Muscarinic agonists
AssigneeThe University of Toledo
InventorsPhilip G. Dunbar, Graham J. Durant, Wayne P. Hoss, William S. Messer, Jr
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Abstract
Substituted 1,4,5,6 -tetrahydropyrimidine compositions, substituted 1,2,3,6-tetrahydropyrimidine compositions and substituted 3,4,5,6-tetrahydropyridine compositions are disclosed. They are useful for stimulating muscarinic receptors including, for example, treating the symptoms of cognitive disorders, especially impared memory, which are associated with decreased acetylcholine synthesis and cholinergic cell degeneration.
Claims46
A compound having the formula (i), (ii), or (iii) below or a pharmaceutically acceptable salt thereof, ##STR8## wherein A is H or NHR:
- R is H, alkyl of 1-7 carbon atoms, --C(O)--R' or C(O)OR';
- and wherein Z is methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, acetoxy or propynyl carbonyl, and wherein R' is an alkyl group of 1-7 carbon atoms.
A substituted 1,4,5,6-tetrahydropyrimedine wherein in 2 position is not substituted or when substituted, is NHR where R is an alkyl radical of 1-7 carbon atoms and wherein the 5 position is substituted by methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, acetoxy, or propynoxycarbonyl.
A substituted 1,2,3,6-tetrahydropyrimidine in which the 1 position is substituted by an alkyl group of 1 or 7 carbon atoms and the 5 position is substituted by methoxy carbonyl, ethoxy carbonyl, propoxy carbonyl, acetoxy, or propynoxy carbonyl.
A substituted 3,4,5,6-tetrahydropyridine wherein in 2 position is substituted by NHR when R is H or an alkyl group of 1-7 atoms and the 5 position is substituted by methoxy carbonyl, ethoxy carbonyl, propoxy carbonyl, acetoxy, or propynoxy carbonyl.
A compound or salt pharmaceutically acceptable thereof, selected from the group consisting of:
- 5- methoxycarbonyl-1,4,5,6-tetrahydropyrimidine;
- 5-acetoxy-1,4,5,6-tetrahydropyrimidine;
- 1-methyl-5-methoxycarbonyl-1,2,3,6-tetrahydropyrimidine;
- 2-amino-5-methoxycarbonyl-3,4,5,6-tetrahydropyridine;
- 5-ethoxycarbonyl-1,4,5,6-tetrahydropyrimidine;
- 5(3-methyl-1,2,4-oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidine tri-fluoroacetate;
- 2-amino-4-methoxycarbonyl 1,4,5,6-tetrahydropyrimidine and propynyl 1,4,5,6-tetrahydropyrimidine-5-carboxylate hydrochloride.
A compounding having the formula (i), (ii), or (iii) below or a pharmaceutically acceptable salt thereof, ##STR9## wherein A is H or NHR;
- R is H, alkyl of 1-7 carbon atoms, --C(O)--R.sup.1 or C(O)OR.sup.1 ;
- R.sup.1 is an alkyl group of 1-7 carbon atoms;
- and wherein Z is methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, acetoxy, or propynoxycarbonyl.
Dependencies are inferred from the claim text.