JP5225984B2 - Ｆｘｒを調節する化合物及び方法 - Google Patents

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Publication number

JP5225984B2

JP5225984B2 JP2009512254A JP2009512254A JP5225984B2 JP 5225984 B2 JP5225984 B2 JP 5225984B2 JP 2009512254 A JP2009512254 A JP 2009512254A JP 2009512254 A JP2009512254 A JP 2009512254A JP 5225984 B2 JP5225984 B2 JP 5225984B2

Authority

JP

Japan

Prior art keywords

methyl

phenyl

hydrogen

isopropyl

alkyl

Prior art date

2006-05-24

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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• 150000001875 compounds Chemical class 0.000 title claims description 182
• 238000000034 method Methods 0.000 title description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 114
• 239000001257 hydrogen Substances 0.000 claims description 106
• -1 benzoisothiazolyl Chemical group 0.000 claims description 72
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 55
• 150000002431 hydrogen Chemical class 0.000 claims description 52
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 44
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 37
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• 125000001153 fluoro group Chemical group F* 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 18
• 125000001041 indolyl group Chemical group 0.000 claims description 18
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 17
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 12
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 10
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• POPANIGZHUWMKL-UHFFFAOYSA-N 4-[[4-[[3-(2,6-dichlorophenyl)-5-(trifluoromethyl)triazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methylbenzoic acid Chemical compound C=1C=C(OCC=2N(N=NC=2C(F)(F)F)C=2C(=CC=CC=2Cl)Cl)C=C(C)C=1N(C)CC1=CC=C(C(O)=O)C(C)=C1 POPANIGZHUWMKL-UHFFFAOYSA-N 0.000 claims description 3
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 5
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 5
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 5
• ZMQNWRIWGFMCQY-UHFFFAOYSA-N 3-[[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1N=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 ZMQNWRIWGFMCQY-UHFFFAOYSA-N 0.000 claims 1
• SFYBFUNJECIUDC-UHFFFAOYSA-N 3-[[4-[[3-(2-chloro-6-fluorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1N=NN(C=2C(=CC=CC=2F)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 SFYBFUNJECIUDC-UHFFFAOYSA-N 0.000 claims 1
• VXSPMOACFPKZRC-UHFFFAOYSA-N 3-[[n,2-dimethyl-4-[[5-propan-2-yl-3-[2-(trifluoromethoxy)phenyl]triazol-4-yl]methoxy]anilino]methyl]benzoic acid Chemical compound CC(C)C=1N=NN(C=2C(=CC=CC=2)OC(F)(F)F)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=CC(C(O)=O)=C1 VXSPMOACFPKZRC-UHFFFAOYSA-N 0.000 claims 1
• PBOQIQQEKMWEIF-UHFFFAOYSA-N 4-[[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]benzoic acid Chemical compound CC(C)C=1N=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC(C=C1C)=CC=C1N(C)CC1=CC=C(C(O)=O)C=C1 PBOQIQQEKMWEIF-UHFFFAOYSA-N 0.000 claims 1
• IJOWOXZRGNLVHF-UHFFFAOYSA-N 4-[[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)triazol-4-yl]methoxy]-n,2-dimethylanilino]methyl]-2-methylbenzoic acid Chemical compound C=1C=C(OCC=2N(N=NC=2C2CC2)C=2C(=CC=CC=2Cl)Cl)C=C(C)C=1N(C)CC1=CC=C(C(O)=O)C(C)=C1 IJOWOXZRGNLVHF-UHFFFAOYSA-N 0.000 claims 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 242
• 238000002360 preparation method Methods 0.000 description 143
• 239000000243 solution Substances 0.000 description 106
• 235000019439 ethyl acetate Nutrition 0.000 description 98
• 238000006243 chemical reaction Methods 0.000 description 96
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 94
• 239000011541 reaction mixture Substances 0.000 description 88
• 230000002829 reductive effect Effects 0.000 description 76
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
• 239000000203 mixture Substances 0.000 description 66
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
• 238000005160 1H NMR spectroscopy Methods 0.000 description 33
• 239000012044 organic layer Substances 0.000 description 33
• 239000012267 brine Substances 0.000 description 32
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 32
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
• 239000007787 solid Substances 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
• 239000010410 layer Substances 0.000 description 30
• 239000007858 starting material Substances 0.000 description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 238000003818 flash chromatography Methods 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 239000000460 chlorine Substances 0.000 description 17
• 238000004587 chromatography analysis Methods 0.000 description 17
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
• 235000012000 cholesterol Nutrition 0.000 description 16
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 208000032928 Dyslipidaemia Diseases 0.000 description 13
• 208000017170 Lipid metabolism disease Diseases 0.000 description 13
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• 239000012074 organic phase Substances 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
• 102100038495 Bile acid receptor Human genes 0.000 description 11
• 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 description 11
• IJVUIOCXNVEGKH-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methanol Chemical compound OCC1=C(C(C)C)N=NN1C1=C(Cl)C=CC=C1Cl IJVUIOCXNVEGKH-UHFFFAOYSA-N 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 239000000741 silica gel Substances 0.000 description 11
• 229910002027 silica gel Inorganic materials 0.000 description 11
• 239000005909 Kieselgur Substances 0.000 description 10
• 239000003153 chemical reaction reagent Substances 0.000 description 10
• 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 108010003814 member 2 group B nuclear receptor subfamily 0 Proteins 0.000 description 10
• 239000000377 silicon dioxide Substances 0.000 description 10
• 229910052938 sodium sulfate Inorganic materials 0.000 description 10
• 235000011152 sodium sulphate Nutrition 0.000 description 10
• 239000002904 solvent Substances 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
• 102100023172 Nuclear receptor subfamily 0 group B member 2 Human genes 0.000 description 9
• 229910004298 SiO 2 Inorganic materials 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 235000019341 magnesium sulphate Nutrition 0.000 description 8
• LHJKZERUIPGPCK-UHFFFAOYSA-N methyl 4-formyl-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1C LHJKZERUIPGPCK-UHFFFAOYSA-N 0.000 description 8
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
• TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 8
• 108010010234 HDL Lipoproteins Proteins 0.000 description 7
• 102000015779 HDL Lipoproteins Human genes 0.000 description 7
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 6
• 229960000583 acetic acid Drugs 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 6
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 6
• 150000002632 lipids Chemical class 0.000 description 6
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 6
• HJMZTUQYJYZXAE-UHFFFAOYSA-N 1-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-2-methylphenyl]ethanone Chemical compound CC(C)C=1N=NN(C=2C(=CC=CC=2Cl)Cl)C=1COC1=CC=C(C(C)=O)C(C)=C1 HJMZTUQYJYZXAE-UHFFFAOYSA-N 0.000 description 5
