US 5,708,014 AGranted

Method for treating anxiety

AssigneeEli Lilly and Company

InventorsNeil C. Bodick, Franklin P. Bymaster, Walter W. Offen, Harlan E. Shannon

Life of this patent

Estimating the term…

Abstract

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

Claims7

Dependent claims

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.

124 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/336,454Filed 9 Nov 1994 · continuation in part
Priority: 31 Oct 1994
Granted: 13 Jan 1998
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

A61K 31/5377
1,4-Oxazines, e.g. morpholine: not condensed and containing further heterocyclic rings, e.g. timolol
A61K 31/439
Having six-membered rings with one nitrogen as the only ring hetero atom: the ring forming part of a bridged ring system, e.g. quinuclidine
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
A61K 31/444
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone

Family

Serial332,186Parent of this continuation-in-part · filed 31 Oct 1994
US 5,488,056 AParent of this continuation-in-part
US 5,708,014 AThis patent

From the US filing history. Foreign family members aren’t listed.

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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.

124 more elements

Facts

Application

08/336,454Filed 9 Nov 1994 · continuation in part

Priority

31 Oct 1994

Granted

13 Jan 1998

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

A61K 31/5377
1,4-Oxazines, e.g. morpholine: not condensed and containing further heterocyclic rings, e.g. timolol
A61K 31/439
Having six-membered rings with one nitrogen as the only ring hetero atom: the ring forming part of a bridged ring system, e.g. quinuclidine
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
A61K 31/444
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone