NO128871B - - Google Patents
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- Publication number
- NO128871B NO128871B NO04605/69A NO460569A NO128871B NO 128871 B NO128871 B NO 128871B NO 04605/69 A NO04605/69 A NO 04605/69A NO 460569 A NO460569 A NO 460569A NO 128871 B NO128871 B NO 128871B
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- coumarinyl
- hydroxy
- product
- phenyl
- Prior art date
Links
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical class C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 claims description 14
- -1 4-biphenylyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 241000283984 Rodentia Species 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 34
- 239000000047 product Substances 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229960004592 isopropanol Drugs 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000003203 everyday effect Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 4
- 229960005080 warfarin Drugs 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JPRPQUIAZJFULH-UHFFFAOYSA-N 1-piperidin-1-ylpropan-2-one;hydrochloride Chemical compound Cl.CC(=O)CN1CCCCC1 JPRPQUIAZJFULH-UHFFFAOYSA-N 0.000 description 1
- IKXXJTNYNATSSQ-UHFFFAOYSA-N 3-piperidin-1-ylpropanal Chemical class O=CCCN1CCCCC1 IKXXJTNYNATSSQ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 208000033131 Congenital factor II deficiency Diseases 0.000 description 1
- 208000007646 Hypoprothrombinemias Diseases 0.000 description 1
- 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 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 239000003698 antivitamin K Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000002299 hypoprothrombinemic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 201000007183 prothrombin deficiency Diseases 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- 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
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04G—SCAFFOLDING; FORMS; SHUTTERING; BUILDING IMPLEMENTS OR AIDS, OR THEIR USE; HANDLING BUILDING MATERIALS ON THE SITE; REPAIRING, BREAKING-UP OR OTHER WORK ON EXISTING BUILDINGS
- E04G21/00—Preparing, conveying, or working-up building materials or building elements in situ; Other devices or measures for constructional work
- E04G21/24—Safety or protective measures preventing damage to building parts or finishing work during construction
- E04G21/26—Strutting means for wall parts; Supports or the like, e.g. for holding in position prefabricated walls
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Mechanical Engineering (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Solid-Fuel Combustion (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO319970A NO124902B (fr) | 1966-12-13 | 1970-08-21 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR87213A FR1559595A (fr) | 1966-12-13 | 1966-12-13 | |
| FR127915A FR94820E (fr) | 1966-12-13 | 1967-11-13 | Nouveaux dérivés de l'hydroxy-4 coumarine et leurs procédés de préparation. |
| FR175753A FR96651E (fr) | 1966-12-13 | 1968-11-28 | Nouveaux dérives de l'hydroxy-4 coumarine et leurs procédés de préparation. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128871B true NO128871B (fr) | 1974-01-21 |
Family
ID=43971571
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO170948A NO122311B (fr) | 1966-12-13 | 1967-12-12 | |
| NO04605/69A NO128871B (fr) | 1966-12-13 | 1969-11-20 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO170948A NO122311B (fr) | 1966-12-13 | 1967-12-12 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US3574234A (fr) |
| AT (1) | AT291245B (fr) |
| BE (2) | BE707867A (fr) |
| BR (2) | BR6795401D0 (fr) |
| CH (2) | CH475234A (fr) |
| CS (2) | CS149605B2 (fr) |
| DE (2) | DE1300116B (fr) |
| DK (2) | DK122667B (fr) |
| ES (2) | ES348152A1 (fr) |
| FR (3) | FR1559595A (fr) |
| GB (2) | GB1193500A (fr) |
| IE (1) | IE33658B1 (fr) |
| IL (2) | IL29068A (fr) |
| IT (2) | IT1056721B (fr) |
| NL (2) | NL165164C (fr) |
| NO (2) | NO122311B (fr) |
| OA (2) | OA02553A (fr) |
| SE (3) | SE327208B (fr) |
| SU (1) | SU491234A3 (fr) |
| YU (2) | YU31715B (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764693A (en) * | 1969-11-21 | 1973-10-09 | Lipha | A rodenticidal compositions containing 4-hydroxy coumarins |
| FR2321238A1 (fr) * | 1975-08-19 | 1977-03-18 | Lipha | Nouvelles compositions rodenticides |
| US4188116A (en) * | 1978-02-21 | 1980-02-12 | American Optical Corporation | Abbe refractometer |
| GB8333334D0 (en) * | 1983-12-14 | 1984-01-18 | Ici Plc | Rodenticides |
| GB8729557D0 (en) | 1987-12-18 | 1988-02-03 | Shell Int Research | Rodenticidal composition |
| US5449514A (en) * | 1990-09-11 | 1995-09-12 | Liphatech, Inc. | Bait block |
| US5444042A (en) * | 1990-12-28 | 1995-08-22 | Cortex Pharmaceuticals | Method of treatment of neurodegeneration with calpain inhibitors |
| ES2048090B1 (es) * | 1992-01-31 | 1994-10-01 | Rovi Lab Farmaceut Sa | Procedimiento para la obtencion de nuevos antitromboticos derivados de la cumarina. |
| IL129871A (en) * | 1994-05-06 | 2003-11-23 | Pharmacia & Upjohn Inc | Process for preparing 4-phenyl-substituted octanoyl-oxazolidin-2-one intermediates that are useful for preparing pyran-2-ones useful for treating retroviral infections |
| GB0211019D0 (en) * | 2002-05-14 | 2002-06-26 | Syngenta Ltd | Novel compounds |
| CN101654446B (zh) * | 2008-08-19 | 2012-10-03 | 信谊药厂 | 抗凝化合物、组合物及其用途 |
| FR2978148B1 (fr) * | 2011-07-22 | 2014-03-07 | Liphatech Inc | Compose rodenticide, composition l'incluant et utilisation pour lutter contre les rongeurs nuisibles |
| RU2487871C1 (ru) * | 2012-06-25 | 2013-07-20 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупроводников и красителей" (ФГУП "ГНЦ "НИОПИК") | Способ получения 4-гидрокси-3-(3-оксо-1-фенилбутил)-2н-1-бензопиран-2-он натриевой соли |
| CN110845462B (zh) * | 2019-12-09 | 2022-05-13 | 沈阳爱威科技发展股份有限公司 | 一种控制溴敌隆液体母药异构体比例的工业生产方法 |
-
1966
- 1966-12-13 FR FR87213A patent/FR1559595A/fr not_active Expired
-
1967
- 1967-11-13 FR FR127915A patent/FR94820E/fr not_active Expired
- 1967-11-28 CH CH1672967A patent/CH475234A/fr not_active IP Right Cessation
- 1967-12-05 IL IL29068A patent/IL29068A/xx unknown
- 1967-12-07 SE SE16803/67A patent/SE327208B/xx unknown
- 1967-12-09 YU YU2412/67A patent/YU31715B/xx unknown
- 1967-12-11 IT IT23739/67A patent/IT1056721B/it active
- 1967-12-11 BR BR195401/67A patent/BR6795401D0/pt unknown
- 1967-12-11 US US689347A patent/US3574234A/en not_active Expired - Lifetime
- 1967-12-12 ES ES348152A patent/ES348152A1/es not_active Expired
- 1967-12-12 BE BE707867D patent/BE707867A/xx not_active IP Right Cessation
- 1967-12-12 NO NO170948A patent/NO122311B/no unknown
- 1967-12-12 CS CS8802A patent/CS149605B2/cs unknown
- 1967-12-12 GB GB56507/67A patent/GB1193500A/en not_active Expired
- 1967-12-12 DK DK620167AA patent/DK122667B/da not_active IP Right Cessation
- 1967-12-12 DE DEL58086A patent/DE1300116B/de active Pending
- 1967-12-13 OA OA53125A patent/OA02553A/fr unknown
- 1967-12-13 NL NL6716969.A patent/NL165164C/xx not_active IP Right Cessation
-
1968
- 1968-11-28 FR FR175753A patent/FR96651E/fr not_active Expired
-
1969
- 1969-11-18 SE SE7215171A patent/SE395145B/xx unknown
- 1969-11-18 SE SE15807/69A patent/SE363101B/xx unknown
- 1969-11-19 YU YU2895/69A patent/YU33960B/xx unknown
- 1969-11-20 DK DK614669AA patent/DK121804B/da not_active IP Right Cessation
- 1969-11-20 NO NO04605/69A patent/NO128871B/no unknown
- 1969-11-21 US US878876A patent/US3651091A/en not_active Expired - Lifetime
- 1969-11-21 CS CS7692A patent/CS159762B2/cs unknown
- 1969-11-24 ES ES373853A patent/ES373853A2/es not_active Expired
- 1969-11-24 IL IL33412A patent/IL33412A0/xx unknown
- 1969-11-24 IT IT24812/69A patent/IT1044808B/it active
- 1969-11-25 IE IE1588/69A patent/IE33658B1/xx unknown
- 1969-11-26 DE DE1959317A patent/DE1959317C3/de not_active Expired
- 1969-11-26 CH CH1765169A patent/CH498827A/fr not_active IP Right Cessation
- 1969-11-26 BR BR214559/69A patent/BR6914559D0/pt unknown
- 1969-11-27 GB GB1252088D patent/GB1252088A/en not_active Expired
- 1969-11-27 BE BE742290D patent/BE742290A/xx unknown
- 1969-11-28 SU SU1380387A patent/SU491234A3/ru active
- 1969-11-28 AT AT1113269A patent/AT291245B/de not_active IP Right Cessation
- 1969-11-28 NL NL6917942.A patent/NL164036C/xx not_active IP Right Cessation
- 1969-12-15 OA OA53806A patent/OA141E/xx unknown
-
1970
- 1970-06-11 US US45589A patent/US3651223A/en not_active Expired - Lifetime
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