NO131080B - - Google Patents
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- Publication number
- NO131080B NO131080B NO03958/70A NO395870A NO131080B NO 131080 B NO131080 B NO 131080B NO 03958/70 A NO03958/70 A NO 03958/70A NO 395870 A NO395870 A NO 395870A NO 131080 B NO131080 B NO 131080B
- Authority
- NO
- Norway
- Prior art keywords
- oudenon
- oudenone
- solution
- mcg
- ethyl acetate
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- -1 alkaline earth metal salts Chemical class 0.000 claims description 6
- 241000315067 Hymenopellis radicata Species 0.000 claims description 5
- 230000001077 hypotensive effect Effects 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 208000001953 Hypotension Diseases 0.000 claims description 3
- 208000021822 hypotensive Diseases 0.000 claims description 3
- 235000015097 nutrients Nutrition 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 239000001963 growth medium Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 35
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 34
- AFHDYMGMZUYZQT-UHFFFAOYSA-N Oudenone Natural products O1C(CCC)CCC1=C1C(=O)CCC1=O AFHDYMGMZUYZQT-UHFFFAOYSA-N 0.000 description 33
- AFHDYMGMZUYZQT-QMMMGPOBSA-N oudenone Chemical compound O1[C@@H](CCC)CCC1=C1C(=O)CCC1=O AFHDYMGMZUYZQT-QMMMGPOBSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000758 substrate Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 239000011734 sodium Substances 0.000 description 18
- 239000006188 syrup Substances 0.000 description 17
- 235000020357 syrup Nutrition 0.000 description 17
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 15
- 239000008103 glucose Substances 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 13
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
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- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 7
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- 239000000706 filtrate Substances 0.000 description 5
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
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- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 2
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- 229940041514 candida albicans extract Drugs 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OCKPCBLVNKHBMX-UHFFFAOYSA-N n-butyl-benzene Natural products CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Biotechnology (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45008984A JPS4945588B1 (enExample) | 1970-02-03 | 1970-02-03 | |
| JP3977270A JPS5016406B1 (enExample) | 1970-05-12 | 1970-05-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131080B true NO131080B (enExample) | 1974-12-23 |
| NO131080C NO131080C (enExample) | 1975-04-02 |
Family
ID=26343622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3958/70A NO131080C (enExample) | 1970-02-03 | 1970-10-20 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3835170A (enExample) |
| AR (1) | AR192565A1 (enExample) |
| AT (1) | AT308693B (enExample) |
| AU (1) | AU2142970A (enExample) |
| BE (1) | BE760023A (enExample) |
| CA (1) | CA938903A (enExample) |
| CH (1) | CH552585A (enExample) |
| CS (1) | CS160136B2 (enExample) |
| DE (1) | DE2058915A1 (enExample) |
| DK (1) | DK129860B (enExample) |
| ES (1) | ES385461A1 (enExample) |
| FI (1) | FI47497C (enExample) |
| FR (1) | FR2079198B1 (enExample) |
| IE (1) | IE34666B1 (enExample) |
| IL (1) | IL35507A (enExample) |
| LU (1) | LU61999A1 (enExample) |
| NL (1) | NL7016951A (enExample) |
| NO (1) | NO131080C (enExample) |
| PL (1) | PL81044B1 (enExample) |
| RO (1) | RO59389A (enExample) |
| SE (1) | SE364985B (enExample) |
| SU (1) | SU374812A3 (enExample) |
| ZA (1) | ZA707140B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5413512B1 (enExample) * | 1971-03-26 | 1979-05-31 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1163910A (en) * | 1965-12-17 | 1969-09-10 | Ceskoslovenska Akademie Ved | A Method of Preparing a New Antifungal Antibiotic Material |
-
0
- BE BE760023D patent/BE760023A/xx unknown
-
1970
- 1970-10-19 FI FI702813A patent/FI47497C/fi active
- 1970-10-20 NO NO3958/70A patent/NO131080C/no unknown
- 1970-10-20 CA CA095985A patent/CA938903A/en not_active Expired
- 1970-10-20 DK DK534170AA patent/DK129860B/da unknown
- 1970-10-20 ZA ZA707140A patent/ZA707140B/xx unknown
- 1970-10-21 PL PL1970144003A patent/PL81044B1/pl unknown
- 1970-10-21 IL IL35507A patent/IL35507A/xx unknown
- 1970-10-21 IE IE1353/70A patent/IE34666B1/xx unknown
- 1970-10-22 AU AU21429/70A patent/AU2142970A/en not_active Expired
- 1970-10-29 FR FR7039886A patent/FR2079198B1/fr not_active Expired
- 1970-11-03 SE SE14864/70A patent/SE364985B/xx unknown
- 1970-11-05 LU LU61999D patent/LU61999A1/xx unknown
- 1970-11-11 AT AT1015870A patent/AT308693B/de not_active IP Right Cessation
- 1970-11-12 ES ES385461A patent/ES385461A1/es not_active Expired
- 1970-11-17 AR AR232431A patent/AR192565A1/es active
- 1970-11-17 RO RO65000A patent/RO59389A/ro unknown
- 1970-11-19 NL NL7016951A patent/NL7016951A/xx unknown
- 1970-11-30 DE DE19702058915 patent/DE2058915A1/de active Pending
- 1970-12-11 CH CH1842170A patent/CH552585A/xx not_active IP Right Cessation
-
1971
- 1971-01-15 US US00106746A patent/US3835170A/en not_active Expired - Lifetime
- 1971-01-18 CS CS324A patent/CS160136B2/cs unknown
- 1971-03-22 SU SU1633775A patent/SU374812A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AR192565A1 (es) | 1973-02-28 |
| FR2079198A1 (enExample) | 1971-11-12 |
| ES385461A1 (es) | 1973-11-16 |
| BE760023A (fr) | 1971-05-17 |
| CA938903A (en) | 1973-12-25 |
| CH552585A (de) | 1974-08-15 |
| DK129860C (enExample) | 1975-05-12 |
| ZA707140B (en) | 1971-07-28 |
| US3835170A (en) | 1974-09-10 |
| IE34666L (en) | 1971-08-03 |
| NL7016951A (enExample) | 1971-08-05 |
| IE34666B1 (en) | 1975-07-09 |
| DE2058915A1 (de) | 1971-08-12 |
| SU374812A3 (enExample) | 1973-03-20 |
| DK129860B (da) | 1974-11-25 |
| NO131080C (enExample) | 1975-04-02 |
| IL35507A0 (en) | 1970-12-24 |
| AT308693B (de) | 1973-07-10 |
| SE364985B (enExample) | 1974-03-11 |
| CS160136B2 (enExample) | 1975-02-28 |
| FR2079198B1 (enExample) | 1974-08-30 |
| FI47497C (fi) | 1973-12-10 |
| AU2142970A (en) | 1972-04-27 |
| LU61999A1 (enExample) | 1971-05-10 |
| PL81044B1 (en) | 1975-08-30 |
| FI47497B (enExample) | 1973-08-31 |
| IL35507A (en) | 1974-01-14 |
| RO59389A (enExample) | 1976-07-15 |
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