Anesthetic polyorganophosphazenes

• US 4,495,174 A
• Filed: 06/21/1982
• Issued: 01/22/1985
• Est. Priority Date: 06/21/1982
• Status: Expired due to Fees

• Current Assignee: Research Corporation
• Original Assignee: Research Corporation
• Inventors: Allcock, Harry R., Neenan, Thomas X., Austin, Paul E.
• Primary Examiner(s): Rotman, Alan L.
• Application Number:
  US06/390,345
• Time in Patent Office: 946 Days
• Field of Search: 560/48, 560/64, 564/12, 564/13, 424/78
• US Class Current: 424/78.37
• CPC Class Codes: A61K 31/80 Polymers containing hetero atoms not provided for in groups A61K31/755 - A61K31/795
• CPC Class Codes: A61K 47/605 the macromolecule containing phosphorus in the main chain, e.g. poly-phosphazene
• CPC Class Codes: C08G 79/025 Polyphosphazenes

Abstract

A long-acting, local anesthetic, comprising a polymeric phosphazene backbone, and 2-amino-4-picoline radical having local anesthetic activity and an amino functional group on the ring of said radical through which said radical is covalently attached to the phosphazene backbone by a phosphorous-nitrogen single bond is disclosed along with medicaments containing such anesthetics.

Claims

1. A long-acting, local anesthetic, comprising:

a polymeric phosphazene backbone, and

an organic radical having local anesthetic activity and an amino functional group on a phenyl ring through which said radical is covalently attached to said phosphazene backbone by a phosphorous-nitrogen single bond, and said organic radical being selected from the group consisting of radicals of benzocaine, butethamine, butyl ester of p-aminobenzoic acid, m-butethamine, procaine, chloroprocaine proparacaine, propoxycaine and tetracaine.

2. The local anesthetic of claim 1, wherein said organic radical is a radical of benzocaine.

3. The local anesthetic of claim 1, wherein said organic radical is a radical of butethamine.

4. The local anesthetic of claim 1, wherein said organic radical is a radical butyl 4-aminobenzoate.

5. The local anesthetic of claim 1, wherein said organic radical is a radical of procaine.

6. The local anesthetic of claim 1, wherein said organic radical is a radical of tetracaine.

7. The local anesthetic of claim 1, wherein said organic radical is a radical of propoxycaine.

8. The local anesthetic of claim 1, wherein said organic radical is a radical of proparacaine.

9. The local anesthetic of claim 1, wherein said organic radical is a radical of chloroprocaine.

10. The local anesthetic of claim 1, wherein said polymeric phosphazene backbone is a cyclic trimer.

11. The local anesthetic of claim 1, wherein said polymeric phosphazene backbone is a linear chain containing from 3 to 30,000 ##STR16## repeating units.

12. The local anesthetic of claim 11, wherein said backbone contains from 100 to 20,000 repeating units.

13. The local anesthetic of claim 11, wherein said backbone contains about 15,000 repeating units.

18. The local anesthetic of claim 1, wherein said backbone contains about 15,000 repeating units.

19. A long-acting local anesthetic medicament, comprising a local anesthetic effective amount of a compound of claim 1 in admixture with a pharmaceutically acceptable carrier.

20. A long-acting local anesthetic medicament, comprising a compound of claim 1 in admixture with a pharmaceutically acceptable carrier.

14. A long-acting, local anesthetic, comprising:

a polymeric phosphazene backbone, and an organic radical having local anesthetic activity which is an ester of p-aminobenzoic acid and an amino functional group on a phenyl ring through which said radical is covalently attached to said phosphazene backbone by a phosphorous-nitrogen single bond.

15. The local anesthetic of claim 14, wherein a position on a phenyl ring ortho to said amino functional group is unsubstituted.

16. The local anesthetic of claim 15, wherein said polymeric phosphazene backbone is a cyclic trimer.

17. The local anesthetic of claim 15, wherein said polymeric phosphazene backbone is a linear chain containing from 100 to 20,000 repeating units.