CS208800B2 - Method of making the new indole derivatives - Google Patents

Method of making the new indole derivatives Download PDF

Info

Publication number: CS208800B2
Authority: CS; Czechoslovakia
Prior art keywords: methyl; indol; group; yloxy; ethyl ester
Prior art date: 1979-03-13

Application number

CS801663A

Other languages

Czech (cs)

English (en)

Inventor

Rudolf Hurnaus

Gerhart Griss

Wolfgang Grell

Robert Sauter

Bernhard Eisele

Nikolaus Kaubisch

Eckhard Rupprecht

Joachim Kaehling

Original Assignee

Thomae Gmbh Dr K

Priority date (The priority date 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 date listed.)

1979-03-13

Filing date

1980-03-11

Publication date

1981-09-15

1980-03-11 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1981-09-15 Publication of CS208800B2 publication Critical patent/CS208800B2/cs

Links

229940054051 antipsychotic indole derivative Drugs 0.000 title claims abstract description 5
150000002475 indoles Chemical class 0.000 title claims abstract description 5
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 92
150000003839 salts Chemical class 0.000 claims abstract description 14
-1 aminophenyl group Chemical group 0.000 claims description 92
125000004432 carbon atom Chemical group C* 0.000 claims description 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
238000000034 method Methods 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 16
239000011541 reaction mixture Substances 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
239000002904 solvent Substances 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
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
238000009835 boiling Methods 0.000 claims description 7
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
230000021736 acetylation Effects 0.000 claims description 4
238000006640 acetylation reaction Methods 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 4
238000005886 esterification reaction Methods 0.000 claims description 4
125000006501 nitrophenyl group Chemical group 0.000 claims description 4
229910052736 halogen Chemical group 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000002560 nitrile group Chemical group 0.000 claims description 3
230000000269 nucleophilic effect Effects 0.000 claims description 3
239000003444 phase transfer catalyst Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
230000029936 alkylation Effects 0.000 abstract description 5
238000005804 alkylation reaction Methods 0.000 abstract description 5
JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 abstract description 4
230000000144 pharmacologic effect Effects 0.000 abstract description 4
150000002632 lipids Chemical class 0.000 abstract description 3
230000000879 anti-atherosclerotic effect Effects 0.000 abstract description 2
231100000252 nontoxic Toxicity 0.000 abstract 1
230000003000 nontoxic effect Effects 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 description 213
229910052757 nitrogen Inorganic materials 0.000 description 204
239000000047 product Substances 0.000 description 203
238000004458 analytical method Methods 0.000 description 133
239000000155 melt Substances 0.000 description 105
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 68
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
239000000203 mixture Substances 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000460 chlorine Substances 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
238000005904 alkaline hydrolysis reaction Methods 0.000 description 24
229910052801 chlorine Inorganic materials 0.000 description 23
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
239000003480 eluent Substances 0.000 description 19
239000000243 solution Substances 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
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 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
125000004494 ethyl ester group Chemical group 0.000 description 11
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 11
