IE44395B1 - 7-aminocephalosporin intermediates - Google Patents
7-aminocephalosporin intermediatesInfo
- Publication number
- IE44395B1 IE44395B1 IE1645/80A IE164580A IE44395B1 IE 44395 B1 IE44395 B1 IE 44395B1 IE 1645/80 A IE1645/80 A IE 1645/80A IE 164580 A IE164580 A IE 164580A IE 44395 B1 IE44395 B1 IE 44395B1
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- compound according
- compound
- formula
- salt
- Prior art date
Links
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Description
This invention relates to cephalosporin compounds which are useful as intermediates™ preparing other cephalosporin compounds which have antibacterial activity and are described and claimed in Patent Specification No. 44393.
According to the present invention there are provided compounds of the formula
where £ is an integer from two to five; and R is hydrogen or a protective ester-forming group.
Examples of suitable ester-forming groups R are t-butyl, benzhydryl, trichloroethyl, benzyl, benzyloxymethyl, p--ni tropheny 1, p-methoxyphenyl, p-methoxybenzyl and p-nitrobenzyl groups. The ester-forming groups R can be introduced and removed by known methods.
3 9 9
The 7-amino-3-sulfaminalkyltetrazolylthiomethyl cephalosporin compounds of formula I can be prepared by reacting
7-formamidocephalosporanic acid, prepared by reaction of
7-amino-cephalosporanic acid with formic acid and acetic anhydride, and a tetrazole-thiol of formula
/)-N
N-N (CH2)n-NHS03H (where n is as defined above) or a salt thereof, followed by treatment with an acid, such as hydrochloric acid, to remove the formyl group from the product.
The tetrazole-thiols of formula II are described and claimed in
Patent Specification No. 44394.
The invention also includes salts of the compounds of formula I, for example with alkali metals such as sodium or potassium, alkaline earth metals, such as calcium, or the ammonium cation.
The following Example illustrates the invention but is not to be construed as limiting the scope thereof. The temperatures are in degrees Centigrade °C.
• LWI-L
7-Amino-3-[l-(2-sulfanrinoethyl)tetrazole-5-ylthiomethylJ -3cepheffi-4-carboxylic acid
To a mixture of 97 g (200 ml, 2.1 mol) of formic acid, distilled from anhydrous copper sulfate, and 37.5 ml (0.4 mol) of acetic acid anhydride were added 25.0 g (0.1 mol) of 7-aminocephalosporanic acid. The mixture was stirred at ambient temperature for 0.5 hour, then evaporated to dryness. The residue was dissolved in ethyl acetate, and the ethyl acetate solution was filtered and evaporated to dryness to give a residue which was recrystallized from ether10 petroleum ether to give /-formamidocephalosporanic acid.
A mixture of 1.0 g (3.3 mol) o-f 7-formaniTdocephalosporanic acid and 0.7 g (2.6 mol) of l-(2-sulfaminoethyl)tetrazo1e-5-thiol disodium salt in 15 ml of water is stirred at 65-70° for 3 hours while maintaining the pH at 7.0. The mixture is cooled, acidified to pH 1.0 with hydrochloric acid and extracted with ethyl acetate.
The extract is filtered, and the filtrate is evaporated to dryness to give a residue which is dissolved in methanol. The methanol solution is filtered and ether is added to precipitate the title compound which is collected by filtration.
Claims (9)
1. A compound of the formula: (CH 2 ) n -NHS0 3 H where n is an integer from two to five; and R is hydrogen or a protective ester-forming group. 5
2. A compound according to claim 1, where R is benzylhydryl, t-butyl, trichloroethyl, benzyl, benzyloxymethyl, p-nitrophenyl, p-methoxyphenyl, p-methoxybenzyl or p-nitrobenzyl.
3. A compound according to claim 2, where n is two.
4. 7-Amino-3- [l-(2-sulfaminoethyl)tetrazol-5-ylthiomethylJ] 10 3-cephem-4-carboxylic acid.
5. A compound according to any of the preceding claims in the form of a salt thereof.
6. A compound as claimed in claim 1, as herein specifically described in the Example.
7. A process for preparing a compound according to Claim 1 which comprises reacting 7- aminocephalosporanic acid with formic and aceticanhydride to produce 7-formamidocephalosporanic acid and reacting the 7-formamidocephalosporanic acid with a tetrazole5 thiol of formula Pi - N (CH 2 ) n -NHS0 3 H (where n is as defined in claim 1) or a salt thereof, followed by treatment with an acid to remove the formyl group from the product.
