IL127219A - Use of insulin sensitivity enhancers to create drugs for the treatment of hyperuricemia and preparations containing insulin sensitivity enhancers for the treatment of oral - Google Patents
Use of insulin sensitivity enhancers to create drugs for the treatment of hyperuricemia and preparations containing insulin sensitivity enhancers for the treatment of oralInfo
- Publication number
- IL127219A IL127219A IL12721998A IL12721998A IL127219A IL 127219 A IL127219 A IL 127219A IL 12721998 A IL12721998 A IL 12721998A IL 12721998 A IL12721998 A IL 12721998A IL 127219 A IL127219 A IL 127219A
- Authority
- IL
- Israel
- Prior art keywords
- group
- carbon atoms
- benzyl
- dione
- thiazolidine
- Prior art date
Links
- 206010022489 Insulin Resistance Diseases 0.000 title claims abstract description 39
- 239000003623 enhancer Substances 0.000 title claims abstract description 37
- 201000001431 Hyperuricemia Diseases 0.000 title claims abstract description 28
- 238000011282 treatment Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 239000003814 drug Substances 0.000 title claims abstract description 11
- 239000000203 mixture Substances 0.000 title claims description 33
- 230000002265 prevention Effects 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 567
- 125000001424 substituent group Chemical group 0.000 claims description 367
- -1 phenylacetyl group Chemical group 0.000 claims description 366
- 150000001875 compounds Chemical class 0.000 claims description 217
- 125000000217 alkyl group Chemical group 0.000 claims description 187
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 134
- 125000003545 alkoxy group Chemical group 0.000 claims description 91
- 125000003118 aryl group Chemical group 0.000 claims description 81
- 125000005843 halogen group Chemical group 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
- 125000002252 acyl group Chemical group 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 40
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 38
- 125000003277 amino group Chemical group 0.000 claims description 36
- 125000004434 sulfur atom Chemical group 0.000 claims description 36
- 125000004414 alkyl thio group Chemical group 0.000 claims description 35
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 35
- 125000004076 pyridyl group Chemical group 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 125000001931 aliphatic group Chemical group 0.000 claims description 27
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 26
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 20
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 18
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 17
- 125000004423 acyloxy group Chemical group 0.000 claims description 17
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
- XMSXOLDPMGMWTH-UHFFFAOYSA-N rivoglitazone Chemical compound CN1C2=CC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O XMSXOLDPMGMWTH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 6
- MJAMNJNCEOHYIU-UHFFFAOYSA-N 1,2-oxazolidine-3,4-dione Chemical class O=C1CONC1=O MJAMNJNCEOHYIU-UHFFFAOYSA-N 0.000 claims description 5
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical group C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 5
- JJWGHBNCPOMGIA-UHFFFAOYSA-N 5-[[4-[(1-methyl-2,3-dihydroindol-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1C2=CC=CC=C2N(C)C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O JJWGHBNCPOMGIA-UHFFFAOYSA-N 0.000 claims description 5
- OVGVKTHROKSCRJ-UHFFFAOYSA-N 5-[[4-[(1-methylbenzimidazol-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O OVGVKTHROKSCRJ-UHFFFAOYSA-N 0.000 claims description 5
