Patent number: 7741325
Abstract: A compound selected from those of formula (I): wherein: B1, B2 represent carbon or nitrogen, X, Y, X1 and Y1 represent a group selected from hydrogen, halogen, hydroxy, alkoxy, nitro, cyano, trihaloalkyl and NRaRb wherein Ra and Rb are as defined in the description, R1 represents hydrogen or alkyl, R2 represents a group selected from hydrogen, alkyl, —OR?a, —NR?aR?b, —O-Ta-OR?a, —NR?a-Ta-NR?aR?b, NR?a—C(O)-TaH, —O—C(O)-TaH, —O-Ta-NRa?Rb?, —NR?a-Ta-OR?a, —NR?a-Ta-CO2R?a and —NR?a—C(O)-Ta-NR?aR?b wherein R?a, R?b, R?a and Ta are as defined in the description, R3, R4 represent hydrogen or alkyl, A represents a group of formula —CH(R5)—CH(R6)—, —CH?C(R7)—, —C(R7)?CH—, —C(O)—CH(R8)— or —CH(R8)—C(O)— wherein R5, R6, R7 and R8 are as defined in the description, its isomers, N-oxides, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.
Type:
Grant
Filed:
January 31, 2005
Date of Patent:
June 22, 2010
Inventors:
Michel Koch, François Tillequin, Sylvie Michel, John Hickman, Alain Pierre, Stéphane Leonce, Bruno Pfeiffer, Pierre Renard
Patent number: 7378419
Abstract: The invention relates to compounds of formula (I), wherein R1 is a group selected from hydrogen, alkyl, aryl, aryalkil, heteroaryl, heteroarylalkyl, alkylcarbonyl, arylcarbonyl, arylalkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, heterocycloalkoxycarbonyl, alkylsulfonyl, arylsulfonyl, arylalkylsulfonyl, phosphonic and Si(Ra)2Rb, Y is a group selected from HN—NH and N—R2, R3 is a hydrogen atom, an alkyl, cycloalkyl, aryl, arylalkyl group, R4 is hydrogen atom or an alkyl group, enantiomers, diastereoisomers and the salts thereof
Type:
Grant
Filed:
September 1, 2004
Date of Patent:
May 27, 2008
Assignees:
Les Laboratoires Servier, Centre National de la Recherche Scientifique (CNRS)
Inventors:
Claude Monneret, Daniel Dauzonne, John Hickman, Alain Pierre, Laurence Kraus-Berthier, Bruno Pfeiffer, Pierre Benard
Patent number: 7276512
Abstract: A compound selected from those of formula (I): wherein: X and Y represent a group selected from hydrogen, halogen, hydroxy, alkoxy, nitro, cyano, alkyl, trihaloalkyl and NRaRb, wherein Ra and Rb are as defined in the description R1 represents hydrogen or alkyl R2 represents a group selected from hydrogen, alkyl, —OR?a, —NR?aR?b, —O-Ta-OR?a, —NR?a-Ta-NR?aR?b, —NR?a—C(O)-TaH, —O—C(O)-TaH, —O-Ta-NR?aR?b, —NR?a-Ta-OR?a, —NR?a-Ta-CO2R?a and —NR?a—C(O)-Ta-NR?aR?b, wherein R?a, R?a, R?b and Ta are as defined in the description R3 and R4 represent hydrogen or alkyl A represents a group of formula —CH(R5)—CH(R6)—, —CH?C(R7)—, —C(R7)?CH—, —C(O)—CH(R8) or —CH(R8)—C(O), wherein R5, R6, R7 and R8 are as defined in the description its isomers, N-oxides, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.
Type:
Grant
Filed:
June 18, 2004
Date of Patent:
October 2, 2007
Assignee:
Les Laboratoires Servier
Inventors:
Michel Koch, François Tillequin, Sylvie Michel, John Hickman, Alain Pierre, Stéphane Leonce, Bruno Pfeiffer, Pierre Renard
Patent number: 7151108
Abstract: A compound selected from those of formula (I): wherein: W1 represents, together with carbon to which it is bonded, phenyl, pyridyl, Z represents a group of formula U—V as defined in the description, Q1 represents oxygen, NR2 as defined in the description, Q2 represents oxygen, NR?2 as defined in the description, X1, X2, X?1 and X?2 each represents hydrogen, hydroxy, alkoxy, mercapto or alkylthio, Y1, Y2, Y?1 and Y?2 each represents hydrogen, or X1 and Y1, X2 and Y2, X?1 and Y?1, X?2 and Y?2 with carbon carrying them, together form carbonyl or thiocarbonyl, R1 is as defined in the description, its isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.
