NO318070B1 - Substituerte, kondenserte heterosykliske forbindelser, farmasoytiske preparater som omfatter forbindelsene, og anvendelse av forbindelsene til fremstilling av medikamenter - Google Patents
Substituerte, kondenserte heterosykliske forbindelser, farmasoytiske preparater som omfatter forbindelsene, og anvendelse av forbindelsene til fremstilling av medikamenter Download PDFInfo
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- NO318070B1 NO318070B1 NO20001816A NO20001816A NO318070B1 NO 318070 B1 NO318070 B1 NO 318070B1 NO 20001816 A NO20001816 A NO 20001816A NO 20001816 A NO20001816 A NO 20001816A NO 318070 B1 NO318070 B1 NO 318070B1
- Authority
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- Norway
- Prior art keywords
- group
- substituted
- methyl
- benzyl
- ylmethoxy
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 67
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 title claims description 435
- 239000003814 drug Substances 0.000 title claims description 28
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 2,4-dioxothiazolidin-5-ylmethyl group Chemical group 0.000 claims abstract description 573
- 125000001424 substituent group Chemical group 0.000 claims abstract description 114
- 150000003839 salts Chemical class 0.000 claims abstract description 92
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 69
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 36
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 11
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000009471 action Effects 0.000 claims abstract description 4
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims abstract 4
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 90
- 239000012453 solvate Substances 0.000 claims description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 125000002252 acyl group Chemical group 0.000 claims description 35
- 125000003277 amino group Chemical group 0.000 claims description 31
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000003112 inhibitor Substances 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 22
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 229940079593 drug Drugs 0.000 claims description 17
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 16
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- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 239000003288 aldose reductase inhibitor Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
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- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
- 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 claims description 8
- 208000002249 Diabetes Complications Diseases 0.000 claims description 8
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 8
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229940031439 squalene Drugs 0.000 claims description 8
- 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 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 230000015556 catabolic process Effects 0.000 claims description 7
- 229940125753 fibrate Drugs 0.000 claims description 7
- 239000005541 ACE inhibitor Substances 0.000 claims description 6
- 229940123208 Biguanide Drugs 0.000 claims description 6
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 6
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
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- BWHWWBXNEKOWSU-UHFFFAOYSA-N 5-[[4-[(1-methyl-6-pyridin-2-ylsulfanylbenzimidazol-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(SC=3N=CC=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O BWHWWBXNEKOWSU-UHFFFAOYSA-N 0.000 claims description 5
- SYRRAMSPXNBYDW-UHFFFAOYSA-N 5-[[4-[[1-methyl-6-[4-(trifluoromethyl)phenoxy]benzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C=CC(=CC=3)C(F)(F)F)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O SYRRAMSPXNBYDW-UHFFFAOYSA-N 0.000 claims description 5
- XXRNRUVKDNYISF-UHFFFAOYSA-N 5-[[4-[[6-(2-chloro-4-hydroxy-3,5-dimethylphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=C(O)C(C)=CC(OC=2C=C3N(C)C(COC=4C=CC(CC5C(NC(=O)S5)=O)=CC=4)=NC3=CC=2)=C1Cl XXRNRUVKDNYISF-UHFFFAOYSA-N 0.000 claims description 5
- JCYNMRJCUYVDBC-UHFFFAOYSA-N 5-[[4-[[6-(4-amino-3,5-dimethylphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=C(N)C(C)=CC(OC=2C=C3N(C)C(COC=4C=CC(CC5C(NC(=O)S5)=O)=CC=4)=NC3=CC=2)=C1 JCYNMRJCUYVDBC-UHFFFAOYSA-N 0.000 claims description 5
- LJXNEIHQWFIITF-UHFFFAOYSA-N 5-[[4-[[6-(4-hydroxy-2,3,5-trimethylphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=C(O)C(C)=CC(OC=2C=C3N(C)C(COC=4C=CC(CC5C(NC(=O)S5)=O)=CC=4)=NC3=CC=2)=C1C LJXNEIHQWFIITF-UHFFFAOYSA-N 0.000 claims description 5
- SPKJZWQKMLJXDA-UHFFFAOYSA-N 5-[[4-[[6-(4-hydroxy-3,5-dimethylphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=C(O)C(C)=CC(OC=2C=C3N(C)C(COC=4C=CC(CC5C(NC(=O)S5)=O)=CC=4)=NC3=CC=2)=C1 SPKJZWQKMLJXDA-UHFFFAOYSA-N 0.000 claims description 5
- 229940118148 Aldose reductase inhibitor Drugs 0.000 claims description 5
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 5
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 5
- 210000001789 adipocyte Anatomy 0.000 claims description 5
- 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 230000009702 cancer cell proliferation Effects 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 230000000144 pharmacologic effect Effects 0.000 claims description 5
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 229940124125 5 Lipoxygenase inhibitor Drugs 0.000 claims description 4
- UTIAGHJNJCYHGQ-UHFFFAOYSA-N 5-[[4-[(1-methyl-6-pyridin-2-yloxybenzimidazol-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3N=CC=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O UTIAGHJNJCYHGQ-UHFFFAOYSA-N 0.000 claims description 4
- ORYFGBXBMZBSQG-UHFFFAOYSA-N 5-[[4-[[1-methyl-6-(2-morpholin-4-ylphenoxy)benzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C(=CC=CC=3)N3CCOCC3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O ORYFGBXBMZBSQG-UHFFFAOYSA-N 0.000 claims description 4
- IIPTYTQIUGLJAV-UHFFFAOYSA-N 5-[[4-[[1-methyl-6-(4-methylphenyl)sulfanylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN1C(=NC2=C1C=C(C=C2)SC2=CC=C(C=C2)C)COC2=CC=C(CC1C(NC(S1)=O)=O)C=C2 IIPTYTQIUGLJAV-UHFFFAOYSA-N 0.000 claims description 4
- SISWTCKMHBOBCN-UHFFFAOYSA-N 5-[[4-[[5-(4-hydroxy-2,3,5-trimethylphenoxy)-3-methylimidazo[4,5-b]pyridin-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=C(O)C(C)=CC(OC=2N=C3N(C)C(COC=4C=CC(CC5C(NC(=O)S5)=O)=CC=4)=NC3=CC=2)=C1C SISWTCKMHBOBCN-UHFFFAOYSA-N 0.000 claims description 4
- GORGWSHXSGRLPF-UHFFFAOYSA-N 5-[[4-[[6-(2,5-ditert-butyl-4-hydroxyphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C(=CC(O)=C(C=3)C(C)(C)C)C(C)(C)C)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O GORGWSHXSGRLPF-UHFFFAOYSA-N 0.000 claims description 4
- JMFSXAJSUMEVKH-UHFFFAOYSA-N 5-[[4-[[6-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanyl-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(SC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O JMFSXAJSUMEVKH-UHFFFAOYSA-N 0.000 claims description 4
- OPUBSKWBYMWPNA-UHFFFAOYSA-N 5-[[4-[[6-(4-methoxyphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(N=C(COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)N2C)C2=C1 OPUBSKWBYMWPNA-UHFFFAOYSA-N 0.000 claims description 4
- YGBHDHDPTMIQTF-UHFFFAOYSA-N 5-[[4-[[6-[3-(dimethylamino)phenoxy]-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CN(C)C1=CC=CC(OC=2C=C3N(C)C(COC=4C=CC(CC5C(NC(=O)S5)=O)=CC=4)=NC3=CC=2)=C1 YGBHDHDPTMIQTF-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
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- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 230000005779 cell damage Effects 0.000 claims description 4
- 208000037887 cell injury Diseases 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- LISJIBGNDVHMSL-UHFFFAOYSA-N 4-[2-[[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl]-3-methylbenzimidazol-5-yl]oxybenzonitrile Chemical compound N=1C2=CC=C(OC=3C=CC(=CC=3)C#N)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O LISJIBGNDVHMSL-UHFFFAOYSA-N 0.000 claims description 3
- BZWWLGZXHVOZIX-UHFFFAOYSA-N 5-[[4-[[1-methyl-6-(2-pyrrolidin-1-ylphenoxy)benzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C(=CC=CC=3)N3CCCC3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O BZWWLGZXHVOZIX-UHFFFAOYSA-N 0.000 claims description 3
- ZJHDULJHSAFEHQ-UHFFFAOYSA-N 5-[[4-[[6-(4-hydroxyphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C=CC(O)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O ZJHDULJHSAFEHQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 3
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- IENQNBPFZSLXPP-UHFFFAOYSA-N 5-[[4-[(1-methyl-6-pyridin-3-yloxybenzimidazol-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C=NC=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O IENQNBPFZSLXPP-UHFFFAOYSA-N 0.000 claims description 2
- KKMSJHDGUJSKBW-UHFFFAOYSA-N 5-[[4-[[1-methyl-6-(2-piperidin-1-ylphenoxy)benzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C(=CC=CC=3)N3CCCCC3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O KKMSJHDGUJSKBW-UHFFFAOYSA-N 0.000 claims description 2
- GWEPOWPXFLGWGF-UHFFFAOYSA-N 5-[[4-[[1-methyl-6-(4-phenylphenoxy)benzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C=CC(=CC=3)C=3C=CC=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O GWEPOWPXFLGWGF-UHFFFAOYSA-N 0.000 claims description 2
- DTUWPAQAXIPNKF-UHFFFAOYSA-N 5-[[4-[[6-(3,5-ditert-butyl-4-hydroxyphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O DTUWPAQAXIPNKF-UHFFFAOYSA-N 0.000 claims description 2
- MRKHEIJPLWAQEI-UHFFFAOYSA-N 5-[[4-[[6-(4-aminophenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C=CC(N)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O MRKHEIJPLWAQEI-UHFFFAOYSA-N 0.000 claims description 2
- MEOVPFOAIQSBPD-UHFFFAOYSA-N 5-[[4-[[6-(4-benzylphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound N=1C2=CC=C(OC=3C=CC(CC=4C=CC=CC=4)=CC=3)C=C2N(C)C=1COC(C=C1)=CC=C1CC1SC(=O)NC1=O MEOVPFOAIQSBPD-UHFFFAOYSA-N 0.000 claims description 2
- SJBODHIDWABJKP-UHFFFAOYSA-N 5-[[4-[[6-(4-hydroxy-2,5-dimethylphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(O)C(C)=CC(OC=2C=C3N(C)C(COC=4C=CC(CC5C(NC(=O)S5)=O)=CC=4)=NC3=CC=2)=C1C SJBODHIDWABJKP-UHFFFAOYSA-N 0.000 claims description 2
- WKECWJQAKLFOEC-UHFFFAOYSA-N 5-[[4-[[6-(4-hydroxy-2-methylphenoxy)-1-methylbenzimidazol-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC1=CC(O)=CC=C1OC1=CC=C(N=C(COC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)N2C)C2=C1 WKECWJQAKLFOEC-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 1
- 229950006343 zenarestat Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229950005346 zopolrestat Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or 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 in position 2
- C07D235/26—Oxygen atoms
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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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or 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 in position 2
- C07D235/28—Sulfur atoms
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or 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
- C07D263/44—Two oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or 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
- C07D277/34—Oxygen atoms
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/14—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 three or more hetero rings
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- 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)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
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- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27606397 | 1997-10-08 | ||
PCT/JP1998/004548 WO1999018081A1 (fr) | 1997-10-08 | 1998-10-08 | Composes heterocycliques condenses substitues |
Publications (3)
Publication Number | Publication Date |
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NO20001816D0 NO20001816D0 (no) | 2000-04-07 |
NO20001816L NO20001816L (no) | 2000-06-07 |
NO318070B1 true NO318070B1 (no) | 2005-01-31 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20001816A NO318070B1 (no) | 1997-10-08 | 2000-04-07 | Substituerte, kondenserte heterosykliske forbindelser, farmasoytiske preparater som omfatter forbindelsene, og anvendelse av forbindelsene til fremstilling av medikamenter |
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US (1) | US6432993B1 (zh) |
EP (1) | EP1022272B1 (zh) |
KR (1) | KR100666887B1 (zh) |
CN (1) | CN1255386C (zh) |
AT (1) | ATE267814T1 (zh) |
AU (1) | AU740704B2 (zh) |
BR (1) | BR9813848B1 (zh) |
CA (1) | CA2305807C (zh) |
CZ (1) | CZ302475B6 (zh) |
DE (1) | DE69824194T2 (zh) |
DK (1) | DK1022272T3 (zh) |
ES (1) | ES2221203T3 (zh) |
HK (1) | HK1027354A1 (zh) |
HU (1) | HU228193B1 (zh) |
ID (1) | ID23891A (zh) |
IL (1) | IL135537A (zh) |
MX (1) | MXPA00003546A (zh) |
NO (1) | NO318070B1 (zh) |
NZ (1) | NZ503794A (zh) |
PL (1) | PL200859B1 (zh) |
PT (1) | PT1022272E (zh) |
RU (1) | RU2196141C2 (zh) |
TR (1) | TR200000946T2 (zh) |
TW (1) | TW475931B (zh) |
WO (1) | WO1999018081A1 (zh) |
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CZ2002178A3 (cs) * | 1999-07-19 | 2002-05-15 | Sankyo Company Limited | Terapeutické a profylaktické látky pro nádorová onemocnění |
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US11319313B2 (en) | 2020-06-30 | 2022-05-03 | Poxel Sa | Crystalline forms of deuterium-enriched pioglitazone |
Family Cites Families (13)
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JPH06779B2 (ja) * | 1985-06-10 | 1994-01-05 | 武田薬品工業株式会社 | チアゾリジオン誘導体およびそれを含んでなる医薬組成物 |
US5143930A (en) | 1990-02-07 | 1992-09-01 | Sankyo Company, Limited | Thiazolidine derivatives with anti-diabetic activity, their preparation and their use |
GB9017218D0 (en) | 1990-08-06 | 1990-09-19 | Beecham Group Plc | Novel compounds |
EP0544696B1 (en) | 1990-08-23 | 1995-01-11 | Pfizer Inc. | Hypoglycemic hydroxyurea derivatives |
GB9023585D0 (en) | 1990-10-30 | 1990-12-12 | Beecham Group Plc | Novel compounds |
GB9023584D0 (en) | 1990-10-30 | 1990-12-12 | Beecham Group Plc | Novel compounds |
NO305987B1 (no) | 1994-04-11 | 1999-08-30 | Sankyo Co | Heterosykliske forbindelser med antidiabetisk aktivitet, deres anvendelse og farmasoeytisk preparat inneholdende disse |
IL118474A (en) * | 1995-06-01 | 2001-08-08 | Sankyo Co | Benzimideol derivatives and pharmaceutical preparations containing them |
JP3291164B2 (ja) * | 1995-06-02 | 2002-06-10 | 日石三菱株式会社 | 接触分解ガソリンの脱硫方法 |
US5798375A (en) | 1995-07-03 | 1998-08-25 | Sankyo Company, Limited | Treatment of arteriosclerosis and xanthoma |
JP3651816B2 (ja) * | 1995-07-03 | 2005-05-25 | 三共株式会社 | 動脈硬化症予防および治療剤 |
IL120443A (en) * | 1996-03-18 | 2000-07-16 | Sankyo Co | Use of an insulin sensitizer for the manufacture of a medicament for the treatment or prophylaxis of pancreatitis |
JPH1072371A (ja) * | 1996-08-28 | 1998-03-17 | Sankyo Co Ltd | 回腸型胆汁酸トランスポーター阻害剤 |
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