SU440837A1 - - Google Patents
Info
- Publication number
- SU440837A1 SU440837A1 SU1750069A SU1750069A SU440837A1 SU 440837 A1 SU440837 A1 SU 440837A1 SU 1750069 A SU1750069 A SU 1750069A SU 1750069 A SU1750069 A SU 1750069A SU 440837 A1 SU440837 A1 SU 440837A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- oxymorphinan
- furfuryl
- yield
- compound
- hydrochloride
- Prior art date
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- -1 bicarbonates metals Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WBQMCHYYCSCXID-UHFFFAOYSA-N 3-(chloromethyl)-2-methylfuran Chemical compound CC=1OC=CC=1CCl WBQMCHYYCSCXID-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GANBJDIOIDQSGI-UHFFFAOYSA-N 2-(chloromethyl)furan Chemical compound ClCC1=CC=CO1 GANBJDIOIDQSGI-UHFFFAOYSA-N 0.000 description 2
- WECUIJXZKLGURU-UHFFFAOYSA-N 3-(chloromethyl)furan Chemical compound ClCC=1C=COC=1 WECUIJXZKLGURU-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- INAXVFBXDYWQFN-XHSDSOJGSA-N morphinan Chemical compound C1C2=CC=CC=C2[C@]23CCCC[C@H]3[C@@H]1NCC2 INAXVFBXDYWQFN-XHSDSOJGSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- SLGUAJQWZVMGFJ-CEWLAPEOSA-N (1R,9R,10R)-17-(furan-2-ylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol Chemical compound C(C1=CC=CO1)N1[C@H]2[C@@H]3CCCC[C@@]3(C=3C=C(C=CC3C2)O)CC1 SLGUAJQWZVMGFJ-CEWLAPEOSA-N 0.000 description 1
- SYBIFAOTBKJVTN-KSEOMHKRSA-N (1R,9R,10R)-17-(furan-2-ylmethyl)-4-methoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene Chemical compound C(C1=CC=CO1)N1[C@H]2[C@@H]3CCCC[C@@]3(C=3C=C(C=CC3C2)OC)CC1 SYBIFAOTBKJVTN-KSEOMHKRSA-N 0.000 description 1
- 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
- XXTMIGSYISUNAZ-UHFFFAOYSA-N 3-(chloromethyl)-2-ethylfuran Chemical compound CCC=1OC=CC=1CCl XXTMIGSYISUNAZ-UHFFFAOYSA-N 0.000 description 1
- HJYHSCTYDCMXPG-UHFFFAOYSA-N 5-(bromomethyl)furan-2-carbaldehyde Chemical compound BrCC1=CC=C(C=O)O1 HJYHSCTYDCMXPG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl 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
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- PWXMEBZOKUPCST-UHFFFAOYSA-N methyl 5-(chloromethyl)furan-2-carboxylate Chemical compound COC(=O)C1=CC=C(CCl)O1 PWXMEBZOKUPCST-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 150000003810 morphinanes Chemical class 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940051807 opiod analgesics morphinan derivative Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712107989 DE2107989A1 (de) | 1971-02-19 | 1971-02-19 | N-(Furyl-methy])-morphinane, deren Säureadditionssalze sowie Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU440837A1 true SU440837A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-25 |
| SU440837A3 SU440837A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-25 |
Family
ID=5799263
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1939073A SU481155A3 (ru) | 1971-02-19 | 1972-02-17 | Способ получени -(фурил-метил)морфинанов |
| SU1750069A SU440837A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-02-19 | 1972-02-17 | |
| SU1939076A SU466658A3 (ru) | 1971-02-19 | 1972-02-17 | Способ получени -(фурилметил) -морфинанов |
| SU1940421A SU488411A3 (ru) | 1971-02-19 | 1973-06-25 | Способ получени -(фурил-метил)морфинанов |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1939073A SU481155A3 (ru) | 1971-02-19 | 1972-02-17 | Способ получени -(фурил-метил)морфинанов |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1939076A SU466658A3 (ru) | 1971-02-19 | 1972-02-17 | Способ получени -(фурилметил) -морфинанов |
| SU1940421A SU488411A3 (ru) | 1971-02-19 | 1973-06-25 | Способ получени -(фурил-метил)морфинанов |
Country Status (25)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2229770A1 (de) * | 1972-06-19 | 1974-01-10 | Boehringer Sohn Ingelheim | N-(heteroarylmethyl)-7alpha-acyl6,14-endoaethenotetrahydro-nororipavine und -thebaine, deren hydrierungsprodukte und saeureadditionssalze sowie verfahren zu deren herstellung |
| DE2230154A1 (de) * | 1972-06-21 | 1974-01-17 | Boehringer Sohn Ingelheim | N-(heteroaryl-methyl)-6,14-endoaetheno7alpha-hydroxyalkyl-tetrahydro-nororipavine und -thebaine, deren hydrierungsprodukte und saeureadditionssalze sowie verfahren zu deren herstellung |
| DE2238839A1 (de) * | 1972-08-07 | 1974-02-14 | Boehringer Sohn Ingelheim | Neue morphinon-derivate, deren saeureadditionssalze, verfahren zu ihrer herstellung sowie ihre verwendung zur herstellung von arzneimitteln |
| US3923987A (en) * | 1972-08-07 | 1975-12-02 | Boehringer Sohn Ingelheim | Pharmaceutical compositions containing an n-furyl-or thienyl-methyl)- -oxy-7,8 -dihydro-normorphinone or norcodeinone and method of use |
| US3975368A (en) * | 1972-09-14 | 1976-08-17 | Boehringer Ingelheim Gmbh | Pharmaceutical compositions containing an N-(furyl- or thienyl-methyl)-desoxy-normorphine or norcodeine and method of use |
| DE2245141A1 (de) * | 1972-09-14 | 1974-03-21 | Boehringer Sohn Ingelheim | Neue n-(heteroarylmethyl)-desoxynormorphine und -norcodeine, deren saeureadditionssalze, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
| US4232026A (en) * | 1978-07-20 | 1980-11-04 | Merck & Co., Inc. | Diazaditwistanes, and pharmaceutical compositions for treating pain in warm blooded animals containing them |
| US7923454B2 (en) * | 2002-05-17 | 2011-04-12 | Jenken Biosciences, Inc. | Opioid and opioid-like compounds and uses thereof |
| GB0421687D0 (en) * | 2004-09-30 | 2004-11-03 | Johnson Matthey Plc | Preparation of opiate analgesics |
| GB2438399A (en) * | 2006-05-25 | 2007-11-28 | Alpharma Aps | Preparation of N-alkylated morphinans by reduction of an iminium group |
| CA2652849A1 (en) * | 2006-05-25 | 2007-12-06 | Alpharma (Bermuda) Investments Ltd. | Process useful in the preparation of morphinan antagonists |
| KR100780932B1 (ko) * | 2006-05-30 | 2007-11-30 | 엠텍비젼 주식회사 | 컬러 보간 방법 및 장치 |
| EP3294714B1 (en) * | 2015-05-08 | 2023-03-15 | Nektar Therapeutics | Morphinan derivatives for the treatment of neuropathic pain |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE573099A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-12-04 |
-
1971
- 1971-02-19 DE DE19712107989 patent/DE2107989A1/de active Pending
-
1972
- 1972-02-09 US US00224973A patent/US3793329A/en not_active Expired - Lifetime
- 1972-02-10 RO RO7200076826A patent/RO63019A/ro unknown
- 1972-02-14 PH PH13267A patent/PH10385A/en unknown
- 1972-02-16 CH CH755175A patent/CH567503A5/xx not_active IP Right Cessation
- 1972-02-16 RO RO7200076825A patent/RO63262A/ro unknown
- 1972-02-16 RO RO7200069780A patent/RO62412A/ro unknown
- 1972-02-16 RO RO7200076824A patent/RO63012A/ro unknown
- 1972-02-16 CH CH219772A patent/CH567501A5/xx not_active IP Right Cessation
- 1972-02-17 BG BG019747A patent/BG20584A3/xx unknown
- 1972-02-17 BG BG021204A patent/BG20357A3/xx unknown
- 1972-02-17 SU SU1939073A patent/SU481155A3/ru active
- 1972-02-17 CS CS3427*A patent/CS166808B2/cs unknown
- 1972-02-17 HU HUBO1351A patent/HU162947B/hu unknown
- 1972-02-17 BG BG021205A patent/BG22833A3/xx unknown
- 1972-02-17 CS CS1036A patent/CS166805B2/cs unknown
- 1972-02-17 SU SU1750069A patent/SU440837A3/ru active
- 1972-02-17 CS CS3425*A patent/CS166806B2/cs unknown
- 1972-02-17 ES ES72399875A patent/ES399875A1/es not_active Expired
- 1972-02-17 SU SU1939076A patent/SU466658A3/ru active
- 1972-02-17 BG BG021203A patent/BG20356A3/xx unknown
- 1972-02-17 CS CS3426*A patent/CS166807B2/cs unknown
- 1972-02-18 DK DK76972A patent/DK136721C/da active
- 1972-02-18 ZA ZA721072A patent/ZA721072B/xx unknown
- 1972-02-18 BE BE779582A patent/BE779582A/xx unknown
- 1972-02-18 AT AT108273A patent/AT318599B/de not_active IP Right Cessation
- 1972-02-18 FR FR7205575A patent/FR2125599B1/fr not_active Expired
- 1972-02-18 NL NL7202153A patent/NL7202153A/xx unknown
- 1972-02-18 NO NO491/72A patent/NO134055C/no unknown
- 1972-02-18 AT AT01364/72A patent/AT312588B/de active
- 1972-02-18 IL IL38788A patent/IL38788A/xx unknown
- 1972-02-18 PL PL1972153546A patent/PL77393B1/pl unknown
- 1972-02-18 DD DD160981A patent/DD96484A5/xx unknown
- 1972-02-18 CA CA135,013A patent/CA969180A/en not_active Expired
- 1972-02-18 SE SE02039/72A patent/SE363826B/xx unknown
- 1972-02-18 AT AT108373A patent/AT318600B/de not_active IP Right Cessation
- 1972-02-18 AU AU39140/72A patent/AU468490B2/en not_active Expired
- 1972-02-18 IE IE206/72A patent/IE36116B1/xx unknown
- 1972-02-18 GB GB765072A patent/GB1379781A/en not_active Expired
-
1973
- 1973-06-25 SU SU1940421A patent/SU488411A3/ru active
- 1973-11-17 ES ES420629A patent/ES420629A1/es not_active Expired
- 1973-11-17 ES ES420630A patent/ES420630A1/es not_active Expired
- 1973-11-17 ES ES420628A patent/ES420628A1/es not_active Expired
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