• BYRWOSJFHWKXET-UHFFFAOYSA-N 2-azido-1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=[N+]=[N-] BYRWOSJFHWKXET-UHFFFAOYSA-N 0.000 description 5
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
• 239000012298 atmosphere Substances 0.000 description 5
• 229910000024 caesium carbonate Inorganic materials 0.000 description 5
• 229910002091 carbon monoxide Inorganic materials 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 108020004999 messenger RNA Proteins 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• 108090000623 proteins and genes Proteins 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 150000003626 triacylglycerols Chemical class 0.000 description 5
• GPOQODYGMUTOQL-UHFFFAOYSA-N 4-bromo-3-methylphenol Chemical compound CC1=CC(O)=CC=C1Br GPOQODYGMUTOQL-UHFFFAOYSA-N 0.000 description 4
• 239000005711 Benzoic acid Substances 0.000 description 4
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
• 108010062497 VLDL Lipoproteins Proteins 0.000 description 4
• 238000003556 assay Methods 0.000 description 4
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
• 238000004440 column chromatography Methods 0.000 description 4
• 238000001514 detection method Methods 0.000 description 4
• 238000010828 elution Methods 0.000 description 4
• DQDPZIRMUJBHTI-UHFFFAOYSA-N ethyl 3-(2,6-dichlorophenyl)-5-propan-2-yltriazole-4-carboxylate Chemical compound CCOC(=O)C1=C(C(C)C)N=NN1C1=C(Cl)C=CC=C1Cl DQDPZIRMUJBHTI-UHFFFAOYSA-N 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• KJKMOADDOGZYQC-UHFFFAOYSA-N methyl 2-(2-trimethylsilylethynyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C#C[Si](C)(C)C KJKMOADDOGZYQC-UHFFFAOYSA-N 0.000 description 4
• SFDVDNLBYGHFNF-UHFFFAOYSA-N methyl 6-bromo-1-benzothiophene-2-carboxylate Chemical compound C1=C(Br)C=C2SC(C(=O)OC)=CC2=C1 SFDVDNLBYGHFNF-UHFFFAOYSA-N 0.000 description 4
• SKZJYJMYLUQJPG-UHFFFAOYSA-N methyl 6-bromo-1h-indole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OC)=CNC2=C1 SKZJYJMYLUQJPG-UHFFFAOYSA-N 0.000 description 4
• 150000004702 methyl esters Chemical class 0.000 description 4
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
• 229920000728 polyester Polymers 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• 239000002002 slurry Substances 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 235000010288 sodium nitrite Nutrition 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 4
• 229920002554 vinyl polymer Polymers 0.000 description 4
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• PSUKHRXMLRWKQF-UHFFFAOYSA-N methyl 2-methyl-4-[[methyl-[2-methyl-6-[[5-propan-2-yl-3-[2-(trifluoromethoxy)phenyl]triazol-4-yl]methoxy]pyridin-3-yl]amino]methyl]benzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C(C(=N1)C)=CC=C1OCC1=C(C(C)C)N=NN1C1=CC=CC=C1OC(F)(F)F PSUKHRXMLRWKQF-UHFFFAOYSA-N 0.000 description 2
• ULUMAACGWLZNHF-UHFFFAOYSA-N methyl 4-(2-amino-4-methoxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)C=C1N ULUMAACGWLZNHF-UHFFFAOYSA-N 0.000 description 2
• SJVMXEXEYBEEHK-UHFFFAOYSA-N methyl 4-(2-bromo-4-methoxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)C=C1Br SJVMXEXEYBEEHK-UHFFFAOYSA-N 0.000 description 2
• JTOJTFMOZMCZKU-UHFFFAOYSA-N methyl 4-(bromomethyl)-2-butoxybenzoate Chemical compound CCCCOC1=CC(CBr)=CC=C1C(=O)OC JTOJTFMOZMCZKU-UHFFFAOYSA-N 0.000 description 2
• DSCDSFHUSZSPLM-UHFFFAOYSA-N methyl 4-(hydroxymethyl)-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(CO)C=C1C DSCDSFHUSZSPLM-UHFFFAOYSA-N 0.000 description 2
• GNEADNFRBXZVDG-UHFFFAOYSA-N methyl 4-[(2-fluoro-4-hydroxyanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CNC1=CC=C(O)C=C1F GNEADNFRBXZVDG-UHFFFAOYSA-N 0.000 description 2
