FI65615C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar Download PDFInfo
- Publication number
- FI65615C FI65615C FI760218A FI760218A FI65615C FI 65615 C FI65615 C FI 65615C FI 760218 A FI760218 A FI 760218A FI 760218 A FI760218 A FI 760218A FI 65615 C FI65615 C FI 65615C
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- FI
- Finland
- Prior art keywords
- grams
- moles
- general formula
- symbols
- oxime
- Prior art date
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- 230000001225 therapeutic effect Effects 0.000 title description 4
- 238000002496 oximetry Methods 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 oxime ethers Chemical class 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- 150000002923 oximes Chemical class 0.000 claims description 13
- 239000012442 inert solvent Substances 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 150000002443 hydroxylamines Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 101100048435 Caenorhabditis elegans unc-18 gene Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 42
- 239000012312 sodium hydride Substances 0.000 description 41
- 229910000104 sodium hydride Inorganic materials 0.000 description 41
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 34
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 33
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 11
- VTJALIBWBDVIMV-UHFFFAOYSA-N 2-(3-chloropropyl)-1-methylpiperazine Chemical compound CN1CCNCC1CCCCl VTJALIBWBDVIMV-UHFFFAOYSA-N 0.000 description 10
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- JDMKEINRMVQHKR-ZFDSPDROSA-N (nz)-n-[(2e)-2-benzylidenecyclopentylidene]hydroxylamine Chemical compound O\N=C/1\CCC\C\1=C/C1=CC=CC=C1 JDMKEINRMVQHKR-ZFDSPDROSA-N 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- FQJDUWXFZXKOSV-UHFFFAOYSA-N 1-benzyl-2-(3-chloropropyl)piperazine Chemical compound ClCCCC1CNCCN1CC1=CC=CC=C1 FQJDUWXFZXKOSV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RWOLAHHEUZXIJZ-HBKPYOMSSA-N (ne)-n-[(2e)-2-benzylidenecyclohexylidene]hydroxylamine Chemical compound O\N=C\1/CCCC/C/1=C\C1=CC=CC=C1 RWOLAHHEUZXIJZ-HBKPYOMSSA-N 0.000 description 5
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 5
- 229960004194 lidocaine Drugs 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 4
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 4
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229960002715 nicotine Drugs 0.000 description 4
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 4
- 229960001789 papaverine Drugs 0.000 description 4
- 230000036515 potency Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMVAURSKUUIJKT-UHFFFAOYSA-N 1-chloro-n,n,2-trimethylpropan-1-amine Chemical compound CC(C)C(Cl)N(C)C YMVAURSKUUIJKT-UHFFFAOYSA-N 0.000 description 3
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 230000003444 anaesthetic effect Effects 0.000 description 3
- 239000005557 antagonist Substances 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
- 239000003589 local anesthetic agent Substances 0.000 description 3
- KGJPPTQTKGKOOY-UHFFFAOYSA-N n-(2-benzylidenecycloheptylidene)hydroxylamine Chemical compound ON=C1CCCCCC1=CC1=CC=CC=C1 KGJPPTQTKGKOOY-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CFWDBIGLDIDEGN-UHFFFAOYSA-N n-[2-[(3-methoxyphenyl)methylidene]cyclohexylidene]hydroxylamine Chemical compound COC1=CC=CC(C=C2C(CCCC2)=NO)=C1 CFWDBIGLDIDEGN-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 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 2
- WWQVYILGLAQPLU-YPKPFQOOSA-N (NZ)-N-(2-benzylcyclohexylidene)hydroxylamine Chemical compound O\N=C1\CCCCC1CC1=CC=CC=C1 WWQVYILGLAQPLU-YPKPFQOOSA-N 0.000 description 2
- 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
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- NKDPYAUUWQQBNV-UHFFFAOYSA-N C1=CC(OC)=CC=C1CC1C(=NO)CCCC1 Chemical compound C1=CC(OC)=CC=C1CC1C(=NO)CCCC1 NKDPYAUUWQQBNV-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
- RLDHBPJLLDXGQM-UHFFFAOYSA-N N-[2-[(4-chlorophenyl)methyl]cyclohexylidene]hydroxylamine Chemical compound ON=C1CCCCC1CC1=CC=C(Cl)C=C1 RLDHBPJLLDXGQM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229940109275 cyclamate Drugs 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 description 2
- YIUNSWVHBJKYGU-UHFFFAOYSA-N n-[2-[(2-chlorophenyl)methylidene]cyclohexylidene]hydroxylamine Chemical compound ON=C1CCCCC1=CC1=CC=CC=C1Cl YIUNSWVHBJKYGU-UHFFFAOYSA-N 0.000 description 2
- KQYYSPLKEWHYAN-UHFFFAOYSA-N n-[2-[(2-methoxyphenyl)methylidene]cyclohexylidene]hydroxylamine Chemical compound COC1=CC=CC=C1C=C1C(=NO)CCCC1 KQYYSPLKEWHYAN-UHFFFAOYSA-N 0.000 description 2
- YRZHYMWDDRYZFN-UHFFFAOYSA-N n-[2-[(3-chlorophenyl)methylidene]cyclohexylidene]hydroxylamine Chemical compound ON=C1CCCCC1=CC1=CC=CC(Cl)=C1 YRZHYMWDDRYZFN-UHFFFAOYSA-N 0.000 description 2
- FRNGIUXKDJKDSJ-UHFFFAOYSA-N o-[2-(dimethylamino)ethyl]hydroxylamine;hydrochloride Chemical compound Cl.CN(C)CCON FRNGIUXKDJKDSJ-UHFFFAOYSA-N 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- 229960005333 tetrabenazine Drugs 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- WKEXENOSHSPMMW-PKNBQFBNSA-N (2e)-2-[(4-nitrophenyl)methylidene]cyclohexan-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C/1C(=O)CCCC\1 WKEXENOSHSPMMW-PKNBQFBNSA-N 0.000 description 1
- ZFJFROHCPHULKY-PKNBQFBNSA-N (2e)-2-benzylidenecyclopentan-1-one Chemical compound O=C1CCC\C1=C/C1=CC=CC=C1 ZFJFROHCPHULKY-PKNBQFBNSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- ZKDOQFPDSUOLGF-UHFFFAOYSA-N 1-bromo-3-chloro-2-methylpropane Chemical compound ClCC(C)CBr ZKDOQFPDSUOLGF-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- OCABCUFCZLXPSR-UHFFFAOYSA-N 2-(1-chloro-2-methylpropyl)-1-methylpiperazine Chemical compound CC(C)C(Cl)C1CNCCN1C OCABCUFCZLXPSR-UHFFFAOYSA-N 0.000 description 1
- UKEZYSPSOKPWHY-UHFFFAOYSA-N 2-[(3,4,5-trimethoxyphenyl)methylidene]cyclohexan-1-one Chemical compound COC1=C(OC)C(OC)=CC(C=C2C(CCCC2)=O)=C1 UKEZYSPSOKPWHY-UHFFFAOYSA-N 0.000 description 1
- VTVVPTRDNLXHFT-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylidene]cyclohexan-1-one Chemical compound C1=CC(Cl)=CC=C1C=C1C(=O)CCCC1 VTVVPTRDNLXHFT-UHFFFAOYSA-N 0.000 description 1
- DZWSEDDDYDXRMV-UHFFFAOYSA-N 2-benzylidene-N-(3-morpholin-4-ylpropoxy)cyclohexan-1-imine Chemical compound C(C1=CC=CC=C1)=C1C(CCCC1)=NOCCCN1CCOCC1 DZWSEDDDYDXRMV-UHFFFAOYSA-N 0.000 description 1
- PCRAENZAWCWMHN-UHFFFAOYSA-N 2-benzylidene-n-[2-methyl-3-(4-methylpiperazin-1-yl)propoxy]cyclohexan-1-imine Chemical compound C1CN(C)CCN1CC(C)CON=C1CCCCC1=CC1=CC=CC=C1 PCRAENZAWCWMHN-UHFFFAOYSA-N 0.000 description 1
- GGIIDXTZUUOCEG-UHFFFAOYSA-N 2-benzylidene-n-[3-(4-methylpiperazin-1-yl)propoxy]cyclopentan-1-imine Chemical compound C1CN(C)CCN1CCCON=C(CCC1)C1=CC1=CC=CC=C1 GGIIDXTZUUOCEG-UHFFFAOYSA-N 0.000 description 1
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- RQLJVYAATHXNBC-UHFFFAOYSA-N 3-[[2-[(2-chlorophenyl)methylidene]cyclohexylidene]amino]oxy-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCON=C1CCCCC1=CC1=CC=CC=C1Cl RQLJVYAATHXNBC-UHFFFAOYSA-N 0.000 description 1
- UIYHDWYSKFOMNM-UHFFFAOYSA-N 3-[[2-[(3-chlorophenyl)methylidene]cyclohexylidene]amino]oxy-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCON=C1CCCCC1=CC1=CC=CC(Cl)=C1 UIYHDWYSKFOMNM-UHFFFAOYSA-N 0.000 description 1
- DLJHVWODIGKWCV-UHFFFAOYSA-N 3-[[2-[(4-chlorophenyl)methylidene]cyclohexylidene]amino]oxy-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCON=C1CCCCC1=CC1=CC=C(Cl)C=C1 DLJHVWODIGKWCV-UHFFFAOYSA-N 0.000 description 1
- UGXACBBAXFABGT-UHFFFAOYSA-N 3-chloro-n,n,2-trimethylpropan-1-amine Chemical compound ClCC(C)CN(C)C UGXACBBAXFABGT-UHFFFAOYSA-N 0.000 description 1
- PIAZYBLGBSMNLX-UHFFFAOYSA-N 4-(3-chloropropyl)morpholine Chemical compound ClCCCN1CCOCC1 PIAZYBLGBSMNLX-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- DNFQVHZDHIGIAO-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.CN(C)CCON=C1C(CCCC1)=CC1=CC=C(C=C1)[N+](=O)[O-] Chemical compound C(C=CC(=O)O)(=O)O.CN(C)CCON=C1C(CCCC1)=CC1=CC=C(C=C1)[N+](=O)[O-] DNFQVHZDHIGIAO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VNCUKATURIDCKZ-UHFFFAOYSA-N N-[2-[(4-chlorophenyl)methylidene]cycloheptylidene]hydroxylamine Chemical compound ON=C1CCCCCC1=CC1=CC=C(Cl)C=C1 VNCUKATURIDCKZ-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 230000001665 lethal effect Effects 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
- VEVFPJBPTVTLNR-UHFFFAOYSA-N n-(2-benzylidenecyclooctylidene)hydroxylamine Chemical compound ON=C1CCCCCCC1=CC1=CC=CC=C1 VEVFPJBPTVTLNR-UHFFFAOYSA-N 0.000 description 1
- FOYCCPPJHYCVML-UHFFFAOYSA-N n-[2-[(3,4-dimethoxyphenyl)methylidene]cyclohexylidene]hydroxylamine Chemical compound C1=C(OC)C(OC)=CC=C1C=C1C(=NO)CCCC1 FOYCCPPJHYCVML-UHFFFAOYSA-N 0.000 description 1
- RJALIFJBMFCTOY-UHFFFAOYSA-N n-[2-[(4-chlorophenyl)methylidene]cyclohexylidene]hydroxylamine Chemical compound ON=C1CCCCC1=CC1=CC=C(Cl)C=C1 RJALIFJBMFCTOY-UHFFFAOYSA-N 0.000 description 1
- HOIQACZINNKHTN-UHFFFAOYSA-N n-[2-[(4-methoxyphenyl)methylidene]cycloheptylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1C=C1C(=NO)CCCCC1 HOIQACZINNKHTN-UHFFFAOYSA-N 0.000 description 1
- YKKUXOGVLHUDNF-UHFFFAOYSA-N n-[2-[(4-methoxyphenyl)methylidene]cyclohexylidene]hydroxylamine Chemical compound C1=CC(OC)=CC=C1C=C1C(=NO)CCCC1 YKKUXOGVLHUDNF-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- WMAVKPNBVWRHGC-UHFFFAOYSA-N o-[2-(diethylamino)ethyl]hydroxylamine;hydrochloride Chemical compound Cl.CCN(CC)CCON WMAVKPNBVWRHGC-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 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
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229960001032 trihexyphenidyl Drugs 0.000 description 1
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3176/76A GB1493222A (en) | 1976-01-27 | 1976-01-27 | Cycloalkanone oxime ethers and process for the preparation thereof |
| DK32576A DK149043C (da) | 1976-01-27 | 1976-01-27 | Analogifremgangsmaade til fremstilling af 2-benzal- eller 2-benzyl-1-(aminoalkoxyimino)-cykloalkaner eller salte eller kvaternaere ammoniumderivater deraf |
| US05/652,806 US4083978A (en) | 1976-01-27 | 1976-01-27 | Oxime ethers |
| FI760218A FI65615C (fi) | 1976-01-27 | 1976-01-29 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar |
| FR7602460A FR2339397A1 (fr) | 1976-01-27 | 1976-01-29 | Nouveaux ethers d'oximes, procede de preparation de ceux-ci et medicaments les contenant |
| SE7600969A SE410733B (sv) | 1976-01-27 | 1976-01-29 | Sett att framstella vissa angivna oximetrar |
| NLAANVRAGE7600945,A NL180585C (nl) | 1976-01-27 | 1976-01-30 | Werkwijze voor de bereiding van oxim-ethers, alsmede werkwijze voor de bereiding of vervaardiging van farmaceutische preparaten die deze bevatten. |
| BE164044A BE838213A (fr) | 1976-01-27 | 1976-02-03 | Nouveaux ethers d'oximes, procede de preparation de ceux-ci et medicaments les contenant |
| CA245,043A CA1071201A (en) | 1976-01-27 | 1976-02-04 | Oxime ethers and process for the preparation thereof |
| JP1273676A JPS5295643A (en) | 1976-01-27 | 1976-02-07 | Oxim ether and process for preparing same |
| AT813776A AT342019B (de) | 1976-01-27 | 1976-02-23 | Verfahren zur herstellung von basischen cycloalkanonoximathern und deren saureadditionssalzen |
| AT125076A AT339276B (de) | 1976-01-27 | 1976-02-23 | Verfahren zur herstellung von basischen cycloalkanonoximathern und deren saureadditionssalzen |
| CH223676A CH626058A5 (en) | 1976-01-27 | 1976-02-24 | Process for the preparation of basic oxime ethers |
| DD191525A DD125547A5 (cs) | 1976-01-27 | 1976-02-26 | |
| DE2609017A DE2609017C3 (de) | 1976-01-27 | 1976-03-04 | Basische Oximäther, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzeimittel |
| US05/749,399 US4077999A (en) | 1976-01-27 | 1976-12-10 | Novel oxime ethers |
Applications Claiming Priority (32)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK32576 | 1976-01-27 | ||
| US65280676 | 1976-01-27 | ||
| US05/652,806 US4083978A (en) | 1976-01-27 | 1976-01-27 | Oxime ethers |
| DK32576A DK149043C (da) | 1976-01-27 | 1976-01-27 | Analogifremgangsmaade til fremstilling af 2-benzal- eller 2-benzyl-1-(aminoalkoxyimino)-cykloalkaner eller salte eller kvaternaere ammoniumderivater deraf |
| GB317676 | 1976-01-27 | ||
| GB3176/76A GB1493222A (en) | 1976-01-27 | 1976-01-27 | Cycloalkanone oxime ethers and process for the preparation thereof |
| FR7602460 | 1976-01-29 | ||
| FR7602460A FR2339397A1 (fr) | 1976-01-27 | 1976-01-29 | Nouveaux ethers d'oximes, procede de preparation de ceux-ci et medicaments les contenant |
| FI760218 | 1976-01-29 | ||
| SE7600969A SE410733B (sv) | 1976-01-27 | 1976-01-29 | Sett att framstella vissa angivna oximetrar |
| FI760218A FI65615C (fi) | 1976-01-27 | 1976-01-29 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar |
| SE7600969 | 1976-01-29 | ||
| NL7600945 | 1976-01-30 | ||
| NLAANVRAGE7600945,A NL180585C (nl) | 1976-01-27 | 1976-01-30 | Werkwijze voor de bereiding van oxim-ethers, alsmede werkwijze voor de bereiding of vervaardiging van farmaceutische preparaten die deze bevatten. |
| BE164044A BE838213A (fr) | 1976-01-27 | 1976-02-03 | Nouveaux ethers d'oximes, procede de preparation de ceux-ci et medicaments les contenant |
| BE164044 | 1976-02-03 | ||
| CA245043 | 1976-02-04 | ||
| CA245,043A CA1071201A (en) | 1976-01-27 | 1976-02-04 | Oxime ethers and process for the preparation thereof |
| JP1273676A JPS5295643A (en) | 1976-01-27 | 1976-02-07 | Oxim ether and process for preparing same |
| JP1273676 | 1976-02-07 | ||
| AT813776 | 1976-02-23 | ||
| AT125076 | 1976-02-23 | ||
| AT125076A AT339276B (de) | 1976-01-27 | 1976-02-23 | Verfahren zur herstellung von basischen cycloalkanonoximathern und deren saureadditionssalzen |
| AT813776A AT342019B (de) | 1976-01-27 | 1976-02-23 | Verfahren zur herstellung von basischen cycloalkanonoximathern und deren saureadditionssalzen |
| CH223676 | 1976-02-24 | ||
| CH223676A CH626058A5 (en) | 1976-01-27 | 1976-02-24 | Process for the preparation of basic oxime ethers |
| DD19152576 | 1976-02-26 | ||
| DD191525A DD125547A5 (cs) | 1976-01-27 | 1976-02-26 | |
| DE2609017A DE2609017C3 (de) | 1976-01-27 | 1976-03-04 | Basische Oximäther, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzeimittel |
| DE2609017 | 1976-03-04 | ||
| US05/749,399 US4077999A (en) | 1976-01-27 | 1976-12-10 | Novel oxime ethers |
| US74939976 | 1976-12-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI760218A7 FI760218A7 (cs) | 1977-07-30 |
| FI65615B FI65615B (fi) | 1984-02-29 |
| FI65615C true FI65615C (fi) | 1984-06-11 |
Family
ID=27585558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI760218A FI65615C (fi) | 1976-01-27 | 1976-01-29 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5295643A (cs) |
| AT (1) | AT342019B (cs) |
| BE (1) | BE838213A (cs) |
| CA (1) | CA1071201A (cs) |
| CH (1) | CH626058A5 (cs) |
| DD (1) | DD125547A5 (cs) |
| DE (1) | DE2609017C3 (cs) |
| DK (1) | DK149043C (cs) |
| FI (1) | FI65615C (cs) |
| FR (1) | FR2339397A1 (cs) |
| GB (1) | GB1493222A (cs) |
| NL (1) | NL180585C (cs) |
| SE (1) | SE410733B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2658938A1 (de) * | 1976-12-24 | 1978-07-06 | Hoechst Ag | Neue basisch substituierte 0-propyloxime, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| HU180739B (en) * | 1979-07-03 | 1983-04-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing basic oxime-ethers |
| FR2518090A1 (fr) * | 1981-12-11 | 1983-06-17 | Univablot | Ethers d'oximes a-b insatures, leur procede de preparation et leur utilisation comme medicament |
| HU190387B (en) * | 1982-05-25 | 1986-08-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for producing 2-bracket-z-bracket closed-phenyl-methylene-cycloheptane derivatives |
| HU188250B (en) * | 1983-02-08 | 1986-03-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for producing of basical oxim-ethers |
| HU189226B (en) * | 1983-02-08 | 1986-06-30 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for producing basic oxime-ethers |
| HU197205B (en) * | 1984-07-10 | 1989-03-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of medical compositions against angine |
| HU202195B (en) * | 1987-12-31 | 1991-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new substituted styrene derivatives and medical compositions comprising such compounds |
| CA2006309C (fr) * | 1988-12-29 | 2001-12-18 | Jean Hutt | Azolylmethylcyclopentane benzylidene fongicide |
| HU212415B (en) * | 1989-08-25 | 1996-06-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new cyclic oxym derivatives and pharmaceutical compositions containing them as active components |
| HUT67314A (en) * | 1993-04-09 | 1995-03-28 | Egyt Gyogyszervegyeszeti Gyar | Process for prepg. new trisubstituted cykloalkane deriv.s and pharmaceutical compn.s contg. them |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3262975A (en) | 1963-02-12 | 1966-07-26 | Upjohn Co | 1-chloro-3, 4-dihydro 2-naphthaldehyde oxime and ethers thereof |
| US3937841A (en) | 1967-04-05 | 1976-02-10 | U.S. Philips Corporation | Treatment of depression |
| CH512184A (de) | 1969-08-06 | 1971-09-15 | Ciba Geigy Ag | Verwendung von Cyclohexanon- resp. Cyclohexenon-N-Alkylcarbamoyloximen zur Bekämpfung von Zecken |
| CA943138A (en) | 1969-11-10 | 1974-03-05 | Don R. Baker | Certain oxime compositions and their use in controlling fungi |
| US3928446A (en) | 1974-04-11 | 1975-12-23 | Hoffmann La Roche | Preparation of 3-oxo-19-nor-{66 {hu 4{b -steroids from 10-{8 3-substituted-alkyl{9 -desasteroids |
-
1976
- 1976-01-27 GB GB3176/76A patent/GB1493222A/en not_active Expired
- 1976-01-27 DK DK32576A patent/DK149043C/da not_active IP Right Cessation
- 1976-01-29 FI FI760218A patent/FI65615C/fi not_active IP Right Cessation
- 1976-01-29 FR FR7602460A patent/FR2339397A1/fr active Granted
- 1976-01-29 SE SE7600969A patent/SE410733B/xx not_active IP Right Cessation
- 1976-01-30 NL NLAANVRAGE7600945,A patent/NL180585C/xx not_active IP Right Cessation
- 1976-02-03 BE BE164044A patent/BE838213A/xx not_active IP Right Cessation
- 1976-02-04 CA CA245,043A patent/CA1071201A/en not_active Expired
- 1976-02-07 JP JP1273676A patent/JPS5295643A/ja active Granted
- 1976-02-23 AT AT813776A patent/AT342019B/de not_active IP Right Cessation
- 1976-02-24 CH CH223676A patent/CH626058A5/de not_active IP Right Cessation
- 1976-02-26 DD DD191525A patent/DD125547A5/xx unknown
- 1976-03-04 DE DE2609017A patent/DE2609017C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI760218A7 (cs) | 1977-07-30 |
| DK32576A (da) | 1977-07-28 |
| JPS5715746B2 (cs) | 1982-04-01 |
| DK149043C (da) | 1986-05-26 |
| DE2609017A1 (de) | 1977-09-08 |
| DK149043B (da) | 1985-12-30 |
| FR2339397B1 (cs) | 1979-10-05 |
| NL7600945A (nl) | 1977-08-02 |
| CH626058A5 (en) | 1981-10-30 |
| JPS5295643A (en) | 1977-08-11 |
| NL180585C (nl) | 1987-03-16 |
| GB1493222A (en) | 1977-11-30 |
| FI65615B (fi) | 1984-02-29 |
| SE7600969L (sv) | 1977-07-30 |
| NL180585B (nl) | 1986-10-16 |
| DD125547A5 (cs) | 1977-05-04 |
| SE410733B (sv) | 1979-10-29 |
| DE2609017C3 (de) | 1981-05-27 |
| BE838213A (fr) | 1976-05-28 |
| DE2609017B2 (de) | 1980-10-09 |
| CA1071201A (en) | 1980-02-05 |
| AT342019B (de) | 1978-03-10 |
| ATA813776A (de) | 1977-07-15 |
| FR2339397A1 (fr) | 1977-08-26 |
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Owner name: EGYT GYOGYSZERVEGYESZETI GYAR |