EP0203271A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Antibacterial compounds, their production and use
Assignee: Takeda Pharmaceutical Co Ltd
•
Filing: 1986-02-27
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Granted: —
•
Expires: 2006-02-27
Abstract
Abstract A compound of the formula; wherein R 1 is an amino group which may be protected, R 3 is a hydrogen atom or an optionally substituted hydrocarbon residue; Z is S, S → O, O or CH 2 , R 4 is a hydrogen atom, methoxy group or formamido group, R 13 is a hydrogen atom, methyl group, hydroxyl group or halogen atom and A⊕ is an optionally substituted imidazolium-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a pharmaceutically acceptable salt or ester thereof 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
2026-11-03 09:44
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/02; C07D277/20; C07D277/587; A; A61; A61P; A61P31/00; A61P31/04; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/08; C07D463/00; C07D463/10; C07D463/14; C07D463/16; C07D463/18; C07D463/20; C07D463/22; C07D471/00; C07D471/02; C07D471/04; C07D487/00; C07D487/02; C07D487/04; C07D505/00
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
86 words
. 1. A compound of the formula; I wherein R 1 is an amino group which may be protected, R 3 is hydrogen atom or an optionally substituted hydrocarbon residue; Z is S, S → O, O or CH2, R 4 is hydrogen atom, methoxy group or formamido group, R 13 is hydrogen atom, methyl group, hydroxyl group or halogen atom and A⊕ is an optionally substituted imidazolium-1-yl group forming a condensed ring at the 2,3- or 3,4-position, or a pharmaceutically acceptable salt or ester thereof.
Claim 2
Dependent Claim
48 words
The compound according to claim 1 wherein the optionally substituted hydrocarbon residue is C 1-3 alkyl group which may be substituted by halogen atom, hydroxyl group, C 1-6 alkoxy group, carboxyl group, C 1-6 alkoxycarbonyl group or cyano group, the number of the substituents being one to three.
Claim 3
Dependent Claim
22 words
The compound according to claim 1 wherein Z is S ; R 4 is hydrogen atom; and R 13 is hydrogen atom.
Claim 4
Dependent Claim
34 words
The compound according to claim 1, wherein A⊕ is an imidazo[1,5-a]pyridinium-2-yl group which is substituted by C 1-6 alkyl group, halogen atom or cyano group, the number of the substituents being one to two.
Claim 5
Dependent Claim
37 words
The compound according to claim 1, wherein R 1 is amino group; R 3 is C 1-3 alkyl group which may be substituted; and A is an imidazo[1,2-a]pyridinium-1-yl group which is substituted by fluorine or cyano group.
Claim 6
Dependent Claim
29 words
The compound according to claim 1 wherein A⊕ is an optionally substituted imidazolium-1-yl group having at the 2,3-or 3,4-position a 5 to 6 membered aromatic heterocyclic ring condensed herewith.
Claim 7
Dependent Claim
22 words
The compound according to claim 1 wherein A⊕ is an imid--- azo/ 1,2-a]pyridinium-1-yl, imidazo/ 1,5-a]pyridinium-2-yl or imidazol[1,2-b]pyridazinium-1-yl group, which may be substituted.
Claim 8
Dependent Claim
68 words
The compound according to claim 1 wherein R 1 is amino group, R 3 is C 1-3 alkyl group optionally substituted by halogen atom, hydroxy group, C 1-6 alkoxy group, carboxyl group, C 1-6 alkoxy-carbonyl group or cyano group, Z is S , R 4 is hydrogen atom, R 13 is hydrogen atom and A+ is an imidazo-[1,2-a]pyridinium-1-yl, imidazo/ l,5-a_/pyridinium-2-yl or imidazo/ 1,2-b]pyridazinium-1-yl group which may be substituted.
Claim 9
Dependent Claim
49 words
The compound according to claim 1, wherein A⊕ is an imidazo[1,2-b]pyridazinium-1-yl group which may be substituted by C 1-6 alkyl, halogen, C 1-6 alkox y , di-C 1-6 alkylamino di-C 1-6 alkylamino-C 1-6 alk y lthio, or C 1-6 alkylthio, the number of the substituents being one to two.
Claim 10
Dependent Claim
34 words
The compound according to claim 1, wherein A⊕ is an imidazo[1,2-a]pyridinium-1-yl group which may be substituted by halogen, cyano, or di-C 1-6 alkylamino-C 1-6 alkyl, the number of the substituents being one to two.
Claim 11
Dependent Claim
33 words
The compound according to claim 1 wherein R 3 is C 1-3 alkyl group which may be substituted by carboxyl group or cyano group, the number of the substituents being one to three.
