JPS59176246A - 塩基性オキシムエ−テルの製造方法 - Google Patents

塩基性オキシムエ−テルの製造方法

Info

Publication number: JPS59176246A
Authority: JP; Japan
Prior art keywords: general formula; water; chloro; phenyl; compound
Prior art date: 1983-02-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP59021515A

Other languages

English (en)

Japanese (ja)

Inventor

ゾルターン・ブダイ

テイボル・メゼイ

アランカ・ライ

ルイザ・ペテーツ

カタリン・グラツセル

エニケー・シルト

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Egyt Gyogyszervegyeszeti Gyar

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-02-08

Filing date

1984-02-08

Publication date

1984-10-05

1984-02-08 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1984-10-05 Publication of JPS59176246A publication Critical patent/JPS59176246A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 9
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 40
229910052757 nitrogen Inorganic materials 0.000 claims description 29
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 27
238000000034 method Methods 0.000 claims description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
-1 pyrinone Chemical compound 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000003444 phase transfer catalyst Substances 0.000 claims description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims 3
241000218691 Cupressaceae Species 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
238000004458 analytical method Methods 0.000 description 24
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
239000007858 starting material Substances 0.000 description 18
238000002360 preparation method Methods 0.000 description 17
238000005259 measurement Methods 0.000 description 10
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
150000002923 oximes Chemical class 0.000 description 5
238000004090 dissolution Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 3
239000004914 cyclooctane Substances 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
229960003750 ethyl chloride Drugs 0.000 description 3
238000004880 explosion Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-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
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
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
JECOSSASMXAXFV-UHFFFAOYSA-N chloroethane;hydrochloride Chemical compound Cl.CCCl JECOSSASMXAXFV-UHFFFAOYSA-N 0.000 description 2
238000003912 environmental pollution Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000000926 separation method Methods 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
239000002904 solvent Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
VBWGBXZUJJUARM-UHFFFAOYSA-N 1-(3-chloropropyl)piperazine Chemical compound ClCCCN1CCNCC1 VBWGBXZUJJUARM-UHFFFAOYSA-N 0.000 description 1
MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
ZTXXGFXIJMMZOP-UHFFFAOYSA-N 1-chloropropane;hydrochloride Chemical compound Cl.CCCCl ZTXXGFXIJMMZOP-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
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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
125000005330 8 membered heterocyclic group Chemical group 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
239000012491 analyte Substances 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
239000012736 aqueous medium Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
238000004364 calculation method Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000368 destabilizing effect Effects 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000004134 energy conservation Methods 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
239000002360 explosive Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
239000012071 phase Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
150000003254 radicals Chemical class 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
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000013076 target substance Substances 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
238000005292 vacuum distillation 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)

JP59021515A 1983-02-08 1984-02-08 塩基性オキシムエ−テルの製造方法 Pending JPS59176246A (ja)

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
JPS59176246A true JPS59176246A (ja)	1984-10-05

Family

ID=10949520

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59021515A Pending JPS59176246A (ja)	1983-02-08	1984-02-08	塩基性オキシムエ−テルの製造方法

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)	ES529567A0 (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)

* Cited by examiner, † Cited by third party
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
US5234934A (en) *	1989-08-25	1993-08-10	Egis Gyogyszergyar	Aminopropanol derivatives, process for their preparation and pharmaceutical compositions comprising the same
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

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT339276B (de) *	1976-01-27	1977-10-10	Egyt Gyogyszervegyeszeti Gyar	Verfahren zur herstellung von basischen cycloalkanonoximathern und deren saureadditionssalzen
US4083978A (en) *	1976-01-27	1978-04-11	Egyt Gyogyszervegyeszeti Gyar	Oxime ethers
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 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
- 1984-02-07 GB GB08403235A patent/GB2135995B/en not_active Expired
- 1984-02-08 DE DE19843404478 patent/DE3404478A1/de not_active Withdrawn
- 1984-02-08 JP JP59021515A patent/JPS59176246A/ja active Pending
- 1984-02-08 ES ES529567A patent/ES529567A0/es active Granted
- 1984-02-08 SU SU843702234A patent/SU1304747A3/ru active

Also Published As

Publication number	Publication date
GB2135995B (en)	1986-07-16
FR2540494B1 (fr)	1987-07-17
IT8419470A0 (it)	1984-02-07
AT387016B (de)	1988-11-25
BE898836A (fr)	1984-08-03
GB8403235D0 (en)	1984-03-14
FR2540494A1 (fr)	1984-08-10
IT1196017B (it)	1988-11-10
DE3404478A1 (de)	1984-08-30
CH659246A5 (de)	1987-01-15
SU1304747A3 (ru)	1987-04-15
ATA38884A (de)	1988-04-15
ES8506606A1 (es)	1985-08-01
HU189227B (en)	1986-06-30
ES529567A0 (es)	1985-08-01
GB2135995A (en)	1984-09-12

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