NO321158B1 - Aminderivatforbindelser, farmasoytiske preparater som omfatter forbindelsene, samt anvendelse av forbindelsene til fremstilling av farmasoytiske preparater. - Google Patents
Aminderivatforbindelser, farmasoytiske preparater som omfatter forbindelsene, samt anvendelse av forbindelsene til fremstilling av farmasoytiske preparater. Download PDFInfo
- Publication number
- NO321158B1 NO321158B1 NO20014847A NO20014847A NO321158B1 NO 321158 B1 NO321158 B1 NO 321158B1 NO 20014847 A NO20014847 A NO 20014847A NO 20014847 A NO20014847 A NO 20014847A NO 321158 B1 NO321158 B1 NO 321158B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- methyl
- phenyl
- benzimidazol
- ylmethyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 459
- 150000001412 amines Chemical class 0.000 title claims abstract description 88
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title 2
- 150000003839 salts Chemical class 0.000 claims abstract description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 37
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 18
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 16
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 7
- 201000011510 cancer Diseases 0.000 claims abstract description 7
- -1 thiocarbamoyl group Chemical group 0.000 claims description 308
- 125000001424 substituent group Chemical group 0.000 claims description 151
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 22
- 239000008280 blood Substances 0.000 claims description 20
- 210000004369 blood Anatomy 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 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 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
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- 206010012655 Diabetic complications Diseases 0.000 claims description 6
- 102000004877 Insulin Human genes 0.000 claims description 6
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- 239000012190 activator Substances 0.000 claims description 6
- 229940125396 insulin Drugs 0.000 claims description 6
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 6
- UJDBFVLGTQSOCO-UHFFFAOYSA-N n-[4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxyphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OC1=CC=C(N=C(COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)N2C)C2=C1 UJDBFVLGTQSOCO-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 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 description 5
- 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 description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 208000004104 gestational diabetes Diseases 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 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 description 5
- 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 description 5
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- LMQQURUJYOTXBB-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]methyl]urea Chemical compound N=1C2=CC=C(OC=3C=C(NC(=O)NCC=4C=CC(=CC=4)C(F)(F)F)C=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O LMQQURUJYOTXBB-UHFFFAOYSA-N 0.000 claims description 3
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- WGXPLHFBVWEUIO-UHFFFAOYSA-N tert-butyl 2-[5-[8-[(2-methylpropan-2-yl)oxycarbonylamino]naphthalen-2-yl]oxy-2-nitroanilino]acetate Chemical compound C1=C([N+]([O-])=O)C(NCC(=O)OC(C)(C)C)=CC(OC=2C=C3C(NC(=O)OC(C)(C)C)=CC=CC3=CC=2)=C1 WGXPLHFBVWEUIO-UHFFFAOYSA-N 0.000 description 1
- MMQQREWJSHCZDB-UHFFFAOYSA-N tert-butyl 5-[2-[4-amino-3-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]phenoxy]anilino]-2-ethylpentanoate Chemical compound CC(C)(C)OC(=O)C(CC)CCCNC1=CC=CC=C1OC1=CC=C(N)C(N(C)C(=O)OC(C)(C)C)=C1 MMQQREWJSHCZDB-UHFFFAOYSA-N 0.000 description 1
- HJQNVUQTARSZDK-UHFFFAOYSA-N tert-butyl n-(3-hydroxyphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(O)=C1 HJQNVUQTARSZDK-UHFFFAOYSA-N 0.000 description 1
- YRQMBQUMJFVZLF-UHFFFAOYSA-N tert-butyl n-(4-hydroxyphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(O)C=C1 YRQMBQUMJFVZLF-UHFFFAOYSA-N 0.000 description 1
- FHSROIHASLRHAO-UHFFFAOYSA-N tert-butyl n-[2-[[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetyl]amino]-5-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethoxy]phenyl]-n-methylcarbamate Chemical compound C=1C=C(NC(=O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)C(N(C(=O)OC(C)(C)C)C)=CC=1OCCC1=CC=C(NC(=O)OC(C)(C)C)C=C1 FHSROIHASLRHAO-UHFFFAOYSA-N 0.000 description 1
- LVFMABYVDYTRBA-UHFFFAOYSA-N tert-butyl n-[2-[[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetyl]amino]-5-[3-[(2-methylpropan-2-yl)oxycarbonylamino]phenoxy]phenyl]-n-methylcarbamate Chemical compound C=1C=C(NC(=O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)C(N(C(=O)OC(C)(C)C)C)=CC=1OC1=CC=CC(NC(=O)OC(C)(C)C)=C1 LVFMABYVDYTRBA-UHFFFAOYSA-N 0.000 description 1
- JKRICNBNCTZBTI-UHFFFAOYSA-N tert-butyl n-[2-[[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetyl]amino]-5-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenoxy]phenyl]-n-methylcarbamate Chemical compound C=1C=C(NC(=O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)C(N(C(=O)OC(C)(C)C)C)=CC=1OC1=CC=C(NC(=O)OC(C)(C)C)C=C1 JKRICNBNCTZBTI-UHFFFAOYSA-N 0.000 description 1
- INAMBHIVKROHMW-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[3-[(2-methylpropan-2-yl)oxycarbonylamino]phenoxy]phenyl]-n-methylcarbamate Chemical compound C1=C(N)C(N(C(=O)OC(C)(C)C)C)=CC(OC=2C=C(NC(=O)OC(C)(C)C)C=CC=2)=C1 INAMBHIVKROHMW-UHFFFAOYSA-N 0.000 description 1
- JCZQBLWLUIAZOW-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]phenoxy]phenyl]-n-methylcarbamate Chemical compound C1=C(N)C(N(C(=O)OC(C)(C)C)C)=CC(OC=2C=CC(CCNC(=O)OC(C)(C)C)=CC=2)=C1 JCZQBLWLUIAZOW-UHFFFAOYSA-N 0.000 description 1
- SAGHYKJVBAVRIM-UHFFFAOYSA-N tert-butyl n-[2-amino-5-[4-[hexyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]phenoxy]phenyl]-n-methylcarbamate Chemical compound C1=CC(N(C(=O)OC(C)(C)C)CCCCCC)=CC=C1OC1=CC=C(N)C(N(C)C(=O)OC(C)(C)C)=C1 SAGHYKJVBAVRIM-UHFFFAOYSA-N 0.000 description 1
- FUSCBLVDQPJOHQ-UHFFFAOYSA-N tert-butyl n-[5-[3,5-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]phenoxy]-2-[[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetyl]amino]phenyl]-n-methylcarbamate Chemical compound C=1C=C(NC(=O)COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)C(N(C(=O)OC(C)(C)C)C)=CC=1OC1=CC(C)=C(NC(=O)OC(C)(C)C)C(C)=C1 FUSCBLVDQPJOHQ-UHFFFAOYSA-N 0.000 description 1
- BSZLPZBXXVYPQC-UHFFFAOYSA-N tert-butyl n-[5-[3,5-dimethyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]phenoxy]-2-nitrophenyl]-n-methylcarbamate Chemical compound C1=C([N+]([O-])=O)C(N(C(=O)OC(C)(C)C)C)=CC(OC=2C=C(C)C(NC(=O)OC(C)(C)C)=C(C)C=2)=C1 BSZLPZBXXVYPQC-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- JOQGJRQKCIJIDB-UHFFFAOYSA-N tin;hydrochloride Chemical compound Cl.[Sn] JOQGJRQKCIJIDB-UHFFFAOYSA-N 0.000 description 1
- BVZHHYGKLICOLC-UHFFFAOYSA-N trichloro-$l^{3}-bromane Chemical compound ClBr(Cl)Cl BVZHHYGKLICOLC-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
-
- 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
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrrole Compounds (AREA)
- Liquid Crystal Substances (AREA)
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JP9998199 | 1999-04-07 | ||
PCT/JP2000/002216 WO2000061581A1 (en) | 1999-04-07 | 2000-04-06 | Amine derivatives |
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EP (1) | EP1167366B1 (zh) |
KR (1) | KR100588284B1 (zh) |
CN (1) | CN1162427C (zh) |
AT (1) | ATE466861T1 (zh) |
AU (1) | AU757729B2 (zh) |
BR (1) | BR0009594A (zh) |
CA (1) | CA2369971A1 (zh) |
CZ (1) | CZ300691B6 (zh) |
DE (1) | DE60044342D1 (zh) |
ES (1) | ES2343104T3 (zh) |
HK (1) | HK1039940B (zh) |
HU (1) | HUP0200996A3 (zh) |
ID (1) | ID30498A (zh) |
IL (2) | IL145759A0 (zh) |
MX (1) | MXPA01010108A (zh) |
NO (1) | NO321158B1 (zh) |
NZ (1) | NZ514662A (zh) |
PL (1) | PL351878A1 (zh) |
RU (1) | RU2221796C2 (zh) |
TR (1) | TR200103183T2 (zh) |
TW (1) | TW550264B (zh) |
WO (1) | WO2000061581A1 (zh) |
ZA (1) | ZA200108174B (zh) |
Families Citing this family (25)
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WO2003033494A1 (fr) * | 2001-10-17 | 2003-04-24 | Sankyo Company, Limited | Derive de benzimidazole |
