Heterocyclic compounds and their use
First Claim
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1. A compound of formula I ##STR7## wherein Z1 is oxygen or sulphur;
- R is --Z2 --C3-7 -cycloalkyl optionally substituted with C1-6 -alkyl, --Z2 --C4-10 -(cycloalkylalkyl), --Z2 --C4-10 -(cycloalkenylalkyl), or --Z2 --C4-10 -(methylenecycloalkylalkyl), wherein Z2 is oxygen or sulfur;
R5 and R6 may be present at any appropriate position and independently are (1) hydrogen, (2) straight or branched C1-5 -alkyl, (3) straight or branched C2-5 -alkenyl, (4) straight or branched C2-5 -alkynyl, (5) straight or branched C1-10 -alkoxy, (6 straight or branched C1-5 -alkyl substituted with --OH, (7) --OH, (8) halogen, (9) --NH2 or (10) carboxy; and
R1 is hydrogen, straight or branched C1-5 -alkyl, straight or branched C2-5 -alkenyl or straight or branched C2-5 -alkynyl;
ora pharmaceutically acceptable salt thereof.
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Abstract
The present invention relates to therapeutically active azabicyclic compounds of formula (1), wherein Z1 is oxygen or sulphur, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful as stimulants of the cognitive function of forebrain and hippocampus of mammals and especially in the treatment of Alzheimer'"'"'s disease, severe painful conditions and glaucoma. ##STR1##
17 Citations
34 Claims
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1. A compound of formula I ##STR7## wherein Z1 is oxygen or sulphur;
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R is --Z2 --C3-7 -cycloalkyl optionally substituted with C1-6 -alkyl, --Z2 --C4-10 -(cycloalkylalkyl), --Z2 --C4-10 -(cycloalkenylalkyl), or --Z2 --C4-10 -(methylenecycloalkylalkyl), wherein Z2 is oxygen or sulfur; R5 and R6 may be present at any appropriate position and independently are (1) hydrogen, (2) straight or branched C1-5 -alkyl, (3) straight or branched C2-5 -alkenyl, (4) straight or branched C2-5 -alkynyl, (5) straight or branched C1-10 -alkoxy, (6 straight or branched C1-5 -alkyl substituted with --OH, (7) --OH, (8) halogen, (9) --NH2 or (10) carboxy; and R1 is hydrogen, straight or branched C1-5 -alkyl, straight or branched C2-5 -alkenyl or straight or branched C2-5 -alkynyl;
ora pharmaceutically acceptable salt thereof. - View Dependent Claims (2, 3, 4, 5, 6)
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7. A compound of formula I ##STR8## wherein Z1 is oxygen or sulphur;
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R is --Z2 R2, wherein Z2 is oxygen or sulphur, and R2 is straight or branched C1-15 -alkyl, straight or branched C2-15 -alkenyl, or straight or branched C2-15 -alkynyl, each of which is substituted with --SH, --COOH, --NH--R2, or --NR2 R3 wherein R3 is straight or branched C1-15 -alkyl, straight or branched C2-15 -alkenyl, or straight or branched C2-15 -alkynyl; R5 and R6 may be present at any appropriate position and independently are (1) hydrogen, (2) straight or branched C1-5 -alkyl, (3) straight or branched C2-5 -alkenyl, (4) straight or branched C2-5 -alkynyl, (5) straight or branched C1-10 -alkoxy, (6) straight or branched C1-5 -alkyl substituted with --OH, (7) --OH, (8) halogen, (9) --NH2 or (10) carboxy; and R1 is hydrogen, straight or branched C1-5 -alkyl, straight or branched C2-5 -alkenyl or straight or branched C2-5 -alkynyl;
ora pharmaceutically acceptable salt thereof. - View Dependent Claims (8, 9, 10, 11, 12, 13)
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14. A compound of formula I ##STR9## wherein Z1 is oxygen or sulphur;
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R is --Z2 --X, wherein Z2 is oxygen or sulphur and X is a heterocyclic group selected from the group consisting of 1,3-dioxolanyl, pyridyl, thienyl, pyrrolidonyl, oxazolidonyl, thiazolidonyl, pyrrolidinyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, tetrazolyl, thiazolyl and oxazolyl, which heterocyclic group is optionally substituted at carbon or nitrogen atom(s) with straight or branched C1-6 -alkyl, C1-6 -alkoxy, C1-6 -alkylthio, phenyl, benzyl or pyridine; and R5 and R6 may be present at any appropriate position and independently are (1) hydrogen, (2) straight or branched C1-5 -alkyl, (3) straight or branched C2-5 -alkenyl, (4) straight or branched C2-5 -alkynyl, (5) straight or branched C1-10 -alkoxy, (6) straight or branched C1-5 -alkyl substituted with --OH, (7) --OH, (8) halogen, (9) --NH2 or (10) carboxy; R1 is hydrogen, straight or branched C1-5 -alkyl, straight or branched C2-5 alkenyl or straight or branched C2-5 -alkynyl;
ora pharmaceutically acceptable salt thereof. - View Dependent Claims (15, 16, 17, 18, 19, 20)
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21. A compound of formula I ##STR10## wherein Z1 is oxygen or sulphur;
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R is --Z2 R2, wherein Z2 is oxygen or sulphur and R2 is an indenyl or naphthalylyl group; R5 and R6 may be present at any appropriate position and independently are (1) hydrogen, (2) straight or branched C1-5 -alkyl, (3) straight or branched C2-5 -alkenyl, (4) straight or branched C2-5 -alkynyl, (5) straight or branched C1-10 -alkoxy, (6) straight or branched C1-5 -alkyl substituted with --OH, (7) --OH, (8) halogen, (9) --NH2 or (10) carboxy; R1 is hydrogen, straight or branched C1-5 -alkyl, straight or branched C2-5 -alkenyl or straight or branched C2-5 -alkynyl;
ora pharmaceutically acceptable salt thereof. - View Dependent Claims (22, 23, 24, 25, 26)
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27. A compound of formula I ##STR11## wherein Z1 is oxygen or sulphur;
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R is --Z2 --R2 CO--R3, --Z2 --R2 --CO2 --R3 or --Z2 --R2 --O2 C--R3, wherein Z2 is oxygen or sulphur, and R2 and R3 independently are unsubstituted, straight or branched C1-5 -alkyl, unsubstituted, straight or branched C2-5 -alkenyl, or unsubstituted, straight or branched C2-5 -alkynyl; and R5 and R6 may be present at any appropriate position and independently are (1) hydrogen, (2) straight or branched C1-5 -alkyl, (3) straight or branched C2-5 -alkenyl, (4) straight or branched C2-5 -alkynyl, (5) straight or branched C1-10 -alkoxy, (6) straight or branched C1-5 -alkyl substituted with --OH, (7) --OH, (8) halogen, (9) --NH2 or (10) carboxy; R1 is hydrogen, straight or branched C1-5 -alkyl, straight or branched C2-5 -alkenyl or straight or branched C2-5 -alkynyl;
ora pharmaceutically acceptable salt thereof. - View Dependent Claims (28, 29, 30, 31, 32)
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33. A compound which is:
3-(3-(4-Phenylthiobutylthio)-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine;
or a pharmaceutically acceptable salt thereof.
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34. A compound which is:
3-(3-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine or a pharmaceutically acceptable salt thereof.
Specification