DE2305496A1 - Neue dibenzocyclohepten-derivate und verfahren zu ihrer herstellung - Google Patents
Neue dibenzocyclohepten-derivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2305496A1 DE2305496A1 DE2305496A DE2305496A DE2305496A1 DE 2305496 A1 DE2305496 A1 DE 2305496A1 DE 2305496 A DE2305496 A DE 2305496A DE 2305496 A DE2305496 A DE 2305496A DE 2305496 A1 DE2305496 A1 DE 2305496A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- dibenzo
- dihydro
- carbon atoms
- imino
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 alkyl radical Chemical class 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910021529 ammonia Inorganic materials 0.000 claims description 15
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 15
- 239000011707 mineral Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052736 halogen Chemical group 0.000 claims description 10
- 150000007522 mineralic acids Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- SWQHAYQRODJNDS-UHFFFAOYSA-N N=C1CC2=C(CC3=C1C=CC=C3)C=CC=C2 Chemical compound N=C1CC2=C(CC3=C1C=CC=C3)C=CC=C2 SWQHAYQRODJNDS-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002521 alkyl halide group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- YUQPDXQYSSSHJD-UHFFFAOYSA-N 16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaen-8-one Chemical compound C12=CC=CC=C2C(=O)C2C3=CC=CC=C3C1N2 YUQPDXQYSSSHJD-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 2
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 116
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 47
- 239000000203 mixture Substances 0.000 description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 32
- 235000019341 magnesium sulphate Nutrition 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
- 239000012071 phase Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- 229910001923 silver oxide Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IZAKUVQRXVRYER-UHFFFAOYSA-N 2-bromotricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene-9,10-dione Chemical compound O=C1C(=O)C2=CC=CC=C2C(Br)C2=CC=CC=C21 IZAKUVQRXVRYER-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- PFFGUTFSPWUIOT-UHFFFAOYSA-N (+-)-10,11-dihydro-12-methyl-5h-dibenzo(a,d)cyclohepten-5,10-imine Chemical compound C12=CC=CC=C2C2N(C)C1C1=CC=CC=C1C2 PFFGUTFSPWUIOT-UHFFFAOYSA-N 0.000 description 1
- SAWOLAINNGNEPL-UHFFFAOYSA-N (+-)-10,11-dihydro-5h-dibenzo(a,d)cyclohepten-5,10-imine Chemical compound C12=CC=CC=C2CC2C3=CC=CC=C3C1N2 SAWOLAINNGNEPL-UHFFFAOYSA-N 0.000 description 1
- ZICXADCUXFAAOU-UHFFFAOYSA-N (+-)-10,11-dihydro-5h-dibenzo(a,d)cyclohepten-5,10-imine-12-ethanol Chemical compound C12=CC=CC=C2C2N(CCO)C1C1=CC=CC=C1C2 ZICXADCUXFAAOU-UHFFFAOYSA-N 0.000 description 1
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- MGHDAAZPFFNACM-UHFFFAOYSA-N 6,11-dihydrodibenzo[2,1-a:2',1'-e][7]annulen-5-one Chemical compound O=C1CC2=CC=CC=C2CC2=CC=CC=C12 MGHDAAZPFFNACM-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- 229940087675 benzilic acid Drugs 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- VACOMSNNWGXHSF-UHFFFAOYSA-N chloro(dimethylphosphoryl)methane Chemical compound CP(C)(=O)CCl VACOMSNNWGXHSF-UHFFFAOYSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000008508 dibenzocycloheptenes Chemical class 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WRVKQGHUIGYJAF-UHFFFAOYSA-N dl-12-(methylaminoacetyl)-10,11-dihydro-5,10-imino-(5h)-dibenzo(a,d)cycloheptene Chemical compound C12=CC=CC=C2C2N(C(=O)CNC)C1C1=CC=CC=C1C2 WRVKQGHUIGYJAF-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7203778A FR2170861B1 (en, 2012) | 1972-02-04 | 1972-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2305496A1 true DE2305496A1 (de) | 1973-08-09 |