Claim 12
Dependent Claim
53 words
The compounds according to claim 1, selected from 7B-/ 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido]-3-[(imidazo[1,2-b]pyridazinium-1-yl)methyl-]-3-cephem-4-carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacet- amido-]-3-[(imidazo[1,2-b]pyridazinium-1-yl)methyl-]-3-cephem-4-carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido]-3-[(7-methylimidazo[1,2-b]pyridazinium-1-yl)-methyl]-3-cephem-4-carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido]-3-[(6-chloroimidazo[1,2-b]pyridazinium-1-yl)methyl]-3-cephem-4-carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido]-3-[(6-methoxyimidazo[1,2-b]pyridazinium-1-yl]-3-cephem-4-carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido-]-3-[(6-dimethylaminoimidazo[1,2-b]pyridazinium-1-yl)methyl] -3-cephem-4-carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-carboxymethoxy- iminoacetamido]-3-[(imidazo[1,2-b]pyridazinium-1-yl)methyl] - 3-cephem-4-carboxylate mono-sodium salt; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido]-3-[(6-(2-dimethylaminoethylthio)imidazo[1,2-b]pyri- dazinium-1-yl)methyl]-3-cephem-4-carboxylate dihydrochloride; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido-]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-Cephem-4- carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacet- amido]-3-[(imidazo[1,2-]pyridinium-1-yl)methyl] -3-Cephem-4- carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacet- amido)-3-[(6-chloroimidazol[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacet- amido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)methyl]-.. 3-cephem-4-carboxylate; 7B-/ 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-carboxymethoxy- iminoacetamido]-3-[(6-cyanoimidazo[1,2-a]pyridinium-1-yl)-methyl]-3-cephem-4-carboxylate and; 7ß-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacet- amido]-3-[-(6-methylthioimidazo[1,2-b]pyridazinium-1-y]-3-cephem-4-carboxylate dihydrochloride.
Claim 13
Independent Claim
245 words
A method for producing a compound of the formula; wherein R 1 is an amino group which may be protected, R 3 is hydrogen atom or an optionally substituted hydrocarbon residue; Z is S, S - O, O or CH 2 , R 4 is hydrogen atom, methoxy group or formamido group, R 13 is hydrogen atom, methyl group, hydroxyl group or halogen atom and A⊕ is an optionally substituted imidazolium-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a pharmaceutically acceptable salt or ester thereof, which comprises (1) reacting a compound of the formula: I wherein the symbols are of the same meaning as defined above or a salt or ester thereof with carboxylic acid of the formula: or a salt or reactive derivative thereof, or (2) reacting a compound of the formula; wherein R 5 is 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 with an imidazole compound of the formula A' (A' means an optionally substituted imidazole forming a condensed ring at the 2,3- or 3,4-position) or a salt thereof, or (3) reacting a compound of the formula: wherein the symbols are of the same meaning as defined above or a salt or ester thereof with a compound of the formula R 3 " OH wherein R3" is an optionally substituted hydrocarbon residue, or a reactive derivative thereof.
Claim 14
Dependent Claim
93 words
A pharmaceutical composition containing at least one of the compounds of the formula: wherein R 1 is an amino group which may be protected, R 3 is hydrogen atom or an optionally substituted hydrocarbon residue; Z is S, S → O, O or CH 2 , R 4 is hydrogen atom, methoxy group or formamido group, R 13 is hydrogen atom, methyl group, hydroxyl group or halogen atom and A⊕ is an optionally substituted imidazolium-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a pharmaceutically acceptable salt or ester thereof.
Claim 15
Dependent Claim
14 words
Applicant has found some clerial errors in the English Text as per enclosed CORRIGENDA.
Claim 16
Dependent Claim
30 words
New pages 54, 124, and 125 are herewith enclosed in triplicate and - if possible - it is respectfully requested to perform these corrections before the application is laid open.
Claim 17
Dependent Claim
1 words
Corrigenda
Claim 18
Dependent Claim
17 words
(1) (c.f. the present English text, page 54, formula [X]and Claim 13, the 4th formula) error correct
Claim 19
Dependent Claim
13 words
(2) (c.f. the present English text, Claim 12, line 1 from the bottom)
Claim 20
Dependent Claim
2 words
error 3-[[6-methylthioimidazo[1,2-b]pyridazinium-1-yl]-
Claim 21
Dependent Claim
4 words
correct 3- [(6-methylthioimidazo [1,2-b]pyridazinium-1-yl)methyl]-
References Cited (Backward Citations)
No citation records indexed.
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