyl, carbamoyl-lower alkyl, and cyano-lower alkyl groups, or a 4-lower alkyl-1-piperazinyl-lower alkyl group.
- 7. A 2-oxa-isocephem compound as claimed in claim 6, wherein R.sup.2 is a lower alkyl group or a group of the formula: --A--R.sup.4, in which A has the same meaning as defined above, and R.sup.4 is a cyano group, a carboxy group or a lower alkoxycarbonyl group.
- 8. A 2-oxa-isocephem compound as claimed in claim 7, wherein the heterocyclic moiety of the heterocycle-thiomethyl group for R.sup.3 is a heterocyclic group selected from the group consisting of a 1,3,4-thiadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,4-triazolyl group, a 1,3,4-triazolyl group, a 1,2,3-triazolyl group, a tetrazolyl group, a pyridyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, an imidazolyl group, a 1,2,4-triazinyl group, a 5,6,7,8-tetrahydroquinolyl group, an .alpha.,.beta.-ethylenepyridyl group or a 6,7-dihydro-5H-pyrindinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 9. A 2-oxa-isocephem compound as claimed in claim 8, wherein the heterocyclic group is a pyridyl group, a 5,6,7,8-tetrahydroquinolyl group, an .alpha.,.beta.-ethylenepyridyl group or a 6,7-dihydro-5H-pyrindinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 10. A 2-oxa-isocephem compound as claimed in claim 8, wherein the heterocyclic group is a 1,3,4-thiadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,4-triazinyl group or a tetrazolyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 11. A 2-oxa-isocephem compound as claimed in claim 8, wherein the heterocyclic group is a 1,2,4-triazolyl group, a 1,3,4-triazolyl group, a 1,2,3-triazolyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group or an imidazolyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 12. A 2-oxa-isocephem compound as claimed in claim 9, wherein the heterocyclic group is a pyridyl group optionally having substituent(s) as defined in claim 6.
- 13. A 2-oxa-isocephem compound as claimed in claim 9, wherein the heterocyclic group is a 6,7-dihydro-5H-pyrindinyl group optionally having substituent(s) as defined in claim 6.
- 14. A 2-oxa-isocephem compound as claimed in claim 12, wherein the pyridyl group is a pyridyl group substituted, at the N atom thereof, with a lower alkyl group, a carboxy-lower alkyl group or a carbamoyl-lower alkyl group.
- 15. A 2-oxa-isocephem compound as claimed in claim 13, wherein the 6,7-dihydro-5H-pyrindinyl group is a 6,7-dihydro-5H-pyrindinyl group optionally substituted, at the N atom thereof, with a lower alkyl group or a carboxy-lower alkyl group.
- 16. 7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(1-methyl-4-pyridinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(1-carboxymethyl-4-pyridinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2cyanomethoxyiminoacetamido]-3-[(1-methyl-4-pyridinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-[(1-carboxymethyl-4-pyridinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-b 4-carboxylate (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(1-carbamoylmethyl-4-pyridinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4carboxylate (syn-isomer) or 7-[2-(2-aminothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-[(1-carbamoylmethyl-4pyridinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer), or optically active compounds thereof, or pharmaceutically acceptable salts thereof according to claim 14.
- 17. 7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[[1-methyl-6,7-dihydro-4-(5H-1pyrindinio)]thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(6,7-dihydro-5H-1-pyrindino-4-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3[[1-carboxymethyl-6,7-dihydro-4-(5H-1-pyrindino)]thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-cyanomethyloxyiminoacetamido)-3-[(6,7-dihydro-5H-1-pyrindin-4-yl)thiomethyl)-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer) or 7-[2-(2-aminothiazol-4-yl)-2-(2-carboxy-2-propoxyimino)acetamido]-3-[[1-methyl-6,7-dihydro-4-(5H-1pyrindino)]thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer), or optically active compounds thereof, or pharmaceutically acceptable salts thereof according to claim 15.
- 18.7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(1,3,4-thiadiazol-2-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3[(1,4,5,6-tetrahydro-4-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thiomethyl-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (synisomer), 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[[1-[2-(4-methyl-1-piperazinyl)ethyl]-1H-tetrazol-5-yl]thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer), or optically active compounds thereof, or pharmaceutically acceptable salts thereof according to claim 10.
- 19. A 2-oxa-isocephem compound as claimed in claim 6, wherein R.sup.2 is a cycloalkyl group or a group of the formula: --A--R.sup.4, in which A has the same meaning as defined above and R.sup.4 is a cycloalkyl group.
- 20. A 2-oxa-isocephem compound as claimed in claim 19, wherein the heterocyclic moiety of the heterocycle-thiomethyl group for R.sup.3 is a heterocyclic group selected from the group consisting of a 1,3,4-thiadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,4-triazolyl group, a 1,3,4-triazolyl group, a 1,2,3-triazolyl group, a tetrazolyl group, a pyridyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, an imidazolyl group, a 1,2,4-triazinyl group, a 5,6,7,8-tetrahydroquinolyl group, an .alpha.,.beta.-ethylenepyridyl group or a 6,7-dihydro-5H-pyrindinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 21. A 2-oxa-isocephem compound as claimed in claim 20, wherein the heterocyclic group is a pyridyl group, a 5,6,7,8-tetrahydroquinolyl group, an .alpha.,.beta.-ethylenepyridyl group or a 6,7-dihydro-5H-pyrindinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 22. A 2-oxa-isocephem compound as claimed in claim 20, wherein the heterocyclic group is a 1,2-thiazolyl group or a 1,3-thiazolyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 23. A 2-oxa-isocephem compound as claimed in claim 20, wherein the heterocyclic group is a 1,3,4-thiadiazolyl group, a 1,2,3-thiadiazolyl group or a 1,2,4-thiadiazolyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 24. A 2-oxa-isocephem compound as claimed in claim 20, wherein the heterocyclic group is a 1,3,4-triazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a tetrazolyl group, an imidazolyl group or a 1,2,4-triazinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 25. A 2-oxa-isocephem compound as claimed in claim 21, wherein the heterocyclic group is a pyridyl group optionally having substituent(s) as defined in claim 6.
- 26. A 2-oxa-isocephem compound as claimed in claim 21, wherein the heterocyclic group is a 6,7-dihydro-5H-pyrindinyl group optionally having substituent(s) as defined in claim 6.
- 27. A 2-oxa-isocephem compound as claimed in claim 22, wherein said thiazolyl groups are thiazolyl groups substituted with a lower alkyl group or a carboxy-lower alkyl group.
- 28. A 2-oxa-isocephem compound as claimed in claim 23, wherein said thiadiazolyl groups are thiadiazolyl groups optionally substituted with a carbamoyl group, a carboxy-lower alkyl group, a hydroxylower alkyl group, a cyano group or an amino group.
- 29. A 2-oxa-isocephem compound as claimed in claim 25, wherein the pyridyl group is pyridyl group substituted, at the N atom thereof, with a lower alkyl group or a carboxy-lower alkyl group.
- 30. A 2-oxa-isocephem compound as claimed in claim 26, wherein the 6,7-dihydro-5H-pyrindinyl group is a 6,7-dihydro-5H-pyrindinyl group substituted, at the N atom thereof, with a lower alkyl group.
- 31. 7-[2-(2-Aminothiazol-4-yl)-2-cyclopropylmethyloxyiminoacetamido]-3-[(1-carboxymethyl-4-pyridinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer) or 7-[2-(2-aminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-[(1-methyl-4-pyridinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer), or optically active compounds thereof, or pharmaceutically acceptable salts thereof according to claim 29.
- 32. 7-[2-(2-Aminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-[[1-methyl-6,7-dihydro-4-(5H-1pyrindinio)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate (syn-isomer) or its optically active compound, or a pharmaceutically acceptable salt thereof according to claim 30.
- 33.7-[2-(2-Aminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-[5-(carboxymethyl-4-methyl-1,3-thiazol-2-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer) or its optically active compound or a pharmaceutically acceptable salt thereof according to claim 27.
- 34.7-[2-(2-Aminothiazol-4-yl)-2-cyclopropylmethylloxyiminoacetamido]-3-[(1,3,4-thiadiazol-2-yl)thiomethyl]-.DELTA..sup.3 O-2-isocephem-4-carboxylic acid (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-[(1,3,4-thiadiazol-2-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer), 7-[2-(2-aminothiazol-4-yl)2-cyclohexyloxyiminoacetamido]-3[(1,3,4-thiadiazol-2-yl)-thiomethyl]-.DELTA..sup.-O- 2-isocephem-4carboxylic acid (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-cyclopentyloxy-iminoacetamido]-3-[(5-carbamoyl-1,3,4-thiadiazol-2-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-cyclopentyloxy-iminoacetamido]-3-[(5-carboxymethyl-1,3,4-thiadiazol-2-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-cyclopentyloxy-iminoacetamido]-3-[(5-amino-1,3,4-thiadiazol-2-yl)-thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4carboxylic acid (syn-isomer), 7-[2-(2-aminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-[(5-hydroxymethyl-1,3,4-thiadiazol-2-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer) or 7-[2-(2-aminothiazol-4-yl)-2-cyclopentyloxyiminoacetamido]-3-[(5-cyano-1,3,4-thiadiazol-2-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer), or optically active compounds thereof, or pharmaceutically acceptable salts thereof according to claim 28.
- 35. A 2-oxa-isocephem compound as claimed in claim 6, wherein R.sup.2 is a lower alkenyl group or a lower alkynyl group.
- 36. A 2-oxa-isocephem compound as claimed in claim 35, wherein the heterocyclic moiety of the heterocycle-thiomethyl group for R.sup.3 is a heterocyclic group selected from the group consisting of a 1,3,4-thiadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,4-triazolyl group, a 1,3,4-triazolyl group, a 1,2,3-triazolyl group, a tetrazolyl group, a pyridyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, an imidazolyl group, a 1,2,4-triazinyl group, a 5,6,7,8-tetrahydroquinolyl group, an .alpha.,.beta.-ethylenepyridyl group or a 6,7-dihydro-5H-pyrindinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 37. A 2-oxa-isocephem compound as claimed in claim 36, wherein the heterocyclic group is a 5,6,7,8-tetrahydroquinolyl group, an .alpha.,.beta.-ethylenepyridyl group or a 6,7-dihydro-5H-pyrindinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 38. A 2-oxa-isocephem compound as claimed in claim 36, wherein the heterocyclic group is a 1,3,4-thiadiazolyl group, a 1,2,3-thiadiazolyl group or a 1,2,4-thiadiazolyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 39. A 2-oxa-isocephem compound as claimed in claim 36, wherein the heterocyclic group is a 1,2-thiazolyl group, a 1,3-thiazolyl group or a tetrazolyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 40. A 2-oxa-isocephem compound as claimed in claim 36, wherein the heterocyclic group is a 1,3,4-triazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl, a pyridyl group, an imidazolyl group or a 1,2,4-triazinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 41. 7-[2-(2-Aminothiazol-4-yl)-2-allyloxyiminoacetamido]-3-[(1,3,4-thiadiazol-2-yl)thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylic acid (syn-isomer) or its optionally active active compound, or a pharmaceutically acceptable salt thereof according to claim 38.
- 42. A 2-oxa-isocephem compound as claimed in claim 6, wherein R2 is a hydrogen atom, a tetrahydropyranyl group or a group of the formula: --A--R.sup.4, in which A has the same meaning as defined above, and R.sup.4 is a halogen-substituted lower alkyl group, a lower alkylthio group, a thiazoly group, an imidazolyl group, a phenyl group, a tetrahydrofuranyl group, an oxazolyl group, a 4-lower alkyl-2,3-dioxo-1-piperazinylcarbonyl group, a trityl-substituted or unsubstituted pyrazolyl group, or a lower alkyl-substituted or unsubstituted pyridyl group; and the heterocyclic moiety of the heterocycle-thiomethyl group for R.sup.3 is a heterocyclic group selected from the group consisting of a 1,3,4-thiadiazolyl group, a 1,2,3-thiadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,2,4-triazolyl group, a 1,3,4-triazolyl group, a 1,2,3-triazolyl group, a tetrazolyl group, a pyridyl group, a 1,2-thiazolyl group, a 1,3-thiazolyl group, an imidazolyl group, a 1,2,4-triazinyl group, a 5,6,7,8-tetrahydroquinolyl group, an .alpha.,.beta.-ethylenepyridyl group or a 6,7-dihydro-5H-pyrindinyl group, in which these heterocyclic groups may optionally have substituent(s) as defined in claim 6.
- 43. A 2-oxa-isocephem compound as claimed in claim 14, wherein the pyridyl group is a pyridyl group substituted, at the N atom thereof, with a carbamoyl-lower alkyl group, and R.sup.2 is an isopropyl group.
- 44. A 2-oxa-isocephem compound as claimed in claim 43, wherein the carbamoyl-lower alkyl group is a carbamoylmethyl group.
- 45. A 2-oxa-isocephem compound as claimed in claim 14, wherein the pyridyl group is a pyridyl group substituted, at the N atom thereof, with a lower alkyl group, and R.sup.4 is a carboxy group.
