ZA200108174B - Amine derivatives. - Google Patents
Amine derivatives. Download PDFInfo
- Publication number
- ZA200108174B ZA200108174B ZA200108174A ZA200108174A ZA200108174B ZA 200108174 B ZA200108174 B ZA 200108174B ZA 200108174 A ZA200108174 A ZA 200108174A ZA 200108174 A ZA200108174 A ZA 200108174A ZA 200108174 B ZA200108174 B ZA 200108174B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- substituents
- phenyl
- substituent
- dioxothiazolidin
- Prior art date
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- 150000001412 amines Chemical class 0.000 title claims description 48
- -1 thiocarbamoyl group Chemical group 0.000 claims description 472
- 125000001424 substituent group Chemical group 0.000 claims description 275
- 229910052799 carbon Inorganic materials 0.000 claims description 141
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 125000003545 alkoxy group Chemical group 0.000 claims description 61
- 125000001188 haloalkyl group Chemical group 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
- 125000001931 aliphatic group Chemical group 0.000 claims description 28
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 208000002249 Diabetes Complications Diseases 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000008280 blood Substances 0.000 claims description 7
- 210000004369 blood Anatomy 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 206010012655 Diabetic complications Diseases 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims description 4
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims description 4
- 102000004877 Insulin Human genes 0.000 claims description 4
- 108090001061 Insulin Proteins 0.000 claims description 4
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims description 4
- 210000001789 adipocyte Anatomy 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229940125396 insulin Drugs 0.000 claims description 4
- 230000035935 pregnancy Effects 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 28
- 239000000126 substance Substances 0.000 claims 26
- 238000000034 method Methods 0.000 claims 18
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 12
- 230000002265 prevention Effects 0.000 claims 11
- 150000002148 esters Chemical class 0.000 claims 4
- 230000005764 inhibitory process Effects 0.000 claims 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 4
- HRVHYQTUUKZNQA-UHFFFAOYSA-N 1-(1-adamantyl)-3-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]urea Chemical compound N=1C2=CC=C(OC=3C=CC(NC(=O)NC45CC6CC(CC(C6)C4)C5)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O HRVHYQTUUKZNQA-UHFFFAOYSA-N 0.000 claims 2
- MZTARCWHBSKQLJ-UHFFFAOYSA-N 1-[3-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]-3-(4-fluorophenyl)urea Chemical compound N=1C2=CC=C(OC=3C=C(NC(=O)NC=4C=CC(F)=CC=4)C=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O MZTARCWHBSKQLJ-UHFFFAOYSA-N 0.000 claims 2
- JWDLDMREELAJRV-UHFFFAOYSA-N 1-[3-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1C2=CC=C(OC=3C=C(NC(=O)NC=4C=CC(=CC=4)C(F)(F)F)C=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O JWDLDMREELAJRV-UHFFFAOYSA-N 0.000 claims 2
- YDEGXCNOYYMTJY-UHFFFAOYSA-N 1-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1OC1=CC=C(N=C(COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)N2C)C2=C1 YDEGXCNOYYMTJY-UHFFFAOYSA-N 0.000 claims 2
- NAAINBRRQYPYHN-UHFFFAOYSA-N 1-benzyl-3-[7-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxynaphthalen-1-yl]urea Chemical compound N=1C2=CC=C(OC=3C=C4C(NC(=O)NCC=5C=CC=CC=5)=CC=CC4=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O NAAINBRRQYPYHN-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 230000010261 cell growth Effects 0.000 claims 2
