TWI235061B - Substituted azole acid derivatives useful as antidiabetic and antiobesity agents and pharmaceutical compositions containing same - Google Patents

Info

Publication number

TWI235061B

TWI235061B TW091111100A TW91111100A TWI235061B TW I235061 B TWI235061 B TW I235061B TW 091111100 A TW091111100 A TW 091111100A TW 91111100 A TW91111100 A TW 91111100A TW I235061 B TWI235061 B TW I235061B

Authority

TW

Taiwan

Prior art keywords

compound

ministry

page

cns

economic affairs

Prior art date

2001-05-30

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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
• 239000003472 antidiabetic agent Substances 0.000 title abstract description 30
• 239000000883 anti-obesity agent Substances 0.000 title abstract description 8
• 229940125710 antiobesity agent Drugs 0.000 title abstract description 7
• 230000003178 anti-diabetic effect Effects 0.000 title abstract description 6
• 239000002253 acid Substances 0.000 title description 59
• 229940125708 antidiabetic agent Drugs 0.000 title description 23
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 15
• 150000003851 azoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 253
• 208000008589 Obesity Diseases 0.000 claims abstract description 32
• 235000020824 obesity Nutrition 0.000 claims abstract description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
• 238000011049 filling Methods 0.000 claims description 159
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• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 70
• 239000012190 activator Substances 0.000 claims description 69
• 230000002079 cooperative effect Effects 0.000 claims description 59
• 239000005557 antagonist Substances 0.000 claims description 54
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• 102000023984 PPAR alpha Human genes 0.000 claims description 36
• 108010028924 PPAR alpha Proteins 0.000 claims description 35
• 108090000623 proteins and genes Proteins 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 150000002148 esters Chemical class 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 206010012601 diabetes mellitus Diseases 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
• 239000000194 fatty acid Substances 0.000 claims description 14
• 229930195729 fatty acid Natural products 0.000 claims description 14
• 150000004665 fatty acids Chemical class 0.000 claims description 14
• 102000004881 Angiotensinogen Human genes 0.000 claims description 12
• 108090001067 Angiotensinogen Proteins 0.000 claims description 12
• 230000014509 gene expression Effects 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 11
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 9
• 239000008103 glucose Substances 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 239000000651 prodrug Chemical class 0.000 claims description 9
• 229940002612 prodrug Drugs 0.000 claims description 9
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• 210000004369 blood Anatomy 0.000 claims description 7
• 239000008280 blood Substances 0.000 claims description 7
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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• PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 124
• -1 eneoxycarbonyl Chemical group 0.000 description 124
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 104
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• 239000007787 solid Substances 0.000 description 60
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
• 239000003112 inhibitor Substances 0.000 description 49
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 45
• 230000000694 effects Effects 0.000 description 45
• 229910052938 sodium sulfate Inorganic materials 0.000 description 45
• 235000011152 sodium sulphate Nutrition 0.000 description 45
• 229940126062 Compound A Drugs 0.000 description 44
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 43
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 37
• 230000000875 corresponding effect Effects 0.000 description 37
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
• 239000012074 organic phase Substances 0.000 description 36
• 238000003786 synthesis reaction Methods 0.000 description 36
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• 125000003118 aryl group Chemical group 0.000 description 34
• 230000015572 biosynthetic process Effects 0.000 description 33
• 239000000741 silica gel Substances 0.000 description 33
• 229910002027 silica gel Inorganic materials 0.000 description 33
• 238000011282 treatment Methods 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
• 235000019441 ethanol Nutrition 0.000 description 31
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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• 238000000746 purification Methods 0.000 description 27
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• 210000004027 cell Anatomy 0.000 description 25
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