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 oral

Info

Publication number: IL127219A
Authority: IL; Israel
Prior art keywords: group; carbon atoms; benzyl; dione; thiazolidine
Prior art date: 1997-11-25

Application number

IL12721998A

Other languages

English (en)

Hebrew (he)

Other versions

IL127219A0 (en

Original Assignee

Sankyo Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-11-25

Filing date

1998-11-23

Publication date

2001-08-08

1998-11-23 Application filed by Sankyo Co filed Critical Sankyo Co

1999-09-22 Publication of IL127219A0 publication Critical patent/IL127219A0/xx

2001-08-08 Publication of IL127219A publication Critical patent/IL127219A/en

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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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)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Urology & Nephrology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Immunology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
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)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Biological Depolymerization Polymers (AREA)

IL12721998A 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 IL127219A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP32318297		1997-11-25

Publications (2)

Publication Number	Publication Date
IL127219A0 IL127219A0 (en)	1999-09-22
IL127219A true IL127219A (en)	2001-08-08

Family

ID=18151987

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
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 (tr)
EP (1)	EP0919232B1 (tr)
KR (1)	KR19990045531A (tr)
AR (1)	AR011231A1 (tr)
AT (1)	ATE278400T1 (tr)
AU (1)	AU744653B2 (tr)
BR (1)	BR9805012A (tr)
CA (1)	CA2254394C (tr)
CZ (1)	CZ378898A3 (tr)
DE (2)	DE69826811T4 (tr)
ES (1)	ES2230657T3 (tr)
HU (2)	HUP9902721A2 (tr)
ID (1)	ID21332A (tr)
IL (1)	IL127219A (tr)
NO (1)	NO985484L (tr)
NZ (1)	NZ332895A (tr)
PL (1)	PL329893A1 (tr)
RU (1)	RU2190425C2 (tr)
SA (1)	SA99191266A (tr)
TR (1)	TR199802441A2 (tr)
TW (1)	TW592697B (tr)
ZA (1)	ZA9810788B (tr)

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US6417185B1 (en)	1998-06-19	2002-07-09	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
US7045519B2 (en)	1998-06-19	2006-05-16	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
DK1180686T3 (da) *	1999-05-27	2010-01-04	Cmic Co Ltd	Lægemidler til nyresygdomme og fremgangsmåde til screening deraf
US6784199B2 (en)	2000-09-21	2004-08-31	Aryx Therapeutics	Isoxazolidine compounds useful in the treatment of diabetes, hyperlipidemia, and atherosclerosis in mammals
US6958355B2 (en)	2000-04-24	2005-10-25	Aryx Therapeutics, Inc.	Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
US6680387B2 (en)	2000-04-24	2004-01-20	Aryx Therapeutics	Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
US6768008B2 (en)	2000-04-24	2004-07-27	Aryx Therapeutics	Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
EP1482931B1 (en)	2002-03-05	2011-10-19	TransTech Pharma, Inc.	Mono- and bicyclic azole derivatives that inhibit the interaction of ligands with rage
RU2230565C1 (ru) *	2003-03-31	2004-06-20	Савина Лидия Васильевна	Способ снижения уровня мочевой кислоты в организме человека
CN1805743A (zh) *	2003-05-20	2006-07-19	特兰斯泰克制药公司	用作逆转淀粉样变性及其他与之相关疾病的rage拮抗剂
US20050025823A1 (en) *	2003-07-29	2005-02-03	Fong Andy A.T.	Methods of use of herbal compositions
JP2005092923A (ja) *	2003-09-12	2005-04-07	Renesas Technology Corp	半導体記憶装置
WO2006012438A2 (en)	2004-07-21	2006-02-02	University Of Florida Research Foundation, Inc.	Compositions and methods for treatment and prevention of insulin resistance
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1997
- 1997-03-25 HU HU9902721A patent/HUP9902721A2/hu unknown
1998
- 1998-11-18 ES ES98309426T patent/ES2230657T3/es not_active Expired - Lifetime
- 1998-11-18 AT AT98309426T patent/ATE278400T1/de not_active IP Right Cessation
- 1998-11-18 DE DE69826811T patent/DE69826811T4/de not_active Expired - Lifetime
- 1998-11-18 US US09/195,031 patent/US6353009B1/en not_active Expired - Fee Related
- 1998-11-18 DE DE69826811A patent/DE69826811D1/de not_active Expired - Lifetime
- 1998-11-18 EP EP98309426A patent/EP0919232B1/en not_active Expired - Lifetime
- 1998-11-19 NZ NZ332895A patent/NZ332895A/en unknown
- 1998-11-20 CZ CZ983788A patent/CZ378898A3/cs unknown
- 1998-11-23 IL IL12721998A patent/IL127219A/en not_active IP Right Cessation
- 1998-11-24 NO NO985484A patent/NO985484L/no not_active Application Discontinuation
- 1998-11-24 BR BR9805012A patent/BR9805012A/pt not_active Application Discontinuation
- 1998-11-24 ID IDP981528A patent/ID21332A/id unknown
- 1998-11-24 TW TW087119452A patent/TW592697B/zh not_active IP Right Cessation
- 1998-11-24 CA CA002254394A patent/CA2254394C/en not_active Expired - Fee Related
- 1998-11-24 RU RU98121310/14A patent/RU2190425C2/ru not_active IP Right Cessation
- 1998-11-24 KR KR1019980050484A patent/KR19990045531A/ko not_active Ceased
- 1998-11-25 TR TR1998/02441A patent/TR199802441A2/tr unknown
- 1998-11-25 HU HU9802721A patent/HUP9802721A1/hu unknown
- 1998-11-25 PL PL98329893A patent/PL329893A1/xx unknown
- 1998-11-25 AR ARP980105979A patent/AR011231A1/es unknown
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- 1998-11-25 AU AU94102/98A patent/AU744653B2/en not_active Ceased
1999
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Also Published As

Publication number	Publication date
DE69826811T4 (de)	2006-09-21
ZA9810788B (en)	1999-05-25
IL127219A0 (en)	1999-09-22
BR9805012A (pt)	2000-03-21
SA99191266A (ar)	2005-12-03
HUP9802721A1 (hu)	2000-03-28
RU2190425C2 (ru)	2002-10-10
HU9802721D0 (en)	1999-01-28
ATE278400T1 (de)	2004-10-15
DE69826811D1 (de)	2004-11-11
TW592697B (en)	2004-06-21
TR199802441A3 (tr)	1999-10-21
KR19990045531A (ko)	1999-06-25
US6353009B1 (en)	2002-03-05
AR011231A1 (es)	2000-08-02
CA2254394C (en)	2009-11-17
CA2254394A1 (en)	1999-05-25
EP0919232A1 (en)	1999-06-02
EP0919232B1 (en)	2004-10-06
ID21332A (id)	1999-05-27
DE69826811T2 (de)	2005-06-16
NZ332895A (en)	2001-04-27
TR199802441A2 (tr)	1999-10-21
HUP9902721A2 (hu)	1999-12-28
PL329893A1 (en)	1999-06-07
AU744653B2 (en)	2002-02-28
NO985484L (no)	1999-05-26
AU9410298A (en)	1999-06-17
HK1020259A1 (en)	2000-04-07
NO985484D0 (no)	1998-11-24
ES2230657T3 (es)	2005-05-01
CZ378898A3 (cs)	1999-07-14

Legal Events

Date	Code	Title	Description
2002-02-10	FF	Patent granted
2010-02-14	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
CA2254394C (en)	2009-11-17	Method and composition for the treatment and prevention of hyperuricemia
EP1965783B1 (en)	2013-06-19	Treatment of type 2 diabetes with a combination of dpiv inhibitor and metformin or thiazolidinedione
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KR100680667B1 (ko)	2007-02-09	티아졸리딘디온 및 술포닐우레아를 사용한 당뇨병의 치료
KR20010013845A (ko)	2001-02-26	티아졸리딘디온 및 알파-글루코시다제 억제제를 사용한당뇨병의 치료
UA67743C2 (uk)	2004-07-15	Фармацевтична композиція, що містить тіазолідиндіон і сульфонілсечовину, для лікування діабету
HK1020259B (en)	2005-03-11	Composition for use in the treatment and prevention of hyperuricemia
CA2221241A1 (en)	1997-02-20	A method of reducing the amount of exogenous insulin administered to a patient having noninsulin-dependent diabetes mellitus
JPH11255669A (ja)	1999-09-21	高尿酸血症治療剤
WO1999030739A1 (en)	1999-06-24	Leukemia remedy
JPH11335298A (ja)	1999-12-07	白血病治療剤
WO1997018811A1 (en)	1997-05-29	A method of treating myotonic dystrophy
AU750615B2 (en)	2002-07-25	Use of thiazolidinediones to prevent or delay onset of NIDDM
KR20070011329A (ko)	2007-01-24	인슐린 저항성 개선제를 함유하는 당뇨병 치료제
MXPA02012619A (es)	2003-04-10	Tratamiento y prevencion de condiciones asociadas con resistencia a la insulina cardiaca.
HK1021326A (en)	2000-06-09	Composition for use in the treatment and prevention of hyperuricemia
MXPA97009958A (en)	1998-10-15	A method to reduce the amount of exogenous insulin administered to a patient with diabetes melitus dependent of insul
KR20010024481A (ko)	2001-03-26	고혈당증 치료용 티아졸리딘디온의 용도
HK1121074B (en)	2013-11-08	Treatment of type 2 diabetes with a combination of dpiv inhibitor and metformin or thiazolidinedione
MXPA00003634A (en)	2001-05-07	Use of thiazolidinediones for the treatment of hyperglycaemia
HK1003051B (en)	2002-06-07	Treatment and prophylaxis of pancreatitis