DE1620442C3 - Verfahren zur Herstellung von 1-Acylindolverbindungen - Google Patents
Verfahren zur Herstellung von 1-AcylindolverbindungenInfo
- Publication number
- DE1620442C3 DE1620442C3 DE1620442A DE1620442A DE1620442C3 DE 1620442 C3 DE1620442 C3 DE 1620442C3 DE 1620442 A DE1620442 A DE 1620442A DE 1620442 A DE1620442 A DE 1620442A DE 1620442 C3 DE1620442 C3 DE 1620442C3
- Authority
- DE
- Germany
- Prior art keywords
- chlorobenzoyl
- methyl
- yield
- compounds
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 p-hydroxyphenyl Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 9
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 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 6
- 239000002904 solvent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- OQFRGKBEAZOCIH-UHFFFAOYSA-N (4-chlorophenyl)-(3-ethyl-5-methoxyindol-1-yl)methanone Chemical compound C12=CC=C(OC)C=C2C(CC)=CN1C(=O)C1=CC=C(Cl)C=C1 OQFRGKBEAZOCIH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 3
- 229940124599 anti-inflammatory drug Drugs 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 150000001728 carbonyl compounds Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- VDRRZJNPCHBQLB-UHFFFAOYSA-N (3-benzyl-2-methylindol-1-yl)-(4-chlorophenyl)methanone Chemical compound ClC1=CC=C(C(=O)N2C(=C(C3=CC=CC=C23)CC2=CC=CC=C2)C)C=C1 VDRRZJNPCHBQLB-UHFFFAOYSA-N 0.000 description 2
- SFWPKKAWFSDSPB-UHFFFAOYSA-N (4-chlorophenyl)-(3-ethyl-5-methoxy-2-methylindol-1-yl)methanone Chemical compound C12=CC=C(OC)C=C2C(CC)=C(C)N1C(=O)C1=CC=C(Cl)C=C1 SFWPKKAWFSDSPB-UHFFFAOYSA-N 0.000 description 2
- SNVREIRUTHXNKB-UHFFFAOYSA-N (4-chlorophenyl)-(5-methoxy-2,3-dimethylindol-1-yl)methanone Chemical compound CC1=C(C)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 SNVREIRUTHXNKB-UHFFFAOYSA-N 0.000 description 2
- WZVVERCKBWMQLN-UHFFFAOYSA-N (4-chlorophenyl)-(5-methoxy-3-methylindol-1-yl)methanone Chemical compound C1=C(C)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 WZVVERCKBWMQLN-UHFFFAOYSA-N 0.000 description 2
- FQHCPFMTXFJZJS-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine;hydrochloride Chemical compound Cl.COC1=CC=C(NN)C=C1 FQHCPFMTXFJZJS-UHFFFAOYSA-N 0.000 description 2
- UPYOOGDANMQNRS-UHFFFAOYSA-N 4-chloro-n-phenylbenzohydrazide Chemical compound C=1C=CC=CC=1N(N)C(=O)C1=CC=C(Cl)C=C1 UPYOOGDANMQNRS-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000009838 combustion analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- KCBLJONCRXKBSE-UHFFFAOYSA-N (3-benzyl-5-methoxy-2-methylindol-1-yl)-(4-chlorophenyl)methanone Chemical compound ClC1=CC=C(C(=O)N2C(=C(C3=CC(=CC=C23)OC)CC2=CC=CC=C2)C)C=C1 KCBLJONCRXKBSE-UHFFFAOYSA-N 0.000 description 1
- HMHWNJGOHUYVMD-UHFFFAOYSA-N (4-methylanilino)azanium;chloride Chemical compound Cl.CC1=CC=C(NN)C=C1 HMHWNJGOHUYVMD-UHFFFAOYSA-N 0.000 description 1
- XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 description 1
