Merck Patent Gesellschaft MIT Beschrankter Haftung

Merck Patent Gesellschaft MIT Beschraenkter Haftung

Celamerck Gmbh & Co. Kg

Erich Schacht

Werner Mehrhof

Zdenek Simane

Joachim Gante

Hans-Adolf Kurmeier

Albrecht Wild

Herbert Nowak

Dieter Orth

Detlev Kayser

Reinhard Lissner

Gunter Lauterbach

Rochus Jonas

Jurgen Curtze

Guido Melzer

Hans-Eckart Radunz

Gerbert Linden

Klaus Thomas

Ernst Schulze

Hans Dahm

Siegmund Lust

Thomas Doll

Benzothiazole derivatives of the formula I ##STR1## wherein R.sup.1 is H or CH.sub.3 ; R.sup.2 is phenyl, tolyl, xylyl or pyridyl; R.sup.3 is OH, alkoxy of 1-4 C atoms or -NHCH.sub.2 CH.sub.2 OH; and R.sup.4 is H, Cl, Br, OH or alkoxy of 1-4 C atoms,

Benzothiazole derivatives and pharmaceutical formulations containing them

Compounds of the formula ##STR1## wherein R.sup.1 is 4-biphenylyl, 4-phenoxyphenyl or 4-biphenylyl or 4-phenoxyphenyl substituted in the 4'-position by F, Cl, Br or I; R.sup.2 is H, C.sub.1-4 -alkyl, hydroxy-C.sub.1-4 -alkyl or pyridyl; R.sup.3 and R.sup.6 are each H or alkyl of 1-4 carbon atoms, or together are--(CH.sub.2).sub.4 --; and R.sup.4 and R.sup.5 are each H or together are a C--C bond; at least one of the radicals R.sup.2, R.sup.3 and R.sup.6 being other than hydrogen, possess valuable pharmacological properties, e.g., lower lipid levels and are anti-thrombotic.

Lipid lowering and anti-thrombotic 6-arylpyridazin-3-ones and a process

Morpholino containing compounds, compositions and use thereof

Alkyne compounds of the formula ##STR1## wherein R.sup.1 is H, alkyl of up to 4 carbon atoms or phenyl; R.sup.2 is H, aliphatic acyl of up to 6 carbon atoms or aroyl of up to 11 carbon atoms; R.sup.3 and R.sup.4 are H, F, Cl or Br and n is 0 or 1, and physiologically acceptable metals salts thereof, have anti-inflammatory activity. These compounds can be made from compounds of the formula ##STR2## wherein Q is a functionally-modified hydroxy and R.sup.1, R.sup.3, R.sup.4 and n are as above by treatment with a solvolyzing agent.

Alkyne compounds and method of use

Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen, chlorine or fluorine; and

2-[4-(4-Chlorophenoxymethyl)-phenoxy]-propionic acid compounds as

New quinolone derivatives of the Formula I ##STR1## wherein R.sup.1 and R.sup.2 are each H, F, Cl, Br, CF.sub.3 or CH.sub.3 O or a physiologically acceptable acid addition salt thereof possess pharmacological properties including thrombocyte aggregation inhibiting action.

Quinolone derivatives

Alkynols of the formula, ##STR1## wherein X is F, Cl or Br; n is 0 or 1; m is 0 or 1 and R (if m is 0) is hydroxyalkyl of 1-6 carbon atoms or (if m is 1) alkyl, straight-chain hydroxyalkyl or straight-chain tetrahydropyran-2-yloxyalkyl of 2-6 carbon atoms in the alkyl, have anti-inflammatory activity.

Alkynols and process for their preparation

Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are F, Cl or Br;

Araliphatic dihalogen compounds composition and method of use

Phenylbutanol derivatives of the formula Z-C(CH.sub.3) (OH)-CH.sub.2 -Y wherein Z is 4-biphenyl or 4-phenoxyphenyl wherein the phenoxy group is unsubstituted or substituted by F, Cl or Br and Y is COOR.sup.2 or CH.sub.2 OR.sup.3 wherein R.sup.2 is H or alkyl of 1 to 6 carbon atoms and R.sup.3 is H or alkanoyl of 1 to 6 carbon atoms, and their physiologically acceptable salts, possess anti-inflammatory activity and are produced by (a) treating with a solvolyzing agent a compound of the formula Z-C(CH.sub.3) (OH)-CH.sub.2 -W or Z-CX(CH.sub.3)-CH.sub.2 -Y wherein W is a functionally modified carboxy or methylol group different from Y and X is Cl, Br or I or a functionally modified hydroxyl group; or (b) reducing a compound otherwise corresponding to a desired final product but having instead of one of the hydrogen atoms a group which can be reduced or replaced by a hydrogen atom; or (c) oxidizing a compound otherwise corresponding to a desired final product but lacking the tertiary hydroxyl group; or (d) converting a compound otherwise corresponding to a desired final product wherein Z is a 4-phenoxyphenyl group but having instead a 4-OH-, Cl-, Br- or 1-substituted phenyl group into a desired final product; or (e) diazotizing a compound otherwise corresponding to a desired final product wherein Z is a halogen-substituted 4-phenoxyphenyl group but having an --NH.sub.2 -substituted phenoxy group and reacting the resulting diazonium salt with a halogenating agent.

Phenylbutanol derivatives, processes for their preparation and

Alkyne compounds of the formula ##STR1## wherein R.sup.1 is H, alkyl of up to 4 carbon atoms or phenyl; R.sup.2 is H, aliphatic acyl of up to 6 carbon atoms or aroyl of up to 11 carbon atoms; R.sup.3 and R.sup.4 are H, F, Cl or Br and n is 0 or 1, and physiologicaly acceptable metals salts thereof, have antiinflammatory activity. These compounds can be made from compounds of the formula ##STR2## wherein Q is a functionally-modified hydroxy and R.sup.1, R.sup.3, R.sup.4 and n are as above by treatment with a solvolyzing agent.

Anti-inflammatory (halo-4-biphenylyl)-alkanolamines

Hydratropic acid derivatives of the formula ##STR1## wherein R.sub.1 is H, alkyl of 1-4 carbon atoms, 2-acetamidoethyl, 1-methyl-4-piperidyl, or 2,3-dihydroxypropyl, and R.sub.2 is Hal, phenyl, 4-Hal-phenyl, 4-Hal-phenoxy, 4-Hal-phenoxymethyl, 1,2,3,4-tetrahydro-1-naphthyl, 1-pyrryl, piperidino, isoindolino, 1,2,3,4-tetrahydroquinolino, 1,2,3,4-tetrahydro-4-quinolyl or 1-methyl-1,2,3,4-tetrahydro-4-quinolyl, Hal being F, Cl, or Br, and the physiologically acceptable salts thereof, which possess cholesterol and triglyceride serum-level-lowering activity, can be prepared by reacting a phenol of the formula ##STR2## with a compound of the formula X--C(CH.sub.3)(C.sub. 6 H.sub.5)--COOR.sub.1 wherein X represents Cl, Br, I, OH, or esterified OH.

Hydratropic acid derivatives and process for the production thereof

Biphenylyl ethers of the formula ##STR1## and their physiologically acceptable acid addition salts exhibit pharmaceutically useful serum cholesterol and triglyceride lowering, fibrinolytic, thrombocyte aggregation inhibition, .beta.-receptor blocking and neuroleptic effects.

Biphenylyl ethers

Indole derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are identical or different and each is H or alkyl of 1 - 6 carbon atoms, R.sup.4 is H or methyl and R.sup.5 is methyl, phenyl or chlorophenyl, and their physiologically acceptable salts, are blood cholesterol-lowering agents.

Indole derivatives and process for their preparation

Biphenylyl ethers of the formula R--O--CH.sub.2 --CR.sub.1 (OH)--CH.sub.2 Z wherein R.sub.1 is H or CH.sub.3 ; Z is dialkylamino of 2-8 carbon atoms, morpholino, pyrrolidino, piperidino, homopiperidino, hydroxypyrrolidino, hydroxypiperidino or hydroxyhomopiperidino; R is either biphenylyl substituted by at least one of F, Cl, Br, I, CF.sub.3, NO.sub.2 and piperidino or, when R.sub.1 is CH.sub.3 or when Z is homopiperidino, hydroxypyrrolidino, hydroxypiperidino or hydroxyhomopiperidino, unsubstituted biphenyl, and the physiologically acceptable acid addition salts thereof, possess cholesterol blood-level-lowering activity and can be produced by reacting a compound of the formula R--O--CH.sub.2 --Y wherein Y is ##STR1## or --CR.sub.1 (OH)--CH.sub.2 X, X being Cl, Br, I or a free or functionally modified OH-group, with an amine of the formula H-Z.

Growing community of inventors

Darmstadt, Germany

Erich Schacht