FI56824C - Foerfarande foer framstaellning av nya analgetiska basiska etrar - Google Patents
Foerfarande foer framstaellning av nya analgetiska basiska etrar Download PDFInfo
- Publication number
- FI56824C FI56824C FI2022/73A FI202273A FI56824C FI 56824 C FI56824 C FI 56824C FI 2022/73 A FI2022/73 A FI 2022/73A FI 202273 A FI202273 A FI 202273A FI 56824 C FI56824 C FI 56824C
- Authority
- FI
- Finland
- Prior art keywords
- diphenyl
- hydrochloride
- salts
- methoxy
- aminopropane
- Prior art date
Links
- -1 p-methoxystyryl Chemical group 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000000202 analgesic effect Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 9
- 229960005181 morphine Drugs 0.000 description 8
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 7
- 150000003840 hydrochlorides Chemical class 0.000 description 6
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IBNWKIKUJJNBKG-UHFFFAOYSA-N [methoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OC)C1=CC=CC=C1 IBNWKIKUJJNBKG-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000019788 craving Nutrition 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical class CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 description 1
- MXYGYQZXMYSNTP-UHFFFAOYSA-N 1-butoxy-4-cyclopropyl-1,1-diphenylbutan-2-amine Chemical compound C1(=CC=CC=C1)C(C(CCC1CC1)N)(OCCCC)C1=CC=CC=C1 MXYGYQZXMYSNTP-UHFFFAOYSA-N 0.000 description 1
- LWODVWRXCVHRBX-UHFFFAOYSA-N 1-butoxy-5-cyclohexylidene-1,1-diphenylpentan-2-amine Chemical compound C1(=CC=CC=C1)C(C(CCC=C1CCCCC1)N)(OCCCC)C1=CC=CC=C1 LWODVWRXCVHRBX-UHFFFAOYSA-N 0.000 description 1
- VNYJGSDKEOQUFH-UHFFFAOYSA-N 1-methoxy-2-methyl-1,1,6-triphenylhex-5-en-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)(N)CCC=CC=1C=CC=CC=1)(OC)C1=CC=CC=C1 VNYJGSDKEOQUFH-UHFFFAOYSA-N 0.000 description 1
- JSVPTUKQHLNUHR-UHFFFAOYSA-N 1-methoxy-n-methyl-1,1-diphenylhex-5-yn-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(OC)(C(CCC#C)NC)C1=CC=CC=C1 JSVPTUKQHLNUHR-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 1
- BNCLOELSTVUCSF-UHFFFAOYSA-N 3-ethoxy-3,3-diphenyl-n-(3-phenylprop-2-enyl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)CCNCC=CC1=CC=CC=C1 BNCLOELSTVUCSF-UHFFFAOYSA-N 0.000 description 1
- FJCUOCVYQKQNGU-UHFFFAOYSA-N 3-ethoxy-3,3-diphenyl-n-prop-2-ynylpropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC#C)(OCC)C1=CC=CC=C1 FJCUOCVYQKQNGU-UHFFFAOYSA-N 0.000 description 1
- HTUWRHWDXKHNSQ-UHFFFAOYSA-N 3-methoxy-3,3-diphenyl-n-(3-phenylprop-2-enyl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)CCNCC=CC1=CC=CC=C1 HTUWRHWDXKHNSQ-UHFFFAOYSA-N 0.000 description 1
- VSCPIAIKUBKNGB-UHFFFAOYSA-N 3-methoxy-3,3-diphenyl-n-prop-2-ynylpropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC#C)(OC)C1=CC=CC=C1 VSCPIAIKUBKNGB-UHFFFAOYSA-N 0.000 description 1
- GUDUNTCYADOKGJ-UHFFFAOYSA-N 4-cyclobutyl-1-methoxy-1,1-diphenylbutan-2-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)C(N)CCC1CCC1 GUDUNTCYADOKGJ-UHFFFAOYSA-N 0.000 description 1
- CUFPQHCQVPMELF-UHFFFAOYSA-N 4-cyclopropyl-1,1-diphenyl-1-propoxybutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(N)CCC1CC1 CUFPQHCQVPMELF-UHFFFAOYSA-N 0.000 description 1
- MQJVXIALIAVVQV-UHFFFAOYSA-N 4-cyclopropyl-1-ethoxy-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)C(N)CCC1CC1 MQJVXIALIAVVQV-UHFFFAOYSA-N 0.000 description 1
- AHNZCCRQIRWGPR-UHFFFAOYSA-N 4-cyclopropyl-n-methyl-1,1-diphenyl-1-propoxybutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(NC)CCC1CC1 AHNZCCRQIRWGPR-UHFFFAOYSA-N 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- PLWUKNBSCFWWBW-UHFFFAOYSA-N Cl.C=1C=CC=CC=1C(CCNCCC=CC)(OCC)C1=CC=CC=C1 Chemical compound Cl.C=1C=CC=CC=1C(CCNCCC=CC)(OCC)C1=CC=CC=C1 PLWUKNBSCFWWBW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 241001465754 Metazoa Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000220304 Prunus dulcis Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LYWASOZKZYKPQR-UHFFFAOYSA-N [ethoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OCC)C1=CC=CC=C1 LYWASOZKZYKPQR-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical compound O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- FDLVCUOMIAFXNG-UHFFFAOYSA-N methyl(propyl)azanium;chloride Chemical compound Cl.CCCNC FDLVCUOMIAFXNG-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- XJSJQANHZLQJSC-UHFFFAOYSA-N n-(3-butoxy-3,3-diphenylpropyl)but-2-en-1-amine Chemical compound C=1C=CC=CC=1C(CCNCC=CC)(OCCCC)C1=CC=CC=C1 XJSJQANHZLQJSC-UHFFFAOYSA-N 0.000 description 1
- JTQVKRXONMISDA-UHFFFAOYSA-N n-(3-ethoxy-3,3-diphenylpropyl)but-2-en-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC=CC)(OCC)C1=CC=CC=C1 JTQVKRXONMISDA-UHFFFAOYSA-N 0.000 description 1
- YFRYFWQHDBSDRV-UHFFFAOYSA-N n-(3-methoxy-3,3-diphenylpropyl)but-2-en-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC=CC)(OC)C1=CC=CC=C1 YFRYFWQHDBSDRV-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT776672A AT320615B (de) | 1972-09-11 | 1972-09-11 | Verfahren zur Herstellung von neuen basischen Äthern und von deren Säureadditionssalzen |
| AT776672 | 1972-09-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56824B FI56824B (fi) | 1979-12-31 |
| FI56824C true FI56824C (fi) | 1980-04-10 |
Family
ID=3599268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2022/73A FI56824C (fi) | 1972-09-11 | 1973-06-21 | Foerfarande foer framstaellning av nya analgetiska basiska etrar |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS523934B2 (enExample) |
| AT (1) | AT320615B (enExample) |
| CA (1) | CA986139A (enExample) |
| CH (1) | CH580568A5 (enExample) |
| CS (1) | CS164206B2 (enExample) |
| DD (1) | DD108520A1 (enExample) |
| ES (1) | ES416833A1 (enExample) |
| FI (1) | FI56824C (enExample) |
| HU (1) | HU165417B (enExample) |
| LU (1) | LU67863A1 (enExample) |
| PL (1) | PL84649B1 (enExample) |
| RO (1) | RO62911A (enExample) |
| SE (1) | SE398641B (enExample) |
| SU (1) | SU502603A3 (enExample) |
-
1972
- 1972-09-11 AT AT776672A patent/AT320615B/de not_active IP Right Cessation
-
1973
- 1973-06-21 FI FI2022/73A patent/FI56824C/fi active
- 1973-06-21 CS CS4465A patent/CS164206B2/cs unknown
- 1973-06-22 LU LU67863A patent/LU67863A1/xx unknown
- 1973-07-06 HU HUOE202A patent/HU165417B/hu unknown
- 1973-07-12 ES ES416833A patent/ES416833A1/es not_active Expired
- 1973-07-30 RO RO75652A patent/RO62911A/ro unknown
- 1973-07-30 DD DD172621A patent/DD108520A1/xx unknown
- 1973-07-31 SU SU1957935A patent/SU502603A3/ru active
- 1973-07-31 CH CH1117973A patent/CH580568A5/de not_active IP Right Cessation
- 1973-07-31 SE SE7310530A patent/SE398641B/xx unknown
- 1973-07-31 JP JP48085549A patent/JPS523934B2/ja not_active Expired
- 1973-09-06 CA CA180,423A patent/CA986139A/en not_active Expired
- 1973-09-11 PL PL1973165148A patent/PL84649B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO62911A (enExample) | 1977-08-15 |
| AT320615B (de) | 1975-02-25 |
| LU67863A1 (enExample) | 1973-08-30 |
| CS164206B2 (enExample) | 1975-11-07 |
| SU502603A3 (ru) | 1976-02-05 |
| JPS523934B2 (enExample) | 1977-01-31 |
| FI56824B (fi) | 1979-12-31 |
| ES416833A1 (es) | 1976-02-16 |
| CA986139A (en) | 1976-03-23 |
| JPS4980050A (enExample) | 1974-08-02 |
| PL84649B1 (en) | 1976-04-30 |
| DD108520A1 (enExample) | 1974-09-20 |
| HU165417B (enExample) | 1974-08-28 |
| SE398641B (sv) | 1978-01-09 |
| CH580568A5 (en) | 1976-10-15 |
| SE7310530L (enExample) | 1974-03-12 |
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