- VPFJHPSVNYPBHL-UHFFFAOYSA-N 5-[[4-[(5-methoxy-3-methylimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN1C2=NC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O VPFJHPSVNYPBHL-UHFFFAOYSA-N 0.000 claims description 5
- TUWVRIRVQCCGDG-UHFFFAOYSA-N [2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl] ethyl carbonate Chemical compound C1CC2=C(C)C(OC(=O)OCC)=C(C)C(C)=C2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O TUWVRIRVQCCGDG-UHFFFAOYSA-N 0.000 claims description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 5
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 5
- QQKNSPHAFATFNQ-UHFFFAOYSA-N darglitazone Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCC(=O)C(C=C1)=CC=C1CC1SC(=O)NC1=O QQKNSPHAFATFNQ-UHFFFAOYSA-N 0.000 claims description 5
- MVDXXGIBARMXSA-UHFFFAOYSA-N englitazone Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(OC(CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 5
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 claims description 5
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 4
- QBQLYIISSRXYKL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O QBQLYIISSRXYKL-UHFFFAOYSA-N 0.000 claims description 4
- PECKLIXQHBFLKD-UHFFFAOYSA-N 4-amino-5h-1,3-thiazol-2-one Chemical class NC1=NC(=O)SC1 PECKLIXQHBFLKD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001475 oxazolidinediones Chemical class 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 3
- WOPRKZJPZYBOGL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylidene]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1C=C1C(=O)NOC1=O WOPRKZJPZYBOGL-UHFFFAOYSA-N 0.000 claims description 3
- ONODKHPBKXXABX-UHFFFAOYSA-N 5-[[4-[(1-benzylbenzimidazol-5-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC(C=C1)=CC=C1OCC1=CC=C(N(CC=2C=CC=CC=2)C=N2)C2=C1 ONODKHPBKXXABX-UHFFFAOYSA-N 0.000 claims description 3
- WEEPXEIATGBQQK-UHFFFAOYSA-N 5-[[4-[(3-methyl-5-oxo-4h-imidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(O)N=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O WEEPXEIATGBQQK-UHFFFAOYSA-N 0.000 claims description 3
- NYZCYOCLLSTCPQ-UHFFFAOYSA-N 5-[[4-[(3-methyl-5-propan-2-yloxyimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN1C2=NC(OC(C)C)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O NYZCYOCLLSTCPQ-UHFFFAOYSA-N 0.000 claims description 3
- VJRCELWLZGOZTR-UHFFFAOYSA-N 5-[[4-[(3-methylimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CN=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O VJRCELWLZGOZTR-UHFFFAOYSA-N 0.000 claims description 3
- BHNIQYLHLZTUAN-UHFFFAOYSA-N 5-[[4-[(5-ethoxy-3-methylimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN1C2=NC(OCC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O BHNIQYLHLZTUAN-UHFFFAOYSA-N 0.000 claims description 3
- DVSRBVOYQJNPBO-UHFFFAOYSA-N 5-[[4-[(5-methoxy-1-methylbenzimidazol-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC(OC)=CC=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O DVSRBVOYQJNPBO-UHFFFAOYSA-N 0.000 claims description 3
- KMCXNGXUURGATQ-UHFFFAOYSA-N 5-[[4-[(7-tert-butyl-6-hydroxy-2-methyl-3,4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1CC=2C=C(O)C(C(C)(C)C)=CC=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O KMCXNGXUURGATQ-UHFFFAOYSA-N 0.000 claims description 3
- XXXJVWWTTPKLAI-UHFFFAOYSA-N 5-[[4-[2-(3-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CCC1=CC=CN=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 XXXJVWWTTPKLAI-UHFFFAOYSA-N 0.000 claims description 3
- KHPNZOZOQKIDBF-UHFFFAOYSA-N 5-[[4-[2-(4-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CCC1=CC=NC(CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 KHPNZOZOQKIDBF-UHFFFAOYSA-N 0.000 claims description 3
