CH445490A - Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen-säuren - Google Patents
Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen-säurenInfo
- Publication number
- CH445490A CH445490A CH1736966A CH1736966A CH445490A CH 445490 A CH445490 A CH 445490A CH 1736966 A CH1736966 A CH 1736966A CH 1736966 A CH1736966 A CH 1736966A CH 445490 A CH445490 A CH 445490A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- group
- indolyl
- chloride
- methyl
- Prior art date
Links
- -1 3-indolyl Chemical group 0.000 title claims description 47
- 239000002253 acid Substances 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 3
- 230000009935 nitrosation Effects 0.000 claims description 3
- 238000007034 nitrosation reaction Methods 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- TXWGINUZLBAKDF-UHFFFAOYSA-N N-Deschlorobenzoyl indomethacin Chemical compound COC1=CC=C2NC(C)=C(CC(O)=O)C2=C1 TXWGINUZLBAKDF-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 9
- 238000005917 acylation reaction Methods 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000010933 acylation Effects 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 125000001041 indolyl group Chemical group 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229940067157 phenylhydrazine Drugs 0.000 description 4
- 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 4
- 150000003254 radicals Chemical class 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UGJDXRVQCYBXAJ-UHFFFAOYSA-N 4-(dimethylamino)benzoyl chloride Chemical compound CN(C)C1=CC=C(C(Cl)=O)C=C1 UGJDXRVQCYBXAJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- ICYOLCFDSJJLAC-UHFFFAOYSA-N gramine Chemical class C1=CC=C[C]2C(CN(C)C)=CN=C21 ICYOLCFDSJJLAC-UHFFFAOYSA-N 0.000 description 2
- GOERTRUXQHDLHC-UHFFFAOYSA-N gramine Natural products COC1=CC=C2NC=C(CN(C)C)C2=C1 GOERTRUXQHDLHC-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 150000004031 phenylhydrazines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- HWZQBVSDSPXTBX-UHFFFAOYSA-N 1,3-dimethyl-2-oxoimidazole-4-carbonyl chloride Chemical compound CN1C(N(C(=C1)C(=O)Cl)C)=O HWZQBVSDSPXTBX-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- WSNDAYQNZRJGMJ-UHFFFAOYSA-N 2,2,2-trifluoroethanone Chemical compound FC(F)(F)[C]=O WSNDAYQNZRJGMJ-UHFFFAOYSA-N 0.000 description 1
- BONFTDXNVIOQBZ-UHFFFAOYSA-N 2,4,5-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=C(Cl)C=C1Cl BONFTDXNVIOQBZ-UHFFFAOYSA-N 0.000 description 1
- FDXOLWVATQFZJC-UHFFFAOYSA-N 2-(1-benzoyl-5-methoxy-2-methylindol-3-yl)acetamide Chemical compound CC1=C(CC(N)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=CC=C1 FDXOLWVATQFZJC-UHFFFAOYSA-N 0.000 description 1
- HHVVFSZNIUHMEJ-UHFFFAOYSA-N 2-(1-benzoyl-5-methoxy-2-methylindol-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=CC=C1 HHVVFSZNIUHMEJ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FUEWIOXAEUFASQ-UHFFFAOYSA-N 2-(5-methoxy-2-methyl-1h-indol-3-yl)acetamide Chemical compound COC1=CC=C2NC(C)=C(CC(N)=O)C2=C1 FUEWIOXAEUFASQ-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical class [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical class CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-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
- OSRNDBCXJHFFLC-UHFFFAOYSA-N 3-methylimidazole-4-carbonyl chloride Chemical compound CN1C=NC=C1C(Cl)=O OSRNDBCXJHFFLC-UHFFFAOYSA-N 0.000 description 1
