PT1852433E - Derivados de carbazole, seus solvatos ou seus sais farmaceuticamente aceitáveis - Google Patents

Info

Publication number

PT1852433E

PT1852433E PT05799893T PT05799893T PT1852433E PT 1852433 E PT1852433 E PT 1852433E PT 05799893 T PT05799893 T PT 05799893T PT 05799893 T PT05799893 T PT 05799893T PT 1852433 E PT1852433 E PT 1852433E

Authority

PT

Portugal

Prior art keywords

group

methoxy

substituent

groups

methyl

Prior art date

2004-10-29

Links

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• 150000003839 salts Chemical class 0.000 title claims abstract description 98
• 239000012453 solvate Substances 0.000 title claims abstract description 77
• 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 236
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 72
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 55
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 40
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 37
• 239000003814 drug Substances 0.000 claims abstract description 35
• 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims abstract description 29
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 29
• 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims abstract description 28
• 230000003449 preventive effect Effects 0.000 claims abstract description 24
• 229940124597 therapeutic agent Drugs 0.000 claims abstract description 24
• 206010019708 Hepatic steatosis Diseases 0.000 claims abstract description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 20
• 208000008589 Obesity Diseases 0.000 claims abstract description 19
• 235000020824 obesity Nutrition 0.000 claims abstract description 19
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 18
• 208000010706 fatty liver disease Diseases 0.000 claims abstract description 18
• 208000004930 Fatty Liver Diseases 0.000 claims abstract description 17
• 231100000240 steatosis hepatitis Toxicity 0.000 claims abstract description 17
• 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 16
• 206010020772 Hypertension Diseases 0.000 claims abstract description 16
• 230000005856 abnormality Effects 0.000 claims abstract description 16
• 230000037356 lipid metabolism Effects 0.000 claims abstract description 16
• 230000009278 visceral effect Effects 0.000 claims abstract description 16
• 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims abstract description 14
• 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims abstract description 4
• 125000001424 substituent group Chemical group 0.000 claims description 528
• -1 isoxazoyl group Chemical group 0.000 claims description 267
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 161
• 229910052736 halogen Inorganic materials 0.000 claims description 148
• 238000002360 preparation method Methods 0.000 claims description 132
• 125000005843 halogen group Chemical group 0.000 claims description 131
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 103
• 150000001716 carbazoles Chemical class 0.000 claims description 90
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 61
• 239000000203 mixture Substances 0.000 claims description 55
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 48
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 48
• 150000002367 halogens Chemical class 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 125000004076 pyridyl group Chemical group 0.000 claims description 35
• 125000002252 acyl group Chemical group 0.000 claims description 32
• 239000003795 chemical substances by application Substances 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 125000000732 arylene group Chemical group 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 24
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 23
• 125000004450 alkenylene group Chemical group 0.000 claims description 21
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 21
• 125000000335 thiazolyl group Chemical group 0.000 claims description 20
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 19
• 125000004419 alkynylene group Chemical group 0.000 claims description 19
• 125000002541 furyl group Chemical group 0.000 claims description 19
• 125000001544 thienyl group Chemical group 0.000 claims description 19
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 18
• 125000002947 alkylene group Chemical group 0.000 claims description 18
• 125000005724 cycloalkenylene group Chemical group 0.000 claims description 18
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 18
• 125000002971 oxazolyl group Chemical group 0.000 claims description 18
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 17
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 17
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 16
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 15
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 150000002430 hydrocarbons Chemical group 0.000 claims description 15
