NO800709L - Analogifremgangsmaate for fremstilling av farmakologisk aktive indolderivater - Google Patents

Info

Publication number

NO800709L

NO800709L NO800709A NO800709A NO800709L NO 800709 L NO800709 L NO 800709L NO 800709 A NO800709 A NO 800709A NO 800709 A NO800709 A NO 800709A NO 800709 L NO800709 L NO 800709L

Authority

NO

Norway

Prior art keywords

methyl

group

indol

propanoic acid

yloxy

Prior art date

1979-03-13

Links

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• Global Dossier
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• 238000002360 preparation method Methods 0.000 title claims description 12
• 238000000034 method Methods 0.000 title claims description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 49
• 150000003839 salts Chemical class 0.000 claims abstract description 13
• 150000002475 indoles Chemical class 0.000 claims abstract description 11
• JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 claims abstract description 7
• 229940054051 antipsychotic indole derivative Drugs 0.000 claims abstract description 4
• -1 methoxy, amino Chemical group 0.000 claims description 115
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
• 125000004432 carbon atom Chemical group C* 0.000 claims description 39
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• LBOICXLDDQGHNA-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-1,2-dimethylindol-5-yl]oxy-2-methylpropanoic acid Chemical compound C12=CC(OC(C)(C)C(O)=O)=CC=C2N(C)C(C)=C1C1=CC=C(Cl)C=C1 LBOICXLDDQGHNA-UHFFFAOYSA-N 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 9
• 239000002585 base Substances 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 239000007858 starting material Substances 0.000 claims description 7
• 150000001447 alkali salts Chemical class 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 230000007062 hydrolysis Effects 0.000 claims description 6
• 238000006460 hydrolysis reaction Methods 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 150000007522 mineralic acids Chemical class 0.000 claims description 6
• 150000007524 organic acids Chemical class 0.000 claims description 6
• 235000005985 organic acids Nutrition 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 239000011541 reaction mixture Substances 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• 150000007529 inorganic bases Chemical class 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000002560 nitrile group Chemical group 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 230000000269 nucleophilic effect Effects 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• YNUOXVUFIXKSSY-UHFFFAOYSA-N 2-methyl-2-(2-methyl-1-propyl-3-pyridin-4-ylindol-5-yl)oxypropanoic acid Chemical compound C12=CC(OC(C)(C)C(O)=O)=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 YNUOXVUFIXKSSY-UHFFFAOYSA-N 0.000 claims description 3
• 230000021736 acetylation Effects 0.000 claims description 3
• 238000006640 acetylation reaction Methods 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 230000009435 amidation Effects 0.000 claims description 3
• 238000007112 amidation reaction Methods 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 230000032050 esterification Effects 0.000 claims description 3
• 238000005886 esterification reaction Methods 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
• 230000003647 oxidation Effects 0.000 claims description 3
• 238000007254 oxidation reaction Methods 0.000 claims description 3
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
• 125000005493 quinolyl group Chemical group 0.000 claims description 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
• FHMHWGULPLQNAJ-UHFFFAOYSA-N 1H-indole iron Chemical group N1C=CC2=CC=CC=C12.[Fe] FHMHWGULPLQNAJ-UHFFFAOYSA-N 0.000 claims 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 1
