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: 6642248
Abstract: A compound selected from those of formula (I):
wherein:
X and Y represent group selected from hydrogen, halogen, mercapto, cyano, nitro, alkyl, trihaloalkyl, trihaloalkylcarbonylamino, —ORa, —NRaRb, —NRa—C(O)—T1, —O—C(O)—T1, —O—T2-NRaRb, —O—T2-ORa, —NRa—T2-NRaRb, —NRa—T2-ORa and —NRa—T2-CO2Ra wherein Ra, Rb, T1, T2 are as defined in the description,
R1 represents hydrogen or alkyl,
R2 represents a group selected from hydrogen, —ORa, —NRaRb, —NRa—C(O)—T1, —O—C(O)—T1, —O—T2-NRaRb, —O—T2-ORa, —NRa—T2-NRaRb, —NRa—T2-ORa and —NRa—T2-CO2Ra wherein Ra, Rb, T1 and T2 are as defined hereinbefore,
R3 and R4 represent hydrogen or alkyl,
W represents a group of formula —CH(R5)—CH(R6)—, —CH═C(R7)—, —C(R7)═CH— or —C(O)—CH(R8)
Type:
Grant
Filed:
July 25, 2002
Date of Patent:
November 4, 2003
Assignee:
Les Laboratories Servier
Inventors:
Michel Koch, François Tillequin, Sylvie Michel, Elisabeth Seguin, Abdelhakim El Omri, John Hickman, Alain Pierre, Bruno Pfeiffer, Pierre Renard
Patent number: 6638962
Abstract: Compound of formula (I):
wherein:
X represents a bond or alkylene, CO, S(O)n, —S(O)n—A1—, —CO—A1—, —A—S(O)n—A′1— or —A1—CO—A′1—,
Y represents aryl, heteroaryl, cycloalkyl or heterocycloalkyl, each unsubstituted or substituted,
R1, R2, R3 and R4 each independently of the others represent hydrogen or aryl, heteroaryl, cycloalkyl or heterocycloalkyl, each unsubstituted or substituted,
or R1, R2, R3 and R4, taken in pairs, together form a bond, or form a fused benzene ring or a fused aromatic or partially unsaturated heterocycle,
T represents —CH(R5)—, —N(R5)— or —N(R5)CO—,
V represents hydrogen or unsubstituted or substituted aryl or heteroaryl,
A2 represents [C(R6)(R′6)]p,
R7 and R8 are as defined in the description,
their isomers and addition salts thereof with a pharmaceutically acceptable acid or base and medicinal products containing t
Type:
Grant
Filed:
January 16, 2002
Date of Patent:
October 28, 2003
Assignee:
Les Laboratoires Servier
Inventors:
Patrick Casara, Thierry Le Diguarher, Gilbert Dorey, John Hickman, Alain Pierre, Gordon Tucker, Nicolas Guilbaud
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