IL44065A - Metabolite a-27106 and process for its preparation and its use as coccidiostatic agent and feed additive - Google Patents
Metabolite a-27106 and process for its preparation and its use as coccidiostatic agent and feed additiveInfo
- Publication number
- IL44065A IL44065A IL44065A IL4406574A IL44065A IL 44065 A IL44065 A IL 44065A IL 44065 A IL44065 A IL 44065A IL 4406574 A IL4406574 A IL 4406574A IL 44065 A IL44065 A IL 44065A
- Authority
- IL
- Israel
- Prior art keywords
- metabolite
- monensin
- feed
- culture medium
- poultry
- Prior art date
Links
- 239000002207 metabolite Substances 0.000 title claims abstract description 103
- 238000000034 method Methods 0.000 title claims description 38
- 230000008569 process Effects 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 8
- 239000003224 coccidiostatic agent Substances 0.000 title description 5
- 239000003674 animal food additive Substances 0.000 title description 2
- NHWHEEBAHRSUTF-UHFFFAOYSA-N 4-[2-[5-ethyl-5-[5-[6-hydroxy-3,5-dimethyl-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]-3-methyloxolan-2-yl]oxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methylpentanoic acid Chemical compound O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(COC3C(C(O)C(O)C(CO)O3)O)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 NHWHEEBAHRSUTF-UHFFFAOYSA-N 0.000 claims abstract description 113
- 229930191564 Monensin Natural products 0.000 claims abstract description 49
- GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 claims abstract description 49
- 229960005358 monensin Drugs 0.000 claims abstract description 49
- GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 claims abstract description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000001963 growth medium Substances 0.000 claims abstract description 26
- 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 claims abstract description 23
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 23
- 241000958233 Streptomyces candidus Species 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 20
- 239000008103 glucose Substances 0.000 claims abstract description 18
- 208000003495 Coccidiosis Diseases 0.000 claims abstract description 17
- 206010023076 Isosporiasis Diseases 0.000 claims abstract description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 241000282849 Ruminantia Species 0.000 claims abstract description 15
- 244000144977 poultry Species 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 10
- 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 claims abstract description 10
- 239000011734 sodium Substances 0.000 claims abstract description 8
- 238000004809 thin layer chromatography Methods 0.000 claims abstract description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 7
- 239000000741 silica gel Substances 0.000 claims abstract description 7
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 7
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 239000011591 potassium Substances 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 5
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims abstract description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000862 absorption spectrum Methods 0.000 claims abstract description 4
- 229960004217 benzyl alcohol Drugs 0.000 claims abstract description 4
- 150000001793 charged compounds Chemical class 0.000 claims abstract description 4
- 238000001819 mass spectrum Methods 0.000 claims abstract description 4
- 238000004949 mass spectrometry Methods 0.000 claims abstract description 3
- 239000002609 medium Substances 0.000 claims description 41
- 241001465754 Metazoa Species 0.000 claims description 16
- 210000004767 rumen Anatomy 0.000 claims description 13
- 239000000872 buffer Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 241000283690 Bos taurus Species 0.000 claims description 6
- 229960001866 silicon dioxide Drugs 0.000 claims description 6
- 241000187434 Streptomyces cinnamonensis Species 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 239000012062 aqueous buffer Substances 0.000 claims description 3
- 230000002192 coccidiostatic effect Effects 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000527 sonication Methods 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 238000000502 dialysis Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000012010 growth Effects 0.000 description 30
- 238000000855 fermentation Methods 0.000 description 22
- 230000004151 fermentation Effects 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 210000004215 spore Anatomy 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000049 pigment Substances 0.000 description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 241000271566 Aves Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910000019 calcium carbonate Inorganic materials 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 239000002054 inoculum Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- -1 aliphatic alcohols Chemical class 0.000 description 8
