DE2063406C3 - Acylderivate des Proscillaridin A, Verfahren zu deren Herstellung und diese enthaltende Präparate - Google Patents
Acylderivate des Proscillaridin A, Verfahren zu deren Herstellung und diese enthaltende PräparateInfo
- Publication number
- DE2063406C3 DE2063406C3 DE2063406A DE2063406A DE2063406C3 DE 2063406 C3 DE2063406 C3 DE 2063406C3 DE 2063406 A DE2063406 A DE 2063406A DE 2063406 A DE2063406 A DE 2063406A DE 2063406 C3 DE2063406 C3 DE 2063406C3
- Authority
- DE
- Germany
- Prior art keywords
- proscillaridin
- acid
- general formula
- preparation
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229960003584 proscillaridin Drugs 0.000 title description 40
- MYEJFUXQJGHEQK-UHFFFAOYSA-N proscillaridin A Natural products OC1C(O)C(O)C(C)OC1OC1C=C2CCC3C4(O)CCC(C5=COC(=O)C=C5)C4(C)CCC3C2(C)CC1 MYEJFUXQJGHEQK-UHFFFAOYSA-N 0.000 title description 34
- 238000000034 method Methods 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 4
- 125000002252 acyl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 9
- MYEJFUXQJGHEQK-ALRJYLEOSA-N Proscillaridin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C=C2CC[C@H]3[C@@]4(O)CC[C@H](C5=COC(=O)C=C5)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 MYEJFUXQJGHEQK-ALRJYLEOSA-N 0.000 description 30
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- -1 cyclic orthoester Chemical class 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000829 suppository Substances 0.000 description 10
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- 239000002253 acid Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 8
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- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- ZGMNAIODRDOMEK-UHFFFAOYSA-N 1,1,1-trimethoxypropane Chemical compound CCC(OC)(OC)OC ZGMNAIODRDOMEK-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- GZGZWHKGQNQJDW-UHFFFAOYSA-L C(CCCCCCCCCCCCCCCCC)(=O)[O-].[Mg+2].N1C(CCC1)=O.C(CCCCCCCCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)[O-].[Mg+2].N1C(CCC1)=O.C(CCCCCCCCCCCCCCCCC)(=O)[O-] GZGZWHKGQNQJDW-UHFFFAOYSA-L 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
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- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
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- 239000011975 tartaric acid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 238000001665 trituration Methods 0.000 description 2
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- KOPMZTKUZCNGFY-UHFFFAOYSA-N 1,1,1-triethoxybutane Chemical compound CCCC(OCC)(OCC)OCC KOPMZTKUZCNGFY-UHFFFAOYSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- 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
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- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
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- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical group COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
- A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/2853—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers, poly(lactide-co-glycolide)
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2063406A DE2063406C3 (de) | 1970-12-23 | 1970-12-23 | Acylderivate des Proscillaridin A, Verfahren zu deren Herstellung und diese enthaltende Präparate |
| BG019278A BG20580A3 (bg) | 1970-12-23 | 1971-12-18 | Метод за получаване на ацилови производни на просциларидин а |
| JP46103559A JPS5741480B1 (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-20 | |
| CH1859471A CH593302A5 (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-20 | |
| SU1728032A SU420173A3 (ru) | 1970-12-23 | 1971-12-21 | Способ получения ацилпроизводнб1х просцилларидина а |
| ES398208A ES398208A1 (es) | 1970-12-23 | 1971-12-21 | Procedimiento para la preparacion de nuevos derivados aci- licos de la proscilaridina. |
| HUBO1338A HU162742B (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-21 | |
| CA130,806A CA939664A (en) | 1970-12-23 | 1971-12-22 | Acyl derivatives of the proscillaridine a and process of the production thereof |
| AT1103471A AT312815B (de) | 1970-12-23 | 1971-12-22 | Verfahren zur Herstellung von neuen Acylderivaten des Proscillaridins A |
| IL38430A IL38430A (en) | 1970-12-23 | 1971-12-22 | Acyl derivatives of proscillaridine a,their preparation and pharmaceutical compositions containing them |
| FI713661A FI50248C (fi) | 1970-12-23 | 1971-12-22 | Menetelmä uusien proskillaridiini A asyylijohdannaisten valmistamiseks i. |
| AU37197/71A AU469336B2 (en) | 1970-12-23 | 1971-12-22 | Novel acyl analogues of proscillaridin a |
| YU3224/71A YU35150B (en) | 1970-12-23 | 1971-12-22 | Process for preparing novel acyl derivatives of proscillaridin a |
| NL7117645A NL7117645A (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-22 | |
| SE7116530A SE380812B (sv) | 1970-12-23 | 1971-12-22 | Forfarande for framstellning av nya acylderivat av proscillaridin a |
| NO4779/71A NO136671C (no) | 1970-12-23 | 1971-12-22 | Analogifremgangsm}te for fremstilling av terapeutisk aktive 2`-acylderivater av proscillaridin |
| GB5972671A GB1374079A (en) | 1970-12-23 | 1971-12-22 | Analogues of proscillaridin |
| DK628671AA DK129654B (da) | 1970-12-23 | 1971-12-22 | Analogifremgangsmåde til fremstilling af 2'-acylderivater af proscillaridin A. |
| RO69152A RO59396A (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-22 | |
| DD159823A DD95231A5 (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-22 | |
| CS8920A CS166041B2 (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-22 | |
| PL1971152413A PL83079B1 (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-22 | |
| BE777164A BE777164A (fr) | 1970-12-23 | 1971-12-22 | Nouveaux derives acyles de la proscillaridine a et procede pourles fabriquer |
| ZA718589A ZA718589B (en) | 1970-12-23 | 1971-12-22 | Improvements relating to acyl derivatives of proscillaridi ne a |
| FR7146346A FR2119045B1 (enrdf_load_stackoverflow) | 1970-12-23 | 1971-12-23 | |
| IE1638/71A IE36110B1 (en) | 1970-12-23 | 1971-12-23 | Analogues of proscillaridin a |
| US05/421,751 US3987031A (en) | 1970-12-23 | 1973-12-05 | Acyl derivatives of proscillaridin a |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2063406A DE2063406C3 (de) | 1970-12-23 | 1970-12-23 | Acylderivate des Proscillaridin A, Verfahren zu deren Herstellung und diese enthaltende Präparate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2063406A1 DE2063406A1 (de) | 1972-09-21 |
| DE2063406B2 DE2063406B2 (de) | 1977-08-25 |
| DE2063406C3 true DE2063406C3 (de) | 1978-05-03 |
Family
ID=5791955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2063406A Expired DE2063406C3 (de) | 1970-12-23 | 1970-12-23 | Acylderivate des Proscillaridin A, Verfahren zu deren Herstellung und diese enthaltende Präparate |
Country Status (26)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2427976C2 (de) * | 1974-06-10 | 1985-12-12 | Knoll Ag, 6700 Ludwigshafen | Proscillaridinäther, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU33975B (en) * | 1969-01-09 | 1978-09-08 | Knol Ag Chemische Fabriken | Process for preparing bufatrienolide-rhamnoside-acylates |
| DE1910207C3 (de) * | 1969-02-28 | 1978-04-13 | Knoll Ag, 6700 Ludwigshafen | Verfahren zu deren Herstellung |
| RO60624A (enrdf_load_stackoverflow) * | 1970-03-05 | 1976-07-15 | ||
| JPS512471A (ja) * | 1974-06-25 | 1976-01-10 | Yasushi Maeda | Shootoringutokoiruno toritsukeho |
| JPS526988A (en) * | 1975-07-04 | 1977-01-19 | Sumitomo Electric Ind Ltd | Insulated wire |
-
1970
- 1970-12-23 DE DE2063406A patent/DE2063406C3/de not_active Expired
-
1971
- 1971-12-18 BG BG019278A patent/BG20580A3/xx unknown
- 1971-12-20 CH CH1859471A patent/CH593302A5/xx not_active IP Right Cessation
- 1971-12-20 JP JP46103559A patent/JPS5741480B1/ja active Pending
- 1971-12-21 SU SU1728032A patent/SU420173A3/ru active
- 1971-12-21 ES ES398208A patent/ES398208A1/es not_active Expired
- 1971-12-21 HU HUBO1338A patent/HU162742B/hu unknown
- 1971-12-22 IL IL38430A patent/IL38430A/xx unknown
- 1971-12-22 FI FI713661A patent/FI50248C/fi active
- 1971-12-22 GB GB5972671A patent/GB1374079A/en not_active Expired
- 1971-12-22 AT AT1103471A patent/AT312815B/de not_active IP Right Cessation
- 1971-12-22 AU AU37197/71A patent/AU469336B2/en not_active Expired
- 1971-12-22 YU YU3224/71A patent/YU35150B/xx unknown
- 1971-12-22 BE BE777164A patent/BE777164A/xx unknown
- 1971-12-22 NL NL7117645A patent/NL7117645A/xx not_active Application Discontinuation
- 1971-12-22 SE SE7116530A patent/SE380812B/xx unknown
- 1971-12-22 DK DK628671AA patent/DK129654B/da not_active IP Right Cessation
- 1971-12-22 CS CS8920A patent/CS166041B2/cs unknown
- 1971-12-22 RO RO69152A patent/RO59396A/ro unknown
- 1971-12-22 NO NO4779/71A patent/NO136671C/no unknown
- 1971-12-22 PL PL1971152413A patent/PL83079B1/pl unknown
- 1971-12-22 CA CA130,806A patent/CA939664A/en not_active Expired
- 1971-12-22 DD DD159823A patent/DD95231A5/xx unknown
- 1971-12-22 ZA ZA718589A patent/ZA718589B/xx unknown
- 1971-12-23 FR FR7146346A patent/FR2119045B1/fr not_active Expired
- 1971-12-23 IE IE1638/71A patent/IE36110B1/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee | ||
| EI | Miscellaneous see part 3 | ||
| EILA | Invalidation of the cancellation of the patent | ||
| EGA | New person/name/address of the applicant | ||
| 8339 | Ceased/non-payment of the annual fee |