Patent EP0164113A2 successfully refreshed from Google Patents.
EP0164113A2
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EP
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3-pyrazolo(1,5-a)pyridinium cephem compounds, their production and use
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1985-06-05
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Granted: —
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Expires: 2005-06-05
Abstract
Abstract A compound of the formula; Wherein R 0 stands for hydrogen atom, nitrogencontaining heterocyclic group, acyl group or aminoprotecting group, Z stands for S, S→O, 0 or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof. This compound is novel and has excellent antibacterial activity.
Inventors
- 👤 Akio Miyake
- 👤 Masahiro Kondo
- 👤 Masahiko Fujino
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-01 09:53
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07D501/38; C07D501/46; C07D519/00; C07D463/00; C07D463/10; C07D463/14; C07D463/16; C07D463/18; C07D463/20; C07D463/22; C07D505/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
82 words
A compound of the formula; wherein R O stands for hydrogen atom, nitrogen- containing heterocyclic group, acyl group or amino- protecting group, Z stands for S, S→O, 0 or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted Pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof.
Claim 2
Dependent Claim
82 words
A compound of the formula; wherein R O stands for hydrogen atom, nitrogen- containing heterocyclic group, acyl group or amino- protecting group, Z stands for S, S→O, 0 or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted Pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof.
Claim 3
Dependent Claim
22 words
A compound according to claim 1 wherein R is a 5 to 8 membered nitrogen- containing heterocylic group which may be substituted.
Claim 4
Dependent Claim
28 words
A compound according to claim 1 wherein R 0 is alkanoyl group, alkenoyl group, cycloalkyl- carbonyl group, cycloalkenyl-carbonyl group, aryl-carbonyl group or heterocycle-carbonyl group which may be substituted.
Claim 5
Dependent Claim
120 words
A compound according to claim 3 wherein the alkanoyl group is a group of the formula in which R 22 denotes C 3-10 cycloalkyl* group, C 5-6 cycloalkenyl* group, C 6-10 aryl* group, C 1-6 alkoxy group, C 6-10 aryl*oxy group, C 1-6 alkyl*thio group, amino C 1-6 alkylthio group, C 6-10 aryl*thio group, C 7-19 aralkyl*thio group, cyano group, acyl + group, carbamoyl group or heterocyclic* group and R 21 denotes OR 23 group wherein R 23 is hydrogen atom or optionally substituted hydrocarbon residue, wherein acyl + group denotes C 1-6 alkanoyl group, C 6-10 aryl*carbonyl group, C 7-19 aralkyl*carbonyl group, heterocycle*carbonyl group or heterocycle * acetyl group and the group bearing asterisk * denotes optionally substituted group.
Claim 6
Dependent Claim
41 words
A compound according to claim 4 wherein R 22 denotes a 5 to 8 membered heterocyclic group which may be substituted with C 1-6 alkyl group, hydroxyl group, amino group or halogen atom and the configuration of R 21 is syn.
Claim 7
Dependent Claim
26 words
A compound according to claim 5 wherein the heterocyclic group is a group of the formula in which R 2 denotes hydrogen atom or halogen atom.
Claim 8
Dependent Claim
47 words
A compound according to claim 4 wherein the optionally substituted hydrocarbon residue is C 1-3 alkyl group which may be substituted with halogen atom, hydroxyl group, C l-6 alkoxy group, carboxyl group, C 1-6 alkoxy-carbonyl group or cyano group and the configuration of R 21 is syn.
Claim 9
Dependent Claim
28 words
A compound according to claim 1 wherein R 0 is C 1-10 alkoxy-carbonyl group, C 6-10 aryloxy- carbonyl group or C 7-19 aralkyloxy-carbonyl group which may be substituted.
Claim 10
Dependent Claim
10 words
A compound according to claim 1 wherein Z is S.
Claim 11
Dependent Claim
12 words
A compound according to claim 1 wherein R 4 is hydrogen atom.
Claim 12
Dependent Claim
12 words
A compound according to claim 1 wherein R 13 is hydrogen atom.
Claim 13
Dependent Claim
28 words
A compound according to claim 1 wherein A is an optionally substituted pyrazol-2-yl group having at the 1,5-position a 5 to 6 membered aromatic heterocyclic ring fused herewith.