- 235000005822 corn Nutrition 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- 235000019764 Soybean Meal Nutrition 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 150000001720 carbohydrates Chemical class 0.000 description 5
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- 238000010828 elution Methods 0.000 description 5
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 4
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- 241000187747 Streptomyces Species 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 4
- 208000021017 Weight Gain Diseases 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
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- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 3
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- 235000019739 Dicalciumphosphate Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000032843 Hemorrhage Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 239000001506 calcium phosphate Substances 0.000 description 3
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- 238000011161 development Methods 0.000 description 2
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- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
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- 238000000921 elemental analysis Methods 0.000 description 2
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Mycology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Alternative & Traditional Medicine (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Fodder In General (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)
- Feed For Specific Animals (AREA)
- Saccharide Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Compounds Of Unknown Constitution (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32858673A | 1973-02-01 | 1973-02-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44065A0 IL44065A0 (en) | 1974-05-16 |
| IL44065A true IL44065A (en) | 1977-03-31 |
Family
ID=23281582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44065A IL44065A (en) | 1973-02-01 | 1974-01-22 | Metabolite a-27106 and process for its preparation and its use as coccidiostatic agent and feed additive |
Country Status (27)
| Country | Link |
|---|---|
| JP (2) | JPS5730477B2 (cs) |
| AR (1) | AR206509A1 (cs) |
| AT (1) | AT328083B (cs) |
| BE (1) | BE810416A (cs) |
| BG (1) | BG26953A3 (cs) |
| CA (1) | CA1016483A (cs) |
| CH (1) | CH589140A5 (cs) |
| CS (1) | CS193481B2 (cs) |
| DD (1) | DD112441A5 (cs) |
| DE (1) | DE2404958C2 (cs) |
| DK (1) | DK143036C (cs) |
| EG (1) | EG11287A (cs) |
| ES (1) | ES422834A1 (cs) |
| FI (1) | FI52993C (cs) |
| FR (1) | FR2215943B1 (cs) |
| GB (1) | GB1457796A (cs) |
| HU (1) | HU167276B (cs) |
| IE (1) | IE38780B1 (cs) |
| IL (1) | IL44065A (cs) |
| IN (1) | IN139462B (cs) |
| NL (1) | NL181367C (cs) |
| NO (1) | NO139788C (cs) |
| PH (1) | PH12449A (cs) |
| SE (1) | SE401930B (cs) |
| SU (1) | SU539538A3 (cs) |
| YU (1) | YU36990B (cs) |
| ZA (1) | ZA74464B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6384471U (cs) * | 1986-11-21 | 1988-06-02 | ||
| JPH0483920U (cs) * | 1990-11-30 | 1992-07-21 | ||
| JPH0512236U (ja) * | 1991-07-26 | 1993-02-19 | 東京ラヂエーター製造株式会社 | 燃料タンクの燃料吹き返し防止構造 |
-
1974
- 1974-01-01 AR AR252171A patent/AR206509A1/es active
- 1974-01-22 CA CA190,655A patent/CA1016483A/en not_active Expired
- 1974-01-22 IL IL44065A patent/IL44065A/en unknown
- 1974-01-22 ZA ZA00740464A patent/ZA74464B/xx unknown
- 1974-01-22 IE IE129/74A patent/IE38780B1/xx unknown
- 1974-01-24 PH PH15441A patent/PH12449A/en unknown
- 1974-01-25 YU YU0190/74A patent/YU36990B/xx unknown
- 1974-01-29 IN IN191/CAL/74A patent/IN139462B/en unknown
- 1974-01-30 NO NO740292A patent/NO139788C/no unknown
- 1974-01-30 GB GB441474A patent/GB1457796A/en not_active Expired
- 1974-01-30 NL NLAANVRAGE7401311,A patent/NL181367C/xx not_active IP Right Cessation
- 1974-01-31 HU HUEI523A patent/HU167276B/hu not_active IP Right Cessation
- 1974-01-31 BE BE1005684A patent/BE810416A/xx not_active IP Right Cessation
- 1974-01-31 SE SE7401314A patent/SE401930B/xx not_active IP Right Cessation
- 1974-01-31 DK DK51474A patent/DK143036C/da not_active IP Right Cessation
- 1974-01-31 AT AT76874*#A patent/AT328083B/de not_active IP Right Cessation
- 1974-01-31 DD DD176301A patent/DD112441A5/xx unknown
- 1974-01-31 ES ES422834A patent/ES422834A1/es not_active Expired
- 1974-02-01 FI FI283/74A patent/FI52993C/fi active
- 1974-02-01 BG BG025678A patent/BG26953A3/xx unknown
- 1974-02-01 CS CS74699A patent/CS193481B2/cs unknown
- 1974-02-01 SU SU2002131A patent/SU539538A3/ru active
- 1974-02-01 JP JP1403874A patent/JPS5730477B2/ja not_active Expired
- 1974-02-01 CH CH143874A patent/CH589140A5/xx not_active IP Right Cessation
- 1974-02-01 FR FR7403437A patent/FR2215943B1/fr not_active Expired
- 1974-02-01 DE DE2404958A patent/DE2404958C2/de not_active Expired
- 1974-02-02 EG EG29/74A patent/EG11287A/xx active
-
1981
- 1981-10-20 JP JP56168525A patent/JPS6026374B2/ja not_active Expired
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