L-N-n-propylpipecolic acid-2,6-xylidide

Details L-N-n-propylpipecolic acid-2,6-xylidide L-N-n-propylpipecolic acid-2,6-xylidide

1985-10-09

1987-09-22

Milestone, Norma S.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546225, 514817, 514818, C07D21160, A61K 31445

Patent

active

046955763

ABSTRACT:
The local anesthetic, L-N-n-propylpipecolic acid-2,6-xylidide, namely: ##STR1## This compound is prepared by chlorinating L-pipecolic acid to yield the acid chloride, namely L-pipecolic acid chloride. The acid chloride is then reacted with 2,6-xylidine to yield L-pipecolic acid-2,6-xylidide. The L-N-pipecolic acid-2,6-xylidide is then propylated to yield the L-N-n-propylpipecolic acid-2,6-xylidide, which is a potent local anesthetic for humans and is of relatively low toxicity.

REFERENCES:
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patent: 4110331 (1978-08-01), Pettersson
patent: 4302465 (1981-11-01), Ekenstam et al.
Luduena, F. P., Annual Review of Pharmacology, "Duration of Local Anaesthesia", 9, 503-520 (1969).
Tullar, B. F., J. Med. Chem., "Optical Isomers of Mepivacaine and Bupivacaine", 14, 891-892 (1971).
Friberger, P. et al., Acta Pharm. Suecica, "Some Physicochemical Properties of The Racemates and The Optically Active Isomers of Two Local Anaesthetic Compounds", 8, 361-364 (1971).
Aberg, G., Acta Pharmacol et Toxicol, "Toxicological and Local Anaesthetic Effects of Optically Active Isomers of Two Local Anaesthetic Compounds", 31, 273-286 (1972).
Af Ekenstam, B., et al., Acta Chemica Scandinavica, "Local Anaesthetics I. N-Alkyl Pyrrolidine and N-Alkyl Piperidine Carboxylic Acid Amides", 11, 1183-1190 (1957).
Aberg, G., et al., Acta Pharmacol. et Toxicol, "Studies on The Duration of Local Anaesthesia: Structure/Activity Relationships in a Series of Homologous Local Anaesthetics", 41, 432-443 (1977).
Aberg, G., Linkoping University Medical Dissertations, "Studies on Mepivacaine and its Optically Active Isomers with Special Reference to Vasaoactive Properties", No. 5, pp. 1-32 (1972).

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