Claim 14
Dependent Claim
15 words
A compound according to claim 1 wherein A is pyrazolo[1,5-a]pyridinium-3-yl group which may be substituted.
Claim 15
Dependent Claim
72 words
A compound according to claim 1 wherein R 0 is a group of the formula; in which R 2 denotes hydrogen atom or halogen atom, R 23 denotes C 1-3 alkyl group optionally substituted with halogen atom, hydroxyl group, C 1-6 alkoxy group, carboxyl group, C 1-6 alkoxy-carbonyl group or cyano group, Z is S, R is hydrogen atom, R 13 is hydrogen atom and A is an optionally substituted pyrazolo[1,5-a]pyridinium-3-yl group.
Claim 16
Dependent Claim
9 words
A compound according to claim 1, namely 7β-[2-(2-amino- thiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(pyrazolo[1,5-a]pyridinium-3-yl]methyl]-3-cephem-4-carboxylate.
Claim 17
Dependent Claim
9 words
A compound according to claim 1, namely 7β-[2-(2-amino- thiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(7-methylpyrazolo[1,5-a]pyridinium-3-yl)methyl]-3-cephem-4-carboxylate.
Claim 18
Dependent Claim
9 words
A compound according to claim 1, namely 7β-[2-(2-amino- thiazol-4-yl)-2(Z)-(1-carboxy-1-methylethoxyimino)acetamido]-3-[(pyrazolo[1,5-a]pyridinium-3-yl)methyl]-3-cephem-4-carboxylate.
Claim 19
Dependent Claim
10 words
A compound according to claim 1, namely 7β-[2-(2-amino- thiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(7-carboxypyrazolo [1,5-a]pyridinium-3-yl)methyl]-3-cephem-4-carboxylate.
Claim 20
Dependent Claim
8 words
A compound according to claim 1, namely 7β-[2-(2-amino-5-chlorothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(pyrazolo[1,5-a]pyridinium-3-yl)methyl]-3-cephem-4-carboxylate.
Claim 21
Dependent Claim
8 words
A compound according to claim 1, namely 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacetamido]-3-[(pyrazolo[1,5-a]pyridinium-3-yl)methyl]-3-cephem-4-carboxylate.
Claim 22
Dependent Claim
10 words
A compound according to claim 1, namely 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[( py razolo-[l,5-a]pyridinium-3-yl)methyl]-3-cephem-4-carboxylate.
Claim 23
Independent Claim
130 words
A method for producing a compound of the formula; wherein Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted Pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted pyrazole forming a fused ring at the 1,5-position or a salt thereof.
Claim 24
Independent Claim
130 words
A method for producing a compound of the formula; wherein Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted Pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted pyrazole forming a fused ring at the 1,5-position or a salt thereof.
Claim 25
Independent Claim
195 words
A method for producing a compound of the formula; wherein R stands for nitrogen-containing heterocyclic group, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted Pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises (1) allowing a compound of the formula; wherein the symbols are of the same meaning as defined above or a salt or ester thereof to react with a compound of the general formula R a H al wherein R a stands for a nitrogen-containing heterocyclic group and Hal stands for a halogen atom or a salt thereof, or (2) allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted pyrazole forming a fused ring at the 1,5-position or a salt thereof.
Claim 26
Independent Claim
195 words
A method for producing a compound of the formula; wherein R stands for nitrogen-containing heterocyclic group, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted Pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises (1) allowing a compound of the formula; wherein the symbols are of the same meaning as defined above or a salt or ester thereof to react with a compound of the general formula R a H al wherein R a stands for a nitrogen-containing heterocyclic group and Hal stands for a halogen atom or a salt thereof, or (2) allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted pyrazole forming a fused ring at the 1,5-position or a salt thereof.
Claim 27
Independent Claim
188 words
A method for producing a compound of the formula; wherein R b stands for acyl group, Z stands for S, S→O, O or CH2, R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted p yrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or p harma- ceutically acceptable salt or ester thereof, which comprises (1) allowing a compound of the formula; wherein the symbols are of the same meaning as defined above or a salt or ester thereof to react with carboxylic acid of the general formula R b OH wherein R stands for acyl group or a salt or reactive derivative thereof, or (2) allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted pyrazole forming a fused ring at the 1,5-position or a salt thereof.
Claim 28
Independent Claim
188 words
A method for producing a compound of the formula; wherein R b stands for acyl group, Z stands for S, S→O, O or CH2, R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted p yrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or p harma- ceutically acceptable salt or ester thereof, which comprises (1) allowing a compound of the formula; wherein the symbols are of the same meaning as defined above or a salt or ester thereof to react with carboxylic acid of the general formula R b OH wherein R stands for acyl group or a salt or reactive derivative thereof, or (2) allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted pyrazole forming a fused ring at the 1,5-position or a salt thereof.
Claim 29
Independent Claim
141 words
A method for producing a compound of the formula; wherein R 221 stands for an optionally substituted heterocyclic group, R 3 " stands for optionally substituted hydrocarbon residue, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester .thereof, which comprises allowing a compound of the formula; wherein the symbols are of the same meaning as defined above or a salt or ester thereof to react with a compound of the general formula R 3 " OH wherein R 3 " stands for optionally substituted hydrocarbon residue or a reactive derivative thereof.
Claim 30
Independent Claim
141 words
A method for producing a compound of the formula; wherein R 221 stands for an optionally substituted heterocyclic group, R 3 " stands for optionally substituted hydrocarbon residue, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester .thereof, which comprises allowing a compound of the formula; wherein the symbols are of the same meaning as defined above or a salt or ester thereof to react with a compound of the general formula R 3 " OH wherein R 3 " stands for optionally substituted hydrocarbon residue or a reactive derivative thereof.
Claim 31
Independent Claim
151 words
A method for producing a compound of the formula; wherein R 1 stands for optionally protected amino group, R 2 stands for hydrogen atom, halogen atom or nitro group, R 3 stands for hydrogen atom or optionally substituted hydrocarbon residue, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises allowing a compound of the formula; wherein X stands for halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with a compound of the general formula R 1 C(=S)NH 2 wherein R1 stands for optionally protected amino group.
Claim 32
Independent Claim
151 words
A method for producing a compound of the formula; wherein R 1 stands for optionally protected amino group, R 2 stands for hydrogen atom, halogen atom or nitro group, R 3 stands for hydrogen atom or optionally substituted hydrocarbon residue, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises allowing a compound of the formula; wherein X stands for halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with a compound of the general formula R 1 C(=S)NH 2 wherein R1 stands for optionally protected amino group.
Claim 33
Independent Claim
168 words
A method for producing a compound of the formula; wherein R c stands for amino-protecting group, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises (1) allowing a compound of the formula; wherein the symbols are of the same meaning as defined above or a salt or ester thereof to react with an amino-protecting reagent, or (2) allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted pyrazole forming a fused ring at the 1,5-position or a salt thereof.
Claim 34
Independent Claim
168 words
A method for producing a compound of the formula; wherein R c stands for amino-protecting group, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof, which comprises (1) allowing a compound of the formula; wherein the symbols are of the same meaning as defined above or a salt or ester thereof to react with an amino-protecting reagent, or (2) allowing a compound of the formula; wherein R 5 stands for hydroxyl group, acyloxy group, carbamoyloxy group, substituted carbamoyloxy group or halogen atom and other symbols are of the same meaning as defined above or a salt or ester thereof to react with an optionally substituted pyrazole forming a fused ring at the 1,5-position or a salt thereof.
Claim 35
Dependent Claim
96 words
A pharmaceutical composition produced by mixing at least one of the cephem compounds of the formula; wherein R stands for hydrogen atom, nitrogen containing heterocyclic group, acyl group or amino-protecting group, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or physiologically or pharmaceutically acceptable salts or esters thereof and pharmaceutically acceptable carriers or excipients.
Claim 36
Dependent Claim
96 words
A pharmaceutical composition produced by mixing at least one of the cephem compounds of the formula; wherein R stands for hydrogen atom, nitrogen containing heterocyclic group, acyl group or amino-protecting group, Z stands for S, S→O, O or CH 2 , R 4 stands for hydrogen atom, methoxy group or formamido group, R 13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or physiologically or pharmaceutically acceptable salts or esters thereof and pharmaceutically acceptable carriers or excipients.
References Cited (Backward Citations)
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