TW200523249A - Novel heteroaryl derivative - Google Patents

Info

Publication number

TW200523249A

TW200523249A TW093121149A TW93121149A TW200523249A TW 200523249 A TW200523249 A TW 200523249A TW 093121149 A TW093121149 A TW 093121149A TW 93121149 A TW93121149 A TW 93121149A TW 200523249 A TW200523249 A TW 200523249A

Authority

TW

Taiwan

Prior art keywords

group

substituted

heteroaryl

mmol

ring

Prior art date

2003-07-15

Links

• Espacenet
• Global Dossier
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• 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 89
• 150000003839 salts Chemical class 0.000 claims abstract description 59
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 45
• 229940002612 prodrug Drugs 0.000 claims abstract description 39
• 239000000651 prodrug Substances 0.000 claims abstract description 39
• 125000003118 aryl group Chemical group 0.000 claims abstract description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
• 125000000732 arylene group Chemical group 0.000 claims abstract description 5
• -1 heteroaryl compound Chemical class 0.000 claims description 213
• 150000001875 compounds Chemical class 0.000 claims description 197
• 238000000034 method Methods 0.000 claims description 119
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• 125000003107 substituted aryl group Chemical group 0.000 claims description 10
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
• 239000005977 Ethylene Substances 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 150000003233 pyrroles Chemical group 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 5
• 150000002473 indoazoles Chemical group 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 150000003852 triazoles Chemical group 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• 125000005567 fluorenylene group Chemical group 0.000 claims 3
• 125000002883 imidazolyl group Chemical group 0.000 claims 2
• 230000000979 retarding effect Effects 0.000 claims 2
• JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 claims 1
• 150000001336 alkenes Chemical class 0.000 claims 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
• 150000003937 benzamidines Chemical class 0.000 claims 1
• 150000001555 benzenes Chemical class 0.000 claims 1
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 239000001273 butane Substances 0.000 claims 1
• 230000000747 cardiac effect Effects 0.000 claims 1
• 239000011248 coating agent Substances 0.000 claims 1
• 238000000576 coating method Methods 0.000 claims 1
• 239000000571 coke Substances 0.000 claims 1
• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
• IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
• 125000005156 substituted alkylene group Chemical group 0.000 claims 1
• 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• 125000004450 alkenylene group Chemical group 0.000 abstract description 4
• 125000005549 heteroarylene group Chemical group 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 220
• 239000000243 solution Substances 0.000 description 166
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 97
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 96
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 95
• 239000002904 solvent Substances 0.000 description 89
• 238000006243 chemical reaction Methods 0.000 description 86
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 83
• 238000005481 NMR spectroscopy Methods 0.000 description 82
• 239000012044 organic layer Substances 0.000 description 71
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 66
• 239000000203 mixture Substances 0.000 description 63
• 101150041968 CDC13 gene Proteins 0.000 description 62
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 52
• 238000003756 stirring Methods 0.000 description 50
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 235000002639 sodium chloride Nutrition 0.000 description 44
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 42
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• 238000010898 silica gel chromatography Methods 0.000 description 31
• 239000002585 base Substances 0.000 description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 28
• 238000001816 cooling Methods 0.000 description 23
• 239000007788 liquid Substances 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 235000019341 magnesium sulphate Nutrition 0.000 description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• 239000007864 aqueous solution Substances 0.000 description 20
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 20
• 235000019260 propionic acid Nutrition 0.000 description 20
• 230000000694 effects Effects 0.000 description 19
• 239000002253 acid Substances 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• 239000010410 layer Substances 0.000 description 17
• 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 15
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 125000003277 amino group Chemical group 0.000 description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
• 206010012601 diabetes mellitus Diseases 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
• 238000012360 testing method Methods 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
• 239000000556 agonist Substances 0.000 description 11
• 238000009835 boiling Methods 0.000 description 11
• 238000004519 manufacturing process Methods 0.000 description 11
• 239000012312 sodium hydride Substances 0.000 description 11
• 229910000104 sodium hydride Inorganic materials 0.000 description 11
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• 239000000460 chlorine Substances 0.000 description 10
• 229910052801 chlorine Inorganic materials 0.000 description 10
• 239000013078 crystal Substances 0.000 description 10
• 239000007789 gas Substances 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
• 239000008280 blood Substances 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• 239000003814 drug Substances 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 229910052757 nitrogen Inorganic materials 0.000 description 9
• 239000002689 soil Substances 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• FKXMWPFESIFWMS-UHFFFAOYSA-N (4-methylphenyl)methanone Chemical compound CC1=CC=C([C+]=O)C=C1 FKXMWPFESIFWMS-UHFFFAOYSA-N 0.000 description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
• 101150014691 PPARA gene Proteins 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
• 230000002378 acidificating effect Effects 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 210000004369 blood Anatomy 0.000 description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
• 238000000605 extraction Methods 0.000 description 8
• 239000011737 fluorine Substances 0.000 description 8
• 229910052731 fluorine Inorganic materials 0.000 description 8
• 230000003287 optical effect Effects 0.000 description 8
• 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
• RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 7
• 238000004458 analytical method Methods 0.000 description 7
• 125000000623 heterocyclic group Chemical group 0.000 description 7
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 7
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
• NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
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• 230000004913 activation Effects 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 229940057995 liquid paraffin Drugs 0.000 description 6
• 229910052751 metal Inorganic materials 0.000 description 6
• 239000002184 metal Substances 0.000 description 6
• 229940017219 methyl propionate Drugs 0.000 description 6
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
• 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 6
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 6
• ZPCJPJQUVRIILS-UHFFFAOYSA-N 1-bromo-3-(bromomethyl)benzene Chemical compound BrCC1=CC=CC(Br)=C1 ZPCJPJQUVRIILS-UHFFFAOYSA-N 0.000 description 5
• 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 5
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• 125000002757 morpholinyl group Chemical group 0.000 description 5
• 210000002706 plastid Anatomy 0.000 description 5
• 238000000926 separation method Methods 0.000 description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 5
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
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• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 4
• 238000005160 1H NMR spectroscopy Methods 0.000 description 4
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• BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 4
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 4
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• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• 239000005456 alcohol based solvent Substances 0.000 description 4
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
• 230000003178 anti-diabetic effect Effects 0.000 description 4
• 239000000010 aprotic solvent Substances 0.000 description 4
• 239000003125 aqueous solvent Substances 0.000 description 4
• 125000004104 aryloxy group Chemical group 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• 125000005997 bromomethyl group Chemical group 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
• 210000004027 cell Anatomy 0.000 description 4
• 238000004891 communication Methods 0.000 description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 125000004494 ethyl ester group Chemical group 0.000 description 4
• 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 4
• 229910052736 halogen Inorganic materials 0.000 description 4
• 150000002367 halogens Chemical class 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• 150000002475 indoles Chemical class 0.000 description 4
• 239000012442 inert solvent Substances 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000003446 ligand Substances 0.000 description 4
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