Patent US3233108A successfully refreshed from Google Patents.
Patent US4035507A successfully refreshed from Google Patents.
US4035507A
Expired / Lapsed
US
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Novel, transient pro-drug forms of L-DOPA to treat Parkinson's disease
Assignee: Interx Research Corp
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Filing: 1976-07-23
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Granted: 1977-07-12
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Expires: 1996-07-23
Abstract
Abstract There is provided, novel, transient pro-drug forms of L-DOPA (3,4-dihydroxy-L-phenylalanine), having the formula: ##STR1## wherein R represents a hydrogen atom, an acyl group, ##STR2## group, a -CO-pyridyl 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 (e.g., ##STR3## wherein R 1 represents a member selected from the group consisting of a hydroxyl group and a --OM group, wherein M is an alkali metal (Na, K, etc.) or an ammonium ion; and wherein R 2 represents a member selected from the group consisting of a ##STR4## group, a -CO-pyridyl 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 (e.g., ##STR5## 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 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 (e.g., methyl, ethyl, propyl, butyl, pentyl), and a C 1 -C 5 alkylaryl group (e.g., --CH 2 -C 6 H 5 , --CH 2 -CH 2 --C 6 H 5 , etc.), and the HX salts thereof, wherein X is a conventional pharmaceutically acceptable acid addition salt anion (e.g., chloride, bromide, perchlorate, methanesulfonate, succinate, etc.); ##STR6## 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 amino acid, and the HX salts thereof, wherein X is defined as above; ##STR7## wherein R represents a member selected from the group consisting of 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-L-diacylphenylalanine group having the formula: ##STR8## wherein R is defined as above, and the HX salts thereof, wherein X is as defined above; and ##STR9## 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). 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
2026-10-26 23:31
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
Claims Analysis
Total Claims: 113
Claim 1
Independent Claim
447 words
A method for treating Parkinson's Disease in warm-blooded animals which comprises orally administering to a warm-blooded animal afflicted with Parkinson's Disease, an anti-Parkinsonism effective amount of a compound having the formula: ##STR24## 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; ##STR25## 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; ##STR26## 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; ##STR27## wherein R represents a member selected from the group consisting of 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-L-diacylphenylalanine group having the formula: ##STR28## wherein R is defined as above, and the HX salts thereof, wherein X is as defined above; and ##STR29## 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
Independent Claim
447 words
A method for treating Parkinson's Disease in warm-blooded animals which comprises orally administering to a warm-blooded animal afflicted with Parkinson's Disease, an anti-Parkinsonism effective amount of a compound having the formula: ##STR24## 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; ##STR25## 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; ##STR26## 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; ##STR27## wherein R represents a member selected from the group consisting of 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-L-diacylphenylalanine group having the formula: ##STR28## wherein R is defined as above, and the HX salts thereof, wherein X is as defined above; and ##STR29## 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
21 words
The method of claim 1, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 4
Dependent Claim
22 words
The method of claim 1, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 5
Dependent Claim
21 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 6
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-nicotinoyl-3,4-dihydroxy-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: N-nicotinoyl-3,4-diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 8
Dependent Claim
21 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 9
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 10
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 11
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 12
Dependent Claim
21 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-leucine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 13
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-leucine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 14
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-leucine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 15
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-leucine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 16
Dependent Claim
21 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 17
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 18
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 19
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 20
Dependent Claim
21 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 21
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 22
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 23
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 24
Dependent Claim
21 words
The method of claim 1, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 25
Dependent Claim
21 words
The method of claim 1, wherein said compound is: Glycyl-3,4-dipivalyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 26
Dependent Claim
21 words
The method of claim 1, wherein said compound: Glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 27
Dependent Claim
22 words
The method of claim 1, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 28
Dependent Claim
22 words
The method of claim 1, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 29
Dependent Claim
21 words
The method of claim 1, wherein said compound is: L-leucyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 30
Dependent Claim
22 words
The method of claim 1, wherein said compound is: L-leucyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 31
Dependent Claim
22 words
The method of claim 1, wherein said compound is: L-leucyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 32
Dependent Claim
22 words
The method of claim 1, wherein said compound is: L-leucyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 33
Dependent Claim
21 words
The method of claim 1, wherein said compound is: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 34
Dependent Claim
22 words
The method of claim 1, wherein said compound is: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 35
Dependent Claim
22 words
The method of claim 1, wherein said compound is: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 36
Dependent Claim
22 words
The method of claim 1, wherein said compound is: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 37
Dependent Claim
21 words
The method of claim 1, wherein said compound is: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 38
Dependent Claim
22 words
The method of claim 1, wherein said compound is: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 39
Dependent Claim
22 words
The method of claim 1, wherein said compound is: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 40
Dependent Claim
22 words
The method of claim 1, wherein said compound is: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 41
Dependent Claim
21 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 42
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 43
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 44
Dependent Claim
22 words
The method of claim 1, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 45
Dependent Claim
20 words
The method of claim 1, wherein said compound is: Poly-3,4-dihydroxy-L-phenylalanine: ##STR30## wherein n represents an integer of 7 - 20.
Claim 46
Dependent Claim
19 words
The method of claim 1, wherein said compound is: Poly-3,4-diacetoxy-L-phenylalanine: ##STR31## wherein n represents an integer of 7- 20.
Claim 47
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-[n,n-dimethylamino]-glycyl-3,4-dihydroxy-L-phenyl-alanine and its M salt, wherein M represents an alkali metal.
