CA2371308A1 - Tri-aryl acid derivatives as ppar receptor ligands - Google Patents
Tri-aryl acid derivatives as ppar receptor ligands Download PDFInfo
- Publication number
- CA2371308A1 CA2371308A1 CA002371308A CA2371308A CA2371308A1 CA 2371308 A1 CA2371308 A1 CA 2371308A1 CA 002371308 A CA002371308 A CA 002371308A CA 2371308 A CA2371308 A CA 2371308A CA 2371308 A1 CA2371308 A1 CA 2371308A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- methyl
- hydrogen
- fused
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 239000003446 ligand Substances 0.000 title claims abstract description 25
- 239000002253 acid Substances 0.000 title abstract description 42
- 101150014691 PPARA gene Proteins 0.000 title description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 73
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 70
- 239000000126 substance Substances 0.000 claims abstract description 68
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 44
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 44
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 29
- 102000005962 receptors Human genes 0.000 claims abstract description 25
- 108020003175 receptors Proteins 0.000 claims abstract description 25
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 20
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 399
- -1 quinazolin-4-onyl Chemical group 0.000 claims description 350
- 238000000034 method Methods 0.000 claims description 138
- 125000000217 alkyl group Chemical group 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 116
- 239000001257 hydrogen Substances 0.000 claims description 111
- 150000003839 salts Chemical class 0.000 claims description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
- 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 claims description 46
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 24
- 102000004877 Insulin Human genes 0.000 claims description 23
- 108090001061 Insulin Proteins 0.000 claims description 23
- 229940125396 insulin Drugs 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 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 15
- 150000001204 N-oxides Chemical class 0.000 claims description 15
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 15
- 239000008103 glucose Substances 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 206010012601 diabetes mellitus Diseases 0.000 claims description 14
- 206010022489 Insulin Resistance Diseases 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 235000021588 free fatty acids Nutrition 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 230000027455 binding Effects 0.000 claims description 10
- 201000001421 hyperglycemia Diseases 0.000 claims description 10
- 201000008980 hyperinsulinism Diseases 0.000 claims description 9
- 208000011580 syndromic disease Diseases 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000003435 aroyl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 230000001627 detrimental effect Effects 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000030814 Eating disease Diseases 0.000 claims description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 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 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 230000036765 blood level Effects 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 20
- 230000001270 agonistic effect Effects 0.000 claims 2
- 230000003042 antagnostic effect Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 239000000556 agonist Substances 0.000 abstract description 11
- 239000011230 binding agent Substances 0.000 abstract description 8
- 239000005557 antagonist Substances 0.000 abstract description 5
- 102000034570 NR1 subfamily Human genes 0.000 abstract 1
- 108020001305 NR1 subfamily Proteins 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 204
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 149