Type:
Grant
Filed:
September 26, 2003
Date of Patent:
December 19, 2006
Assignee:
Les Laboratories Servier
Inventors:
Michelle Prudhomme, Bernadette Hugon, Fabrice Anizon, John Hickman, Alain Pierre, Roy Golsteyn, Pierre Renard, Bruno Pfeiffer
Patent number: 7144891
Abstract: A compound selected from those of formula (I): wherein: X and Y represent a group selected from hydrogen, halogen, alkoxy, nitro, cyano, alkyl, alkenyl, polyhaloalkyl and —NRaRb wherein Ra and Rb are as defined in the description, Z represents oxygen or NRc wherein Rc is as defined in the description, Ar represents aryl or heteroaryl, R1 represents hydrogen or alkyl, R2 represents a group selected from hydrogen, alkyl, —ORa and —NRaRb wherein Ra and Rb are as defined in the description, R3 and R4 represent hydrogen or alkyl, R5 represents hydrogen, ORc, NRcRd, W1—C(W2)—U—V, W1—C(W2)—W3-T1 or Z-CO—CH?CHAr wherein Rc, Rd, W1, W2, W3, U, V, T, Z and Ar are as defined in the description, its isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.
Type:
Grant
Filed:
December 21, 2005
Date of Patent:
December 5, 2006
Assignees:
Les Laboratoires Servier, Centre National de la Recherche Scientifique, University Rene Descartes Paris V
Inventors:
Michel Koch, François Tillequin, Sylvie Michel, John Hickman, Alain Pierre, Stéphane Leonce, Bruno Pfeiffer, Laurence Kraus-Berthier
Publication number: 20060247246
Abstract: The invention relates to compounds of formula (I), wherein R1 is a group selected from hydrogen, alkyl, aryl, aryalkil, heteroaryl, heteroarylalkyl, alkylcarbonyl, arylcarbonyl, arylalkylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, heterocycloalkoxycarbonyl, alkylsulfonyl, arylsulfonyl, arylalkylsulfonyl, phosphonic and Si(Ra)2Rb, Y is a group selected from HN—NH and N—R2, R3 is a hydrogen atom, an alkyl, cycloalkyl, aryl, arylalkyl group, R4 is hydrogen atom or an alkyl group, enantiomers, diastereoisomers and the salts thereof.
Type:
Application
Filed:
September 1, 2004
Publication date:
November 2, 2006
Inventors:
Claude Monneret, Daniel Dauzonne, John Hickman, Alain Pierre, Laurence Kraus-Berthier, Bruno Pfeiffer, Pierre Benard
Patent number: 7098220
Abstract: Compounds of formula (I): wherein: R1 represents hydrogen, halogen, alkyl, polyhaloalkyl, cyano, nitro, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, R2 represents hydrogen, alkyl, an optionally substituted aryl, optionally substituted heteroaryl, or R20—C(X)— wherein: R20 represents alkyl, alkoxy, amino, alkylamino, dialkylamino, optionally substituted aryl or optionally substituted heteroaryl, X represents oxygen, sulphur, or NR21 wherein R21 represents hydrogen or alkyl, R3 represents hydrogen atom or alkyl, n represents integer from 1 to 6 inclusive, the representation its enantiomers, diastereoisomers and also addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful as AMPK activators.
Type:
Grant
Filed:
November 4, 2003
Date of Patent:
August 29, 2006
Assignee:
Les Laboratoires Servier
Inventors:
Sylvain Rault, Jean-Charles Lancelot, Marina Kopp, Daniel-Henri Caignard, Bruno Pfeiffer, Jean-Guy Bizot-Espiard, Pierre Renard
Publication number: 20060135545
Abstract: A compound selected from those of formula (I): wherein: X and Y represent a group selected from hydrogen, halogen, alkoxy, nitro, cyano, alkyl, alkenyl, polyhaloalkyl and —NRaRb wherein Ra and Rb are as defined in the description, Z represents oxygen or NRc wherein Rc is as defined in the description, Ar represents aryl or heteroaryl, R1 represents hydrogen or alkyl, R2 represents a group selected from hydrogen, alkyl, —ORa and —NRaRb wherein Ra and Rb are as defined in the description, R3 and R4 represent hydrogen or alkyl, R5 represents hydrogen, ORc, NRcRd, W1—C(W2)—U—V, W1—C(W2)—W3-T1 or Z-CO—CH?CHAr wherein Rc, Rd, W1, W2, W3, U, V, T, Z and Ar are as defined in the description, its isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.
Type:
Application
Filed:
December 21, 2005
Publication date:
June 22, 2006
Inventors:
Michel Koch, Francois Tillequin, Sylvie Michel, John Hickman, Alain Pierre, Stephane Leonce, Bruno Pfeiffer, Laurence Kraus-Berthier
Patent number: 7056929
Abstract: A method for treating a living body afflicted with a cancer selected from lung and ovarian carcinoma, comprising the step of administering to the living animal body an amount of 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, or X and Y together form a methylenedioxy or ethylenedioxy, 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)— wherein R5, R6, R7 and R8 are as defined in the descript
Type:
Grant
Filed:
July 26, 2003
Date of Patent:
June 6, 2006
Assignee:
Les Laboratoires Servier
Inventors:
Michel Koch, Francois Tillequin, Sylvie Michel, Elisabeth Seguin, Abdelhakim El Omri, John Hickman, Alain Pierre, Bruno Pfeiffer, Pierre Renard
Publication number: 20060069117
Abstract: Compounds of formula (I): wherein: R1 represents hydrogen, halogen, alkyl, polyhaloalkyl, cyano, nitro, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, R2 represents hydrogen, alkyl, an optionally substituted aryl, optionally substituted heteroaryl, or R20—C(X)— wherein: R20 represents alkyl, alkoxy, amino, alkylamino, dialkylamino, optionally substituted aryl or optionally substituted heteroaryl, X represents oxygen, sulphur, or NR21 wherein R21 represents hydrogen or alkyl, R3 represents hydrogen atom or alkyl, n represents integer from 1 to 6 inclusive, the representation its enantiomers, diastereoisomers and also addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful as AMPK activators.
Type:
Application
Filed:
November 4, 2003
Publication date:
March 30, 2006
Inventors:
Sylvain Rault, Jean-Charles Lancelot, Marina Kopp, Daniel-Henri Caignard, Bruno Pfeiffer, Jean-Guy Bizot-Espiard, Pierre Renard
Publication number: 20050171114
Abstract: A compound selected from those of formula (I): wherein: B1, B2 represent carbon or nitrogen, X, Y, X1 and Y1 represent a group selected from hydrogen, halogen, hydroxy, alkoxy, nitro, cyano, trihaloalkyl and NRaRb wherein Ra and Rb are as defined in the description, R1 represents hydrogen or alkyl, R2 represents a group selected from hydrogen, alkyl, —OR?a, —NR?aR?b, —O-Ta-OR?a, —NR?a-Ta-NR?aR?b, NR?a—C(O)-TaH, —O—C(O)-TaH, —O-Ta-NRa?Rb?, —NR?a-Ta-OR?a, —NR?a-Ta-CO2R?a and —NR?a—C(O)-Ta-NR?aR?b wherein R?a, R?b, R?a and Ta are as defined in the description, R3, R4 represent hydrogen or alkyl, A represents a group of formula —CH(R5)—CH(R6)—, —CH?C(R7)—, —C(R7)?CH—, —C(O)—CH(R8)— or —CH(R8)—C(O)— wherein R5, R6, R7 and R8 are as defined in the description, its isomers, N-oxides, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.
Type:
Application
Filed:
January 31, 2005
Publication date:
August 4, 2005
Inventors:
Michel Koch, Francois Tillequin, Sylvie Michel, John Hickman, Alain Pierre, Stephane Leonce, Bruno Pfeiffer, Pierre Renard