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US 5,672,746 AGranted
Antiproliferative and neurotrophic molecules
AssigneesAmerican Biogenetic Sciences, Inc., University College Dublin
InventorsHeinz Nau, Ciaran M. Regan
Life of this patent
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Abstract
Neurotrophic and antiproliferative compounds related to the antiepileptic drug valproate are provided. These compounds are useful for promoting neuronal function as in neurodegenerative disorders and for treating neoplastic disease.
Claims15
Compounds of formula (I) ##STR11## wherein R.sup.1 is --C.tbd.CH, --CH.dbd.CH.sub.2, or --CH.sub.2 --CH.sub.3,
- R.sup.2 is a saturated, unsaturated, branched and/or unbranched C.sub.1 -C.sub.30 alkyl group, optionally further comprising an aliphatic or aromatic C.sub.3-9 cyclohydrocarbon or heterocyclic group comprising 3 to 9 atoms;
- and
- M is a hydrogen or a metal atom,
- and enantiomeres thereof and pharmaceutical acceptable salts thereof;
- with the proviso that the compound of formula (I) is not 2-n-propyl-4-pentynoic acid, 2-benzylpentanoic acid, 4,4'-dien-valproic acid or 2-n-propyl-4-pentenoic acid (4-en-VPA), and when R.sup.1 is --CH.sub.2 --CH.sub.3, R.sup.2 is C.sub.5 to C.sub.30.
2 more elements
A method of preparing compounds having the general formula (I) ##STR12## wherein R.sup.1 is --C.tbd.CH, --CH.dbd.CH.sub.2, or --CH.sub.2 --CH.sub.3,
- R.sup.2 is a saturated, unsaturated, branched and/or unbranched C.sub.1-30 alkyl group, optionally substituted with an aliphatic or aromatic C.sub.3-9 cyclohydrocarbon or heterocyclic group;
- and
- M is a hydrogen or a metal atom, comprising;
- combining a malonic acid diester with a first halide having the general formula (VII)
- R.sup.2 --X (VII)
- wherein R.sup.2 has the meaning given previously;
- or halogen, to form a 2-alkyl malonic acid diester, and combining the 2-alkyl malonic acid diester with a second halide having the general formula (VIII)
- R.sup.1 --CH.sub.2 --X (VIII)
- wherein R.sup.1 has the meaning given previously;
- or combining the malonic acid diester with the second halide having the general formula (VIII) to form a 2-alkyl malonic acid diester;
- and
- combining the first halide having the general formula (VII) to form a compound of formula (IX) ##STR13## wherein R.sup.5 is an alkyl group;
- and hydrolyzing and decarboxylating the compound of formula (IX) to form the compound of formula (I);
- and optionally converting the compound of formula (I) to a salt.
11 more elements
Dependencies are inferred from the claim text.