IE45886B1 - Process for the preparation of an extract of teucrium marum useful in therapy - Google Patents
Process for the preparation of an extract of teucrium marum useful in therapyInfo
- Publication number
- IE45886B1 IE45886B1 IE2067/77A IE206777A IE45886B1 IE 45886 B1 IE45886 B1 IE 45886B1 IE 2067/77 A IE2067/77 A IE 2067/77A IE 206777 A IE206777 A IE 206777A IE 45886 B1 IE45886 B1 IE 45886B1
- Authority
- IE
- Ireland
- Prior art keywords
- extract
- hexane
- ether
- process according
- mixture
- Prior art date
Links
- 239000000284 extract Substances 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 37
- 241000083821 Teucrium marum Species 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000002560 therapeutic procedure Methods 0.000 title abstract description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 229910001868 water Inorganic materials 0.000 claims abstract description 32
- 241000196324 Embryophyta Species 0.000 claims abstract description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000000746 purification Methods 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 10
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000009835 boiling Methods 0.000 claims abstract description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003208 petroleum Substances 0.000 claims abstract description 5
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims abstract description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 34
- 229920005989 resin Polymers 0.000 claims description 29
- 239000011347 resin Substances 0.000 claims description 29
- 238000010521 absorption reaction Methods 0.000 claims description 20
- 238000001704 evaporation Methods 0.000 claims description 17
- 239000000377 silicon dioxide Substances 0.000 claims description 17
- 238000010828 elution Methods 0.000 claims description 16
- 230000008020 evaporation Effects 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000002198 insoluble material Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 4
- 235000012141 vanillin Nutrition 0.000 claims description 4
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000002329 infrared spectrum Methods 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000000047 product Substances 0.000 description 14
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 206010006482 Bronchospasm Diseases 0.000 description 8
- 208000009079 Bronchial Spasm Diseases 0.000 description 7
- 208000014181 Bronchial disease Diseases 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000002921 anti-spasmodic effect Effects 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000556 agonist Substances 0.000 description 5
- 239000006286 aqueous extract Substances 0.000 description 5
- 229960001340 histamine Drugs 0.000 description 5
- 210000003405 ileum Anatomy 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 241000700198 Cavia Species 0.000 description 4
- 108010058846 Ovalbumin Proteins 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 229940092253 ovalbumin Drugs 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 208000028004 allergic respiratory disease Diseases 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000812 cholinergic antagonist Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 210000001198 duodenum Anatomy 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229960005181 morphine Drugs 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 201000004335 respiratory allergy Diseases 0.000 description 3
- 230000000241 respiratory effect Effects 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 239000008237 rinsing water Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 210000004291 uterus Anatomy 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241001072888 Teucrium Species 0.000 description 2
- 230000003555 analeptic effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000794 anti-serotonin Effects 0.000 description 2
- 239000003420 antiserotonin agent Substances 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002803 maceration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003169 respiratory stimulant agent Substances 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 101001018064 Homo sapiens Lysosomal-trafficking regulator Proteins 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 241000207923 Lamiaceae Species 0.000 description 1
- 102100033472 Lysosomal-trafficking regulator Human genes 0.000 description 1
- 244000038561 Modiola caroliniana Species 0.000 description 1
- 235000010703 Modiola caroliniana Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 241001342522 Vampyrum spectrum Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002804 anti-anaphylactic effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
- 229960000452 diethylstilbestrol Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229940074869 marquis Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- VBUNOIXRZNJNAD-UHFFFAOYSA-N ponazuril Chemical compound CC1=CC(N2C(N(C)C(=O)NC2=O)=O)=CC=C1OC1=CC=C(S(=O)(=O)C(F)(F)F)C=C1 VBUNOIXRZNJNAD-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000820 toxicity test Toxicity 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
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Epidemiology (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Alternative & Traditional Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB43043/76A GB1551289A (en) | 1976-10-15 | 1976-10-15 | Process for the preparation of an extract of teuerium marum useful in therapy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE45886L IE45886L (en) | 1978-04-15 |
| IE45886B1 true IE45886B1 (en) | 1982-12-29 |
Family
ID=10427076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2067/77A IE45886B1 (en) | 1976-10-15 | 1977-10-10 | Process for the preparation of an extract of teucrium marum useful in therapy |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4151278A (OSRAM) |
| JP (1) | JPS5350315A (OSRAM) |
| AR (1) | AR214900A1 (OSRAM) |
| AU (1) | AU513960B2 (OSRAM) |
| BE (1) | BE859721A (OSRAM) |
| CA (1) | CA1084902A (OSRAM) |
| DE (1) | DE2746266A1 (OSRAM) |
| ES (1) | ES463260A1 (OSRAM) |
| FR (1) | FR2367774A1 (OSRAM) |
| GB (1) | GB1551289A (OSRAM) |
| GR (1) | GR62639B (OSRAM) |
| IE (1) | IE45886B1 (OSRAM) |
| NL (1) | NL188267C (OSRAM) |
| ZA (1) | ZA776060B (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856946A (en) * | 1966-06-10 | 1974-12-24 | Debat Lab | Prunus africana extract |
-
1976
- 1976-10-15 GB GB43043/76A patent/GB1551289A/en not_active Expired
-
1977
- 1977-09-29 GR GR54462A patent/GR62639B/el unknown
- 1977-10-10 FR FR7730437A patent/FR2367774A1/fr active Granted
- 1977-10-10 IE IE2067/77A patent/IE45886B1/en unknown
- 1977-10-11 AR AR269531A patent/AR214900A1/es active
- 1977-10-11 ZA ZA00776060A patent/ZA776060B/xx unknown
- 1977-10-12 CA CA288,582A patent/CA1084902A/en not_active Expired
- 1977-10-14 DE DE19772746266 patent/DE2746266A1/de active Granted
- 1977-10-14 JP JP12397377A patent/JPS5350315A/ja active Granted
- 1977-10-14 ES ES463260A patent/ES463260A1/es not_active Expired
- 1977-10-14 US US05/842,364 patent/US4151278A/en not_active Expired - Lifetime
- 1977-10-14 AU AU29758/77A patent/AU513960B2/en not_active Expired
- 1977-10-14 NL NLAANVRAGE7711302,A patent/NL188267C/xx not_active IP Right Cessation
- 1977-10-14 BE BE2056341A patent/BE859721A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU513960B2 (en) | 1981-01-15 |
| NL7711302A (nl) | 1978-04-18 |
| NL188267C (nl) | 1992-05-18 |
| FR2367774B1 (OSRAM) | 1980-05-16 |
| ES463260A1 (es) | 1978-07-16 |
| NL188267B (nl) | 1991-12-16 |
| GB1551289A (en) | 1979-08-30 |
| ZA776060B (en) | 1978-05-30 |
| CA1084902A (en) | 1980-09-02 |
| JPH0114207B2 (OSRAM) | 1989-03-10 |
| BE859721A (fr) | 1978-02-01 |
| DE2746266A1 (de) | 1978-04-27 |
| GR62639B (en) | 1979-05-15 |
| AU2975877A (en) | 1979-04-26 |
| IE45886L (en) | 1978-04-15 |
| AR214900A1 (es) | 1979-08-15 |
| JPS5350315A (en) | 1978-05-08 |
| FR2367774A1 (fr) | 1978-05-12 |
| US4151278A (en) | 1979-04-24 |
| DE2746266C2 (OSRAM) | 1987-10-15 |
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