http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-322386-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_6b6fc801b5bfe5304ffa40d938db6e09 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D499-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D499-76 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D499-00 |
| filingDate | 1966-01-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1966-09-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | ES-322386-A1 |
| titleOfInvention | PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF 6-AMINO-PENICILANICO ACID |
| abstract | The invention relates to 2-pyridyl penicillins, of the formula wherein X is oxygen or sulphur and R is a straight-chain C 1 to C 4 alkyl or alkenyl radical and to the non-toxic salts thereof with organic or inorganic bases. These penicillins are prepared by reacting 6-amino-penicillanic acid or a salt thereof with a compound introducing the acyl radical of an acid of formula wherein X and R are as before, and optionally converting the product into a salt suitable such compounds being: (1) the free acid, in the presence of a water binding agent (e.g. dicyclohexyl carbodiimide) (2) a halide, anhydride, or mixed anhydride of the acid, in the presence of an acid binding agent (e.g. sodium or potassium bicarbonate, carbonate, or hydroxide or a tertiary organic base) or (3) an azide or activated ester of the acid, such as the p-nitrophenyl ester. The reaction using (2) above is performed in organic solvent when the acid binding agent is an organic base, and in aqueous-organic medium when this agent is an alkali metal compound. Examples are given for the preparation of the following penicillins: methoxy- ethoxy- n-propoxy- n-butoxy- allyloxy- methylthio- ethylthio- n-propylthio- and allylthio-2-pyridyl penicillin. Examples are also given for preparing starting materials, as follows: (1) 3-n-butoxy-picolinyl chloride is prepared by refluxing the corresponding acid with thionyl chloride in benzene, in the presence of dimethyl-formamide (2) 3- n-butoxypicolinic acid is prepared by hydrolysis with HCl at elevated temperature, of the corresponding acid amide (3) 3-n-butoxy picoline amide is prepared by reacting 3-hydroxy picoline amide with n-butyl bromide in dimethyl formamide, in the presence of K 2 CO 3 (4) the corresponding 3-methoxy and 3-n-propoxy picoline amides, chlorides and acids are analogously prepared (5) 3-ethylthiopicolinic acid is prepared by reducing dithio-3,31-dipyridyl-2,21- dicarbonic acid to 3-mercapto-picolinic acid, and reacting the latter with ethyl iodide. Pharmaceutical compositions comprise the inventive penicillins or their non-toxic salts and an inert carrier, in conventional forms for oral, rectal, local, or parenteral administration. Salts may be those of Na, K, NH 4 , Mg, Ca, or alkyl- and alkanolamines, heterocyclic bases, and procaine, benzylamine, dibenzylamine, or 1- phenyl-2-propylamine. Oral dosage units may take the form of tablets or dragee cores, with conventional excipients, and dragee coatings. Rectal forms comprise suppositories with a fusible fatty carrier or rectal gelatine capsules containing the active agent in a suitable polyethylene glycol carrier. Dry ampoules for preparing aqueous parenterally administrable solutions contain a sterile water-soluble salt of the penicillin, optionally with solid soluble stabilizers and buffers. Locally applicable compositions may be ointments or powders of the penicillins or their salts, with conventional excipients. |
| priorityDate | 1965-01-29-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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