CH506543A - Verfahren zur Herstellung von neuen 1,2,3,4,5,6-Hexahydroazepino (4,5-b)indolen - Google Patents

Verfahren zur Herstellung von neuen 1,2,3,4,5,6-Hexahydroazepino (4,5-b)indolen

Info

Publication number: CH506543A
Authority: CH; Switzerland
Prior art keywords: hhai; formula; benzyl; hydrochloride; mixture
Prior art date: 1966-05-10

Application number

CH637567A

Other languages

German (de)

English (en)

Inventor

Boling Jr Hester Jackson

Original Assignee

Upjohn Co

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.)

1966-05-10

Filing date

1967-05-05

Publication date

1971-04-30

1967-05-05 Application filed by Upjohn Co filed Critical Upjohn Co

1971-04-30 Publication of CH506543A publication Critical patent/CH506543A/de

Links

238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 10
NGUNYFTXLWTSNC-UHFFFAOYSA-N 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole Chemical class C1CNCCC2=C1C1=CC=CC=C1N2 NGUNYFTXLWTSNC-UHFFFAOYSA-N 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 91
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 88
239000000203 mixture Substances 0.000 claims description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 48
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 42
238000004458 analytical method Methods 0.000 claims description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
CFZRTDHGRHTNHP-UHFFFAOYSA-N 1-benzoylazepan-4-one Chemical compound C=1C=CC=CC=1C(=O)N1CCCC(=O)CC1 CFZRTDHGRHTNHP-UHFFFAOYSA-N 0.000 claims description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
239000000463 material Substances 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 24
239000003054 catalyst Substances 0.000 claims description 23
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 21
235000019253 formic acid Nutrition 0.000 claims description 21
238000001953 recrystallisation Methods 0.000 claims description 21
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
238000003756 stirring Methods 0.000 claims description 15
238000001914 filtration Methods 0.000 claims description 14
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 13
239000000284 extract Substances 0.000 claims description 12
239000000741 silica gel Substances 0.000 claims description 12
229910002027 silica gel Inorganic materials 0.000 claims description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
239000012312 sodium hydride Substances 0.000 claims description 11
229910000104 sodium hydride Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 7
229940067157 phenylhydrazine Drugs 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
229910052987 metal hydride Inorganic materials 0.000 claims description 5
150000004681 metal hydrides Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 5
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
SLUVIYDZZNFGFP-UHFFFAOYSA-N 3-benzylazepane Chemical compound C=1C=CC=CC=1CC1CCCCNC1 SLUVIYDZZNFGFP-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
229940073608 benzyl chloride Drugs 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000011877 solvent mixture Substances 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
150000001347 alkyl bromides Chemical class 0.000 claims description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
150000004694 iodide salts Chemical class 0.000 claims description 2
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 claims description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 2
238000010792 warming Methods 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
239000000243 solution Substances 0.000 description 53
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 24
-1 methoxy, ethoxy, propoxy Chemical group 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000000706 filtrate Substances 0.000 description 21
239000012299 nitrogen atmosphere Substances 0.000 description 19
239000007787 solid Substances 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
229960000583 acetic acid Drugs 0.000 description 14
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
239000012280 lithium aluminium hydride Substances 0.000 description 13
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
239000000126 substance Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000005457 ice water Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000005909 Kieselgur Substances 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000012267 brine Substances 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000012043 crude product Substances 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
238000000855 fermentation Methods 0.000 description 4
230000004151 fermentation Effects 0.000 description 4
150000003840 hydrochlorides Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
KZLCCMBSJDXNDG-UHFFFAOYSA-N azepan-1-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCCCCC1 KZLCCMBSJDXNDG-UHFFFAOYSA-N 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
240000002439 Sorghum halepense Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001860 citric acid derivatives Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
150000002475 indoles Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000002688 maleic acid derivatives Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
150000004031 phenylhydrazines Chemical class 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
150000003892 tartrate salts Chemical class 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000003643 water by type Substances 0.000 description 2
GHGPIPTUDQZJJS-UHFFFAOYSA-N (2-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Cl GHGPIPTUDQZJJS-UHFFFAOYSA-N 0.000 description 1
KJGFNDCSTWGUDT-UHFFFAOYSA-N (2-methylanilino)azanium;chloride Chemical compound Cl.CC1=CC=CC=C1NN KJGFNDCSTWGUDT-UHFFFAOYSA-N 0.000 description 1
JYPNYAHCNKRLHG-UHFFFAOYSA-N (4-ethylphenyl)hydrazine Chemical compound CCC1=CC=C(NN)C=C1 JYPNYAHCNKRLHG-UHFFFAOYSA-N 0.000 description 1
FEKUXLUOKFSMRO-UHFFFAOYSA-N (4-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(F)C=C1 FEKUXLUOKFSMRO-UHFFFAOYSA-N 0.000 description 1
KNJRLTDIYBQRPE-UHFFFAOYSA-N (4-hydroxyazepan-1-yl)-phenylmethanone Chemical compound C1CC(O)CCCN1C(=O)C1=CC=CC=C1 KNJRLTDIYBQRPE-UHFFFAOYSA-N 0.000 description 1
PVRSIFAEUCUJPK-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine Chemical compound COC1=CC=C(NN)C=C1 PVRSIFAEUCUJPK-UHFFFAOYSA-N 0.000 description 1
FTNZYGDTGODLJK-UHFFFAOYSA-N (4-propoxyphenyl)hydrazine Chemical compound CCCOC1=CC=C(NN)C=C1 FTNZYGDTGODLJK-UHFFFAOYSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010001488 Aggression Diseases 0.000 description 1
241000743987 Alopecurus pratensis Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
244000052363 Cynodon dactylon Species 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
YEWGIGCYIAMFMA-UHFFFAOYSA-N LSM-2007 Chemical compound C1C2=CC=CC=C2CCN(C)CCC2=C1NC1=CC=CC=C21 YEWGIGCYIAMFMA-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
240000003461 Setaria viridis Species 0.000 description 1
235000002248 Setaria viridis Nutrition 0.000 description 1
235000010086 Setaria viridis var. viridis Nutrition 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
229920002472 Starch Polymers 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001262 acyl bromides Chemical class 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
238000005273 aeration Methods 0.000 description 1
208000012761 aggressive behavior Diseases 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000002539 anti-aggressive effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000002830 appetite depressant Substances 0.000 description 1
GLZXFITXXAMCRJ-UHFFFAOYSA-N azepin-4-one Chemical compound O=C1C=CC=NC=C1 GLZXFITXXAMCRJ-UHFFFAOYSA-N 0.000 description 1
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
230000001914 calming effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
CCZOANFFMASREE-UHFFFAOYSA-N cyclohexane;sulfamic acid Chemical compound NS(O)(=O)=O.C1CCCCC1 CCZOANFFMASREE-UHFFFAOYSA-N 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
HECSHXUNOVTAIJ-UHFFFAOYSA-N hydron;(2-methoxyphenyl)hydrazine;chloride Chemical compound Cl.COC1=CC=CC=C1NN HECSHXUNOVTAIJ-UHFFFAOYSA-N 0.000 description 1
GMXFZBZOVZOYNQ-UHFFFAOYSA-N hydron;(3-methoxyphenyl)hydrazine;chloride Chemical compound Cl.COC1=CC=CC(NN)=C1 GMXFZBZOVZOYNQ-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
150000002942 palmitic acid derivatives Chemical class 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
KEAYESYHFKHZAL-OUBTZVSYSA-N sodium-24 Chemical compound [24Na] KEAYESYHFKHZAL-OUBTZVSYSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003567 thiocyanates Chemical class 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
238000009423 ventilation Methods 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Indole Compounds (AREA)

CH637567A 1966-05-10 1967-05-05 Verfahren zur Herstellung von neuen 1,2,3,4,5,6-Hexahydroazepino (4,5-b)indolen CH506543A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US54888066A	1966-05-10	1966-05-10

Publications (1)