- 46. A 2-oxa-isocephem compound as claimed claim 45, wherein A is a methylmethylene group or an ethylene group.
- 47. (6S,7S)-7-[2-(2-Aminothiazal-4-yl)-2-cyclopentyloxyaminoacetamido]-3-[[1-(2-hydroxyethyl)-4-pyridinio]thiomethyl]-.DELTA..sup.3 -O-2-isocephem-4-carboxylate(syn-isomer) or a pharmaceutically acceptable salt thereof according to claim 25.
- 48. An antimicrobial composition comprising a antimicrobial composition comprising a antimicrobially effective amount of a 2-oxa-isocephem compound of the formula (1): ##STR174## wherein R.sup.1 is a hydrogen atom, an amino group, a lower alkanoylamino group, a halogen-substituted lower alkanoylamino group, a phenyl-substituted lower alkyl-amino group having 1 to 3 phenyl groups, a phenyl-lower alkoxycarbonylamino group or a lower alkoxycarbonylamino group; R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, a tetrahydropyranyl group or a group of the formula:
- --A--R.sup.4
- (wherein A is a lower alkylene group, R.sup.4 is a cyano group, a carboxy group, a lower alkoxycarbonyl group, a halogen-substituted lower alkyl group, a lower alkylthio group, a thiazolyl group, an imidazolyl group, a cycloalkyl group, a phenyl group, a tetrahydrofuranyl group, an oxazolyl group, a 4-lower alkyl-2,3-dioxo-1-piperazinylcarbonyl group, a trityl-substituted or unsubstituted pyrazolyl group or a lower alkyl-substituted or unsubstituted pyridyl group); R.sup.3 is a hydrogen atom, a methyl group, a lower alkanoyloxymethyl group, a carbamoyloxymethyl group, a lower alkoxymethyl group, or an unsaturated heterocycle-thiomethyl group containing 1 to 4 hetero atoms selected from the group consisting of nitrogen and sulfur atoms; in which the heterocyclic moiety of said heterocycle-thiomethyl group may optionally have 1 to 3 substituents selected from the group consisting of lower alkyl, lower alkenyl, lower alkoxycarbonyl, carboxy, phenyl-lower alkoxycarbonyllower alkyl having 1 to 3 phenyl groups, carboxy-lower alkyl, hydroxy-lower alkyl, hydroxy, oxo, amino, carbamoyl, cyano, lower alkyl-substituted amino-lower alkyl, piperidinyl-lower alkyl, pyrrolidinyl-lower alkyl, carbamoyl-lower alkyl, and cyano-lower alkyl groups, or a 4-lower alkyl-1-piperazinyl-lower alkyl group; provided that when R.sup.1 is an amino group, a lower alkanoylamino group, a halogen-substituted lower alkanoylamino group, a phenyl-substituted lower alkyl amino group having 1 to 3 phenyl groups, a phenyl-lower alkoxycarbonylamino group or a lower alkoxycarbonylamino group and R.sup.3 is a hydrogen atom, a methyl group or a lower alkanoyloxy-methyl group, R.sup.2 means a cyclo-lower alkyl group or a tetrahydropyranyl group or R.sup.4 means a cyano group, a cycloalkyl group, a tetrahydrofuranyl group or a 4-lower alkyl-2,3-dioxo-1-piperazinylcarbonyl group; pharmaceutically acceptable salts thereof, esters of the carboxy group in the 4-position thereof and quaternary ammonium salts thereof, and a pharmaceutically acceptable carrier.
- 49. A method for treatment of diseases caused by pathogenic bacteria which comprises administering a 2-oxa-isocephem compound of claim 1 to human being and animals.
Priority Claims (6)
Number |
Date |
Country |
Kind |
60-199044 |
Sep 1985 |
JPX |
|
60-285031 |
Dec 1985 |
JPX |
|
61-34412 |
Feb 1986 |
JPX |
|
61-77229 |
Apr 1986 |
JPX |
|
61-132976 |
Jun 1986 |
JPX |
|
61-167134 |
Jul 1986 |
JPX |
|
Parent Case Info
This application is a continuation-in-part application of Ser. No. 905,205, filed Sept. 9, 1986, now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4013648 |
Horning et al. |
Mar 1977 |
|
4386089 |
Konig et al. |
May 1983 |
|
4476124 |
Heymes et al. |
Oct 1984 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
905205 |
Sep 1986 |
|