Patent number: 7414048
Abstract: The present invention is concerned with the compounds of formula wherein m, n and p are each independently 0 or 1 and q is 0, 1, 2, 3, 4 or 5; -A1=A2-A3=A4- is a pyridinylidene, pyridazinylidene, pyrimidinylidene, pyrazinylidene or phenylidene; B represents an amide, ketone or oxadiazole; D represents Ar or Het; Q represents a covalent direct bond or a ketone, —N—, —O—, —CR5R6—, amide, ethenyl, imine, sulfonyl, sulfinyl, 3-oxobutenyl, pyrazole, isoxazole or thiazole; L represents Ar or Het; R1 represents hydrogen, halo, hydroxy, C(2-6)alkenyl, C(2-6)alkynyl, C(3-6)cycloalkyl, C(3-6)cycloalkenyl, cyano, guanidine, nitro, NR17R18, an optionally substituted C(1-6)alkyl or C(1-6)alkyloxy; R2 and R3 each independently represent hydrogen, halo, C(1-6)alkyloxy or an optionally substituted C(1-6)alkyl; R5 and R6 each independently represent hydrogen, hydroxy, halo, an optionally substituted C(1-6)alkyl, C(2-6)alkenyl, C(2-6)alkynyl, C(3-6)cycloalkyl, C(3-6)cycloalkenyl, C(1-6)alkyloxy, cyano, (C?O)R25, (C—O)OR16,
Type:
Grant
Filed:
March 31, 2003
Date of Patent:
August 19, 2008
Assignee:
Janssen Pharmaceutica, N.V.
Inventors:
Eddy Jean Edgard Freyne, José Ignacio Andrés-Gil, Frederik Dirk Deroose, Davy Petrus Franciscus Maria Petit, Maria Encarnacion Matesanz-Ballesteros, Rosa Maria Alvarez Escobar
Patent number: 6894046
Abstract: The present invention is concerned with the compounds of formula the N-oxides, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein p is 0 to 4; X is O, S, NR5 or a direct bond; Y is O, S, NR5 or S(O)2; R1 independently is C1-6alkyl, halo, polyhaloC1-6alkyl, hydroxy, mercapto, C1-6alkyloxy, C1-6alkylthio, C1-6alkylcarbonyloxy, aryl, cyano, nitro, Het3, R6, NR7R8 or substituted C1-4alkyl; R2 is Het1, C3-7cycloalkyl or optionally substituted C1-6alkyl and if X is O, S or NR5, then R2 may also represent aminocarbonyl, aminothiocarbonyl, C1-4alkylcarbonyl, C1-4alkylthiocarbonyl, arylcarbonyl, arylthiocarbonyl, Het1carbonyl or Het1thiocarbonyl; R3 and R4 independently are hydrogen, C1-6alkyl or C3-7cycloalkyl; R3 and R4 form a C2-6alkanediyl; R5 is hydrogen or C1-4alkyl; R6 is a sulfonyl or sulfinyl derivative; R7 and R8 are independently hydrogen, optionally substituted C1-4alkyl, aryl, a carbonyl containing moiety, C3-7cycloalkyl, —Y—C1-4alkanediyl-C(?O)—O—R
Type:
Grant
Filed:
March 19, 2001
Date of Patent:
May 17, 2005
Assignee:
Janssen Pharmaceutica N.V.
Inventors:
Eddy Jean Edgard Freyne, Jean Fernand Armand Lacrampe, Frederik Dirk Deroose, Marc Gaston Venet
Patent number: 6803364
Abstract: The present invention is concerned with the compounds of formula (I), a N-oxide, a pharmaceutically acceptable addition salt, a quaternary amine or a stereochemically isomeric form thereof, wherein p is 0 to 4; q is 0 to 5; X is O, S, NR3 or a direct bond; or —X—R2 is CN; R1 is H, OH, halo, NH2, mono- or di(C1-4alkyl)NH2, C1-6alkyl, C1-6alkylO, C3-7cycloalkyl, aryl, arylC1-6alkyl, NH2C1-4akyl, mono- or di(C1-4alkyl)NH2C1-4akyl or mono- or di(C1-4alkyl)NH2C1-4alkylNH2; R2 is aryl, Het1, optionally substituted C3-7cycloalkyl, optionally substituted C1-6alkyl; R3 is H or C1-4alkyl; R4 and R5 are —C(═O)—Z—R14, C1-6alkyl, halo, polyhaloC1-6alkyl, OH, mercapto, C1-6alkylO, C1-6alkylthio, C1-6alkylC(═O)O, aryl, cyano, nitro, Het3, R6, NR7R8 or C1-4alkyl substituted with —C(═O)—Z—R14, Het3, R6 or NR7R8; Z is O, S, NH, —CH2O or —CH2—S—; R14 is H, C1-20acyl, optionally substituted C1-20alkyl, optionally substituted C3-20alkenyl, C3-2
Type:
Grant
Filed:
August 29, 2001
Date of Patent:
October 12, 2004
Assignee:
Janssen Pharmaceutica N.V.
Inventors:
Eddy Jean Edgard Freyne, Frederik Dirk Deroose, Jean Fernand Armand Lacrampe, Werner Constant Johan Embrechts, Jerome Michel Claude Fortin
Patent number: 6583141
Abstract: The present invention is concerned with the compounds of formula
wherein m, n and p are each independently 0 or 1 and q is 0, 1, 2, 3, 4 or 5; —A1═A2—A3═A4— is a pyridinylidene, pyridazinylidene, pyrimidinylidene, pyrazinylidene or phenylidene; B represents an amide, ketone or oxadiazole; D represents Ar or Het; Q represents a covalent direct bond or a ketone, —N—, —O—, —CR5R6—, amide ethenyl, imine, sulfonyl, sulfinyl, 3-oxobutenyl, pyrazole, isoxazole or thiazole; L represents Ar or Het; R1 represents hydrogen, halo, hydroxy, C(2-6)alkenyl, C(2-6)alkynyl, C(3-6)cycloalkyl, C(3-6)cycloalkenyl, cyano, guanidine, nitro, NR17R18, an optionally substituted C(1-6)alkyl or C(1-6)alkyloxy; R2 and R3 each independently represent hydrogen, halo, C(1-6)alkyloxy or an optionally substituted C(1-6)alkyl; R5 and R6 each independently represent hydrogen, hydroxy, halo, an optionally substituted C(1-6)alkyl, C(2-6)alkenyl, C(2-6)alkynyl, C(3-
Type:
Grant
Filed:
April 6, 2001
Date of Patent:
June 24, 2003
Assignee:
Janssen Pharmaceutica, N.V.
Inventors:
Eddy Jean Edgard Freyne, José Ignacio Andrés-Gil, Frederik Dirk Deroose, Davy Petrus Franciscus Maria Petit, Maria Encarnacion Matesanz-Ballesteros, Rosa Maria Alvarez Escobar
Patent number: 6498158
Abstract: The present invention is concerned with the compounds of formula
the N-oxides, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein p is 0 to 3; q is 0 to 4; —A—B— represents —(CH2)r—, —(CH2)t—O—, —(CH2)t—S(═O)u— or —(CH2)t—NR3—; r is 2 to 4; t is 1 to 3; u is 0 to 2; X1 is O, S, NR3 or a direct bond; R1 and R4 are C1-6alkyl, halo, polyhaloC1-6alkyl, hydroxy, mercapto, C1-6alkyloxy, C1-6alkylthio, C1-6alkylcarbonyloxy, aryl, cyano, nitro, Het3, R6, NR7R8 or substituted C1-4alkyl; R2 is aryl, Het1, C3-7cycloalkyl, cyano, optionally substituted C1-6alkyl, —C(═Q)—X2—R15; R3 is hydrogen or C1-4alkyl; R15 is hydrogen, optionally substituted C1-6alkyl, C3-7cycloalkyl, aryl; where X2 is a direct bond, R15 may also be halo or Het1; where X2 is NR5, R15 may also be hydroxy; where X2 is C(═O)—NH—NH or NH—NH—C(&bo
Type:
Grant
Filed:
May 22, 2001
Date of Patent:
December 24, 2002
Assignee:
Janssen Pharmaceutica N.V.
Inventors:
Jean Fernand Armand Lacrampe, Yannick Ligny, Eddy Jean Edgard Freyne, Frederik Dirk Deroose
Patent number: 6469001
Abstract: The present invention is concerned with the compounds of formula
the N-oxides, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein p is 0 to 3; q is 0 to 5; —A—B— is —(CH2)r—, —(CH2)t—O—, —(CH2)t—S(═O)u— or —(CH2)t—NR3—; r is 2 to 4; t is 1 to 3; u is 0 to 2; X1 is O, S, NR3 or a direct bond; R1 and R4 are C1-6alkyl, halo, polyhaloC1-6alkyl, hydroxy, mercapto, C1-6alkyloxy, C1-6alkylthio, C1-6alkylcarbonyloxy, aryl, cyano, nitro, Het3, R6, NR7R8 or C1-4alkyl substituted with Het3, R6 or NR7R8; R2 represents aryl, Het1, C3-7cycloalkyl, cyano, C1-6alkyl, —C(═Q)—X2—R15 or C1-6alkyl substituted with one or two substituents selected from hydroxy, cyano, amino, mono- or di(C1-4alkyl)amino, C1-6alkyloxy, C1-6alkylsulfonyloxy, C1-6alkyloxycarbonyl, C3-7cycloalkyl, aryl, aryloxy, arylthio, Het1, Het1 oxy, Het1 thio and —C(═Q)&md
Type:
Grant
Filed:
May 22, 2001
Date of Patent:
October 22, 2002
Inventors:
Eddy Jean Edgard Freyne, Frederik Dirk Deroose, Davy Petrus Franciscus Maria Petit, Jean Fernand Armand Lacrampe