235000019260 propionic acid Nutrition 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
238000005903 acid hydrolysis reaction Methods 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
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 7
238000001704 evaporation Methods 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
150000007522 mineralic acids Chemical class 0.000 description 7
150000007524 organic acids Chemical class 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
239000000725 suspension Substances 0.000 description 7
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
229940093915 gynecological organic acid Drugs 0.000 description 6
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 6
235000005985 organic acids Nutrition 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 5
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
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 5
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
210000002966 serum Anatomy 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
238000006264 debenzylation reaction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012362 glacial acetic acid Substances 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
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
KVWYSENZPIZXEL-UHFFFAOYSA-N 2-methyl-2-[(11-pyridin-4-yl-7,8,9,10-tetrahydro-6h-azepino[1,2-a]indol-2-yl)oxy]propanoic acid Chemical compound C12=CC(OC(C)(C)C(O)=O)=CC=C2N2CCCCCC2=C1C1=CC=NC=C1 KVWYSENZPIZXEL-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
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 3
NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
230000009435 amidation Effects 0.000 description 3
238000007112 amidation reaction Methods 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000000354 decomposition reaction Methods 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
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
QZNNVYOVQUKYSC-JEDNCBNOSA-N (2s)-2-amino-3-(1h-imidazol-5-yl)propanoic acid;hydron;chloride Chemical compound Cl.OC(=O)[C@@H](N)CC1=CN=CN1 QZNNVYOVQUKYSC-JEDNCBNOSA-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
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
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
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
YEBHTWWXLWRHGC-UHFFFAOYSA-N 1-butyl-3-(4-fluorophenyl)-2-methylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCCC)C(C)=C1C1=CC=C(F)C=C1 YEBHTWWXLWRHGC-UHFFFAOYSA-N 0.000 description 2
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
IOQBRZSLQQCYJD-UHFFFAOYSA-N 2-(4-aminophenyl)-3-methyl-1-propylindol-5-ol Chemical compound CC=1C2=CC(O)=CC=C2N(CCC)C=1C1=CC=C(N)C=C1 IOQBRZSLQQCYJD-UHFFFAOYSA-N 0.000 description 2
INNQWWUNUSXFPR-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methyl-1-propylindol-5-ol Chemical compound CC=1C2=CC(O)=CC=C2N(CCC)C=1C1=CC=C(Cl)C=C1 INNQWWUNUSXFPR-UHFFFAOYSA-N 0.000 description 2
VJIDGRCEYCZVSR-UHFFFAOYSA-N 2-(4-nitrophenyl)-1-propylindol-6-ol Chemical compound C=1C2=CC=C(O)C=C2N(CCC)C=1C1=CC=C([N+]([O-])=O)C=C1 VJIDGRCEYCZVSR-UHFFFAOYSA-N 0.000 description 2
RAXNZLAXPKLXPU-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)-1,2-dimethylindol-5-yl]oxy-2-methylpropanamide Chemical compound C12=CC(OC(C)(C)C(N)=O)=CC=C2N(C)C(C)=C1C1=CC=C(Cl)C=C1 RAXNZLAXPKLXPU-UHFFFAOYSA-N 0.000 description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
VNONRUICOKMKRK-UHFFFAOYSA-N 2-methyl-1-propan-2-yl-3-pyridin-4-ylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(C(C)C)C(C)=C1C1=CC=NC=C1 VNONRUICOKMKRK-UHFFFAOYSA-N 0.000 description 2
ZBJZUWPFYAFENQ-UHFFFAOYSA-N 2-methyl-1-propyl-3-pyridin-4-ylindol-4-ol Chemical compound C12=C(O)C=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 ZBJZUWPFYAFENQ-UHFFFAOYSA-N 0.000 description 2
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 2
MORWFHPPDZRMAS-UHFFFAOYSA-N 2-methyl-1-propyl-3-pyridin-4-ylindol-6-ol Chemical compound C12=CC=C(O)C=C2N(CCC)C(C)=C1C1=CC=NC=C1 MORWFHPPDZRMAS-UHFFFAOYSA-N 0.000 description 2
