Patent number: 6878746
Abstract: A compound selected from these of formula (I): wherein: R1 represents hydrogen, alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, heterocycloalkoxycarbonyl, alkylsulfonyl, arylsulfonyl, arylalkylsulfonyl or phosphono, R2 represents oxygen or sulphur, R3 represents hydrogen or alkyl, cycloalkyl or arylalkyl, X represents linear or branched (C1-C6)alkylene, R4 represents a group selected from amino optionally substituted by one or two groups, —N(R3)—X1—OR5 wherein R3, X1 and R5 are as defined in the description, —N(R3)—X1—NR6R7 wherein R3, X1, R6 and R7 are as defined in the description, hydroxy, alkoxy, aryloxy, —O—X1—OR5 wherein R5 and X1 are as defined in the description, and —O—X1—NR6R7 wherein R6, R7 and X1 are as defined in the description, its isomers, and also addition salts thereof with a pharmaceutically acceptable acid or base, and medical products containing the same which are useful in the treatment of cancer.
Type:
Grant
Filed:
June 19, 2001
Date of Patent:
April 12, 2005
Assignee:
Les Laboratoires Servier
Inventors:
Claude Monneret, Emmanuel Bertounesque, Philippe Meresse, Ghanem Atassi, Alain Pierre, John Hickman, Bruno Pfeiffer, Pierre Renard
Patent number: 6846833
Abstract: Compounds of formula (1): wherein: G represents an optionally substituted phenyl or optionally substituted heterocycle, G1 and G2 being N or C, T1 represents —CH2—CH2—, —CH?CH— or ?CH—CH2—, and T2 is a bond, or T1 represents —CH2— or ?CH— and T2 is —CH2—, ?CH—, R5 represents —(CH2)m—COOR6, R6 and R6? represent hydrogen, alkyl, optionally substituted aryl or optionally substituted arylalkyl, A represents —CO—, —CH2—, ?CH— or —CH? and W represents —CH—, ?C— or —C?, or A represents —CO— or —CH2— and W represents N, X represents —CO—X1—, —CO—NR6—X1—, —NR6—CO—X1—, —O—X1—, —SO2—NR6—X1— or —S(O)n—X1—, Y represents —Y1—, —Y2—Y1— or —Y1—Y2—Y1—, Y1 being an alkylene, alkenylene or alkynylene, and Y2 being an arylene, heteroarylene, cycloalkylene or heterocycloalkylene, Z represents —Z1—, —Z10—NR6—, and —Z10—NR6—CO—, Z1 being a heteroaryl, heterocycloalkyl, heteroarylalkyl, heterocycloalkylalkyl, fused arylheteroaryl, fused arylheterocycloalkyl, fused heteroarylheterocycloalkyl, fused heterocycloalkylheteroar
Type:
Grant
Filed:
March 6, 2001
Date of Patent:
January 25, 2005
Assignee:
Les Laboratories Servier
Inventors:
Patrick Casara, Françoise Perron-Sierra, Ghanem Atassi, Gordon Tucker, Dominique Saint-Dizier
Patent number: 6699876
Abstract: Compound of formula (I):
wherein:
n is 0, 1 or 2,
R1 represents (C3-C11)cycloalkyl or (C3-C11)cycloalkylalkyl,
R2, R3, R4 and R5 are selected from hydrogen, halogen, alkyl, alkenyl, alkynyl, perhaloalkyl, cycloalkyl, cycloalkylalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, acyloxy, carboxy, nitro, cyano, aminocarbonyl (optionally substituted), and the groups (CH2)p—NaRb and —O—C(O)—N—RaRb, with p, Ra and Rb being as defined in the description,
or two adjacent groups R2, R3, R4 and R5 together form a group —O—(CH2)t—O, t being integer from 1 to 3,
R60, R70n, R80 and R90 represent a hydrogen atom, a hydroxy group, an alkoxy group, or an O—(CO)—X or O—(CO)—NXW group as defined in the description,
R61, R71n, R81, and R91 represent a hydrogen atom, alkyl, alkenyl or alkynyl, or taken in pairs together form a bond or an oxirane group, or two groups together form an oxo group.
Type:
Grant
Filed:
November 20, 2002
Date of Patent:
March 2, 2004
Assignee:
Les Laboratoires Servier
Inventors:
Gilbert Lavielle, Patrick Hautefaye, Alain Pierre, Ghanem Atassi, John Hickman, Bernard Cimetiere
Patent number: 6627650
Abstract: A compound of formula (I):
wherein:
R represents hydrogen, optionally substituted alkyl or alkenyl,
R1 to R8, which may be identical or different, each represents hydrogen, optionally substituted alkyl, hydroxy, acyloxy, optionally substituted amino, carboxy, optionally substituted alkoxy, or alkenyloxy, or one of R1 to R8 forms, with another of R1 to R8 that is adjacent, an alkylenedioxy group,
X represents oxygen or NR16 wherein R16 represents hydrogen, alkyl, aryl or arylalkyl,
R9 represents hydrogen, aryl, heteroaryl, or optionally substituted, saturated or unsaturated alkyl,
an isomer thereof, or an addition salt thereof with a pharmaceutically acceptable acid or base.
Medicinal products containing the same which are useful as anti-cancer agents.
Type:
Grant
Filed:
June 13, 2002
Date of Patent:
September 30, 2003
Assignee:
Les Laboratoires Servier
Inventors:
Michel Wierzbicki, Marie-Françoise Boussard, Anne Rousseau, Ghanem Atassi, John Hickman, Alain Pierre, Stéphane Leonce, Nicolas Guilbaut, Laurence Kraus-Berthier
Patent number: 6605604
Abstract: The invention concerns a compound of formula (I) wherein: n is equal to 0 or 1; R1, R2, R3, R4 represent a hydrogen or an alkyl group, or R1 and R3 together form a cycloalkyl group; R5 represents a hydrogen, an alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, hetereoalkylalkyl, hetereocycloalkyl, hetereocycloalkylalkyl group (all optionally substituted), or a —CO—R6 group; and R6 represents R7 or OR7 or NR7R8, with R7 representing an aryl, arylalkyl, heteroaryl or heteroarylalkyl, heterocycloalkyl, heterocycloalkylalkyl group (all optionally substituted), and R8 representing an alkyl, aryl, arylalkyl, heteroaryl or heteroarylalkyl (all optionally substituted); or R5 and R6 form with the nitrogen atom and the Z group bearing them a saturated monocyclic, bicyclic or tricyclic group, partially unsaturated or unsaturated, with 5 to 16 chain links containing 1 to 7 heteroatoms and optionally substituted; R10 represents a hydrogen atom or a hydroxy group, and in the latter case R1, R2, R
Type:
Grant
Filed:
December 26, 2000
Date of Patent:
August 12, 2003
Assignee:
Les Laboratoires Servier
Inventors:
Patrick Casara, Anne Marie Chollet, Thierry Le Diguarher, Ghanem Atassi, Jacqueline Bonnet, Alain Pierre, Massimo Sabatini, Gordon Tucker, Nicolas Guilbaud
Patent number: 6569858
Abstract: A compound selected from those of formula (I):
wherein:
R1 and R2, which may be identical or different, represent a group of formula U-V wherein U represents single bond, or alkylene which is optionally substituted and/or unsaturated, and V is as defined in the description,
G represents oxygen, or NR3 wherein R3 is as defined in the description,
X represents hydrogen, hydroxy, alkoxy, mercapto or alkylthio, Y represents hydrogen, or X+Y represents carbonyl,
X1 represents hydrogen, hydroxy, alkoxy, mercapto or alkylthio, Y1 represents hydrogen, or X1+Y1 represents carbonyl,
R4, R5, and R6 are as defined in the description,
its isomers, and pharmaceutically-acceptable acid or base addition salts thereof, and medicinal products containing the same are useful in the treatment of cancer.
Type:
Grant
Filed:
November 5, 2001
Date of Patent:
May 27, 2003
Assignee:
Les Laboratoires Servier
Inventors:
Michelle Prudhomme, Pascale Moreau, Fabrice Anizon, Christelle Marminon, Ghanem Atassi, Alain Pierre, Bruno Pfeiffer, Pierre Renard
Patent number: 6509345
Abstract: Compound of formula (I):
wherein:
n is 0, 1 or 2,
R1, R2, R3, R4 and R5 are selected from hydrogen, halogen, alkyl, alkenyl, alkynyl, perhaloalkyl, cycloalkyl, cycloalkylalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, alkoxycarbonyl, acyloxy, carboxy, nitro, cyano, aminocarbonyl (optionally substituted), and the groups (CH2)p—NRaRb and —O—C(O)—N—RaRb, with p, Ra and Rb being as defined in the description, or two adjacent groups R2, R3, R4 and R5 together form a group —O—(CH2)t—O, t being an integer from 1 to 3,
R60, R70n, R80 and R90 represent a hydrogen atom, a hydroxy group, an alkoxy group, or an O—(CO)—X or O—(CO)—NXW group as defined in the description,
R61, R71n, R81 and R91 represent a hydrogen atom, alkyl, alkenyl or alkynyl, or taken in pairs together form a bond or an oxirane group, or two groups together form an oxo group.
Type:
Grant
Filed:
November 5, 2001
Date of Patent:
January 21, 2003
Assignee:
Les Laboratoires Servier
Inventors:
Gilbert Lavielle, Patrick Hautefaye, Alain Pierre, Ghanem Atassi, John Hickman, Bernard Cimetiere
Patent number: 6503919
Abstract: A compound selected from those of formula (I):
wherein:
X and Y represent hydrogen, halogen, hydroxy, mercapto, cyano, nitro, alkyl, alkoxy, trihaloalkyl, optionally substituted amino, methylenedioxy, or ethylenedioxy,
R1 represents hydrogen, or alkyl,
R2 represents hydrogen, hydroxy, alkyl, alkoxy, alkylcarbonyloxy, or optionally substituted amino,
R3 and R4 represent hydrogen, or alkyl,
R5 and R6 represent —O—CO—U—V wherein U and V are as defined in the description, or Z as defined in the description, it being understood that at least one of the R5 and R6 groups represents —O—CO—U—V,
their isomers, N-oxides, and pharmaceutically-acceptable acid or base addition salts thereof, and medicinal products containing the same which are useful in the treatment of cancer.
Type:
Grant
Filed:
June 15, 2000
Date of Patent:
January 7, 2003
Assignee:
Les Laboratoires Server
Inventors:
Michel Koch, François Tillequin, Sylvie Michel, Ghanem Atassi, Alain Pierre, Pierre Renard, Bruno Pfeiffer
Patent number: 6300340
Abstract: A compound of formula (I)
in which:
m, and n, which may be identical or different, represent 0 or 1,
X and Y, which may be identical or different, represent hydrogen or halogen or alkyl, trihaloalkyl, alkoxy, hydroxyl, cyano, nitro, amino, alkylamino, or dialkylamino,
Z represent a linear or branched C4 to C12 alkylene chain in which one or more —CH2— are optionally replaced by any one of the following atoms or groups: —NR—, —O—, —S—, —SO—, SO2—, or —CONH—, or by a substituted or unsubstituted heterocylcic,
A forms, with two adjacent carbon atoms of the phenyl ring, a phenyl, naphthyl or tetrahydronaphthyl ring or a heterocycle,
represents any one of the groups as defined in the description, its optical isomers and its addition salts with a pharamaceutically and acceptable acid or base, and medicinal products containing the same which are useful as anticancer agents.
Type:
Grant
Filed:
July 14, 2000
Date of Patent:
October 9, 2001
Assignee:
Adir et Compagnie
Inventors:
Gilbert Lavielle, Patrick Hautefaye, Ghanem Atassi, Alain Pierre, Laurence Kraus-Berthier, Stéphane Leonce
Patent number: 6288073
Abstract: A compound selected from those of formula (I):
in which:
X and Y represent hydrogen, halogen, hydroxy, mercapto, cyano, nitro, alkyl, alkoxy, trihaloalkyl, optionally substituted amino, methylenedioxy, or ethylenedioxy,
R1 represents hydrogen, or alkyl,
R2 represents hydrogen, hydroxy, alkyl, alkoxy, alkylcarbonyloxy, or optionally substituted ammo,
R3 and R4 represent hydrogen, or alkyl,
A represents —CH═CH—, or —CH(R5)—CH(R6)— wherein R5 and R6 are as defined in the description,
their isomers, N-oxides, and pharmaceutically-acceptable acid or base addition salts thereof,
and medicinal products containing the same which are useful in the treatment of cancer.
Type:
Grant
Filed:
June 19, 2000
Date of Patent:
September 11, 2001
Assignee:
Adir et Compagnie
Inventors:
Michel Koch, François Tillequin, Sylvie Michel, Ghanem Atassi, Alain Pierre, Bruno Pfeiffer, Pierre Renard
Patent number: 6281198
Abstract: Compound of formula (I):
wherein:
R represents:
a group of formula (i):
wherein X, Y and W are as defined in the description,
or a group of formula (ii):
—A—G (ii)
wherein:
A represents a single bond or an optionally substituted alkylene chain,
G represents a group selected from hydrogen, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —OR2, —O—T1—NR3R4, —O—T1—NR2—T′1—NR3R4, —NR3R4, —NR2—T1—NR3R4, —NR2—T1—OR5, —NR2—T1—CO2R6, —NR2—T1—C(O)R6, —C(O)—NR3R4, —C(O)—NR2—T2, —O—C(O)T2, —O—C(S)—T2, —NR2—C(O)—T2, —NR2—C(S)—T2, —O—C(O)—O—T2, —O—C(O)—NR2—T2, —O—C(S)—O—T2, —O—C(S)—NR2—T2, —NR2—C(O)—O—T2,
Type:
Grant
Filed:
October 26, 2000
Date of Patent:
August 28, 2001
Assignee:
Adir et Compagnie
Inventors:
Claude Monneret, Emmanuel Bertounesque, Philippe Meresse, Ghanem Atassi, Alain Pierre, Bruno Pfeiffer, Pierre Renard