CH536271A - CNS active ethano:anthracene derivs. - prepd. by reacting corresp. parent anthracene with e.g. alkyl halide in presence of a base - Google Patents
CNS active ethano:anthracene derivs. - prepd. by reacting corresp. parent anthracene with e.g. alkyl halide in presence of a baseInfo
- Publication number
- CH536271A CH536271A CH1621667A CH1621667A CH536271A CH 536271 A CH536271 A CH 536271A CH 1621667 A CH1621667 A CH 1621667A CH 1621667 A CH1621667 A CH 1621667A CH 536271 A CH536271 A CH 536271A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- anthracene
- acid
- salts
- ethano
- Prior art date
Links
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001350 alkyl halides Chemical class 0.000 title 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- OUBZJILYWZSWOB-UHFFFAOYSA-N chembl46979 Chemical compound C12=CC=CC=C2C2(CN)C3=CC=CC=C3C1CC2 OUBZJILYWZSWOB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- BPZMYSHIRKBEKU-UHFFFAOYSA-N 9,10-ethanoanthracene-9(10h)-carbaldehyde Chemical compound C12=CC=CC=C2C2(C=O)C3=CC=CC=C3C1CC2 BPZMYSHIRKBEKU-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- -1 dimethylamino- Chemical class 0.000 abstract description 28
- 239000003814 drug Substances 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 2
- 230000011514 reflex Effects 0.000 abstract description 2
- KGMDODIDEQTIRA-UHFFFAOYSA-N 1,2-dihydrocyclobuta[a]anthracene Chemical class C1=CC2=CC3=CC=CC=C3C=C2C2=C1CC2 KGMDODIDEQTIRA-UHFFFAOYSA-N 0.000 abstract 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 125000003277 amino group Chemical group 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- RHCSKNNOAZULRK-UHFFFAOYSA-N mescaline Chemical compound COC1=CC(CCN)=CC(OC)=C1OC RHCSKNNOAZULRK-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- BZCOSCNPHJNQBP-UPHRSURJSA-N (z)-2,3-dihydroxybut-2-enedioic acid Chemical compound OC(=O)C(\O)=C(\O)C(O)=O BZCOSCNPHJNQBP-UPHRSURJSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- OEMAILVIMCRZDK-UHFFFAOYSA-N ClC12C=3C=CC=CC3C(C3=CC=CC=C13)(CC2)CNCC Chemical compound ClC12C=3C=CC=CC3C(C3=CC=CC=C13)(CC2)CNCC OEMAILVIMCRZDK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 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
- 230000005540 biological transmission Effects 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 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
- 230000001914 calming effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000001558 histaminolytic effect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 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
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 229940107700 pyruvic acid Drugs 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
- 150000003254 radicals Chemical group 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Ethanoanthracene derivatives of general formula (I) and their salts. A = dimethylamino-, diethylamino-one Cl- in 2- or 3-position preferably 2-chloro-9-diethylaminomethyl 9,10-dihydro-9,10-ethano-(1,2) anthracene. Drugs for treatment of central nervous system, e.g. anti-psychomotive and control of spinal reflex; also antihistamine and tranquiliser.
Description
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Verbindungen der Formel
EMI1.1
worin A eine sekundäre oder tertiäre Aminogruppe ist, und die in höherer Stellung als der 2-Stellung ein Halogenatom tragen oder ihrer Salze.
Als Substituenten der sekundären oder tertiären Aminogruppe kommen vor allem niedere Kohlenwasserstoffreste in Frage, die auch durch Heteroatome, wie Sauerstoff, Schwefel oder Stickstoff, unterbrochen und/oder durch freie Hydroxy-, Amino- oder Mercaptogruppen oder Halogenatome, wie Fluor, Chlor, Brom oder Jod, substituiert sein können.
Als niedere Kohlenwasserstoffreste sind vor allem zu nennen: niedere Alkyl- oder Alkenylreste, wie Methyl-, Äthyl-, Propyl-, Isopropylreste, gerade oder verzweigte, in beliebiger Stelle verbundene Butyl-, Pentyl- oder Hexylreste, Allyl- oder Methallylreste, unsubstituierte oder alkylsubstituierte Cycloalkyl- oder Cycloalkenylreste, wie Cyclopentyl-, Cyclohexyl-, Cycloheptyl-, Cyclopentenyl-, Cyclohexenylreste, unsubstituierte oder alkylsubstituierte Cycloalkyl- oder -alkenyI-alkylreste, wie Cyclopentyl- oder Cyclohexenylmethyl-, -äthyl- oder -propylreste, Aralkyl- oder Aralkenyl-, wie Phenylmethyl-, -äthyl-, -vinyl- oder -propylreste, oder Aryl-, insbesondere Phenylreste oder Alkylen- oder Alkenylenreste, wie z. B. Butylen-(1,4), Pentylen-(1,5), 1,5-Dimethylpentylen-(1,5), Hexylen-(1,6), Hexylen-(1,5). Durch Heteroatome unterbrochene Reste dieser Art sind z. B.
Alkoxyalkyl- oder Oxa-cycloalkylalkylreste, wie Methoxyäthyl, Äthoxyäthyl, Propoxyäthyl, Butoxyäthyl, Methoxypropyl, Methoxyäthoxyäthyl, Tetrahydrofurylmethyl, Methylmercaptoäthyl, Oxa-, Aza- oder Thiaalkylen- oder -alkenylenreste, wie 3-Aza-, Oxa- oder Thiapentylen-(1,5), 3-Aza hexylen-(1,6), 1,5-Dimethyl-3-aza-pentylen-(1,5), 3-Methyl 3-aza-pentylen-(l ,5) oder 3-Hydroxyäthyl-3-aza-pentylen (1,5).
Die Aminogruppe ist vor allem eine Mono- oder Diniederalkyl-aminogruppe, wie die Methylamino-, Äthylamino-, n-Butylamino-, Dimethylamino-, Diäthylamino-, Dipropylamino-, N-Methyl-N-äthylaminogruppe, eine N-Niederalkyl-N-cycloalkylaminogruppe, wie die N-Methyl-Ncyclopentyl- oder -cyclohexylgruppe, eine Pyrrolidino-, Piperidino-, Morpholino- oder Thio-morpholinogruppe, wie die Pyrrolidino-, Piperidino-, Morpholino-, Piperazino-, N-Methyl-, N-Äthyl- oder N-ss-Hydroxyäthylpiperazinogruppe.
Die neuen Verbindungen besitzen wertvolle pharmakologische Eigenschaften. So zeigen sie eine zentralhemmende Wirkung, die durch einen Antagonismus gegenüber psychomotorischen Stoffen, wie z. B. Mescalin, sowie durch eine Hemmung der spinalen Reflexübertragung gekennzeichnet ist, sowie eine histaminolytische Wirkung und können daher als psychotrope, beruhigende Medikamente in der Humanund Veterinärmedizin Verwendung finden. Sie eignen sich aber auch als Zusätze zu Tierfutter, da sie eine bessere Nahrungsverwertung bewirken. Weiter können die neuen Verbindungen als Ausgangs- oder Zwischenprodukte für die Herstellung anderer wertvoller Verbindungen dienen.
Besonders wertvoll sind die Verbindungen der Formel I, worin die Aminogruppe eine Mono- oder Di-niederalkyloder cycloalkyl-amino-, Pyrrolidino-, Piperidino-, Morpholino-, Piperazino-, N-Methylpiperazino-, N-Äthylpiperazinooder N-ss-Hydroxyäthyl-piperazinogruppe darstellt, und vor allem die Methylamino-, Äthylamino-, n-Butylamino-, Dimethylamino- oder Diäthylaminogruppe bedeutet.
Vor allem hervorzuheben sind die Verbindungen der Formel I, die in 10-Stellung ein Chloratom aufweisen, und worin A die Mono- oder Dimethyl- oder -äthylaminogruppe darstellt, und ihre Salze.
Das erfindungsgemässe Verfahren zur Herstellung der neuen Verbindungen ist dadurch gekennzeichnet, dass man in einer Verbindung der Formel die in höherer Stellung als der 2-Stellung ein Halogenatom trägt und worin X einen der oben definierten Gruppe der Formel -CH2-A entsprechender Rest ist, der eine sich vom Stickstoffatom an ein benachbartes Kohlenstoffatom erstrekkende Doppelbindung aufweist, die CN-Doppelbindung reduziert.
Die Reduktion der Azomethin-Doppelbindung kann in üblicher Weise erfolgen, zum Beispiel mit Metallhydriden, z. B. Di-leichtmetallhydriden, wie Alkaliborhydriden, oder von katalytisch aktiviertem Wasserstoff, wobei als Katalysatoren vor allem Platinoxyd oder Raney-Nickel zu erwähnen sind, oder gegebenenfalls mit Ameisensäure.
In erhaltene sekundäre Aminogruppen lassen sich nach den Methoden der Alkylierung in üblicher Weise noch weitere Stickstoffsubstituenten einführen, z. B. durch Behandlung mit reaktionsfähigen Estern, z. B. den oben genannten, der entsprechenden Alkohole.
Die Ausgangstoffe können auch in Form eines unter den Reaktionsbedingungen gebildeten Reaktionsgemisches eingesetzt werden. So kann man z. B. von den 9-Formylverbindungen ausgehen und sie unter geeigneten, z. B. den oben für die Reduktion erwähnten reduzierenden Bedingungen mit primären oder sekundären Aminen behandeln, oder von einem entsprechenden 9-(Amino-methyl)-9, 10-dihydro- 9,10-äthanoanthracen ausgehen, dessen Aminogruppe primär oder sekundär ist und sie unter geeigneten, z. B. den oben für die Reduktion erwähnten reduzierenden Bedingungen mit einem entsprechenden Aldehyd oder Keton behandeln, wobei als Zwischenprodukte die Verbindungen der Formel II entstehen.
Die genannten Reaktionen können in üblicher Weise durchgeführt werden.
Die Ausgangsstoffe sind bekannt oder können nach an sich bekannten Verfahren gewonnen werden.
Die neuen Verbindungen werden je nach den Reaktionsbedingungen und Ausgangsstoffen in freier Form oder in Form ihrer Salze erhalten. Die Salze der neuen Verbindungen können in an sich bekannter Weise in die freien Verbindungen übergeführt werden, z. B. Säureadditionssalze durch Reaktion mit einem basischen Mittel. Anderseits können gegebenenfalls erhaltene freie Basen mit anorganischen oder organischen Säuren Salze bilden. Zur Herstellung von Säureadditionssalzen werden insbesondere therapeutisch verwendbare Säuren verwendet, z. B.
Halogenwasserstoffsäuren, beispielsweise Salzsäure oder Bromwasserstoffsäure, Perchlorsäure, Salpetersäure oder Thiocyansäure, Schwefel- oder Phosphorsäuren, oder organische Säuren, wie Ameisensäure, Essigsäure, Propionsäure, Glykolsäure, Milchsäure, Brenztraubensäure, Oxalsäure, Malonsäure, Bernsteinsäure, Maleinsäure, Fumarsäure, Äpfelsäure, Weinsäure, Zitronensäure,
EMI1.2
Ascorbinsäure, Hydroxymaleinsäure, Dihydroxymaleinsäure, Benzoesäure, Phenylessigsäure, 4-Amino-benzoesäure, 4-Hydroxybenzoesäure, Anthranilsäure, Zimtsäure, Mandelsäure, Salicylsäure, 4-Amino-salicylsäure, 2-Phenoxy-benzoesäure, 2-Acetoxybenzoesäure, Methansulfonsäure, Äthansulfonsäure, Hydroxyäthansulfonsäure, Benzolsulfonsäure, p-Toluol-sulfonsäure, Naphthalin-sulfonsäure oder Sulfanilsäure, oder Methionin, Tryptophan, Lysin oder Arginin. Dabei können Mono- oder Polysalze vorliegen.
Die neuen Verbindungen können als Heilmittel in Form von pharmazeutischen Präparaten verwendet werden, welche diese Verbindungen zusammen mit pharmazeutischen, organischen oder anorganischen, festen oder flüssigen Trägerstoffen, die für enterale, z. B. orale, oder parenterale Gabe geeignet sind, enthalten.
Die neuen Verbindungen können auch in der Tiermedi zin, z. B. in einer der oben genannten Formen, oder bei der Aufzucht und Ernährung von Tieren in Form von Futtermitteln oder von Zusatzmitteln für Tierfutter verwendet werden.
In den folgenden Beispielen sind die Temperaturen in
Celsiusgraden angegeben.
Beispiel 1
36 g 10-Chlor-9, 10-dihydro-9,1 0-äthano-(1 ,2)-9-anthra- cenaldehyd werden mit einer gesättigten Lösung von Äthylamin in Äthanol während 5 Stunden im Autoklav auf 80" erhitzt. Anschliessend dampft man die Lösung im Vakuum ein.
Den Rückstand löst man in 250 ml Äthanol und hydriert bei Zimmertemperatur nach Zugabe von 5 g Raney-Nickel.
Nach dem Abfiltrieren des Katalysators und dem Eindampfen des Lösungsmittels verbleibt das 9-Äthylaminomethyl-10- chlor-9,10-dihydro-9,10-äthano-anthracen der Formel
EMI2.1
das nach Umkristallisation aus Hexan bei 88-91 schmilzt (Ausbeute 64%)¯Das Hydrochlorid schmilzt oberhalb 300 .
Beispiel 2
In analoger Weise wie in Beispiel 1 beschrieben, kann man durch Umsetzen von 10-Chlor-9, 10-dihydro-9, 10- äthano-(1,2)-9-anthracenaldehyd mit Diäthylamin und katalytischer Reduktion der CN-Doppelbindung das 9-Diäthyl aminomethyl-10-chlor-9, 10-dihydro-9 ,10-äthano-( 1,2)- anthracen der Formel
EMI2.2
erhalten, das nach Umkristallisation aus Äthanol bei 116 bis 118 schmilzt. Das Hydrochlorid schmilzt bei 200-205".
The invention relates to a process for the preparation of compounds of the formula
EMI1.1
wherein A is a secondary or tertiary amino group, and those in a position higher than the 2-position carry a halogen atom or their salts.
Substituents of the secondary or tertiary amino group that are particularly suitable are lower hydrocarbon radicals, which are also interrupted by heteroatoms, such as oxygen, sulfur or nitrogen, and / or by free hydroxyl, amino or mercapto groups or halogen atoms, such as fluorine, chlorine, bromine or Iodine, can be substituted.
Lower hydrocarbon radicals that should be mentioned in particular are: lower alkyl or alkenyl radicals, such as methyl, ethyl, propyl, isopropyl radicals, straight or branched butyl, pentyl or hexyl radicals connected at any point, allyl or methallyl radicals, unsubstituted or alkyl-substituted cycloalkyl or cycloalkenyl radicals, such as cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl radicals, unsubstituted or alkyl-substituted cycloalkyl or -alkenyI-alkyl radicals, such as cyclopentyl or cyclohexenylmethyl, or arylalkyl radicals, or aryl, aralkyl - Such as phenylmethyl, ethyl, vinyl or propyl, or aryl, especially phenyl or alkylene or alkenylene, such as. B. butylene- (1,4), pentylene- (1.5), 1,5-dimethylpentylene- (1.5), hexylene- (1.6), hexylene- (1.5). Residues of this type interrupted by heteroatoms are e.g. B.
Alkoxyalkyl or oxa-cycloalkylalkyl radicals, such as methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl, methoxyethoxyethyl, tetrahydrofurylmethyl, methylmercaptoethyl, oxa-, aza or thiaalkylene or -alkenylene radicals, such as 3-aza, oxyethylene or thiapentylene (1, 5), 3-aza hexylene- (1,6), 1,5-dimethyl-3-aza-pentylene- (1,5), 3-methyl-3-aza-pentylene- (1,5) or 3-hydroxyethyl -3-aza-pentylene (1.5).
The amino group is above all a mono- or di-lower alkyl amino group, such as the methylamino, ethylamino, n-butylamino, dimethylamino, diethylamino, dipropylamino, N-methyl-N-ethylamino group, an N-lower alkyl-N- cycloalkylamino group, such as the N-methyl-Ncyclopentyl or -cyclohexyl group, a pyrrolidino, piperidino, morpholino or thio-morpholino group, such as the pyrrolidino, piperidino, morpholino, piperazino, N-methyl, N-ethyl - or N-ß-hydroxyethylpiperazino group.
The new compounds have valuable pharmacological properties. So they show a central inhibiting effect, which by an antagonism to psychomotor substances, such as. B. mescaline, and is characterized by an inhibition of the spinal reflex transmission, as well as a histaminolytic effect and can therefore be used as psychotropic, calming drugs in human and veterinary medicine. But they are also suitable as additives to animal feed, as they bring about better food utilization. The new compounds can also serve as starting materials or intermediates for the production of other valuable compounds.
The compounds of formula I in which the amino group is a mono- or di-lower alkyl or cycloalkyl-amino, pyrrolidino, piperidino, morpholino, piperazino, N-methylpiperazino, N-ethylpiperazino or N-ß-hydroxyethyl represents piperazino, and in particular the methylamino, ethylamino, n-butylamino, dimethylamino or diethylamino group.
Particularly noteworthy are the compounds of the formula I which have a chlorine atom in the 10-position and in which A represents the mono- or dimethyl or -ethylamino group, and their salts.
The process according to the invention for the preparation of the new compounds is characterized in that in a compound of the formula which carries a halogen atom in a position higher than the 2-position and in which X is a radical corresponding to the group of the formula -CH2-A defined above, which has a double bond extending from the nitrogen atom to an adjacent carbon atom which reduces the CN double bond.
The azomethine double bond can be reduced in a conventional manner, for example with metal hydrides, e.g. B. Di-light metal hydrides, such as alkali borohydrides, or of catalytically activated hydrogen, especially platinum oxide or Raney nickel are to be mentioned as catalysts, or optionally with formic acid.
In the secondary amino groups obtained, further nitrogen substituents can be introduced in the usual manner by the alkylation methods, eg. B. by treatment with reactive esters, e.g. B. the above, the corresponding alcohols.
The starting materials can also be used in the form of a reaction mixture formed under the reaction conditions. So you can z. B. start from the 9-formyl compounds and use them under suitable, z. B. treat the reducing conditions mentioned above for the reduction with primary or secondary amines, or start from a corresponding 9- (amino-methyl) -9, 10-dihydro-9,10-ethanoanthracene whose amino group is primary or secondary and they under suitable, e.g. B. treat the reducing conditions mentioned above for the reduction with an appropriate aldehyde or ketone, the compounds of formula II being formed as intermediates.
The reactions mentioned can be carried out in a customary manner.
The starting materials are known or can be obtained by processes known per se.
The new compounds are obtained in free form or in the form of their salts, depending on the reaction conditions and starting materials. The salts of the new compounds can be converted into the free compounds in a manner known per se, eg. B. Acid addition salts by reaction with a basic agent. On the other hand, any free bases obtained can form salts with inorganic or organic acids. For the preparation of acid addition salts, therapeutically useful acids are used in particular, e.g. B.
Hydrogen halide acids, for example hydrochloric acid or hydrobromic acid, perchloric acid, nitric acid or thiocyanic acid, sulfuric or phosphoric acids, or organic acids such as formic acid, acetic acid, propionic acid, glycolic acid, lactic acid, pyruvic acid, oxalic acid, malonic acid, succinic acid, maleic acid, felic acid, citric acid ,
EMI1.2
Ascorbic acid, hydroxymaleic acid, dihydroxymaleic acid, benzoic acid, phenylacetic acid, 4-amino-benzoic acid, 4-hydroxybenzoic acid, anthranilic acid, cinnamic acid, mandelic acid, salicylic acid, 4-amino-salicylic acid, 2-phenoxy-benzoic acid, ethanesulfanoic acid, methanesulfanoic acid, methanesulfanoic acid, 2-acetoxybenzoic acid Benzene sulfonic acid, p-toluene sulfonic acid, naphthalene sulfonic acid or sulfanilic acid, or methionine, tryptophan, lysine or arginine. Mono- or poly-salts can be present here.
The new compounds can be used as medicaments in the form of pharmaceutical preparations, which these compounds together with pharmaceutical, organic or inorganic, solid or liquid carriers which are suitable for enteral, e.g. B. oral or parenteral administration are suitable.
The new compounds can also be used in animal medicine, e.g. B. in one of the forms mentioned above, or in the rearing and feeding of animals in the form of feed or additives for animal feed.
In the following examples the temperatures are in
Degrees Celsius.
example 1
36 g of 10-chloro-9, 10-dihydro-9,1 0-ethano- (1, 2) -9-anthracenaldehyde are heated in an autoclave to 80 "with a saturated solution of ethylamine in ethanol for 5 hours. Then the solution is evaporated in vacuo.
The residue is dissolved in 250 ml of ethanol and hydrogenated at room temperature after adding 5 g of Raney nickel.
After the catalyst has been filtered off and the solvent has been evaporated off, the 9-ethylaminomethyl-10-chloro-9,10-dihydro-9,10-ethano-anthracene of the formula remains
EMI2.1
which after recrystallization from hexane melts at 88-91 (yield 64%) ¯The hydrochloride melts above 300.
Example 2
In an analogous manner to that described in Example 1, the 9th can be obtained by reacting 10-chloro-9, 10-dihydro-9, 10-ethano- (1,2) -9-anthracenaldehyde with diethylamine and catalytic reduction of the CN double bond -Diethyl aminomethyl-10-chloro-9, 10-dihydro-9, 10-ethano- (1,2) - anthracene of the formula
EMI2.2
obtained, which melts at 116 to 118 after recrystallization from ethanol. The hydrochloride melts at 200-205 ".
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1621667A CH536271A (en) | 1960-11-29 | 1965-12-10 | CNS active ethano:anthracene derivs. - prepd. by reacting corresp. parent anthracene with e.g. alkyl halide in presence of a base |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH483965A CH398569A (en) | 1960-11-29 | 1960-11-29 | Process for the preparation of new 9-aminoalkyl-9,10-dihydro-9,10-ethano- (1,2) -anthracenes |
| CH1708665A CH448069A (en) | 1960-11-29 | 1965-12-10 | Process for the production of new amines |
| CH1621667A CH536271A (en) | 1960-11-29 | 1965-12-10 | CNS active ethano:anthracene derivs. - prepd. by reacting corresp. parent anthracene with e.g. alkyl halide in presence of a base |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH536271A true CH536271A (en) | 1973-04-30 |
Family
ID=27175008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1621667A CH536271A (en) | 1960-11-29 | 1965-12-10 | CNS active ethano:anthracene derivs. - prepd. by reacting corresp. parent anthracene with e.g. alkyl halide in presence of a base |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH536271A (en) |
-
1965
- 1965-12-10 CH CH1621667A patent/CH536271A/en unknown
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| PLZ | Patent of addition ceased |