- SICBLYCPRWNHHP-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)C1=CC=C(OC)C=C1 SICBLYCPRWNHHP-UHFFFAOYSA-N 0.000 description 1
- ZEDUQJSNLAZAPN-UHFFFAOYSA-N 1-[2,3-bis(4-methoxyphenyl)indol-1-yl]ethanone Chemical compound C(C)(=O)N1C(=C(C2=CC=CC=C12)C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC ZEDUQJSNLAZAPN-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- WFXUZRHBGGWGMD-UHFFFAOYSA-N 4-(diethylamino)butan-2-one hydrochloride Chemical compound Cl.CCN(CC)CCC(C)=O WFXUZRHBGGWGMD-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- IURNVVIQOMTXSM-UHFFFAOYSA-N 4-chloro-n-(4-methoxyphenyl)benzohydrazide Chemical compound C1=CC(OC)=CC=C1N(N)C(=O)C1=CC=C(Cl)C=C1 IURNVVIQOMTXSM-UHFFFAOYSA-N 0.000 description 1
- ANYDSWOBDUWVHE-UHFFFAOYSA-N 4-chloro-n-(4-methoxyphenyl)benzohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N(N)C(=O)C1=CC=C(Cl)C=C1 ANYDSWOBDUWVHE-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- WDZPEMMIFPWTCP-UHFFFAOYSA-N CC(NC1=CC=CC(C(C2(C=CC=CC2)Cl)=O)=C11)=C1C1=CC=CC=C1 Chemical compound CC(NC1=CC=CC(C(C2(C=CC=CC2)Cl)=O)=C11)=C1C1=CC=CC=C1 WDZPEMMIFPWTCP-UHFFFAOYSA-N 0.000 description 1
- NINDSTJEOQWSDU-UHFFFAOYSA-N CC1=C(CCNC2=CC=CC=C2)C2=CC(OC)=CC=C2N1C(C1=CC=C(C)C=C1)=O Chemical compound CC1=C(CCNC2=CC=CC=C2)C2=CC(OC)=CC=C2N1C(C1=CC=C(C)C=C1)=O NINDSTJEOQWSDU-UHFFFAOYSA-N 0.000 description 1
- NHNVFXVJBGLVMR-UHFFFAOYSA-N ClC1=CC=C(C(=O)C=2NC3=CC=C(C=C3C2C)OC)C=C1 Chemical compound ClC1=CC=C(C(=O)C=2NC3=CC=C(C=C3C2C)OC)C=C1 NHNVFXVJBGLVMR-UHFFFAOYSA-N 0.000 description 1
- QMKPYFFFSJWAJN-UHFFFAOYSA-N ClC1=CC=C(C(=O)N2C(=C(C3=CC(=CC=C23)OC)C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)C=C1 Chemical compound ClC1=CC=C(C(=O)N2C(=C(C3=CC(=CC=C23)OC)C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)C=C1 QMKPYFFFSJWAJN-UHFFFAOYSA-N 0.000 description 1
- BNQJXPSFTFGFQE-UHFFFAOYSA-N ClC1=CC=C(C(=O)N2C(=C(C3=CC=CC=C23)C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)C=C1 Chemical compound ClC1=CC=C(C(=O)N2C(=C(C3=CC=CC=C23)C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC)C=C1 BNQJXPSFTFGFQE-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D209/08—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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP191666 | 1966-01-13 | ||
| JP1623766 | 1966-03-15 | ||
| JP2164666 | 1966-04-05 | ||
| JP2217866 | 1966-04-07 | ||
| JP4633566 | 1966-07-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1620442A1 DE1620442A1 (de) | 1970-04-23 |
| DE1620442B2 DE1620442B2 (de) | 1974-11-14 |
| DE1620442C3 true DE1620442C3 (de) | 1975-07-03 |
Family
ID=27518188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1620442A Expired DE1620442C3 (de) | 1966-01-13 | 1966-12-30 | Verfahren zur Herstellung von 1-Acylindolverbindungen |
Country Status (10)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160862A (en) * | 1972-06-12 | 1979-07-10 | Sterling Drug Inc. | 1-Acyl-3-(amino-lower-alkyl)indoles |
| GB1374414A (en) * | 1972-06-12 | 1974-11-20 | Sterling Drug Inc | 1-acyl-3-amino-alkyl-indoles and their preparation |
| US3936464A (en) * | 1974-10-25 | 1976-02-03 | American Cyanamid Company | 1-Acyl-3-[2-(4-phenyl-1-piperidinyl)ethyl]indolines |
| DE2926472A1 (de) * | 1979-06-30 | 1981-01-15 | Thomae Gmbh Dr K | Neue benzoylderivate, deren herstellung und deren verwendung als arzneimittel |
| HU208421B (en) * | 1988-10-18 | 1993-10-28 | Pfizer | Process for producing starting materials for producing 3-acyl-2-oxindol-carboxamides ofantiphlogistic activity |
| US5734108A (en) * | 1992-04-10 | 1998-03-31 | Walker; Dana A. | System for sensing shaft displacement and strain |
| WO1993023374A1 (en) * | 1992-05-08 | 1993-11-25 | Otsuka Pharmaceutical Factory, Inc. | Indole derivative |
| US5880137A (en) * | 1996-04-19 | 1999-03-09 | American Home Products Corporation | 2-phenyl-1- 4-(amino-1-yl-alk-1-ynyl)-benzyl!-1H-indol-5-ols as estrogenic agents |
| US6069153A (en) * | 1998-05-12 | 2000-05-30 | American Home Products Corporation | Indenoindoles and benzocarbazoles as estrogenic agents |
| US6479535B1 (en) | 1998-05-15 | 2002-11-12 | Wyeth | 2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole and estrogen formulations |
| US6159959A (en) * | 1999-05-06 | 2000-12-12 | American Home Products Corporation | Combined estrogen and antiestrogen therapy |
| JP2004513076A (ja) | 2000-07-25 | 2004-04-30 | メルク エンド カムパニー インコーポレーテッド | 糖尿病治療で有用なｎ−置換インドール類 |
| CN103012242B (zh) * | 2012-12-31 | 2014-12-17 | 北京大学深圳研究生院 | 一种3位取代吲哚衍生物的制备方法 |
-
1966
- 1966-12-28 US US605171A patent/US3564009A/en not_active Expired - Lifetime
- 1966-12-30 GB GB58375/66A patent/GB1168450A/en not_active Expired
- 1966-12-30 DE DE1620442A patent/DE1620442C3/de not_active Expired
-
1967
- 1967-01-05 AT AT15867A patent/AT266821B/de active
- 1967-01-09 SE SE273/67A patent/SE307580B/xx unknown
- 1967-01-10 CS CS217A patent/CS151445B2/cs unknown
- 1967-01-12 NL NL676700456A patent/NL145853B/xx unknown
- 1967-01-12 CH CH44367A patent/CH484110A/fr not_active IP Right Cessation
- 1967-01-12 BE BE692519D patent/BE692519A/xx unknown
- 1967-01-12 FR FR90858A patent/FR1513575A/fr not_active Expired
- 1967-03-14 FR FR98692A patent/FR6286M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1513575A (fr) | 1968-02-16 |
| SE307580B (US06525083-20030225-C00028.png) | 1969-01-13 |
| NL145853B (nl) | 1975-05-15 |
| US3564009A (en) | 1971-02-16 |
| AT266821B (de) | 1968-12-10 |
| CH484110A (fr) | 1970-01-15 |
| BE692519A (US06525083-20030225-C00028.png) | 1967-06-16 |
| GB1168450A (en) | 1969-10-22 |
| DE1620442B2 (de) | 1974-11-14 |
| DE1620442A1 (de) | 1970-04-23 |
| CS151445B2 (US06525083-20030225-C00028.png) | 1973-10-19 |
| FR6286M (US06525083-20030225-C00028.png) | 1968-09-02 |
| NL6700456A (US06525083-20030225-C00028.png) | 1967-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |