1,2,4-Triazines

• US 4,347,359 A
• Filed: 01/15/1981
• Issued: 08/31/1982
• Est. Priority Date: 01/17/1980
• Status: Expired due to Fees

• Current Assignee: Rhone-Poulenc Sante (Sanofi )
• Original Assignee: Rhone-Poulenc Industries
• Inventors: Peyronel, Jean-Francois, Le Roy, Pierre, Moutonnier, Claude, Farge, Daniel
• Primary Examiner(s): Ford, John M.
• Application Number:
  US06/225,446
• Time in Patent Office: 593 Days
• Field of Search: 544/182
• US Class Current: 544/182
• CPC Class Codes: C07D 253/075 Two hetero atoms, in positions 3 and 5
• CPC Class Codes: C07D 257/04 Five-membered rings
• CPC Class Codes: C07D 317/28 Radicals substituted by nitrogen atoms nitro radicals C07D317/16
• CPC Class Codes: C07D 319/06 not condensed with other rings

Abstract

New thiols of the general formula: ##STR1## wherein A represents a 2-hydroxy-1-oxoethan-1-yl-2-ylidene or alkoxycarbonylmethyne radical or a nitrogen atom and R represents various substituted alkyl radicals, and their alkali metal and alkaline earth metal salts are useful as intermediates in the preparation of cephalosporins having anti-bacterial properties.

Claims

1. A triazine of the formula:

##STR57## wherein R represents;

(a) 2,2-dimethyl-dioxolan-4-yl methyl or 2,2-dimethyldioxan-5-yl;

(b) C₂ -C₄ alkyl substituted with a member selected from the group consisting of alkylsulphonylamino, sulphamoylamino, alkoxycarbonylamino, ureido, alkylureido, dialkylureido and substituted acylamino wherein the acyl group is substituted with hydroxy, amino, alkylamino, or dialkylamino;

(c) C₂ -C₅ alkyl substituted with alkoxyimino or hydroxyimino;

(d) a radical of the formula;

##STR58## wherein alk represents C₁ -C₄ alkylene, X.sup.α

and Y.sup.α

are identical and represent oxygen or sulphur atoms and R.sup.α

represents an alkyl radical, or X.sup.α and

Y.sup.α

are identical or different and represent oxygen or sulphur atoms and the radicals R.sup.α

together form an alkylene radical of 2 or 3 carbon atoms, and R.sup.β

represents C₁ -C₃ alkyl;

(e) carbamoyloxyalkyl, alkylsulphinylalkyl, or alkylsulphonylalkyl in which the alkyl moiety bonded to the triazine grouping in formula I has 2 to 4 carbon atoms;

(f) phenylalkyl or alkylthioalkyl;

or

(g) a radical of the formula;

##STR59## wherein alk, X.sup.α

, Y.sup.α

, and R.sup.α

are as defined previously, the alkyl and acyl moieties of radicals mentioned above are linear or branched and, unless otherwise specified, contain 1 to 4 carbon atoms, or

an alkali metal or alkaline earth metal salt thereof.

2. The compound of claim 1 wherein R represents a carbamoyloxyalkyl, alkylsulphinylalkyl or alkylsulphonylalkyl radical in which the alkyl moiety bonded to the triazine grouping in formula I has 2 to 4 carbon atoms;

a phenylalkyl or alkylthioalkyl radical;

or a radical of formula IV wherein alk, X.sup.α

, Y.sup.α

, and R.sup.α

are as defined in claim 1.

3. The compound of claim 1 wherein R is as defined in (a), (b), (c), or (d) in claim 1.

4. The compound of claim 1 wherein R represents 2,2-dimethyldioxolan-4-yl methyl, 2,2-dimethyldioxan-5-yl, an alkyl radical of 2 to 4 carbon atoms, substituted by an alkylsulphonylamino radical, substituted acylamino wherein the acyl moiety is substituted with amino, alkoxycarbonylamino, alkylureido, phenylalkyl, alkylthioalkyl, or a radical of the formula III or IV.

5. The compound of claim 1 wherein R represents 2,2-dimethyldioxolan-4-yl methyl, an alkyl radical of 2 to 4 carbon atoms substituted by an alkoxycarbonylamino radical, phenylalkyl, alkylthioalkyl, or a radical of the formula III or IV.

6. A compound according to claim 1 which is 4-benzyl-5,6-dioxo-3-thioxo-perhydro-1,2,4-triazine or an alkali metal or alkaline earth metal salt thereof.

7. A compound according to claim 1 which is 5,6-dioxo-4-(2-methylthioethyl)-3-thioxo-perhydro-1,2,4-triazine or an alkali metal or alkaline earth metal salt thereof.

8. A compound according to claim 1 which is 4-(2,2-dimethoxyethyl)-5,6-dioxo-3-thioxo-perhydro-1,2,4-triazine or an alkali metal or alkaline earth metal salt thereof.

9. A compound according to claim 1 which is 4-(2,2-diethoxyethyl)-5,6-dioxo-3-thioxo-perhydro-1,2,4-triazine or an alkali metal or alkaline earth metal salt thereof.

10. A compound according to claim 1 which is 4-(2,2-dimethyldioxolan-4-yl-methyl)-5,6-dioxo-3-thioxo-perhydro-1,2,4-triazine or an alkali metal or alkaline earth metal salt thereof.

11. A compound according to claim 1 which is 4-(2-t-butoxycarbonylaminoethyl)-5,6-dioxo-3-thioxoperhydro-1,2,4-triazine or an alkali metal or alkaline earth metal salt thereof.

12. A compound according to claim 1 which is 4-(3,3-diethoxy-2-hydroxypropyl)-5,6-dioxo-3-thioxo-perhydro-1,2,4-triazine or an alkali metal or alkaline earth metal salt thereof.