SU440824A1 - - Google Patents
Info
- Publication number
- SU440824A1 SU440824A1 SU1820134A SU1820134A SU440824A1 SU 440824 A1 SU440824 A1 SU 440824A1 SU 1820134 A SU1820134 A SU 1820134A SU 1820134 A SU1820134 A SU 1820134A SU 440824 A1 SU440824 A1 SU 440824A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloro
- trifluoromethylphenyl
- ether
- hydrochloride
- acid
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- -1 6-chloro-3-trifluoromethylphenyl Chemical group 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- HZSSZTZLKVHTEA-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-amine Chemical compound CC(N)CC1=CC=C(Cl)C(C(F)(F)F)=C1 HZSSZTZLKVHTEA-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DOAYDKOKRCGVOP-UHFFFAOYSA-N 2-chloro-n-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-yl]acetamide Chemical compound ClCC(=O)NC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 DOAYDKOKRCGVOP-UHFFFAOYSA-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
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZPXGOEITMQMUJX-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]propan-2-one Chemical compound CC(=O)CC1=CC(C(F)(F)F)=CC=C1Cl ZPXGOEITMQMUJX-UHFFFAOYSA-N 0.000 description 1
- PUBKPEHSUMNHKV-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-2-methylpropan-2-amine Chemical compound CC(C)(N)CC1=CC=C(Cl)C(C(F)(F)F)=C1 PUBKPEHSUMNHKV-UHFFFAOYSA-N 0.000 description 1
- NREUBTUYADXMHQ-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(CCl)=CC=C1Cl NREUBTUYADXMHQ-UHFFFAOYSA-N 0.000 description 1
- OJZHQPYRNNWXJU-UHFFFAOYSA-N 2-(benzylamino)-n-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-yl]acetamide Chemical compound C=1C=CC=CC=1CNCC(=O)NC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 OJZHQPYRNNWXJU-UHFFFAOYSA-N 0.000 description 1
- VPUGDWFTOZMWPD-UHFFFAOYSA-N 2-(benzylamino)-n-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-yl]acetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CNCC(=O)NC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 VPUGDWFTOZMWPD-UHFFFAOYSA-N 0.000 description 1
- PXUPYSJLILBVTG-UHFFFAOYSA-N 2-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-ylamino]ethanol Chemical compound OCCNC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 PXUPYSJLILBVTG-UHFFFAOYSA-N 0.000 description 1
- XMVOBLWNRZRDSI-UHFFFAOYSA-N 2-amino-n-[1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-yl]acetamide Chemical compound NCC(=O)NC(C)CC1=CC=C(Cl)C(C(F)(F)F)=C1 XMVOBLWNRZRDSI-UHFFFAOYSA-N 0.000 description 1
- IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 description 1
- SHWUYQDIJUWTPM-UHFFFAOYSA-N 2-chloro-n-propylacetamide Chemical compound CCCNC(=O)CCl SHWUYQDIJUWTPM-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- IEDYCRZGGDPBHA-UHFFFAOYSA-N Cl.ClC1=C(C=C(C=C1)CC(C)NCCCO)C(F)(F)F Chemical compound Cl.ClC1=C(C=C(C=C1)CC(C)NCCCO)C(F)(F)F IEDYCRZGGDPBHA-UHFFFAOYSA-N 0.000 description 1
- UDILIOSVLJDZLA-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)(O)C)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)(O)C)C(F)(F)F UDILIOSVLJDZLA-UHFFFAOYSA-N 0.000 description 1
- YVBMGWOVQHCXKE-UHFFFAOYSA-N ClC1=C(C=C(C=C1)CC(C)NCC(C1=CC=CC=C1)O)C(F)(F)F Chemical compound ClC1=C(C=C(C=C1)CC(C)NCC(C1=CC=CC=C1)O)C(F)(F)F YVBMGWOVQHCXKE-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- XIMNNJBJXXEBTH-UHFFFAOYSA-N N-(3-chloropropyl)-1-[4-chloro-3-(trifluoromethyl)phenyl]propan-2-amine Chemical compound ClC1=C(C=C(C=C1)CC(C)NCCCCl)C(F)(F)F XIMNNJBJXXEBTH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
- IODDQGMEFSNLGV-UHFFFAOYSA-N butane;hydrochloride Chemical compound Cl.CCCC IODDQGMEFSNLGV-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003610 charcoal 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KKVHUIDGWNOSHJ-UHFFFAOYSA-N ethanamine;propane Chemical compound CCC.CCN KKVHUIDGWNOSHJ-UHFFFAOYSA-N 0.000 description 1
- BUBWTSJXUHKBBX-UHFFFAOYSA-N ethyl acetate;sodium Chemical compound [Na].CCOC(C)=O BUBWTSJXUHKBBX-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960001269 glycine hydrochloride Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2021620A DE2021620C3 (de) | 1970-05-02 | 1970-05-02 | Neue Phenylaminoalkane und Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU440824A1 true SU440824A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-25 |
| SU440824A3 SU440824A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-25 |
Family
ID=5770113
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1649251A SU398031A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-05-02 | 1971-04-28 | |
| SU1820134A SU440824A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-05-02 | 1971-04-28 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1649251A SU398031A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-05-02 | 1971-04-28 |
Country Status (22)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2239012A1 (de) * | 1972-08-08 | 1974-02-21 | Knoll Ag | Basisch substituierte theophyllinabkoemmlinge |
| NZ210420A (en) * | 1983-12-06 | 1988-04-29 | Merrell Dow Pharma | D-amino acid oxidase substrates and pharmaceutical compositions |
| JPS6314015U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1986-07-11 | 1988-01-29 | ||
| JPS63136497A (ja) * | 1986-11-28 | 1988-06-08 | Hitachi Medical Corp | Ｘ線装置 |
| JPH0378128U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1989-11-30 | 1991-08-07 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2029385A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-01-27 | 1970-10-23 | Science Union & Cie |
-
1970
- 1970-05-02 DE DE2021620A patent/DE2021620C3/de not_active Expired
-
1971
- 1971-04-28 SU SU1649251A patent/SU398031A3/ru active
- 1971-04-28 RO RO66747A patent/RO57814A/ro unknown
- 1971-04-28 RO RO70104A patent/RO57821A/ro unknown
- 1971-04-28 SU SU1820134A patent/SU440824A3/ru active
- 1971-04-28 RO RO7100070107A patent/RO62296A/ro unknown
- 1971-04-28 RO RO70106A patent/RO57681A/ro unknown
- 1971-04-28 RO RO7100070105A patent/RO62418A/ro unknown
- 1971-04-29 CS CS2325A patent/CS175428B2/cs unknown
- 1971-04-29 CS CS3115A patent/CS170545B2/cs unknown
- 1971-04-29 CH CH29975A patent/CH579023A5/xx not_active IP Right Cessation
- 1971-04-29 CH CH632271A patent/CH561169A5/xx not_active IP Right Cessation
- 1971-04-29 YU YU1080/71A patent/YU35571B/xx unknown
- 1971-04-29 CH CH29775A patent/CH570968A5/xx not_active IP Right Cessation
- 1971-04-29 CS CS722324A patent/CS194665B2/cs unknown
- 1971-04-29 CH CH29875A patent/CH579022A5/xx not_active IP Right Cessation
- 1971-04-29 NL NLAANVRAGE7105946,A patent/NL169462C/xx not_active IP Right Cessation
- 1971-04-30 SE SE7105652A patent/SE374355B/xx unknown
- 1971-04-30 AT AT518273A patent/AT317172B/de not_active IP Right Cessation
- 1971-04-30 ES ES390778A patent/ES390778A1/es not_active Expired
- 1971-04-30 IE IE545/71A patent/IE35608B1/xx unknown
- 1971-04-30 BG BG019045A patent/BG19589A3/xx unknown
- 1971-04-30 IL IL36743A patent/IL36743A/xx unknown
- 1971-04-30 AT AT518373A patent/AT317173B/de not_active IP Right Cessation
- 1971-04-30 FR FR7115627A patent/FR2092123B1/fr not_active Expired
- 1971-04-30 ZA ZA712788A patent/ZA712788B/xx unknown
- 1971-04-30 GB GB1244371A patent/GB1354451A/en not_active Expired
- 1971-04-30 FI FI1212/71A patent/FI53571C/fi active
- 1971-04-30 AT AT375071A patent/AT317171B/de active
- 1971-04-30 BG BG22776A patent/BG21017A3/xx unknown
- 1971-04-30 BG BG019047A patent/BG19131A3/xx unknown
- 1971-04-30 AT AT518573A patent/AT317175B/de not_active IP Right Cessation
- 1971-04-30 PL PL1971177491A patent/PL91964B1/pl unknown
- 1971-04-30 PL PL1971147865A patent/PL85189B1/pl unknown
- 1971-04-30 AT AT518473A patent/AT317174B/de active
- 1971-04-30 BG BG019046A patent/BG21016A3/xx unknown
- 1971-04-30 BG BG017446A patent/BG18601A3/xx unknown
- 1971-04-30 HU HUBO1290A patent/HU162545B/hu unknown
- 1971-04-30 NO NO1615/71A patent/NO133708C/no unknown
- 1971-04-30 PL PL1971177492A patent/PL90714B1/pl unknown
- 1971-04-30 AT AT518673A patent/AT317176B/de not_active IP Right Cessation
- 1971-05-01 JP JP46029370A patent/JPS5750773B1/ja active Pending
- 1971-05-03 BE BE766654A patent/BE766654A/xx not_active IP Right Cessation
-
1972
- 1972-05-12 ES ES402638A patent/ES402638A1/es not_active Expired
- 1972-05-12 ES ES402637A patent/ES402637A1/es not_active Expired
- 1972-05-12 ES ES402636A patent/ES402636A1/es not_active Expired
-
1978
- 1978-10-26 YU YU2499/78A patent/YU36286B/xx unknown
- 1978-10-26 YU YU2498/78A patent/YU36285B/xx unknown
- 1978-10-26 YU YU02500/78A patent/YU36482B/xx unknown
-
1980
- 1980-06-16 YU YU1590/80A patent/YU37114B/xx unknown
- 1980-09-17 JP JP12902780A patent/JPS5655350A/ja active Granted
- 1980-09-17 JP JP12902980A patent/JPS5655352A/ja active Granted
- 1980-09-17 JP JP55129028A patent/JPS589090B2/ja not_active Expired
-
1981
- 1981-02-20 YU YU00433/81A patent/YU43381A/xx unknown
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