Patent number: 7208503
Abstract: 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; R1 is hydrogen, C1-6alkyl, C1-6alkyloxy, C1-6alkylthio, amino, mono- or di(C1-6alkyl)amino, Ar1, Ar1NH—, C3-6cycloalkyl, hydroxymethyl or benzoyloxymethyl; R2 is hydrogen, C1-6alkyl, amino, aminocarbonyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl, C1-6alkylcarbonylamino, hydroxy or C1-6alkyloxy; R3, R4 and R5 are each independently selected from hydrogen, halo, C1-6alkyl, C1-6alkyloxy, trifluoromethyl, nitro, amino, cyano, azido, C1-6alkyloxyC1-6alkyl, C1-6alkylthio, C1-6alkyloxycarbonyl or Het1; is Ar2, Ar2CH2— or Het2; Ar1 and Ar2 optionally substituted phenyl; Het1 and Het2 are optionally substituted monocyclic heterocycles; having angiogenesis inhibiting activity; their preparation, compositions containing them and their use as a medicine.
Type:
Grant
Filed:
March 13, 2003
Date of Patent:
April 24, 2007
Assignee:
Janssen Pharmaceutica N.V.
Inventors:
Raymond Antoine Stokbroekx, Marc André Ceusters, Marcel Jozef Maria Van der Aa, Marcel Gerebernus Maria Luyckx, Marc Willems, Robert W. Tuman
Patent number: 6833369
Abstract: 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; R1 is hydrogen, C1-6alkyl, C1-6alkyloxy, C1-6alkylthio, amino, mono- or di(C1-6alkyl)amino, Ar1, Ar1NH—, C3-6cycloalkyl, hydroxymethyl or benzyloxymethyl; R2 is hydrogen, C1-6alkyl, amino, aminocarbonyl, mono- or di(C1-6alkyl)amino, C1-6alkyloxycarbonyl, C1-6alkylcarbonylamino, hydroxy or C1-6alkyloxy; R3, R4 and R5 are each independently selected from hydrogen, halo, C1-6alkyl, C1-6alkyloxy, trifluoromethyl, nitro, amino, cyano, azido, C1-6alkyloxyC1-6alkyl, C1-6alkylthio, C1-6alkyloxycarbonyl or Het1;
is Ar2, Ar2CH2— or Het2; Ar1 and Ar2 optionally substituted phenyl; Het1 and Het2 are optionally substituted monocyclic heterocycles; having angiogenesis inhibiting activity; their preparation, compositions containing them and their use as a medicine.
Type:
Grant
Filed:
October 19, 2001
Date of Patent:
December 21, 2004
Assignee:
Janssen Pharmaceutica, NV
Inventors:
Raymond Antoine Stokbroekx, Marc André Ceusters, Marcel Jozef Maria Van der Aa, Marcel Gerebernus Maria Luyckx, Marc Willems, Robert W. Tuman
Patent number: 6602873
Abstract: This invention concerns compounds of formula
the N-oxide forms, the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein R1 is hydrogen, C1-6alkyl, C1-6alkyloxy, C1-6alkylthio, amino, mono- or di(C1-6alkyl)amino, Ar1, Ar1—NH—, C3-6cycloalkyl, hydroxymethyl or benzyloxymethyl; R2 and R3 are hydrogen, or taken together may form a bivalent radical of formula —CH═CH—CH═CH—; R4, R5 and R6 are each independently selected from hydrogen, halo, C1-6alkyl, C1-6alkyloxy, trifluoromethyl, nitro, amino, cyano, azido, C1-6alkyloxyC1-6alkyl, C1-6alkylthio, C1-6alkyloxycarbonyl or Het1; or when R4 and R5 are adjacent to each other they may be taken together to form a radical of formula —CH═CH—CH═CH—; A is a bivalent radical of formula NR7, NR7-Alk1-X-, NR7-Alk1-X-Alk2-, O-Alk1-X-, O-Alk1-X-Alk2- or S-Alk1-X-; wherein X is a direct bond, —O—, —S—, C═O, —NR8&md
Type:
Grant
Filed:
May 24, 2001
Date of Patent:
August 5, 2003
Assignee:
Janssen Pharamaceutica, N.V.
Inventors:
Raymond Antoine Stokbroekx, Marc André Ceusters, Marcel Jozef Maria Van der Aa, Marcel Gerebernus Maria Luyckx, Marc Willems, Robert W. Tuman
Patent number: 6265407
Abstract: This invention concerns compounds of formula
the N-oxide forms, the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein R1 is hydrogen, C1-6alkyl, C1-6alkyloxy, C1-6alkylthio, amino, mono- or di(C1-6alkyl)amino, Ar1, Ar1—NH—, C3-6cycloalkyl, hydroxymethyl or benzyloxymethyl; R2 and R3 are hydrogen, or taken together may form a bivalent radical of formula —CH═CH—CH═CH—; R4, R5 and R6 are each independently selected from hydrogen, halo, C1-6alkyl, C1-6alkyloxy, trifluoromethyl, nitro, amino, cyano, azido, C1-6alkyloxyC1-6alkyl, C1-6alkylthio, C1-6alkyloxycarbonyl or Het1; or when R4 and R5 are adjacent to each other they may be taken together to form a radical of formula —CH═CH—CH═CH—; A is a bivalent radical of formula NR7, NR7—Alk1—X—, NR7—Alk1—X—Alk2—, O—Alk1—X—, O—Alk1—X—Alk2— or S—Alk1
Type:
Grant
Filed:
August 14, 2000
Date of Patent:
July 24, 2001
Assignee:
Janssen Pharmaceutica N.V.
Inventors:
Raymond Antoine Stokbroekx, Marc André Ceusters, Marcel Jozef Maria Van der Aa, Marcel Gerebernus Maria Luyckx, Marc Willems, Robert W. Tuman
