Merck Patent Gesellschaft MIT Beschrankter Haftung

Helmut Prucher

Christoph Seyfried

Rudolf Gottschlich

Gerd Bartoszyk

Jurgen Uhl

Hans-Heinrich Hausberg

Klaus Otto Minck

Anton Haase

Klaus-Otto Minck

Rochus Jonas

Joachim Gante

Hartmut Greiner

Henning Bottcher

Joachim Leibrock

Helmut Wahlig

Michael Klockow

Karl-August Ackermann

Klaus Irmscher

Josef Kramer

Jaime Piulats

Rolf-Dieter Hesch

Volkmar Rudolph

Hanns Wurziger

Hans-Adolf Kurmeier

Peter Raddatz

Guido Melzer

Sabine Bernotat-Danielowski

Frank Mauler

Andrew Barber

Harry Schwartz

Andrew Barbar

Manfred Stohrer

Horst Juraczyk

Piperidinylmethyloxazolidinone derivative

The invention relates to novel piperidinylmethyloxazolidin-2-one derivatives of the formula I ##STR1## in which R.sup.1 and R.sup.2 in each case independently of one another are unsubstituted or mono- to disubstituted phenyl radicals whose substituents can be A, OA, aryloxy having 6-10 C atoms, aralkyloxy having 7-11 C atoms, --O--(CH.sub.2).sub.n --O-- (bonded in directly adjacent positions or in the meta- or para-position to one another on the phenyl ring), --O--(CH.sub.2).sub.n --OH, Hal, CF.sub.3, OH, NO.sub.2, NH.sub.2, NHA, NA.sub.2, NHR.sup.3, NAR.sup.3, SO.sub.2 NH.sub.2, SO.sub.2 NHA, SO.sub.2 NA.sub.2, SO.sub.2 NHR.sup.3 (excluding R.sup.3 =SO.sub.2 A) , SO.sub.2 N (R.sup.3).sub.2 (excluding R.sup.3 =SO.sub.2 A) or R.sup.3,

Piperidinylmethyloxazolidinones

A benzylpiperidine compound of formula I ##STR1## in which R.sup.1 is H, Hal or nitro,

Benzylpiperidine derivatives

Novel 4-aryloxy- or 4-arylthiopiperidine derivatives of the formula I ##STR1## in which R.sup.1 and R.sup.2 are each, independently of one another, phenyl radicals which are unsubstituted or mono or disubstituted by A, OH, OA, aryloxy with 6-10 C atoms, aralkyloxy with 7-11 C atoms, --0--(CH.sub.2).sub.n --0--, Hal, CF.sub.3, NO.sub.2, NH.sub.2, NHA, NA.sub.2, NHAc, NAAc, NHSO.sub.2 A and/or NASO.sub.2 A,

4-aryloxy- and 4-arylthiopiperidine derivatives

Novel arylacetamides of the formula I ##STR1## in which Q is R.sup.4 --CH(CH.sub.2 Z)--NA--, ##STR2## R.sup.1 is Ar, cycloalkyl with 3-7 C atoms or C.sub.4 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.7 -alkyl,

Acrylacetamides

Compounds of the formula ##STR1## in which R.sup.1, X and Y have the meanings defined herein, and their salts, inhibit the binding of fibrinogen to the fibrinogen receptor and can be used for treating thrombosis, stroke, cardiac infarction, inflammations, arteriosclerosis, osteoporosis and tumors.

Adhesion receptor antagonists

Novel 1-(2-arylethyl)-pyrrolidines of the formula ##STR1## in which, Ar is a phenyl group which is unsubstituted or monosubstituted by OH, --O--CO--NH.sub.2, --O--CO--NHA, --O--CO--NA.sub.2, NH.sub.2, --NH--CHO, --NH--CO--A, --NH--CO--NH.sub.2, --NH--CO--NHA or NH--SO.sub.2 --A,

1-(2-arylethyl)-pyrrolidines

Novel oxazolidinones of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, Z and n have the meanings defined herein, and their salts have effects on the central nervous system, in particular calming effects.

