CH623574A5 - - Google Patents
Download PDFInfo
- Publication number
- CH623574A5 CH623574A5 CH1287676A CH1287676A CH623574A5 CH 623574 A5 CH623574 A5 CH 623574A5 CH 1287676 A CH1287676 A CH 1287676A CH 1287676 A CH1287676 A CH 1287676A CH 623574 A5 CH623574 A5 CH 623574A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- acid addition
- formula
- dimethylaminopropyl
- addition salts
- Prior art date
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- -1 3-cyano-N- (N, N-dimethylaminopropyl) -iminodibenzyl Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 230000001430 anti-depressive effect Effects 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000013275 serotonin uptake Effects 0.000 claims description 3
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 206010010774 Constipation Diseases 0.000 claims 1
- 208000001871 Tachycardia Diseases 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 230000001078 anti-cholinergic effect Effects 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 206010013781 dry mouth Diseases 0.000 claims 1
- 201000003104 endogenous depression Diseases 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 230000006794 tachycardia Effects 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- QBSUAHGUFKVVTM-UHFFFAOYSA-N 1-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical group C1CC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 QBSUAHGUFKVVTM-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000008517 inhibition of serotonin uptake Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RDMBLKZGJCDETQ-UHFFFAOYSA-N C(#N)C(CCN=C(C1=CC=CC=C1)[ClH]CC1=CC=CC=C1)N(C)C Chemical compound C(#N)C(CCN=C(C1=CC=CC=C1)[ClH]CC1=CC=CC=C1)N(C)C RDMBLKZGJCDETQ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000011261 inert gas Substances 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
- 229960002510 mandelic acid Drugs 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- CPKISUMKCULUNR-UHFFFAOYSA-N 2-methoxy-2-oxoacetic acid Chemical compound COC(=O)C(O)=O CPKISUMKCULUNR-UHFFFAOYSA-N 0.000 description 1
- LJMSAUILRDVXCA-UHFFFAOYSA-N 2-methoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.COC(=O)C(O)=O LJMSAUILRDVXCA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FVLAVKHOGXWEIS-UHFFFAOYSA-N ClC(CCN=C(C1=CC=CC=C1)[ClH]CC1=CC=CC=C1)N(C)C Chemical compound ClC(CCN=C(C1=CC=CC=C1)[ClH]CC1=CC=CC=C1)N(C)C FVLAVKHOGXWEIS-UHFFFAOYSA-N 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
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- MJBHKOPXITTYCX-UHFFFAOYSA-N N=C(C1=CC=CC=C1)[ClH]CC1=CC=CC=C1 Chemical compound N=C(C1=CC=CC=C1)[ClH]CC1=CC=CC=C1 MJBHKOPXITTYCX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 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
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 210000004556 brain Anatomy 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
- 230000005587 bubbling Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 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
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 210000003568 synaptosome Anatomy 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
