Janssen Pharmaceutica Nv

Raymond A Stokbroekx

Marcel J Van Der Aa

Marcel G Luyckx

Jan Heeres

Marc Willems

Gilbert A Grauwels

Frans E Janssens

Joseph H Mostmans

Robert W Tuman

Joannes J Willems

Marcel Jozef Maria Van Der Aa

Louis J Van Der Veken

Marcel Gerebernus Maria Luyckx

Leo J Backx

Theophilus T Van Offenwert

Marc Andr&eacute; Ceusters

Bernard R Boar

Robert Jozef Hendrickx

Cyriel A Van Der Eycken

Lieven Meerpoel

Joseph L Torremans

Frank Christopher Odds

Marc André Ceusters

Luc Alfons Van Der Eycken

G M Marcel

Marcel Jozef Van De Aa

This invention concerns compounds of formula the N-oxide forms, the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein X is CH or N; Ris hydrogen, Calkyl, Calkyloxy, Calkylthio, amino, mono- or di(Calkyl)amino, Ar, ArNH&#x2014;, Ccycloalkyl, hydroxymethyl or benzoyloxymethyl; Ris hydrogen, Calkyl, amino, aminocarbonyl, mono- or di(Calkyl)amino, Calkyloxycarbonyl, Calkylcarbonylamino, hydroxy or Calkyloxy; R, Rand Rare each independently selected from hydrogen, halo, Calkyl, Calkyloxy, trifluoromethyl, nitro, amino, cyano, azido, CalkyloxyCalkyl, Calkylthio, Calkyloxycarbonyl or Het; is Ar, ArCH&#x2014; or Het; Arand Aroptionally substituted phenyl; Hetand Hetare optionally substituted monocyclic heterocycles; having angiogenesis inhibiting activity; their preparation, compositions containing them and their use as a medicine.

Angiogenesis inhibiting 5-substituted-1,2,4-thiadiazolyl derivatives

Angiogenesis inhibiting 5-substituted-1,2,4,-thiadiazolyl derivatives

Angiogenesis inhibiting thiadiazolyl pyridazine derivatives

This invention concerns compounds of formula

This invention concerns compounds of formula the N-oxide forms, the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein X is CH or N; m is 2 or 3 and n is 1, 2 or 3; wherein 1 or 2 C-atoms of the CH.sub.2 groups of the ##STR1## moiety which may also contain one double bond, may be substituted with C.sub.1-6 alkyl, amino, aminocarbonyl, mono- or di(C.sub.1-6 alkyl)amino, C.sub.1-6 alkyloxycarbony, C.sub.1-6 alkylcarbonylamino, hydroxy or C.sub.1-6 alkyloxy; and/or 2 C-atoms of said CH.sub.2 groups may be bridged with C.sub.2-4 alkanediyl; R.sup.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, C.sub.1-6 alkylthio, amino, mono- or di(C.sub.1-6 alkyl)amino, Ar, ArNH--, C.sub.3-6 cycloalkyl, hydroxymethyl or benzyloxymethyl; R.sup.2 and R.sup.3 are hydrogen, or taken together may form a bivalent radical of formula --CH.dbd.CH--CH.dbd.CH--; in case X represents CH then L is a radical L.sup.1, L.sup.2 or L.sup.3 ; or in case X represents N then L is a radical L.sup.2 or L.sup.3 ; L.sup.1 is Ar-C.sub.1-6 alkyloxy, Ar-oxy, Ar-thio, Ar-carbonylamino, di-Ar-methyloxy-, N-Ar-piperazinyl, N-Ar-homopiperazinyl, 2-benzimidazolinonyl, Ar--NR.sup.4 --, Ar-Alk-NR.sup.4 --, Ar--NR.sup.4 -Alk-NR.sup.5 -- or Het-NR.sup.4 --; L.sup.2 is Ar, Ar-carbonyl, Ar--CH.dbd.CH--CH.sub.2 --, naphtalenyl or Het; L.sup.3 is C.sub.1-6 alkyl substituted with one or two radicals selected from Ar, Ar-oxy, or Ar-thio, further optionally substituted with cyano or hydroxy; 2,2-dimethyl-1,2,3,4-tetrahydro-naphtalenyl; 2,2-dimethyl-1H-2,3-dihydroindenyl;Ar-piperidinyl or Ar--NR.sup.4 -Alk-; R.sup.4 and R.sup.5 are each independently selected from hydrogen or C.sub.1-6 alkyl; Alk is C.sub.1-6 alkanediyl; their preparation, compositions containing them and their use as a medicine.