- YKCBEIZLLMXLOX-UHFFFAOYSA-N n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]-2,4-difluorobenzamide Chemical compound N=1C2=CC=C(OC=3C=CC(NC(=O)C=4C(=CC(F)=CC=4)F)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O YKCBEIZLLMXLOX-UHFFFAOYSA-N 0.000 claims 2
- REPMYONBPYQSHL-UHFFFAOYSA-N n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]methanesulfonamide Chemical compound N=1C2=CC=C(OC=3C=CC(NS(C)(=O)=O)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O REPMYONBPYQSHL-UHFFFAOYSA-N 0.000 claims 2
- UEWDVSOOYKEZLG-UHFFFAOYSA-N n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]pyridine-3-carboxamide Chemical compound N=1C2=CC=C(OC=3C=CC(NC(=O)C=4C=NC=CC=4)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O UEWDVSOOYKEZLG-UHFFFAOYSA-N 0.000 claims 2
- CWHIFRHINCOTPM-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-[2-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]ethyl]urea Chemical compound N=1C2=CC=C(OC=3C=CC(CCNC(=O)NC=4C(=CC(F)=CC=4)F)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O CWHIFRHINCOTPM-UHFFFAOYSA-N 0.000 claims 1
- UAGOWIAHMMDKJU-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxy-2,6-dimethylphenyl]thiourea Chemical compound C=1C(C)=C(NC(=S)NC=2C=CC(Cl)=CC=2)C(C)=CC=1OC(C=C1N2C)=CC=C1N=C2COC(C=C1)=CC=C1CC1SC(=O)NC1=O UAGOWIAHMMDKJU-UHFFFAOYSA-N 0.000 claims 1
- VYCJDFFYLPUNEO-UHFFFAOYSA-N 1-[3-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound N=1C2=CC=C(OC=3C=C(NC(=O)NC=4C(=CC=CC=4)C(F)(F)F)C=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O VYCJDFFYLPUNEO-UHFFFAOYSA-N 0.000 claims 1
- ISBCTBWYSJLJPG-UHFFFAOYSA-N 1-[3-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]-3-phenylurea Chemical compound N=1C2=CC=C(OC=3C=C(NC(=O)NC=4C=CC=CC=4)C=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O ISBCTBWYSJLJPG-UHFFFAOYSA-N 0.000 claims 1
- VGUZMYODIGQFGA-UHFFFAOYSA-N 1-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxy-2,6-dimethylphenyl]-3-(4-nitrophenyl)urea Chemical compound C=1C(C)=C(NC(=O)NC=2C=CC(=CC=2)[N+]([O-])=O)C(C)=CC=1OC(C=C1N2C)=CC=C1N=C2COC(C=C1)=CC=C1CC1SC(=O)NC1=O VGUZMYODIGQFGA-UHFFFAOYSA-N 0.000 claims 1
- SRLJUIPXCNUBDG-UHFFFAOYSA-N 1-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]-3-phenylurea Chemical compound N=1C2=CC=C(OC=3C=CC(NC(=O)NC=4C=CC=CC=4)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O SRLJUIPXCNUBDG-UHFFFAOYSA-N 0.000 claims 1
- GQUAFKLVDHDXBQ-UHFFFAOYSA-N 1-[7-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxynaphthalen-1-yl]-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NC(C1=C2)=CC=CC1=CC=C2OC1=CC=C(N=C(COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)N2C)C2=C1 GQUAFKLVDHDXBQ-UHFFFAOYSA-N 0.000 claims 1
- IXTLJGIFZCZPHO-UHFFFAOYSA-N 1-benzyl-3-[7-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxynaphthalen-1-yl]thiourea Chemical compound N=1C2=CC=C(OC=3C=C4C(NC(=S)NCC=5C=CC=CC=5)=CC=CC4=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O IXTLJGIFZCZPHO-UHFFFAOYSA-N 0.000 claims 1
- DEHUXKDDQUKRAW-UHFFFAOYSA-N 3-chloro-n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]benzamide Chemical compound N=1C2=CC=C(OC=3C=CC(NC(=O)C=4C=C(Cl)C=CC=4)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O DEHUXKDDQUKRAW-UHFFFAOYSA-N 0.000 claims 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- KFSJPZZPCJEMBY-UHFFFAOYSA-N n-[2-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]ethyl]pyridine-3-carboxamide Chemical compound N=1C2=CC=C(OC=3C=CC(CCNC(=O)C=4C=NC=CC=4)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O KFSJPZZPCJEMBY-UHFFFAOYSA-N 0.000 claims 1
- ZANZLUPRQFRTPW-UHFFFAOYSA-N n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]-n-hexylacetamide Chemical compound C1=CC(N(C(C)=O)CCCCCC)=CC=C1OC1=CC=C(N=C(COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)N2C)C2=C1 ZANZLUPRQFRTPW-UHFFFAOYSA-N 0.000 claims 1
- ZKHLYSRUNNGEBM-UHFFFAOYSA-N n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]benzamide Chemical compound N=1C2=CC=C(OC=3C=CC(NC(=O)C=4C=CC=CC=4)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O ZKHLYSRUNNGEBM-UHFFFAOYSA-N 0.000 claims 1
- CVRCPCWIPMRMCY-UHFFFAOYSA-N n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]cyclopentanecarboxamide Chemical compound N=1C2=CC=C(OC=3C=CC(NC(=O)C4CCCC4)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O CVRCPCWIPMRMCY-UHFFFAOYSA-N 0.000 claims 1
- LUZIKZKELDJVJM-UHFFFAOYSA-N n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]pyridine-4-carboxamide Chemical compound N=1C2=CC=C(OC=3C=CC(NC(=O)C=4C=CN=CC=4)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O LUZIKZKELDJVJM-UHFFFAOYSA-N 0.000 claims 1
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 description 18
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 2
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 2
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
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- 125000005917 3-methylpentyl group Chemical group 0.000 description 2
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- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Liquid Crystal Substances (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| JP9998199 | 1999-04-07 |
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| WO (1) | WO2000061581A1 (cs) |
| ZA (1) | ZA200108174B (cs) |
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| WO2003033494A1 (en) * | 2001-10-17 | 2003-04-24 | Sankyo Company, Limited | Benzimidazole derivative |
| WO2003032988A1 (fr) * | 2001-10-17 | 2003-04-24 | Sankyo Company, Limited | Composition pharmaceutique |
| WO2003082865A1 (en) * | 2002-04-01 | 2003-10-09 | Sankyo Company, Limited | Medicinal antitumor composition |
| MXPA04010938A (es) | 2002-05-08 | 2005-02-14 | Bayer Healthcare Ag | Derivados de hidroxi-tetrahidro-naftalenilurea. |
| WO2004000356A1 (ja) * | 2002-06-25 | 2003-12-31 | Sankyo Company, Limited | 利尿剤及びペルオキシソーム増殖因子活性化受容体（PPAR)γ活性化剤を含有する医薬組成物 |
| TW200408628A (en) * | 2002-08-02 | 2004-06-01 | Sankyo Co | Resorcinol and its derivatives |
| US7521465B2 (en) * | 2003-01-17 | 2009-04-21 | Bexel Pharmaceuticals, Inc. | Diphenyl ether derivatives |
| US7781464B2 (en) * | 2003-01-17 | 2010-08-24 | Bexel Pharmaceuticals, Inc. | Heterocyclic diphenyl ethers |
| US20050026844A1 (en) | 2003-04-03 | 2005-02-03 | Regents Of The University Of California | Inhibitors for the soluble epoxide hydrolase |
| US7087576B2 (en) * | 2003-10-07 | 2006-08-08 | Bexel Pharmaceuticals, Inc. | Dipeptide phenyl ethers |
| CA2559665A1 (en) | 2004-03-16 | 2005-09-29 | The Regents Of The University Of California | Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids |
| AU2005295167B2 (en) * | 2004-10-20 | 2012-05-10 | The Regents Of The University Of California | Improved inhibitors for the soluble epoxide hydrolase |
| EP1943226A2 (en) | 2005-10-13 | 2008-07-16 | Smithkline Beecham Corporation | Phenol ethers as modulators of the opioid receptors |
| US20070185055A1 (en) * | 2006-02-06 | 2007-08-09 | Guang Liang Jiang | Method for treating cachexia with retinoid ligands |
| TW200838512A (en) | 2007-02-08 | 2008-10-01 | Daiichi Sankyo Co Ltd | Crystalline forms of a thiazolidinedione compound and manufacturing methods thereof |
| WO2010013769A1 (ja) * | 2008-07-31 | 2010-02-04 | 第一三共株式会社 | チアゾリジンジオン化合物の結晶及びその製造方法 |
| JPWO2010013768A1 (ja) * | 2008-07-31 | 2012-01-12 | 第一三共株式会社 | チアゾリジンジオン化合物の結晶及びその製造方法 |
| US20120238759A1 (en) * | 2009-11-26 | 2012-09-20 | Daiichi Sankyo Company, Limited | Method for manufacturing a 6-substituted 1-methyl-1h-benzimidazole derivative and an intermediate of said method |
| CA2799205A1 (en) | 2010-05-25 | 2011-12-01 | Qiagen Gaithersburg, Inc. | Fast results hybrid capture assay and associated strategically-truncated probes |
| US10077241B2 (en) | 2014-04-15 | 2018-09-18 | Jansen Pharmaceutica Nv | Tetrahydro-benzoimidazolyl modulators of TGR5 |
| KR101480674B1 (ko) * | 2014-07-03 | 2015-01-09 | 주식회사 큐리언트 | 화합물 및 염증성 질환 치료용 약학적 조성물 |
| KR101496094B1 (ko) * | 2014-07-04 | 2015-02-25 | 주식회사 큐리언트 | 화합물 및 염증성 질환 치료용 약학적 조성물 |
| KR101496096B1 (ko) * | 2014-07-17 | 2015-03-02 | 주식회사 큐리언트 | 화합물 및 염증성 질환 치료용 약학적 조성물 |
| WO2018002673A1 (en) | 2016-07-01 | 2018-01-04 | N4 Pharma Uk Limited | Novel formulations of angiotensin ii receptor antagonists |
| US11518739B2 (en) | 2017-08-15 | 2022-12-06 | Inflazome Limited | Sulfonamide carboxamide compounds |
Family Cites Families (18)
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| KR940000623B1 (ko) | 1989-05-15 | 1994-01-26 | 히페리온 카탈리시스 인터내셔날 | 마이크로 탄소섬유 산화처리방법 |
| FR2680512B1 (fr) | 1991-08-20 | 1995-01-20 | Adir | Nouveaux derives de 2,4-thiazolidinedione, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| CZ282548B6 (cs) | 1992-01-22 | 1997-08-13 | F. Hoffmann-La Roche Ag | Farmaceutický přípravek |
| WO1994015901A1 (en) | 1993-01-11 | 1994-07-21 | Ligand Pharmaceuticals Inc. | Compounds having selectivity for retinoid x receptors |
| TW268952B (cs) | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
| WO1994022846A1 (en) * | 1993-03-30 | 1994-10-13 | Pfizer Inc. | Compounds enhancing antitumor activity of other cytotoxic agents |
| JP3300869B2 (ja) | 1993-08-09 | 2002-07-08 | 武田薬品工業株式会社 | ２，４−オキサゾリジンジオン誘導体、その製造法およびそれを含んでなる医薬組成物 |
| RU2114844C1 (ru) * | 1994-04-11 | 1998-07-10 | Санкио Компани Лимитед | Производные тиозолидиндиона или их фармацевтически приемлемые соли, фармацевтическая композиция на их основе и способ лечения или профилактики заболеваний |
| CA2159938A1 (en) * | 1994-10-07 | 1996-04-08 | Hiroaki Yanagisawa | Oxime derivatives, their preparation and their therapeutic use |
| TW403748B (en) * | 1994-11-02 | 2000-09-01 | Takeda Chemical Industries Ltd | An oxazolidinedione derivative, its production and a pharmaceutical composition for lowering blood sugar and lipid in blood comprising the same |
| WO1996020913A1 (en) | 1994-12-30 | 1996-07-11 | Ligand Pharmaceuticals Incorporated | Novel trienoic retinoid compounds and methods |
| CZ293016B6 (cs) | 1995-06-01 | 2004-01-14 | Sankyo Company Limited | Benzimidazolové deriváty a farmaceutické prostředky s jejich obsahem |
| JPH09165371A (ja) * | 1995-10-09 | 1997-06-24 | Sankyo Co Ltd | 複素環化合物を含有する医薬 |
| BR9711098B1 (pt) | 1996-07-01 | 2011-10-04 | compostos heterocìclicos, processo para sua preparação e composições farmacêuticas contendo os mesmos e seu uso no tratamento de diabetes e doenças relacionadas. | |
| JP3268242B2 (ja) | 1996-11-14 | 2002-03-25 | 三共株式会社 | 縮合複素環化合物を含有する医薬 |
| EP1005344A4 (en) | 1996-12-31 | 2003-03-19 | Salk Inst For Biological Studi | TREATMENT OF LIPOSARCOMES USING A COMBINATION OF THIAZOLIDINEDIONES AND SELECTIVE AGONISTS OF RETINO X RECEPTORS |
| RU2111002C1 (ru) * | 1997-07-02 | 1998-05-20 | Зволинский Юрий Антонович | Средство зволинского, обладающее иммунотропной, ранозаживляющей и антимикробной активностью и способ его получения |
| DE69824194T2 (de) * | 1997-10-08 | 2005-01-13 | Sankyo Co., Ltd. | Substituierte kondensierte heterocyclische verbindungen |
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2000
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