FI62062C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 3,-diklorfenon-0-(2-aminoetyl)-oximer - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 3,-diklorfenon-0-(2-aminoetyl)-oximer Download PDFInfo
- Publication number
- FI62062C FI62062C FI760694A FI760694A FI62062C FI 62062 C FI62062 C FI 62062C FI 760694 A FI760694 A FI 760694A FI 760694 A FI760694 A FI 760694A FI 62062 C FI62062 C FI 62062C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- defined above
- aminoethyl
- reacted
- Prior art date
Links
- -1 2-AMINOETHYL Chemical class 0.000 title description 25
- 230000001225 therapeutic effect Effects 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 27
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000002923 oximes Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- 125000003544 oxime group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- VAWHTWXBNQFBAJ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.NCCON VAWHTWXBNQFBAJ-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 230000001476 alcoholic effect Effects 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000001430 anti-depressive effect Effects 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 102000010909 Monoamine Oxidase Human genes 0.000 description 4
- 108010062431 Monoamine oxidase Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229960005333 tetrabenazine Drugs 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FOOWFHHXRQACQS-UHFFFAOYSA-N Cl.NCCON=C(CCCCCl)C1=CC=C(Cl)C(Cl)=C1 Chemical compound Cl.NCCON=C(CCCCCl)C1=CC=C(Cl)C(Cl)=C1 FOOWFHHXRQACQS-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 201000005917 gastric ulcer Diseases 0.000 description 2
- KDFBGNBTTMPNIG-UHFFFAOYSA-N hydron;2-(1h-indol-3-yl)ethanamine;chloride Chemical compound Cl.C1=CC=C2C(CCN)=CNC2=C1 KDFBGNBTTMPNIG-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 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
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- KEIYADKZZVLIEK-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-(2-methoxyethoxy)butan-1-one Chemical compound COCCOCCCC(=O)C1=CC=C(Cl)C(Cl)=C1 KEIYADKZZVLIEK-UHFFFAOYSA-N 0.000 description 1
- GFBAJYNLKFXOKJ-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-5-methoxypentan-1-one Chemical compound COCCCCC(=O)C1=CC=C(Cl)C(Cl)=C1 GFBAJYNLKFXOKJ-UHFFFAOYSA-N 0.000 description 1
- USBIQASYZGDCMD-UHFFFAOYSA-N 2-[[1-(3,4-dichlorophenyl)-4-ethoxybutylidene]amino]oxyethanamine;hydrochloride Chemical compound Cl.CCOCCCC(=NOCCN)C1=CC=C(Cl)C(Cl)=C1 USBIQASYZGDCMD-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- FVZFSQDGTYKUFP-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-5-oxopentanenitrile Chemical compound ClC1=CC=C(C(=O)CCCC#N)C=C1Cl FVZFSQDGTYKUFP-UHFFFAOYSA-N 0.000 description 1
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
- OEUKELWGUDCGAY-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-6-oxohexanenitrile Chemical compound ClC1=CC=C(C(=O)CCCCC#N)C=C1Cl OEUKELWGUDCGAY-UHFFFAOYSA-N 0.000 description 1
- JIXLYSYDPZKZMS-UHFFFAOYSA-N 7-(3,4-dichlorophenyl)-7-oxoheptanenitrile Chemical compound ClC1=CC=C(C(=O)CCCCCC#N)C=C1Cl JIXLYSYDPZKZMS-UHFFFAOYSA-N 0.000 description 1
- UATAZSHOVCUWFE-UHFFFAOYSA-N COCCOCCC(CC(=O)C1=CC=C(C=C1)Cl)Cl Chemical compound COCCOCCC(CC(=O)C1=CC=C(C=C1)Cl)Cl UATAZSHOVCUWFE-UHFFFAOYSA-N 0.000 description 1
- HSCWQBGEFBQXGN-UHFFFAOYSA-N COCCOCCCC(C(=NOCCN)C1=CC=CC=C1)Cl Chemical compound COCCOCCCC(C(=NOCCN)C1=CC=CC=C1)Cl HSCWQBGEFBQXGN-UHFFFAOYSA-N 0.000 description 1
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 description 1
- 206010015995 Eyelid ptosis Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000007623 Lordosis Diseases 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000002566 clonic effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940077481 dl- 5-hydroxytryptophan Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- BONQLQLSYDZXOB-UHFFFAOYSA-N ethene 1-phenylbutan-1-one Chemical group C=C.CCCC(=O)C1=CC=CC=C1 BONQLQLSYDZXOB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate 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
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- JBHIHRWEZRKIGE-UHFFFAOYSA-N n-[1-(3,4-dichlorophenyl)-6-methoxyhexylidene]hydroxylamine Chemical compound COCCCCCC(=NO)C1=CC=C(Cl)C(Cl)=C1 JBHIHRWEZRKIGE-UHFFFAOYSA-N 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 231100000189 neurotoxic Toxicity 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- FZDKEAZDPFKHPJ-UHFFFAOYSA-N o-(2-aminoethyl)hydroxylamine;hydrochloride Chemical compound Cl.NCCON FZDKEAZDPFKHPJ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 230000004202 respiratory function Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 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
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/58—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL7503311 | 1975-03-20 | ||
NL7503311A NL7503311A (nl) | 1975-03-20 | 1975-03-20 | Verbindingen met antidepressieve werking. |
Publications (3)
Publication Number | Publication Date |
---|---|
FI760694A7 FI760694A7 (en, 2012) | 1976-09-21 |
FI62062B FI62062B (fi) | 1982-07-30 |
FI62062C true FI62062C (fi) | 1982-11-10 |
Family
ID=19823425
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI760694A FI62062C (fi) | 1975-03-20 | 1976-03-17 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 3,-diklorfenon-0-(2-aminoetyl)-oximer |
Country Status (26)
Country | Link |
---|---|
US (1) | US4081552A (en, 2012) |
JP (1) | JPS6026777B2 (en, 2012) |
AR (2) | AR211009A1 (en, 2012) |
AT (1) | AT342565B (en, 2012) |
AU (1) | AU505357B2 (en, 2012) |
BE (1) | BE839745A (en, 2012) |
CA (1) | CA1077519A (en, 2012) |
CH (3) | CH626056A5 (en, 2012) |
DD (1) | DD125685A5 (en, 2012) |
DE (1) | DE2609862A1 (en, 2012) |
DK (1) | DK144034C (en, 2012) |
ES (1) | ES446187A1 (en, 2012) |
FI (1) | FI62062C (en, 2012) |
FR (1) | FR2304337A1 (en, 2012) |
GB (1) | GB1531613A (en, 2012) |
GR (1) | GR59317B (en, 2012) |
HU (1) | HU171027B (en, 2012) |
IE (1) | IE43570B1 (en, 2012) |
IL (1) | IL49233A (en, 2012) |
IT (1) | IT1063060B (en, 2012) |
NL (1) | NL7503311A (en, 2012) |
PL (3) | PL100615B1 (en, 2012) |
SE (1) | SE425388B (en, 2012) |
SU (3) | SU670216A3 (en, 2012) |
YU (1) | YU71376A (en, 2012) |
ZA (1) | ZA761209B (en, 2012) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1110460B (it) * | 1977-03-02 | 1985-12-23 | Ciba Geigy Ag | Prodotti che favoriscono la crescita delle piante e prodotti che proteggono le piante a base di eteri di ossime e di esteri di ossime loro preparazione e loro impiego |
CA1321950C (en) * | 1986-10-24 | 1993-09-07 | Robert A.B. Bannard | Metal oximate/polyethylene glycols chemical decontaminant system |
FR2639942B1 (fr) * | 1988-12-02 | 1991-03-29 | Sanofi Sa | Ethers oximes de propenone, procede pour leur preparation et compositions pharmaceutiques les contenant |
HUT54347A (en) * | 1989-01-10 | 1991-02-28 | Chinoin Gyogyszer Es Vegyeszet | Improved process for producing amidoximes |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3692835A (en) * | 1967-04-05 | 1972-09-19 | Jan Van Dijk | Pharmacologically active amino-ethyl oximes |
-
1975
- 1975-03-20 NL NL7503311A patent/NL7503311A/xx not_active Application Discontinuation
-
1976
- 1976-02-27 SE SE7602716A patent/SE425388B/xx not_active IP Right Cessation
- 1976-03-01 ZA ZA761209A patent/ZA761209B/xx unknown
- 1976-03-10 DE DE19762609862 patent/DE2609862A1/de active Granted
- 1976-03-15 AR AR262560A patent/AR211009A1/es active
- 1976-03-17 SU SU762334810A patent/SU670216A3/ru active
- 1976-03-17 CH CH334476A patent/CH626056A5/de not_active IP Right Cessation
- 1976-03-17 PL PL1976188002A patent/PL100615B1/pl unknown
- 1976-03-17 GR GR50334A patent/GR59317B/el unknown
- 1976-03-17 HU HU76PI00000510A patent/HU171027B/hu not_active IP Right Cessation
- 1976-03-17 IT IT21324/76A patent/IT1063060B/it active
- 1976-03-17 CA CA248,106A patent/CA1077519A/en not_active Expired
- 1976-03-17 GB GB10702/76A patent/GB1531613A/en not_active Expired
- 1976-03-17 AT AT195376A patent/AT342565B/de not_active IP Right Cessation
- 1976-03-17 IL IL49233A patent/IL49233A/xx unknown
- 1976-03-17 DK DK115576A patent/DK144034C/da active
- 1976-03-17 FI FI760694A patent/FI62062C/fi not_active IP Right Cessation
- 1976-03-17 PL PL1976199549A patent/PL101884B1/pl unknown
- 1976-03-17 PL PL1976199548A patent/PL100050B1/pl unknown
- 1976-03-18 ES ES446187A patent/ES446187A1/es not_active Expired
- 1976-03-18 AU AU12146/76A patent/AU505357B2/en not_active Expired
- 1976-03-18 IE IE566/76A patent/IE43570B1/en unknown
- 1976-03-18 YU YU00713/76A patent/YU71376A/xx unknown
- 1976-03-18 DD DD191913A patent/DD125685A5/xx unknown
- 1976-03-18 BE BE165317A patent/BE839745A/xx not_active IP Right Cessation
- 1976-03-19 JP JP51029395A patent/JPS6026777B2/ja not_active Expired
- 1976-03-19 FR FR7608020A patent/FR2304337A1/fr active Granted
- 1976-03-19 US US05/668,454 patent/US4081552A/en not_active Expired - Lifetime
- 1976-12-02 AR AR265704A patent/AR212818A1/es active
-
1977
- 1977-07-11 SU SU772500952A patent/SU623517A3/ru active
- 1977-07-12 SU SU772503852A patent/SU626691A3/ru active
-
1981
- 1981-03-06 CH CH153781A patent/CH634828A5/de not_active IP Right Cessation
- 1981-03-06 CH CH153881A patent/CH629760A5/de not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
FI61875C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara trifluormetylfenon-0-(2-aminoetyl)-oximer | |
CN1993346B (zh) | 噻吩化合物 | |
TW397825B (en) | Aroyl-piperidine derivatives | |
JP3989554B2 (ja) | ピペラジンおよびピペリジン化合物 | |
HU186584B (en) | Process for producing new benzodiazepine derivatives | |
DK157920B (da) | Analogifremgangsmaade til fremstilling af indolderivater | |
FI80268C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva 1-pyrimidinyloxi-3-heteroarylalkylamino-2- propanolderivat. | |
US3974158A (en) | 2-(Substituted anilino)methylmorpholines | |
IE47518B1 (en) | Indolo (2,3-a) quinolizidines,preparation and therapeutic use | |
EP0441226A1 (en) | (cyanomethyl)pyridines useful as PAF antagonists | |
FI62062C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 3,-diklorfenon-0-(2-aminoetyl)-oximer | |
JP4221084B2 (ja) | 新規なピペラジン化合物 | |
EP0015615B1 (en) | Phenyl piperazine derivatives, their preparation and antiagressive medicines containing them | |
FI62063B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-klor eller brom-fenon-0-(2-aminoetyl)-oximer | |
GB2142021A (en) | 1 4-dihydropyridine derivatives their preparation and pharmaceutical compositions containing them | |
CS217979B2 (en) | Method of making the cycloalcanonoximether | |
FR2634207A1 (fr) | Derives de ((piperidinyl-4)methyl) benzazepines, leur preparation et leur application en therapeutique | |
IE903388A1 (en) | Phenylakyl amine derivatives having anti-ischaemic activity | |
JPH09249620A (ja) | アリールアルカン誘導体 | |
US4382093A (en) | 9-Aminoalkylfluorenes | |
US4029786A (en) | Morpholine derivatives for treating depression | |
FI62288C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-metyltiofenon-0-(2-aminoetyl)-oximer | |
US4452745A (en) | 9-Aminoalkylfluorenes | |
HU201046B (en) | Process for production of new derivatives of benzodioxol and medical compositions containing them | |
JPS5833872B2 (ja) | ヘキサヒドロジベンゾフラン −3− オンノシンキナユウドウタイオヨビ ソノエンルイノセイゾウホウ |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM | Patent lapsed |
Owner name: DUPHAR INTERNATIONAL RESEARCH B.V |