Family
ID=9093003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2305496A Pending DE2305496A1 (de) | 1972-02-04 | 1973-02-05 | Neue dibenzocyclohepten-derivate und verfahren zu ihrer herstellung |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US3892756A (en, 2012) |
| JP (1) | JPS4886899A (en, 2012) |
| AT (1) | AT327212B (en, 2012) |
| AU (1) | AU468600B2 (en, 2012) |
| BE (1) | BE794904A (en, 2012) |
| CA (1) | CA1019732A (en, 2012) |
| CH (2) | CH565176A5 (en, 2012) |
| DD (1) | DD106837A5 (en, 2012) |
| DE (1) | DE2305496A1 (en, 2012) |
| DK (1) | DK136650B (en, 2012) |
| ES (1) | ES411262A1 (en, 2012) |
| FR (1) | FR2170861B1 (en, 2012) |
| GB (1) | GB1405711A (en, 2012) |
| HU (1) | HU166618B (en, 2012) |
| IL (1) | IL41403A (en, 2012) |
| NL (1) | NL7301610A (en, 2012) |
| SE (1) | SE405974B (en, 2012) |
| SU (2) | SU651704A3 (en, 2012) |
| ZA (1) | ZA73658B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252810A (en) * | 1978-11-15 | 1981-02-24 | Merck & Co., Inc. | 9,10-Dihydro-4H-benzo[4,5]cyclohepta [1,2-b]thiophen-4,9-imines |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794904A (fr) * | 1972-02-04 | 1973-08-02 | Roussel Uclaf | Nouveaux derives du dibenzocycloheptene et leur preparation |
| US4123546A (en) * | 1977-07-01 | 1978-10-31 | E. I. Du Pont De Nemours And Company | Antidepressant compounds |
| US4414154A (en) * | 1977-09-19 | 1983-11-08 | Merck & Co. Inc. | Dibenzo[a,d]cycloocten-5,12-imines |
| NL7808848A (nl) * | 1977-09-19 | 1979-03-21 | Merck & Co Inc | Dibenzoa.dcyclo-octeen-5.12-(en 6.12)-iminen. |
| NL191488C (nl) * | 1977-09-19 | 1995-08-04 | Merck & Co Inc | Op de 5-plaats gesubstitueerde 10,11-dihydro-5H-dibenzo£a,d|cyclohepteen-5,10-iminen en farmaceutische preparaten die deze bevatten. |
| US4399141A (en) * | 1977-09-19 | 1983-08-16 | Merck & Co., Inc. | 5-Alkyl or hydroxyalkyl substituted-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines and anticonvulsant use thereof |
| IL56112A0 (en) * | 1977-12-15 | 1979-03-12 | Merck & Co Inc | Imino-bridged benzocycloheptapyridines |
| US4256889A (en) * | 1978-11-09 | 1981-03-17 | Merck & Co., Inc. | Process for the preparation of imino-bridged benzocycloheptapyridines |
| US4232158A (en) * | 1979-06-04 | 1980-11-04 | Merck & Co., Inc. | 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines |
| US4870079A (en) * | 1986-09-08 | 1989-09-26 | Merck & Co., Inc. | Derivatives of 5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine |
| GB8719199D0 (en) * | 1987-08-13 | 1987-09-23 | Merck Sharp & Dohme | Chemical compounds |
| US5011834A (en) * | 1989-04-14 | 1991-04-30 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | PCP receptor ligands and the use thereof |
| US5688789A (en) * | 1989-04-14 | 1997-11-18 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | PCP receptor ligands and the use thereof |