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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VDMOQEPXBKFYMS-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-hexyl-2-methylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCCCCC)C(C)=C1C1=CC=C(Cl)C=C1 VDMOQEPXBKFYMS-UHFFFAOYSA-N 0.000 description 2
UVLXLCBDELWCAE-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-methyl-1-propylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1C1=CC=C(Cl)C=C1 UVLXLCBDELWCAE-UHFFFAOYSA-N 0.000 description 2
NCNDOHGMYUWRPS-UHFFFAOYSA-N 3-(4-fluorophenyl)-1,2-dimethylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(C)C(C)=C1C1=CC=C(F)C=C1 NCNDOHGMYUWRPS-UHFFFAOYSA-N 0.000 description 2
PIMWGVPZOWORMQ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1,2-dimethylindol-7-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C)N(C)C2=C(O)C=CC=C12 PIMWGVPZOWORMQ-UHFFFAOYSA-N 0.000 description 2
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WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 2
SEQNVZZZCKCKAR-UHFFFAOYSA-N 3-methyl-1-propyl-2-pyridin-4-ylindol-5-ol Chemical compound CC=1C2=CC(O)=CC=C2N(CCC)C=1C1=CC=NC=C1 SEQNVZZZCKCKAR-UHFFFAOYSA-N 0.000 description 2
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 2
PGIXAYFWMYVXRA-UHFFFAOYSA-N 4-pyridin-4-yl-6,7-dihydro-5h-pyrrolo[1,2-a]indol-2-ol Chemical compound C=12CCCC=C2N2C=C(O)C=C2C=1C1=CC=NC=C1 PGIXAYFWMYVXRA-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
208000031226 Hyperlipidaemia Diseases 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
102000004895 Lipoproteins Human genes 0.000 description 2
108090001030 Lipoproteins Proteins 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000004799 bromophenyl group Chemical group 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
125000004803 chlorobenzyl group Chemical group 0.000 description 2
125000000068 chlorophenyl group Chemical group 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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 2
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 2
FQCRLUSGLNRCJZ-UHFFFAOYSA-N ethyl 2-[1,2-dimethyl-3-[3-(trifluoromethyl)phenyl]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(F)(F)F)=C1 FQCRLUSGLNRCJZ-UHFFFAOYSA-N 0.000 description 2
SMGMSHPDJDVNLK-UHFFFAOYSA-N ethyl 2-[1-butyl-3-(4-fluorophenyl)-2-methylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCCC)C(C)=C1C1=CC=C(F)C=C1 SMGMSHPDJDVNLK-UHFFFAOYSA-N 0.000 description 2
CULJJMXXJHVDID-UHFFFAOYSA-N ethyl 2-[2-(4-chlorophenyl)-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(Cl)C=C1 CULJJMXXJHVDID-UHFFFAOYSA-N 0.000 description 2
YWAFLHVFIGOCQW-UHFFFAOYSA-N ethyl 2-[2-(4-methoxyphenyl)-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(OC)C=C1 YWAFLHVFIGOCQW-UHFFFAOYSA-N 0.000 description 2
YXSIIKPCRXKRHW-UHFFFAOYSA-N ethyl 2-[3-(2-bromophenyl)-1-ethyl-2-methylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CC)C(C)=C1C1=CC=CC=C1Br YXSIIKPCRXKRHW-UHFFFAOYSA-N 0.000 description 2
CUSQYJRKEANVPW-UHFFFAOYSA-N ethyl 2-[3-(2-chlorophenyl)-2-methyl-1-propylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1C1=CC=CC=C1Cl CUSQYJRKEANVPW-UHFFFAOYSA-N 0.000 description 2
FXHRQPRMOFWFFE-UHFFFAOYSA-N ethyl 2-[3-(3-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=CC(Cl)=C1 FXHRQPRMOFWFFE-UHFFFAOYSA-N 0.000 description 2
YRBNFCIKSADKEN-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)-1-dodecyl-2-methylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCCCCCCCCCCC)C(C)=C1C1=CC=C(Cl)C=C1 YRBNFCIKSADKEN-UHFFFAOYSA-N 0.000 description 2
PHKWKUOGAJYNTM-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)-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(Cl)C=C1 PHKWKUOGAJYNTM-UHFFFAOYSA-N 0.000 description 2
WDMNEULAWKQEIC-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)-2-methyl-1-propylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1C1=CC=C(Cl)C=C1 WDMNEULAWKQEIC-UHFFFAOYSA-N 0.000 description 2
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 2