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/28—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a single bond between positions 10 and 11
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Priority Applications (38)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1287676A CH623574A5 ( ) | 1976-10-12 | 1976-10-12 | |
| FI772675A FI62531C (fi) | 1976-10-12 | 1977-09-09 | Foerfarande foer framstaellning av terapeutiskt anvaendbart 3-yan-n-(n n-dimetylamino-propyl)-iminodibensyl och syraadd itonssalter daerav |
| NLAANVRAGE7710194,A NL183943C (nl) | 1976-10-12 | 1977-09-16 | Werkwijze voor het bereiden van een geneesmiddel met een antidepressieve activiteit, alsmede werkwijze voor het bereiden van een 5-(n,n-dimethylaminopropyl)-10,11-dihydro-5h-dibenzo(b,f)azepine derivaat. |
| YU2209/77A YU40482B (en) | 1976-10-12 | 1977-09-19 | Process for obtining 3-cyano-n-(n,n-dimethylamino-propyl)-imino-dibenzyl |
| IT7728172A IT1143697B (it) | 1976-10-12 | 1977-09-30 | Composti triciclici in particolare 3 cian-n-(nmn dimetilammino-propil)-imminodibenzile,sali di addizione di detti composti e loro impiego farmaceutico,e procedimenti preparativi |
| CA288,106A CA1075688A (en) | 1976-10-12 | 1977-10-04 | Iminodibenzyl derivatives |
| AU29391/77A AU512561B2 (en) | 1976-10-12 | 1977-10-05 | 3-cyano N (N, N-dimethylamino-propyl) iminodibenzyl |
| ZA00775974A ZA775974B (en) | 1976-10-12 | 1977-10-05 | Tricyclic compounds |
| IL7753074A IL53074A (en) | 1976-10-12 | 1977-10-06 | 3-cyano-n-(dimethylaminopropyl)(b,f)dibenzazepin and its salts,their manufacture and novel intermediates thereof and pharmaceutical compositions containing them |
| NZ185378A NZ185378A (en) | 1976-10-12 | 1977-10-07 | 3-cyano-n-(n,n-dimethyl aminopropyl)-imino-dibenzyl and pharmaceutical compositions |
| PH20315A PH13371A (en) | 1976-10-12 | 1977-10-07 | 3-cyano-n-(n,n-dimethylaminopropyl)-iminodibenzyl compositions containing same and method |
| DE2745280A DE2745280C2 (de) | 1976-10-12 | 1977-10-07 | 3-Cyano-10,11-dihydro-5H-dibenz[b,f]azepin |
| IE2051/77A IE45709B1 (en) | 1976-10-12 | 1977-10-07 | Tricyclic compounds |
| LU7778280A LU78280A1 ( ) | 1976-10-12 | 1977-10-10 | |
| FR7730429A FR2367749A1 (fr) | 1976-10-12 | 1977-10-10 | Nouveaux composes tricycliques utiles comme medicaments |
| HU77HO2017A HU173607B (hu) | 1976-10-12 | 1977-10-10 | Sposob poluchenija novogo proizvodnogo dibenzazepina i ego solej |
| MC771263A MC1169A1 (fr) | 1976-10-12 | 1977-10-10 | Composes tricycliques |
| ES77463133A ES463133A1 (es) | 1976-10-12 | 1977-10-11 | Un procedimiento para la preparacion de 3-ciano-n(n,n-dime- tilamino-propil)-iminodibencilo |
| BE181609A BE859569A (fr) | 1976-10-12 | 1977-10-11 | Composes tricycliques |
| DK451477A DK153786C (da) | 1976-10-12 | 1977-10-11 | Analogifremgangsmaade til fremstilling af 3-cyan-n-(n,n-dimethylaminopropyl)-iminodibenzyl eller syreadditionssalte deraf |
| PT67142A PT67142B (pt) | 1976-10-12 | 1977-10-11 | Process for preparing tricyclic compounds |
| SE7711433A SE427557B (sv) | 1976-10-12 | 1977-10-11 | Forfarande for framstellning av 3-cyan-n-(n,n-dimetylamino-propyl)-iminodibensyl samt syraadditionssalter derav |
| GB42276/77A GB1583590A (en) | 1976-10-12 | 1977-10-11 | Tricycle compounds |
| US05/840,790 US4138482A (en) | 1976-10-12 | 1977-10-11 | 3-Cyano-N-(N,N-dimethylaminopropyl)-iminodibenzyl and salts thereof |
| NO77773473A NO145135C (no) | 1976-10-12 | 1977-10-11 | Analogifremgangsmaate ved fremstilling av den terapeutisk aktive forbindelse 3-cyan-n-(n,n-diemtylaminopropyl)-iminodibenzyl |
| AT726177A AT362378B (de) | 1976-10-12 | 1977-10-11 | Verfahren zur herstellung des neuen 3-cyan-n- -(n,n-dimethylaminopropyl)-iminodibenzyls und dessen saeureadditionssalzen |
| GR54557A GR66109B ( ) | 1976-10-12 | 1977-10-11 | |
| AR269561A AR216106A1 (es) | 1976-10-12 | 1977-10-12 | Procedimiento para la preparacion de 3-ciano-n-(n,n-dimetilaminopropil)-iminodibencilo |
| JP12157377A JPS5346991A (en) | 1976-10-12 | 1977-10-12 | Tricyclic compound |
| AT463180A AT363484B (de) | 1976-10-12 | 1980-09-16 | Verfahren zur herstellung des neuen 3-cyan-n(n,n-dimethylaminopropyl)-iminodibenzyls und dessen saeureadditionssalzen |
| AT463280A AT363485B (de) | 1976-10-12 | 1980-09-16 | Verfahren zur herstellung des neuen 3-cyan-n-(n,n-dimethylaminopropyl)-iminodibenzyls und dessen saeureadditionssalzen |
| AT463380A AT375345B (de) | 1976-10-12 | 1980-09-16 | Verfahren zur herstellung des neuen 3-cyan-n-(n,n-dimethylaminopropyl)-iminodibenzy s und dessen saeureadditionssalzen |
| CH847080A CH627169A5 ( ) | 1976-10-12 | 1980-11-14 | |
| CH846880A CH625226A5 ( ) | 1976-10-12 | 1980-11-14 | |
| CH846980A CH625227A5 ( ) | 1976-10-12 | 1980-11-14 | |
| SG609/83A SG60983G (en) | 1976-10-12 | 1983-09-28 | Tricyclic compounds |
| HK263/84A HK26384A (en) | 1976-10-12 | 1984-03-22 | Tricyclic compounds |
| MY97/85A MY8500097A (en) | 1976-10-12 | 1985-12-30 | Tricyclic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1287676A CH623574A5 ( ) | 1976-10-12 | 1976-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623574A5 true CH623574A5 ( ) | 1981-06-15 |
Family
ID=4387222
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1287676A CH623574A5 ( ) | 1976-10-12 | 1976-10-12 | |
| CH847080A CH627169A5 ( ) | 1976-10-12 | 1980-11-14 | |
| CH846980A CH625227A5 ( ) | 1976-10-12 | 1980-11-14 | |
| CH846880A CH625226A5 ( ) | 1976-10-12 | 1980-11-14 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH847080A CH627169A5 ( ) | 1976-10-12 | 1980-11-14 | |
| CH846980A CH625227A5 ( ) | 1976-10-12 | 1980-11-14 | |
| CH846880A CH625226A5 ( ) | 1976-10-12 | 1980-11-14 |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4138482A ( ) |
| JP (1) | JPS5346991A ( ) |
| AR (1) | AR216106A1 ( ) |
| AT (1) | AT362378B ( ) |
| AU (1) | AU512561B2 ( ) |
| BE (1) | BE859569A ( ) |
| CA (1) | CA1075688A ( ) |
| CH (4) | CH623574A5 ( ) |
| DE (1) | DE2745280C2 ( ) |
| DK (1) | DK153786C ( ) |
| ES (1) | ES463133A1 ( ) |
| FI (1) | FI62531C ( ) |
| FR (1) | FR2367749A1 ( ) |
| GB (1) | GB1583590A ( ) |
| GR (1) | GR66109B ( ) |
| HK (1) | HK26384A ( ) |
| HU (1) | HU173607B ( ) |
| IE (1) | IE45709B1 ( ) |
| IL (1) | IL53074A ( ) |
| IT (1) | IT1143697B ( ) |
| LU (1) | LU78280A1 ( ) |
| MC (1) | MC1169A1 ( ) |
| MY (1) | MY8500097A ( ) |
| NL (1) | NL183943C ( ) |
| NO (1) | NO145135C ( ) |
| NZ (1) | NZ185378A ( ) |
| PH (1) | PH13371A ( ) |
| PT (1) | PT67142B ( ) |
| SE (1) | SE427557B ( ) |
| SG (1) | SG60983G ( ) |
| YU (1) | YU40482B ( ) |
| ZA (1) | ZA775974B ( ) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4505909A (en) * | 1980-09-17 | 1985-03-19 | Bernstein Joel E | Method and composition for treating and preventing irritation of the eyes |
| US4370324A (en) * | 1980-09-17 | 1983-01-25 | Bernstein Joel E | Method and composition for treating and preventing irritation of the eyes |
| JPH03129724U ( ) * | 1990-04-09 | 1991-12-26 | ||
| US10639313B2 (en) | 2017-09-01 | 2020-05-05 | Ndsu Research Foundation | Compound for inhibition of delta-5-desaturase (D5D) and treatment of cancer and inflammation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK34863C (da) * | 1924-09-12 | 1925-08-17 | Carl Christian Marius Nielsen | Anordning ved Bagagebærere til Cykler, Motorcykler og lignende. |
| DK93077C (da) * | 1958-12-06 | 1962-03-26 | Geigy Ag J R | Fremgangsmåde til fremstilling af 5H-dibenzo[b,f]azepinforbindelser eller 10,11-dihydroforbindelser heraf eller salte heraf. |
| CH375360A (de) * | 1959-01-12 | 1964-02-29 | Geigy Ag J R | Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen |
| FR1359676A (fr) * | 1963-01-14 | 1964-04-30 | Rhone Poulenc Sa | Nouveau procédé d'aminoalcoylation d'amines hétérocycliques |
| FR84219E (fr) | 1963-01-14 | 1964-12-24 | Rhone Poulenc Sa | Nouveau procédé d'aminoalcoylation d'amines hétérocycliques |
-
1976
- 1976-10-12 CH CH1287676A patent/CH623574A5/de not_active IP Right Cessation
-
1977
- 1977-09-09 FI FI772675A patent/FI62531C/fi not_active IP Right Cessation
- 1977-09-16 NL NLAANVRAGE7710194,A patent/NL183943C/xx not_active IP Right Cessation
- 1977-09-19 YU YU2209/77A patent/YU40482B/xx unknown
- 1977-09-30 IT IT7728172A patent/IT1143697B/it active
- 1977-10-04 CA CA288,106A patent/CA1075688A/en not_active Expired
- 1977-10-05 AU AU29391/77A patent/AU512561B2/en not_active Expired
- 1977-10-05 ZA ZA00775974A patent/ZA775974B/xx unknown
- 1977-10-06 IL IL7753074A patent/IL53074A/xx unknown
- 1977-10-07 IE IE2051/77A patent/IE45709B1/en unknown
- 1977-10-07 DE DE2745280A patent/DE2745280C2/de not_active Expired
- 1977-10-07 PH PH20315A patent/PH13371A/en unknown
- 1977-10-07 NZ NZ185378A patent/NZ185378A/xx unknown
- 1977-10-10 LU LU7778280A patent/LU78280A1/xx unknown
- 1977-10-10 FR FR7730429A patent/FR2367749A1/fr active Granted
- 1977-10-10 MC MC771263A patent/MC1169A1/xx unknown
- 1977-10-10 HU HU77HO2017A patent/HU173607B/hu not_active IP Right Cessation
- 1977-10-11 AT AT726177A patent/AT362378B/de active
- 1977-10-11 US US05/840,790 patent/US4138482A/en not_active Expired - Lifetime
- 1977-10-11 SE SE7711433A patent/SE427557B/xx not_active IP Right Cessation
- 1977-10-11 BE BE181609A patent/BE859569A/xx not_active IP Right Cessation
- 1977-10-11 DK DK451477A patent/DK153786C/da active
- 1977-10-11 GR GR54557A patent/GR66109B/el unknown
- 1977-10-11 PT PT67142A patent/PT67142B/pt unknown
- 1977-10-11 ES ES77463133A patent/ES463133A1/es not_active Expired
- 1977-10-11 NO NO77773473A patent/NO145135C/no unknown
- 1977-10-11 GB GB42276/77A patent/GB1583590A/en not_active Expired
- 1977-10-12 JP JP12157377A patent/JPS5346991A/ja active Granted
- 1977-10-12 AR AR269561A patent/AR216106A1/es active
-
1980
- 1980-11-14 CH CH847080A patent/CH627169A5/de not_active IP Right Cessation
- 1980-11-14 CH CH846980A patent/CH625227A5/de not_active IP Right Cessation
- 1980-11-14 CH CH846880A patent/CH625226A5/de not_active IP Right Cessation
-
1983
- 1983-09-28 SG SG609/83A patent/SG60983G/en unknown
-
1984
- 1984-03-22 HK HK263/84A patent/HK26384A/xx unknown
-
1985
- 1985-12-30 MY MY97/85A patent/MY8500097A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2624789C3 ( ) | ||
| CH626615A5 ( ) | ||
| CH623574A5 ( ) | ||
| DE2514673C2 (de) | Benzo[b]bicyclo[3.3.1]nona-3,6a(10a)diene, Verfahren zu ihrer Herstellung und diese enthaltende anorektische Mittel | |
| CH653996A5 (de) | Tryptaminderivate und verfahren zu deren herstellung. | |
| CH638783A5 (de) | Verfahren zur herstellung neuer phenylazacycloalkane. | |
| DE2030675A1 (en) | 3-amino-4-phenyl-isoquinoline derivs | |
| AT363485B (de) | Verfahren zur herstellung des neuen 3-cyan-n-(n,n-dimethylaminopropyl)-iminodibenzyls und dessen saeureadditionssalzen | |
| AT217465B (de) | Verfahren zur Herstellung neuer Ester der Indol-Reihe | |
| CH615182A5 ( ) | ||
| AT375345B (de) | Verfahren zur herstellung des neuen 3-cyan-n-(n,n-dimethylaminopropyl)-iminodibenzy s und dessen saeureadditionssalzen | |
| CH523884A (de) | Verfahren zur Herstellung neuer Indol-Derivate | |
| AT227691B (de) | Verfahren zur Herstellung neuer Ester der Indol-Reihe | |
| AT263790B (de) | Verfahren zur Herstellung von neuen 2,3,4,5-Tetrahydro-1,4-benzoxazepinen, von deren Salzen und optisch isomeren Formen | |
| AT259553B (de) | Verfahren zur Herstellung von Indolderivaten | |
| DE2623257A1 (de) | Verfahren zur herstellung von n-alkenyl-2-aminomethyl-pyrrolidinen | |
| AT365200B (de) | Verfahren zur herstellung von neuen thienothiazin-derivaten und von deren salzen | |
| DE2237361A1 (de) | (5-indolyloxy)-essigsaeure-derivate und verfahren zur herstellung derselben | |
| AT337682B (de) | Verfahren zur herstellung von neuen benzocycloalkencarbonsauren sowie ihren estern und salzen | |
| DE1900948C (de) | Cis- und trans-2-Methyl-5-(3, 4, S-trimethoxybenzamidoJ-decahydroisochinolin | |
| AT218521B (de) | Verfahren zur Herstellung von neuen Derivaten des Piperidins und Tetrahydropyridins | |
| DE1038047B (de) | Verfahren zur Herstellung von N-aminoalkylierten Iminodibenzylen und deren Salzen | |
| DE1568253C (de) | N substituierte 1,2 Diphenyl 2 acyloxy 3 amino methyl butene | |
| DE3529159A1 (de) | Neues verfahren zur herstellung eines aminolactons | |
| AT360018B (de) | Verfahren zur herstellung des neuen 4-(7-brom-5 -methoxy-2-benzofuranyl)- piperidins und seiner saeureadditionssalze |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: F. HOFFMANN-LA ROCHE AG |
|
| PL | Patent ceased | ||
| PL | Patent ceased |