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Title: Novel, transient pro-drug forms of L-DOPA
Claims: What we claim is: 1. A pro-drug compound of the formula: ##STR19## wherein R represents a hydrogen atom, an acyl group and a -CO-R.sub.3 group, wherein R.sub.3 represents the residue of any N,N-C.sub.1 -C.sub.2 dialkylamino acid or a C.sub.4 -C.sub.6 cycloalkylamino acid; wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group and a -OM group, wherein M is a member selected from the group consisting of an alkali metal and an ammonium ion; and wherein R.sub.2 represents a -CO-R.sub.3 group, wherein R.sub.3 represents the residue of any N,N-(C.sub.1 -C.sub.2)-dialkylamino acid or a C.sub.4 -C.sub.6 -cycloalkylamino acid; ##STR20## wherein R represents an acyl group; wherein R.sub.2 represents a hydrogen atom; and wherein R.sub.1 represents a -NHCH(R.sub.4)COOR.sub.5 group, wherein R.sub.4 represents the residue of any naturally occurring protein amino acid, and wherein R.sub.5 represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group, and a C.sub.1 -C.sub.5 alkylaryl group, and the HX salts thereof, wherein X is a conventional pharmaceutically acceptable acid addition salt anion; ##STR21## wherein R represents an acyl group; wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group, a -OCH.sub.3 group, a -OC.sub.2 H.sub.5 group, a -OC.sub.3 H.sub.7 group, a -OC.sub.4 H.sub.9 group, and a -OCH.sub.2 C.sub.6 H.sub.5 group; and wherein R.sub.2 represents an NH.sub.2 CH(R.sub.6)CO- group, wherein R.sub.6 represents the residue of any naturally occurring protein amino acid, and the HX salts thereof, wherein X is defined as above; ##STR22## wherein R represents an acyl group; wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group, a -OCH.sub.3 group, a -OC.sub.2 H.sub.5 group, a -OC.sub.3 H.sub.7 group, a -OC.sub.4 H.sub.9 group, and a -OCH.sub.2 -C.sub.6 H.sub.5 group; and wherein R.sub.2 represents an NH.sub.2 -CH(R.sub.7)-CO- group, wherein R.sub.7 represents the residue of a 3,4-diacylphenylalanine group having the formula: ##STR23## wherein R is defined as above, and the HX salts thereof, wherein X is as defined above; and ##STR24## wherein n represents an integer of from 2 to 50 with respect to formula (V-A), and wherein n represents an integer of from 1 to 50 with respect to formula (V-B). 2. The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 3. The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 4. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 5. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 6. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 7. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 8. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 9. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-leucine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 10. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-leucine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 11. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-leucine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 12. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-leucine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 13. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 14. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 15. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 16. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 17. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine and its HX salt, wherein X represents pharmaceutically acceptable anion. 18. The compound of the claim 1: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 19. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 20. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 21. The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 22. The compound of claim 1: Glycyl-3,4-dipivalyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 23. The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 24. The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 25. The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 26. The compound of claim 1: L-leucyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 27. The compound of claim 1: L-leucyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 28. The compound of claim 1: L-leucty-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 29. The compound of claim 1: L-leucyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a phramaceutically acceptable anion. 30. The compound of claim 1: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 31. The compound of claim 1: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 32. The compound of claim 1: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 33. The compound of claim 1: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 34. The compound of claim 1: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 35. The compound of claim 1: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 36. The compound of claim 1: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 37. The compound of claim 1: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 38. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L- phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion. 39. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 40. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 41. The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 42. The compound of claim 1: ##STR25## wherein n represents an integer of 7- 20. 43. The compound of claim 1: Poly-3,4-diacetoxy-L-phenylalanine: ##STR26## wherein n represents an integer of 7 - 20. 44. The compound of claim 1: N-[n,n-dimethylamino]-glycyl-3,4-dihydroxyl-L-phenylalanine and its M salt, wherein M represents an alkali metal. 45. The compound of claim 1: N-[n,n-dimethylamino]-glycyl-3,4diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal. 46. The compound of claim 1: 3,4-N,N-dimethylaminoglycyl-L-phenylalanine methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion. 47. The compound of claim 1: N-[n,n-dimethylamino]glycyl-3,4-[N,N-dimethylaminoglycyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal. 48. The compound of claim 1: N-[n,n-diethylaminoglycyl]-3,4-diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal. 49. The compound of claim 1, wherein in formula (II), said C.sub.1 -C.sub.5 alkylaryl group is a member selected from the group consisting of a -CH.sub.2 -C.sub.6 H.sub.5 group, and a -CH.sub.2 -CH.sub.2 -C.sub.6 H.sub.5 group. Other info: Inventors: Bodor, Nicolae S. (Lawrence, KS, US) Sloan, Kenneth B. (Lawrence, KS, US) Hussain, Anwar A. (Lexington, KY, US) Application Number: 569009 Filing Date: 1975-04-17 Publication_date: 1976-12-21 Assignee: Interx Research Corporation (Lawrence, KS) Primary Class(es): 560/251 530/324, 530/325, 530/326, 530/327, 530/328, 530/329, 530/330, 530/331, 560/40, 562/446, 930/290 Other Classes: US Patent Ref:
Other Refs: Primary Examiner: Gotts, Lewis Assistant Examiner: Suyat, Reginald J. Attorney: Blitzer; Charles N. |
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