HU180927B - Process for producing 1k-hydroximino-e-homoe-eburane de rivatives - Google Patents
Process for producing 1k-hydroximino-e-homoe-eburane de rivatives Download PDFInfo
- Publication number
- HU180927B HU180927B HU79RI719A HURI000719A HU180927B HU 180927 B HU180927 B HU 180927B HU 79RI719 A HU79RI719 A HU 79RI719A HU RI000719 A HURI000719 A HU RI000719A HU 180927 B HU180927 B HU 180927B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compounds
- acid
- iii
- homoeburnane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- 239000002253 acid Chemical group 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- -1 alkali metal nitrite Chemical class 0.000 claims description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 230000002140 halogenating effect Effects 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- WYIJGAVIVKPUGJ-GIVPXCGWSA-N brovincamine Chemical compound BrC1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 WYIJGAVIVKPUGJ-GIVPXCGWSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229950006936 apovincamine Drugs 0.000 description 1
- OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229950002641 brovincamine Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QDXITYMFYDFULW-UHFFFAOYSA-N methyl 2-(2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-yl)propanoate Chemical class C1CCCC2C(C(C)C(=O)OC)CCCN21 QDXITYMFYDFULW-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229960002726 vincamine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79RI719A HU180927B (en) | 1979-07-13 | 1979-07-13 | Process for producing 1k-hydroximino-e-homoe-eburane de rivatives |
| IL60445A IL60445A (en) | 1979-07-13 | 1980-06-30 | Process for the preparation of dextrorotatory hydroxyimino 14-oxo-e-homo-eburnane derivatives and the novel dextrorotatory 15-halo-14-oxo-e-homoeburnane intermediates therefor |
| ZA00803952A ZA803952B (en) | 1979-07-13 | 1980-07-01 | A process for the preparation of 15-hydroxyimino-e-homoeburnane derivatives |
| NL8003822A NL8003822A (nl) | 1979-07-13 | 1980-07-02 | Werkwijze voor de bereiding van eburnaanderivaten. |
| FI802175A FI70020C (fi) | 1979-07-13 | 1980-07-07 | Som mellanprodukter vid framstaellning av 15-hydroxi-imino-e-homoeburnanderivat anvaendbara 15-halogen-e-homoeburnanderivat foerfarande foer deras framstaellning och deras anvaendning |
| BE1/9892A BE884228A (fr) | 1979-07-13 | 1980-07-09 | Procede de preparation de derives de 15-hydroxyimino-e-homoeburnane et composes obtenus par ce procede |
| PH24262A PH15654A (en) | 1979-07-13 | 1980-07-09 | A process for the preparation of 15-hydroxyimino-e-homoeburnane derivatives |
| FR8015361A FR2460951A1 (fr) | 1979-07-13 | 1980-07-10 | Procede de preparation de derives de 15-hydroxyimino-e-homoeburnane et composes obtenus par ce procede |
| AT0358880A AT375939B (de) | 1979-07-13 | 1980-07-10 | Verfahren zur herstellung von neuen 15-halogen-e- homoeburnanderivaten, von deren saeureadditions- salzen, epimeren und optischen antipoden |
| GB8022561A GB2055368B (en) | 1979-07-13 | 1980-07-10 | E-homoeburnane derivatives |
| NZ194316A NZ194316A (en) | 1979-07-13 | 1980-07-11 | Preparation of 15-hydroxyimino-e-homoeburnane derivatives and 15-halo-e-homoeburnane precursors therein |
| MX10160580U MX6565E (es) | 1979-07-13 | 1980-07-11 | Procedimiento para preparar derivados de 15-hidroxiimino-e-homoeburnano |
| IT23404/80A IT1132528B (it) | 1979-07-13 | 1980-07-11 | Procedimento per la preparazione di derivati del 15-idrossiimmino-e-omoeburano |
| SE8005127A SE438504B (sv) | 1979-07-13 | 1980-07-11 | 15-halogen-e-homoeburnanderivat och forfarande for deras framstellning |
| SU802949854A SU982541A3 (ru) | 1979-07-13 | 1980-07-11 | Способ получени производных 15-оксиимино-е-гомоэбурнана или их солей или их оптических изомеров и производных промежуточного 15-хлор-е-гомоэбурнана или их солей или их оптических изомеров |
| DK302280A DK156574C (da) | 1979-07-13 | 1980-07-11 | Fremgangsmaade til fremstilling af et racemisk eller optisk aktivt 15-hydroxyimino-e-homoeburnanderivat eller syreadditionssalte deraf |
| AU60350/80A AU534308B2 (en) | 1979-07-13 | 1980-07-11 | 15-hydroxyimino-e-homo-eburnane derivatives |
| CA000355991A CA1137083A (en) | 1979-07-13 | 1980-07-11 | Process for the preparation of 15- hiydroxyimino-homoeburnane derivatives |
| ES493336A ES8106727A1 (es) | 1979-07-13 | 1980-07-11 | Procedimiento de preparacion de derivados 15-hidroxiimino-e-homoeburnanos,de sus sales de adicion acidas y de sus deri- vados opticamente activos |
| NO802101A NO802101L (no) | 1979-07-13 | 1980-07-11 | Fremgangsmaate ved fremstilling av 15-hydroxyimino-e-homo-eburnanderivater. |
| CH534080A CH644122A5 (de) | 1979-07-13 | 1980-07-11 | 14-oxo-15-halogen-e-homoeburnanderivate, verfahren zu deren herstellung und deren verwendung. |
| JP55094575A JPS595595B2 (ja) | 1979-07-13 | 1980-07-12 | １５−ヒドロキシイミノ−ｅ−ホモエブルナン誘導体の製造方法 |
| US06/168,560 US4314939A (en) | 1979-07-13 | 1980-07-14 | Process for the preparation of 15-hydroxyimino-E-homoeburnane and intermediates therefor |
| DE19803026602 DE3026602A1 (de) | 1979-07-13 | 1980-07-14 | 14-oxo-15-halogen-e-homoeburnanderivate, verfahren zur herstellung derselben und von 14-oxo-15-hydroxyimino-e-homoeburnanderivaten und die ersteren enthaltende arzneimittel |
| JP58120151A JPS59116285A (ja) | 1979-07-13 | 1983-07-01 | １５−ハロ−ｅ−ホモエブルナン誘導体およびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79RI719A HU180927B (en) | 1979-07-13 | 1979-07-13 | Process for producing 1k-hydroximino-e-homoe-eburane de rivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180927B true HU180927B (en) | 1983-05-30 |
Family
ID=11001102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79RI719A HU180927B (en) | 1979-07-13 | 1979-07-13 | Process for producing 1k-hydroximino-e-homoe-eburane de rivatives |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4314939A (en, 2012) |
| JP (2) | JPS595595B2 (en, 2012) |
| AT (1) | AT375939B (en, 2012) |
| AU (1) | AU534308B2 (en, 2012) |
| BE (1) | BE884228A (en, 2012) |
| CA (1) | CA1137083A (en, 2012) |
| CH (1) | CH644122A5 (en, 2012) |
| DE (1) | DE3026602A1 (en, 2012) |
| DK (1) | DK156574C (en, 2012) |
| ES (1) | ES8106727A1 (en, 2012) |
| FI (1) | FI70020C (en, 2012) |
| FR (1) | FR2460951A1 (en, 2012) |
| GB (1) | GB2055368B (en, 2012) |
| HU (1) | HU180927B (en, 2012) |
| IL (1) | IL60445A (en, 2012) |