| ATE137752T1 (de) * | 1989-05-09 | 1996-05-15 | Us Health | 5-aminocarbonyl-5h-dibenzo-a,d>cyclohepten-5,10 imine zur behandlung von epilepsie und kokainsucht |
| US5196415A (en) * | 1989-05-09 | 1993-03-23 | The United States Of America As Represented By The Department Of Health And Human Services | 5-aminocarbonyl-5H-dibenzo[a.d]cyclohepten-5,10-imines for treatment of epilepsy and cocaine addiction |
| US5064831A (en) * | 1990-09-14 | 1991-11-12 | Bristol-Myers Squibb Co. | Naphthothiophenimines for treating neuronal disorders caused by ischemia |
| US5579543A (en) * | 1994-05-12 | 1996-12-03 | Easy Lift Products, Inc. | Method for transferring a patient between a bed and a bath tub |
| US5666677A (en) * | 1994-05-12 | 1997-09-16 | Easy Lift Care Products, Inc. | Bath tub assembly |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2524856A (en) * | 1950-10-10 | Wperido-phenanthrene derivatives | ||
| US3597433A (en) * | 1968-08-19 | 1971-08-03 | Ayerst Mckenna & Harrison | 10,11 - dihydro - 5,10 - (iminomethano)-5h-dibenzo(a,d)cycloheptene and derivatives thereof |
| NL7007464A (en, 2012) * | 1969-05-30 | 1970-12-02 | ||
| BE790673A (fr) * | 1971-10-29 | 1973-04-27 | Riker Laboratories Inc | Dibenzobicyclo (3.2.1) octadienes substitues en positions 8 |
| BE794904A (fr) * | 1972-02-04 | 1973-08-02 | Roussel Uclaf | Nouveaux derives du dibenzocycloheptene et leur preparation |
-
0
- BE BE794904D patent/BE794904A/xx unknown
-
1972
- 1972-02-04 FR FR7203778A patent/FR2170861B1/fr not_active Expired
-
1973
- 1973-01-26 IL IL41403A patent/IL41403A/en unknown
- 1973-01-29 CH CH1553074A patent/CH565176A5/xx not_active IP Right Cessation
- 1973-01-29 CH CH124673A patent/CH567018A5/xx not_active IP Right Cessation
- 1973-01-30 ZA ZA730658A patent/ZA73658B/xx unknown
- 1973-01-30 US US328006A patent/US3892756A/en not_active Expired - Lifetime
- 1973-02-02 HU HURO702A patent/HU166618B/hu unknown
- 1973-02-02 AU AU51755/73A patent/AU468600B2/en not_active Expired
- 1973-02-02 SE SE7301485A patent/SE405974B/xx unknown
- 1973-02-02 SU SU731878076A patent/SU651704A3/ru active
- 1973-02-02 JP JP48013013A patent/JPS4886899A/ja active Pending
- 1973-02-03 ES ES411262A patent/ES411262A1/es not_active Expired
- 1973-02-05 DD DD169161A patent/DD106837A5/xx unknown
- 1973-02-05 CA CA162,927A patent/CA1019732A/en not_active Expired
- 1973-02-05 DE DE2305496A patent/DE2305496A1/de active Pending
- 1973-02-05 GB GB562473A patent/GB1405711A/en not_active Expired
- 1973-02-05 NL NL7301610A patent/NL7301610A/xx not_active Application Discontinuation
- 1973-02-05 DK DK58873AA patent/DK136650B/da unknown
- 1973-02-05 AT AT99073*#A patent/AT327212B/de not_active IP Right Cessation
-
1974
- 1974-12-18 SU SU7402084652A patent/SU574154A3/ru active
-
1975
- 1975-04-14 US US05/568,148 patent/US4009273A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252810A (en) * | 1978-11-15 | 1981-02-24 | Merck & Co., Inc. | 9,10-Dihydro-4H-benzo[4,5]cyclohepta [1,2-b]thiophen-4,9-imines |
Also Published As
| Publication number | Publication date |
|---|---|
| BE794904A (fr) | 1973-08-02 |
| US3892756A (en) | 1975-07-01 |
| ES411262A1 (es) | 1976-04-16 |
| SE405974B (sv) | 1979-01-15 |
| HU166618B (en, 2012) | 1975-04-28 |
| SU574154A3 (ru) | 1977-09-25 |
| NL7301610A (en, 2012) | 1973-08-07 |