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 140
- 238000005481 NMR spectroscopy Methods 0.000 description 132
- 239000000243 solution Substances 0.000 description 115
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 109
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 103
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 94
- 238000006243 chemical reaction Methods 0.000 description 89
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 235000019439 ethyl acetate Nutrition 0.000 description 74
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- 229910052757 nitrogen Inorganic materials 0.000 description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 60
- 229940050390 benzoate Drugs 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- 101150041968 CDC13 gene Proteins 0.000 description 53
- 239000000203 mixture Substances 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- 239000000377 silicon dioxide Substances 0.000 description 50
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 48
- 239000005711 Benzoic acid Substances 0.000 description 46
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- 229910000104 sodium hydride Inorganic materials 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 229940095102 methyl benzoate Drugs 0.000 description 33
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 31
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
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- 239000012044 organic layer Substances 0.000 description 25
- 229910000027 potassium carbonate Inorganic materials 0.000 description 25
- 125000006413 ring segment Chemical group 0.000 description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
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- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 8
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 8
- 229960003105 metformin Drugs 0.000 description 8
- UDNSKBMNXZVXKW-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1CBr UDNSKBMNXZVXKW-UHFFFAOYSA-N 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 8
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- LFOROOKWYBROJA-UHFFFAOYSA-N methyl 2-[2-methyl-6-[[3-(quinolin-2-ylmethoxy)phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 LFOROOKWYBROJA-UHFFFAOYSA-N 0.000 description 1
- AWWWWEDDRYXNBE-UHFFFAOYSA-N methyl 2-[[3-(quinolin-2-ylmethoxy)phenoxy]methyl]-3h-thiophene-2-carboxylate Chemical compound C=1C=CC(OCC=2N=C3C=CC=CC3=CC=2)=CC=1OCC1(C(=O)OC)CC=CS1 AWWWWEDDRYXNBE-UHFFFAOYSA-N 0.000 description 1
- NERYXMCYIODOSZ-UHFFFAOYSA-N methyl 2-[[3-(quinolin-2-ylmethoxy)phenyl]methoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC1=CC=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 NERYXMCYIODOSZ-UHFFFAOYSA-N 0.000 description 1
- PIUSHKPCOPHPJF-UHFFFAOYSA-N methyl 2-[[3-[(2,4-dichlorophenyl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C(=CC(Cl)=CC=2)Cl)=C1 PIUSHKPCOPHPJF-UHFFFAOYSA-N 0.000 description 1
- WJMYZZHDCPTOPX-UHFFFAOYSA-N methyl 2-[[3-[(2,5-dimethylphenyl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C(=CC=C(C)C=2)C)=C1 WJMYZZHDCPTOPX-UHFFFAOYSA-N 0.000 description 1
- HWKMLNOBBANACI-UHFFFAOYSA-N methyl 2-[[3-[(2-cyclohexyl-1,3-oxazol-4-yl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C(OC=2)C2CCCCC2)=C1 HWKMLNOBBANACI-UHFFFAOYSA-N 0.000 description 1
- GOSAGHMJTSKBOD-UHFFFAOYSA-N methyl 2-[[3-[(3,5-dimethyl-1,2-oxazol-4-yl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC2=C(ON=C2C)C)=C1 GOSAGHMJTSKBOD-UHFFFAOYSA-N 0.000 description 1
- ONKMIOBXDYNNGK-UHFFFAOYSA-N methyl 2-[[3-[(3-bromophenyl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C=C(Br)C=CC=2)=C1 ONKMIOBXDYNNGK-UHFFFAOYSA-N 0.000 description 1
- LEXPHFBVTFXWHQ-UHFFFAOYSA-N methyl 2-[[3-[(4-ethylphenyl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound C1=CC(CC)=CC=C1COC1=CC=CC(OCC=2C(=C(C)C=CC=2)C(=O)OC)=C1 LEXPHFBVTFXWHQ-UHFFFAOYSA-N 0.000 description 1
- WPBWVRJHOQRNEI-UHFFFAOYSA-N methyl 2-[[3-[(4-tert-butylcyclohexyl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC2CCC(CC2)C(C)(C)C)=C1 WPBWVRJHOQRNEI-UHFFFAOYSA-N 0.000 description 1
- PYPQECUZMIYIGC-UHFFFAOYSA-N methyl 2-[[3-[(4-tert-butylphenyl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C=CC(=CC=2)C(C)(C)C)=C1 PYPQECUZMIYIGC-UHFFFAOYSA-N 0.000 description 1
- WKZLHOBHIIHJMJ-UHFFFAOYSA-N methyl 2-[[3-[(5-acetyl-2-methoxyphenyl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C(=CC=C(C=2)C(C)=O)OC)=C1 WKZLHOBHIIHJMJ-UHFFFAOYSA-N 0.000 description 1
- OVSILABHTPNMQM-UHFFFAOYSA-N methyl 2-[[3-[(5-ethylpyridin-2-yl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound N1=CC(CC)=CC=C1COC1=CC=CC(OCC=2C(=C(C)C=CC=2)C(=O)OC)=C1 OVSILABHTPNMQM-UHFFFAOYSA-N 0.000 description 1
- BETKFKYGYMTJON-UHFFFAOYSA-N methyl 2-[[3-[(5-tert-butyl-1,2,4-oxadiazol-3-yl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C(ON=2)C(C)(C)C)=C1 BETKFKYGYMTJON-UHFFFAOYSA-N 0.000 description 1
- PWOPGERPVCAJPK-UHFFFAOYSA-N methyl 2-[[3-[(6-fluoroquinolin-2-yl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C3C=CC(F)=CC3=CC=2)=C1 PWOPGERPVCAJPK-UHFFFAOYSA-N 0.000 description 1
- JXWUMZHFKAXCIT-UHFFFAOYSA-N methyl 2-[[3-[(6-methoxyquinolin-2-yl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C3C=CC(OC)=CC3=CC=2)=C1 JXWUMZHFKAXCIT-UHFFFAOYSA-N 0.000 description 1
- AZQJFJKAUAJKKY-UHFFFAOYSA-N methyl 2-[[3-[(7-chloroquinolin-2-yl)methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C3C=C(Cl)C=CC3=CC=2)=C1 AZQJFJKAUAJKKY-UHFFFAOYSA-N 0.000 description 1
- IJJUPNBBPYGZGR-UHFFFAOYSA-N methyl 2-[[3-[[2-(3-fluorophenyl)-1,3-oxazol-4-yl]methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C(OC=2)C=2C=C(F)C=CC=2)=C1 IJJUPNBBPYGZGR-UHFFFAOYSA-N 0.000 description 1
- SVSSNKPHYQUAFF-UHFFFAOYSA-N methyl 2-[[3-[[2-(4-fluorophenyl)-1,3-oxazol-4-yl]methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C(OC=2)C=2C=CC(F)=CC=2)=C1 SVSSNKPHYQUAFF-UHFFFAOYSA-N 0.000 description 1
- DIWDSBUPTUXHQD-UHFFFAOYSA-N methyl 2-[[3-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]phenoxy]methyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C(=NOC=2C)C=2C(=CC=CC=2Cl)Cl)=C1 DIWDSBUPTUXHQD-UHFFFAOYSA-N 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- WGCAVSGJGHSWPG-UHFFFAOYSA-N methyl 2-methoxy-6-[[3-(quinolin-2-ylmethoxy)phenyl]methoxy]benzoate Chemical compound COC(=O)C1=C(OC)C=CC=C1OCC1=CC=CC(OCC=2N=C3C=CC=CC3=CC=2)=C1 WGCAVSGJGHSWPG-UHFFFAOYSA-N 0.000 description 1
- BMSIMRDRVVXERY-UHFFFAOYSA-N methyl 2-methyl-6-[[3-(2-pyridin-2-ylethoxy)phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCCC=2N=CC=CC=2)=C1 BMSIMRDRVVXERY-UHFFFAOYSA-N 0.000 description 1
- CQNSNESUAPDCJP-UHFFFAOYSA-N methyl 2-methyl-6-[[3-(naphthalen-2-ylmethoxy)phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C=C3C=CC=CC3=CC=2)=C1 CQNSNESUAPDCJP-UHFFFAOYSA-N 0.000 description 1
- HYRDDSQWSUPSGJ-UHFFFAOYSA-N methyl 2-methyl-6-[[3-(pyridin-2-ylmethoxy)phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=CC=CC=2)=C1 HYRDDSQWSUPSGJ-UHFFFAOYSA-N 0.000 description 1
- RQNKCXYUVVLNPT-UHFFFAOYSA-N methyl 2-methyl-6-[[3-(pyridin-2-ylmethoxymethyl)phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(COCC=2N=CC=CC=2)=C1 RQNKCXYUVVLNPT-UHFFFAOYSA-N 0.000 description 1
- UYMNKIOAHURKDG-UHFFFAOYSA-N methyl 2-methyl-6-[[3-(quinoxalin-2-ylmethoxy)phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C3C=CC=CC3=NC=2)=C1 UYMNKIOAHURKDG-UHFFFAOYSA-N 0.000 description 1
- CEOYROWUZNSIRC-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(2,4,5-trimethylphenyl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C(=CC(C)=C(C)C=2)C)=C1 CEOYROWUZNSIRC-UHFFFAOYSA-N 0.000 description 1
- QRGGDXASZXCPTJ-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(2-methylphenyl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C(=CC=CC=2)C)=C1 QRGGDXASZXCPTJ-UHFFFAOYSA-N 0.000 description 1
- SDMBKTYFSDHECZ-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C(OC=2)C=2C=CC=CC=2)=C1 SDMBKTYFSDHECZ-UHFFFAOYSA-N 0.000 description 1
- TZKWIYQMFHSDQV-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(2-phenyl-1,3-thiazol-4-yl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C(SC=2)C=2C=CC=CC=2)=C1 TZKWIYQMFHSDQV-UHFFFAOYSA-N 0.000 description 1
- FHPSTJQFPVEYJT-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(3-methylquinoxalin-2-yl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C(=NC3=CC=CC=C3N=2)C)=C1 FHPSTJQFPVEYJT-UHFFFAOYSA-N 0.000 description 1
- HPTJEMYNOAPQNO-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(3-phenoxyphenyl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C=C(OC=3C=CC=CC=3)C=CC=2)=C1 HPTJEMYNOAPQNO-UHFFFAOYSA-N 0.000 description 1
- ZPPQNSIQMGWSCQ-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(4-propan-2-ylphenyl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2C=CC(=CC=2)C(C)C)=C1 ZPPQNSIQMGWSCQ-UHFFFAOYSA-N 0.000 description 1
- HBWQSSONZQZPIG-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=C(ON=2)C=2C=CC=CC=2)=C1 HBWQSSONZQZPIG-UHFFFAOYSA-N 0.000 description 1
- ITVQTKOSOHBEAB-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[(5-phenylpyridin-2-yl)methoxy]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(OCC=2N=CC(=CC=2)C=2C=CC=CC=2)=C1 ITVQTKOSOHBEAB-UHFFFAOYSA-N 0.000 description 1
- RQBCBTBTWNJYIQ-UHFFFAOYSA-N methyl 2-methyl-6-[[3-[[methyl(quinolin-2-yl)amino]methyl]phenoxy]methyl]benzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1=CC=CC(CN(C)C=2N=C3C=CC=CC3=CC=2)=C1 RQBCBTBTWNJYIQ-UHFFFAOYSA-N 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical class C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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| US6414002B1 (en) | 1999-09-22 | 2002-07-02 | Bristol-Myers Squibb Company | Substituted acid derivatives useful as antidiabetic and antiobesity agents and method |
| TW200528436A (en) | 1999-09-22 | 2005-09-01 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
| AU2001272098A1 (en) * | 2000-03-09 | 2001-09-17 | Sanofi-Aventis Deutschland Gmbh | Therapeutic uses of PPAR mediators |
| JP2001261654A (ja) * | 2000-03-21 | 2001-09-26 | Mitsui Chemicals Inc | キノリン誘導体およびそれを有効成分として含有する核内レセプター作動薬 |
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| EP1357115B1 (en) * | 2000-12-28 | 2009-06-17 | Takeda Pharmaceutical Company Limited | Alkanoic acid derivatives, process for their production and use thereof |
| WO2002064632A2 (en) * | 2001-02-01 | 2002-08-22 | Smithkline Beecham Corporation | Crystallized ppar$g(a) ligand binding domain polypeptide and screening methods employing same |
| EP1394154A4 (en) * | 2001-03-23 | 2005-05-18 | Takeda Pharmaceutical | FIVE-GLASS HETEROCYCLIC ALKANIC ACID DERIVATIVE |
| WO2002079162A1 (en) * | 2001-03-28 | 2002-10-10 | Eisai Co., Ltd. | Carboxylic acids |
| JP4549021B2 (ja) | 2001-03-30 | 2010-09-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ベンゼン化合物およびその塩 |
| TWI311133B (en) * | 2001-04-20 | 2009-06-21 | Eisai R&D Man Co Ltd | Carboxylic acid derivativeand the salt thereof |
| US20030092736A1 (en) * | 2001-05-30 | 2003-05-15 | Cheng Peter T. | Substituted azole acid derivatives useful as antidiabetic and antiobesity agents and method |
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| US20110065129A1 (en) | 2001-07-27 | 2011-03-17 | Lowe Derek B | Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation |
| AR036237A1 (es) | 2001-07-27 | 2004-08-25 | Bayer Corp | Derivados del acido indan acetico, intermediarios, y metodo para su preparacion, composicion farmaceutica y el uso de dichos derivados para la manufactura de un medicamento |
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| US7399777B2 (en) | 2001-08-31 | 2008-07-15 | Sanofi-Aventis Deutschland Gmbh | Diarylcycloalkyl derivatives, processes for their preparation and their use as pharmceuticals |
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