GB1030630A - Antibacterial derivatives of 7-aminocephalosporanic acid - Google Patents
Antibacterial derivatives of 7-aminocephalosporanic acidInfo
- Publication number
- GB1030630A GB1030630A GB5512065A GB5512065A GB1030630A GB 1030630 A GB1030630 A GB 1030630A GB 5512065 A GB5512065 A GB 5512065A GB 5512065 A GB5512065 A GB 5512065A GB 1030630 A GB1030630 A GB 1030630A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbamoyl
- compound
- compounds
- formula
- alkyl
- 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.)
- Expired
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
- 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Derivatives of 7-aminocephalosporanic acid have the formula <FORM:1030630/C2/1> where Z is C1-6 alkyl, carbamoyl (excepting a single carbamoyl group in 4-position), N-mono-C1-6-alkyl carbamoyl (excepting a single methylcarbamoyl in 3-position), N,N-dimethyl-carbamoyl, C1-6-alkoxycarbonyl, hydroxy C1-6-alkyl, N-(hydroxy C1-6-alkyl) carbamoyl or carbamoyl C1-6-alkyl and p is 0, 1, 2 or 3. Typical compounds are N-(7-21-thienylacetamido -ceph - 3 - em - 3 - yl methyl) pyridinium-4-carboxylate and N-(7-21-thienylacetamidoceph -3 - em - 3 - yl methyl) - 211 -methylpyridinium-4-carboxylate. The compounds are prepared by reacting a compound of formula <FORM:1030630/C2/2> where R is hydrogen or a thienylacetyl group or a water-soluble salt thereof, in a strongly polar medium with a nucleophile of formula <FORM:1030630/C2/3> where Z and p have the meanings defined above, the resulting compound where R is hydrogen being thienylacetylated. It is preferred to react the above nucleophile with a compound of formula <FORM:1030630/C2/4> Compounds (III) are prepared by reacting 7-aminocephalosporanic acid with a thienylacetylating agent, e.g. thienylacetyl halides or mixed anhydrides, preferably in the presence of an acid-binding agent, e.g. NaHCO3, at pH 5 to 7 in an aqueous medium. Alternatively, cephalosporin C may be reacted with nucleophilic compound (IV) to form a compound of formula <FORM:1030630/C2/5> which is converted to compounds of formula <FORM:1030630/C2/6> by methods known for the conversion of cephalosporin C to 7-ACA. Compound V may be thienylacetylated to compounds (II). Preferably excess compound (IV) is reacted with compound (III) in water, unreacted components are removed by (a) solvent extraction and (b) percolation through ion-exchange resin, and the residual solution is concentrated and freezedried. The compounds are broad spectrum antibiotics effective against penicillin-resisting strains of micro-organisms and possessing low toxicity and high water-solubility (see Division A5).ALSO:A pharmaceutical formulation for human or veterinary use comprises a 7-aminocephalosporanic acid derivative of general formula <FORM:1030630/A5-A6/1> where z is a lower alkyl, carbamoyl (excepting a single carbomoyl group in the 4- position), N-monoalkylcarbamoyl (excepting a single methylcarbamoyl in the 3-position), N,N-diloweralkylcarbamoyl, lower alkoxycarbonyl, hydroxy lower alkyl, N-(hydroxy lower alkyl) carbamoyl or carbomoyl lower alkyl group; p is 0, 1, 2 or 3 and lower alkyl or alkoxy means 1-6 and preferably 1-2 carbon atoms. Typical compounds are (a)N-(7-21-thienylacetamido-ceph-3-em-3 ylmethyl pyridinium-4-carboxylate (b) N-7-21-thienylacetamido-3-em-3 yl methyl 211-methylpyridinium-4-carboxylate and 10) N-(7-21-thienylacetamidoceph-3-em-3-yl methyl)-311-carbamoyl pyridinum-4-carboxylate. The formulations may be for oral, parenteral or topical administration e.g. tablets, capsules, solutions or suspensions for oral or parenteral use, lotions, ointments and creams. A veterinary formulation may be in the form of a veterinary cerate. Optional ingredients are other antibacterial antibiotics such as penicillins and/or tetracyclines. The compounds are broad spectrum antibiotics, effective against penicillin-resistent micro-organisms and having low toxicity and high solubility in water.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5512065A GB1030630A (en) | 1962-12-14 | 1962-12-14 | Antibacterial derivatives of 7-aminocephalosporanic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5512065A GB1030630A (en) | 1962-12-14 | 1962-12-14 | Antibacterial derivatives of 7-aminocephalosporanic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1030630A true GB1030630A (en) | 1966-05-25 |
Family
ID=10473019
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5512065A Expired GB1030630A (en) | 1962-12-14 | 1962-12-14 | Antibacterial derivatives of 7-aminocephalosporanic acid |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1030630A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3624225A (en) * | 1966-06-24 | 1971-11-30 | Glaxo Lab Ltd | Cephalosporin compositions |
-
1962
- 1962-12-14 GB GB5512065A patent/GB1030630A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3624225A (en) * | 1966-06-24 | 1971-11-30 | Glaxo Lab Ltd | Cephalosporin compositions |
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