# US 5,708,014 A · Method for treating anxiety

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- Number: US 5,708,014 A
- Document ID: US5708014A
- Status: Granted
- Kind: A
- Application number: 08/336,454
- Filed: 1994-11-09
- Granted: 1998-01-13
- Earliest claimed: 1994-10-31
- Assignees: Eli Lilly and Company
- Inventors: Neil C. Bodick; Franklin P. Bymaster; Walter W. Offen; Harlan E. Shannon
- Web page: https://patentgrep.com/patent/US5708014A

## CPC

- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 31/439: the ring forming part of a bridged ring system, e.g. quinuclidine (8-azabicyclo [3.2.1] octanes A61K31/46)
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61K 31/4545: containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
- A61K 31/46: 8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
- A61K 31/55: having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61P 25/20: Hypnotics; Sedatives
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a method for treating anxiety in humans using of Formula I herein disclosed compounds.

## Claims

### Claim 1

A method for treating anxiety in humans comprising administering to a human in need thereof, an antianxiety dose of a compound of Formula I: ##STR2## wherein Z.sup.1 is oxygen or sulphur;
R is hydrogen, halogen, amino, --NHCO--R.sup.2, C.sub.3-7 -cycloalkyl, C.sub.4-10 -(cycloalkylalkyl), --Z.sup.2 -C.sub.3-7 -cycloalkyl optionally substituted with C.sub.1-6 -alkyl, --Z.sup.2 -C.sub.4-10 -(cycloalkylalkyl), --Z.sup.2 -C.sub.4-10 -(cycloalkenylalkyl), --Z.sup.2 -C.sub.4-10 -(methylenecycloalkyl-alkyl), --NH--R.sup.2, --NR.sup.2 R.sup.3, --NH--OR.sup.2, phenyl, phenoxy, benzyl, benzyloxycarbonyl, tetrahydronaphthyl, indenyl, X, R.sup.2, --Z.sup.2 R.sup.2, --SOR.sup.2, --SO.sub.2 R.sup.2, --Z.sup.2 --R.sup.2 --Z.sup.3 --R.sup.3, --Z.sup.2 --R.sup.2 -Z.sup.3 --R.sup.3 --Z.sup.4 --R.sup.4, --Z.sup.2 --R.sup.2 CO--R.sup.3, --Z.sup.2 --R.sup.2 --CO.sub.2 --R.sup.3, Z.sup.2 --R.sup.2 --O.sub.2 C--R.sup.3, --Z.sup.2 --R.sup.2 --CONH--R.sup.3, --Z.sup.2 --R.sup.2 --NHCOR.sup.3, --Z.sup.2 --R.sup.2 --X, --Z.sup.2 --R.sup.2 --Z.sup.3 --X, wherein Z.sup.2, Z.sup.3, and Z.sup.4 independently are oxygen or sulphur, and R.sup.2, R.sup.3 and R.sup.4 independently are straight or branched C.sub.1-15 -alkyl, straight or branched C.sub.2-15 -alkenyl, straight or branched C.sub.2-15 -alkynyl, each of which is optionally substituted with halogen(s), --OH, --CN, --CF.sub.3, --SH, --COOH, --NH--R.sup.2, --NR.sup.2 R.sup.3, C.sub.1-6 alkyl ester, one or two phenyl, phenoxy, benzoyl or benzyloxycarbonyl wherein each aromatic group is optionally substituted with one or two halogen, --CN, C.sub.1-4 -alkyl or C.sub.1-4 -alkoxy, and X is a 5-membered heterocyclic group containing one to four N, O or S atom(s) or a combination thereof, which heterocyclic group is optionally substituted at carbon or nitrogen atom(s) with straight or branched C.sub.1-6 -alkyl, phenyl, benzyl or pyridine, or a carbon atom in the heterocyclic group together with an oxygen atom form a carbonyl group, or which heterocyclic group is optionally fused with a phenyl group; and
R.sup.5 and R.sup.6 may be present at any available position, and independently are hydrogen, straight or branched C.sub.1-5 -alkyl, straight or branched C.sub.2-5 -alkenyl, straight or branched C.sub.2-5 -alkynyl, straight or branched C.sub.1-10 -alkoxy, straight or branched C.sub.1-5 -alkyl substituted with --OH, halogen, --NH.sub.2 or carboxy;
R.sup.1 is hydrogen, straight or branched C.sub.1-5 -alkyl, straight or branched C.sub.2-5 -alkenyl or straight or branched C.sub.2-5 -alkynyl; or
a pharmaceutically acceptable salt or solvate thereof;
provided that the compound of Formula I is not a compound selected from the group consisting of
3-(3-METHOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-ETHOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-PROPOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-BUTOXY-1,2,5-THIADIAZOL-4-YL)1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-ISOPROPOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-CYCLOPROPYLMETHOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLP YRIDINE
3-(3-PENTOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-ISOBUTOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-(3-BUTENOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDIN E
3-(3-(BUT-2-YNOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDI NE
3-(3-(3-METHYLBUTOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYR IDINE
3-(3-HEXYLOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-(PROP-2-YNOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRID INE
3-(3-BENZYLOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-CHLORO-1,2,5-THIADIAZOL-4-YL -1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-CHLORO-1,2,5-THIADIAZOL-4-YL -1,2,5,6-TETRAHYDROPYRIDINE
3-(3-BUTOXY-1,2,5-THIADIAZOL-4-YL -1,2,5,6-TETRAHYDROPYRIDINE
3-(3-ETHOXY-1,2,5-THIADIAZOL-4-YL -1,2,5,6-TETRAHYDRO-1-ETHYLPYRIDINE
3-(3-CHLORO-1,2,5-THIADIAZOL-4-YL -1,2,5,6-TETRAHYDRO-1-ETHYLPYRIDINE
3-(3-METHOXYETHOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDI NE
3-(3-HEPTYLOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-(3-PENTYNYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
3-(3-(4-PENTENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
3-(3-(2-PROPENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
3-(3-OCTYLOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-(3-HEXYNYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRID INE
3-(3-(3-BUTENYL-2-OXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYL-P YRIDINE
3-(3-(4-HEXENYLOXY(-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRID INE
3-(3-(3-HEXENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRID INE
3-(3-(2-PENTENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
3-(3-(2-HEXENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRID INE
3-(3-(5-HEXENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRID INE
3-(3-(3-HEXENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRID INE
3-(1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-DIMETHYLAMINO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDI NE
3-(3-HEXYLAMINO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-HEXYLOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-DEUTEROMETHYLPYRI DINE
1,2,5,6-TETRAHYDRO-3-(3-HEXYLOXY-1,2,5-THIADIAZOL-4-YL)-PYRIDINE
3-(3-(2-(2-METHOXYETHOXY)-ETHOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO -1-METHYLPYRIDINE
3-(3-(3-ETHOXY-1-PROPOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6,-TETRAHYDRO-1-METH YLPYRIDINE
3-(2-ETHOXYETHOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDI NE
3-(3-(2-BUTOXYETHOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYR IDINE
3-(3-(2-(2-BUTOXYETHOXY)-ETHOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO- 1-METHYLPYRIDINE
3-(3-(2-(2-ETHOXYETHOXY)-ETHOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO- 1-METHYLPYRIDINE
3-(3-BUTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-METHYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-PENTYL-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-PROPYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-HEXYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-PENTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-ETHYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-OCTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-PROPYL-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-HEPTYL-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-(5-HEXENYL)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-OCTYL-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYPYRIDINE
3-(3-(2-METHYL)-BUTYL-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYR IDINE
3-(3-METHYLCYCLOPROPYL-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPY RIDINE
3-(3-CYCLOPENTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
3-(3-(1-ETHYLTHIO-2-METHOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-ME THYLPYRIDINE
3-(3-(3-CHLORO-1-PROPYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-ME THYLPYRIDINE
3-(3-(2-METHOXYETHOXY)-ETHYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO -1-METHYLPYRIDINE
3-(3-(3-CYANO-1-PROPYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-MET HYL PYRIDINE
3-(3-BENZYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-(2-ETHOXY-1-ETHYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-MET HYLPYRIDINE
3-(3-(4-PENTYNYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYR IDINE
3-(3-(2-(2-ETHOXYMETHOXY)-ETHYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHY DRO-1-METHYLPYRIDINE
3-(3-(5-CYANO-1-PENTYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-MET HYLPYRIDINE
3-(3-(3-PHENYL-1-PROPYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-ME THYLPYRIDINE
3-(3-(2-PHENOXYETHYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHY LPYRIDINE
3-(3-(4-CYANOBUTYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLP YRIDINE
3-(3-(2-ETHYLBUTYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLP YRIDINE
3-(3-CYCLOHEXYLMETHYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHY LPYRIDINE
3-(3-(8-HYDROXYOCTYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHY LPYRIDINE
3-(3-(7-OCTENYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
3-(3-CYCLOPROPYLMETHYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METH YLPYRIDINE
3(3-CYCLOPROPYLMETHYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METH YLPYRIDINE
3-(3-(3-BUTENYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
3-(3-(4-PENTENYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYR IDINE
3-(4-ISOHEXYLOXY-1,2,5-THIADIAZOL-3-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
1-METHYL-1,2,5,6-TETRAHYDRO-3-((4-CYCLOPENTYLPROPYL)OXY)-1,2,5-THIADIAZOL-3 -YL)PYRIDINE
1-METHYL-1,2,5,6-TETRAHYDRO-3-(4-ISOHEPTYLOXY-1,2,5-THIADIAZOL-3-YL)PYRIDIN E
1-METHYL-1,2,5,6-TETRAHYDRO-3-(4((2-CYCLOHEXYLETHYL)OXY)-1,2,5-THIADIAZOL-3 -YL)PYRIDINE MALEATE
1,2,5,6-TETRAHYDRO-1-METHYL-3-(4-(1-METHYLHEXLOXY)-1,2,5-THIADIAZOL-3-YL)PY RIDINE
3-(4-(1-ETHYLPENTYLOXY)-1,2,5-THIADIAZOL-3-YL)-1,2,5,6-TETRAHYDRO-1-METHYLP YRIDINE
3-(4-(1-ETHYLBUTOXY)-1,2,5-THIADIAZOL-3-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
1,2,5,6-TETRAHYDRO-1-METHYL-3-(4-(1-METHYLPENTYLOXY)-1,2,5-THIADIAZOL-3-›)! YL)PYRIDINE
1-METHYL-3-(4-(5-HEXENYLOXY)-1,2,5-THIADIAZOL-3-YL)-1,2,5,6-TETRAHYDROPYRID INE
1,2,5,6-TETRAHYDRO-1-METHYL-3-(4-(2-METHYLBUTOXY)-1,2,5-THIADIAZOL-3-YL)PYR IDINE
1,2,5,6-TETRAHYDRO-1-METHYL-3-(4-(2-METHYLPENTYLOXY)-1,2,5-THIADIAZOL-3-YL) PYRIDINE
1,2,5,6-TETRAHYDRO-1-METHYL-3-(4-(2,2,2-TRIFLUOROETHOXY)-1,2,5-THIADIAZOL-3 -YL)PYRIDINE
1-METHYL-1,2,5,6-TETRAHYDRO-3-(4-(3-METHYLPENTYLOXY)-1,2,5-THIADIAZOL-3-YL) PYRIDINE
3-(3-(3-METHYL-2-BUTENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDO-1-MET HYLPYRIDINE
3-(3-ISOBUTOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
1. 2,5,6-TETRAHYDRO-1-METHYL-3-(4-(2-METHYLBUTOXY)-1,2,5-THIADIAZOL-3-YL)PY RIDINE
3-(3-(3-HYDROXYPROPOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLP YRIDINE
1,6-DIMETHYL-3-(3-HEXYLOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDIN E
3-(3-(PHENETHYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRI DINE
3-(3-(4,4,4-TRIFLUOROBUTOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5-THIADIAZOL-4-YL)- 1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-(3,3,3-TRIFLUOROPROPYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO- 1-METHYLPYRIDINE
3-(3-PROPYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDINE
3-(3-BUTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDINE
3-(3-BUTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1,1-DIMETHYLPYRIDI NIUM IODIDE
1,6-DIMETHYL-3-(3-BUTOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDINE
3-(3-(3-METHYL-2-BUTENYLOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDO-1-MET HYL PYRIDINE
3-(3-ISOBUTOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
1,2,5,6-TETRAHYDRO-1-METHYL-3-(4-(2-METHYLBUTOXY)-1,2,5-THIADIAZOL-3-YL)PYR IDINE
3-(3-(3-HYDROXYPROPOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLP YRIDINE
1,6-DIMETHYL-3-(3-HEXYLOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDIN E
3-(3-(4,4,4-TRIFLUOROBUTOXY)-1,2,5-THIADIAZOL-4-YL)-1,2,5-THIADIAZOL-4-YL)- 1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-(3,3,3-TRIFLUOROPROPYLTHIO)-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO- 1-METHYLPYRIDINE
3-(3-PROPYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1-METHYLPYRIDINE
3-(3-PROPYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDINE
3-(3-BUTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDINE
3-(3-BUTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDRO-1,1-DIMETHYLPYRIDI NIUM IODIDE
1,6-DIMETHYL-3-(3-BUTYLTHIO-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDI NE
1,6-DIMETHYL-3-(3-BUTOXY-1,2,5-THIADIAZOL-4-YL)-1,2,5,6-TETRAHYDROPYRIDINE; and
a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A method of claim 1, wherein Z.sup.1 is sulfur.

### Claim 3 (depends on 2)

A method of claim 2, wherein R.sup.5 and R.sup.6 are each hydrogen.

### Claim 4 (depends on 2)

A method of claim 2 wherein R.sup.1 is hydrogen or straight or branched C.sub.1-5 -alkyl; R.sup.5 and R.sup.6 independently are selected from the group consisting of hydrogen, methyl, and methoxy.

### Claim 5 (depends on 1)

A method of claim 1, wherein Z.sup.1 is oxygen.

### Claim 6 (depends on 5)

A method of claim 5 wherein R.sup.5 and R.sup.6 are each hydrogen.

### Claim 7 (depends on 5)

A method of claim 5 wherein R.sup.1 is hydrogen or straight or branched C.sub.1-5 -alkyl; R.sup.5 and R.sup.6 independently are selected from the group consisting of hydrogen, methyl, and methoxy.