VOJGCDWKROHJQW-UHFFFAOYSA-N ethyl 2-methyl-2-(3-methyl-2-phenyl-1-propylindol-5-yl)oxypropanoate Chemical compound CC=1C2=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C=1C1=CC=CC=C1 VOJGCDWKROHJQW-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
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FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
125000001207 fluorophenyl group Chemical group 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
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RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
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 2
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 2
150000002825 nitriles Chemical class 0.000 description 2
150000007530 organic bases Chemical group 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000000523 sample Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
230000009747 swallowing Effects 0.000 description 2
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
239000012485 toluene extract Substances 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
ALLYUHIQZKTLFG-RBUKOAKNSA-N (2r)-n-[(2s)-1-[(6-aminopyridin-3-yl)methylamino]-3-(3,4-difluorophenyl)-1-oxopropan-2-yl]-1-ethylpyrrolidine-2-carboxamide Chemical compound CCN1CCC[C@@H]1C(=O)N[C@H](C(=O)NCC=1C=NC(N)=CC=1)CC1=CC=C(F)C(F)=C1 ALLYUHIQZKTLFG-RBUKOAKNSA-N 0.000 description 1
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
KQBDLOVXZHOAJI-UHFFFAOYSA-N (4-phenylmethoxyphenyl)azanium;chloride Chemical compound Cl.C1=CC(N)=CC=C1OCC1=CC=CC=C1 KQBDLOVXZHOAJI-UHFFFAOYSA-N 0.000 description 1
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
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LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000012345 acetylating agent Substances 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
238000005574 benzylation reaction Methods 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
125000006278 bromobenzyl group Chemical group 0.000 description 1
MAHCHOYFMMBKAB-UHFFFAOYSA-N butyl 2-[3-(4-chlorophenyl)-1,2-dimethylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCCCC)=CC=C2N(C)C(C)=C1C1=CC=C(Cl)C=C1 MAHCHOYFMMBKAB-UHFFFAOYSA-N 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
229960002471 cholic acid Drugs 0.000 description 1
235000019416 cholic acid Nutrition 0.000 description 1
SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
229960003178 choline chloride Drugs 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
VJPHAMJNGICSLT-UHFFFAOYSA-N cyclohexanecarboxylic acid N-methylamide Natural products CNC(=O)C1CCCCC1 VJPHAMJNGICSLT-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000007876 drug discovery Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
GNMIJZPEMGIVSZ-UHFFFAOYSA-N ethyl 2-(1,2-dimethyl-3-phenylindol-5-yl)oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C)=C1C1=CC=CC=C1 GNMIJZPEMGIVSZ-UHFFFAOYSA-N 0.000 description 1
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
AXWDSGSJTZXINU-UHFFFAOYSA-N ethyl 2-(1,2-dimethyl-3-pyridin-4-ylindol-5-yl)oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(C)C(C)=C1C1=CC=NC=C1 AXWDSGSJTZXINU-UHFFFAOYSA-N 0.000 description 1
KGGZESBYRIULEZ-UHFFFAOYSA-N ethyl 2-(1-butyl-2-methyl-3-pyridin-4-ylindol-5-yl)oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCCC)C(C)=C1C1=CC=NC=C1 KGGZESBYRIULEZ-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
UFKSSPVOKLKJEJ-UHFFFAOYSA-N ethyl 2-(3-benzyl-2-methyl-1-propylindol-5-yl)oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1CC1=CC=CC=C1 UFKSSPVOKLKJEJ-UHFFFAOYSA-N 0.000 description 1
KUFWSCPWSFDUSL-UHFFFAOYSA-N ethyl 2-[(1,3-dimethyl-11-pyridin-4-yl-7,8,9,10-tetrahydro-6h-azepino[1,2-a]indol-2-yl)oxy]-2-methylpropanoate Chemical compound C12=C(C)C(OC(C)(C)C(=O)OCC)=C(C)C=C2N2CCCCCC2=C1C1=CC=NC=C1 KUFWSCPWSFDUSL-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
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
GZZBJEYLFCKUOU-UHFFFAOYSA-N ethyl 2-[2-(4-aminophenyl)-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(N)C=C1 GZZBJEYLFCKUOU-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
PMINQKMCJFUHNA-UHFFFAOYSA-N ethyl 2-[3-(4-methoxyphenyl)-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(OC)C=C1 PMINQKMCJFUHNA-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
NDRKZWFSAIGKBU-UHFFFAOYSA-N ethyl 2-[3-(4-methoxyphenyl)-2-methyl-1-propylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1C1=CC=C(OC)C=C1 NDRKZWFSAIGKBU-UHFFFAOYSA-N 0.000 description 1
WUKAPXVMNAYFSA-UHFFFAOYSA-N ethyl 2-[3-[(4-chlorophenyl)methyl]-2-methyl-1-propylindol-5-yl]oxy-2-methylpropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1CC1=CC=C(Cl)C=C1 WUKAPXVMNAYFSA-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
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
IARUAFNGYQQTJG-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methyl-1-propyl-3-pyridin-4-ylindol-4-yl)oxypropanoate Chemical compound C12=C(OC(C)(C)C(=O)OCC)C=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 IARUAFNGYQQTJG-UHFFFAOYSA-N 0.000 description 1
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 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
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
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
GJFNJDJDQODAAU-UHFFFAOYSA-N ethyl 2-methyl-2-[(2-methyl-3-phenyl-1h-indol-4-yl)oxy]propanoate Chemical compound C1=2C(OC(C)(C)C(=O)OCC)=CC=CC=2NC(C)=C1C1=CC=CC=C1 GJFNJDJDQODAAU-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
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
ULJAYDMAKHHHEU-UHFFFAOYSA-N ethyl 2-methyl-2-[2-methyl-3-(2-phenylethyl)-1-propylindol-5-yl]oxypropanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2N(CCC)C(C)=C1CCC1=CC=CC=C1 ULJAYDMAKHHHEU-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
DGCCPMLPAGNTKP-UHFFFAOYSA-N ethyl 2-methyl-2-[[2-methyl-3-(3-methylphenyl)-1h-indol-5-yl]oxy]propanoate Chemical compound C12=CC(OC(C)(C)C(=O)OCC)=CC=C2NC(C)=C1C1=CC=CC(C)=C1 DGCCPMLPAGNTKP-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
125000004175 fluorobenzyl group Chemical group 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
150000004795 grignard reagents Chemical class 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
238000005984 hydrogenation reaction Methods 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
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
PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical compound C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
125000006303 iodophenyl group Chemical group 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 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
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
238000002156 mixing Methods 0.000 description 1
LFCCWFUWPGZYNN-UHFFFAOYSA-N n,2-dimethyl-2-(2-methyl-1-propyl-3-pyridin-4-ylindol-5-yl)oxypropanamide Chemical compound C12=CC(OC(C)(C)C(=O)NC)=CC=C2N(CCC)C(C)=C1C1=CC=NC=C1 LFCCWFUWPGZYNN-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
YUMCRXLLWKQDJY-UHFFFAOYSA-N n-propylpropanamide Chemical compound CCCNC(=O)CC YUMCRXLLWKQDJY-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
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
239000003921 oil Substances 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
BBGHXSYMRZDMRG-UHFFFAOYSA-N pentyl 2-bromo-2-methylpropanoate Chemical compound CCCCCOC(=O)C(C)(C)Br BBGHXSYMRZDMRG-UHFFFAOYSA-N 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 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
XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 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
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
229910001388 sodium aluminate 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
159000000000 sodium salts Chemical class 0.000 description 1
239000011343 solid material 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
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Obesity (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Photoreceptors In Electrophotography (AREA)
Power Steering Mechanism (AREA)
Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)

CS801663A 1979-03-13 1980-03-11 Method of making the new indole derivatives CS208800B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792909779 DE2909779A1 (de)	1979-03-13	1979-03-13	Neue indolderivate, deren herstellung und deren verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
CS208800B2 true CS208800B2 (en)	1981-09-15

Family

ID=6065240

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS801663A CS208800B2 (en)	1979-03-13	1980-03-11	Method of making the new indole derivatives

Country Status (21)

Country	Link
US (1)	US4343811A (es)
EP (1)	EP0015523B1 (es)
JP (1)	JPS55124758A (es)
AT (1)	ATE1642T1 (es)
AU (1)	AU5636880A (es)
CA (1)	CA1142519A (es)
CS (1)	CS208800B2 (es)
DD (1)	DD149804A5 (es)
DE (2)	DE2909779A1 (es)
ES (3)	ES488446A1 (es)
FI (1)	FI800770A (es)
GR (1)	GR75241B (es)
HU (1)	HU180126B (es)
IL (1)	IL59598A0 (es)
NO (1)	NO800709L (es)
NZ (1)	NZ193111A (es)
PL (1)	PL222634A1 (es)
PT (1)	PT70921B (es)
SU (1)	SU1028247A3 (es)
YU (1)	YU68180A (es)
ZA (1)	ZA801441B (es)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI811889L (fi) *	1980-06-18	1981-12-19	May & Baker Ltd	Foerfarande foer framstaellning av farmakologiskt aktiva indol- och indolinderivat
US4543360A (en) *	1981-09-10	1985-09-24	Degussa Aktiengesellschaft	2-(Hydroxy-phenyl)-indoles and process for their production
DE3232968A1 (de) *	1981-09-10	1983-06-09	Degussa Ag, 6000 Frankfurt	Neue 2-(hydroxy-phenyl)-indole und verfahren zu deren herstellung
GB2111050B (en) *	1981-11-19	1985-09-11	Ciba Geigy Ag	N-substituted-2-pyridylindoles
US4478842A (en) *	1981-11-19	1984-10-23	Ciba-Geigy Corporation	N-Substituted-2-pyridylindoles
US4460777A (en) *	1981-11-19	1984-07-17	Ciba-Geigy Corporation	N-Substituted-2-pyridylindoles
US4647576A (en) *	1984-09-24	1987-03-03	Warner-Lambert Company	Trans-6-[2-(substitutedpyrrol-1-yl)alkyl]-pyran-2-one inhibitors of cholesterol synthesis
US4759923A (en) *	1987-06-25	1988-07-26	Hercules Incorporated	Process for lowering serum cholesterol using poly(diallylmethylamine) derivatives
WO1998022457A1 (en)	1996-11-19	1998-05-28	Amgen Inc.	Aryl and heteroaryl substituted fused pyrrole antiinflammatory agents
US6103733A (en) *	1998-09-09	2000-08-15	Bachmann; Kenneth A.	Method for increasing HDL cholesterol levels using heteroaromatic phenylmethanes
US7868037B2 (en)	2004-07-14	2011-01-11	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
US7781478B2 (en)	2004-07-14	2010-08-24	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
US7772271B2 (en)	2004-07-14	2010-08-10	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
JP2008507518A (ja)	2004-07-22	2008-03-13	ピーティーシーセラピューティクス，インコーポレーテッド	Ｃ型肝炎を治療するためのチエノピリジン
DE102006053064A1 (de) *	2006-11-08	2008-05-21	Universität Potsdam	Verfahren zur Herstellung aromatischer Diazoniumsalze

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2237361A1 (de) *	1972-07-29	1974-02-14	Boehringer Mannheim Gmbh	(5-indolyloxy)-essigsaeure-derivate und verfahren zur herstellung derselben
FI59246C (fi) *	1974-06-24	1981-07-10	Otsuka Pharma Co Ltd	Foerfarande foer framstaellning av benscykloamidderivat anvaendbara vid trombos- och emboliterapin

1979
- 1979-03-13 DE DE19792909779 patent/DE2909779A1/de not_active Withdrawn
1980
- 1980-02-11 ES ES488446A patent/ES488446A1/es not_active Expired
- 1980-02-12 SU SU802879303A patent/SU1028247A3/ru active
- 1980-02-19 GR GR61231A patent/GR75241B/el unknown
- 1980-02-29 US US06/126,006 patent/US4343811A/en not_active Expired - Lifetime
- 1980-03-03 EP EP80101037A patent/EP0015523B1/de not_active Expired
- 1980-03-03 AT AT80101037T patent/ATE1642T1/de not_active IP Right Cessation
- 1980-03-03 DE DE8080101037T patent/DE3060932D1/de not_active Expired
- 1980-03-10 DD DD80219568A patent/DD149804A5/de unknown
- 1980-03-10 PT PT70921A patent/PT70921B/pt unknown
- 1980-03-11 JP JP3083480A patent/JPS55124758A/ja active Pending
- 1980-03-11 CS CS801663A patent/CS208800B2/cs unknown
- 1980-03-12 IL IL59598A patent/IL59598A0/xx unknown
- 1980-03-12 NZ NZ193111A patent/NZ193111A/xx unknown
- 1980-03-12 CA CA000347485A patent/CA1142519A/en not_active Expired
- 1980-03-12 HU HU8080591A patent/HU180126B/hu unknown
- 1980-03-12 PL PL22263480A patent/PL222634A1/xx unknown
- 1980-03-12 NO NO800709A patent/NO800709L/no unknown
- 1980-03-12 ZA ZA00801441A patent/ZA801441B/xx unknown
- 1980-03-12 AU AU56368/80A patent/AU5636880A/en not_active Abandoned
- 1980-03-12 FI FI800770A patent/FI800770A/fi not_active Application Discontinuation
- 1980-03-12 YU YU00681/80A patent/YU68180A/xx unknown
- 1980-04-09 ES ES490379A patent/ES8101047A1/es not_active Expired
- 1980-04-09 ES ES490380A patent/ES8101048A1/es not_active Expired

Also Published As

Publication number	Publication date
DE3060932D1 (en)	1982-11-18
ES490380A0 (es)	1980-12-01
ES490379A0 (es)	1980-12-01
PL222634A1 (es)	1980-12-01
ES8101048A1 (es)	1980-12-01
ES8101047A1 (es)	1980-12-01
PT70921B (de)	1981-06-24
PT70921A (de)	1980-04-01
ES488446A1 (es)	1980-10-01
ZA801441B (en)	1981-11-25
JPS55124758A (en)	1980-09-26
SU1028247A3 (ru)	1983-07-07
FI800770A (fi)	1980-09-14
CA1142519A (en)	1983-03-08
EP0015523A1 (de)	1980-09-17
GR75241B (es)	1984-07-13
EP0015523B1 (de)	1982-10-13
DE2909779A1 (de)	1980-09-18
AU5636880A (en)	1980-09-18
IL59598A0 (en)	1980-06-30
YU68180A (en)	1983-04-30
DD149804A5 (de)	1981-07-29
HU180126B (en)	1983-02-28
NZ193111A (en)	1983-04-12
ATE1642T1 (de)	1982-10-15
NO800709L (no)	1980-09-15
US4343811A (en)	1982-08-10

Publication	Publication Date	Title
CS208800B2 (en)	1981-09-15	Method of making the new indole derivatives
DE69617731T2 (de)	2002-08-08	Neue heterozyklische derivate und ihre medizinische anwendung
HU220221B (hu)	2001-11-28	1H-Indol-3-ecetsav-hidrazid-származékok, a vegyületeket tartalmazó gyógyászati készítmények és eljárás előállításukra
SE447255B (sv)	1986-11-03	Karbostyrilderivat och forfarande for framstellning derav
WO2002046158A2 (en)	2002-06-13	Piperidine/piperazine-type inhibitors of p38 kinase
JPH04145079A (ja)	1992-05-19	インドール誘導体およびその用途
PT2311805E (pt)	2012-07-18	Nova forma polimórfica de acetato de bazedoxifeno
CZ290871B6 (cs)	2002-11-13	Indolový derivát, farmaceutický prostředek jej obsahující a způsob přípravy tohoto derivátu
EP0070518A2 (en)	1983-01-26	Imidazoquinoxaline compounds
NZ519692A (en)	2004-05-28	Phenylpiperazinyl, -piperidinyl or -tetrahydropyridinyl derivatives
FI91748C (fi)	1994-08-10	Menetelmä terapeuttisesti käyttökelpoisten kinolinonijohdannaisten valmistamiseksi
US4048182A (en)	1977-09-13	Derivatives of imidazo [4,5-b]pyridines
EP0937715B1 (en)	2005-06-01	Tetrahydrobenzindole compounds
DE69107064T2 (de)	1995-05-24	Indolderivate.
JP4199668B2 (ja)	2008-12-17	Ｓｓｔ１アンタゴニスト活性を有するピペラジン誘導体
SU1195903A3 (ru)	1985-11-30	Способ получени 1-фенил- 2-аминокарбонилиндольных соединений или их солей присоединени кислот
PT90269B (pt)	1994-07-29	Processo para a preparacao de carboxamidas hetero-alifaticas e de composicoes farmaceuticas que as contem
KR20020063285A (ko)	2002-08-01	4-페닐-1-피페라지닐,-피페리디닐 및 -테트라히드로피리딜유도체
CH643554A5 (de)	1984-06-15	Verfahren zur herstellung von piperidinopropanolderivaten.
IE65569B1 (en)	1995-11-01	Aliphatic carboxamides
US4950677A (en)	1990-08-21	Benzimidazole derivative compounds and method of making
CA1244435A (en)	1988-11-08	Pyrazolo¬1,5-a\|pyridine derivatives and compositions containing them
US4292323A (en)	1981-09-29	Phenyl-1,2,3,4-tetrahydrocarbazoles and use thereof
CN114890999A (zh)	2022-08-12	一种pqq的制备方法
WO1997003965A1 (fr)	1997-02-06	Derives d'indole