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US3939253A Expired / Lapsed US ⏱️ 0.0 years remaining

Novel, transient pro-drug forms of l-dopa useful in the treatment of parkinson's disease

Assignee: Interx Research Corp
•
Filing: 1975-04-10
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Granted: 1976-02-17
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Expires: 1995-04-10
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Abstract

Abstract There is provided, novel, transient pro-drug forms of L-DOPA (3,4-dihydroxy-L-phenylalanine), having the formula: ##SPC1## Wherein R represents a member selected from the group consisting of a hydrogen atom, a --COCH 3 group, a --COC 2 H 5 group, a --COOC 2 H 5 group, and a --CO--C(CH 3 ) 3 group; wherein R 1 represents a member selected from the group consisting of a hydroxyl group, a --OM group (wherein M represents an alkali metal or an ammonium ion), a --OCH 2 --C 6 H 5 group, a --OCH 3 group, a --OC 2 H 5 group, and --NH--CH(R 3 )COOH group, wherein R 3 represents the residue of any naturally occurring amino acid; and wherein R 2 represents a member selected from the group consisting of a hydrogen atom, a formyl group, a --CO--C 6 H 5 group, a --CO--pyridyl group, a --CO(R 5 )--CH=CH(R 4 ) group, and a NH 2 --CH(R 6 )--CO-- group, wherein R 4 represents a methyl group and wherein R 5 represents a member selected from the group consisting of a methyl group, a --OC 2 H 5 group, and a C 6 H 5 -- group, and wherein R 6 represents the residue of any naturally occurring amino acid, With the proviso that simultaneously, R cannot represent a hydrogen atom when R 1 represents a --OCH 3 group or a --OH group and when R 2 represents a hydrogen atom respectively; R cannot represent a hydrogen atom when R 1 represents either a hydroxyl group or a --OCH 3 group and R 2 represents a --COCH 3 group, respectively; R cannot represent a hydrogen atom when R 1 represents a hydroxyl group and R 2 represents a formyl group respectively, R cannot represent a hydrogen atom when R 1 represents a hydroxyl group and R 2 represents a benzoyl group, respectively; and, R cannot represent a hydrogen atom when R 1 represents a hydroxyl group and R 6 represents the residue of L-leucine, respectively. These compounds are useful in the treatment of Parkinson's Disease.

Inventors

  • 👤 Nicolae S. Bodor
  • 👤 Kenneth B. Sloan
  • 👤 Anwar A. Hussain

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 08:18
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06017; C07K5/06026; C07K5/06078; A; A61; A61K; A61K38/00