8. A process for preparing a compound of claim 1, substantially as 10 described in the Example.
9. A compound according to claim 1, whenever prepared by a process according to any of claims 7 and 8.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62716475A | 1975-10-30 | 1975-10-30 | |
| US66583776A | 1976-03-11 | 1976-03-11 | |
| US05/704,142 US4118491A (en) | 1976-03-11 | 1976-07-12 | 7-Acyl-3-(sulfaminoalkyl substituted tetrazolylthiomethyl)cephalosporins, antibacterial compositions containing them and methods of treating bacterial infections with them |
| IE2377/76A IE44393B1 (en) | 1975-10-30 | 1976-10-27 | New chephalosporins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE44395L IE44395L (en) | 1977-09-11 |
| IE44395B1 true IE44395B1 (en) | 1981-11-18 |
Family
ID=27452058
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1644/80A IE44394B1 (en) | 1975-10-30 | 1976-10-27 | Substituted tetrazole 5-thiols |
| IE1645/80A IE44395B1 (en) | 1975-10-30 | 1976-10-27 | 7-aminocephalosporin intermediates |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1644/80A IE44394B1 (en) | 1975-10-30 | 1976-10-27 | Substituted tetrazole 5-thiols |
Country Status (1)
| Country | Link |
|---|---|
| IE (2) | IE44394B1 (en) |
-
1976
- 1976-10-27 IE IE1644/80A patent/IE44394B1/en unknown
- 1976-10-27 IE IE1645/80A patent/IE44395B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE44394L (en) | 1977-04-30 |
| IE44394B1 (en) | 1981-11-18 |
| IE44395L (en) | 1977-09-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4012382A (en) | α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives | |
| CA1273629A (en) | 7-amino-3-propenylcephalosporanic acid and esters thereof | |
| HU176287B (en) | Process for producing 7-bracket-2-thienylacetamido-bracket closed-3-triasolylthiomethyl-3-cepheme-4-carboxylic acid derivative | |
| US3962272A (en) | 1h-tetrazole-1-acetate esters and acids and process therefor | |
| US4564676A (en) | Process for preparing cephalosporin derivatives | |
| IE44395B1 (en) | 7-aminocephalosporin intermediates | |
| CA1069120A (en) | Process for preparing 7-aminocephalosporanic acid derivatives | |
| EP0023045B1 (en) | Imidazolecarboxylic acid derivatives of penicillins and cephalosporins | |
| GB1580482A (en) | 7-amino-3-(sulphoalkyl-1,3,4-oxadiazol-2-yl)-thiomethyl-3-cephem-4-carboxylic acid derivatives | |
| US4959495A (en) | Process for the preparation of intermediates used to produce aminothiazoloximino cephalosporins | |
| US4327211A (en) | Method for preparation of cephalosporin compounds | |
| US4048155A (en) | Process for preparing 7 α-alkoxycephalosporin derivatives | |
| GB1570095A (en) | 7-aminocephalosporin intermediates | |
| EP0060301B1 (en) | Process for preparing cephalosporin compounds | |
| US4304909A (en) | Process for producing 7-(D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl)acetamido)-3-(5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl)-.DELTA.3 -cephem-4-carboxylic acid and a pharmaceutically acceptable salt thereof | |
| US3843642A (en) | Cephalosporin c derivatives | |
| US3422103A (en) | 7(aminophenylacetamido)cephalosporanic acids | |
| US4665168A (en) | Cephalosporin intermediate | |
| CA1071621A (en) | Process for preparing 7-aminocephalosporanic acid derivatives | |
| US4115646A (en) | Process for preparing 7-aminocephalosporanic acid derivatives | |
| IE45758B1 (en) | 7- -oxyiminoacylaminocephalosporins | |
| GB1604740A (en) | 7-isothiazolylthioacetamido-7-methoxycephalosporanic acid derivatives | |
| KR860001087B1 (en) | Process for preparing cephalosporanic acid derivatives | |
| EP0000100A1 (en) | 7-Acylamino-3-(1-(2-sulfamoylaminoethyl)-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids, a process for their preparation and compositions containing them | |
| US3943126A (en) | Process for acylating a 7-aminocephalosporin |