Deutsche Gold- Und Silber-scheideanstalt Vormals Roessler

Degussa Aktiengesellschaft

Degussa Akteinsellschaft

Klaus Thiemer

Axel Kleemann

Fritz Stroman

Jurgen Engel

Vladimir Jakovlev

Ingomar Nubert

Gerhard Scheffler

Klaus Posselt

Karl H Klingler

Heribert Offermanns

Peter Emig

Bernd Nickel

Otto Isaac

Walter Von Bebenburg

Axel Kleeman

Carl-Heinrich Weischer

Istvan Szelenyi

Gerhard Oepen

Horst Uthemann

Erik Westermann

Ansgar Von Schlichtegroll

Ute-Achterrath Tuckermann

This invention relates to new compounds corresponding to the general formula: ##STR1## R.sub.1 represents a C.sub.3 -C.sub.10 cycloalkyl group substituted by C.sub.1 -C.sub.6 alkyl radicals, a C.sub.3 -C.sub.19 -cycloalkyl-C.sub.1 -C.sub.4 alkyl group which may be substituted by C.sub.1 -C.sub.6 alkyl radicals, a C.sub.6 -C.sub.8 bicycloalkyl group, a C.sub.6 -C.sub.8 bicycloalkyl-C.sub.1 -C.sub.4 alkyl group, a C.sub.6 -C.sub.10 tricycloalkyl group, a C.sub.6 -C.sub.10 tricycloalkyl-C.sub.1 -C.sub.4 alkyl group, a C.sub.6 -C.sub.9 tetracycloalkyl group or a C.sub.6 -C.sub.9 -tetracycloalkyl-C.sub.1 -C.sub.4 alkyl group,

Ethylenediamine and guanidine-derivatives

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 of the formula: ##STR1## wherein X is the group &gt;C.dbd.O or &gt;CH(OH), Y is the group ##STR2## R.sub.2 is hydrogen or C.sub.1 to C.sub.6 alkyl, R.sub.3 is hydrogen or a hydroxy group and R.sub.1 is the adamantyl group or a saturated or single unsaturated C.sub.3 to C.sub.16 cycloalkyl group where the C.sub.3 to C.sub.16 cycloalkyl group can be substituted by a C.sub.1 -C.sub.4 alkyl group or a halogen atom and their salts. The compounds are useful in dilating the peripheral blood vessels and in lowering blood pressure.

Cycloaliphatic ketoamines

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 prepared compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or together represent a second bond between the carbon atom carrying R.sub.1 and R.sub.2, R.sub.1 also can be a hydroxy group, R.sub.3 is hydrogen, a C.sub.3 -C.sub.8 cycloalkyl group or a C.sub.1 -C.sub.20 alkyl group, which optionally can also contain one or two hydroxy groups and the groups R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and are hydrogen, C.sub.1 -C.sub.6 -alkyl groups or halogen atoms, their N-oxide, their quaternary salts and their acid addition salts. There are also described processes for their production. The compounds possess especially an antischemic and blood pressure increasing activity.

Dithienylpiperidines, pharmaceutical compositions thereof, and method of

There are prepared compounds of the formula ##STR1## where &gt;A--B-- has either the structure &gt;C(OH)--CH.sub.2 -- or the structure &gt;C.dbd.CH, Alk is a straight or branched chain C.sub.1 --C.sub.5 --alkylene group and Y is ##STR2## where R is hydrogen or a C.sub.1 --C.sub.4 --alkyl group and T is hydrogen or a C.sub.2 --C.sub.6 --alkanoyl group ##STR3## where R' is hydrogen, phenyl, phenyl substituted once or twice. The compounds are effective in improving peripheral and cerebral circulation. There are also produced intermediate compounds of formula (II) where NHY is replaced by chlorine, bromine or iodine.

Dithienylalkylamines and process for their production

There are prepared compounds of the formula ##STR1## where R.sub.1 is hydrogen or hydroxy, R.sub.2 is hydrogen or R.sub.1 and R.sub.2 together represent a second bond between the carbon atoms carrying R.sub.1 and R.sub.2, Alk is a C.sub.2 -C.sub.6 alkylene group, R.sub.3 is a C.sub.3 -C.sub.8 -cycloalkyl group, a C.sub.1 -C.sub.6 -alkyl group, a C.sub.1 -C.sub.6 -hydroxyalkyl group or a C.sub.2 -C.sub.6 -hydroxyalkoxy-C.sub.1 -C.sub.6 -alkyl group and the groups R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and are hydrogen, C.sub.1 -C.sub.6 -alkyl group or halogen atoms, their N-oxides, their quaternary salts and their acid addition salts. There are also described processes for their production. The compounds have a strong bronchospasmolytic activity, antianaphylactic activity and an antihistamine-antiserotonine activity.