- RBOMQQAMVJDXBU-UHFFFAOYSA-N 4-(2,2,2-trifluoroacetyl)benzoyl chloride Chemical compound FC(F)(F)C(=O)C1=CC=C(C(Cl)=O)C=C1 RBOMQQAMVJDXBU-UHFFFAOYSA-N 0.000 description 1
- OXLNFFBYPUFBCX-UHFFFAOYSA-N 4-(trifluoromethyl)benzenecarbothioyl chloride Chemical compound FC(F)(F)C1=CC=C(C(Cl)=S)C=C1 OXLNFFBYPUFBCX-UHFFFAOYSA-N 0.000 description 1
- UZPDKLGPANSZTM-UHFFFAOYSA-N 4-acetylbenzoyl chloride Chemical compound CC(=O)C1=CC=C(C(Cl)=O)C=C1 UZPDKLGPANSZTM-UHFFFAOYSA-N 0.000 description 1
- CCBOXJLPEZRSSA-UHFFFAOYSA-N 4-chloro-2-hydroxybenzoyl chloride Chemical compound OC1=CC(Cl)=CC=C1C(Cl)=O CCBOXJLPEZRSSA-UHFFFAOYSA-N 0.000 description 1
- OKEFBVALFLRAFV-UHFFFAOYSA-N 4-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC(Cl)=CC=C1C(Cl)=O OKEFBVALFLRAFV-UHFFFAOYSA-N 0.000 description 1
- USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 1
- PVLSJNOHBYQCPD-UHFFFAOYSA-N 4-methylsulfinylbenzoyl chloride Chemical compound CS(=O)C1=CC=C(C(Cl)=O)C=C1 PVLSJNOHBYQCPD-UHFFFAOYSA-N 0.000 description 1
- IPEIDGXNXFPGBG-UHFFFAOYSA-N 4-methylsulfonylbenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=C(C(Cl)=O)C=C1 IPEIDGXNXFPGBG-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- AOOZVQGGMFGGEE-UHFFFAOYSA-N 4-phenoxybenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=CC=C1 AOOZVQGGMFGGEE-UHFFFAOYSA-N 0.000 description 1
- PIGPGBJMESGOTG-UHFFFAOYSA-N 4-sulfanylbenzoyl chloride Chemical compound SC1=CC=C(C(Cl)=O)C=C1 PIGPGBJMESGOTG-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- HCRATYVLHABEFF-UHFFFAOYSA-N 5-fluorothiophene-2-carbonyl chloride Chemical compound FC1=CC=C(C(Cl)=O)S1 HCRATYVLHABEFF-UHFFFAOYSA-N 0.000 description 1
- OZFPSOBLQZPIAV-UHFFFAOYSA-N 5-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=C2NC=CC2=C1 OZFPSOBLQZPIAV-UHFFFAOYSA-N 0.000 description 1
- OLEFNFXYGGTROA-UHFFFAOYSA-N 5-nitrofuran-2-carbonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)O1 OLEFNFXYGGTROA-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- SOVSRQDGJFMQQI-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C1=CC=C(C(=S)Cl)C=C1 Chemical compound C(C1=CC=CC=C1)(=O)C1=CC=C(C(=S)Cl)C=C1 SOVSRQDGJFMQQI-UHFFFAOYSA-N 0.000 description 1
- CIHCYOATKNZBGL-UHFFFAOYSA-N CC1=CC=C(C(=S)N2C(=C(C3=CC(=CC=C23)OC)CC(=O)O)C)C=C1 Chemical compound CC1=CC=C(C(=S)N2C(=C(C3=CC(=CC=C23)OC)CC(=O)O)C)C=C1 CIHCYOATKNZBGL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005262 alkoxyamine group Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000006383 alkylpyridyl group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- NHVHYFAWHCJELN-UHFFFAOYSA-N benzene;n,n-dimethylformamide Chemical compound CN(C)C=O.C1=CC=CC=C1 NHVHYFAWHCJELN-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- DIQDUFVJZPNLJQ-UHFFFAOYSA-N indol-1-yl(phenyl)methanone Chemical group C1=CC2=CC=CC=C2N1C(=O)C1=CC=CC=C1 DIQDUFVJZPNLJQ-UHFFFAOYSA-N 0.000 description 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- CVXXHXPNTZBZEL-UHFFFAOYSA-N methyl 4-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=O)C=C1 CVXXHXPNTZBZEL-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical group OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- XYMVZPOXZCDCNP-UHFFFAOYSA-N sulfamoyl cyanide Chemical compound NS(=O)(=O)C#N XYMVZPOXZCDCNP-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9743461A | 1961-03-22 | 1961-03-22 | |
