ES2887011T3 - Derivados de isotiazol como agonistas de GPR120 para el tratamiento de diabetes de tipo II - Google Patents

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Publication number

ES2887011T3

ES2887011T3 ES18169025T ES18169025T ES2887011T3 ES 2887011 T3 ES2887011 T3 ES 2887011T3 ES 18169025 T ES18169025 T ES 18169025T ES 18169025 T ES18169025 T ES 18169025T ES 2887011 T3 ES2887011 T3 ES 2887011T3

Authority

ES

Spain

Prior art keywords

trifluoromethyl

methoxy

ethyl

equiv

mmol

Prior art date

2014-03-07

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.)

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• 102100040134 Free fatty acid receptor 4 Human genes 0.000 title description 28
• 101000890672 Homo sapiens Free fatty acid receptor 4 Proteins 0.000 title description 28
• 208000001072 type 2 diabetes mellitus Diseases 0.000 title description 28
• 238000011282 treatment Methods 0.000 title description 15
• 239000000556 agonist Substances 0.000 title description 9
• 150000003854 isothiazoles Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 320
• -1 4-methylcyclohex-1-en-1-yl Chemical group 0.000 claims abstract description 115
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 102
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 96
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 65
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 57
• 125000001424 substituent group Chemical group 0.000 claims abstract description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 45
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
• 239000000460 chlorine Substances 0.000 claims abstract description 36
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 32
• 150000003839 salts Chemical group 0.000 claims abstract description 30
• 239000001257 hydrogen Substances 0.000 claims abstract description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 26
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 24
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 13
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 12
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 11
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 10
• 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims abstract description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
• 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 6
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 6
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims abstract description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 478
• 239000007787 solid Substances 0.000 description 300
• 239000000243 solution Substances 0.000 description 289
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 252
• 238000000034 method Methods 0.000 description 218
• 239000000203 mixture Substances 0.000 description 197
• 239000000047 product Substances 0.000 description 189
• 238000001819 mass spectrum Methods 0.000 description 177
• 238000005160 1H NMR spectroscopy Methods 0.000 description 176
• 235000019439 ethyl acetate Nutrition 0.000 description 163
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
• 230000007062 hydrolysis Effects 0.000 description 122
• 238000006460 hydrolysis reaction Methods 0.000 description 122
• 239000003208 petroleum Substances 0.000 description 117
• 239000003921 oil Substances 0.000 description 116
• 235000019198 oils Nutrition 0.000 description 116
• 238000006243 chemical reaction Methods 0.000 description 112
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 112
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 82
• 239000000741 silica gel Substances 0.000 description 82
• 229910002027 silica gel Inorganic materials 0.000 description 82
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 81
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 78
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
• 230000008878 coupling Effects 0.000 description 72
• 238000010168 coupling process Methods 0.000 description 72
• 238000005859 coupling reaction Methods 0.000 description 72
• 239000012044 organic layer Substances 0.000 description 67
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 62
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
• 239000002253 acid Substances 0.000 description 49
• 239000007822 coupling agent Substances 0.000 description 49
• 229910052757 nitrogen Inorganic materials 0.000 description 40
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 39
• 238000003756 stirring Methods 0.000 description 38
• 239000012298 atmosphere Substances 0.000 description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 37
• FRPDXOMKOVSTND-UHFFFAOYSA-N ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(O)C(C)=C1C FRPDXOMKOVSTND-UHFFFAOYSA-N 0.000 description 36
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 36
• 238000004809 thin layer chromatography Methods 0.000 description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
• IJAFUGGGBHSCAW-UHFFFAOYSA-N ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC(F)=C(O)C(F)=C1 IJAFUGGGBHSCAW-UHFFFAOYSA-N 0.000 description 25
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 24
• 230000009467 reduction Effects 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
• 208000035475 disorder Diseases 0.000 description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
• 208000008589 Obesity Diseases 0.000 description 20
• 235000020824 obesity Nutrition 0.000 description 20
• 239000011737 fluorine Substances 0.000 description 19
• 229910052731 fluorine Inorganic materials 0.000 description 19
• 239000012299 nitrogen atmosphere Substances 0.000 description 19
• 239000007858 starting material Substances 0.000 description 19
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 18
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 18
• 239000012230 colorless oil Substances 0.000 description 18
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 16
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 16
• 239000001294 propane Substances 0.000 description 16
• 235000019260 propionic acid Nutrition 0.000 description 16
• 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 15
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 15
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 102100040918 Pro-glucagon Human genes 0.000 description 15
• 201000010099 disease Diseases 0.000 description 15
• 239000003960 organic solvent Substances 0.000 description 15
• 239000011780 sodium chloride Substances 0.000 description 15
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 206010012601 diabetes mellitus Diseases 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 14
• 239000012071 phase Substances 0.000 description 14
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
• MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 13
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
• 208000011580 syndromic disease Diseases 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 239000003248 enzyme activator Substances 0.000 description 11
• 239000008194 pharmaceutical composition Substances 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• 206010022489 Insulin Resistance Diseases 0.000 description 10
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 9
• 239000012043 crude product Substances 0.000 description 9
• 239000003085 diluting agent Substances 0.000 description 9
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
• UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 9
• 241000282414 Homo sapiens Species 0.000 description 8
• 208000001145 Metabolic Syndrome Diseases 0.000 description 8
• 125000003118 aryl group Chemical group 0.000 description 8
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
• 125000000623 heterocyclic group Chemical group 0.000 description 8
• 239000000546 pharmaceutical excipient Substances 0.000 description 8
• 239000012453 solvate Substances 0.000 description 8
• ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 7
• YKFAFWKDOSYQIP-UHFFFAOYSA-N 4-ethylbenzamide Chemical compound CCC1=CC=C(C(N)=O)C=C1 YKFAFWKDOSYQIP-UHFFFAOYSA-N 0.000 description 7
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
• 208000024172 Cardiovascular disease Diseases 0.000 description 7
• 208000032928 Dyslipidaemia Diseases 0.000 description 7
• 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 description 7
• 208000017170 Lipid metabolism disease Diseases 0.000 description 7
• XUZSXTCZJKQFCU-UHFFFAOYSA-N [3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methyl methanesulfonate Chemical compound C1=CC(CC)=CC=C1C1=NSC(C(F)(F)F)=C1COS(C)(=O)=O XUZSXTCZJKQFCU-UHFFFAOYSA-N 0.000 description 7
• 229960000583 acetic acid Drugs 0.000 description 7
• 229910052799 carbon Inorganic materials 0.000 description 7
• 239000008103 glucose Substances 0.000 description 7
• 125000001072 heteroaryl group Chemical group 0.000 description 7
• 125000005842 heteroatom Chemical group 0.000 description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
• UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 7
• 230000008569 process Effects 0.000 description 7
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 7
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 6
• WKAITTMZJQQYEI-UHFFFAOYSA-N 3,5-dichloro-1,2-thiazole-4-carboxylic acid Chemical compound OC(=O)C=1C(Cl)=NSC=1Cl WKAITTMZJQQYEI-UHFFFAOYSA-N 0.000 description 6
• HRPBCNQKPJKETN-UHFFFAOYSA-N 4-chloro-3-fluorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C(F)=C1 HRPBCNQKPJKETN-UHFFFAOYSA-N 0.000 description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• 235000011054 acetic acid Nutrition 0.000 description 6
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 125000001207 fluorophenyl group Chemical group 0.000 description 6
• 235000021588 free fatty acids Nutrition 0.000 description 6
• BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical group CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 6
• 229910052760 oxygen Inorganic materials 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• 229910052717 sulfur Inorganic materials 0.000 description 6
• 125000003944 tolyl group Chemical group 0.000 description 6
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• HPKBQBQMXYLUBI-UHFFFAOYSA-N 3-(4-hydroxy-2,3-dimethylphenyl)propanoic acid Chemical compound CC1=C(C)C(CCC(O)=O)=CC=C1O HPKBQBQMXYLUBI-UHFFFAOYSA-N 0.000 description 5
• BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 description 5
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
• 241001465754 Metazoa Species 0.000 description 5
• ZFDWRCZVCMWFIM-UHFFFAOYSA-N [3-(4-chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol Chemical compound S1C(C(F)(F)F)=C(CO)C(C=2C=CC(Cl)=CC=2)=N1 ZFDWRCZVCMWFIM-UHFFFAOYSA-N 0.000 description 5
• 201000010390 abdominal obesity-metabolic syndrome 1 Diseases 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 229910000085 borane Inorganic materials 0.000 description 5
• REZNQKBGCOTNER-UHFFFAOYSA-N ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-methylpropanoate Chemical compound CCOC(=O)C(C)CC1=CC(F)=C(O)C(F)=C1 REZNQKBGCOTNER-UHFFFAOYSA-N 0.000 description 5
• 238000004128 high performance liquid chromatography Methods 0.000 description 5
• 150000002431 hydrogen Chemical class 0.000 description 5
• 230000003914 insulin secretion Effects 0.000 description 5
• 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 description 5
• 230000014759 maintenance of location Effects 0.000 description 5
• 208000011661 metabolic syndrome X Diseases 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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• JPWXZJKFWLMSKF-UHFFFAOYSA-N ethyl (E)-3-(2-bromo-4-hydroxyphenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=C(Br)C=C(O)C=C1 JPWXZJKFWLMSKF-UHFFFAOYSA-N 0.000 description 3
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