CH533079A - Verfahren zur Herstellung von neuen N-substituierten 9-(Aminoalkyl)-12-acyloxy-9,10-dihydro-9,10-äthanoanthrazenen - Google Patents
Verfahren zur Herstellung von neuen N-substituierten 9-(Aminoalkyl)-12-acyloxy-9,10-dihydro-9,10-äthanoanthrazenenInfo
- Publication number
- CH533079A CH533079A CH149472A CH149472A CH533079A CH 533079 A CH533079 A CH 533079A CH 149472 A CH149472 A CH 149472A CH 149472 A CH149472 A CH 149472A CH 533079 A CH533079 A CH 533079A
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- dihydro
- compounds
- dependent
- salts
- Prior art date
Links
- 230000000506 psychotropic effect Effects 0.000 title abstract description 3
- -1 piperazino Chemical group 0.000 claims abstract description 57
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 11
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical class OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 230000001419 dependent effect Effects 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- PWLWKEXZQXVQHM-UHFFFAOYSA-N [1-[(dimethylamino)methyl]-15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl] acetate Chemical compound CN(C)CC12C3=CC=CC=C3C(C=3C=CC=CC13)CC2OC(C)=O PWLWKEXZQXVQHM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 238000006352 cycloaddition reaction Methods 0.000 claims description 3
- BVWSPWXNBUJOOL-UHFFFAOYSA-N 1-[(cyclopropylamino)methyl]tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-ol Chemical compound C1(CC1)NCC12C3=CC=CC=C3C(C=3C=CC=CC13)CC2O BVWSPWXNBUJOOL-UHFFFAOYSA-N 0.000 claims description 2
- NDDRMAPQLIRZCX-UHFFFAOYSA-N CN(C)CC(C(CC1C2=C3)O)(C2=CC=C3Cl)C2=C1C=CC(Cl)=C2 Chemical compound CN(C)CC(C(CC1C2=C3)O)(C2=CC=C3Cl)C2=C1C=CC(Cl)=C2 NDDRMAPQLIRZCX-UHFFFAOYSA-N 0.000 claims description 2
- GCFXSHSODNOEIU-UHFFFAOYSA-N CN(C)CC12C3=CC=CC=C3C(C=3C=CC=CC13)CC2(O)C Chemical compound CN(C)CC12C3=CC=CC=C3C(C=3C=CC=CC13)CC2(O)C GCFXSHSODNOEIU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 230000002829 reductive effect Effects 0.000 abstract description 2
- 238000005932 reductive alkylation reaction Methods 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- RHCSKNNOAZULRK-UHFFFAOYSA-N mescaline Chemical compound COC1=CC(CCN)=CC(OC)=C1OC RHCSKNNOAZULRK-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- 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
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
- GDSMGXRBQPHNLE-UHFFFAOYSA-N 1-(diethylaminomethyl)tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-ol Chemical compound C(C)N(CC)CC12C3=CC=CC=C3C(C=3C=CC=CC13)CC2O GDSMGXRBQPHNLE-UHFFFAOYSA-N 0.000 description 1
- OHKYCRAPAONNCH-UHFFFAOYSA-N 1-(ethylaminomethyl)tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-ol Chemical compound C(C)NCC12C3=CC=CC=C3C(C=3C=CC=CC13)CC2O OHKYCRAPAONNCH-UHFFFAOYSA-N 0.000 description 1
- FICKEBFJBLMGHG-UHFFFAOYSA-N 1-anthracen-9-yl-n,n-dimethylmethanamine Chemical compound C1=CC=C2C(CN(C)C)=C(C=CC=C3)C3=CC2=C1 FICKEBFJBLMGHG-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- LNSCNEJNLACZPA-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(2-methylphenyl)butanedioic acid Chemical compound CC1=CC=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=CC=C1C LNSCNEJNLACZPA-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-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
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 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
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- PODAMDNJNMAKAZ-UHFFFAOYSA-N penta-2,3-diene Chemical group CC=C=CC PODAMDNJNMAKAZ-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 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
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Fodder In General (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH149472A CH533079A (de) | 1969-03-25 | 1969-03-25 | Verfahren zur Herstellung von neuen N-substituierten 9-(Aminoalkyl)-12-acyloxy-9,10-dihydro-9,10-äthanoanthrazenen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH448069A CH539602A (de) | 1969-03-25 | 1969-03-25 | Verfahren zur Herstellung von neuen N-substituierten 9-(Aminoalkyl)-9,10-dihydro-9,10-äthano-anthrazenen |
| CH149472A CH533079A (de) | 1969-03-25 | 1969-03-25 | Verfahren zur Herstellung von neuen N-substituierten 9-(Aminoalkyl)-12-acyloxy-9,10-dihydro-9,10-äthanoanthrazenen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH533079A true CH533079A (de) | 1973-01-31 |
Family
ID=4276876
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149472A CH533079A (de) | 1969-03-25 | 1969-03-25 | Verfahren zur Herstellung von neuen N-substituierten 9-(Aminoalkyl)-12-acyloxy-9,10-dihydro-9,10-äthanoanthrazenen |
| CH448069A CH539602A (de) | 1968-05-16 | 1969-03-25 | Verfahren zur Herstellung von neuen N-substituierten 9-(Aminoalkyl)-9,10-dihydro-9,10-äthano-anthrazenen |
| CH149372A CH532553A (de) | 1969-03-25 | 1969-03-25 | Verfahren zur Herstellung von neuen N-substituierten 9-NAminoalkyl)-12-acyloxy-9,10-dihydro-9,10-äthano-anthrazenen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH448069A CH539602A (de) | 1968-05-16 | 1969-03-25 | Verfahren zur Herstellung von neuen N-substituierten 9-(Aminoalkyl)-9,10-dihydro-9,10-äthano-anthrazenen |
| CH149372A CH532553A (de) | 1969-03-25 | 1969-03-25 | Verfahren zur Herstellung von neuen N-substituierten 9-NAminoalkyl)-12-acyloxy-9,10-dihydro-9,10-äthano-anthrazenen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5017070B1 (enrdf_load_stackoverflow) |
| AT (3) | AT302285B (enrdf_load_stackoverflow) |
| CH (3) | CH533079A (enrdf_load_stackoverflow) |
| ES (3) | ES388318A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2100578B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1266890A (enrdf_load_stackoverflow) |
| SE (1) | SE370944B (enrdf_load_stackoverflow) |
| SU (2) | SU414792A3 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266570A (en) * | 1991-08-15 | 1993-11-30 | Imperial Chemical Industries Plc | Piperidine derivatives, compositions and use |
| US5399568A (en) * | 1991-08-15 | 1995-03-21 | Imperial Chemical Industries Plc | Methanoanthrancenyl piperidyl antipsychotics |
| US5512575A (en) * | 1991-08-15 | 1996-04-30 | Zeneca Limited | Methanoanthraceneyl methyl piperidinyl compounds |
-
1969
- 1969-03-25 CH CH149472A patent/CH533079A/de not_active IP Right Cessation
- 1969-03-25 CH CH448069A patent/CH539602A/de unknown
- 1969-03-25 CH CH149372A patent/CH532553A/de not_active IP Right Cessation
- 1969-04-30 GB GB1266890D patent/GB1266890A/en not_active Expired
- 1969-05-12 SE SE7204519A patent/SE370944B/xx unknown
- 1969-05-14 AT AT707570A patent/AT302285B/de not_active IP Right Cessation
- 1969-05-14 AT AT708070A patent/AT299224B/de not_active IP Right Cessation
- 1969-05-14 AT AT707970A patent/AT304490B/de not_active IP Right Cessation
- 1969-05-15 SU SU1493619A patent/SU414792A3/ru active
- 1969-05-15 SU SU1485632A patent/SU400078A3/ru active
-
1971
- 1971-02-16 ES ES388318A patent/ES388318A1/es not_active Expired
- 1971-02-16 ES ES388319A patent/ES388319A1/es not_active Expired
- 1971-02-16 ES ES388314A patent/ES388314A1/es not_active Expired
- 1971-05-12 JP JP46033217A patent/JPS5017070B1/ja active Pending
- 1971-06-08 FR FR7120748A patent/FR2100578B1/fr not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266570A (en) * | 1991-08-15 | 1993-11-30 | Imperial Chemical Industries Plc | Piperidine derivatives, compositions and use |
| US5399568A (en) * | 1991-08-15 | 1995-03-21 | Imperial Chemical Industries Plc | Methanoanthrancenyl piperidyl antipsychotics |
| US5455246A (en) * | 1991-08-15 | 1995-10-03 | Imperial Chemical Industries, Plc | Piperidine derivatives |
| US5512575A (en) * | 1991-08-15 | 1996-04-30 | Zeneca Limited | Methanoanthraceneyl methyl piperidinyl compounds |
| US5550136A (en) * | 1991-08-15 | 1996-08-27 | Zeneca Limited | Methanoanthrancenyl piperidyl antipsychotics |
| US5681840A (en) * | 1991-08-15 | 1997-10-28 | Zeneca Limited | Tricyclic antipsychotic compounds |
| US5719166A (en) * | 1991-08-15 | 1998-02-17 | Imperial Chemical Industries Plc | Therapeutic agents |
Also Published As
| Publication number | Publication date |
|---|---|
| AT299224B (de) | 1972-06-12 |
| CH532553A (de) | 1973-01-15 |
| CH539602A (de) | 1973-09-14 |
| FR2100578B1 (enrdf_load_stackoverflow) | 1974-08-23 |
| SU414792A3 (enrdf_load_stackoverflow) | 1974-02-05 |
| GB1266890A (enrdf_load_stackoverflow) | 1972-03-15 |
| SU400078A3 (enrdf_load_stackoverflow) | 1973-10-03 |
| AT302285B (de) | 1972-10-10 |
| FR2100578A1 (enrdf_load_stackoverflow) | 1972-03-24 |
| SE370944B (enrdf_load_stackoverflow) | 1974-11-04 |
| ES388318A1 (es) | 1973-05-01 |
| ES388314A1 (es) | 1973-05-01 |
| JPS5017070B1 (enrdf_load_stackoverflow) | 1975-06-18 |
| ES388319A1 (es) | 1973-05-01 |
| AT304490B (de) | 1973-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |