FR2285134A1 - 7-(2-(4-hydroxy-3-nitrophenyl)-2-aminoacetamido)-cephalosporins - with broad-spectrum antibacterial activity - Google Patents

7-(2-(4-hydroxy-3-nitrophenyl)-2-aminoacetamido)-cephalosporins - with broad-spectrum antibacterial activity

Info

Publication number
FR2285134A1
FR2285134A1 FR7528486A FR7528486A FR2285134A1 FR 2285134 A1 FR2285134 A1 FR 2285134A1 FR 7528486 A FR7528486 A FR 7528486A FR 7528486 A FR7528486 A FR 7528486A FR 2285134 A1 FR2285134 A1 FR 2285134A1
Authority
FR
France
Prior art keywords
formula
het
thiadiazol
converting
aminoacetamido
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7528486A
Other languages
French (fr)
Other versions
FR2285134B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19742444762 external-priority patent/DE2444762A1/en
Priority claimed from DE19752529425 external-priority patent/DE2529425A1/en
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of FR2285134A1 publication Critical patent/FR2285134A1/en
Application granted granted Critical
Publication of FR2285134B1 publication Critical patent/FR2285134B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

Cephalosporin cpds. of formula (I): (where R1 is H or CHO; R2 is H, Cl, Br or NO2; R3 is H, OCOMe or S-Het; Het is 1,3,4-thiadiazol-2-yl, 5-methyl-1,3,4-thiadiazol-2-yl, 3-methyl-1,2,4-thiadiazol-5-yl, 1-methyltetrazol-5-yl or 1,2,3-triazol-5-yl), esters and salts, are prepd. by reacting a 3-CH2R3-7-amino-3-cephem-4-carboxylic acid of formula (II): or a functional deriv. with a substd. phenylacetic acid of formula (III): or an activated deriv. (in the form of an acid addn. salt when R1 = H) or by treating a cpd. corresp. to formula (I) but contg. a functionally modified OH or NH2 gp. with a solvolysing or hydrogenolysing agent, and opt. converting R3 = OCOMe into R3 = S-Het-by reaction with Het-SH, and/or converting R1 = H into R1 = CHO by reaction with a formylating agent, and/or converting COOH into an ester or salt or vice versa, and/or isolating a pure epimer from an epimer mixt. of formula (I). (I) are antibacterial agents active against Gram-positive and -negative bacteria.
FR7528486A 1974-09-19 1975-09-17 7-(2-(4-hydroxy-3-nitrophenyl)-2-aminoacetamido)-cephalosporins - with broad-spectrum antibacterial activity Granted FR2285134A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19742444762 DE2444762A1 (en) 1974-09-19 1974-09-19 7-(2-(4-hydroxy-3-nitrophenyl)-2-aminoacetamido)-cephalosporins - with broad-spectrum antibacterial activity
DE19752529425 DE2529425A1 (en) 1975-07-02 1975-07-02 7-(2-(4-hydroxy-3-nitrophenyl)-2-aminoacetamido)-cephalosporins - with broad-spectrum antibacterial activity

Publications (2)

Publication Number Publication Date
FR2285134A1 true FR2285134A1 (en) 1976-04-16
FR2285134B1 FR2285134B1 (en) 1978-11-10

Family

ID=25767722

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7528486A Granted FR2285134A1 (en) 1974-09-19 1975-09-17 7-(2-(4-hydroxy-3-nitrophenyl)-2-aminoacetamido)-cephalosporins - with broad-spectrum antibacterial activity

Country Status (8)

Country Link
JP (1) JPS5156493A (en)
DD (1) DD121946A5 (en)
DK (1) DK420275A (en)
FR (1) FR2285134A1 (en)
IL (1) IL48090A0 (en)
LU (1) LU73421A1 (en)
NL (1) NL7511091A (en)
SE (1) SE7510464L (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0121499A2 (en) * 1983-03-31 1984-10-10 Ciba-Geigy Ag Cephalosporins, their preparation and pharmaceutical compositions
EP0171812A2 (en) * 1984-08-16 1986-02-19 Sumitomo Pharmaceuticals Company, Limited Cephem derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5346995A (en) * 1976-10-12 1978-04-27 Sangyo Kagaku Kenkyu Kyokai Antibacterial agents

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2118012A1 (en) * 1970-12-17 1972-07-28 Smith Kline French Lab
FR2228476A1 (en) * 1973-05-10 1974-12-06 Fujisawa Pharmaceutical Co

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2118012A1 (en) * 1970-12-17 1972-07-28 Smith Kline French Lab
FR2228476A1 (en) * 1973-05-10 1974-12-06 Fujisawa Pharmaceutical Co

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0121499A2 (en) * 1983-03-31 1984-10-10 Ciba-Geigy Ag Cephalosporins, their preparation and pharmaceutical compositions
EP0121499A3 (en) * 1983-03-31 1985-09-25 Ciba-Geigy Ag Cephalosporins, their preparation and pharmaceutical compositions
EP0171812A2 (en) * 1984-08-16 1986-02-19 Sumitomo Pharmaceuticals Company, Limited Cephem derivatives
EP0171812A3 (en) * 1984-08-16 1987-04-29 Sumitomo Pharmaceuticals Company, Limited Cephem derivatives
US4761409A (en) * 1984-08-16 1988-08-02 Sumitomo Pharmaceuticals Company, Limited Cephem derivatives

Also Published As

Publication number Publication date
IL48090A0 (en) 1975-11-25
JPS5156493A (en) 1976-05-18
NL7511091A (en) 1976-03-23
DK420275A (en) 1976-03-20
DD121946A5 (en) 1976-09-05
FR2285134B1 (en) 1978-11-10
SE7510464L (en) 1976-03-22
LU73421A1 (en) 1977-05-16

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