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
• 125000000542 sulfonic acid group Chemical group 0.000 claims 1
• 230000029936 alkylation Effects 0.000 abstract description 8
• 238000005804 alkylation reaction Methods 0.000 abstract description 8
• 230000000144 pharmacologic effect Effects 0.000 abstract description 4
• 230000000879 anti-atherosclerotic effect Effects 0.000 abstract 1
• 150000002632 lipids Chemical class 0.000 abstract 1
• 231100000252 nontoxic Toxicity 0.000 abstract 1
• 230000003000 nontoxic effect Effects 0.000 abstract 1
• 238000002844 melting Methods 0.000 description 154
• 230000008018 melting Effects 0.000 description 154
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
• IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 64
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 49
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
• 239000002904 solvent Substances 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
• 239000000741 silica gel Substances 0.000 description 26
• 229910002027 silica gel Inorganic materials 0.000 description 26
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• 238000001704 evaporation Methods 0.000 description 21
• 230000008020 evaporation Effects 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
• 239000000460 chlorine Substances 0.000 description 15
• 239000000243 solution Substances 0.000 description 14
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 238000001816 cooling Methods 0.000 description 11
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 239000003480 eluent Substances 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 238000009835 boiling Methods 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• PAGSNSUGVLTLEL-UHFFFAOYSA-N 3-(4-chlorophenyl)-1,2-dimethylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=C(Cl)C=C1 PAGSNSUGVLTLEL-UHFFFAOYSA-N 0.000 description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 238000000605 extraction Methods 0.000 description 8
• 239000012362 glacial acetic acid Substances 0.000 description 8
• YGGYDZSFDZQAEA-UHFFFAOYSA-N hydron;2-methyl-2-(2-methyl-1-propyl-3-pyridin-4-ylindol-5-yl)oxypropanoic acid;chloride Chemical compound Cl.C12=CC(OC(C)(C)C(O)=O)=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 YGGYDZSFDZQAEA-UHFFFAOYSA-N 0.000 description 8
• 238000005903 acid hydrolysis reaction Methods 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 235000011121 sodium hydroxide Nutrition 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• YWJPQGOILATFMU-UHFFFAOYSA-N 2-phenylmethoxy-1h-indole Chemical compound C=1C2=CC=CC=C2NC=1OCC1=CC=CC=C1 YWJPQGOILATFMU-UHFFFAOYSA-N 0.000 description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 239000000203 mixture Substances 0.000 description 5
• 239000003208 petroleum Substances 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 241000699670 Mus sp. Species 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
• 125000001309 chloro group Chemical group Cl* 0.000 description 4
• 239000002026 chloroform extract Substances 0.000 description 4
• 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 4
• 238000004440 column chromatography Methods 0.000 description 4
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
• 238000006264 debenzylation reaction Methods 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 125000004494 ethyl ester group Chemical group 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 229940093915 gynecological organic acid Drugs 0.000 description 4
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 229940032007 methylethyl ketone Drugs 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
• PYOWATYEESVLHY-UHFFFAOYSA-N 2-methyl-1-propyl-3-pyridin-4-ylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 PYOWATYEESVLHY-UHFFFAOYSA-N 0.000 description 3
• OGEHFPXHFYRWLR-UHFFFAOYSA-N 3-(3-chlorophenyl)-1,2-dimethylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=CC(Cl)=C1 OGEHFPXHFYRWLR-UHFFFAOYSA-N 0.000 description 3
• CTGYFFRTMHCKDN-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-methyl-1-propylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1C1=CC=C(OC)C=C1 CTGYFFRTMHCKDN-UHFFFAOYSA-N 0.000 description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• MSEHINRRCQBFOV-UHFFFAOYSA-N ethyl 2-[2-(4-acetamidophenyl)-1-propylindol-6-yl]oxy-2-methylpropanoate Chemical compound C=1C2=CC=C(OC(C)(C)C(=O)OCC)C=C2N(CCC)C=1C1=CC=C(NC(C)=O)C=C1 MSEHINRRCQBFOV-UHFFFAOYSA-N 0.000 description 3
• ROELOVYKERVVSB-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)-1,2-dimethylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C)=C1C1=CC=C(Cl)C=C1 ROELOVYKERVVSB-UHFFFAOYSA-N 0.000 description 3
• VXPPNJWNSSQXSP-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methyl-1-propyl-3-pyridin-4-ylindol-5-yl)oxypropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 VXPPNJWNSSQXSP-UHFFFAOYSA-N 0.000 description 3
• 229910052731 fluorine Inorganic materials 0.000 description 3
• 239000011737 fluorine Substances 0.000 description 3
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 150000007530 organic bases Chemical group 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 2
• UNIUIPYMHVFQAV-UHFFFAOYSA-N 1,2-dimethyl-3-(2-phenylethyl)indol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1CCC1=CC=CC=C1 UNIUIPYMHVFQAV-UHFFFAOYSA-N 0.000 description 2
• WVNJZMPBOXMMGN-UHFFFAOYSA-N 1,2-dimethyl-3-(3-methylphenyl)indol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=CC(C)=C1 WVNJZMPBOXMMGN-UHFFFAOYSA-N 0.000 description 2
• SFVVSLQTXMAJAS-UHFFFAOYSA-N 1,2-dimethyl-3-(4-methylphenyl)indol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=C(C)C=C1 SFVVSLQTXMAJAS-UHFFFAOYSA-N 0.000 description 2
• XQFAWCDRMMHDGP-UHFFFAOYSA-N 1,2-dimethyl-3-[3-(trifluoromethyl)phenyl]indol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=CC(C(F)(F)F)=C1 XQFAWCDRMMHDGP-UHFFFAOYSA-N 0.000 description 2
• FLCVZVVSVTYSMQ-UHFFFAOYSA-N 1,2-dimethyl-3-phenylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=CC=C1 FLCVZVVSVTYSMQ-UHFFFAOYSA-N 0.000 description 2
• RNLPVRFYYZFSSO-UHFFFAOYSA-N 1,2-dimethyl-3-pyridin-2-ylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=CC=N1 RNLPVRFYYZFSSO-UHFFFAOYSA-N 0.000 description 2
• OWTFSRVYYBPULX-UHFFFAOYSA-N 1,2-dimethyl-3-pyridin-4-ylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=NC=C1 OWTFSRVYYBPULX-UHFFFAOYSA-N 0.000 description 2
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• 229940005561 1,4-benzoquinone Drugs 0.000 description 2
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• FPBRFKOCRCSCLP-UHFFFAOYSA-N ethyl 2-(1,2-dimethyl-3-pyridin-2-ylindol-5-yl)oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C)=C1C1=CC=CC=N1 FPBRFKOCRCSCLP-UHFFFAOYSA-N 0.000 description 1
• LKZMISLICVNFNC-UHFFFAOYSA-N ethyl 2-(1,3-dimethyl-2-pyridin-4-ylindol-5-yl)oxy-2-methylpropanoate Chemical compound CC=1C2=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C=1C1=CC=NC=C1 LKZMISLICVNFNC-UHFFFAOYSA-N 0.000 description 1
• BGMCYZCUWCXNOJ-UHFFFAOYSA-N ethyl 2-(1-ethyl-2-methyl-3-pyridin-4-ylindol-5-yl)oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CC)C(C)=C1C1=CC=NC=C1 BGMCYZCUWCXNOJ-UHFFFAOYSA-N 0.000 description 1
• PVSCGYFDYXIKCZ-UHFFFAOYSA-N ethyl 2-(2-benzyl-1-methyl-3-pyridin-4-ylindol-5-yl)oxy-2-methylpropanoate Chemical compound C=1C=NC=CC=1C=1C2=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C=1CC1=CC=CC=C1 PVSCGYFDYXIKCZ-UHFFFAOYSA-N 0.000 description 1
• IONBSIANSSYXEW-UHFFFAOYSA-N ethyl 2-(3,4-dibenzyl-1-propylindol-5-yl)oxy-2-methylpropanoate Chemical compound C12=C(CC=3C=CC=CC=3)C(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C=C1CC1=CC=CC=C1 IONBSIANSSYXEW-UHFFFAOYSA-N 0.000 description 1
• WGSXANVTRCHJTF-UHFFFAOYSA-N ethyl 2-[(2-benzyl-3-pyridin-4-yl-1h-indol-5-yl)oxy]-2-methylpropanoate Chemical compound C=1C=NC=CC=1C=1C2=CC(OC(C)(C)C(=O)OCC)=CC=C2NC=1CC1=CC=CC=C1 WGSXANVTRCHJTF-UHFFFAOYSA-N 0.000 description 1
• LKYBWWLNIIXCIU-UHFFFAOYSA-N ethyl 2-[1,2-dimethyl-3-(2-phenylethyl)indol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C)=C1CCC1=CC=CC=C1 LKYBWWLNIIXCIU-UHFFFAOYSA-N 0.000 description 1
• IMJKTPOTVIGOJP-UHFFFAOYSA-N ethyl 2-[1,2-dimethyl-3-(3-methylphenyl)indol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C)=C1C1=CC=CC(C)=C1 IMJKTPOTVIGOJP-UHFFFAOYSA-N 0.000 description 1
• IIFFJOWVTCFYRB-UHFFFAOYSA-N ethyl 2-[1,2-dimethyl-3-(4-methylphenyl)indol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C)=C1C1=CC=C(C)C=C1 IIFFJOWVTCFYRB-UHFFFAOYSA-N 0.000 description 1
• DZHWPQXZMFQLNO-UHFFFAOYSA-N ethyl 2-[2-(4-acetamidophenyl)-3-methyl-1-propylindol-5-yl]oxy-2-methylpropanoate Chemical compound CC=1C2=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C=1C1=CC=C(NC(C)=O)C=C1 DZHWPQXZMFQLNO-UHFFFAOYSA-N 0.000 description 1
• SJZKLDODRORURN-UHFFFAOYSA-N ethyl 2-[3-(4-fluorophenyl)-1,2-dimethylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C)=C1C1=CC=C(F)C=C1 SJZKLDODRORURN-UHFFFAOYSA-N 0.000 description 1
• WTVIPUNNGBQVDA-UHFFFAOYSA-N ethyl 2-[3-(4-fluorophenyl)-1-hexyl-2-methylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCCCCC)C(C)=C1C1=CC=C(F)C=C1 WTVIPUNNGBQVDA-UHFFFAOYSA-N 0.000 description 1
• SZFVKTYATXQCQJ-UHFFFAOYSA-N ethyl 2-[3-(4-methoxyphenyl)-1,2-dimethylindol-7-yl]oxy-2-methylpropanoate Chemical compound CC=1N(C)C=2C(OC(C)(C)C(=O)OCC)=CC=CC=2C=1C1=CC=C(OC)C=C1 SZFVKTYATXQCQJ-UHFFFAOYSA-N 0.000 description 1
• RGVXAOHXOCQURT-UHFFFAOYSA-N ethyl 2-[3-[2-(4-chlorophenyl)ethyl]-2-methyl-1-propylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1CCC1=CC=C(Cl)C=C1 RGVXAOHXOCQURT-UHFFFAOYSA-N 0.000 description 1
• LEQBTCBCFNUSEB-UHFFFAOYSA-N ethyl 2-[[3-(2-chlorophenyl)-2-methyl-1h-indol-5-yl]oxy]-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2NC(C)=C1C1=CC=CC=C1Cl LEQBTCBCFNUSEB-UHFFFAOYSA-N 0.000 description 1
• PTZPKSGWNLFCHA-UHFFFAOYSA-N ethyl 2-[[3-(4-methoxyphenyl)-2-methyl-1h-indol-5-yl]oxy]-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2NC(C)=C1C1=CC=C(OC)C=C1 PTZPKSGWNLFCHA-UHFFFAOYSA-N 0.000 description 1
• JSYYUJMHZQPACU-UHFFFAOYSA-N ethyl 2-[[3-[2-(4-chlorophenyl)ethyl]-2-methyl-1h-indol-5-yl]oxy]-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2NC(C)=C1CCC1=CC=C(Cl)C=C1 JSYYUJMHZQPACU-UHFFFAOYSA-N 0.000 description 1
• SBJQEHLYCQZDRB-UHFFFAOYSA-N ethyl 2-methyl-2-(1-methyl-2-propan-2-yl-3-pyridin-4-ylindol-5-yl)oxypropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C(C)C)=C1C1=CC=NC=C1 SBJQEHLYCQZDRB-UHFFFAOYSA-N 0.000 description 1
• BVGGKZCZGTYJGP-UHFFFAOYSA-N ethyl 2-methyl-2-(1-methyl-2-propyl-3-pyridin-4-ylindol-5-yl)oxypropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(CCC)=C1C1=CC=NC=C1 BVGGKZCZGTYJGP-UHFFFAOYSA-N 0.000 description 1
• TYFZKYVECDYBIX-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methyl-1-propan-2-yl-3-pyridin-4-ylindol-5-yl)oxypropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C(C)C)C(C)=C1C1=CC=NC=C1 TYFZKYVECDYBIX-UHFFFAOYSA-N 0.000 description 1
• QOCHABSELBZGPE-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methyl-1-propyl-3-pyridin-4-ylindol-6-yl)oxypropanoate Chemical compound C12=CC=C(OC(C)(C)C(=O)OCC)C=C2N(CCC)C(C)=C1C1=CC=NC=C1 QOCHABSELBZGPE-UHFFFAOYSA-N 0.000 description 1
• ZHIMFHQNSWOCRV-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methyl-3-phenyl-1-propylindol-4-yl)oxypropanoate Chemical compound C12=C(OC(C)(C)C(=O)OCC)C=CC=C2N(CCC)C(C)=C1C1=CC=CC=C1 ZHIMFHQNSWOCRV-UHFFFAOYSA-N 0.000 description 1
• IBUZNEFMRXPFAN-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methyl-3-phenyl-1-propylindol-6-yl)oxypropanoate Chemical compound C12=CC=C(OC(C)(C)C(=O)OCC)C=C2N(CCC)C(C)=C1C1=CC=CC=C1 IBUZNEFMRXPFAN-UHFFFAOYSA-N 0.000 description 1
• YRGGORAIKASNGR-UHFFFAOYSA-N ethyl 2-methyl-2-(2-phenyl-1-propylindol-5-yl)oxypropanoate Chemical compound C=1C2=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C=1C1=CC=CC=C1 YRGGORAIKASNGR-UHFFFAOYSA-N 0.000 description 1
• HTOOTLGZNCXVFL-UHFFFAOYSA-N ethyl 2-methyl-2-(3-methyl-1-propyl-2-pyridin-4-ylindol-5-yl)oxypropanoate Chemical compound CC=1C2=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C=1C1=CC=NC=C1 HTOOTLGZNCXVFL-UHFFFAOYSA-N 0.000 description 1
• SLALTRJEIDAPAE-UHFFFAOYSA-N ethyl 2-methyl-2-[(10-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]indol-2-yl)oxy]propanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N2CCCCC2=C1C1=CC=NC=C1 SLALTRJEIDAPAE-UHFFFAOYSA-N 0.000 description 1
• NLRMNPFUVNKYHN-UHFFFAOYSA-N ethyl 2-methyl-2-[(11-phenyl-7,8,9,10-tetrahydro-6h-azepino[1,2-a]indol-2-yl)oxy]propanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N2CCCCCC2=C1C1=CC=CC=C1 NLRMNPFUVNKYHN-UHFFFAOYSA-N 0.000 description 1
• OKKYXISTPSQAFJ-UHFFFAOYSA-N ethyl 2-methyl-2-[(11-pyridin-2-yl-7,8,9,10-tetrahydro-6h-azepino[1,2-a]indol-2-yl)oxy]propanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N2CCCCCC2=C1C1=CC=CC=N1 OKKYXISTPSQAFJ-UHFFFAOYSA-N 0.000 description 1
• JJRFAWKEKBCEKR-UHFFFAOYSA-N ethyl 2-methyl-2-[(11-quinolin-2-yl-7,8,9,10-tetrahydro-6h-azepino[1,2-a]indol-2-yl)oxy]propanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N2CCCCCC2=C1C1=CC=C(C=CC=C2)C2=N1 JJRFAWKEKBCEKR-UHFFFAOYSA-N 0.000 description 1
• RRQZCQBAKPRPOM-UHFFFAOYSA-N ethyl 2-methyl-2-[(2-methyl-3-pyridin-4-yl-1h-indol-5-yl)oxy]propanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2NC(C)=C1C1=CC=NC=C1 RRQZCQBAKPRPOM-UHFFFAOYSA-N 0.000 description 1
• QDHNSFPKSSBTOJ-UHFFFAOYSA-N ethyl 2-methyl-2-[(2-propan-2-yl-3-pyridin-4-yl-1h-indol-5-yl)oxy]propanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2NC(C(C)C)=C1C1=CC=NC=C1 QDHNSFPKSSBTOJ-UHFFFAOYSA-N 0.000 description 1
• QEBSVBABSSUGCD-UHFFFAOYSA-N ethyl 2-methyl-2-[1-propyl-3-(pyridin-4-ylmethyl)indol-5-yl]oxypropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C=C1CC1=CC=NC=C1 QEBSVBABSSUGCD-UHFFFAOYSA-N 0.000 description 1
• AULXCCTZPJQGCB-UHFFFAOYSA-N ethyl 2-methyl-2-[2-(4-nitrophenyl)-1-propylindol-6-yl]oxypropanoate Chemical compound C=1C2=CC=C(OC(C)(C)C(=O)OCC)C=C2N(CCC)C=1C1=CC=C([N+]([O-])=O)C=C1 AULXCCTZPJQGCB-UHFFFAOYSA-N 0.000 description 1
• SVLCFWZTKVBHPT-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-1-(2-methylpropyl)-3-pyridin-4-ylindol-5-yl]oxypropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CC(C)C)C(C)=C1C1=CC=NC=C1 SVLCFWZTKVBHPT-UHFFFAOYSA-N 0.000 description 1
• SSZSCUGVEVMWSC-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-3-(2-methylphenyl)-1-propylindol-5-yl]oxypropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1C1=CC=CC=C1C SSZSCUGVEVMWSC-UHFFFAOYSA-N 0.000 description 1
• NCWYLADOVWPYEQ-UHFFFAOYSA-N ethyl 2-methyl-2-[3-methyl-2-(4-nitrophenyl)-1-propylindol-5-yl]oxypropanoate Chemical compound CC=1C2=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C=1C1=CC=C([N+]([O-])=O)C=C1 NCWYLADOVWPYEQ-UHFFFAOYSA-N 0.000 description 1
• AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 1
• LLBDOBISQBECLH-UHFFFAOYSA-N ethyl 5-hydroxy-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(O)C=C2C=1C1=CC=CC=C1 LLBDOBISQBECLH-UHFFFAOYSA-N 0.000 description 1
• XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical class CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
• 125000004175 fluorobenzyl group Chemical group 0.000 description 1
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• 229920000669 heparin Polymers 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• OVNUPJXMCMTQCN-UHFFFAOYSA-N hydron;(4-phenylmethoxyphenyl)hydrazine;chloride Chemical compound Cl.C1=CC(NN)=CC=C1OCC1=CC=CC=C1 OVNUPJXMCMTQCN-UHFFFAOYSA-N 0.000 description 1
• 230000003516 hyperlipidaemic effect Effects 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 150000002463 imidates Chemical class 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
• FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 description 1
• 125000006303 iodophenyl group Chemical group 0.000 description 1
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
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• 239000011976 maleic acid Substances 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• GLQDTBFZNLIANN-UHFFFAOYSA-N methyl 2-[3-(2-methoxyphenyl)-1,2-dimethylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OC)=CC=C2N(C)C(C)=C1C1=CC=CC=C1OC GLQDTBFZNLIANN-UHFFFAOYSA-N 0.000 description 1
• PQUSVJVVRXWKDG-UHFFFAOYSA-N methyl 2-bromo-2-methylpropanoate Chemical compound COC(=O)C(C)(C)Br PQUSVJVVRXWKDG-UHFFFAOYSA-N 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• FGCBWFQOLWTWJE-UHFFFAOYSA-N n,n-diethyl-2-methyl-2-(2-methyl-1-propyl-3-pyridin-4-ylindol-5-yl)oxypropanamide Chemical compound C12=CC(OC(C)(C)C(=O)N(CC)CC)=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 FGCBWFQOLWTWJE-UHFFFAOYSA-N 0.000 description 1
• 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 1
• LWAVUAUIYWBRML-UHFFFAOYSA-N n-[4-(5-hydroxy-1-propylindol-2-yl)phenyl]acetamide Chemical compound C=1C2=CC(O)=CC=C2N(CCC)C=1C1=CC=C(NC(C)=O)C=C1 LWAVUAUIYWBRML-UHFFFAOYSA-N 0.000 description 1
• WUXKQXXQOIBHKI-UHFFFAOYSA-N n-cyclohexyl-2-methyl-2-(2-methyl-1-propyl-3-pyridin-4-ylindol-5-yl)oxypropanamide Chemical compound C12=CC(OC(C)(C)C(=O)NC3CCCCC3)=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 WUXKQXXQOIBHKI-UHFFFAOYSA-N 0.000 description 1
• DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• FXVDZRGQFVEMKZ-UHFFFAOYSA-N pentyl 2-[3-(4-chlorophenyl)-1,2-dimethylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCCCCC)=CC=C2N(C)C(C)=C1C1=CC=C(Cl)C=C1 FXVDZRGQFVEMKZ-UHFFFAOYSA-N 0.000 description 1
• 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 235000011007 phosphoric acid Nutrition 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• VDALTPJCMVJSCN-UHFFFAOYSA-N propyl 2-bromo-2-methylpropanoate Chemical compound CCCOC(=O)C(C)(C)Br VDALTPJCMVJSCN-UHFFFAOYSA-N 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 230000000284 resting effect Effects 0.000 description 1
• 238000006798 ring closing metathesis reaction Methods 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 230000003584 silencer Effects 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• VHRZANOPKQAAOM-UHFFFAOYSA-M sodium 2-methyl-2-[(11-pyridin-4-yl-7,8,9,10-tetrahydro-6H-azepino[1,2-a]indol-2-yl)oxy]propanoate Chemical compound [Na+].C12=CC(OC(C)(C)C([O-])=O)=CC=C2N2CCCCCC2=C1C1=CC=NC=C1 VHRZANOPKQAAOM-UHFFFAOYSA-M 0.000 description 1
• 229910001388 sodium aluminate Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 239000001119 stannous chloride Substances 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
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• 150000007970 thio esters Chemical class 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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