Oxazolidinones

New benzimidazolylpyridazinones of the formula I ##STR1## in which R.sup.1 is a styryl or mononculear of binuclear heteroaryl radical which contains 1-4 heteroatoms, each of which is unsubstituted or singly or multiply substituted by alkyl, alkoxy, alkylthio, halogen, OH, SH, amino, alkylamino, dialkylamino, acylamino having 1-8 C atoms, nitro, COOH, COOalkyl and/or CN,

Benzimidazolylpyridazinones

Novel oxazolidinones of the formula I ##STR1## Z is O or S, R.sup.1 and R.sup.2 are each phenyl or benzyl radicals which are unsubstituted or mono- or disubstituted by alkyl, alkoxy, alkylthio, alkylsulfinyl and/or alkylsulfonyl having each 1-4 C atoms, alkanoyloxy and/or alkanoylamino having each 1-6 C atoms, F, Cl, Br, OH and/or CF.sub.3 or are heteroaryl radicals containing 1-4 heteroatoms and R.sup.3 and R.sup.4 are each H, alkyl or alkoxy having each 1-4 C atoms or are F, Cl, Br, OH or CF.sub.3, and also their salts have effects on the central nervous system, in particular neuroleptic effects.

A pyridizinone derivative of the formula I ##STR1## wherein R is F, Cl, Br, I or R.sup.1 R.sup.2 N,

Pyridazinone derivatives

New benzimidazolylpyridazinones of the formula I ##STR1## in which R.sup.1 is a styryl or mononuclear of binuclear heteroaryl radial which contains 1-4 heteroatoms, each of which is unsubstituted or singly or multiply substituted by alkyl, alkoxy, alkylthio, halogen, OH, SH, amino, alkylamino, dialkylamino, acylamino having 1-8 C atoms, nitro, COOH, COOalkyl and/or CN,

Halogenohydroxyflavones ##STR1## in which R is alkyl having 1-3 C atoms,

Halogenohydroxyflavones

Basic ethers of the formula ##STR1## wherein Z is CH.sub.3 --NR.sup.2 --CH.sub.2 CH.sub.2 --CHR.sup.1 --, (1-R.sup.2 -3-piperidyl)-CHR.sup.3 --, (1-R.sup.2 -2-piperidyl)--CH.sub.2 --CHR.sup.3 -- or 1-R.sup.2 -3-R.sup.4 -hexahydroazepinyl; R.sup.1 is cyclopropyl or Ar; R.sup.2 is H, alkyl of 1-4 C atoms, alkenyl of 2-4 C atoms, cycloalkylalkyl of 4-8 C atoms or benzyl; R.sup.3 is H or Ar; R.sup.4 is H or alkyl of 1-4 C atoms, Y is --O--CHQ.sup.1 --CHQ.sup.2 --CH.sub.2 --, --O--CHQ.sup.1 --CHQ.sup.2 --CO--, --O--CQ.sup.1 .dbd.CQ.sup.2 --CO-- or --CH.sub.2 --CHQ.sup.1 --CHQ.sup.2 --CO--; Q.sup.1 and Q.sup.2 are independently each H, alkyl of 1-4 C atoms, cycloalkyl or alkylcycloalkyl each of 3-6 total C atoms or Ar; and Ar is phenyl or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ; with the proviso that when Z is (CH.sub.3).sub.2 N--CH.sub.2 CH.sub.2 --CHR.sup.1 in 7-position and Y is --O--C(C.sub.6 H.sub.5).dbd.CH--CO-- or --O--C(C.sub.6 H.sub.5).dbd.C(CH.sub.3)--CO--, R.sup.1 is cyclopropyl, or phenyl substituted by F, Cl, alkoxy or alkylthio, each of 1-4 C atoms, methylenedioxy or CF.sub.3 ;

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Heppenheim, Germany

Helmut Prucher