DD149804A5 - Verfahren zur herstellung von neuen indolderivaten - Google Patents

Verfahren zur herstellung von neuen indolderivaten Download PDF

Info

Publication number: DD149804A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; group; indol; general formula; phenyl
Prior art date: 1979-03-13

Application number

DD80219568A

Other languages

German (de)

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

1980-03-10

Publication date

1981-07-29

1980-03-10 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1981-07-29 Publication of DD149804A5 publication Critical patent/DD149804A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 50
150000002475 indoles Chemical class 0.000 claims abstract description 13
230000029936 alkylation Effects 0.000 claims abstract description 10
238000005804 alkylation reaction Methods 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 claims abstract description 9
229940054051 antipsychotic indole derivative Drugs 0.000 claims abstract description 7
150000007524 organic acids Chemical class 0.000 claims abstract description 7
235000005985 organic acids Nutrition 0.000 claims abstract description 7
150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
-1 methoxy, amino Chemical group 0.000 claims description 137
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 50
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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 22
125000004076 pyridyl group Chemical group 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
239000002585 base Substances 0.000 claims description 13
238000009835 boiling Methods 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
238000006460 hydrolysis reaction Methods 0.000 claims description 9
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 8
230000007062 hydrolysis Effects 0.000 claims description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
150000002576 ketones Chemical class 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000007529 inorganic bases Chemical class 0.000 claims 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 claims description 4
125000002560 nitrile group Chemical group 0.000 claims description 4
230000000269 nucleophilic effect Effects 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
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
125000003118 aryl group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
150000007530 organic bases Chemical group 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
239000003444 phase transfer catalyst Substances 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
229910000040 hydrogen fluoride Inorganic materials 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 abstract description 4
230000000879 anti-atherosclerotic effect Effects 0.000 abstract description 2
101100072621 Streptomyces griseus ind7 gene Proteins 0.000 abstract 1
238000007796 conventional method Methods 0.000 abstract 1
238000002844 melting Methods 0.000 description 129
230000008018 melting Effects 0.000 description 129
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 54
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 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
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
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
238000005904 alkaline hydrolysis reaction Methods 0.000 description 23
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 22
WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 20
235000019260 propionic acid Nutrition 0.000 description 19
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
125000004494 ethyl ester group Chemical group 0.000 description 16
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 14
150000002148 esters Chemical class 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
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 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
238000001816 cooling Methods 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 8
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
238000010992 reflux Methods 0.000 description 8
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 7
XXSPGBOGLXKMDU-UHFFFAOYSA-N 2-bromo-2-methylpropanoic acid Chemical compound CC(C)(Br)C(O)=O XXSPGBOGLXKMDU-UHFFFAOYSA-N 0.000 description 7
238000005903 acid hydrolysis reaction Methods 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
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 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 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
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
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 4
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 4
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 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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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
238000006264 debenzylation reaction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229940093915 gynecological organic acid Drugs 0.000 description 4
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 4
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 4
239000001294 propane Substances 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
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
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
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
125000000068 chlorophenyl group Chemical group 0.000 description 3
235000012000 cholesterol Nutrition 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
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000000706 filtrate Substances 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
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
MYSMZPNGCQZOSF-UHFFFAOYSA-N 1,3-dimethyl-2-pyridin-4-ylindol-5-ol Chemical compound CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=NC=C1 MYSMZPNGCQZOSF-UHFFFAOYSA-N 0.000 description 2
229940005561 1,4-benzoquinone Drugs 0.000 description 2
POTVSNIGCNJNEM-UHFFFAOYSA-N 1-butyl-2-methyl-3-pyridin-4-ylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCCC)C(C)=C1C1=CC=NC=C1 POTVSNIGCNJNEM-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
MYTYNRIXJIDJJP-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-methyl-1-propylindol-5-ol Chemical compound CC=1C2=CC(O)=CC=C2N(CCC)C=1C1=CC=C(OC)C=C1 MYTYNRIXJIDJJP-UHFFFAOYSA-N 0.000 description 2
XDSDCTDECRVDTB-UHFFFAOYSA-N 2-bromo-2-methylpropanenitrile Chemical compound CC(C)(Br)C#N XDSDCTDECRVDTB-UHFFFAOYSA-N 0.000 description 2
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 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
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
LHCCUKVBHPJVRG-UHFFFAOYSA-N 2-methyl-3-pyridin-4-yl-1h-indol-5-ol Chemical compound CC=1NC2=CC=C(O)C=C2C=1C1=CC=NC=C1 LHCCUKVBHPJVRG-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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 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
UZARSNXTMUTDLR-UHFFFAOYSA-N 3-methyl-2-(4-nitrophenyl)-1-propylindol-5-ol Chemical compound CC=1C2=CC(O)=CC=C2N(CCC)C=1C1=CC=C([N+]([O-])=O)C=C1 UZARSNXTMUTDLR-UHFFFAOYSA-N 0.000 description 2
IAGMKZQNNOWEJX-UHFFFAOYSA-N 3-methyl-2-phenyl-1-propylindol-5-ol Chemical compound CC=1C2=CC(O)=CC=C2N(CCC)C=1C1=CC=CC=C1 IAGMKZQNNOWEJX-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
NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
102000007330 LDL Lipoproteins Human genes 0.000 description 2
108010007622 LDL 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
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
241000700159 Rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
150000007513 acids Chemical class 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000004799 bromophenyl group Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
125000004803 chlorobenzyl group Chemical group 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 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
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-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
238000010828 elution Methods 0.000 description 2
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 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
125000001207 fluorophenyl group Chemical group 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000003304 gavage Methods 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000003516 hyperlipidaemic effect Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
235000013847 iso-butane Nutrition 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 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
150000002905 orthoesters Chemical class 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
159000000000 sodium salts Chemical class 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-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
MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
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 1
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 1
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 1
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 1
VCNYPJMEQHTAHS-UHFFFAOYSA-N 1-(3-chlorophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=CC(Cl)=C1 VCNYPJMEQHTAHS-UHFFFAOYSA-N 0.000 description 1
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
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 1
FZGIXTQIYMNEOX-UHFFFAOYSA-N 1-ethyl-2-methyl-3-pyridin-4-ylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CC)C(C)=C1C1=CC=NC=C1 FZGIXTQIYMNEOX-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
RJDBUWCNOSRGMB-UHFFFAOYSA-N 1-methyl-2-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 RJDBUWCNOSRGMB-UHFFFAOYSA-N 0.000 description 1
LAAHPFCQVWTSIK-UHFFFAOYSA-N 1-propylindole Chemical compound C1=CC=C2N(CCC)C=CC2=C1 LAAHPFCQVWTSIK-UHFFFAOYSA-N 0.000 description 1
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
QOPBEBWGSGFROG-UHFFFAOYSA-N 2-(1h-indol-2-yl)acetic acid Chemical compound C1=CC=C2NC(CC(=O)O)=CC2=C1 QOPBEBWGSGFROG-UHFFFAOYSA-N 0.000 description 1
VYNRJMXIGZTPQN-UHFFFAOYSA-N 2-(4-aminophenyl)-1-propylindol-6-ol Chemical compound C=1C2=CC=C(O)C=C2N(CCC)C=1C1=CC=C(N)C=C1 VYNRJMXIGZTPQN-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
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 1
KLZVCRHOWASGFJ-UHFFFAOYSA-N 2-[[3-[2-(4-chlorophenyl)ethyl]-2-methyl-1h-indol-5-yl]oxy]-2-methylpropanoic acid Chemical compound CC=1NC2=CC=C(OC(C)(C)C(O)=O)C=C2C=1CCC1=CC=C(Cl)C=C1 KLZVCRHOWASGFJ-UHFFFAOYSA-N 0.000 description 1
LAPNNMSEGPABDA-UHFFFAOYSA-N 2-benzyl-3-pyridin-4-yl-1h-indol-5-ol Chemical compound C=1C=NC=CC=1C=1C2=CC(O)=CC=C2NC=1CC1=CC=CC=C1 LAPNNMSEGPABDA-UHFFFAOYSA-N 0.000 description 1
WPDWOCRJBPXJFM-UHFFFAOYSA-N 2-bromo-1-phenylpropan-1-one Chemical compound CC(Br)C(=O)C1=CC=CC=C1 WPDWOCRJBPXJFM-UHFFFAOYSA-N 0.000 description 1
COOYFNIWDZJKJL-UHFFFAOYSA-N 2-bromo-2-methyl-1-piperidin-1-ylpropan-1-one Chemical compound CC(C)(Br)C(=O)N1CCCCC1 COOYFNIWDZJKJL-UHFFFAOYSA-N 0.000 description 1
XXSPGBOGLXKMDU-UHFFFAOYSA-M 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C([O-])=O XXSPGBOGLXKMDU-UHFFFAOYSA-M 0.000 description 1
239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
OTNPBGQILUWSJY-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)-3-pyridin-4-ylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CC(C)C)C(C)=C1C1=CC=NC=C1 OTNPBGQILUWSJY-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
MDWJZBVEVLTXDE-UHFFFAOYSA-N 2-methyl-1h-indol-5-ol Chemical compound OC1=CC=C2NC(C)=CC2=C1 MDWJZBVEVLTXDE-UHFFFAOYSA-N 0.000 description 1
XVAKPLLSQWQBDX-UHFFFAOYSA-N 2-methyl-3-(2-methylphenyl)-1-propylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1C1=CC=CC=C1C XVAKPLLSQWQBDX-UHFFFAOYSA-N 0.000 description 1
SLZVTKQOFOVWLG-UHFFFAOYSA-N 2-methyl-3-(2-phenylethyl)-1-propylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1CCC1=CC=CC=C1 SLZVTKQOFOVWLG-UHFFFAOYSA-N 0.000 description 1
VDIYHYKNOCPTEU-UHFFFAOYSA-N 2-methyl-3-(3-methylphenyl)-1h-indol-5-ol Chemical compound CC=1NC2=CC=C(O)C=C2C=1C1=CC=CC(C)=C1 VDIYHYKNOCPTEU-UHFFFAOYSA-N 0.000 description 1
PBCVKUAZWLXXEP-UHFFFAOYSA-N 2-methyl-3-phenyl-1,5,6,7-tetrahydroindol-4-one Chemical compound CC=1NC=2CCCC(=O)C=2C=1C1=CC=CC=C1 PBCVKUAZWLXXEP-UHFFFAOYSA-N 0.000 description 1
WFSXUXKBOUYYIH-UHFFFAOYSA-N 2-methyl-3-phenyl-1-propylindol-6-ol Chemical compound C12=CC=C(O)C=C2N(CCC)C(C)=C1C1=CC=CC=C1 WFSXUXKBOUYYIH-UHFFFAOYSA-N 0.000 description 1
VQDKHRQOCZVKDL-UHFFFAOYSA-N 2-methyl-3-phenyl-1h-indol-4-ol Chemical compound CC=1NC2=CC=CC(O)=C2C=1C1=CC=CC=C1 VQDKHRQOCZVKDL-UHFFFAOYSA-N 0.000 description 1
WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
LAGDURGUNCQADL-UHFFFAOYSA-N 2-methylpropanoic acid;hydrochloride Chemical compound Cl.CC(C)C(O)=O LAGDURGUNCQADL-UHFFFAOYSA-N 0.000 description 1
DEXNMAVUHYFCBA-UHFFFAOYSA-N 2-phenyl-1-propylindol-5-ol Chemical compound C=1C2=CC(O)=CC=C2N(CCC)C=1C1=CC=CC=C1 DEXNMAVUHYFCBA-UHFFFAOYSA-N 0.000 description 1
CIXPNPWVGBFXQK-UHFFFAOYSA-N 2-propan-2-yl-3-pyridin-4-yl-1h-indol-5-ol Chemical compound CC(C)C=1NC2=CC=C(O)C=C2C=1C1=CC=NC=C1 CIXPNPWVGBFXQK-UHFFFAOYSA-N 0.000 description 1
TVIPPMNOKDHKTC-UHFFFAOYSA-N 3,4-dibenzyl-1-propylindol-5-ol Chemical compound C12=C(CC=3C=CC=CC=3)C(O)=CC=C2N(CCC)C=C1CC1=CC=CC=C1 TVIPPMNOKDHKTC-UHFFFAOYSA-N 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
UGNSNVZLAFWSNT-UHFFFAOYSA-N 3-(2-bromophenyl)-1-ethyl-2-methylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CC)C(C)=C1C1=CC=CC=C1Br UGNSNVZLAFWSNT-UHFFFAOYSA-N 0.000 description 1
CVKOXRTXCXJXDK-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-methyl-1-propylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1C1=CC=CC=C1Cl CVKOXRTXCXJXDK-UHFFFAOYSA-N 0.000 description 1
FEUZOUHTBZQDBH-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-methyl-1h-indol-5-ol Chemical compound CC=1NC2=CC=C(O)C=C2C=1C1=CC=CC=C1Cl FEUZOUHTBZQDBH-UHFFFAOYSA-N 0.000 description 1
GKEKWPBNCLERDW-UHFFFAOYSA-N 3-(2-methoxyphenyl)-1,2-dimethylindol-5-ol Chemical compound COC1=CC=CC=C1C1=C(C)N(C)C2=CC=C(O)C=C12 GKEKWPBNCLERDW-UHFFFAOYSA-N 0.000 description 1
QLPNFXDEEFYFAN-UHFFFAOYSA-N 3-(3-chlorophenyl)-1,2-dimethyl-5-phenylmethoxyindole Chemical compound C12=CC(OCC=3C=CC=CC=3)=CC=C2N(C)C(C)=C1C1=CC=CC(Cl)=C1 QLPNFXDEEFYFAN-UHFFFAOYSA-N 0.000 description 1
HGYGBUUZQMMDJR-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methyl-5-phenylmethoxy-1h-indole Chemical compound C1=C2C(C=3C=C(Cl)C=CC=3)=C(C)NC2=CC=C1OCC1=CC=CC=C1 HGYGBUUZQMMDJR-UHFFFAOYSA-N 0.000 description 1
ITAVWXVWKYGWQR-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-dodecyl-2-methylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCCCCCCCCCCC)C(C)=C1C1=CC=C(Cl)C=C1 ITAVWXVWKYGWQR-UHFFFAOYSA-N 0.000 description 1
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 1
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 1
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 1
SJJWLAIPLSXNPJ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-methyl-1h-indol-5-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C)NC2=CC=C(O)C=C12 SJJWLAIPLSXNPJ-UHFFFAOYSA-N 0.000 description 1
JSNAGGWDELCTFW-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-2-methyl-1-propylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1CC1=CC=C(Cl)C=C1 JSNAGGWDELCTFW-UHFFFAOYSA-N 0.000 description 1
VFLMDRRBCADZCH-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)ethyl]-2-methyl-1-propylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1CCC1=CC=C(Cl)C=C1 VFLMDRRBCADZCH-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
HGQLKNOGAXMQLU-UHFFFAOYSA-N 3-benzyl-2-methyl-1-propylindol-5-ol Chemical compound C12=CC(O)=CC=C2N(CCC)C(C)=C1CC1=CC=CC=C1 HGQLKNOGAXMQLU-UHFFFAOYSA-N 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
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 1
ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
FIIDVVUUWRJXLF-UHFFFAOYSA-N 4-phenylmethoxyaniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=C1 FIIDVVUUWRJXLF-UHFFFAOYSA-N 0.000 description 1
LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 description 1
JCQLPDZCNSVBMS-UHFFFAOYSA-N 5-phenylmethoxy-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1OCC1=CC=CC=C1 JCQLPDZCNSVBMS-UHFFFAOYSA-N 0.000 description 1
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000004380 Cholic acid Substances 0.000 description 1
235000019743 Choline chloride Nutrition 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
XDWQYMXQMNUWID-UHFFFAOYSA-N Ethyl 2-benzylacetoacetate Chemical compound CCOC(=O)C(C(C)=O)CC1=CC=CC=C1 XDWQYMXQMNUWID-UHFFFAOYSA-N 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
