Merck Patent Gesellschaft MIT Beschrankter Haftung

Merck Patent Gesellschaft MIT Beschraenkter Haftung

Albrecht Wild

Joachim Gante

Hans-Adolf Kurmeier

Erich Schacht

Dieter Orth

Werner Mehrhof

Zdenek Simane

Johann Dahm

Joachim Borck

Jan Willem Hovy

Hans-Eckart Radunz

Klaus Otto Minck

Michael Klockow

Pyrazole derivatives of the formula ##STR1## wherein R.sup.1 is H or Cl; R.sup.2 is 1-methyl-4-piperidyloxy-carbonyl, 2-(4-phenylpiperazino)-ethoxycarbonyl, benzoxazol-2-yl, benzthiazol-2-yl, tetrazol-5-yl or 3-R.sup.3 -4-R.sup.4 -thiazolidin-2-yl; R.sup.3 is H, alkanoyl of 1-7 carbon atoms or benzoyl; and R.sup.4 is H or COOH,

Pyrazole derivatives, pharmaceutical formulations thereof

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

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

Phenylalkanols of the formula ##STR1## wherein Ar is phenyl or phenyl monosubstituted or disubstituted by F, Cl, Br and/or CH.sub.3 ; X is F, Cl, Br or CN; m is 0 or 1; and n 2 or 3; possess antiinflammatory activity and can be produced by treating a compound of formula ##STR2## wherein Q is a functionally modified hydroxy group and Ar, X, m and n have the values given above, with a solvolyzing agent.

Phenylalkanol nitriles

Araliphatic dihalogen compounds and process for their preparation

Azole derivatives of the formula ##STR1## wherein R.sub.1 is free or esterified carboxyl or other functionally modified carboxyl group, R.sub.2 and R.sub.3 each are aryl; A is C.sub.n H.sub.2n in which n is an integer from 1 to 10, inclusive; and Z is O or S; and the physiologically acceptable salts thereof, possess, with good compatibility, excellent antiphlogistic activity and, in particular, influence favorably the chronic progressive diseases of the joints, e.g., arthritis. They can be prepared from compounds of the formula ##STR2## wherein X.sub.1 is a group convertible into the group --S--A--R.sub.1, and R.sub.2 and R.sub.3 have the values given above.

Antiinflammatory azole derivatives

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 I-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 and compositions containing them

Sulfoxides and sulfones of the formula ##SPC1## Wherein R.sub.1 is COOH, COOR.sub.4, CH.sub.2 OH, or CH.sub.2 OR.sub.5 ; R.sub.2 is CH.sub.3 or C.sub.2 H.sub.5 ; R.sub.3 is H, F, Cl, or Br; R.sub.4 is alkyl of 1-8 carbon atoms; R.sub.5 is alkanoyl of 2-4 carbon atoms; one of the Y groups is SO or SO.sub.2 and the other Y group is CH.sub.2, O, S, SO, or SO.sub.2 ; and the physiologically acceptable salts thereof, which compounds possess anti-inflammatory activity, can be produced by converting in a compound of the formula ##SPC2## Wherein X is a group convertible into the group --CHR.sub.1 R.sub.2 wherein R.sub.1, R.sub.2, R.sub.3, and Y have the values given above, the group X into the group --CHR.sub.1 R.sub.3.

Sulfoxides and sulfones

Pyrazolidinones of the formula ##SPC1## Wherein R is a phenyl, phenoxy or a corresponding group monosubstituted or polysubstituted by one or more of F, Cl and Br possess anti-inflammatory activity.

Pyrazolidinones and a process for their preparation

Compounds of the formula ##SPC1## Wherein R.sub.1 is COOH, COO-alkyl, CH.sub.2 OH or CH.sub.2 -alkanoyl; R.sub.2 is CH.sub.3 or C.sub.2 H.sub.5 ; R.sub.3 is H, F, Cl or Br; and Y is CH.sub.2, O or S, at least one Y being S, and the physiologically acceptable salts thereof, possesses antiphlogistic activity.

Growing community of inventors

Darmstadt, Germany

Albrecht Wild