CA1063942A - Isolation of utero-evacuant substances from plant extracts - Google Patents
Isolation of utero-evacuant substances from plant extractsInfo
- Publication number
- CA1063942A CA1063942A CA264,053A CA264053A CA1063942A CA 1063942 A CA1063942 A CA 1063942A CA 264053 A CA264053 A CA 264053A CA 1063942 A CA1063942 A CA 1063942A
- Authority
- CA
- Canada
- Prior art keywords
- utero
- silicic acid
- mixture
- evacuant
- silver nitrate
- 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
- 239000000126 substance Substances 0.000 title abstract description 7
- 238000002955 isolation Methods 0.000 title abstract 3
- 239000000419 plant extract Substances 0.000 title abstract 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 22
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 17
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910001961 silver nitrate Inorganic materials 0.000 claims abstract description 15
- XRDHAXIOHKTIGF-UKHUEATNSA-N 9-[(2r,3s,6e)-3-hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2-yl]-2,6-dimethylnon-2-en-5-one Chemical compound CC(C)=CCC(=O)C(C)CCC[C@@]1(C)OC\C(=C\CO)CC[C@@H]1O XRDHAXIOHKTIGF-UKHUEATNSA-N 0.000 claims abstract description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 241000196324 Embryophyta Species 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 241000401894 Montanoa tomentosa Species 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 241000396685 Montanoa Species 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 238000004587 chromatography analysis Methods 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 210000004291 uterus Anatomy 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000035935 pregnancy Effects 0.000 description 6
- 244000269722 Thea sinensis Species 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 235000013616 tea Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000013014 purified material Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- -1 aliphatic ketones Chemical class 0.000 description 3
- 239000000287 crude extract Substances 0.000 description 3
- 210000003101 oviduct Anatomy 0.000 description 3
- 229960003387 progesterone Drugs 0.000 description 3
- 239000000186 progesterone Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 101000722960 Onchocerca volvulus Onchocystatin Proteins 0.000 description 2
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 2
- 206010000210 abortion Diseases 0.000 description 2
- 231100000176 abortion Toxicity 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000000411 inducer Substances 0.000 description 2
- 210000004914 menses Anatomy 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- FXKCXGBBUBCRPU-GBOPCIDUSA-N 2-[(2r,4ar,8s,8ar)-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid Chemical compound C1C[C@@H](C(=C)C(O)=O)C[C@H]2[C@@](C)(O)CCC[C@@]21C FXKCXGBBUBCRPU-GBOPCIDUSA-N 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- QNVBIDULDLPCDQ-UHFFFAOYSA-N Ilicic acid Natural products CC1(O)CCC2(C)CCC(CC2C1)C(=C)C(=O)O QNVBIDULDLPCDQ-UHFFFAOYSA-N 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- WGXZDYPGLJYBJW-UHFFFAOYSA-N chloroform;propan-2-ol Chemical compound CC(C)O.ClC(Cl)Cl WGXZDYPGLJYBJW-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000027326 copulation Effects 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 235000019225 fermented tea Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002175 menstrual effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- NYEXKMXIZZHAKQ-UHFFFAOYSA-N silver;silicic acid;nitrate Chemical compound [Ag+].[O-][N+]([O-])=O.O[Si](O)(O)O NYEXKMXIZZHAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
-
- 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
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/282—Porous sorbents
- B01J20/283—Porous sorbents based on silica
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3234—Inorganic material layers
- B01J20/3236—Inorganic material layers containing metal, other than zeolites, e.g. oxides, hydroxides, sulphides or salts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Biotechnology (AREA)
- Inorganic Chemistry (AREA)
- Medical Informatics (AREA)
- Botany (AREA)
- Alternative & Traditional Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/632,552 US3986952A (en) | 1975-11-17 | 1975-11-17 | Isolation of utero-evacuant substances from plant extracts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1063942A true CA1063942A (en) | 1979-10-09 |
Family
ID=24535966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA264,053A Expired CA1063942A (en) | 1975-11-17 | 1976-10-25 | Isolation of utero-evacuant substances from plant extracts |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3986952A (en:Method) |
| JP (1) | JPS5942654B2 (en:Method) |
| AT (1) | AT358165B (en:Method) |
| AU (1) | AU511248B2 (en:Method) |
| BE (1) | BE848374A (en:Method) |
| CA (1) | CA1063942A (en:Method) |
| CS (1) | CS196330B2 (en:Method) |
| DE (1) | DE2652380A1 (en:Method) |
| ES (1) | ES453286A1 (en:Method) |
| FR (1) | FR2331353A1 (en:Method) |
| GB (1) | GB1542428A (en:Method) |
| GR (1) | GR62477B (en:Method) |
| HU (1) | HU174366B (en:Method) |
| IE (1) | IE43880B1 (en:Method) |
| IL (1) | IL50918A (en:Method) |
| NL (1) | NL7612787A (en:Method) |
| NZ (1) | NZ182395A (en:Method) |
| PT (1) | PT65846B (en:Method) |
| RO (1) | RO69403A2 (en:Method) |
| SE (1) | SE7612788L (en:Method) |
| YU (1) | YU276476A (en:Method) |
| ZA (1) | ZA766343B (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130556A (en) * | 1976-04-02 | 1978-12-19 | Ortho Pharmaceutical Corporation | Chemical products and methods |
| US4060604A (en) * | 1976-09-27 | 1977-11-29 | Ortho Pharmaceutical Corporation | Isolation of utero-evacuant substances from plant extracts |
| US4046882A (en) * | 1976-11-18 | 1977-09-06 | Ortho Pharmaceutical Corporation | Isolation of utero-evacuant substances from plant extracts |
| US4127651A (en) * | 1977-06-29 | 1978-11-28 | Ortho Pharmaceutical Corporation | Isolation of uteroevacuant substances from plant extracts |
| US4112078A (en) * | 1977-08-08 | 1978-09-05 | Ortho Pharmaceutical Corporation | Isolation of uteroevacuant substances from plant extracts |
| US4112079A (en) * | 1977-08-08 | 1978-09-05 | Ortho Pharmaceutical Corporation | Isolation of uteroevacuant substances from plant extracts |
| US4491593A (en) * | 1983-01-27 | 1985-01-01 | Gallegos Alfredo J | Compositions and methods for fertility control |
| EP0669151B1 (en) * | 1994-02-24 | 2003-03-26 | Matsushita Electric Industrial Co., Ltd. | Method for extracting organic substance, solvent for use in said method, and method for measuring content of organic substance |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2515670C2 (de) * | 1975-04-10 | 1985-07-25 | Ortho Pharmaceutical Corp., Raritan, N.J. | Verfahren zum Isolieren von Substanzen mit uteroevakuierender Wirkung aus der Zoapatl-Pflanze und diese Substanzen enthaltende Arzneimittel |
-
1975
- 1975-11-17 US US05/632,552 patent/US3986952A/en not_active Expired - Lifetime
-
1976
- 1976-10-22 NZ NZ182395A patent/NZ182395A/xx unknown
- 1976-10-25 ZA ZA00766343A patent/ZA766343B/xx unknown
- 1976-10-25 CA CA264,053A patent/CA1063942A/en not_active Expired
- 1976-11-03 GB GB7645748A patent/GB1542428A/en not_active Expired
- 1976-11-11 YU YU02764/76A patent/YU276476A/xx unknown
- 1976-11-12 ES ES453286A patent/ES453286A1/es not_active Expired
- 1976-11-15 JP JP51136416A patent/JPS5942654B2/ja not_active Expired
- 1976-11-15 HU HU76OO235A patent/HU174366B/hu unknown
- 1976-11-15 AU AU19644/76A patent/AU511248B2/en not_active Expired
- 1976-11-16 AT AT851876A patent/AT358165B/de not_active IP Right Cessation
- 1976-11-16 IL IL50918A patent/IL50918A/xx unknown
- 1976-11-16 SE SE7612788A patent/SE7612788L/ unknown
- 1976-11-16 IE IE2523/76A patent/IE43880B1/en unknown
- 1976-11-16 GR GR52195A patent/GR62477B/el unknown
- 1976-11-16 PT PT65846A patent/PT65846B/pt unknown
- 1976-11-16 BE BE172388A patent/BE848374A/xx not_active IP Right Cessation
- 1976-11-16 RO RO88457A patent/RO69403A2/ro unknown
- 1976-11-16 FR FR7634466A patent/FR2331353A1/fr active Granted
- 1976-11-17 CS CS767395A patent/CS196330B2/cs unknown
- 1976-11-17 DE DE19762652380 patent/DE2652380A1/de not_active Ceased
- 1976-11-17 NL NL7612787A patent/NL7612787A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ182395A (en) | 1979-03-16 |
| IL50918A0 (en) | 1977-01-31 |
| PT65846B (en) | 1978-10-12 |
| DE2652380A1 (de) | 1977-05-26 |
| JPS5942654B2 (ja) | 1984-10-16 |
| NL7612787A (nl) | 1977-05-20 |
| FR2331353B1 (en:Method) | 1978-12-22 |
| IE43880B1 (en) | 1981-06-17 |
| BE848374A (fr) | 1977-05-16 |
| CS196330B2 (en) | 1980-03-31 |
| US3986952A (en) | 1976-10-19 |
| PT65846A (en) | 1976-12-01 |
| YU276476A (en) | 1983-10-31 |
| AU1964476A (en) | 1978-05-25 |
| GR62477B (en) | 1979-04-13 |
| AT358165B (de) | 1980-08-25 |
| ATA851876A (de) | 1980-01-15 |
| ZA766343B (en) | 1978-06-28 |
| AU511248B2 (en) | 1980-08-07 |
| GB1542428A (en) | 1979-03-21 |
| FR2331353A1 (fr) | 1977-06-10 |
| IL50918A (en) | 1979-01-31 |
| JPS5282712A (en) | 1977-07-11 |
| RO69403A2 (ro) | 1980-05-26 |
| SE7612788L (sv) | 1977-05-18 |
| ES453286A1 (es) | 1977-11-01 |
| HU174366B (hu) | 1979-12-28 |
| IE43880L (en) | 1977-05-17 |
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