HU189227B - Process for preparing basic oxime-ethers - Google Patents
Process for preparing basic oxime-ethers Download PDFInfo
- Publication number
- HU189227B HU189227B HU83416A HU41683A HU189227B HU 189227 B HU189227 B HU 189227B HU 83416 A HU83416 A HU 83416A HU 41683 A HU41683 A HU 41683A HU 189227 B HU189227 B HU 189227B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- oxime
- mol
- water
- phenyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- -1 oxime ethers Chemical class 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 150000002923 oximes Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- VTVVPTRDNLXHFT-PKNBQFBNSA-N (2e)-2-[(4-chlorophenyl)methylidene]cyclohexan-1-one Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(=O)CCCC\1 VTVVPTRDNLXHFT-PKNBQFBNSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000002366 halogen compounds Chemical class 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 29
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 125000002947 alkylene group Chemical group 0.000 abstract description 3
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- BQCRDGOBIZRDJH-ACCUITESSA-N (2e)-2-benzylidenecycloheptan-1-one Chemical compound O=C1CCCCC\C1=C/C1=CC=CC=C1 BQCRDGOBIZRDJH-ACCUITESSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- VCDPHYIZVFJQCD-ZRDIBKRKSA-N (2e)-2-benzylidenecyclohexan-1-one Chemical compound O=C1CCCC\C1=C/C1=CC=CC=C1 VCDPHYIZVFJQCD-ZRDIBKRKSA-N 0.000 description 3
- AUERUDPETOKUPT-UHFFFAOYSA-N 1-(3-chloropropyl)-4-methylpiperazine Chemical compound CN1CCN(CCCCl)CC1 AUERUDPETOKUPT-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002360 explosive Substances 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YHAZKHJHHOWKSR-ZRDIBKRKSA-N (2E)-2-benzylidenecyclohex-3-en-1-one Chemical compound O=C1CCC=C\C1=C/C1=CC=CC=C1 YHAZKHJHHOWKSR-ZRDIBKRKSA-N 0.000 description 2
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylamino-1-chloro-ethane hydrochloride Natural products CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000004914 cyclooctane Substances 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VTDQASDBYAELFK-FMIVXFBMSA-N (2e)-2-[(3-chlorophenyl)methylidene]cycloheptan-1-one Chemical compound ClC1=CC=CC(\C=C/2C(CCCCC\2)=O)=C1 VTDQASDBYAELFK-FMIVXFBMSA-N 0.000 description 1
- UHBAGVCCVHTJFI-DHZHZOJOSA-N (2e)-2-[(3-chlorophenyl)methylidene]cyclohexan-1-one Chemical compound ClC1=CC=CC(\C=C/2C(CCCC\2)=O)=C1 UHBAGVCCVHTJFI-DHZHZOJOSA-N 0.000 description 1
- ADVRWTWVDZKNFF-WYMLVPIESA-N (2e)-2-benzylidenecyclooctan-1-one Chemical compound O=C1CCCCCC\C1=C/C1=CC=CC=C1 ADVRWTWVDZKNFF-WYMLVPIESA-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
- BQCRDGOBIZRDJH-QBFSEMIESA-N (2z)-2-benzylidenecycloheptan-1-one Chemical compound O=C1CCCCC\C1=C\C1=CC=CC=C1 BQCRDGOBIZRDJH-QBFSEMIESA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- PZPFCXFBXLZYMQ-UHFFFAOYSA-N 1-benzyl-4-(3-chloropropyl)piperazine;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCCl)CCN1CC1=CC=CC=C1 PZPFCXFBXLZYMQ-UHFFFAOYSA-N 0.000 description 1
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- NIMCYKIIHOXLPD-UHFFFAOYSA-N 2-benzylcycloheptan-1-one Chemical compound O=C1CCCCCC1CC1=CC=CC=C1 NIMCYKIIHOXLPD-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- VJQULJPYVAJZKN-UHFFFAOYSA-N 3-chloro-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.CC(C)N(C(C)C)CCCCl VJQULJPYVAJZKN-UHFFFAOYSA-N 0.000 description 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
- PQECODMSWJOUAT-UHFFFAOYSA-N 4-(3-chloropropyl)morpholine;hydrochloride Chemical compound [Cl-].ClCCC[NH+]1CCOCC1 PQECODMSWJOUAT-UHFFFAOYSA-N 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WLJWJNVRHSXTIL-LNZAWAQUSA-N C1(=CC=CC=C1)\C=C/1\C(\CCCCC1)=N\OCCCN1CCN(CC1)C Chemical compound C1(=CC=CC=C1)\C=C/1\C(\CCCCC1)=N\OCCCN1CCN(CC1)C WLJWJNVRHSXTIL-LNZAWAQUSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- JECOSSASMXAXFV-UHFFFAOYSA-N chloroethane;hydrochloride Chemical compound Cl.CCCl JECOSSASMXAXFV-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NARWYSCMDPLCIQ-UHFFFAOYSA-N ethane;hydrochloride Chemical compound Cl.CC NARWYSCMDPLCIQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IUSXYVRFJVAVOB-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine;hydron;chloride Chemical compound Cl.CC(C)N(C(C)C)CCCl IUSXYVRFJVAVOB-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU83416A HU189227B (en) | 1983-02-08 | 1983-02-08 | Process for preparing basic oxime-ethers |
