Patent US3998799A successfully refreshed from Google Patents.
US3998799A
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US
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Novel, transient pro-drug forms of l-dopa
Assignee: Interx Research Corp
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Filing: 1975-04-17
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Granted: 1976-12-21
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Expires: 1995-04-17
Abstract
Abstract There is provided, novel, transient pro-drug forms of L-DOPA (3,4-dihydroxy-L-phenylalanine), having the formula: ##STR1## 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); R represents a hydrogen atom, an acyl group, ##STR2## --CO-pyridyl, or --CO--R 3 , wherein R 3 is the residue of any N,N-C 1 -C 2 dialkylamino acid or a C 4 -C 6 cycloalkylamino acid; R 1 represents --OH, --O-lower alkyl, --O-benzyl, or a naturally occurring protein amino acid; and R 2 represents ##STR3## --CO-pyridyl, a naturally occurring protein amino acid, 3',4'-L-diacyloxy phenylalanine, or --CO-R 3 . These compounds are all 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
2026-11-09 14:17
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/54; C07D213/56; A; A61; A61K; A61K31/00; A61K31/185; A61K31/19; A61K31/195; C07D213/55; C07K; C07K5/00; C07K5/04; C07K5/06; A61K38/00; Y; Y10; Y10S; Y10S930/00; Y10S930/01; Y10S930/29
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
414 words
A pro-drug compound of the formula: ##STR19## wherein R represents a hydrogen atom, an acyl group and a -CO-R 3 group, wherein R 3 represents the residue of any N,N-C 1 -C 2 dialkylamino acid or a C 4 -C 6 cycloalkylamino acid; wherein R 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 2 represents a -CO-R 3 group, wherein R 3 represents the residue of any N,N-(C 1 -C 2 )-dialkylamino acid or a C 4 -C 6 -cycloalkylamino acid; ##STR20## wherein R represents an acyl group; wherein R 2 represents a hydrogen atom; and wherein R 1 represents a -NHCH(R 4 )COOR 5 group, wherein R 4 represents the residue of any naturally occurring protein amino acid, and wherein R 5 represents a member selected from the group consisting of a hydrogen atom, a C 1 -C 5 alkyl group, and a C 1 -C 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 1 represents a member selected from the group consisting of a hydroxyl group, a -OCH 3 group, a -OC 2 H 5 group, a -OC 3 H 7 group, a -OC 4 H 9 group, and a -OCH 2 C 6 H 5 group; and wherein R 2 represents an NH 2 CH(R 6 )CO- group, wherein R 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 1 represents a member selected from the group consisting of a hydroxyl group, a -OCH 3 group, a -OC 2 H 5 group, a -OC 3 H 7 group, a -OC 4 H 9 group, and a -OCH 2 -C 6 H 5 group; and wherein R 2 represents an NH 2 -CH(R 7 )-CO- group, wherein R 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).
Claim 2
Dependent Claim
414 words
A pro-drug compound of the formula: ##STR19## wherein R represents a hydrogen atom, an acyl group and a -CO-R 3 group, wherein R 3 represents the residue of any N,N-C 1 -C 2 dialkylamino acid or a C 4 -C 6 cycloalkylamino acid; wherein R 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 2 represents a -CO-R 3 group, wherein R 3 represents the residue of any N,N-(C 1 -C 2 )-dialkylamino acid or a C 4 -C 6 -cycloalkylamino acid; ##STR20## wherein R represents an acyl group; wherein R 2 represents a hydrogen atom; and wherein R 1 represents a -NHCH(R 4 )COOR 5 group, wherein R 4 represents the residue of any naturally occurring protein amino acid, and wherein R 5 represents a member selected from the group consisting of a hydrogen atom, a C 1 -C 5 alkyl group, and a C 1 -C 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 1 represents a member selected from the group consisting of a hydroxyl group, a -OCH 3 group, a -OC 2 H 5 group, a -OC 3 H 7 group, a -OC 4 H 9 group, and a -OCH 2 C 6 H 5 group; and wherein R 2 represents an NH 2 CH(R 6 )CO- group, wherein R 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 1 represents a member selected from the group consisting of a hydroxyl group, a -OCH 3 group, a -OC 2 H 5 group, a -OC 3 H 7 group, a -OC 4 H 9 group, and a -OCH 2 -C 6 H 5 group; and wherein R 2 represents an NH 2 -CH(R 7 )-CO- group, wherein R 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).
Claim 3
Dependent Claim
17 words
The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 4
Dependent Claim
18 words
The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 5
Dependent Claim
17 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 6
Dependent Claim
17 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 7
Dependent Claim
18 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 8
Dependent Claim
18 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 9
Dependent Claim
18 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-glycine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 10
Dependent Claim
17 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-leucine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 11
Dependent Claim
18 words
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.
Claim 12
Dependent Claim
18 words
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.
Claim 13
Dependent Claim
18 words
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.
Claim 14
Dependent Claim
17 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 15
Dependent Claim
18 words
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.
Claim 16
Dependent Claim
18 words
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.
Claim 17
Dependent Claim
18 words
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.
Claim 18
Dependent Claim
16 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine and its HX salt, wherein X represents pharmaceutically acceptable anion.
Claim 19
Dependent Claim
19 words
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.
Claim 20
Dependent Claim
18 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 21
Dependent Claim
18 words
The compound of claim 1: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 22
Dependent Claim
17 words
The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 23
Dependent Claim
17 words
The compound of claim 1: Glycyl-3,4-dipivalyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 24
Dependent Claim
18 words
The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 25
Dependent Claim
18 words
The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 26
Dependent Claim
18 words
The compound of claim 1: Glycyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 27
Dependent Claim
17 words
The compound of claim 1: L-leucyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 28
Dependent Claim
18 words
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.
Claim 29
Dependent Claim
18 words
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.
Claim 30
Dependent Claim
18 words
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.
Claim 31
Dependent Claim
17 words
The compound of claim 1: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 32
Dependent Claim
18 words
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.
Claim 33
Dependent Claim
18 words
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.
Claim 34
Dependent Claim
18 words
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.
Claim 35
Dependent Claim
17 words
The compound of claim 1: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 36
Dependent Claim
18 words
The compound of claim 1: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 37
Dependent Claim
18 words
The compound of claim 1: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 38
Dependent Claim
18 words
The compound of claim 1: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 39
Dependent Claim
18 words
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.
Claim 40
Dependent Claim
18 words
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.
Claim 41
Dependent Claim
18 words
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.
Claim 42
Dependent Claim
18 words
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.
Claim 43
Dependent Claim
14 words
The compound of claim 1: ##STR25## wherein n represents an integer of 7- 20.
Claim 44
Dependent Claim
16 words
The compound of claim 1: Poly-3,4-diacetoxy-L-phenylalanine: ##STR26## wherein n represents an integer of 7 - 20.
Claim 45
Dependent Claim
16 words
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.
Claim 46
Dependent Claim
16 words
The compound of claim 1: N-[n,n-dimethylamino]-glycyl-3,4diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 47
Dependent Claim
19 words
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.
Claim 48
Dependent Claim
16 words
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.
Claim 49
Dependent Claim
16 words
The compound of claim 1: N-[n,n-diethylaminoglycyl]-3,4-diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 50
Dependent Claim
44 words
The compound of claim 1, wherein in formula (II), said C 1 -C 5 alkylaryl group is a member selected from the group consisting of a -CH 2 -C 6 H 5 group, and a -CH 2 -CH 2 -C 6 H 5 group.
References Cited (Backward Citations)
US3803120A
Cited
US3891696A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-12-21 | 1980-06-21 | 1980-12-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-21 | 1984-06-21 | 1984-12-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-21 | 1988-06-21 | 1988-12-21 | $7700.00 | Window Closed / Lapsed |