WO2003032988A1 (fr) * | 2001-10-17 | 2003-04-24 | Sankyo Company, Limited | Composition pharmaceutique |
WO2003082865A1 (fr) * | 2002-04-01 | 2003-10-09 | Sankyo Company, Limited | Composition médicinale antitumorale |
BR0309940A (pt) | 2002-05-08 | 2005-02-09 | Bayer Healthcare Ag | Derivados de hidróxi-tetraidro-naftaleniluréia |
AU2003246187A1 (en) * | 2002-06-25 | 2004-01-06 | Sankyo Company, Limited | MEDICINAL COMPOSITION CONTAINING DIURETIC AND PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR (PPAR) Gamma ACTIAVTOR |
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 |
EP1608319A4 (en) | 2003-04-03 | 2007-02-28 | Univ California | IMPROVED HEMMER FOR SOLUBLE EPOXY 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 |
CA2584342C (en) * | 2004-10-20 | 2013-04-30 | The Regents Of The University Of California | Improved inhibitors for the soluble epoxide hydrolase |
WO2007047397A2 (en) * | 2005-10-13 | 2007-04-26 | 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 |
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 |
US20110160462A1 (en) * | 2008-07-31 | 2011-06-30 | Daiichi Sankyo Company, Limited | Crystalline forms of thiazolidinedione compound and its manufacturing method |
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 |
KR20120101017A (ko) | 2009-11-26 | 2012-09-12 | 다이이찌 산쿄 가부시키가이샤 | 6-치환 1-메틸-1h-벤즈이미다졸 유도체의 제조법 및 그 제조 중간체 |
US9376727B2 (en) | 2010-05-25 | 2016-06-28 | Qiagen Gaithersburg, Inc. | Fast results hybrid capture assay and associated strategically truncated probes |
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 |
EP3668840A1 (en) * | 2017-08-15 | 2020-06-24 | Inflazome Limited | Novel 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 |
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TW268952B (zh) | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
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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 |
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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 |
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-
2000
- 2000-04-06 NZ NZ514662A patent/NZ514662A/xx unknown
- 2000-04-06 DE DE60044342T patent/DE60044342D1/de not_active Expired - Lifetime
- 2000-04-06 AU AU36708/00A patent/AU757729B2/en not_active Ceased
- 2000-04-06 CZ CZ20013592A patent/CZ300691B6/cs not_active IP Right Cessation
- 2000-04-06 TW TW089106330A patent/TW550264B/zh active
- 2000-04-06 ES ES00915362T patent/ES2343104T3/es not_active Expired - Lifetime
- 2000-04-06 PL PL00351878A patent/PL351878A1/xx not_active Application Discontinuation
- 2000-04-06 WO PCT/JP2000/002216 patent/WO2000061581A1/ja not_active Application Discontinuation
- 2000-04-06 ID IDW00200102147A patent/ID30498A/id unknown
- 2000-04-06 CN CNB008086362A patent/CN1162427C/zh not_active Expired - Fee Related
- 2000-04-06 MX MXPA01010108A patent/MXPA01010108A/es active IP Right Grant
- 2000-04-06 BR BR0009594-0A patent/BR0009594A/pt not_active IP Right Cessation
- 2000-04-06 IL IL14575900A patent/IL145759A0/xx unknown
- 2000-04-06 EP EP00915362A patent/EP1167366B1/en not_active Expired - Lifetime
- 2000-04-06 RU RU2001127082/04A patent/RU2221796C2/ru active
- 2000-04-06 HU HU0200996A patent/HUP0200996A3/hu unknown
- 2000-04-06 AT AT00915362T patent/ATE466861T1/de not_active IP Right Cessation
- 2000-04-06 CA CA002369971A patent/CA2369971A1/en not_active Abandoned
- 2000-04-06 TR TR2001/03183T patent/TR200103183T2/xx unknown
- 2000-04-06 KR KR1020017012728A patent/KR100588284B1/ko not_active IP Right Cessation
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2001
- 2001-10-04 ZA ZA200108174A patent/ZA200108174B/en unknown
- 2001-10-04 IL IL145759A patent/IL145759A/en not_active IP Right Cessation
- 2001-10-05 US US09/971,634 patent/US6562849B1/en not_active Expired - Fee Related
- 2001-10-05 NO NO20014847A patent/NO321158B1/no not_active IP Right Cessation
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2002
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