Patent EP0062328A2 successfully refreshed from Google Patents.
EP0062328A2
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Novel penicillin and cephalosporin compounds, a process for preparing the same and antibacterial composition containing the novel compounds
Assignee: Eisai Co Ltd
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Filing: 1982-04-02
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Granted: —
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Expires: 2002-04-02
Abstract
Abstract A compound represented by the formula: wherein R, is hydrogen or methoxy; R 2 is hydrogen or hydroxy; R is wherein R 3 and R 4 are hydroxy or acyloxy, Y is oxygen, sulfur or N-R 5 wherein R 5 is hydrogen or lower alkyl, and Z is sulfur or N-R 5 wherein R 5 has the same meanings as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing hetero- cyclicthio which may have substituent(s), a pharmaceutically acceptable salt thereof, and a carboxylic ester thereof, a process for preparing the same and antibacterial composition containing the novel compounds. This compound has improved antibacterial activity against Kleb. pneumoniae and Pseid. aeruginosa.
Inventors
- 👤 Yoshimasa Machida
- 👤 Isao Saito
- 👤 Isao Sugiyama
- 👤 Shigeto Negi
- 👤 Seiichiro Nomoto
- 👤 Hironori Ikuta
- 👤 Hiroshi Yamauchi
- 👤 Kyosuke Kitoh
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 14:44
CPC Classifications
C; C07; C07D; C07D335/00; C07D335/04; C07D335/06; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56; C07D311/00; C07D311/02; C07D311/04; C07D311/06; C07D311/08; C07D311/16; C07D499/00
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
88 words
A compound represented by the formula: wherein R 1 is hydrogen or methoxy; R 2 is hydrogen or hydroxy; R is wherein R 3 and R 4 are hydroxy or acyloxy, Y is oxygen, sulfur or =N-R 5 wherein R 5 is hydrogen or lower alkyl, and Z is sulfur or =N-R 5 wherein R 5 has the same meanings as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing heterocyclic-thio which may have substituent(s), a pharmaceutically acceptable salt thereof, and a carboxylic ester thereof.
Claim 2
Dependent Claim
88 words
A compound represented by the formula: wherein R 1 is hydrogen or methoxy; R 2 is hydrogen or hydroxy; R is wherein R 3 and R 4 are hydroxy or acyloxy, Y is oxygen, sulfur or =N-R 5 wherein R 5 is hydrogen or lower alkyl, and Z is sulfur or =N-R 5 wherein R 5 has the same meanings as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing heterocyclic-thio which may have substituent(s), a pharmaceutically acceptable salt thereof, and a carboxylic ester thereof.
Claim 3
Dependent Claim
84 words
A compound according to claim 1, wherein R 6 is selected from the group consisting of pyrrolyl, pyridyl and N-oxide thereof, imidazolyl, pyrazolyl, pyrimidinyl, pyridazinyl, lH-1,2,4-triazolyl, 4H-1,2,4-triazolyl, 1H-1,2,3-triazolyl, 2H-1,2,3-triazolyl, 1H-tetrazolyl, 2H-tetrazolyl, thiazolyl, 1,2,3-thiazolyl, 1,2,4-thiazolyl, 1,3,4-thiadiazolyl, oxazolyl, 1,3, 1 1-oxadiazolyl, 1,2,5-oxadiazolyl, morpholino, benzothiazolyl, and benzoxazolyl, which may be unsubstituted or substituted by alkyl group such as methyl,ethyl, propyl and isopropyl; amino group; alkylaminoalkyl group such as dimethylaminoethyl, dimethylaminomethyl and diethylaminoethyl; carboxyalkyl group such as carboxymethyl and carboxyethyl; and sulfoalkyl group such as sulfomethyl and sulfoethyl.
Claim 4
Dependent Claim
15 words
A compound according to claim 1 whrein both R 3 and R 4 are hydroxy.
Claim 5
Dependent Claim
19 words
A compound according to claim 3, wherein said compound is 7β-[D-2-(6,7-dihydroxy-1-ethyl-1,4-dihydro-4- oxoquinoline-3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-3-[5-methyl-2-(1,3,4-thiadiazolyl]thiomethyl-3-cephem-4- carobxylic acid or pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
17 words
A compound according to claim 3, wherein said compound is 7β-[D-2-(6,7-dihydroxy-4-oxo-4H-1-benzothiopyran-3-caroxamide)-2-(4-hydroxyphenyl)acetamide]-3-(1-methyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid or pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
16 words
A compound according to claim 3, wherein said compound is 7β-[D-2-(6,7-dihydroxy-4-oxo-4H-1-benzothiopyran-3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-3-(1-carboxymethyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid or pharmaceutically acceptable thereof.
Claim 8
Dependent Claim
17 words
A compound accordipg to claim 3, wherein said compound is 6β-[D-2-(6,7-dihydroxy-2-oxo-2H-1-benzopyran-3-caroxamide)-2-phenyl-acetamiaejpemcitlamc acia or pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
17 words
A compound according to claim 3, wherein said compound is bβ-[D-2-(6,7-dihydroxy-2-oxo-2H-1-benzopyran-3-carboxamide)-2-(4-hydroxyphenyl)acetamide]penicillanic acid or pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
17 words
A compound according to claim 3, wherein said compound is 7β-[D-2-(6,7-dihydroxy-2-oxo-2H-1-benzopyran-3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-3-(1-carboxymethyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid or pharmeceutically acceptable salt thereof.
Claim 11
Dependent Claim
18 words
A compound according to calim 3, wherein said compound is 7β-CD-2-(7,8-dihydroxy-2-oxo-2H-1-benzopyran 3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-3-acetoxymethyl-3-cephem-4-carboxylic acid or pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
18 words
A compound according to calim 3, wherein said compound is 7β-CD-2-(7,8-dihydroxy-2-oxo-2H-1-benzopyran 3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-3-acetoxymethyl-3-cephem-4-carboxylic acid or pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
17 words
A compound according to claim 3, wherein said compound is 7p-[D-2-(7,8-dihydroxy-2-oxo-2H-1-benzopyran-3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-7α-methoxy-3-acetoxymethyl-3-cephem-4-carboylic acid or pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
17 words
A compound accroding to claim 3, wherein said compound is 7p-[D-(7,8-dihydroxy-2-oxo-2H-1-benzyopyran-3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-3-(1-carboxymethyl-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid or pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
19 words
A compound according to claim 3, wherein said compound is 7β-[D-2-(6,7-dihydroxy-2-oxo-2H-1-benzothiopyran _ 3-carboxamide)-2-(tl-hydroxyphenyl)acetamide]-3-(1-carboxymethyl)-5-tetrazolyl)thiomethyl-3-cephem-4-carboxylic acid or oharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
17 words
A compound according to calim 3, wherein said compound is 7β-[D-2-(6,7-dihydroxy-1,2-dihydro--2-oxoquinoline-3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-3-[5-methvl-2-(1,3,4-thiadiazolyl)]thiomethyl-3-cephem-4-carboxylic acid or pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
17 words
A compound according to calim 3, wherein said compound is 7β-[D-2-(6,7-dihydroxy-1,2-dihydro--2-oxoquinoline-3-carboxamide)-2-(4-hydroxyphenyl)acetamide]-3-[5-methvl-2-(1,3,4-thiadiazolyl)]thiomethyl-3-cephem-4-carboxylic acid or pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
152 words
A process for preparing a compound represented by the formula: wherein R 1 s hydrogen or methoxy, R 2 is hydrogen or.hydroxy; . R is wherein R 3 and R 4 are hydroxy or acyloxy, Y is oxygen, sulfur or =N-R5 wherein R 5 is hydrogen or lower alkyl, and Z is sulfur or = N-R5 wherein R 5 has the same meanings as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing heterocyclic-thio which may have substituent(s), a pharmaceutically acceptable salt thereof, or acarboxylic ester thereof which comprises reacting a compound represented by the formula: wherein R 1 , R 2 and X have the same meanings as defined above, a salt thereof or a hydrate thereof with a compound represented by the formula: wherein R has the same meanings as defined above or a - reactive derivative thereof, and if desired, followed by salt formation or esterification.
Claim 19
Dependent Claim
152 words
A process for preparing a compound represented by the formula: wherein R 1 s hydrogen or methoxy, R 2 is hydrogen or.hydroxy; . R is wherein R 3 and R 4 are hydroxy or acyloxy, Y is oxygen, sulfur or =N-R5 wherein R 5 is hydrogen or lower alkyl, and Z is sulfur or = N-R5 wherein R 5 has the same meanings as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing heterocyclic-thio which may have substituent(s), a pharmaceutically acceptable salt thereof, or acarboxylic ester thereof which comprises reacting a compound represented by the formula: wherein R 1 , R 2 and X have the same meanings as defined above, a salt thereof or a hydrate thereof with a compound represented by the formula: wherein R has the same meanings as defined above or a - reactive derivative thereof, and if desired, followed by salt formation or esterification.
Claim 20
Dependent Claim
136 words
A process. for preparing a compound represented by the formula: wherein R 1 is hydrogen or methyl; R 2 is hydrogen or hydroxy; and Y is oxygen, sulfur or = N-R5 wherein R 5 is hydrogen or lower alkyl, and Z is sulfur or = N-0R 5 wherein R 5 has the same meanings as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing heterocyclic-.. thio which may have substituent(s), a pharmaceutically . acceptable salt thereof, or a carboxylic ester thereof, which comprises hydrolyzing a compound represented by the formula: or wherein R 1 , R 2 , X, Y and Z have the same meanings as defined above, R 3 ' and R 4 ' are acyloxy, in the presence of a base, and if desired, followed by salt formation or esterification.
Claim 21
Dependent Claim
136 words
A process. for preparing a compound represented by the formula: wherein R 1 is hydrogen or methyl; R 2 is hydrogen or hydroxy; and Y is oxygen, sulfur or = N-R5 wherein R 5 is hydrogen or lower alkyl, and Z is sulfur or = N-0R 5 wherein R 5 has the same meanings as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing heterocyclic-.. thio which may have substituent(s), a pharmaceutically . acceptable salt thereof, or a carboxylic ester thereof, which comprises hydrolyzing a compound represented by the formula: or wherein R 1 , R 2 , X, Y and Z have the same meanings as defined above, R 3 ' and R 4 ' are acyloxy, in the presence of a base, and if desired, followed by salt formation or esterification.
Claim 22
Dependent Claim
105 words
An antibacterial composition which comprises an antibacterially effective amount of a compound represented by the formula: wherein R 1 is hydrogen or methoxy; R 2 is hydrogen or hydroxy; R is wherein R 3 and R 4 are hydroxy or acyloxy, Y is oxygen, sulfur or N-R5 wherein R 5 is hydrogen or lower alkyl, and Z is . sulfur or N-R5 wherein R 5 has the same meaning as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing heterocyclic-thio which may have substituent(s),. a pharmaceutically acceptable salt thereof, or a carboxylic ester thereof and a pharmaceutically acceptable carrier therefor.
Claim 23
Dependent Claim
105 words
An antibacterial composition which comprises an antibacterially effective amount of a compound represented by the formula: wherein R 1 is hydrogen or methoxy; R 2 is hydrogen or hydroxy; R is wherein R 3 and R 4 are hydroxy or acyloxy, Y is oxygen, sulfur or N-R5 wherein R 5 is hydrogen or lower alkyl, and Z is . sulfur or N-R5 wherein R 5 has the same meaning as defined above; and X is wherein R 6 is acyloxy or nitrogen-containing heterocyclic-thio which may have substituent(s),. a pharmaceutically acceptable salt thereof, or a carboxylic ester thereof and a pharmaceutically acceptable carrier therefor.
References Cited (Backward Citations)
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