NO134058B - - Google Patents
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- Publication number
- NO134058B NO134058B NO4651/69A NO465169A NO134058B NO 134058 B NO134058 B NO 134058B NO 4651/69 A NO4651/69 A NO 4651/69A NO 465169 A NO465169 A NO 465169A NO 134058 B NO134058 B NO 134058B
- Authority
- NO
- Norway
- Prior art keywords
- dien
- compounds
- carbon atoms
- alkyl
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 6
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 230000008018 melting Effects 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 229960004132 diethyl ether Drugs 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- LDYUIVOAQFHBIO-UHFFFAOYSA-N n,n-dimethylprop-1-yn-1-amine Chemical compound CC#CN(C)C LDYUIVOAQFHBIO-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000001076 estrogenic effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000001072 progestational effect Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 101150058668 tra2 gene Proteins 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PQMRKLSVUBRLLQ-XSYGEPLQSA-N (8r,9s,13s,14s)-13-ethyl-3-methoxy-4,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C=C(OC)CC2=C1[C@H]1CC[C@](CC)(C(CC3)=O)[C@@H]3[C@@H]1CC2 PQMRKLSVUBRLLQ-XSYGEPLQSA-N 0.000 description 1
- NSUVCVKCWGOYPV-VXNCWWDNSA-N (8r,9s,13s,14s)-3-methoxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2C(CC=C(C3)OC)=C3CC[C@H]2[C@@H]2CCC(=O)[C@]21C NSUVCVKCWGOYPV-VXNCWWDNSA-N 0.000 description 1
- QARAXUHORATRQJ-UHFFFAOYSA-N 1,4-dioxane;pyridine Chemical compound C1COCCO1.C1=CC=NC=C1 QARAXUHORATRQJ-UHFFFAOYSA-N 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 208000019255 Menstrual disease Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 101100011750 Mus musculus Hsp90b1 gene Proteins 0.000 description 1
- 206010067572 Oestrogenic effect Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- NVQOFWZLYDVFMU-UHFFFAOYSA-N azane;oxolane Chemical compound N.C1CCOC1 NVQOFWZLYDVFMU-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 210000003785 decidua Anatomy 0.000 description 1
- XQKRYBXCYCKQLL-UHFFFAOYSA-N dimethylaminomethanol Chemical compound CN(C)CO XQKRYBXCYCKQLL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid 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
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 101150117196 tra-1 gene Proteins 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO742821A NO134059C (xx) | 1968-11-25 | 1974-08-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77877768A | 1968-11-25 | 1968-11-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134058B true NO134058B (xx) | 1976-05-03 |
| NO134058C NO134058C (xx) | 1976-08-11 |
Family
ID=25114361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4651/69A NO134058C (xx) | 1968-11-25 | 1969-11-24 |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS4826005B1 (xx) |
| AT (1) | AT330966B (xx) |
| BE (1) | BE742137A (xx) |
| BR (1) | BR6914427D0 (xx) |
| CA (1) | CA958005A (xx) |
| CH (3) | CH580115A5 (xx) |
| CS (5) | CS150694B2 (xx) |
| DE (1) | DE1966922A1 (xx) |
| DK (1) | DK127107B (xx) |
| ES (2) | ES387605A1 (xx) |
| FI (4) | FI47349C (xx) |
| FR (1) | FR2024166B1 (xx) |
| GB (3) | GB1297962A (xx) |
| HU (1) | HU164121B (xx) |
| NL (1) | NL149815B (xx) |
| NO (1) | NO134058C (xx) |
| PL (5) | PL82606B1 (xx) |
| SE (2) | SE369076B (xx) |
| SU (3) | SU402209A3 (xx) |
| YU (1) | YU34534B (xx) |
| ZA (1) | ZA698233B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH571537A5 (xx) * | 1970-04-24 | 1976-01-15 | Sandoz Ag | |
| CH558346A (de) * | 1971-06-17 | 1975-01-31 | Sandoz Ag | Verfahren zur herstellung neuer 3-oximino-17(alpha)-propadienyl-substituierter steroide. |
| JPS5196702U (xx) * | 1975-01-31 | 1976-08-03 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3392166A (en) * | 1966-03-30 | 1968-07-09 | Syntex Corp | Androst-4-enes and estr-4-enes having a 17alpha-diethylenically unsaturated side chain |
| US3385871A (en) * | 1965-12-15 | 1968-05-28 | Syntex Corp | Halogenated cyclopropyl and cyclopropenyl estratrienes and process for their preparation |
-
1969
- 1969-02-24 SU SU1617457A patent/SU402209A3/ru active
- 1969-11-13 CH CH208573A patent/CH580115A5/xx unknown
- 1969-11-13 CH CH1695569A patent/CH579101A5/xx not_active IP Right Cessation
- 1969-11-13 CH CH208473A patent/CH571538A5/xx not_active IP Right Cessation
- 1969-11-14 NL NL696917209A patent/NL149815B/xx not_active IP Right Cessation
- 1969-11-14 GB GB1297962D patent/GB1297962A/en not_active Expired
- 1969-11-14 GB GB1297964D patent/GB1297964A/en not_active Expired
- 1969-11-14 GB GB1297963D patent/GB1297963A/en not_active Expired
- 1969-11-20 YU YU2911/69A patent/YU34534B/xx unknown
- 1969-11-20 DK DK615769AA patent/DK127107B/da unknown
- 1969-11-21 DE DE19691966922 patent/DE1966922A1/de active Pending
- 1969-11-21 FI FI693387A patent/FI47349C/fi active
- 1969-11-24 SE SE16102/69A patent/SE369076B/xx unknown
- 1969-11-24 CS CS7196A patent/CS150694B2/cs unknown
- 1969-11-24 SE SE7301830A patent/SE378605B/xx unknown
- 1969-11-24 PL PL1969156778A patent/PL82606B1/pl unknown
- 1969-11-24 PL PL1969156783A patent/PL82690B1/pl unknown
- 1969-11-24 CS CS7194A patent/CS150692B2/cs unknown
- 1969-11-24 SU SU1615145A patent/SU390714A3/ru active
- 1969-11-24 PL PL1969156780A patent/PL82607B1/pl unknown
- 1969-11-24 NO NO4651/69A patent/NO134058C/no unknown
- 1969-11-24 CS CS7195A patent/CS150693B2/cs unknown
- 1969-11-24 CA CA068,167A patent/CA958005A/en not_active Expired
- 1969-11-24 JP JP44093688A patent/JPS4826005B1/ja active Pending
- 1969-11-24 FR FR6940364A patent/FR2024166B1/fr not_active Expired
- 1969-11-24 PL PL1969156777A patent/PL82605B1/pl unknown
- 1969-11-24 BE BE742137D patent/BE742137A/xx unknown
- 1969-11-24 PL PL1969137088A patent/PL80336B1/pl unknown
- 1969-11-24 CS CS7193A patent/CS150691B2/cs unknown
- 1969-11-24 SU SU1380086A patent/SU390715A3/ru active
- 1969-11-24 BR BR214427/69A patent/BR6914427D0/pt unknown
- 1969-11-24 AT AT1096369A patent/AT330966B/de not_active IP Right Cessation
- 1969-11-24 HU HUSA2027A patent/HU164121B/hu unknown
- 1969-11-24 CS CS7721A patent/CS150690B2/cs unknown
-
1970
- 1970-11-25 ZA ZA698233A patent/ZA698233B/xx unknown
-
1971
- 1971-01-26 ES ES0387605A patent/ES387605A1/es not_active Expired
- 1971-01-26 ES ES0387606A patent/ES387606A1/es not_active Expired
-
1972
- 1972-08-23 FI FI722331A patent/FI48347C/fi active
- 1972-08-23 FI FI722332A patent/FI47350C/fi active
-
1973
- 1973-04-18 FI FI731256A patent/FI48583C/fi active
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