Publication Number	Publication Date
CH506543A true CH506543A (de)	1971-04-30

Family

ID=24190763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH637567A CH506543A (de)	1966-05-10	1967-05-05	Verfahren zur Herstellung von neuen 1,2,3,4,5,6-Hexahydroazepino (4,5-b)indolen

Country Status (9)

Country	Link
BE (1)	BE698268A (fr)
CH (1)	CH506543A (fr)
DE (1)	DE1695943A1 (fr)
ES (1)	ES340258A1 (fr)
FR (1)	FR6699M (fr)
GB (2)	GB1180616A (fr)
GR (1)	GR35044B (fr)
IL (2)	IL36801A (fr)
NL (1)	NL6706513A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003099821A1 (fr) *	2002-05-24	2003-12-04	X-Ceptor Therapeutics, Inc.	Derives d'azepinoindole et de pyridoindole utilises comme agents pharmaceutiques
WO2005056554A3 (fr) *	2003-12-02	2005-08-18	X Ceptor Therapeutics Inc	Derives d'azepinoindole en tant qu'agents pharmaceutiques
EP1648408A4 (fr) *	2003-07-23	2006-11-29	Exelixis Inc	Derives de l'azepine comme agents pharmaceutiques

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2029828B (en) *	1978-08-24	1983-04-27	Omnium Chimique Sa	Vincadifformine derivatives
FR2663935A1 (fr) *	1990-06-27	1992-01-03	Adir	Nouveaux 1,2,3,4,5,6-hexahydroazepino [4,5-b] indoles et 1,2,3,4-tetrahydrobethacarbolines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent.
MY122278A (en)	1999-07-19	2006-04-29	Upjohn Co	1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position
US7030109B2 (en)	1999-07-19	2006-04-18	Pharmacia & Upjohn Company	1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position
WO2002004456A1 (fr) *	2000-07-06	2002-01-17	Pharmacia & Upjohn Company	2,3,7,8,9,10,11,12-octahydroazepino[4,5-b]pyrano[3,2-e]indoles substitutes
JP2004509894A (ja) *	2000-09-20	2004-04-02	ファルマシア・アンド・アップジョン・カンパニー	置換アゼピノ［４，５−ｂ］インドリン誘導体
WO2023092045A1 (fr)	2021-11-17	2023-05-25	Terran Biosciences, Inc.	Sels et formes solides de tabernanthalog

1967
- 1967-04-10 GR GR670135044A patent/GR35044B/el unknown
- 1967-04-11 IL IL3680167A patent/IL36801A/en unknown
- 1967-04-11 IL IL2777667A patent/IL27776A/en unknown
- 1967-04-17 GB GB4488369A patent/GB1180616A/en not_active Expired
- 1967-04-17 GB GB1757867A patent/GB1180615A/en not_active Expired
- 1967-05-05 CH CH637567A patent/CH506543A/de not_active IP Right Cessation
- 1967-05-08 ES ES340258A patent/ES340258A1/es not_active Expired
- 1967-05-09 DE DE19671695943 patent/DE1695943A1/de active Pending
- 1967-05-10 BE BE698268D patent/BE698268A/xx unknown
- 1967-05-10 NL NL6706513A patent/NL6706513A/xx unknown
- 1967-08-08 FR FR117261A patent/FR6699M/fr not_active Expired

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003099821A1 (fr) *	2002-05-24	2003-12-04	X-Ceptor Therapeutics, Inc.	Derives d'azepinoindole et de pyridoindole utilises comme agents pharmaceutiques
US7485634B2 (en)	2002-05-24	2009-02-03	Exelixis, Inc.	Azepinoindole and pyridoindole derivatives as pharmaceutical agents
US7595311B2 (en)	2002-05-24	2009-09-29	Exelixis, Inc.	Azepinoindole derivatives as pharmaceutical agents
EP1648408A4 (fr) *	2003-07-23	2006-11-29	Exelixis Inc	Derives de l'azepine comme agents pharmaceutiques
US8466143B2 (en)	2003-07-23	2013-06-18	Exelixis, Inc.	Azepine derivatives as pharmaceutical agents
WO2005056554A3 (fr) *	2003-12-02	2005-08-18	X Ceptor Therapeutics Inc	Derives d'azepinoindole en tant qu'agents pharmaceutiques
RU2423363C2 (ru) *	2003-12-02	2011-07-10	Экселиксис, Инк.	Производные азепиноиндола в качестве фармацевтических средств

