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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- A—HUMAN NECESSITIES
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- 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
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- 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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- 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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| Application Number | Priority Date | Filing Date | Title |
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| JP9998199 | 1999-04-07 |
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| ZA200108174B true ZA200108174B (en) | 2003-01-06 |
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| WO (1) | WO2000061581A1 (cs) |
| ZA (1) | ZA200108174B (cs) |
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| WO2003032988A1 (fr) * | 2001-10-17 | 2003-04-24 | Sankyo Company, Limited | Composition pharmaceutique |
| WO2003033494A1 (fr) * | 2001-10-17 | 2003-04-24 | Sankyo Company, Limited | Derive de benzimidazole |
| AU2003220855A1 (en) * | 2002-04-01 | 2003-10-13 | Sankyo Company, Limited | Medicinal antitumor composition |
| NZ536418A (en) | 2002-05-08 | 2006-04-28 | Bayer Healthcare Ag | Hydroxy tetrahydro-naphthalenylurea derivatives having vanilloid receptor (VR) antagonistic activity |
| TW200403055A (en) * | 2002-06-25 | 2004-03-01 | Sankyo Co | Pharmaceutical composition of a peroxisome proliferator-activated receptor (PPAR) gamma atcivetor and a diuretic |
| AU2003254795A1 (en) * | 2002-08-02 | 2004-02-23 | Sankyo Company, Limited | Resorcinol derivative |
| 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 |
| CA2520763A1 (en) | 2003-04-03 | 2004-10-21 | The Regents Of The University Of California | Improved inhibitors for the soluble epoxide hydrolase |
| US7087576B2 (en) * | 2003-10-07 | 2006-08-08 | Bexel Pharmaceuticals, Inc. | Dipeptide phenyl ethers |
| JP2007532484A (ja) | 2004-03-16 | 2007-11-15 | ザ・レジェンツ・オブ・ザ・ユニバーシティ・オブ・カリフォルニア | 可溶性エポキシド加水分解酵素の阻害剤およびエポキシエイコサノイドを用いて腎症を緩和する方法 |
| ZA200703613B (en) * | 2004-10-20 | 2009-05-27 | Univ California | Improved inhibitors for the soluble epoxide hydrolase |
| US7939528B2 (en) | 2005-10-13 | 2011-05-10 | Glaxosmithkline Llc | Heterocycle compounds |
| US20070185055A1 (en) * | 2006-02-06 | 2007-08-09 | Guang Liang Jiang | Method for treating cachexia with retinoid ligands |
| TW201336497A (zh) | 2007-02-08 | 2013-09-16 | Daiichi Sankyo Co Ltd | 噻唑啶二酮化合物之結晶型及其製法 |
| 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 |
| US20110124692A1 (en) * | 2008-07-31 | 2011-05-26 | Daiichi Sankyo Company, Limited | Crystalline forms of thiazolidinedione compound and its manufacturing method |
| WO2011065420A1 (ja) | 2009-11-26 | 2011-06-03 | 第一三共株式会社 | ６－置換－１－メチル－１ｈ－ベンズイミダゾール誘導体の製造法及びその製造中間体 |
| JP6153866B2 (ja) | 2010-05-25 | 2017-06-28 | キアゲン ガイサーズバーグ アイエヌシー． | 迅速なハイブリッド捕捉アッセイ、及び関連する戦略的に切断されたプローブ |
| WO2015160772A1 (en) * | 2014-04-15 | 2015-10-22 | Janssen 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 |
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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 |
| CZ289317B6 (cs) | 1994-04-11 | 2002-01-16 | Sankyo Company Limited | Heterocyklická sloučenina, farmaceutický prostředek ji obsahující a její pouľití |
| CZ261095A3 (en) * | 1994-10-07 | 1996-04-17 | Sankyo Co | Oxime derivatives, process of their preparation, pharmaceutical composition containing thereof and their 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 |
| ES2148593T3 (es) | 1994-12-30 | 2000-10-16 | Ligand Pharm Inc | Compuestos retinoides trienoicos novedosos y metodos. |
| IL118474A (en) * | 1995-06-01 | 2001-08-08 | Sankyo Co | Benzimideol derivatives and pharmaceutical preparations containing them |
| JPH09165371A (ja) * | 1995-10-09 | 1997-06-24 | Sankyo Co Ltd | 複素環化合物を含有する医薬 |
| CA2258949C (en) | 1996-07-01 | 2008-05-06 | Dr. Reddy's Research Foundation | Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| 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 |
| BR9813848B1 (pt) * | 1997-10-08 | 2011-07-12 | composto heterocìclico fundido substituìdo, uso do mesmo, e, composição farmacêutica. |
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