FR2368491A1 - Antibiotic (7)-thiazolyl-acetamido-(3)-acylthiomethyl cephalosporins - active against Gram positive and negative organisms, e.g. penicillin-resistant Staphylococci - Google Patents
Antibiotic (7)-thiazolyl-acetamido-(3)-acylthiomethyl cephalosporins - active against Gram positive and negative organisms, e.g. penicillin-resistant StaphylococciInfo
- Publication number
- FR2368491A1 FR2368491A1 FR7714711A FR7714711A FR2368491A1 FR 2368491 A1 FR2368491 A1 FR 2368491A1 FR 7714711 A FR7714711 A FR 7714711A FR 7714711 A FR7714711 A FR 7714711A FR 2368491 A1 FR2368491 A1 FR 2368491A1
- Authority
- FR
- France
- Prior art keywords
- cephalosporins
- acetamido
- thiazolyl
- penicillin
- against gram
- 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
Links
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229930182555 Penicillin Natural products 0.000 title abstract 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 title abstract 2
- 241000295644 Staphylococcaceae Species 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 150000001780 cephalosporins Chemical class 0.000 title abstract 2
- 229940049954 penicillin Drugs 0.000 title abstract 2
- 230000003115 biocidal effect Effects 0.000 title 1
- RDCQFQMETSVKLD-JLOHTSLTSA-N (6R)-3-(acetylsulfanylmethyl)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)CC(=O)NC1[C@@H]2N(C(=C(CS2)CSC(C)=O)C(=O)O)C1=O RDCQFQMETSVKLD-JLOHTSLTSA-N 0.000 abstract 1
- 241000193738 Bacillus anthracis Species 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 201000004813 Bronchopneumonia Diseases 0.000 abstract 1
- 241000588748 Klebsiella Species 0.000 abstract 1
- 208000032376 Lung infection Diseases 0.000 abstract 1
- 241000588769 Proteus <enterobacteria> Species 0.000 abstract 1
- 206010056430 Staphylococcal sepsis Diseases 0.000 abstract 1
- 206010052428 Wound Diseases 0.000 abstract 1
- 208000027418 Wounds and injury Diseases 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000003211 malignant effect Effects 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- 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
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Cephalosporins of formula (I) are new: where R is H or a gp. easily removed by acid hydrolysis or hydrogenolysis. R1 is 1-4C alkyl or a 5-membered heterocycle opt. contg. a ketonic group; A is H or an equiv. of alkali(ne earth) metal or Mg or an amine base. (I) are antibiotics with good activity against Gram +ve and -ve organisms, including streptococci, penicillin-resistant staphylococci, coliform bacteria, Proteus spp. and Klebsiella spp. Admin. may be by oral, rectal, parenteral or topical routes, at e.g. 0.25-4g per day p.o. or e.g. 0.5-1g 3 times per day i.n. (I) are useful for treating staphylococcal septicaemia, malignant staphylococcal conditions of teh skin and face, pyodermitis, septic or suppurating wounds or sores, anthrax, bronchopneumonia, pulmonary suppurations, etc. Specifically claimed (I) is 7-(2-(2-amino-4-thiazolyl)-acetamido)-3-(acetylthiomethyl)-ceph-3- -em-4-carboxylic acid).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7714711A FR2368491A1 (en) | 1977-05-13 | 1977-05-13 | Antibiotic (7)-thiazolyl-acetamido-(3)-acylthiomethyl cephalosporins - active against Gram positive and negative organisms, e.g. penicillin-resistant Staphylococci |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7714711A FR2368491A1 (en) | 1977-05-13 | 1977-05-13 | Antibiotic (7)-thiazolyl-acetamido-(3)-acylthiomethyl cephalosporins - active against Gram positive and negative organisms, e.g. penicillin-resistant Staphylococci |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2368491A1 true FR2368491A1 (en) | 1978-05-19 |
| FR2368491B1 FR2368491B1 (en) | 1980-03-07 |
Family
ID=9190782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7714711A Granted FR2368491A1 (en) | 1977-05-13 | 1977-05-13 | Antibiotic (7)-thiazolyl-acetamido-(3)-acylthiomethyl cephalosporins - active against Gram positive and negative organisms, e.g. penicillin-resistant Staphylococci |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2368491A1 (en) |
-
1977
- 1977-05-13 FR FR7714711A patent/FR2368491A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2368491B1 (en) | 1980-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |