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
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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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (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 (cs)
EP (1)	EP0015523B1 (cs)
JP (1)	JPS55124758A (cs)
AT (1)	ATE1642T1 (cs)
AU (1)	AU5636880A (cs)
CA (1)	CA1142519A (cs)
CS (1)	CS208800B2 (cs)
DD (1)	DD149804A5 (cs)
DE (2)	DE2909779A1 (cs)
ES (3)	ES488446A1 (cs)
FI (1)	FI800770A7 (cs)
GR (1)	GR75241B (cs)
HU (1)	HU180126B (cs)
IL (1)	IL59598A0 (cs)
NO (1)	NO800709L (cs)
NZ (1)	NZ193111A (cs)
PL (1)	PL222634A1 (cs)
PT (1)	PT70921B (cs)
SU (1)	SU1028247A3 (cs)
YU (1)	YU68180A (cs)
ZA (1)	ZA801441B (cs)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA814057B (en) *	1980-06-18	1982-07-28	May & Baker Ltd	Indole and indoline derivatives
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
US4460777A (en) *	1981-11-19	1984-07-17	Ciba-Geigy Corporation	N-Substituted-2-pyridylindoles
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
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
DE69728688T2 (de)	1996-11-19	2004-08-19	Amgen Inc., Thousand Oaks	Aryl und heteroaryl substituierte kondensierte pyrrole als entzündunghemmende mittel
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
US7772271B2 (en)	2004-07-14	2010-08-10	Ptc Therapeutics, Inc.	Methods for treating hepatitis C
US7868037B2 (en)	2004-07-14	2011-01-11	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 CA CA000347485A patent/CA1142519A/en not_active Expired
- 1980-03-12 IL IL59598A patent/IL59598A0/xx unknown
- 1980-03-12 NO NO800709A patent/NO800709L/no unknown
- 1980-03-12 NZ NZ193111A patent/NZ193111A/xx unknown
- 1980-03-12 AU AU56368/80A patent/AU5636880A/en not_active Abandoned
- 1980-03-12 FI FI800770A patent/FI800770A7/fi not_active Application Discontinuation
- 1980-03-12 YU YU00681/80A patent/YU68180A/xx unknown
- 1980-03-12 HU HU8080591A patent/HU180126B/hu unknown
- 1980-03-12 ZA ZA00801441A patent/ZA801441B/xx unknown
- 1980-03-12 PL PL22263480A patent/PL222634A1/xx unknown
- 1980-04-09 ES ES490380A patent/ES490380A0/es active Granted
- 1980-04-09 ES ES490379A patent/ES8101047A1/es not_active Expired

Also Published As

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

Publication	Publication Date	Title
CH516574A (de)	1971-12-15	Verfahren zur Herstellung von 1H-Imidazo(3,5-b)pyrazin-2-onen
EP0015523B1 (de)	1982-10-13	Neue Indolderivate, deren Herstellung und Verwendung für Arzneimittel
EP0112987A1 (de)	1984-07-11	Imidazolylalkylthienyl-tetrahydropyridazine und Verfahren zu ihrer Herstellung
EP0011142B1 (de)	1982-12-29	Pyrido (2,1-b) chinazolinon-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
EP0327800B1 (de)	1992-05-27	6-Phenyldihydro-3(2H)-pyridazinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH638202A5 (de)	1983-09-15	3-(pyrazol-1-yl)-pyridazin-derivate, deren salze und verfahren zu ihrer herstellung.
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
DE1153023B (de)	1963-08-22	Verfahren zur Herstellung von 4-Hydroxy-pyrazolo[3,4-d] pyrimidinen
EP0175187A1 (de)	1986-03-26	Neue, eine Imidazol-gruppe enthaltende 3,4-Dihydro-2(1H)-Pyridone und 2(1H)-Pyridone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DD218362A5 (de)	1985-02-06	Verfahren zur herstellung von neuen 1h, 3h-pyrrolo (1,2-c) thiasol-derivaten
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
DE2831072A1 (de)	1979-05-10	3-(pyrazol-1'-yl)-pyridazinderivate, solche enthaltende arzneimittel und verfahren zur herstellung derselben
CH644125A5 (de)	1984-07-13	Benzo-as-triazin-derivate und verfahren zur herstellung derselben.
CH641800A5 (de)	1984-03-15	Pyrido-pyrimidine, verfahren zu ihrer herstellung und die diese verbindungen enthaltenden arzneimittel.
EP0063826B1 (de)	1984-12-05	2-Amino-benzoesäure-Derivate, deren Herstellung und deren Verwendung als Arzneimittel oder Zwischenprodukte
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
DE1620358C3 (de)	1974-10-10	Verfahren zur Herstellung von 1-Acyl-3-indolylcarbonsäure verbindungen