Claims
- 1. A compound of formula I, ##STR10## wherein R.sub.1 is lower alkanoyloxy-lower alkyl or benzoyloxy-lower alkyl, lower alkoxy-lower alkyl or phenyl-lower alkoxy-lower alkyl, 6-aminohexyl, lower alkyl 6-aminohexyl or di-lower alkyl 6-aminohexyl and R.sub.2 is carboxy, lower alkoxycarbonyl, 4- up to and including 7-membered cycloalkoxycarbonyl or phenyl-lower alkoxycarbonyl, any phenyl radicals in R.sub.1 and/or 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.
- 2. A compound according to claim 1 of formula I, wherein R.sub.1 is (a) C.sub.2 -C.sub.7 alkanoyloxy-C.sub.1 -C.sub.7 alkyl, (b) benzoyloxy-C.sub.1 -C.sub.7 alkyl that is unsubstituted or mono- or di-substituted in the phenyl moiety 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, (c) C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.7 alkyl, (d) a phenyl-C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.7 alkyl group that is unsubstituted or mono- or di-substituted in the phenyl moiety 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 (e) 6-aminohexyl, C.sub.1 -C.sub.4 alkyl 6-aminohexyl or di-C.sub.1 -C.sub.7 alkyl 6-aminohexyl, 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.
- 3. A compound according to claim 1 of formula I, wherein R.sub.1 is (a) benzoyloxy-C.sub.1 -C.sub.7 alkyl that is unsubstituted or mono- or di-substituted in the phenyl moiety 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, (b) phenyl-C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.7 alkyl that is unsubstituted or mono- or di-substituted in the phenyl moiety 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 (c) amino-6-aminohexyl, 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.
- 4. A compound according to claim 1 of formula I, wherein R.sub.1 is C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.7 alkyl, benzoyloxy-C.sub.1 -C.sub.4 alkyl or 6-aminohexyl, and R.sub.2 is carboxy or C.sub.1 -C.sub.4 -alkoxycarbonyl, or a salt thereof.
- 5. A compound according to claim 1 of formula I, wherein R.sub.1 is methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-benzoyloxyethyl, benzyloxymethyl, 2-benzyloxyethyl, or 6-aminohexyl, 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 6-aminohexyl, 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 C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, phenyl-C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 -alkyl, or benzoyloxy-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 C.sub.1 -C.sub.4 alkoxy-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 selected from the group consisting of,
- 2-amino-6-methoxy-4-phosphonomethyl-hex-3-enoic acid ethyl ester,
- 2-amino-6-methoxy-4-phosphonomethyl-hex-3-enoic acid,
- 2,10-diamino-4-phosphonomethyl-dec-3-enoic acid,
- 2,10-diamino-4-phosphonomethyl-dec-3-enoic acid ethyl ester,
- 2-amino-5-benzyloxy-4-phosphonomethyl-pent-3-enoic acid ethyl ester,
- 5-ethoxy-2-amino-4-phosphonomethyl-penten-3-oic acid ethyl ester,
- 2-amino-7-ethoxycarbonylmethoxy-4-phosphonomethyl-hept-3-enoic acid,
- 2-amino-6-ethoxycarbonylmethoxy-4-phosphonomethyl-hex-3-enoic acid, and
- benzyl 6-acetoxy-2-amino-4-phosphonomethyl-hex-3-enoate,
- or a pharmaceutically acceptable salt thereof.
- 10. A pharmaceutical preparation containing an amount therapeutically effective in the treatment of epilepsy, ischaemia or migraine of a compound according to claim 1 in the free form or in the form of a pharmaceutically acceptable salt in admixture with pharmaceutically acceptable auxiliaries.
- 11. Method for the treatment of epilepsy, ischaemia and/or migraine, comprising administering a therapeutically effective amount of a compound according to claim 1 to a warm-blooded organism in need of such treatment.
Priority Claims (1)
Number |
Date |
Country |
Kind |
3479/89-6 |
Sep 1989 |
CHX |
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Parent Case Info
This is a continuation-in-part of our co-pending U.S. patent application Ser. No. 07/586,352, filed Sep. 21, 1990 now abandoned.
US Referenced Citations (10)
Foreign Referenced Citations (8)
Number |
Date |
Country |
233154 |
Feb 1986 |
EPX |
0233154 |
Aug 1987 |
EPX |
0302826 |
Jul 1988 |
EPX |
391850 |
Apr 1989 |
EPX |
3609818 |
Mar 1986 |
DEX |
53-87314 |
Jan 1977 |
JPX |
8706131 |
Oct 1987 |
WOX |
2104079 |
Mar 1983 |
GBX |
Non-Patent Literature Citations (3)
Entry |
Park, et al., "Structure of Plumbemycin A and B, Antagonists of L-Threonine from Streptomyces plumbeus"; Agr. Biol. Chem. 41: 573-579 (1977). |
Kleinrok, et al., "Preliminary Pharmacological Investigation on 38 Aminophosphonic Acids and Their Derivatives" Pol. J. Pharma. 37:275-284 (1985). |
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. 40(9):1905-1906 (1976). |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
586352 |
Sep 1990 |
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