公开(公告)号：US08153640B2

公开(公告)日：2012-04-10

申请号：US11718181

申请日：2005-10-27

申请人： Jerôme Emile Georges Guillemont ,  Mikaël Paugam ,  Bruno Francois Marie Delest ,  Jan Heeres ,  Paulus Joannes Lewi ,  Paul Adriaan Jan Janssen ,  Frank Xavier Jozef Herwig Arts, legal representative

发明人： Jerôme Emile Georges Guillemont ,  Mikaël Paugam ,  Bruno Francois Marie Delest ,  Jan Heeres ,  Paulus Joannes Lewi ,  Paul Adriaan Jan Janssen

IPC分类号： C07D473/32 ,  A61K31/52 ,  A61P31/18

CPC分类号： C07D487/04 ,  C07D473/00 ,  C07D473/16 ,  C07D473/24 ,  C07D473/34

摘要： HIV replication inhibitors of formula N-oxides, pharmaceutically acceptable addition salts, quaternary amines or stereoisomeric forms thereof, wherein -a1=a2-a3=a4- is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; -b1=b2-b3=b4- is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; n and m is 0, 1, 2, 3 and in certain cases also 4; R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; optionally substituted C1-6alkyl; C1-6alkyloxycarbonyl; R2 is OH; halo; optionally substituted C1-6alkyl, C2-6alkenyl or C2-6alkynyl; substituted carbonyl; carboxyl; CN; nitro; amino; substituted amino; polyhalomethyl; polyhalomethylthio; —S(═O)pR6; C(═NH)R6; R2a is CN; amino; substituted amino; optionally substituted C1-6alkyl; halo; optionally substituted C1-6alkyloxy; substituted carbonyl; —CH═N—NH—C(═O)—R16; optionally substituted C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl or C2-6alkynyl; —C(═N—O—R8)—C1-4alkyl; R7 or —X—R7; R3 is CN; amino; C1-6alkyl; halo; optionally substituted C1-6alkyloxy; substituted carbonyl; —CH═N—NH—C(═O)—R16; substituted C1-6alkyl; optionally substituted C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl or C2-6alkynyl; —C(═N—O—R8)—C1-4alkyl; R7; —X—R7; R4 is halo; OH; optionally substituted C1-6alkyl, C2-6alkenyl or C2-6alkynyl; C3-7cycloalkyl; C1-6alkyloxy; CN; nitro; polyhaloC1-6alkyl; polyhaloC1-6alkyloxy; substituted carbonyl; formyl; amino; mono- or di(C1-4alkyl)amino or R7; -A-B— is —CR5═N—, —N═N—, —CH2—CH2—, —CS—NH—, —CO—NH—, —CH═CH—; pharmaceutical compositions comprising these; methods for the preparation of these compounds and compositions; the use of these compounds for the prevention or the treatment of HIV infection.

公开(公告)号：US09487518B2

公开(公告)日：2016-11-08

申请号：US13410779

申请日：2012-03-02

申请人： Jerôme Emile Georges Guillemont ,  Mikaël Paugam ,  Bruno Francois Marie Delest ,  Jan Heeres ,  Paulus Joannes Lewi ,  Paul Adriaan Jan Janssen ,  Frank Xavier Jozef Herwig Arts

发明人： Jerôme Emile Georges Guillemont ,  Mikaël Paugam ,  Bruno Francois Marie Delest ,  Jan Heeres ,  Paulus Joannes Lewi ,  Paul Adriaan Jan Janssen

IPC分类号： C07D487/04 ,  A61K31/519 ,  C07D473/00 ,  C07D473/34 ,  A61P31/18 ,  A61K31/52

CPC分类号： C07D487/04 ,  C07D473/00 ,  C07D473/16 ,  C07D473/24 ,  C07D473/34

摘要： HIV replication inhibitors of formula wherein -a1=a2-a3=a4- is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; -b1=b2-b3=b4- is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; n and m is 0-4, R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; C1-6alkyl; C1-6alkyloxycarbonyl; R2 is OH; halo; C1-6alkyl, C2-6alkenyl or C2-6alkynyl; substituted carbonyl; carboxyl; CN; nitro; amino; polyhalomethyl; polyhalomethylthio; —S(═O)pR6; C(═NH)R6; R2a is CN; amino; substituted amino; C1-6alkyl; halo; C1-6alkyloxy; carbonyl; —CH═N—NH—C(═O)—R16; C1-6alkyloxyC1-6alkyl; C2-6alkenyl or C2-6alkynyl; —C(═N—O—R8)—C1-4alkyl; R7 or —X—R7; R3 is CN; amino; C1-6alkyl; halo; C1-6alkyloxy; substituted carbonyl; —CH═N—NH—C(═O)—R16; substituted C1-6alkyl; C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl or C2-6alkynyl; —C(═N—O—R8)—C1-4alkyl; R7; —X—R7; R4 is halo; OH; C1-6alkyl, C2-6alkenyl or C2-6alkynyl; C3-7cycloalkyl; C1-6alkyloxy; CN; nitro; polyhaloC1-6alkyl; polyhaloC1-6alkyloxy; substituted carbonyl; formyl; amino; mono- or di(C1-4alkyl)amino or R7; -A-B— is —CR5═N—, —N═N—, —CH2—CH2—, —CS—NH—, —CO—NH—, —CH═CH—; and the use of these compounds for the prevention or the treatment of HIV infection.

公开(公告)号：US20120190697A1

公开(公告)日：2012-07-26

申请号：US13410779

申请日：2012-03-02

申请人： Jerôme Emile Georges GUILLEMONT ,  Mikaël Paugam ,  Bruno Francois Marie Delest ,  Jan Heeres ,  Paulus Joannes Lewi ,  Frank Xavier Jozef Herwig Arts

发明人： Jerôme Emile Georges GUILLEMONT ,  Mikaël Paugam ,  Bruno Francois Marie Delest ,  Jan Heeres ,  Paulus Joannes Lewi ,  Frank Xavier Jozef Herwig Arts

IPC分类号： A61K31/52 ,  A61P31/18 ,  C07D473/32 ,  C07D487/04 ,  A61K31/519

CPC分类号： C07D487/04 ,  C07D473/00 ,  C07D473/16 ,  C07D473/24 ,  C07D473/34

摘要： HIV replication inhibitors of formula wherein -a1=a2-a3=a4- is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; -b1=b2-b3=b4- is —CH═CH—CH═CH—, —N═CH—CH═CH—, —N═CH—N═CH—, —N═CH—CH═N—, —N═N—CH═CH—; n and m is 0-4, R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; C1-6alkyl; C1-6alkyloxycarbonyl; R2 is OH; halo; C1-6alkyl, C2-6alkenyl or C2-6alkynyl; substituted carbonyl; carboxyl; CN; nitro; amino; polyhalomethyl; polyhalomethylthio; —S(═O)pR6; C(═NH)R6; R2a is CN; amino; substituted amino; C1-6alkyl; halo; C1-6alkyloxy; carbonyl; —CH═N—NH—C(═O)—R16; C1-6alkyloxyC1-6alkyl; C2-6alkenyl or C2-6alkynyl; —C(═N—O—R8)—C1-4alkyl; R7 or —X—R7; R3 is CN; amino; C1-6alkyl; halo; C1-6alkyloxy; substituted carbonyl; —CH═N—NH—C(═O)—R16; substituted C1-6alkyl; C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl or C2-6alkynyl; —C(═N—O—R8)—C1-4alkyl; R7; —X—R7; R4 is halo; OH; C1-6alkyl, C2-6alkenyl or C2-6alkynyl; C3-7cycloalkyl; C1-6alkyloxy; CN; nitro; polyhaloC1-6alkyl; polyhaloC1-6alkyloxy; substituted carbonyl; formyl; amino; mono- or di(C1-4alkyl)amino or R7; -A-B— is —CR5═N—, —N═N—, —CH2—CH2—, —CS—NH—, —CO—NH—, —CH═CH—; and the use of these compounds for the prevention or the treatment of HIV infection.