| CH481/84A CH659246A5 (de) | 1983-02-08 | 1984-02-02 | Verfahren zur herstellung von basischen oximaethern. |
| BE1/010953A BE898836A (fr) | 1983-02-08 | 1984-02-03 | Procede pour la preparation d'oxime ethers basiques |
| AT0038884A AT387016B (de) | 1983-02-08 | 1984-02-07 | Verfahren zur herstellung von basischen oximaethern und ihren salzen |
| IT19470/84A IT1196017B (it) | 1983-02-08 | 1984-02-07 | Procedimento di preparazione per eteri ossimici basici |
| FR8401834A FR2540494B1 (fr) | 1983-02-08 | 1984-02-07 | Procede pour la preparation d'oxime ethers basiques |
| GB08403235A GB2135995B (en) | 1983-02-08 | 1984-02-07 | Process for the preparation of basic oxime ethers |
| SU843702234A SU1304747A3 (ru) | 1983-02-08 | 1984-02-08 | Способ получени основных простых эфиров оксимов или их солей |
| ES529567A ES8506606A1 (es) | 1983-02-08 | 1984-02-08 | Procedimiento de preparacion de eteres oximas basicos y de sus sales de adicion acidas |
| DE19843404478 DE3404478A1 (de) | 1983-02-08 | 1984-02-08 | Verfahren zur herstellung von basischen cycloalkanonoximaethern |
| JP59021515A JPS59176246A (ja) | 1983-02-08 | 1984-02-08 | 塩基性オキシムエ−テルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU83416A HU189227B (en) | 1983-02-08 | 1983-02-08 | Process for preparing basic oxime-ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189227B true HU189227B (en) | 1986-06-30 |
Family
ID=10949520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU83416A HU189227B (en) | 1983-02-08 | 1983-02-08 | Process for preparing basic oxime-ethers |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS59176246A (de) |
| AT (1) | AT387016B (de) |
| BE (1) | BE898836A (de) |
| CH (1) | CH659246A5 (de) |
| DE (1) | DE3404478A1 (de) |
| ES (1) | ES8506606A1 (de) |
| FR (1) | FR2540494B1 (de) |
| GB (1) | GB2135995B (de) |
| HU (1) | HU189227B (de) |
| IT (1) | IT1196017B (de) |
| SU (1) | SU1304747A3 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU202195B (en) * | 1987-12-31 | 1991-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing new substituted styrene derivatives and medical compositions comprising such compounds |
| 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 |
| US5234934A (en) * | 1989-08-25 | 1993-08-10 | Egis Gyogyszergyar | Aminopropanol derivatives, process for their preparation and pharmaceutical compositions comprising the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4083978A (en) * | 1976-01-27 | 1978-04-11 | Egyt Gyogyszervegyeszeti Gyar | Oxime ethers |
| AT339276B (de) * | 1976-01-27 | 1977-10-10 | Egyt Gyogyszervegyeszeti Gyar | Verfahren zur herstellung von basischen cycloalkanonoximathern und deren saureadditionssalzen |
| SU633472A3 (ru) * | 1976-02-13 | 1978-11-15 | Эдьт Дьедьсерведьесети Дьяр, (Инопредприятие) | Способ получени оксимэфиров, их солей или их четвертичных аммониевых солей |
| HU180739B (en) * | 1979-07-03 | 1983-04-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing basic oxime-ethers |
| DE2927117A1 (de) * | 1979-07-05 | 1981-01-08 | Basf Ag | Verfahren zur herstellung von o-substituierten ketoximen |
-
1983
- 1983-02-08 HU HU83416A patent/HU189227B/hu not_active IP Right Cessation
-
1984
- 1984-02-02 CH CH481/84A patent/CH659246A5/de not_active IP Right Cessation
- 1984-02-03 BE BE1/010953A patent/BE898836A/fr not_active IP Right Cessation
- 1984-02-07 GB GB08403235A patent/GB2135995B/en not_active Expired
- 1984-02-07 AT AT0038884A patent/AT387016B/de not_active IP Right Cessation
- 1984-02-07 IT IT19470/84A patent/IT1196017B/it active
- 1984-02-07 FR FR8401834A patent/FR2540494B1/fr not_active Expired
- 1984-02-08 JP JP59021515A patent/JPS59176246A/ja active Pending
- 1984-02-08 SU SU843702234A patent/SU1304747A3/ru active
- 1984-02-08 DE DE19843404478 patent/DE3404478A1/de not_active Withdrawn
- 1984-02-08 ES ES529567A patent/ES8506606A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3404478A1 (de) | 1984-08-30 |
| ATA38884A (de) | 1988-04-15 |
| BE898836A (fr) | 1984-08-03 |
| IT1196017B (it) | 1988-11-10 |
| SU1304747A3 (ru) | 1987-04-15 |
| GB2135995A (en) | 1984-09-12 |
| CH659246A5 (de) | 1987-01-15 |
| FR2540494B1 (fr) | 1987-07-17 |
| JPS59176246A (ja) | 1984-10-05 |
| ES529567A0 (es) | 1985-08-01 |
| GB8403235D0 (en) | 1984-03-14 |
| GB2135995B (en) | 1986-07-16 |
| AT387016B (de) | 1988-11-25 |
| FR2540494A1 (fr) | 1984-08-10 |
| IT8419470A0 (it) | 1984-02-07 |
| ES8506606A1 (es) | 1985-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |