SK9212000A3 - Arylthiazolidinedione derivatives, pharmaceutical compositions comprising the same and use thereof - Google Patents

Info

Publication number

SK9212000A3

SK9212000A3 SK921-2000A SK9212000A SK9212000A3 SK 9212000 A3 SK9212000 A3 SK 9212000A3 SK 9212000 A SK9212000 A SK 9212000A SK 9212000 A3 SK9212000 A3 SK 9212000A3

Authority

SK

Slovakia

Prior art keywords

propyl

alkyl

phenyl

optionally substituted

nmr

Prior art date

1997-12-19

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims description 20
• 238000011282 treatment Methods 0.000 claims abstract description 18
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 10
• 201000001421 hyperglycemia Diseases 0.000 claims abstract description 9
• 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 6
• 208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 6
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 5
• 208000008589 Obesity Diseases 0.000 claims abstract description 4
• 235000020824 obesity Nutrition 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 241
• -1 3-propyl Chemical group 0.000 claims description 95
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 93
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
• 125000000217 alkyl group Chemical group 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 48
• 125000001072 heteroaryl group Chemical class 0.000 claims description 24
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000000732 arylene group Chemical group 0.000 claims description 7
• 125000001589 carboacyl group Chemical group 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000005549 heteroarylene group Chemical group 0.000 claims description 5
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000005979 2-naphthyloxy group Chemical group 0.000 claims description 2
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 abstract description 15
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 abstract description 15
• 239000000556 agonist Substances 0.000 abstract description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
• 108010016731 PPAR gamma Proteins 0.000 abstract description 12
• 102000023984 PPAR alpha Human genes 0.000 abstract description 10
• 201000010099 disease Diseases 0.000 abstract description 7
• 108010015181 PPAR delta Proteins 0.000 abstract description 6
• 208000035475 disorder Diseases 0.000 abstract description 6
• 230000002265 prevention Effects 0.000 abstract description 5
• 201000001320 Atherosclerosis Diseases 0.000 abstract description 3
• 230000001404 mediated effect Effects 0.000 abstract description 3
• 230000003389 potentiating effect Effects 0.000 abstract description 3
• 208000037803 restenosis Diseases 0.000 abstract description 3
• 230000002792 vascular Effects 0.000 abstract description 3
• 108010028924 PPAR alpha Proteins 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 178
• 238000005481 NMR spectroscopy Methods 0.000 description 163
• 238000002360 preparation method Methods 0.000 description 140
• 239000007858 starting material Substances 0.000 description 111
• 239000000243 solution Substances 0.000 description 80
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 68
• 238000000034 method Methods 0.000 description 64
• 235000019439 ethyl acetate Nutrition 0.000 description 60
• 239000012044 organic layer Substances 0.000 description 60
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
• 239000011541 reaction mixture Substances 0.000 description 57
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 55
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
• 239000003921 oil Substances 0.000 description 49
• 235000019198 oils Nutrition 0.000 description 49
• 239000000741 silica gel Substances 0.000 description 46
• 229910002027 silica gel Inorganic materials 0.000 description 46
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 44
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 229940049953 phenylacetate Drugs 0.000 description 29
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
• 229910052938 sodium sulfate Inorganic materials 0.000 description 27
• 235000011152 sodium sulphate Nutrition 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 24
• 239000000203 mixture Substances 0.000 description 24
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 24
• IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 22
• 229940125396 insulin Drugs 0.000 description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• 239000000460 chlorine Substances 0.000 description 20
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
• 235000019341 magnesium sulphate Nutrition 0.000 description 20
• IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 20
• 239000007787 solid Substances 0.000 description 20
• 102000004877 Insulin Human genes 0.000 description 19
• 108090001061 Insulin Proteins 0.000 description 19
• 239000000047 product Substances 0.000 description 19
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 16
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetic acid ester Natural products CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 14
• 239000004480 active ingredient Substances 0.000 description 14
• 239000012267 brine Substances 0.000 description 13
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 13
• 229910000024 caesium carbonate Inorganic materials 0.000 description 13
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• 238000010992 reflux Methods 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
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• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](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 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
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• 239000008103 glucose Substances 0.000 description 11
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• 239000002904 solvent Substances 0.000 description 11
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• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 9
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• YCHPISIBGXGDJE-UHFFFAOYSA-N 5-[4-(2-phenylethoxy)phenyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1C(C=C1)=CC=C1OCCC1=CC=CC=C1 YCHPISIBGXGDJE-UHFFFAOYSA-N 0.000 description 4
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