CA1122589A - Process for obtaining natural terpenes having an antipsoriatic activity - Google Patents
Process for obtaining natural terpenes having an antipsoriatic activityInfo
- Publication number
- CA1122589A CA1122589A CA314,254A CA314254A CA1122589A CA 1122589 A CA1122589 A CA 1122589A CA 314254 A CA314254 A CA 314254A CA 1122589 A CA1122589 A CA 1122589A
- Authority
- CA
- Canada
- Prior art keywords
- polypodium
- rhyzomes
- hexane
- ethanol
- solvent
- 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
- 238000000034 method Methods 0.000 title claims abstract description 12
- 230000008569 process Effects 0.000 title claims abstract description 8
- 150000003505 terpenes Chemical class 0.000 title claims abstract description 8
- 235000007586 terpenes Nutrition 0.000 title claims abstract description 8
- 230000002682 anti-psoriatic effect Effects 0.000 title claims abstract description 7
- 238000001704 evaporation Methods 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 239000002245 particle Substances 0.000 claims abstract description 4
- 241000723185 Cyathea Species 0.000 claims abstract description 3
- 241001624848 Phlebodium Species 0.000 claims abstract description 3
- 241001625037 Phlebodium aureum Species 0.000 claims abstract description 3
- 241000487005 Phlebodium decumanum Species 0.000 claims abstract description 3
- 241001362840 Serpocaulon triseriale Species 0.000 claims abstract description 3
- 229940075984 polypodium leucotomos Drugs 0.000 claims abstract description 3
- 241000393483 Dryopteris crassirhizoma Species 0.000 claims abstract 2
- 241001518143 Polypodium <fern> Species 0.000 claims abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000001117 sulphuric acid Substances 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims 2
- 230000003472 neutralizing effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- ZHDRLFGZQZCZKX-BQOUFORSSA-N Fernene Chemical compound CC1(C)CCC[C@]2(C)C3=CC[C@@]4(C)[C@@H]5CC[C@H](C(C)C)[C@@]5(C)CC[C@]4(C)[C@H]3CC[C@H]21 ZHDRLFGZQZCZKX-BQOUFORSSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 201000004681 Psoriasis Diseases 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 230000001185 psoriatic effect Effects 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 235000013681 dietary sucrose Nutrition 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 229960004793 sucrose Drugs 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000002068 genetic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241001061225 Arcos Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196133 Dryopteris Species 0.000 description 1
- 101100126176 Escherichia coli (strain K12) intQ gene Proteins 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000985694 Polypodiopsida Species 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000001974 anti-anabolic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000002347 carcinogenetic effect Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000001033 granulometry Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 206010033898 parapsoriasis Diseases 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000005084 renal tissue Anatomy 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 125000002345 steroid group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/11—Pteridophyta or Filicophyta (ferns)
- A61K36/12—Filicopsida or Pteridopsida
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Mycology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES470204A ES470204A1 (es) | 1978-05-24 | 1978-05-24 | Procedimiento de obtencion de terpenos naturales con activi-dad antipsoriatica |
| ES470,204 | 1978-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1122589A true CA1122589A (en) | 1982-04-27 |
Family
ID=8476164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA314,254A Expired CA1122589A (en) | 1978-05-24 | 1978-10-25 | Process for obtaining natural terpenes having an antipsoriatic activity |
Country Status (34)
| Country | Link |
|---|---|
| JP (1) | JPS59486B2 (cs) |
| AR (1) | AR226999A1 (cs) |
| AT (1) | AT366260B (cs) |
| AU (1) | AU529300B2 (cs) |
| BE (1) | BE872718A (cs) |
| BG (1) | BG34449A3 (cs) |
| CA (1) | CA1122589A (cs) |
| CH (1) | CH642039A5 (cs) |
| CS (1) | CS223879B2 (cs) |
| CU (1) | CU35086A (cs) |
| DE (1) | DE2847836C3 (cs) |
| DK (1) | DK211879A (cs) |
| EG (1) | EG14353A (cs) |
| ES (1) | ES470204A1 (cs) |
| FI (1) | FI64892C (cs) |
| FR (1) | FR2426471A1 (cs) |
| GB (1) | GB2022094B (cs) |
| GR (1) | GR65351B (cs) |
| HU (1) | HU180710B (cs) |
| IE (1) | IE48415B1 (cs) |
| IL (1) | IL57377A (cs) |
| IT (1) | IT7919644A0 (cs) |
| LU (1) | LU81315A1 (cs) |
| MA (1) | MA18443A1 (cs) |
| MX (1) | MX5537E (cs) |
| NL (1) | NL7904063A (cs) |
| NO (1) | NO791704L (cs) |
| NZ (1) | NZ190535A (cs) |
| PL (1) | PL126926B1 (cs) |
| PT (1) | PT68719A (cs) |
| SE (1) | SE7903761L (cs) |
| SU (1) | SU995700A3 (cs) |
| YU (1) | YU121579A (cs) |
| ZA (1) | ZA792540B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES490293A0 (es) * | 1980-04-02 | 1981-04-16 | Conrad Ltd | Un procedimiento de obtencion de un extracto de las fraccio-nes polares de los helechos de la familia polypodiaceae. |
| EP0503208A1 (en) * | 1991-03-08 | 1992-09-16 | Maracuyama International, S.A. | Procedure for obtaining a natural water-soluble extract from the leaves and/or rhizomes of various immunologically active ferns |
| ES2088770B1 (es) * | 1995-02-23 | 1997-03-16 | Esp Farmaceuticas Centrum Sa | Una composicion farmaceutica con actividad en el tratamiento de disfunciones cognitivas y/o neuroinmunes. |
| PT680762E (pt) * | 1994-05-06 | 2002-12-31 | Esp Farmaceuticas Centrum Sa | Composicao farmaceutica compreendendo extracto(s) de feito para tratamento de disfuncoes neurodegenerativas |
| ES2068163B1 (es) * | 1994-05-06 | 1995-09-01 | Esp Farmaceuticas Centrum Sa | Procedimiento de obtencion de un extracto vegetal con actividad en el tratamiento de disfunciones cognitivas y/o neuroinmunes. |
| RU2124363C1 (ru) * | 1996-08-23 | 1999-01-10 | Общество с ограниченной ответственностью "Сибирский богатырь" | Способ лечения дерматологических заболеваний |
| US6228366B1 (en) * | 1998-07-29 | 2001-05-08 | Helsint, S.A.L. | Water-soluble fractions of Phlebodium decumanum and its use as nutritional supplement in AIDS and cancer patients |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3395223A (en) * | 1965-05-13 | 1968-07-30 | Carter Wallace | Fern extract for treating gastric ulcers |
| JPS5464871A (en) * | 1977-10-31 | 1979-05-25 | Nippon Electric Co | Device for firing discharge lamp |
| ES471572A1 (es) * | 1978-07-07 | 1979-01-16 | Conrad Ltd | Procedimiento de obtencion de fraccion polar natural con ac-tividad antipsoriatica |
-
1978
- 1978-05-24 ES ES470204A patent/ES470204A1/es not_active Expired
- 1978-10-11 AR AR274039A patent/AR226999A1/es active
- 1978-10-12 GR GR57430A patent/GR65351B/el unknown
- 1978-10-25 CA CA314,254A patent/CA1122589A/en not_active Expired
- 1978-10-30 PT PT68719A patent/PT68719A/pt unknown
- 1978-11-03 DE DE2847836A patent/DE2847836C3/de not_active Expired
- 1978-12-13 BE BE192279A patent/BE872718A/xx not_active IP Right Cessation
-
1979
- 1979-01-26 IT IT7919644A patent/IT7919644A0/it unknown
- 1979-04-05 MX MX797853U patent/MX5537E/es unknown
- 1979-04-27 SE SE7903761A patent/SE7903761L/xx not_active Application Discontinuation
- 1979-05-21 MA MA18637A patent/MA18443A1/fr unknown
- 1979-05-22 EG EG309/79A patent/EG14353A/xx active
- 1979-05-22 AT AT0375279A patent/AT366260B/de not_active IP Right Cessation
- 1979-05-22 CH CH477679A patent/CH642039A5/de not_active IP Right Cessation
- 1979-05-22 FI FI791616A patent/FI64892C/fi not_active IP Right Cessation
- 1979-05-23 NL NL7904063A patent/NL7904063A/xx not_active Application Discontinuation
- 1979-05-23 NO NO791704A patent/NO791704L/no unknown
- 1979-05-23 PL PL1979215804A patent/PL126926B1/pl unknown
- 1979-05-23 FR FR7913216A patent/FR2426471A1/fr active Granted
- 1979-05-23 DK DK211879A patent/DK211879A/da not_active Application Discontinuation
- 1979-05-23 CU CU7935086A patent/CU35086A/es unknown
- 1979-05-23 IL IL57377A patent/IL57377A/xx unknown
- 1979-05-23 ZA ZA792540A patent/ZA792540B/xx unknown
- 1979-05-23 YU YU01215/79A patent/YU121579A/xx unknown
- 1979-05-23 HU HU79CO370A patent/HU180710B/hu unknown
- 1979-05-23 NZ NZ190535A patent/NZ190535A/xx unknown
- 1979-05-23 LU LU81315A patent/LU81315A1/xx unknown
- 1979-05-23 CS CS793543A patent/CS223879B2/cs unknown
- 1979-05-23 BG BG043706A patent/BG34449A3/xx unknown
- 1979-05-23 SU SU792771805A patent/SU995700A3/ru active
- 1979-05-24 AU AU47381/79A patent/AU529300B2/en not_active Ceased
- 1979-05-24 GB GB7918175A patent/GB2022094B/en not_active Expired
- 1979-05-24 JP JP54064870A patent/JPS59486B2/ja not_active Expired
- 1979-08-08 IE IE974/79A patent/IE48415B1/en unknown
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