Claim 48
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-[n,n-dimethylamino]-glycyl-3,4-diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 49
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-nicotinoyl-3,4-dinicotinoyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 50
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-3-pyridylacetyl-3,4-dihydroxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 51
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-3-pyridylacetyl-3,4-diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 52
Dependent Claim
23 words
The method of claim 1, wherein said compound is: 3,4-N,N-dimethylaminoglycyl-L-phenylalanine methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 53
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-[n,n-dimethylamino]glycyl-3,4-[N,N-dimethylaminoglycyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 54
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-[n,n-dimethylaminoglycyl]-3,4-diacetyloxy-L-phenyl-alanine and its M salt, wherein M represents an alkali metal.
Claim 55
Dependent Claim
20 words
The method of claim 1, wherein said compound is: N-nicotinoyl-3,4-dipivalyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 56
Dependent Claim
43 words
The method 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 5 group.
Claim 57
Dependent Claim
449 words
An orally administered pharmaceutical composition useful in the treatment of Parkinson's Disease which comprises an anti-Parkinsonism effective amount of a compound having the formula: ##STR32## 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 dialkyl-amino 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; ##STR33## 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; ##STR34## 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; ##STR35## wherein R represents a member selected from the group consisting of 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-L-diacylphenylalanine group having the formula: ##STR36## wherein R is defined as above, and the HX salts thereof, wherein X is as defined above; and ##STR37## 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), in combination with an orally acceptable pharmaceutical inert carrier.
Claim 58
Dependent Claim
449 words
An orally administered pharmaceutical composition useful in the treatment of Parkinson's Disease which comprises an anti-Parkinsonism effective amount of a compound having the formula: ##STR32## 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 dialkyl-amino 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; ##STR33## 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; ##STR34## 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; ##STR35## wherein R represents a member selected from the group consisting of 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-L-diacylphenylalanine group having the formula: ##STR36## wherein R is defined as above, and the HX salts thereof, wherein X is as defined above; and ##STR37## 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), in combination with an orally acceptable pharmaceutical inert carrier.
Claim 59
Dependent Claim
21 words
The composition of claim 56 wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 60
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 61
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 62
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-nicotinoyl-3,4-dihydroxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 63
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-nicotinoyl-3,4-diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 64
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine and its HX salt, wherein X represents pharmaceutically acceptable anion.
Claim 65
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 66
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 67
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-glycine-benzyl ester and its HX salt, wherein K represents a pharmaceutically acceptable anion.
Claim 68
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-leucine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 69
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-leucine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 70
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-leucine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 71
Dependent Claim
9 words
The composition of claim 56, wherein said compound is:
Claim 72
Dependent Claim
13 words
4-diacetyloxy-L-phenylalanyl-L-leucine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 73
Dependent Claim
13 words
4-diacetyloxy-L-phenylalanyl-L-leucine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 74
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 75
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 76
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 77
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-L-isoleucine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 78
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 79
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 80
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 81
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 82
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 83
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: Glycyl-3,4-dipivalyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 84
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 85
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 86
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: Glycyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 87
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: L-leucyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 88
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: L-leucyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 89
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: L-leucyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 90
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: L-leucyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 91
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 92
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 93
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 94
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: L-isoleucyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 95
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 96
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 97
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: phenylalanyl-3,4-diacetyloxy-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 98
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: Phenylalanyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 99
Dependent Claim
21 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 100
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 101
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-ethyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 102
Dependent Claim
22 words
The composition of claim 56, wherein said compound is: 3,4-diacetyloxy-L-phenylalanyl-3,4-diacetyloxy-L-phenylalanine-benzyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 103
Dependent Claim
19 words
The composition of claim 56, wherein said compound is: Poly-3,4-dihydroxy-L-phenylalanine: ##STR38## wherein n represents an integer of 7- 20.
Claim 104
Dependent Claim
19 words
The composition of claim 56, wherein said compound is: Poly-3,4-diacetyloxy-L-phenylalanine: ##STR39## wherein n represents an integer of 7- 20.
Claim 105
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-[n,n-dimethylamino]-glycyl-3,4-dihydroxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 106
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-[n,n-dimethylamino]-glycyl-3,4-diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 107
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-nicotinoyl-3,4-dinicotinoyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 108
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-3-pyridylacetyl-3,4-dihydroxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 109
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-3-pyridylacetyl-3,4-diacetyloxy-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 110
Dependent Claim
23 words
The composition of claim 56, wherein said compound is: 3,4-N,N-dimethylaminoglycyl-L-phenylalanine methyl ester and its HX salt, wherein X represents a pharmaceutically acceptable anion.
Claim 111
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-[n,n-dimethylamino]glycyl-3,4-[N,N-dimethylamino-glycyl]-L-phenylalanine and its M salt, wherein M represents an alkali metal.
Claim 112
Dependent Claim
20 words
The composition of claim 56, wherein said compound is: N-[n,n-diethylaminoglycyl]-3,4-diacetyloxy-L-phenyl-alanine and its M salt, wherein M represents an alkali metal.
Claim 113
Dependent Claim
44 words
The composition of claim 56, 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)
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) | 1980-07-11 | 1981-01-10 | 1981-07-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-11 | 1985-01-10 | 1985-07-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-11 | 1989-01-10 | 1989-07-12 | $7700.00 | Window Closed / Lapsed |