N-Alkoxy-dithienylpiperidines, pharmaceutical compositions thereof and

There are prepared compounds of the formula ##STR1## where &gt;A--B-- has either the structure &gt;C(OH)--CH.sub.2 -- or the structure &gt;C.dbd.CH, Alk is a straight or branched chain C.sub.1 -C.sub.5 -alkylene group and Y is a C.sub.3 -C.sub.7 -cycloalkyl group, a benzyl group, a methylenedioxybenzyl group, a benzyl group having one, two or three C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy group substituents, a C.sub.1 -C.sub.6 -alkyl group, or a C.sub.1 -C.sub.6 -alkyl group substituted by an amino group, a di C.sub.1 -C.sub.4 -alkylamino group, a mono C.sub.1 -C.sub.4 -alkyl-amino group, a morpholino group, a piperazino group or a 4-(C.sub.1 -C.sub.4 -alkyl)-piperazino group, or Y is ##STR2## where R is hydrogen or a C.sub.1 -C.sub.4 -alkyl group and T is hydrogen or a C.sub.2 -C.sub.6 -alkanoyl group or where --NHY is ##STR3## where R' is hydrogen, phenyl, phenyl substituted once or twice by C.sub.1 -C.sub.4 -alkyl groups, a C.sub.1 -C.sub.4 -alkoxy group or by halogen atoms, a C.sub.1 -C.sub.6 -alkyl group, a C.sub.1 -C.sub.4 -hydroxyalkyl group or a phenalkyl group whose alkyl portion consists of 1-4 carbon atoms or such a phenalkyl group containing 1 to 3 C.sub.1 -C.sub.4 -alkoxy group substituents or when Alk has 2 to 5 carbon atoms the group --NHY is a di-C.sub.1 -C.sub.4 -alkylamino group or the group --NH--CH(R)--CH(OH)--C.sub.6 H.sub.5 and salts thereof. The compounds are effective in improving peripheral and cerebral circulation. There are also produced intermediate compounds of formula (II) where NHY is replaced by chlorine, bromine or iodine.

Dithienyl beta-haloethyl carbinols

There are prepared 7-azabenzimidazoles of the formula ##STR1## where R.sub.1 and R.sub.2 are the same or different and are hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.6 -alkanol or --NR.sub.1 R.sub.2 is a 5 to 7 membered saturated heterocyclic ring having either one nitrogen atom, one nitrogen atom and one oxygen atom or two nitrogen atoms, R.sub.3 is hydroxy, an amino group, a mono C.sub.1 -C.sub.6 -Alkylamino group, a di-C.sub.1 -C.sub.6 -alkylamino group, or a C.sub.2 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, mercapto, C.sub.1 -C.sub.6 -alkylmercapto, hydroxy or C.sub.1 -C.sub.6 -alkoxy, R.sub.5 is hydrogen or halogen and A is a C.sub.2 -C.sub.6 -alkylene group or a salt of such compound. Preferably R.sub.1 and R.sub.2 are two equal C.sub.1 -C.sub.6 -alkyl groups or --NR.sub.1 R.sub.2 is piperidino, pyrrolidino, morpholino, homopiperidino, piperazino or homopiperazino, R.sub.3 is hydroxy, mercapto, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylmercapto or C.sub.1 -C.sub.6 -alkylmino, mercapto, C.sub.1 -C.sub.6 -alkylmercapto, hydroxy or C.sub.1 -C.sub.6 -alkoxy and R.sub.5 is hydrogen and salts thereof. The compounds are useful in treating ulcers and gastritis.

7-Azabenzimidazoles with basic side chains and use thereof

There are prepared compounds corresponding to the general formula: ##STR1## in which R represents a 2,2-dimethylethenyl; isopropyl; nonyl; a C.sub.3 -C.sub.6 -cycloalkyl radical; a phenyl group substituted by at least one nitro group, or a C.sub.1 -C.sub.6 -alkyl group containing a morpholine group attached thereto, said morpholine ring being substituted zero to twice by C.sub.1 -C.sub.6 -alkyl groups; R.sub.3 is --CHO or --CH.sub.2 OH, their optically active forms and their salts. The compounds have cardioactivity e.g., bradycardic effect and have local anethetic, spasmolytic and antiarythmic activity.

Acyl derivatives of hellebrigenin

There are prepared compounds of the formula ##STR1## where &gt;A--B-- has either the structure &gt;C(OH)--CH.sub.2 -- or the structure &gt;C.dbd.CH, Alk is a straight or branched chain C.sub.1 -C.sub.5 - alkylene group and -NHY is ##STR2## where R' is hydrogen, phenyl, phenyl substituted once or twice by C.sub.1 -C.sub.4 -alkyl groups, a C.sub.1 -C.sub.4 -alkoxy group or by halogen atoms, a C.sub.1 -C.sub.6 -alkyl group, a C.sub.1 -C.sub.4 -hydroxyalkyl group or a phenalkyl group whose alkyl portion consists of 1-4 carbon atoms or such a phenalkyl group containing 1 to 3 C.sub.1 -C.sub.4 -alkoxy group substituents. The compounds are effective in improving peripheral and cerebral circulation. There are also produced intermediate compounds of formula (II) where NHY is replaced by chlorine, bromine or iodine.

There are prepared compounds of the formula ##STR1## in which T is the theophyllin-7-yl group and alk is a straight or branched alkylene chain with 2 to 4 carbon atoms and salts thereof. The compounds promote circulation and produce a marked and persistent increase in renal circulation.

Dihydroxyphenylethylaminoalkyl theophyllines

There are prepared compounds corresponding to the general formula

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Hanau, Germany

Klaus Thiemer