Claims
- 1. A substituted 2-aminoalk-3-enoic acid derivative of formula I ##STR10## wherein R.sub.1 is an aliphatic hydrocarbon radical that is substituted by hydroxy, and R.sub.2 is free or esterified carboxy, or a salt thereof.
- 2. A compound according to claim 1 of formula I, wherein R.sub.1 is mono- or di-hydroxy-lower alkyl, and R.sub.2 is carboxy, lower alkoxycarbonyl, 4- up to and including 7-membered cycloalkoxycarbonyl or phenyl-lower alkoxycarbonyl, any phenyl radicals in the mentioned group R.sub.2 being unsubstituted or mono-, di- or tri-substituted by lower alkyl, lower alkoxy, halogen, cyano and/or by trifluoromethyl, or a salt thereof.
- 3. A compound according to claim 1 of formula I, wherein R.sub.1 is hydroxy-C.sub.1 -C.sub.7 alkyl or dihydroxy-C.sub.2 -C.sub.7 alkyl, and R.sub.2 is carboxy, C.sub.1 -C.sub.4 alkoxycarbonyl, 5- to 7-membered cycloalkoxycarbonyl, or phenyl-C.sub.1 -C.sub.4 alkoxycarbonyl that is unsubstituted or mono- or di-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen having an atomic number of up to and including 35, cyano and/or by trifluoromethyl, or a salt thereof.
- 4. A compound according to claim 1 of formula I, wherein R.sub.1 is hydroxy-C.sub.1 -C.sub.7 alkyl, and R.sub.2 is carboxy, C.sub.1 -C.sub.4 alkoxycarbonyl or phenyl-C.sub.1 -C.sub.4 alkoxycarbonyl that is unsubstituted or mono- or di-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen having an atomic number of up to and including 35, cyano and/or by trifluoromethyl, or a salt thereof.
- 5. A compound according to claim 1 of formula I, wherein R.sub.1 is hydroxy-C.sub.1 -C.sub.7 alkyl, and R.sub.2 is carboxy or C.sub.1 -C.sub.4 alkoxycarbonyl, or a salt thereof.
- 6. A compound according to claim 1 of formula I, wherein R.sub.1 is hydroxymethyl, and R.sub.2 is carboxy or C.sub.1 -C.sub.4 alkoxycarbonyl, or a salt thereof.
- 7. A compound according to claim 1 of formula I, wherein R.sub.1 is hydroxy-C.sub.1 -C.sub.4 alkyl, and R.sub.2 is carboxy or C.sub.1 -C.sub.4 alkoxycarbonyl, or a salt thereof.
- 8. A compound according to claim 1 of formula I, wherein R.sub.1 is hydroxy-C.sub.2 -C.sub.4 alkyl, and R.sub.2 is carboxy, C.sub.1 -C.sub.4 alkoxycarbonyl or a phenyl-C.sub.1 -C.sub.4 alkoxycarbonyl group that is unsubstituted or mono- or di-substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen having an atomic number of up to and including 35, cyano and/or by trifluoromethyl, or a salt thereof.
- 9. A compound according to claim 1 being ethyl 2amino-6-hydroxy-4-phosphonomethyl-hex-3-enoate or a pharmaceutically acceptable salt thereof.
- 10. A compound according to claim 1 selected from 2-amino-6-hydroxy-4-phosphonomethyl-hex-3-enoic acid and ethyl 2-amino-6-hydroxy-4-phosphonomethyl, hept-3-enoate or a pharmaceutically acceptable salt thereof.
- 11. A compound according to claim 1 selected from ethyl 2-amino-7-hydroxy-4-phosphonomethyl-3-hept-3-enoate and 2-amino-7-hydroxy-4-phosphonomethyl-3-hept-3-enoic acid or a pharmaceutically acceptable salt thereof.
- 12. A compound according to claim 1 selected from ethyl 2-amino-4-phosphonomethyl-8-hydroxy-oct-3-enoate and 2-amino-4-phosphonomethyl-8-hydroxy-oct-3-enoic acid or a pharmaceutically acceptable salt thereof.
- 13. A compound according to claim 1 being 2-amino-10-hydroxy-4-phosphonomethyl-dec-3-enoic acid or a pharmaceutically acceptable salt thereof.
- 14. A compound according to claim 1 being ethyl 2(R)-amino-6-hydroxy-4-phosphonomethyl-hex-3-enoate or a pharmaceutically acceptable salt thereof.
- 15. A compound according to claim 1 being benzyl 6-hydroxy-2(R)-amino-4-phosphonomethyl-hex-3-enoate or a pharmaceutically acceptable salt thereof.
- 16. A compound according to claim 1 being 2(R)-amino-6-hydroxy-4-phosphonomethyl-hex-3-enoic acid or a pharmaceutically acceptable salt thereof.
- 17. A compound according to claim 1 being 2-amino-6-hydroxy-5-hydroxymethyl-4-phosphonomethyl-hex-3-enoic acid ethyl ester or a pharmaceutically acceptable salt thereof.
- 18. A compound according to claim 1 being 2-amino-10-hydroxy-4-phosphonomethyl-dec-3-enoic acid ethyl ester or a pharmaceutically acceptable salt thereof.
- 19. A pharmaceutical preparation for use in the treatment of at least one epilepsy, ischaemias, and migraines comprising an effectivement amount in the treatment of an epilepsy, an ischaemia, or a migraine, respectively, of a compound according to claim 1 in the free form or in the form of a pharmaceutically acceptable salt in admixture with a conventional pharmaceutical auxiliary.
- 20. Method for the treatment of epilepsy, ischaemias and/or migraines, wherein a compound according to claim 1 is administered to a warm-blooded organism in need of such treatment.
Priority Claims (1)
Number |
Date |
Country |
Kind |
3479-89 |
Sep 1989 |
CHX |
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Parent Case Info
This is a Continuation of our patent application Ser. No. 08/169,687, filed Dec. 17, 1993, now abandoned, which is a Continuation-in-Part of our patent application Ser. No. 07/851,437, filed Mar. 16, 1992, now U.S. Pat. No. 5,294,734, which in turn is a Continuation-in-Part of our patent application Ser. No. 07/586,352, filed Sep. 21, 1990, now abandoned.
US Referenced Citations (11)
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Country |
0233154 |
Aug 1987 |
EPX |
0302826 |
Feb 1989 |
EPX |
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Oct 1990 |
EPX |
3609818 |
Sep 1987 |
DEX |
53-87314 |
Aug 1978 |
JPX |
2104079 |
Mar 1983 |
GBX |
8706131 |
Oct 1987 |
WOX |
Non-Patent Literature Citations (4)
Entry |
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Park et al "2-Amino 5-Phosphono-3-Pentenoic Acid A New Amino Acid from N-1409 Substance, An Antagonist of Threonine" Agr. Biol Chem. vol. 40.(9) 1905-06 (1976). |
Park et al "Structure of Plumbemycin A and B, Antagonists of L-Threonine from Streptomyces plumbeus" Agr. Biol Chem. vol. 41, 573-579 (1977). |
Kleinrok et al "Preliminary Pharmacological Investigation on 38 Amino Phosphonic Acids and Their Derivatives". Pol. J. Pharmacol & Phar. vol. 37: 275-284 (1985). |
Continuations (1)
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Date |
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Parent |
169687 |
Dec 1993 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
851437 |
Mar 1992 |
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Parent |
586352 |
Sep 1990 |
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