DKQACEIFVQGZLT-UHFFFAOYSA-N NC1=CC=C(C=C1)C=1N(C2=CC=C(C=C2C1C)O)CCC.COC1=CC=C(C=C1)C1=C(N(C2=C(C=CC=C12)O)C)C Chemical compound NC1=CC=C(C=C1)C=1N(C2=CC=C(C=C2C1C)O)CCC.COC1=CC=C(C=C1)C1=C(N(C2=C(C=CC=C12)O)C)C DKQACEIFVQGZLT-UHFFFAOYSA-N 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-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
150000001241 acetals Chemical class 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000012345 acetylating agent Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
125000004429 atom Chemical group 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
BOWQDFRKKXVCCI-UHFFFAOYSA-N butyl 2-bromo-2-methylpropanoate Chemical compound CCCCOC(=O)C(C)(C)Br BOWQDFRKKXVCCI-UHFFFAOYSA-N 0.000 description 1
BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 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
235000015165 citric acid Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
150000003997 cyclic ketones Chemical class 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
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 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
235000001916 dieting Nutrition 0.000 description 1
230000037228 dieting effect Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000007876 drug discovery Methods 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
QWNSENSNYRIKSN-UHFFFAOYSA-N ethyl 1-(5-ethoxy-5-oxopentyl)-3-phenyl-5-phenylmethoxyindole-2-carboxylate Chemical compound C12=CC(OCC=3C=CC=CC=3)=CC=C2N(CCCCC(=O)OCC)C(C(=O)OCC)=C1C1=CC=CC=C1 QWNSENSNYRIKSN-UHFFFAOYSA-N 0.000 description 1
QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-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
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
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 1
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 1
ALHOFXQMBUWICK-UHFFFAOYSA-N ethyl 2-bromo-2-methylbutanoate Chemical compound CCOC(=O)C(C)(Br)CC ALHOFXQMBUWICK-UHFFFAOYSA-N 0.000 description 1
CKGLEDHIOHOSEW-UHFFFAOYSA-N ethyl 3-phenyl-5-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C1=C2C(C=3C=CC=CC=3)=C(C(=O)OCC)NC2=CC=C1OCC1=CC=CC=C1 CKGLEDHIOHOSEW-UHFFFAOYSA-N 0.000 description 1
AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-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
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004175 fluorobenzyl group Chemical group 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
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
150000002431 hydrogen Chemical class 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
239000005457 ice water Substances 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
238000007654 immersion Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical compound C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
150000002484 inorganic compounds 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
125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
BOQMMYJLVCWIAC-UHFFFAOYSA-N n-cyclohexyl-n-methylpropanamide Chemical compound CCC(=O)N(C)C1CCCCC1 BOQMMYJLVCWIAC-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
230000003472 neutralizing effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[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
DBSMLQTUDJVICQ-CJODITQLSA-N onametostat Chemical compound NC1=C2C=CN([C@@H]3C[C@H](CCC4=CC=C5C=C(Br)C(N)=NC5=C4)[C@@H](O)[C@H]3O)C2=NC=N1 DBSMLQTUDJVICQ-CJODITQLSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
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
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000003303 reheating Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 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
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
239000005720 sucrose Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 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
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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)
Hematology (AREA)
Diabetes (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD80219568A 1979-03-13 1980-03-10 Verfahren zur herstellung von neuen indolderivaten DD149804A5 (de)

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
DD149804A5 true DD149804A5 (de)	1981-07-29

Family

ID=6065240

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80219568A DD149804A5 (de)	1979-03-13	1980-03-10	Verfahren zur herstellung von neuen indolderivaten

Country Status (21)

Country	Link
US (1)	US4343811A (fr)
EP (1)	EP0015523B1 (fr)
JP (1)	JPS55124758A (fr)
AT (1)	ATE1642T1 (fr)
AU (1)	AU5636880A (fr)
CA (1)	CA1142519A (fr)
CS (1)	CS208800B2 (fr)
DD (1)	DD149804A5 (fr)
DE (2)	DE2909779A1 (fr)
ES (3)	ES488446A1 (fr)
FI (1)	FI800770A7 (fr)
GR (1)	GR75241B (fr)
HU (1)	HU180126B (fr)
IL (1)	IL59598A0 (fr)
NO (1)	NO800709L (fr)
NZ (1)	NZ193111A (fr)
PL (1)	PL222634A1 (fr)
PT (1)	PT70921B (fr)
SU (1)	SU1028247A3 (fr)
YU (1)	YU68180A (fr)
ZA (1)	ZA801441B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR850001470B1 (ko) *	1980-06-18	1985-10-10	메이 앤드 베이커 리미팃드	인돌 유도체의 제조 방법
DE3232968A1 (de) *	1981-09-10	1983-06-09	Degussa Ag, 6000 Frankfurt	Neue 2-(hydroxy-phenyl)-indole und verfahren zu deren herstellung
US4543360A (en) *	1981-09-10	1985-09-24	Degussa Aktiengesellschaft	2-(Hydroxy-phenyl)-indoles and process for their production
GB2111050B (en) *	1981-11-19	1985-09-11	Ciba Geigy Ag	N-substituted-2-pyridylindoles
US4460777A (en) *	1981-11-19	1984-07-17	Ciba-Geigy Corporation	N-Substituted-2-pyridylindoles
US4478842A (en) *	1981-11-19	1984-10-23	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
KR20000057137A (ko)	1996-11-19	2000-09-15	스티븐 엠. 오드레	아릴 및 헤테로아릴로 치환된 융합 피롤 항염증제
US6103733A (en) *	1998-09-09	2000-08-15	Bachmann; Kenneth A.	Method for increasing HDL cholesterol levels using heteroaromatic phenylmethanes
US7781478B2 (en)	2004-07-14	2010-08-24	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
US7868037B2 (en)	2004-07-14	2011-01-11	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
US7772271B2 (en)	2004-07-14	2010-08-10	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
WO2006019832A1 (fr)	2004-07-22	2006-02-23	Ptc Therapeutics, Inc.	Thienopyridines utilisees pour traiter l'hepatite c
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 DE DE8080101037T patent/DE3060932D1/de not_active Expired
- 1980-03-03 EP EP80101037A patent/EP0015523B1/fr not_active Expired
- 1980-03-03 AT AT80101037T patent/ATE1642T1/de not_active IP Right Cessation
- 1980-03-10 PT PT70921A patent/PT70921B/pt unknown
- 1980-03-10 DD DD80219568A patent/DD149804A5/de unknown
- 1980-03-11 CS CS801663A patent/CS208800B2/cs unknown
- 1980-03-11 JP JP3083480A patent/JPS55124758A/ja active Pending
- 1980-03-12 ZA ZA00801441A patent/ZA801441B/xx unknown
- 1980-03-12 PL PL22263480A patent/PL222634A1/xx unknown
- 1980-03-12 YU YU00681/80A patent/YU68180A/xx unknown
- 1980-03-12 HU HU8080591A patent/HU180126B/hu unknown
- 1980-03-12 NO NO800709A patent/NO800709L/no unknown
- 1980-03-12 NZ NZ193111A patent/NZ193111A/xx unknown
- 1980-03-12 FI FI800770A patent/FI800770A7/fi not_active Application Discontinuation
- 1980-03-12 IL IL59598A patent/IL59598A0/xx unknown
- 1980-03-12 CA CA000347485A patent/CA1142519A/fr not_active Expired
- 1980-03-12 AU AU56368/80A patent/AU5636880A/en not_active Abandoned
- 1980-04-09 ES ES490379A patent/ES490379A0/es active Granted
- 1980-04-09 ES ES490380A patent/ES8101048A1/es not_active Expired

Also Published As

Publication number	Publication date
FI800770A7 (fi)	1981-01-01
DE2909779A1 (de)	1980-09-18
PT70921A (de)	1980-04-01
EP0015523B1 (fr)	1982-10-13
CS208800B2 (en)	1981-09-15
ES488446A1 (es)	1980-10-01
US4343811A (en)	1982-08-10
ATE1642T1 (de)	1982-10-15
PT70921B (de)	1981-06-24
JPS55124758A (en)	1980-09-26
HU180126B (en)	1983-02-28
CA1142519A (fr)	1983-03-08
GR75241B (fr)	1984-07-13
YU68180A (en)	1983-04-30
ES490380A0 (es)	1980-12-01
ZA801441B (en)	1981-11-25
EP0015523A1 (fr)	1980-09-17
PL222634A1 (fr)	1980-12-01
ES8101047A1 (es)	1980-12-01
NO800709L (no)	1980-09-15
IL59598A0 (en)	1980-06-30
ES490379A0 (es)	1980-12-01
AU5636880A (en)	1980-09-18
ES8101048A1 (es)	1980-12-01
NZ193111A (en)	1983-04-12
DE3060932D1 (en)	1982-11-18
SU1028247A3 (ru)	1983-07-07

Publication	Publication Date	Title
DD149804A5 (de)	1981-07-29	Verfahren zur herstellung von neuen indolderivaten
CH516574A (de)	1971-12-15	Verfahren zur Herstellung von 1H-Imidazo(3,5-b)pyrazin-2-onen
EP0112987A1 (fr)	1984-07-11	Imidazolylalkylthiényl-tétrahydropyridazines et procédé de leur préparation
DD206991A5 (de)	1984-02-15	Verfahren zur herstellung neuer piperazinone
EP0011142B1 (fr)	1982-12-29	Dérivés de la pyrido (2,1-b) quinazolinone, procédés pour leur préparation et compositions pharmaceutiques les contenant
CH638202A5 (de)	1983-09-15	3-(pyrazol-1-yl)-pyridazin-derivate, deren salze und verfahren zu ihrer herstellung.
DE3804490A1 (de)	1989-08-24	Substituierte 6-phenyldihydro-3(2h)-pyridazinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DD200152A5 (de)	1983-03-23	Verfahren zur herstellung neuer 2-aminobenzoesaeure-derivate
DE2310031A1 (de)	1973-09-20	Substituierte 1-benzyl-indazol-3carbonsaeuren
DD202021A5 (de)	1983-08-24	Verfahren zur herstellung neuer carbonsaeure-derivate
DE1224746B (de)	1966-09-15	Verfahren zur Herstellung von 5-Aminopyrazolderivaten
DE1545670A1 (de)	1969-08-07	Neue Diazacycloalkane
DE1153023B (de)	1963-08-22	Verfahren zur Herstellung von 4-Hydroxy-pyrazolo[3,4-d] pyrimidinen
EP0175187A1 (fr)	1986-03-26	Dihydro-3,4 (1H)-pyridones-2 et (1H)-pyridones-2 contenant un groupe imidazole, procédé pour leur préparation et médicaments les contenant
DE1770372A1 (de)	1971-10-21	Neue Indolinderivate und Verfahren zu ihrer Herstellung
DE3132915A1 (de)	1983-03-03	1,5-diphenylpyrazolin-3-on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE1770222A1 (de)	1971-11-11	Neue schwefelhaltige Pyridinderivate
DE2443682A1 (de)	1975-03-20	Neue benzylpyrimidine
DE2261009A1 (de)	1973-06-20	Neue isochinolinderivate
CH637951A5 (de)	1983-08-31	3-pyrazol-1-yl-pyridazin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelpraeparate.
CH644125A5 (de)	1984-07-13	Benzo-as-triazin-derivate und verfahren zur herstellung derselben.
EP0063826B1 (fr)	1984-12-05	Dérivés de l'acide amino-2-benzoique, leur préparation et leur utilisation comme médicaments ou intermédiaires
DE3401911A1 (de)	1985-08-01	Substituierte 4,5-dihydro-6-vinyl-3(2h)-pyridazinone und 6-vinyl-3(2h)-pyridazinone sowie verfahren zu ihrer herstellung
DE2340217A1 (de)	1974-02-21	3-benzoylthiophene, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
AT347450B (de)	1978-12-27	Verfahren zur herstellung neuer imidazol- derivate und ihrer salze