| AU468600B2 (en) | 1976-01-15 |
| CH565176A5 (en, 2012) | 1975-08-15 |
| IL41403A0 (en) | 1973-03-30 |
| IL41403A (en) | 1977-06-30 |
| GB1405711A (en) | 1975-09-10 |
| DD106837A5 (en, 2012) | 1974-07-05 |
| CA1019732A (en) | 1977-10-25 |
| DK136650B (da) | 1977-11-07 |
| SU651704A3 (ru) | 1979-03-05 |
| ZA73658B (en) | 1974-03-27 |
| FR2170861A1 (en, 2012) | 1973-09-21 |
| DK136650C (en, 2012) | 1978-04-10 |
| JPS4886899A (en, 2012) | 1973-11-15 |
| US4009273A (en) | 1977-02-22 |
| CH567018A5 (en, 2012) | 1975-09-30 |
| AT327212B (de) | 1976-01-26 |
| AU5175573A (en) | 1974-08-08 |
| FR2170861B1 (en, 2012) | 1975-04-25 |
| ATA99073A (de) | 1975-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2305496A1 (de) | Neue dibenzocyclohepten-derivate und verfahren zu ihrer herstellung | |
| DE2614406C2 (en, 2012) | ||
| DE2144490A1 (de) | Neue heterocyclische Verbindungen und Verfahren zu deren Herstellung | |
| EP0006524A1 (de) | Neue Tetrahydropyridin- und Piperidinderivate und deren Säureadditionssalze, Verfahren zu deren Herstellung und solche enthaltende pharmazeutische Zusammensetzungen | |
| DE2011806A1 (de) | Neue trieyclisehe Verbindungen | |
| DE2851028A1 (de) | Neue indolo eckige klammer auf 2.3-a eckige klammer zu chinolizidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitung | |
| DE1620198A1 (de) | Heterozyklische Verbindungen | |
| DE2256392A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| AT200578B (de) | Verfahren zur Herstellung von neuen N-Aminoalkylderivaten von Azepinen | |
| DE2051962A1 (de) | Benzimidazo eckige Klammer auf l,2d eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepin 6 (5H) one und Verfahren zu deren Her stellung | |
| DE1720033A1 (de) | Neue Indolderivate und Verfahren zu ihrer Herstellung | |
| CH616142A5 (en, 2012) | ||
| DE3217854A1 (de) | 1-amino-derivate von 1-(3',4'-methylendioxiphenyl)propan-2-ol, verfahren zu deren herstellung und sie enthaltende arzneimittel | |
| DE2114461A1 (de) | Neue Fluoren bzw Fluorenondenvate und Verfahren zur Herstellung derselben | |
| DE1493451A1 (de) | Verfahren zur Herstellung basischer Dibenzooxepin-bzw. Dibenzothiepin-Derivate und ihrer Salze | |
| DE2834372A1 (de) | Perhydronaphthalinpentolderivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel | |
| DE3520104A1 (de) | Naphthoxazine, ihre herstellung und verwendung | |
| DE2420168A1 (de) | Amino-substituierte piperidinderivate | |
| DE2230154A1 (de) | N-(heteroaryl-methyl)-6,14-endoaetheno7alpha-hydroxyalkyl-tetrahydro-nororipavine und -thebaine, deren hydrierungsprodukte und saeureadditionssalze sowie verfahren zu deren herstellung | |
| EP0137993B1 (de) | Neue 11-Piperazinyl-5H-imidazo[2,1-c][1,4]benzodiazepine, Verfahren zu ihrer Herstellung und Zwischenprodukte und erstere enthaltende Arzneimittel | |
| DE1933599A1 (de) | Chinolinderivate | |
| DE2618721C2 (de) | Benzo(b)-bicyclo[3,3,1]nonene, Verfahren zu deren Herstellung und pharmazeutische Mittel, die diese Verbindungen enthalten | |
| DE1228272B (de) | Verfahren zur Herstellung von 11-Aminoalkyldibenzo[b, f]thiepinen | |
| DE2139016A1 (de) | Neue organische Verbindungen und Verfahren zu deren Herstellung | |
| DE1965988A1 (de) | Verfahren zur Herstellung von neuen Derivaten des 5H-Dibenz[b,f]azepins |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |