Degussa Aktiengesellschaft

Deutsche Gold- Und Silber-scheideanstalt Vormals Roessler

Vladimir Jakovlev

Jurgen Engel

Klaus Thiemer

Walter Von Bebenburg

Norbert Schulmeyer

Axel Kleemann

Bernd Nickel

Gerhard Scheffler

Gerhard Oepen

There are disclosed pyridine-2-ethers and pyridine-2-thioethers having a nitrogen-containing cycloaliphatic ring corresponding to the formula ##STR1## the pyridine-N-oxides and/or amine oxides thereof and the pharmaceutically acceptable salts thereof. The compounds show analgesic activity.

Analgesic pyridine-2-ethers or pyridine-2-thioethers having a

There are prepared new pharmacologically active compounds of the formula: ##STR1## In formula I R.sub.1 is a phenyl radical, pyridyl radical, a pyrimidyl group, or pyrazinyl radical, or a phenyl radical, pyridiyl radical, pyrimidyl radical, or pyrazinyl radical substituted by the radicals R.sub.3 and R.sub.4 which are the same or different and are hydrogen, fluorine, chlorine, bromine, trifluoromethyl, hydroxyl, C.sub.1 -C.sub.6 -alkyl groups C.sub.1 -C.sub.6 -alkoxy groups, C.sub.3 -C.sub.6 -alkenyloxy groups, C.sub.3 -C.sub.6 -cycloalkyloxy groups, phenyl-C.sub.1 -C.sub.4 -alkoxy groups, C.sub.1 -C.sub.6 -alkylmercapto groups, the nitro group, the amino group, C.sub.1 -C.sub.6 -dialkylamino groups, C.sub.2 -C.sub.6 -alkanoyl groups, C.sub.2 -C.sub.6 -alkanoylamino groups, or C.sub.2 -C.sub.6 -alkanoyloxy groups and R.sub.2 is the adamantyl group, the 3,3-dimethyl-bicyclo[2.2.1]hept-2-yl radical, a saturated C.sub.3 -C.sub.16 -cycloalkenyl radical and alk is a straight or branched C.sub.1 -C.sub.6 alkyl chain.

N-Phenyl-N-'-cycloalkylalkanoylpiperazine useful as analgetics and

There are prepared compounds corresponding to the general formula ##STR1## in which R.sup.1 is a hydrogen atom, a C.sub.2 to C.sub.6 -alkanoyl group, a C.sub.3 to C.sub.6 -alkenoyl group, a C.sub.3 to C.sub.6 -cycloalkyl carbonyl group, a benzoyl group, an alkoxybenzoyl group, a nicotinoyl group, a thienyl carbonyl group, a furyl carbonyl group, a phenylacetyl group or a C.sub.1 to C.sub.4 -alkoxyphenyl acetyl group and R.sup.2 represents a phenyl, naphthyl or pyridyl group or such group substituted by the groups R.sup.3 and R.sup.4, the groups R.sup.3 and R.sup.4, which may be the same or different, each representing hydrogen, hydroxyl, fluorine, chlorine, bromine, a nitro group, a trifluoromethyl group, a C.sub.1 to C.sub.6 -alkyl group, a C.sub.1 to C.sub.6 -alkoxy group, a C.sub.1 to C.sub.6 -alkyl thio group, a C.sub.1 to C.sub.6 -alkyl sulphonyl group, a C.sub.2 to C.sub.6 -alkanoyl group, an amino group, an acylamino group or an acyloxy group in which the acyl is of the type defined in respect to R.sup.1, and their salts. The compounds are pharmacodynamically active.

1-[3-(3,4,5-Trimethoxyphenoxy)-2-hydroxy-propyl]-4-

There are produced 6-aryl-s-triazolo-(4,3-a)-pyrido-(2,3-f)-(1,4)-diazepines of the formula: ##STR1## wherein R.sub.1 is hydrogen, a halogen atom, an alkyl mercapto group having 1 to 6 carbon atoms, R.sub.2 is hydrogen, an alkyl group with 1 to 6 carbon atoms, R.sub.3 is hydrogen or a halogen or a halogen atom the structural part A-B is the group --CH.sub.2 .dbd.NH-- and Y-Z is the group &gt;C.dbd.N--, &gt;C.dbd.N(.fwdarw.O), and Y-Z is the group &gt;C.dbd.N--, their optical isomers and their pharmaceutically acceptable salts. The compounds have anticonvulsive properties.

6-Aryl-s-triazolo-(4,3-alpha)-pyrido-(2,3-f)-(1,4)-diazepines

There are produced 6-aryl-s-triazolo-(4,3-a)-pyrido-(2,3-f)-(1,4)-diazepines of the formula: ##STR1## wherein R.sub.1 is hydrogen, a halogen atom, an alkyl group with 1 to 6 carbon atoms, a hydroxy group, an alkoxy group with 1 to 6 carbon atoms, a mercapto group, an alkyl mercapto group having 1 to 6 carbon atoms, an alkylsulfoxido group with 1 to 6 carbon atoms, an alkyl sulfono group with 1 to 6 carbon atoms, an amino group, an aliphatic acylamino group with 2 to 6 carbon atoms, a monoalkylamino group with 1 to 6 carb0n atoms, a dialkylamino group with 1 to 6 carbon atoms in each alkyl group or a saturated heterocyclic amino group having 5 to 7 members in the ring including 1 to 2 nitrogen atoms and 0 to 1 oxygen atoms in the ring, R.sub.2 is hydrogen, an alkyl group with 1 to 6 carbon atoms, a hydroxy group, an acyloxy group with 2 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, a mercapto group, an alkylmercapto group with 1 to 6 carbon atoms, a halogen atom, an amino group, an aliphatic acylamino group with 2 to 6 carbon atoms, a monoalkylamino group with 1 to 6 carbon atoms, a dialkylamino group with 1 to 6 carbon atoms in each alkyl group or a saturated heterocyclic amino group having 5 to 7 members in the ring including 1 to 2 nitrogen atoms and 0 to 1 oxygen atoms in the ring, R.sub.3 is hydrogen, an alkyl group with 1 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms or a halogen atom, The structural part A--B is the group --N.dbd.N--, --CH.sub.2 --NH--, --CO--NR.sub.4, --C(SR.sub.5).dbd.N--, --C(OR.sub.5).dbd.N--, --C(NR.sub.5 R.sub.5).dbd.N--, or --CR.sub.6 .dbd.N--, wherein R.sub.4 is hydrogen, an alkenyl group with 2 to 6 carbon atoms, an alkinyl group with 2 to 6 carbon atoms, a hydroxy-alkyl group with 1 to 6 carbon atoms, a ketoalkyl group with 1 to 6 atoms in the alkyl group, a cyanoalkyl group with 1 to 6 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or an alkyl group of 1 to 6 carbon atoms substituted by an alkoxy group with 1 to 6 carbon atoms, a dialkylamino group with 1 to 6 carbon atoms in each alkyl group or a saturated heterocyclic amino group having 5 to 7 members in the ring including 1 to 2 nitrogen atoms and 0 to 1 oxygen atoms, R.sub.5 is hydrogen or an alkyl group with 1 to 6 carbon atoms, R.sub.6 is hydrogen, an alkyl group with 1 to 6 carbon atoms or a haloalkyl group with 1 to 6 carbon atoms, And Y--Z is the group &gt;CH.dbd.N--, &gt;C.dbd.N(.fwdarw.O), &gt;CH--NH-- or &gt;CH--N(OH)-- and wherein R.sub.6 is other than alkyl if R.sub.1 is chlorine, R.sub.2 is hydrogen, R.sub.3 is hydrogen or halogen and Y-Z is the group &gt;C.dbd.N--, their optical isomers and their pharmaceutically acceptable salts. The compounds have anticonvulsive properties.

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Vladimir Jakovlev