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

• US 4,695,576 A
• Filed: 10/09/1985
• Issued: 09/22/1987
• Est. Priority Date: 07/09/1984
• Status: Expired due to Term

• Current Assignee: Astra Laekemedel AB
• Original Assignee: Astra Laekemedel AB
• Inventors: af Ekenstam, Bo T., Bovin, Christer
• Primary Examiner(s): Milestone, Norma S.
• Application Number:
  US06/785,819
• Time in Patent Office: 713 Days
• Field of Search: 546/225, 514/330, 514/817, 514/818
• US Class Current: 514/330
• CPC Class Codes: C07D 211/60 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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.

Claims

1. A method for inducing local anesthesia comprising administration to a patient needing local anesthesia an anesthetizing amount of the substantially pure L-isomer of N-n-propylpipecolic acid-2,6-xylidide or its water soluble salts substantially devoid of the racemic and the D-isomer of N-n-propylpipecolic acid-2,6-xylidide.

2. A method according to claim 1 wherein the pure L-isomer of N-n-propylpipecolic acid-2,6-xylidide or its water soluble salts is contained in an injectable aqueous solution.

3. Substantially pure L-isomer of N-n-propylpipecolic acid-2,6-xylidide, and its water soluble salts, substantially devoid of racemic and D-N-n-propylpipecolic acid-2,6-xylidide.

4. The method of inducing local anesthesia in humans by the application of the compound of claim 3 to the region intended to be anesthetized in a concentration sufficient to effect anesthesia, and below that which would confer an adverse toxic reaction.

5. An injectable local anesthetic composition comprising an aqueous solution containing a sufficient amount of a water soluble salt of the compound of claim 3 to induce local anesthesia in humans, but with the concentration being below that which would confer an adverse toxic reaction.

6. A topical local anesthetic composition comprising a carrier and the compound of claim 3.