| IT (1) | IT1132528B (en, 2012) |
| NL (1) | NL8003822A (en, 2012) |
| NO (1) | NO802101L (en, 2012) |
| NZ (1) | NZ194316A (en, 2012) |
| PH (1) | PH15654A (en, 2012) |
| SE (1) | SE438504B (en, 2012) |
| SU (1) | SU982541A3 (en, 2012) |
| ZA (1) | ZA803952B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU181496B (en) * | 1979-08-13 | 1983-07-28 | Richter Gedeon Vegyeszet | Process for preparing 10-bromo-15-hydroxy-e-homo-eburnanes |
| HU182411B (en) * | 1981-11-03 | 1984-01-30 | Richter Gedeon Vegyeszet | Process for preparing eburnamonine derivatives |
| HU186891B (en) * | 1981-06-12 | 1985-10-28 | Richter Gedeon Vegyeszet | Process for producing esters of apovincaminic acid |
| HU182380B (en) * | 1981-09-30 | 1983-12-28 | Richter Gedeon Vegyeszet | Process for producing esters of vincaminic acid |
| HU185172B (en) * | 1981-12-30 | 1984-12-28 | Richter Gedeon Vegyeszet | Process for the preparation of hydroxy-imino-e-homo-eburnanes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU180514B (hu) * | 1977-05-26 | 1983-03-28 | Richter Gedeon Vegyeszet | Eljárás apovinkaminsav-észterek, illetve vinkaminsav-észterek és apovinkaminsavészterek egyidejű előállítására |
| HU180928B (en) * | 1979-08-06 | 1983-05-30 | Richter Gedeon Vegyeszet | Process for preparing new brominated 15-hydroxy-e-homo-eburane derivatives |
| HU181496B (en) * | 1979-08-13 | 1983-07-28 | Richter Gedeon Vegyeszet | Process for preparing 10-bromo-15-hydroxy-e-homo-eburnanes |
-
1979
- 1979-07-13 HU HU79RI719A patent/HU180927B/hu not_active IP Right Cessation
-
1980
- 1980-06-30 IL IL60445A patent/IL60445A/xx unknown
- 1980-07-01 ZA ZA00803952A patent/ZA803952B/xx unknown
- 1980-07-02 NL NL8003822A patent/NL8003822A/nl not_active Application Discontinuation
- 1980-07-07 FI FI802175A patent/FI70020C/fi not_active IP Right Cessation
- 1980-07-09 BE BE1/9892A patent/BE884228A/fr not_active IP Right Cessation
- 1980-07-09 PH PH24262A patent/PH15654A/en unknown
- 1980-07-10 FR FR8015361A patent/FR2460951A1/fr active Granted
- 1980-07-10 AT AT0358880A patent/AT375939B/de not_active IP Right Cessation
- 1980-07-10 GB GB8022561A patent/GB2055368B/en not_active Expired
- 1980-07-11 ES ES493336A patent/ES8106727A1/es not_active Expired
- 1980-07-11 SU SU802949854A patent/SU982541A3/ru active
- 1980-07-11 SE SE8005127A patent/SE438504B/sv not_active IP Right Cessation
- 1980-07-11 IT IT23404/80A patent/IT1132528B/it active
- 1980-07-11 AU AU60350/80A patent/AU534308B2/en not_active Ceased
- 1980-07-11 DK DK302280A patent/DK156574C/da not_active IP Right Cessation
- 1980-07-11 CA CA000355991A patent/CA1137083A/en not_active Expired
- 1980-07-11 CH CH534080A patent/CH644122A5/de not_active IP Right Cessation
- 1980-07-11 NZ NZ194316A patent/NZ194316A/xx unknown
- 1980-07-11 NO NO802101A patent/NO802101L/no unknown
- 1980-07-12 JP JP55094575A patent/JPS595595B2/ja not_active Expired
- 1980-07-14 US US06/168,560 patent/US4314939A/en not_active Expired - Lifetime
- 1980-07-14 DE DE19803026602 patent/DE3026602A1/de active Granted
-
1983
- 1983-07-01 JP JP58120151A patent/JPS59116285A/ja active Granted
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