Publication number: 20100272683
Abstract: Heterocyclylaminoalkyl Substituted Benzimidazoles Inhibitors of RSV replication of formula (I): The salts and stereochemically isomeric forms thereof, wherein Q is hydrogen, C1-6alkyl optionally substituted with a heterocycle or Q is C1-6alkyl substituted with both —OR4 and a heterocycle; wherein said heterocycle is oxazolidine, thiazolidine, 1-oxo-thiazolidine, 1,1-dioxothiazolidine, morpholinyl, thiomorpholinyl, 1-oxo-thiomorpholinyl, 1,1-dioxothiomorpholinyl, hexahydrooxazepine, hexahydrothiazepine, 1-oxo-hexahydrothiazepine, 1,1-dioxo-hexahydrothiazepine, pyrrolidine, piperidine, homopiperidine, piperazine; which heterocyle may be substituted with 1-2 substituents; each Alk is C1-6alkanediyl; R1 is Ar or optionally substituted piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, furanyl, tetrahydrofuranyl, thienyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, isothiazolyl, pyrazolyl, isoxazolyl, oxadiazolyl, quinolinyl, quinoxalinyl, benzofuranyl, benzothieny
Type:
Application
Filed:
June 20, 2006
Publication date:
October 28, 2010
Inventor:
Jean-Francois Bonfanti
Publication number: 20100092426
Abstract: Inhibitors of RSV replication of formula (I) the addition salts and stereochemically isomeric forms thereof, wherein Q is hydrogen, C1-6alkyl optionally substituted with a heterocycle or Q is C1-6alkyl substituted with both —OR4 and a heterocycle; wherein said heterocycle is oxazolidine, thiazolidine, 1-oxo-thiazolidine, 1,1-dioxothiazolidine, morpholinyl, thiomorpholinyl, 1-oxo-thiomorpholinyl, 1,1-dioxothiomorpholinyl, hexahydrooxazepine, hexahydro-thiazepine, 1-oxo-hexahydrothiazepine, 1,1-dioxo-hexahydrothiazepine, pyrrolidine, piperidine, homopiperidine, piperazine; which heterocyle may be substituted with 1-2 substituents; each Alk is C1-6alkanediyl; R1 is Ar2 or optionally substituted piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, furanyl, tetrahydro-furanyl, thienyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, isothiazolyl, pyrazolyl, isoxazolyl, oxadiazolyl, quinolinyl, quinoxalinyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazolyl, benzth
Type:
Application
Filed:
June 20, 2006
Publication date:
April 15, 2010
Inventors:
Jean-Francois Bonfanti, Philippe Muller, Jérôme Michel Claude Fortin, Frédéric Marc Maurice Doublet
Publication number: 20090062278
Abstract: The present invention concerns 5- or 6-substituted-benzimidazole derivatives having inhibitory activity on the replication of the respiratory syncytial virus and having the formula a prodrug, N-oxide, addition salt, quaternary amine, metal complex or stereochemically isomeric form thereof wherein Q is Ar2, R6, pyrrolidinyl substituted with R6, piperidinyl substituted with R6 or homopiperidinyl substituted with R6, G is a direct bond or optionally substituted C1-10alkanediyl; R1 is Ar1 or a monocyclic or bicyclic heterocycle; one of R2a and R2b is cyanoC1-6alkyl, cyanoC2-6alkenyl, Ar3C1-6alkyl, Het1C1-6alkyl, N(R8aR8b)C1-6alkyl, Ar3C2-6alkenyl, Het1C2-6alkenyl, Ar3aminoC1-6alkyl, Het1aminoC1-6alkyl, Ar3thioC1-6alkyl, Het1thioC1-6alkyl, Ar3sulfonylC1-6alkyl, Het1sulfonylC1-6alkyl, Ar3aminocarbonyl, Het1aminocarbonyl, Ar3(CH2)naminocarbonyl, Het1(CH2)naminocarbonyl, Ar3carbonylamino, Het1carbonylamino, Ar3(CH2)ncarbonylamino, Het1(CH2)ncarbonylamino, and the other one of R2a and R2b is hydrogen; in case R2a
Type:
Application
Filed:
October 17, 2008
Publication date:
March 5, 2009
Inventors:
Jean-Francois Bonfanti, Koenraad Jozef Lodewijk Andries, Jerome Michel Claude Fortin, Philippe Muller, Frederic Marc Maurice Doublet, Christophe Meyer, Rudy Edmond Willebrords, Tom Valerius Josepha Gevers, Philip Maria Martha Bern Timmerman
Publication number: 20090036466
Abstract: The present invention concerns amino-benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula their prodrugs, N-oxides, addition salts, quaternary amines, metal complexes and stereochemically isomeric forms wherein Q is Ar1 or C1-6alkyl substituted with one or more substituents selected from trifluoromethyl, C3-7cycloalkyl, Ar2, hydroxy, C1-4alkoxy, C1-4alkylthio, Ar2-oxy-, Ar2-thio-, Ar2(CH2)noxy, Ar2(CH2)nthio, hydroxycarbonyl, aminocarbonyl, C1-4alkylcarbonyl, Ar2-carbonyl, C1-4alkoxycarbonyl, Ar2(CH2)ncarbonyl, aminocarbonyloxy, C1-4alkylcarbonyloxy, Ar2-carbonyloxy, Ar2(CH2)ncarbonyloxy, hydroxy-C2-4-alkyloxy, C1-4alkoxycarbonyl(CH2)noxy, mono- or di(C1-4alkyl)-aminocarbonyl, mono- or di(C1-4alkyl)aminocarbonyloxy, aminosulfonyl, mono- or di(C1-4alkyl)aminosulfonyl, dioxolanyl optionally substituted with one or two C1-6alkyl radicals, and a heterocycle selected from pyrrolidinyl, pyrrolyl, dihydropyrrolyl, thiazolidinyl, imidazolyl, triazo
Type:
Application
Filed:
December 20, 2004
Publication date:
February 5, 2009
Inventors:
Jean-Francois Bonfanti, Koenraad Jozef Lodewijk Andries, Frans Eduard Janssens, Francois Maria Sommen, Jerome Emile Georges Guillemont, Jean Fernand Armand Lacrampe
Publication number: 20080280881
Abstract: The present invention concerns morpholinyl containing benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula a prodrug, N-oxide, addition salt, quaternary amine, metal complex or stereochemically isomeric form thereof wherein G is a direct bond or optionally substituted C1-10alkanediyl; R1 is Ar1 or a monocyclic or bicyclic heterocycle Q is R7, pyrrolidinyl substituted with R7, piperidinyl substituted with R7 or homopiperidinyl substituted with R7; one of R2a and R3a is selected from halo, optionally mono- or polysubstituted C1-6alkyl, optionally mono- or polysubstituted C2-6alkenyl, nitro, hydroxy, Ar2, N(R4aR4b), N(R4aR4b)sulfonyl, N(R4aR4b)carbonyl, C1-6alkyloxy, Ar2oxy, Ar2C1-6alkyloxy, carboxyl, C1-6alkyloxycarbonyl, or —C(=Z)Ar2; and the other one of R2a and R3a is hydrogen; in case R2a is different from hydrogen then R2b is hydrogen, C1-6alkyl or halogen and R3b is hydrogen; in case R3a is different from hydrogen then R3b is hydrogen,
Type:
Application
Filed:
June 17, 2008
Publication date:
November 13, 2008
Inventors:
Jean-Francois Bonfanti, Koenraad Josef Lodewijk Andries, Jerome Michel Claude Fortin, Philippe Muller, Frederic Marc Maurice Doublet, Christophe Meyer, Rudy Edmond Willebrords, Tom Valerius Josepha Gevers, Philip Maria Martha Born Timmerman
Patent number: 7449463
Abstract: The present invention concerns morpholinyl containing benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula a prodrug, N-oxide, addition salt, quaternary amine, metal complex or stereochemically isomeric form thereof wherein G is a direct bond or optionally substituted C1-10alkanediyl; R1 is Ar1 or a monocyclic or bicyclic heterocycle Q is R7, pyrrolidinyl substituted with R7, piperidinyl substituted with R7 or homopiperidinyl substituted with R7; one of R2a and R3a is selected from halo, optionally mono- or polysubstituted C1-6alkyl, optionally mono- or polysubstituted C2-6alkenyl, nitro, hydroxy, Ar2, N(R4aR4b), N(R4aR4b)sulfonyl, N(R4aR4b)carbonyl, C1-6alkyloxy, Ar2oxy, Ar2C1-6alkyloxy, carboxyl, C1-6alkyloxycarbonyl, or —C(=Z)Ar2; and the other one of R2a and R3a is hydrogen; in case R2a is different from hydrogen then R2b is hydrogen, C1-6alkyl or halogen and R3b is hydrogen; in case R3a is different from hydrogen then R3b is hydrogen,
Type:
Grant
Filed:
December 20, 2004
Date of Patent:
November 11, 2008
Assignee:
Tibotec Pharmaceuticals Ltd.
Inventors:
Jean-François Bonfanti, Koenraad Jozef Lodewijk Andries, Jérôme Michel Claude Fortin, Philippe Muller, Frédéric Marc Maurice Doublet, Christophe Meyer, Rudy Edmond Willebrords, Tom Valerius Josepha Gevers, Philip Maria Martha Bern Timmerman
Publication number: 20080146564
Abstract: Novel 1,3-dihydro-benzimidazol-2-ylidene amine derivatives of formula the addition salts and stereochemically isomeric forms wherein each Alk is C1-6alkanediyl; Q is hydrogen; C1-6alkyl substituted with one or two Ar2 radicals; CI1-6alkyl substituted with quinolinyl, oxazolidinyl, thiazolidinyl, morpholinyl, thiomorpholinyl, or with pyrrolidinonyl; —CO—Ar2; or Q is a radical of formula wherein t is 1, 2 or 3; R4 is amino, mono- or di(C1-6alkyl)amino; R1 is Ar2, —CO—Ar2 or a monocyclic or bicyclic heterocycle which may optionally be substituted; R2 is as R1 and additionally can be hydrogen; where Q is other than hydrogen, R3 is hydrogen; and where Q is other than hydrogen, R3 is a radical: wherein R6 is hydrogen, C1-6alkyl, substituted C1-6alkyl; R7, R8, R9 are halo, cyano, C1-6alkyl, substituted C1-6alkyl, C2-6alkenyl, cyanoC2-6alkenyl, C2-6alkynyl, cyanoC2 6alkynyl, Ar1, R10a—0—, R10a —S—, —N(R5aR5b), R10a—O—C(?O)—, N(R5aR5b)—C(?O)—, R10a—C(?O)—NR5b1', R10b—C(?O)—O—; and R8 and/or R9 may also be
Type:
Application
Filed:
March 17, 2006
Publication date:
June 19, 2008
Inventors:
Jean-Francois Bonfanti, Jerome Michel Claude Portin, Ismet Dorange
Publication number: 20080146613
Abstract: The present invention concerns piperidine-amino-benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula their prodrugs, N-oxides, addition salts, quaternary amines, metal complexes and stereochemically isomeric forms wherein Q is C1-6alkyl optionally substituted with trifluoromethyl, C3-7cycloalkyl, Ar2, hydroxy, C1-4alkoxy, C1-4alkylthio, Ar2-oxy-, Ar2-thio-, Ar2(CH2)noxy, Ar2(CH2)nthio, hydroxycarbonyl, aminocarbonyl, C1-4alkyl-carbonyl, Ar2-carbonyl, C1-4alkoxycarbonyl, Ar2(CH2)ncarbonyl, aminocarbonyloxy, C1-4alkylcarbonyloxy, Ar2-carbonyloxy, Ar2(CH2)ncarbonyloxy, C1-4alkoxy-carbonyl(CH2)noxy, mono- or di(C1-4alkyl)aminocarbonyl, mono- or di(C1-4alkyl)-aminocarbonyloxy, aminosulfonyl, mono- or di(C1-4alkyl)aminosulfonyl or a heterocycles selected from the group consisting of pyrrolidinyl, pyrrolyl, dihydropyrrolyl, imidazolyl, triazolyl, piperidinyl, homopiperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, 1-oxo-thiomorpholinyl, 1,1-di
Type:
Application
Filed:
February 13, 2008
Publication date:
June 19, 2008
Inventors:
Jean-Francois BONFANTI, Koenraad Jozef Lodewikjk Andries, Frans Eduard Janssens, Francois Maria Sommen, Jerome Emile Georges Guillemont, Jean Fernand Armand Lacrampe
Patent number: 7355051
Abstract: The present invention concerns piperidine-amino-benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula their prodrugs, N-oxides, addition salts, quaternary amines, metal complexes and stereochemically isomeric forms wherein Q is C1?6alkyl optionally substituted with trifluoromethyl, C3-7cycloalkyl, Ar2, hydroxy, C1?4alkoxy, C1?4alkylthio, Ar2-oxy-, Ar2-thio-, Ar2(CH2)noxy, Ar2(CH2)nthio, hydroxycarbonyl, aminocarbonyl, C1?4alkyl-carbonyl, Ar2carbonyl, C1?4alkoxycarbonyl, Ar2(CH2)ncarbonyl, aminocarbonyloxy, C1?4alkylcarbonyloxy, Ar2carbonyloxy, Ar2(CH2)ncarbonyloxy, C1?4alkoxy-carbonyl(CH2)noxy, mono- or di(C1?4alkyl)aminocarbonyl, mono- or di(C1?4alkyl)-aminocarbonyloxy, aminosulfonyl, mono- or di(C1?4alkyl)aminosulfonyl or a heterocycles selected from the group consisting of pyrrolidinyl, pyrrolyl, dihydropyrrolyl, imidazolyl, triazolyl, piperidinyl, homopiperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, 1-oxo-thiomorpholinyl, 1,1-diox
Type:
Grant
Filed:
December 20, 2004
Date of Patent:
April 8, 2008
Assignee:
Tibotec Pharmaceuticals
Inventors:
Jean-François Bonfanti, Koenraad Jozef Lodewijk Andries, Frans Eduard Janssens, François Maria Sommen, Jerôme Emile Georges Guillemont, Jean Fernand Armand Lacrampe
Publication number: 20070099924
Abstract: Aminobenzimidazoles and benzimidazoles having inhibitory activity on RSV replication and having the formula the prodrugs, N-oxides, addition salts, quaternary amines, metal complexes and stereochemically isomeric forms thereof, wherein G is a direct bond or C1-10alkanediyl optionally substituted with one or more hydroxy, C1-6alkyloxy, Ar1C1-6alkyloxy, C1-6alkylthio, Ar1C1-6alkylthio, HO(—CH2—CH2—O)n—, C1-6alkyloxy(—CH2—CH2—O)n— or Ar1C1-6alkyloxy(—CH2—CH2—O)n—; R1 is Ar1 or a monocyclic or bicyclic heterocycle; Q is hydrogen, amino or mono- or di(C1-4alkyl)amino; one of R2a and R3a is selected from halo, optionally mono- or polysubstituted C1-6alkyl, optionally mono- or polysubstituted C2-6alkenyl, nitro, hydroxy, Ar2, N(R4aR4b), N(R4aR4b)sulfonyl, N(R4aR4b)carbonyl, C1-6alkyloxy, Ar2oxy, Ar2C1-6alkyloxy, carboxyl, C1-6alkyloxycarbonyl, or —C(?Z)Ar2; and the other one of R2a and R3a is hydrogen; in case R2a is different from hydrogen then R2b is hydrogen, C1-6alkyl or halogen and R3b is hydrogen; in case
Type:
Application
Filed:
December 20, 2004
Publication date:
May 3, 2007
Inventors:
Jean-Francois Bonfanti, Koenraad Jozef Lodewijk Andries, Jerome Michel Claude Fortin, Philippe Muller, Frederic Marc Maurice Doublet, Chirstophe Meyer, Rudy Edmond Willebrods, Tom Valerius Josepha Gevers, Philip Maria Martha Bern Timmerman
Publication number: 20070093502
Abstract: The present invention concerns 5- or 6-substituted-benzimidazole derivatives having inhibitory activity on the replication of the respiratory syncytial virus and having the formula a prodrug, N-oxide, addition salt, quaternary amine, metal complex or stereochemically isomeric form thereof wherein Q is Ar2, R6, pyrrolidinyl substituted with R6, piperidinyl substituted with R6 or homopiperidinyl substituted with R6, G is a direct bond or optionally substituted C1-10-alkanediyl; R1 is Ar1 or a monocyclic or bicyclic heterocycle; one of R2a and R2b is cyanoC1-6alkyl, cyanoC2-6alkenyl, Ar3C1-6alkyl, Het-C1-6alkyl, N(R8aR8b)C1-6alkyl, Ar3C2-6alkenyl, Het-C2-6alkenyl, Ar3aminoC1-6alkyl, Het-aminoC1-6alkyl, Ar3thioC1-6alkyl, Het-thioC1-6alkyl, Ar3sulfonylC1-6alkyl, Het-sulfonylC1-6alkyl, Ar3aminocarbonyl, Het-aminocarbonyl, Ar3(CH2)naminocarbonyl, Het-(CH2)naminocarbonyl, Ar3carbonylamino, Het-carbonylamino, Ar3(CH2)ncarbonylamino, Het-(CH2)ncarbonylamino, and the other one of R2a and R2b is hydrogen; in case R
Type:
Application
Filed:
December 20, 2004
Publication date:
April 26, 2007
Inventors:
Jean-Francois Bonfanti, Koenraad Andries, Jerome Fortin, Philippe Muller, Frederic Doublet, Christophe Meyer, Rudy Willebrords, Tom Gevers, Philip Timmerman
Publication number: 20070093659
Abstract: The present invention concerns piperidine-amino-benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula their prodrugs, N-oxides, addition salts, quaternary amines, metal complexes and stereochemically isomeric forms wherein Q is C1-6alkyl optionally substituted with trifluoromethyl, C3-7cycloalkyl, Ar2, hydroxy, C1-4alkoxy, C1-4alkylthio, Ar2-oxy-, Ar2-thio-, Ar2(CH2)noxy, Ar2(CH2)nthio, hydroxycarbonyl, aminocarbonyl, C1-4alkylcarbonyl, Ar2carbonyl, C1-4alkoxycarbonyl, Ar2(CH2)ncarbonyl, aminocarbonyloxy, C1-4alkylcarbonyloxy, Ar2carbonyloxy, Ar2(CH2)ncarbonyloxy, C1-4alkoxy-carbonyl(CH2)noxy, mono- or di(C1-4alkyl)aminocarbonyl, mono- or di(C1-4alkyl)-aminocarbonyloxy, aminosulfonyl, mono- or di(C1-4alkyl)aminosulfonyl or a heterocycles selected from the group consisting of pyrrolidinyl, pyrrolyl, dihydropyrrolyl, imidazolyl, triazolyl, piperidinyl, homopiperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, 1-oxo-thiomorpholinyl, 1,1-diox
Type:
Application
Filed:
December 20, 2004
Publication date:
April 26, 2007
Inventors:
Jean-Francois Bonfanti, Koenraad Andries, Frans Janssens, Francois Sommen, Jerome Guillemont, Jean Lacrampe