- KKCUXBKPORBJFG-UHFFFAOYSA-N 5-[[4-[2-(6-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CCC1=CC=CC(CCOC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=N1 KKCUXBKPORBJFG-UHFFFAOYSA-N 0.000 claims description 3
- BZYJVHSYHURRND-UHFFFAOYSA-N 5-[[4-[2-(pyrimidin-2-ylamino)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC(C=C1)=CC=C1OCCNC1=NC=CC=N1 BZYJVHSYHURRND-UHFFFAOYSA-N 0.000 claims description 3
- HLZUFJJOZAUDTE-UHFFFAOYSA-N 5-[[4-[2-[(4,5-dimethyl-1,3-oxazol-2-yl)-methylamino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C(C)=C(C)OC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O HLZUFJJOZAUDTE-UHFFFAOYSA-N 0.000 claims description 3
- NACAADVHQHZGOW-UHFFFAOYSA-N 5-[[4-[2-[methyl(1,3-thiazol-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C=CSC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O NACAADVHQHZGOW-UHFFFAOYSA-N 0.000 claims description 3
- IGJSREGKAKOCGJ-UHFFFAOYSA-N 5-[[4-[2-[methyl-(5-methyl-4-phenyl-1,3-thiazol-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C(C=2C=CC=CC=2)=C(C)SC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O IGJSREGKAKOCGJ-UHFFFAOYSA-N 0.000 claims description 3
- LJGONHLWDITULH-UHFFFAOYSA-N 5-[[4-[2-[methyl-(5-phenyl-1,3-oxazol-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C=C(C=2C=CC=CC=2)OC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O LJGONHLWDITULH-UHFFFAOYSA-N 0.000 claims description 3
- DWPTVWXVZBYAIW-UHFFFAOYSA-N 5-[[4-[3-[1,3-benzoxazol-2-yl(methyl)amino]propoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=CC=C2OC=1N(C)CCCOC(C=C1)=CC=C1CC1SC(=O)NC1=O DWPTVWXVZBYAIW-UHFFFAOYSA-N 0.000 claims description 3
- HIKRPVCYHOKTNQ-UHFFFAOYSA-N 5-[[4-[[6-hydroxy-5,7,8-trimethyl-2-(2-methylpropyl)-3,4-dihydrochromen-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1CC2=C(C)C(O)=C(C)C(C)=C2OC1(CC(C)C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O HIKRPVCYHOKTNQ-UHFFFAOYSA-N 0.000 claims description 3
- WBOOERRGGVUMFH-UHFFFAOYSA-N [2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl] acetate Chemical compound C1CC2=C(C)C(OC(=O)C)=C(C)C(C)=C2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O WBOOERRGGVUMFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 3
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
- VBYNVJUPQIUGCH-UHFFFAOYSA-N n-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]-n-pyrimidin-2-ylacetamide Chemical compound N=1C=CC=NC=1N(C(=O)C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O VBYNVJUPQIUGCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- UOJKSDOVAWFEHK-UHFFFAOYSA-N triazol-4-imine Chemical class N=C1C=NN=N1 UOJKSDOVAWFEHK-UHFFFAOYSA-N 0.000 claims description 3
- QDKGOMZIPXGDDJ-UHFFFAOYSA-N 2,3-dihydro-1h-indazole Chemical group C1=CC=C2CNNC2=C1 QDKGOMZIPXGDDJ-UHFFFAOYSA-N 0.000 claims description 2
- AFBCBLCTKUVCFC-UHFFFAOYSA-N 4-[[4-[2-[2-(1-benzothiophen-2-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2SC3=CC=CC=C3C=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O AFBCBLCTKUVCFC-UHFFFAOYSA-N 0.000 claims description 2
- DTWCLKZUSOJSOU-UHFFFAOYSA-N 5-[(2-benzyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(OC(CC=2C=CC=CC=2)C2)C2=C1 DTWCLKZUSOJSOU-UHFFFAOYSA-N 0.000 claims description 2
- RGQNYGHRASYZHL-UHFFFAOYSA-N 5-[[4-[(5-chloro-3-methylimidazo[4,5-b]pyridin-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(Cl)N=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O RGQNYGHRASYZHL-UHFFFAOYSA-N 0.000 claims description 2
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
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- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Biological Depolymerization Polymers (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32318297 | 1997-11-25 |
Publications (2)
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| IL127219A0 IL127219A0 (en) | 1999-09-22 |
| IL127219A true IL127219A (en) | 2001-08-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| IL12721998A IL127219A (en) | 1997-11-25 | 1998-11-23 | Use of insulin sensitivity enhancers to create drugs for the treatment of hyperuricemia and preparations containing insulin sensitivity enhancers for the treatment of oral |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6353009B1 (de) |
| EP (1) | EP0919232B1 (de) |
| KR (1) | KR19990045531A (de) |
| AR (1) | AR011231A1 (de) |
| AT (1) | ATE278400T1 (de) |
| AU (1) | AU744653B2 (de) |
| BR (1) | BR9805012A (de) |
| CA (1) | CA2254394C (de) |
| CZ (1) | CZ378898A3 (de) |
| DE (2) | DE69826811T4 (de) |
| ES (1) | ES2230657T3 (de) |
| HU (2) | HUP9902721A2 (de) |
| ID (1) | ID21332A (de) |
| IL (1) | IL127219A (de) |
| NO (1) | NO985484L (de) |
| NZ (1) | NZ332895A (de) |
| PL (1) | PL329893A1 (de) |
| RU (1) | RU2190425C2 (de) |
| SA (1) | SA99191266A (de) |
| TR (1) | TR199802441A2 (de) |
| TW (1) | TW592697B (de) |
| ZA (1) | ZA9810788B (de) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7045519B2 (en) | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| WO1999065897A1 (en) | 1998-06-19 | 1999-12-23 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| EP1180686B1 (de) * | 1999-05-27 | 2009-10-14 | CMIC Co., Ltd. | Heilmittel für nierenkrankheiten und verfahren zum screenen selbiger |
| US6768008B2 (en) | 2000-04-24 | 2004-07-27 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
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- 1998-11-18 US US09/195,031 patent/US6353009B1/en not_active Expired - Fee Related
- 1998-11-18 DE DE69826811T patent/DE69826811T4/de not_active Expired - Lifetime
- 1998-11-18 EP EP98309426A patent/EP0919232B1/de not_active Expired - Lifetime
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- 1998-11-19 NZ NZ332895A patent/NZ332895A/en unknown
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- 1998-11-23 IL IL12721998A patent/IL127219A/en not_active IP Right Cessation
- 1998-11-24 KR KR1019980050484A patent/KR19990045531A/ko not_active Ceased
- 1998-11-24 TW TW087119452A patent/TW592697B/zh not_active IP Right Cessation
- 1998-11-24 BR BR9805012A patent/BR9805012A/pt not_active Application Discontinuation
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- 1998-11-25 ZA ZA9810788A patent/ZA9810788B/xx unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| SA99191266A (ar) | 2005-12-03 |
| ZA9810788B (en) | 1999-05-25 |
| DE69826811T2 (de) | 2005-06-16 |
| US6353009B1 (en) | 2002-03-05 |
| NO985484L (no) | 1999-05-26 |
| HU9802721D0 (en) | 1999-01-28 |
| EP0919232B1 (de) | 2004-10-06 |
| KR19990045531A (ko) | 1999-06-25 |
| TR199802441A3 (tr) | 1999-10-21 |
| PL329893A1 (en) | 1999-06-07 |
| IL127219A0 (en) | 1999-09-22 |
| AU744653B2 (en) | 2002-02-28 |
| NO985484D0 (no) | 1998-11-24 |
| BR9805012A (pt) | 2000-03-21 |
| CZ378898A3 (cs) | 1999-07-14 |
| HUP9802721A1 (hu) | 2000-03-28 |
| ID21332A (id) | 1999-05-27 |
| DE69826811T4 (de) | 2006-09-21 |
| ES2230657T3 (es) | 2005-05-01 |
| ATE278400T1 (de) | 2004-10-15 |
| EP0919232A1 (de) | 1999-06-02 |
| CA2254394A1 (en) | 1999-05-25 |
| HK1020259A1 (en) | 2000-04-07 |
| TW592697B (en) | 2004-06-21 |
| AU9410298A (en) | 1999-06-17 |
| NZ332895A (en) | 2001-04-27 |
| TR199802441A2 (xx) | 1999-10-21 |
| HUP9902721A2 (hu) | 1999-12-28 |
| RU2190425C2 (ru) | 2002-10-10 |
| AR011231A1 (es) | 2000-08-02 |
| CA2254394C (en) | 2009-11-17 |
| DE69826811D1 (de) | 2004-11-11 |
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