US4477391A
Expired / Lapsed
US
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Amino acid isomers, their production and their medicinal use
Assignee: Individual
•
Filing: 1982-03-08
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Granted: 1984-10-16
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Expires: 2002-03-08
Abstract
Abstract The (-)-D-isomers of compounds of the general formula ##STR1## in which X stands for an acidic radical, especially a radical of phosphonic acid, sulphonic acid, boronic acid or tetrazole, R stands for an alkylene, alkenylene or alkynylene radical with 3 or more carbon atoms, preferably 3 to 6 carbon atoms, or a C 3 to C 7 cycloalkyl radical, and A and B independently of each other stand for a hydrogen atom or a lipophilic radical, especially an ester radical, or salts thereof, or pharmaceutically acceptable bioprecursors thereof, especially (-)-D-aminophosphonopentanoic acid and (-)-D-aminophosphonoheptanoic acid, find use in the treatment of diseases of the central nervous system. The compound aminophosphonoheptanoic acid is also novel as a racemic mixture and the present invention also relates to that compound in racemic form which may be used in the same way as the said (-)-D-isomers.
Inventors
- 👤 James F. Collins
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:39
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3808; A; A61; A61P; A61P25/00; A61P25/08; C07F9/40; C07F9/4003; C07F9/4006
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
128 words
A process for the production of a compound of formula (I) ##STR19## X stands for a phosphonic acid radical, R stands for an alkylene, alkenylene, or alkynylene radical with 3 or more carbon atoms, or a C 3 to C 7 cycloalkyl radical, and A and B independently of each other stand for a hydrogen atom or an ester group, or a salt thereof comprising reacting (a) a dibromo compound of the formula Br--R--Br (II) with a compound of the formula ##STR20## R' stands for an alkyl group, M.sup.⊕ stands for an alkali metal cation, and heating the resulting compound of the general formula ##STR21## with diethyl acetamidomalonate, and subjecting the resulting condensation product of the formula ##STR22## to decarboxylation to give a compound of the formula ##STR23##
Claim 2
Dependent Claim
128 words
A process for the production of a compound of formula (I) ##STR19## X stands for a phosphonic acid radical, R stands for an alkylene, alkenylene, or alkynylene radical with 3 or more carbon atoms, or a C 3 to C 7 cycloalkyl radical, and A and B independently of each other stand for a hydrogen atom or an ester group, or a salt thereof comprising reacting (a) a dibromo compound of the formula Br--R--Br (II) with a compound of the formula ##STR20## R' stands for an alkyl group, M.sup.⊕ stands for an alkali metal cation, and heating the resulting compound of the general formula ##STR21## with diethyl acetamidomalonate, and subjecting the resulting condensation product of the formula ##STR22## to decarboxylation to give a compound of the formula ##STR23##
Claim 3
Dependent Claim
16 words
A process according to claim 1 wherein R' is ethyl and M.sup.⊕ is a sodium cation.
Claim 4
Dependent Claim
13 words
A process according to claim 2 wherein compound (IV) is heated in ethanol.
Claim 5
Dependent Claim
15 words
A process according to claim 2 wherein compound (V) is decarboxylated in boiling hydrochloric acid.
Claim 6
Dependent Claim
14 words
A process according to claim 2 wherein compound (V) is decarboxylated with iodotrimethyl silane.
Claim 7
Dependent Claim
13 words
A process according to claim 5 wherein compound (IV) is heated in ethanol.
Claim 8
Dependent Claim
28 words
A process according to claim 2 in which the (-)-D-isomer is separated by reacting the final product with an optically active base and separating out the salts formed.
Claim 9
Dependent Claim
39 words
A process according to claim 7 in which the optically active base is L-lysine and the process includes the steps of separating the salt of the (-)-D-isomer by crystallization followed by decomposition of said salt to obtain the (-)-D-isomer.
Claim 10
Dependent Claim
29 words
A process according to claim 1 wherein the (-)-D-isomer is separated by recycling the product of reaction (a) with an optically active base and separating out the salts formed.
Claim 11
Dependent Claim
43 words
A process according to claim 9 wherein the (-)-D-isomer is separated by reacting the product of reaction (a) with L-lysine, thereby forming diastereomer salts, separating the salt containing the (-)-D-isomer by crystallisation, followed by decomposition of the said salt to obtain the (-)-D-isomer.
Claim 12
Dependent Claim
19 words
A process according to claim 1 wherein R is an n-pentyl radical and A and B are hydrogen atoms.
Claim 13
Dependent Claim
31 words
A process according to claim 1 including the step of converting at least one of an amino group or a carboxylic acid group carrying an ester group to a salt thereof.
References Cited (Backward Citations)
US2934561A
Cited
US4168963A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-16 | 1988-04-16 | 1988-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-16 | 1992-04-16 | 1992-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-16 | 1996-04-16 | 1996-10-16 | $7700.00 | Window Closed / Lapsed |