| US16461562A | 1962-01-05 | 1962-01-05 | |
| US28693563 US3161654A (en) | 1962-01-05 | 1963-06-11 | alpha-(1-aroyl-3-indolyl) alkanoic acids |
| US296451A US3201414A (en) | 1963-07-22 | 1963-07-22 | New 1-heteroacyl-3-indolyl aliphatic acids |
| US31047763A | 1963-09-20 | 1963-09-20 | |
| US31045463A | 1963-09-20 | 1963-09-20 | |
| US314503A US3242185A (en) | 1963-10-07 | 1963-10-07 | Lower aliphatic acids, salts and derivatives thereof |
| US32386363A | 1963-11-04 | 1963-11-04 | |
| US321328A US3275644A (en) | 1962-01-05 | 1963-11-04 | Certain 1-azolylindol-3-ylaliphatic acids |
| US321686A US3275645A (en) | 1962-01-05 | 1963-11-06 | N-(1-acyl-3-indolyl)-acids |
| US437338A US3338921A (en) | 1962-01-05 | 1965-01-26 | Thenoic and furoic acids |
| US442152A US3328423A (en) | 1962-01-05 | 1965-03-23 | alpha-(3-indolyl)-cyclopropyl lower aliphatic acids |
| US528020A US3316267A (en) | 1962-01-05 | 1966-02-15 | Indolyl acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH445490A true CH445490A (de) | 1967-10-31 |
Family
ID=27584499
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1736966A CH445490A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen-säuren |
| CH1737166A CH445492A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von in 1-Stellung acylierten a-(3-Indolyl)-niederaliphatischen-säuren |
| CH1736866A CH450420A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen Säuren |
| CH1737066A CH445491A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen-säuren |
| CH1737266A CH445493A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung des Anhydrids von N-1-unsubstituierten a-(3-Indolyl)-niederaliphatischen-säuren |
| CH1737366A CH449018A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung der t-Butylester von N-1-unsubstituierten a-(3-Indolyl)-niederaliphatischen Säuren |
| CH1736766A CH450419A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen Estern bzw. Amiden |
| CH335362A CH426822A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen-säuren |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1737166A CH445492A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von in 1-Stellung acylierten a-(3-Indolyl)-niederaliphatischen-säuren |
| CH1736866A CH450420A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen Säuren |
| CH1737066A CH445491A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen-säuren |
| CH1737266A CH445493A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung des Anhydrids von N-1-unsubstituierten a-(3-Indolyl)-niederaliphatischen-säuren |
| CH1737366A CH449018A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung der t-Butylester von N-1-unsubstituierten a-(3-Indolyl)-niederaliphatischen Säuren |
| CH1736766A CH450419A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen Estern bzw. Amiden |
| CH335362A CH426822A (de) | 1961-03-22 | 1962-03-21 | Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen-säuren |
Country Status (9)
| Country | Link |
|---|---|
| CH (8) | CH445490A (https=) |
| CY (1) | CY348A (https=) |
| DE (3) | DE1795543C3 (https=) |
| DK (5) | DK111959B (https=) |
| FI (2) | FI41158B (https=) |
| GB (1) | GB997638A (https=) |
| MY (1) | MY6600092A (https=) |
| NO (2) | NO135064C (https=) |
| SE (5) | SE315592B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU176215B (en) | 1978-01-27 | 1981-01-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing a cyclodextrin-indomethacin inclusion complex with a ratio of at about 2:1 |
| US7135495B2 (en) | 2000-03-09 | 2006-11-14 | Ono Pharmaceutical Co., Ltd. | Indole derivatives |
| CA2459515A1 (en) * | 2001-09-07 | 2003-03-20 | Kazuhiko Torisu | Indole derivatives |
| US20230218644A1 (en) | 2020-04-16 | 2023-07-13 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| CN113248419A (zh) * | 2021-06-09 | 2021-08-13 | 云南中医药大学 | 一种新型HuR抑制剂1-苯磺酰基-3-苯基吲哚-4,5-二酮的合成方法 |
| CN115417804A (zh) * | 2022-09-16 | 2022-12-02 | 天津药明康德新药开发有限公司 | 一种7-甲基-1h-吲哚-5-羧酸的合成方法 |
-
1962
- 1962-03-16 DE DE1795543A patent/DE1795543C3/de not_active Expired
- 1962-03-16 FI FI0561/62A patent/FI41158B/fi active
- 1962-03-16 DE DE1962M0070803 patent/DE1620031B1/de active Pending
- 1962-03-16 DE DE1962M0070802 patent/DE1620030B1/de active Pending
- 1962-03-20 GB GB10695/62A patent/GB997638A/en not_active Expired
- 1962-03-21 CH CH1736966A patent/CH445490A/de unknown
- 1962-03-21 CH CH1737166A patent/CH445492A/de unknown
- 1962-03-21 CH CH1736866A patent/CH450420A/de unknown
- 1962-03-21 CH CH1737066A patent/CH445491A/de unknown
- 1962-03-21 CH CH1737266A patent/CH445493A/de unknown
- 1962-03-21 CH CH1737366A patent/CH449018A/de unknown
- 1962-03-21 CH CH1736766A patent/CH450419A/de unknown
- 1962-03-21 CH CH335362A patent/CH426822A/de unknown
- 1962-03-21 SE SE11783/66A patent/SE315592B/xx unknown
-
1966
- 1966-05-25 DK DK268166AA patent/DK111959B/da unknown
- 1966-06-03 CY CY34866A patent/CY348A/xx unknown
- 1966-09-01 SE SE1178166A patent/SE315282B/xx unknown
- 1966-09-01 SE SE1178062A patent/SE315281B/xx unknown
- 1966-09-01 SE SE1178266A patent/SE314984B/xx unknown
- 1966-09-01 SE SE1178466A patent/SE315593B/xx unknown
- 1966-11-11 DK DK586166AA patent/DK120340B/da unknown
- 1966-11-11 DK DK586266AA patent/DK116737B/da unknown
- 1966-11-11 DK DK586366AA patent/DK120637B/da unknown
- 1966-12-28 FI FI3456/66A patent/FI41159B/fi active
- 1966-12-31 MY MY196692A patent/MY6600092A/xx unknown
-
1967
- 1967-02-13 DK DK77067AA patent/DK114975B/da unknown
-
1968
- 1968-04-01 NO NO1234/68A patent/NO135064C/no unknown
-
1969
- 1969-11-11 NO NO445869A patent/NO122372B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620031B1 (de) | 1971-04-08 |
| FI41159B (https=) | 1969-06-02 |
| CH450420A (de) | 1968-01-31 |
| SE315282B (https=) | 1969-09-29 |
| CH450419A (de) | 1968-01-31 |
| DE1795543C3 (de) | 1980-06-04 |
| DK114975B (da) | 1969-08-25 |
| DK116737B (da) | 1970-02-09 |
| DE1795543B2 (de) | 1979-09-20 |
| NO135064B (https=) | 1976-10-25 |
| FI41158B (https=) | 1969-06-02 |
| DK111959B (da) | 1968-10-28 |
| DK120637B (da) | 1971-06-28 |
| CH445492A (de) | 1967-10-31 |
| SE315281B (https=) | 1969-09-29 |
| CH426822A (de) | 1966-12-31 |
| CH449018A (de) | 1967-12-31 |
| SE315592B (https=) | 1969-10-06 |
| DE1795543A1 (de) | 1972-01-13 |
| SE314984B (https=) | 1969-09-22 |
| NO135064C (https=) | 1977-02-02 |
| DE1620030B1 (de) | 1970-03-05 |
| MY6600092A (en) | 1966-12-31 |
| CH445491A (de) | 1967-10-31 |
| NO122372B (https=) | 1971-06-21 |
| GB997638A (en) | 1965-07-07 |
| CY348A (en) | 1966-06-03 |
| DK120340B (da) | 1971-05-17 |
| SE315593B (https=) | 1969-10-06 |
| CH445493A (de) | 1967-10-31 |
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