Also Published As

Publication number	Publication date
BE698268A (fr)	1967-11-10
FR6699M (fr)	1969-02-10
NL6706513A (fr)	1967-11-13
DE1695943A1 (de)	1971-05-13
GB1180616A (en)	1970-02-04
IL36801A (en)	1971-11-29
GB1180615A (en)	1970-02-04
GR35044B (el)	1968-07-31
IL27776A (en)	1971-11-29
ES340258A1 (es)	1968-06-01

Legal Events

Date	Code	Title	Description
1974-12-13	PL	Patent ceased

Publication	Publication Date	Title
DE60001307T2 (de)	2003-12-11	Pyridopyranoazepinderivate, ihre herstellung und therapeutische verwendung
CH643835A5 (de)	1984-06-29	5h-2,3-benzodiazepin-derivate und verfahren zu ihrer herstellung.
DE2125634A1 (de)	1972-01-05	Verfahren zur Herstellung von neuen Cycloheptenderivaten
DE3023626A1 (de)	1981-01-08	1,9-dihydroxyoctahydrobenzo eckige klammer auf c eckige klammer zu chinoline und 1-hydroxyhexahydrobenzo eckige klammer auf c eckige klammer zu chinolin-9 (8h)- one als antiemetika
DE2424811C3 (de)	1981-08-20	Pyrido-benzodiazepinone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE1445845A1 (de)	1969-02-06	Neue Benzomorphane und Verfahren zu ihrer Herstellung
CH622019A5 (en)	1981-03-13	Process for the preparation of aminotriazolobenzodiazepines
US3839357A (en)	1974-10-01	1,2,3,4,5,6-hexahydroazepino(4,5-b)indoles
DE1695943A1 (de)	1971-05-13	Verfahren zur Herstellung von neuen 1,2,3,4,5,6-Hexahydroazepino(4,5-b)indolen und deren Saeureanlagerungssalzen
CH511838A (de)	1971-08-31	Verfahren zur Herstellung von neuen Indolderivaten
DE2722416A1 (de)	1978-11-30	Neue thiazolo-pyridine
DE1065422B (de)	1959-09-17	Verfahren zur Herstellung von Lysergsäure deren N-Derivaten und Estern
DE2125926A1 (de)	1972-01-27	Indoldenvate
DE3300522C2 (fr)	1992-01-09
EP0017727A1 (fr)	1980-10-29	Composés diazatricycliques polysubstitués, procédés pour leur préparation et compositions pharmaceutiques les contenant
DD283823A5 (de)	1990-10-24	Verfahren zur herstellung heterotetracyclischer lactamderivate
DE3875031T2 (de)	1993-03-04	Substituierte dibenzocycloheptenimine.
DE1914981A1 (de)	1970-09-17	Verfahren zur Herstellung heterocyclischer Verbindungen
DE2100654A1 (de)	1971-07-22	Derivate von 2,3-Dihydrobenz- eckige Klammer auf eckige Klammer zu 1,4 oxazepin, deren Salze und deren Herstellung
DE2357253A1 (de)	1975-05-22	Neue chinolinderivate
DE1545947A1 (de)	1969-12-11	Verfahren zur Herstellung von Iminodibenzyl-Derivaten
DE1795758A1 (de)	1974-10-10	Verfahren zur herstellung von 5hydroxy-5-phenyl-2,3-dihydro-5h-imidazo eckige klammer auf 2,1-a eckige klammer zu isoindolen
DE1770722A1 (de)	1972-01-13	1,4,9,10-Tetra-benzo[5,6]cyclohepta[1,2-d]4-one und Verfahren zu ihrer Herstellung
AT374201B (de)	1984-03-26	Verfahren zur herstellung von neuen isochinolinverbindungen
DE1445845C (de)	1971-11-11	5-Phenyl-6,7-benzomorphane