• YRTRIWWUUJJESV-UHFFFAOYSA-N methyl 4-[(4-hydroxy-2-methylanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CNC1=CC=C(O)C=C1C YRTRIWWUUJJESV-UHFFFAOYSA-N 0.000 description 2
• PZNMWPYPPPVNFI-UHFFFAOYSA-N methyl 4-[[(4-hydroxy-2-methylphenyl)methylamino]methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CNCC1=CC=C(O)C=C1C PZNMWPYPPPVNFI-UHFFFAOYSA-N 0.000 description 2
• IFAGJPMFLGAPAX-UHFFFAOYSA-N methyl 4-[[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-2-methylphenyl]methylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NCC(C(=C1)C)=CC=C1OCC1=C(C(C)C)N=NN1C1=C(Cl)C=CC=C1Cl IFAGJPMFLGAPAX-UHFFFAOYSA-N 0.000 description 2
• JPGRSTBIEYGVNO-UHFFFAOYSA-N methyl 4-ethynylbenzoate Chemical compound COC(=O)C1=CC=C(C#C)C=C1 JPGRSTBIEYGVNO-UHFFFAOYSA-N 0.000 description 2
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• MFOKOKHNSVUKON-UHFFFAOYSA-N methyl 5-bromo-1H-indole-3-carboxylate Natural products C1=C(Br)C=C2C(C(=O)OC)=CNC2=C1 MFOKOKHNSVUKON-UHFFFAOYSA-N 0.000 description 2
• UYFFMVDJHCONSM-UHFFFAOYSA-N methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)triazole-4-carboxylate Chemical compound COC(=O)C1=C(C2CC2)N=NN1C1=C(Cl)C=CC=C1Cl UYFFMVDJHCONSM-UHFFFAOYSA-N 0.000 description 2
• MOOHLFRSZUFCOU-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-benzothiophene-2-carboxylate Chemical compound C1=C2SC(C(=O)OC)=CC2=CC=C1C1=CC=C(O)C=C1C MOOHLFRSZUFCOU-UHFFFAOYSA-N 0.000 description 2
• NRTWWGSSWOLVHM-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-methylindole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CN(C)C2=CC=1C1=CC=C(O)C=C1C NRTWWGSSWOLVHM-UHFFFAOYSA-N 0.000 description 2
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• RLMWPNDSVWJWHA-UHFFFAOYSA-N methyl 6-bromo-1-methylindole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OC)=CN(C)C2=C1 RLMWPNDSVWJWHA-UHFFFAOYSA-N 0.000 description 2
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
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• 239000012071 phase Substances 0.000 description 2
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 230000003389 potentiating effect Effects 0.000 description 2
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• 230000004044 response Effects 0.000 description 2
• 101150096065 shp gene Proteins 0.000 description 2
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• 239000011537 solubilization buffer Substances 0.000 description 2
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• 238000003756 stirring Methods 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
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• 238000010998 test method Methods 0.000 description 2
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
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• 230000035897 transcription Effects 0.000 description 2
• 238000013518 transcription Methods 0.000 description 2
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• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
• UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
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• IHXVDUQOHZEJLU-UHFFFAOYSA-N methyl 3-[2-(4-hydroxy-2-methylphenyl)ethenyl]benzoate Chemical compound COC(=O)C1=CC=CC(C=CC=2C(=CC(O)=CC=2)C)=C1 IHXVDUQOHZEJLU-UHFFFAOYSA-N 0.000 description 1
• KRJAOEXWUPZOIN-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]phenyl]ethenyl]benzoate Chemical compound COC(=O)C1=CC=CC(C=CC=2C(=CC(OCC=3N(N=NC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)Cl)=C1 KRJAOEXWUPZOIN-UHFFFAOYSA-N 0.000 description 1
• WNTBYMVGZOFWLF-UHFFFAOYSA-N methyl 3-[2-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-2-methylphenyl]propan-2-ylsulfanyl]benzoate Chemical compound COC(=O)C1=CC=CC(SC(C)(C)C=2C(=CC(OCC=3N(N=NC=3C(C)C)C=3C(=CC=CC=3Cl)Cl)=CC=2)C)=C1 WNTBYMVGZOFWLF-UHFFFAOYSA-N 0.000 description 1
• MBKUHNGECMPIHH-UHFFFAOYSA-N methyl 3-ethenylbenzoate Chemical compound COC(=O)C1=CC=CC(C=C)=C1 MBKUHNGECMPIHH-UHFFFAOYSA-N 0.000 description 1
• DDXZMLZQQWVSRX-UHFFFAOYSA-N methyl 3-ethynylbenzoate Chemical compound COC(=O)C1=CC=CC(C#C)=C1 DDXZMLZQQWVSRX-UHFFFAOYSA-N 0.000 description 1
• SRGOMBXXNIVIPR-UHFFFAOYSA-N methyl 3-sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC(S)=C1 SRGOMBXXNIVIPR-UHFFFAOYSA-N 0.000 description 1
• MBEOKSAQLBKHSD-UHFFFAOYSA-N methyl 4-(2-bromo-4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1Br MBEOKSAQLBKHSD-UHFFFAOYSA-N 0.000 description 1
• CSALCOFYVWMQBG-UHFFFAOYSA-N methyl 4-(2-chloro-4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1Cl CSALCOFYVWMQBG-UHFFFAOYSA-N 0.000 description 1
• RAEVMJRGBGCZIM-UHFFFAOYSA-N methyl 4-(2-fluoro-4-hydroxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1F RAEVMJRGBGCZIM-UHFFFAOYSA-N 0.000 description 1
• FWGOAHUFSIVCPG-UHFFFAOYSA-N methyl 4-(4-hydroxy-2-nitrophenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1[N+]([O-])=O FWGOAHUFSIVCPG-UHFFFAOYSA-N 0.000 description 1
• JGNBKQHCVAPTTM-UHFFFAOYSA-N methyl 4-(4-hydroxy-3-methylphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C(C)=C1 JGNBKQHCVAPTTM-UHFFFAOYSA-N 0.000 description 1
• TYXOWTXOSOIMSE-UHFFFAOYSA-N methyl 4-(4-methoxy-2-nitrophenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)C=C1[N+]([O-])=O TYXOWTXOSOIMSE-UHFFFAOYSA-N 0.000 description 1
• NLWBJPPMPLPZIE-UHFFFAOYSA-N methyl 4-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C=C1 NLWBJPPMPLPZIE-UHFFFAOYSA-N 0.000 description 1
• WXCLPAPFMVVTOX-UHFFFAOYSA-N methyl 4-[(2-fluoro-4-hydroxy-n-methylanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1F WXCLPAPFMVVTOX-UHFFFAOYSA-N 0.000 description 1
• WEKDWRRJMSBWOK-UHFFFAOYSA-N methyl 4-[(4-hydroxy-2-methylphenyl)methylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NCC1=CC=C(O)C=C1C WEKDWRRJMSBWOK-UHFFFAOYSA-N 0.000 description 1
• UUDJXADZYZXWPC-UHFFFAOYSA-N methyl 4-[(4-hydroxy-n,2-dimethylanilino)methyl]-2-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1C UUDJXADZYZXWPC-UHFFFAOYSA-N 0.000 description 1
• ARFIARSKKJAKGN-UHFFFAOYSA-N methyl 4-[(4-hydroxy-n,2-dimethylanilino)methyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1C ARFIARSKKJAKGN-UHFFFAOYSA-N 0.000 description 1
• PEJFTMUXOSWNSS-UHFFFAOYSA-N methyl 4-[(4-hydroxy-n,2-dimethylanilino)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN(C)C1=CC=C(O)C=C1C PEJFTMUXOSWNSS-UHFFFAOYSA-N 0.000 description 1
• OIBLKVANAWUALU-UHFFFAOYSA-N methyl 4-[2-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-2-methylphenyl]ethynyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C#CC(C(=C1)C)=CC=C1OCC1=C(C(C)C)N=NN1C1=C(Cl)C=CC=C1Cl OIBLKVANAWUALU-UHFFFAOYSA-N 0.000 description 1
• UMSXTNGWLSOTFI-UHFFFAOYSA-N methyl 4-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yltriazol-4-yl]methoxy]-2-methylphenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(C(=C1)C)=CC=C1OCC1=C(C(C)C)N=NN1C1=C(Cl)C=CC=C1Cl UMSXTNGWLSOTFI-UHFFFAOYSA-N 0.000 description 1
• WQIOUBBFTOIXBD-UHFFFAOYSA-N methyl 4-[4-hydroxy-2-(trifluoromethyl)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C(F)(F)F WQIOUBBFTOIXBD-UHFFFAOYSA-N 0.000 description 1
• CGGGWRDRBMSXOL-UHFFFAOYSA-N methyl 4-formyl-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1C(F)(F)F CGGGWRDRBMSXOL-UHFFFAOYSA-N 0.000 description 1
• BTZOMWXSWVOOHG-UHFFFAOYSA-N methyl 4-sulfanylbenzoate Chemical compound COC(=O)C1=CC=C(S)C=C1 BTZOMWXSWVOOHG-UHFFFAOYSA-N 0.000 description 1
• LIQIPOFQWQLBCQ-UHFFFAOYSA-N methyl 5-(4-hydroxy-2-methylphenyl)thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C1=CC=C(O)C=C1C LIQIPOFQWQLBCQ-UHFFFAOYSA-N 0.000 description 1
• MSCOMZNDKVOGGI-UHFFFAOYSA-N methyl 5-(4-hydroxyphenyl)thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C1=CC=C(O)C=C1 MSCOMZNDKVOGGI-UHFFFAOYSA-N 0.000 description 1
• AALWVKQRLXHHRT-UHFFFAOYSA-N methyl 5-(4-methoxy-2-methylphenyl)-4-methylthiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C)=C1C1=CC=C(OC)C=C1C AALWVKQRLXHHRT-UHFFFAOYSA-N 0.000 description 1
• RJWZFHRMQRWEIH-UHFFFAOYSA-N methyl 5-bromo-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C1=CC(C)=C(Br)S1 RJWZFHRMQRWEIH-UHFFFAOYSA-N 0.000 description 1
• INSNZBHWOMPOKH-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-benzothiophene-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CSC2=CC=1C1=CC=C(O)C=C1C INSNZBHWOMPOKH-UHFFFAOYSA-N 0.000 description 1
• SKWDVGYXADERFY-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-propan-2-ylindazole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=NN(C(C)C)C2=CC=1C1=CC=C(O)C=C1C SKWDVGYXADERFY-UHFFFAOYSA-N 0.000 description 1
• XXEWKZYLPOJIIL-UHFFFAOYSA-N methyl 6-(4-hydroxy-2-methylphenyl)-1-propan-2-ylindole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CN(C(C)C)C2=CC=1C1=CC=C(O)C=C1C XXEWKZYLPOJIIL-UHFFFAOYSA-N 0.000 description 1
• UVTAKNMJKKEKED-UHFFFAOYSA-N methyl 6-[4-[[3-(2,6-dichlorophenyl)-5-(trifluoromethyl)triazol-4-yl]methoxy]-2-methylphenyl]-1-benzothiophene-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CSC2=CC=1C(C(=C1)C)=CC=C1OCC1=C(C(F)(F)F)N=NN1C1=C(Cl)C=CC=C1Cl UVTAKNMJKKEKED-UHFFFAOYSA-N 0.000 description 1
• LFFOXNXUGCBVHQ-UHFFFAOYSA-N methyl 6-[4-[[3-(2,6-dichlorophenyl)-5-(trifluoromethyl)triazol-4-yl]methoxy]-2-methylphenyl]-1-propan-2-ylindazole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=NN(C(C)C)C2=CC=1C(C(=C1)C)=CC=C1OCC1=C(C(F)(F)F)N=NN1C1=C(Cl)C=CC=C1Cl LFFOXNXUGCBVHQ-UHFFFAOYSA-N 0.000 description 1
• ZAYPHRFENZHLAG-UHFFFAOYSA-N methyl 6-[4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)triazol-4-yl]methoxy]-2-methylphenyl]-1-propan-2-ylindazole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=NN(C(C)C)C2=CC=1C(C(=C1)C)=CC=C1OCC1=C(C2CC2)N=NN1C1=C(Cl)C=CC=C1Cl ZAYPHRFENZHLAG-UHFFFAOYSA-N 0.000 description 1
• RUBYSVHZXJRNLS-UHFFFAOYSA-N methyl 6-bromo-1-propan-2-ylindazole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OC)=NN(C(C)C)C2=C1 RUBYSVHZXJRNLS-UHFFFAOYSA-N 0.000 description 1
• HVSAEJIBGMVUJK-UHFFFAOYSA-N methyl 6-bromo-1-propan-2-ylindole-3-carboxylate Chemical compound BrC1=CC=C2C(C(=O)OC)=CN(C(C)C)C2=C1 HVSAEJIBGMVUJK-UHFFFAOYSA-N 0.000 description 1
• ZTRAEMILTFNZSM-UHFFFAOYSA-N methyl thiophene-3-carboxylate Chemical compound COC(=O)C=1C=CSC=1 ZTRAEMILTFNZSM-UHFFFAOYSA-N 0.000 description 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• OQJBFFCUFALWQL-UHFFFAOYSA-N n-(piperidine-1-carbonylimino)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)N=NC(=O)N1CCCCC1 OQJBFFCUFALWQL-UHFFFAOYSA-N 0.000 description 1
• FTTNHUULIMOCKS-WAYWQWQTSA-N n-[(z)-3-acetamidobut-2-en-2-yl]acetamide Chemical compound CC(=O)N\C(C)=C(\C)NC(C)=O FTTNHUULIMOCKS-WAYWQWQTSA-N 0.000 description 1
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• 231100000252 nontoxic Toxicity 0.000 description 1
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• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
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• CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical class [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 description 1
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• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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