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 15
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 14
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 13
• 239000004480 active ingredient Substances 0.000 claims description 13
• 125000004414 alkyl thio group Chemical group 0.000 claims description 13
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 12
• JDJNTDWBSDINTJ-UHFFFAOYSA-N 2-[9-[[3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methyl]carbazol-4-yl]oxy-2-phenylacetic acid Chemical compound C=1C=C(OCC2=C(OC(=N2)C=2C=CC=CC=2)C)C(OC)=CC=1CN(C1=CC=C2)C3=CC=CC=C3C1=C2OC(C(O)=O)C1=CC=CC=C1 JDJNTDWBSDINTJ-UHFFFAOYSA-N 0.000 claims description 11
• 125000001931 aliphatic group Chemical group 0.000 claims description 11
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 11
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 11
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 10
• VIBPQOUIULLYPG-UHFFFAOYSA-N 4-[9-[[3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methyl]carbazol-4-yl]oxy-2-methylbutanoic acid Chemical compound COC1=CC(CN2C3=CC=CC(OCCC(C)C(O)=O)=C3C3=CC=CC=C32)=CC=C1OCC(=C(O1)C)N=C1C1=CC=CC=C1 VIBPQOUIULLYPG-UHFFFAOYSA-N 0.000 claims description 10
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
• 125000002785 azepinyl group Chemical group 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000001425 triazolyl group Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 6
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 6
• 229910052727 yttrium Inorganic materials 0.000 claims description 6
• IEZQWZJJSDXGOU-UHFFFAOYSA-N 2-[9-[[3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methyl]carbazol-4-yl]oxy-2-methylpropanoic acid Chemical compound COC1=CC(CN2C3=CC=CC(OC(C)(C)C(O)=O)=C3C3=CC=CC=C32)=CC=C1OCC(=C(O1)C)N=C1C1=CC=CC=C1 IEZQWZJJSDXGOU-UHFFFAOYSA-N 0.000 claims description 5
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 239000005711 Benzoic acid Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
• FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 5
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
• 235000010233 benzoic acid Nutrition 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• UFWWGUBJVVNZDH-UHFFFAOYSA-N 2-[9-[[3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methyl]carbazol-4-yl]oxypropanoic acid Chemical compound COC1=CC(CN2C3=CC=CC(OC(C)C(O)=O)=C3C3=CC=CC=C32)=CC=C1OCC(=C(O1)C)N=C1C1=CC=CC=C1 UFWWGUBJVVNZDH-UHFFFAOYSA-N 0.000 claims description 3
• YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical group CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
• 229940005605 valeric acid Drugs 0.000 claims description 3
• KDXZMVPUAGRSSK-UHFFFAOYSA-N 2-[9-[[3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methyl]carbazol-4-yl]oxybutanoic acid Chemical compound C12=CC=CC=C2C=2C(OC(CC)C(O)=O)=CC=CC=2N1CC(C=C1OC)=CC=C1OCC(=C(O1)C)N=C1C1=CC=CC=C1 KDXZMVPUAGRSSK-UHFFFAOYSA-N 0.000 claims description 2
• FRFSNUSKLVOAIM-UHFFFAOYSA-N 3-[9-[[3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methyl]carbazol-4-yl]oxy-2,2-dimethylpropanoic acid Chemical compound COC1=CC(CN2C3=CC=CC(OCC(C)(C)C(O)=O)=C3C3=CC=CC=C32)=CC=C1OCC(=C(O1)C)N=C1C1=CC=CC=C1 FRFSNUSKLVOAIM-UHFFFAOYSA-N 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• 239000003873 peroxisome proliferator activated receptor gamma antagonist Substances 0.000 claims description 2
• IJCYXYSHSJVRBP-UHFFFAOYSA-N 2-[9-[[3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methyl]carbazol-4-yl]oxyhexanoic acid Chemical compound C12=CC=CC=C2C=2C(OC(CCCC)C(O)=O)=CC=CC=2N1CC(C=C1OC)=CC=C1OCC(=C(O1)C)N=C1C1=CC=CC=C1 IJCYXYSHSJVRBP-UHFFFAOYSA-N 0.000 claims 1
• MNBLAYCWHVOHIF-UHFFFAOYSA-N 3-[9-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]-3-methoxyphenyl]methyl]carbazol-4-yl]oxy-2,2-dimethylpropanoic acid Chemical compound COC1=CC(CN2C3=CC=CC(OCC(C)(C)C(O)=O)=C3C3=CC=CC=C32)=CC=C1OCC(=C(O1)C)N=C1C1=CC=CO1 MNBLAYCWHVOHIF-UHFFFAOYSA-N 0.000 claims 1
• 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 1
• 229960002446 octanoic acid Drugs 0.000 claims 1
• 230000002218 hypoglycaemic effect Effects 0.000 abstract description 7
• 210000000577 adipose tissue Anatomy 0.000 abstract description 6
• 230000000055 hyoplipidemic effect Effects 0.000 abstract description 5
• 230000001603 reducing effect Effects 0.000 abstract description 4
• 201000005577 familial hyperlipidemia Diseases 0.000 abstract 1
• 201000009104 prediabetes syndrome Diseases 0.000 abstract 1
• 150000001875 compounds Chemical class 0.000 description 311
• 238000000034 method Methods 0.000 description 247
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
• 238000005160 1H NMR spectroscopy Methods 0.000 description 84
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 79
• 239000000243 solution Substances 0.000 description 74
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 68
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
• 239000002585 base Substances 0.000 description 58
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
• 239000012442 inert solvent Substances 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
• 230000000694 effects Effects 0.000 description 47
• 238000001914 filtration Methods 0.000 description 46
• 239000011541 reaction mixture Substances 0.000 description 44
• 238000001228 spectrum Methods 0.000 description 44
• 238000003756 stirring Methods 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 37
• 210000004027 cell Anatomy 0.000 description 35
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 31
• 239000002904 solvent Substances 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• 239000002244 precipitate Substances 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 239000000706 filtrate Substances 0.000 description 24
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• 229910052783 alkali metal Inorganic materials 0.000 description 22
• 239000013078 crystal Substances 0.000 description 22
• 238000003786 synthesis reaction Methods 0.000 description 22
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
• 239000013612 plasmid Substances 0.000 description 21
• 238000012360 testing method Methods 0.000 description 21
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
• 230000002829 reductive effect Effects 0.000 description 20
• 238000000926 separation method Methods 0.000 description 19
• 239000002253 acid Substances 0.000 description 18
• 239000012267 brine Substances 0.000 description 18
• 239000004615 ingredient Substances 0.000 description 18
• 230000003287 optical effect Effects 0.000 description 18
• 229910000027 potassium carbonate Inorganic materials 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 108020004414 DNA Proteins 0.000 description 17
• 239000003480 eluent Substances 0.000 description 17
• XKVMNJNFDRQAAM-UHFFFAOYSA-N 4-[[4-(chloromethyl)-2-methoxyphenoxy]methyl]-5-methyl-2-phenyl-1,3-oxazole Chemical compound COC1=CC(CCl)=CC=C1OCC1=C(C)OC(C=2C=CC=CC=2)=N1 XKVMNJNFDRQAAM-UHFFFAOYSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 16
• 229910000104 sodium hydride Inorganic materials 0.000 description 16
• 239000012312 sodium hydride Substances 0.000 description 16
• IUWAZTWHBAHWAU-UHFFFAOYSA-N 2-(9h-carbazol-4-yloxy)-2-methylpropanoic acid Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2OC(C)(C)C(O)=O IUWAZTWHBAHWAU-UHFFFAOYSA-N 0.000 description 15
• 239000005557 antagonist Substances 0.000 description 15
• 238000004128 high performance liquid chromatography Methods 0.000 description 15
• 229910052987 metal hydride Inorganic materials 0.000 description 15
• 150000004681 metal hydrides Chemical class 0.000 description 15
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
• 150000001408 amides Chemical class 0.000 description 14
• IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 14
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 12
• 150000002170 ethers Chemical class 0.000 description 12
• 229910052751 metal Inorganic materials 0.000 description 12
• 239000002184 metal Substances 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 238000007670 refining Methods 0.000 description 12
• 238000005406 washing Methods 0.000 description 12
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 11
• 150000001298 alcohols Chemical class 0.000 description 11
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 11
• 238000001514 detection method Methods 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
• 239000012634 fragment Substances 0.000 description 10
• 230000002401 inhibitory effect Effects 0.000 description 10
• 239000002609 medium Substances 0.000 description 10
• 230000035484 reaction time Effects 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
• 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 description 9
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
• 239000000556 agonist Substances 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 230000014509 gene expression Effects 0.000 description 9
• 230000036961 partial effect Effects 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 9
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
• 108010016731 PPAR gamma Proteins 0.000 description 8
• 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 8
• 210000001789 adipocyte Anatomy 0.000 description 8
• 150000001340 alkali metals Chemical class 0.000 description 8
• 150000004703 alkoxides Chemical class 0.000 description 8
• 230000037396 body weight Effects 0.000 description 8
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
• 229910000024 caesium carbonate Inorganic materials 0.000 description 8
• XIMFCGSNSKXPBO-RXMQYKEDSA-N ethyl (2r)-2-bromobutanoate Chemical compound CCOC(=O)[C@H](Br)CC XIMFCGSNSKXPBO-RXMQYKEDSA-N 0.000 description 8
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