Angiogenesis inhibiting pyridazinamines

Urea and thiourea derivatives of azolones

Sulfonamide compounds of azolones anti-helicobacter agents

Ester and carbamate derivatives of azolones

Intermediate for making 4-�2-Benzothiazolyl)methylamino!-alpha-�93,4-difluorophenoxy0methyl!1-pipe ridineethanol having the formula ##STR1##

Intermediates for making 4-�(2-benzothiazolyl)methylamino!-.alpha.-�(3,

Substituted azolone derivatives

The invention is concerned with the compounds having the formula ##STR1## the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein X is O or S; Y is CH or N; R.sup.1, R.sup.2 and R.sup.3 each independently are hydrogen or C.sub.1-4 alkyl; R.sup.4 and R.sup.5 each independently are hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy; R.sup.6 is C.sub.1-4 alkyl; C.sub.1-4 alkyl substituted with arylcyclohexyl; aryl or arylcarbonyl; wherein aryl is phenyl optionally substituted with one or two substituents selected from halo and C.sub.1-4 alkyl;

The invention is concerned with the compounds having the formula ##STR1## the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein Y is CH or N; R.sup.1, R.sup.2 and R.sup.3 each independently are hydrogen or C.sub.1-4 alkyl; R.sup.4 and R.sup.5 each independently are hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, hydroxy, trifiuoromethyl, trifiuoromethyloxy or difluoromethyloxy; R.sup.6 is hydrogen; or R.sup.6 is phenyl optionally substituted with halo; pyridinyl; furanyl; thienyl; 3-chloro-benzo[b]thien-2-yl; trifiuoromethyl; C.sub.1-4 alkyloxycarbonyl; dihalophenylcyclopropanyl; C.sub.3-6 cycloalkyl; adamantyl; C.sub.2-6 alkenyl optionally substituted with halophenyl; or C.sub.1-4 alkyl optionally substituted with halo, phenyl, halophenyl, dihalophenyl, phenyloxy, piperidinyl, pyrrolidinyl, piperazinyl, C.sub.1-4 alkylpiperazinyl, C.sub.1-4 alkylcarbonylpiperazinyl, C.sub.1-4 alkyloxycarbonylpiperazinyl, phthalimino, amino, mono- or di(C.sub.1-20)alkylamino or C.sub.3-6 cycloalkylamino; Z is C.dbd.O or CHOH; and ##STR2## is a radical of formula ##STR3## Compositions comprising said compounds, processes for preparing the same and the use of these compounds as a medicine.

Acyl derivatives of azolones

The invention is concerned with the compounds having the formula ##STR1## the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein Y is CH or N; R.sub.1, R.sup.2 and R.sup.3 each independently are hydrogen or C.sub.1-4 alkyl; R.sup.4 and R.sup.5 each independently are hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy; R.sup.6 is pyridinyl optionally substituted with up to two C.sub.1-4 alkyl groups; di(C.sub.1-4 alkyl) hydroxypyridinyl; di(C.sub.1-4 alkyl)C.sub.1-4 alkyloxypyridinyl; pyridazinyl optionally substituted with C.sub.1-4 alkyloxy; pyrimidinyl optionally substituted with hydroxy or C.sub.1-4 alkyloxy; thiazolyl optionally substituted with C.sub.1-4 alkyl; thiadiazolyl optionally substituted with C.sub.1-4 alkyl; benzoxazolyl or benzothiazolyl; or R.sup.6 is pyrazinyl or pyridazinyl substituted with C.sub.1-4 alkyl; Z is C.dbd.O or CHOH; and ##STR2## is a radical of formula ##STR3## Compositions comprising said compounds, processes for preparing the same and the use of these compounds as a medicine.

Heterocyclic derivatives of azolones

The invention is concerned with the compounds having the formula ##STR1## the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein Y is CH or N; R.sup.1, R.sup.2 and R.sup.3 each independently are hydrogen or C.sub.1-4 alkyl; R.sup.4 and R.sup.5 each independently are hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy; R.sup.6 is C.sub.1-4 alkyl; or phenyl optionally substituted with halo, C.sub.1-4 alkylcarbonylamino, C.sub.1-4 alkyloxy, C.sub.1-4 alkyl or nitro; Z is C.dbd.O or CHOH; and ##STR2## is a radical of formula ##STR3## Compositions comprising said compounds, processes for preparing the same and the use of these compounds as a method of treating Helicobacter infection.

Sulfonamide derivatives of azolones

A compound of formula ##STR1## the racemic mixture, the (S)-form and the acid addition salts thereof, said compound having anti-stroke properties. Pharmaceutical compositions containing this compound as active ingredient and a method of preparing said compound and pharmaceutical compositions.

4-[(2-benzothiazolyl)methyla

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Beerse, Belgium

Raymond A Stokbroekx