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 130 words
A method for treating Parkinson's Disease in warmblooded animals which comprises administering thereto, an antiParkinsonism effective amount of a compound having the formula: ##SPC9## wherein R represents a member selected from the group consisting of hydrogen, --COCH 3 , --COC 2 H 5 , --COOC 2 H 5 , and --CO--C(CH 3 ) 3 ; wherein R 1 represents a member selected from the group consisting of hydroxyl and --OM, wherein M represents a member selected from the group consisting of an alkali metal and an ammonium ion; and wherein R 2 represents --(R 5 )CO--CH=C(R 4 )--, wherein R 4 represents methyl or ethoxy, and wherein R 5 represents a member selected from the group consisting of methyl, --C 6 H 5 , and --OC 2 H 5 .
Claim 2
Independent Claim 130 words
A method for treating Parkinson's Disease in warmblooded animals which comprises administering thereto, an antiParkinsonism effective amount of a compound having the formula: ##SPC9## wherein R represents a member selected from the group consisting of hydrogen, --COCH 3 , --COC 2 H 5 , --COOC 2 H 5 , and --CO--C(CH 3 ) 3 ; wherein R 1 represents a member selected from the group consisting of hydroxyl and --OM, wherein M represents a member selected from the group consisting of an alkali metal and an ammonium ion; and wherein R 2 represents --(R 5 )CO--CH=C(R 4 )--, wherein R 4 represents methyl or ethoxy, and wherein R 5 represents a member selected from the group consisting of methyl, --C 6 H 5 , and --OC 2 H 5 .
Claim 3
Dependent Claim 19 words
The method of claim 1, wherein said compound is administered in combination with a pharmaceutically acceptable inert carrier material.
Claim 4
Dependent Claim 15 words
The method of claim 1, wherein said compound is 3,4-diacetyloxy-N[1-methyl-2-acetylvinyl]-L-phenylalanine and its alkali metal salt.
Claim 5
Dependent Claim 20 words
The method of claim 1, wherein said compound is 3,4-dihydroxy-N[1-methyl-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 6
Dependent Claim 20 words
The method of claim 1, wherein said compound is 3,4-dipivalyloxy-N[1-methyl-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 7
Dependent Claim 20 words
The method of claim 1, wherein said compound is 3,4-dihydroxy-N[1-ethoxy-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 8
Dependent Claim 20 words
The method of claim 1, wherein said compound is 3,4-diacetyloxy-N[1-ethoxy-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 9
Dependent Claim 20 words
The method of claim 1, wherein said compound is 3,4-dipivalyloxy-N[1-ethoxy-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 10
Dependent Claim 139 words
A pharmaceutical composition for use in the treatment of Parkinson's Disease, comprising a pharmaceutically acceptable inert carrier material in combination with an anti-Parkinsonism effective amount of a compound having the formula: ##SPC10## wherein R represents a member selected from the group consisting of hydrogen, --COCH 3 , --COC 2 H 5 , --COOC 2 H 5 , and --CO--C(CH 3 ) 3 ; wherein R 1 represents a member selected from the group consisting of hydroxyl and --OM, wherein M represents a member selected from the group consisting of an alkali metal and an ammonium ion; and wherein R 2 represents -- (R 5 )CO--CH=C(R 4 )--, wherein R 4 represents methyl or ethoxy, and wherein R 5 represents a member selected from the group consisting of methyl, --C 6 H 5 , and --OC 2 H 5 .
Claim 11
Dependent Claim 139 words
A pharmaceutical composition for use in the treatment of Parkinson's Disease, comprising a pharmaceutically acceptable inert carrier material in combination with an anti-Parkinsonism effective amount of a compound having the formula: ##SPC10## wherein R represents a member selected from the group consisting of hydrogen, --COCH 3 , --COC 2 H 5 , --COOC 2 H 5 , and --CO--C(CH 3 ) 3 ; wherein R 1 represents a member selected from the group consisting of hydroxyl and --OM, wherein M represents a member selected from the group consisting of an alkali metal and an ammonium ion; and wherein R 2 represents -- (R 5 )CO--CH=C(R 4 )--, wherein R 4 represents methyl or ethoxy, and wherein R 5 represents a member selected from the group consisting of methyl, --C 6 H 5 , and --OC 2 H 5 .
Claim 12
Dependent Claim 15 words
The composition of claim 9, wherein said compound is 3,4-diacetyloxy-N[1-methyl-2-acetylvinyl]-L-phenylalanine and its alkali metal salt.
Claim 13
Dependent Claim 20 words
The composition of claim 9, wherein said compound is 3,4-dihydroxy-N[1-methyl-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 14
Dependent Claim 20 words
The composition of claim 9, wherein said compound is 3,4-dipivalyloxy-N[1-methyl-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 15
Dependent Claim 20 words
The composition of claim 9, wherein said compound is 3,4-dihydroxy-N[1-ethoxy-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 16
Dependent Claim 20 words
The composition of claim 9, wherein said compound is 3,4-diacetyloxy-N[1-ethoxy-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 17
Dependent Claim 20 words
The composition of claim 9, wherein said compound is 3,4-dipivalyloxy-N[1-ethoxy-2-acetylvinyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.

References Cited (Backward Citations)

No citation records indexed.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-02-16 1979-08-18 1980-02-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-02-16 1983-08-18 1984-02-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-02-16 1987-08-18 1988-02-17 $7700.00 Window Closed / Lapsed

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