DE1792295B1 - Pharmazeutisches Praeparat enthaltend 1-Aminomethyladamantan - Google Patents
Pharmazeutisches Praeparat enthaltend 1-AminomethyladamantanInfo
- Publication number
- DE1792295B1 DE1792295B1 DE19641792295 DE1792295A DE1792295B1 DE 1792295 B1 DE1792295 B1 DE 1792295B1 DE 19641792295 DE19641792295 DE 19641792295 DE 1792295 A DE1792295 A DE 1792295A DE 1792295 B1 DE1792295 B1 DE 1792295B1
- Authority
- DE
- Germany
- Prior art keywords
- adamantane
- aminomethyl
- active ingredient
- aminomethyladamantane
- weight
- 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.)
- Withdrawn
Links
- XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 title description 2
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 239000004480 active ingredient Substances 0.000 claims description 12
- 239000003443 antiviral agent Substances 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 description 17
- 208000015181 infectious disease Diseases 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- KJHOZAZQWVKILO-UHFFFAOYSA-N N-(diaminomethylidene)-4-morpholinecarboximidamide Chemical compound NC(N)=NC(=N)N1CCOCC1 KJHOZAZQWVKILO-UHFFFAOYSA-N 0.000 description 7
- 208000037797 influenza A Diseases 0.000 description 6
- 241000700605 Viruses Species 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- 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 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 206010069767 H1N1 influenza Diseases 0.000 description 1
- 241001500351 Influenzavirus A Species 0.000 description 1
- 208000009620 Orthomyxoviridae Infections Diseases 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 229960002028 atropine sulfate Drugs 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229960005389 moroxydine Drugs 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 201000010740 swine influenza Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/313—Saturated compounds containing keto groups bound to rings polycyclic
- C07C49/323—Saturated compounds containing keto groups bound to rings polycyclic having keto groups bound to condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29723363A | 1963-07-24 | 1963-07-24 | |
| US376259A US3352912A (en) | 1963-07-24 | 1964-06-18 | Adamantanes and tricyclo[4. 3. 1. 1 3.8] undecanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1792295B1 true DE1792295B1 (de) | 1971-05-27 |
Family
ID=26970055
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641792295 Withdrawn DE1792295B1 (de) | 1963-07-24 | 1964-07-18 | Pharmazeutisches Praeparat enthaltend 1-Aminomethyladamantan |
| DE19641793207 Pending DE1793207A1 (de) | 1963-07-24 | 1964-07-18 | Nicht-toxische Saeureadditionssalze von 1-(Aminomethyl)adamantan |
| DE19641793208 Pending DE1793208A1 (de) | 1963-07-24 | 1964-07-18 | Neue cyclische Kohlenwasserstoffverbindungen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641793207 Pending DE1793207A1 (de) | 1963-07-24 | 1964-07-18 | Nicht-toxische Saeureadditionssalze von 1-(Aminomethyl)adamantan |
| DE19641793208 Pending DE1793208A1 (de) | 1963-07-24 | 1964-07-18 | Neue cyclische Kohlenwasserstoffverbindungen |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3352912A (enExample) |
| AT (1) | AT279581B (enExample) |
| BE (1) | BE650919A (enExample) |
| BR (1) | BR6460975D0 (enExample) |
| CH (2) | CH476673A (enExample) |
| DE (3) | DE1792295B1 (enExample) |
| DK (3) | DK112027B (enExample) |
| ES (1) | ES302369A1 (enExample) |
| FI (3) | FI42322B (enExample) |
| FR (1) | FR1572956A (enExample) |
| GB (1) | GB1069563A (enExample) |
| IL (1) | IL21753A (enExample) |
| NL (2) | NL6408505A (enExample) |
| SE (3) | SE320363B (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449422A (en) * | 1966-02-09 | 1969-06-10 | Smithkline Corp | Pentacycloundecane amines |
| DE1294371B (de) * | 1966-12-21 | 1969-05-08 | Penicillin Ges Dauelsberg & Co | Verfahren zur Herstellung von 1-Aminoadamantan und dessen N-Alkyl- bzw. N-Cyclohexylderivaten |
| US3489802A (en) * | 1967-01-23 | 1970-01-13 | Du Pont | Preparation of alpha-methyl-1-adamantane-methylamine and alpha,4 - dimethyl - 1 - bicyclo(2,2,2)octane methylamine |
| NL6900004A (enExample) * | 1969-01-02 | 1970-07-06 | ||
| US3682922A (en) * | 1969-01-16 | 1972-08-08 | Searle & Co | N-acyl-n-{8 (n{40 ,n{40 -disubstituted amino)-alkyl{9 -1-adamantylmethylamines |
| JPS4828903B1 (enExample) * | 1969-07-19 | 1973-09-05 | ||
| US3624086A (en) * | 1969-11-10 | 1971-11-30 | Searle & Co | Adamantanecarboxamidoalkanoic acid amides |
| US3852339A (en) * | 1970-06-15 | 1974-12-03 | Squibb & Sons Inc | Aminoalkoxyphenylurea derivatives |
| US3879400A (en) * | 1973-11-16 | 1975-04-22 | Upjohn Co | 1-Lower alkyl-(1-adamantylmethyl)piperidines and process for their preparation |
| JPS5346950A (en) * | 1976-10-12 | 1978-04-27 | Kao Corp | (54)1-acetylaminotricyclo(4,3,1,12,5)undecane and its preparation |
| US4351847A (en) * | 1981-06-26 | 1982-09-28 | Pennwalt Corporation | Antiviral alpha, alpha-dialkyl adamantylethylamines |
| US4551552A (en) * | 1984-05-23 | 1985-11-05 | E. I. Du Pont De Nemours And Company | Process for preparing rimantadine |
| US4751245A (en) * | 1986-06-25 | 1988-06-14 | E. R. Squibb & Sons, Inc. | Antifungal derivatives of N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine and method of using same |
| US5576355A (en) * | 1993-06-04 | 1996-11-19 | Mobil Oil Corp. | Diamondoid derivatives for pharmaceutical use |
| US5684024A (en) * | 1996-01-25 | 1997-11-04 | Viropharma Incorporated | Pyrazole dimers compositions and methods for treating influenza |
| US5821243A (en) * | 1996-07-22 | 1998-10-13 | Viropharma Incorporated | Compounds compositions and methods for treating influenza |
| DE69805909T2 (de) * | 1997-04-10 | 2002-09-26 | Pfizer Inc., New York | Fluorosubstituierte Adamantan-Derivate |
| GB0013737D0 (en) | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
| WO2003004461A1 (en) * | 2001-07-02 | 2003-01-16 | Schering Corporation | Drugs for treating viral infections |
| SE0103836D0 (sv) * | 2001-11-16 | 2001-11-16 | Astrazeneca Ab | Novel compounds |
| EP2316468A1 (en) | 2002-02-22 | 2011-05-04 | Shire LLC | Delivery system and methods for protecting and administering dextroamphetamine |
| WO2004056744A1 (en) * | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| SE0300480D0 (sv) | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
| GB0312609D0 (en) | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| MX2007015863A (es) * | 2005-06-17 | 2008-04-02 | Apogee Biotechnology Corp | Inhibidores de esfingosina cinasa. |
| AR057623A1 (es) | 2005-11-28 | 2007-12-05 | Omega Bio Pharma H K Ltd | Materiales y metodos para el tratamiento de las infecciones virales |
| RU2460727C2 (ru) | 2007-03-22 | 2012-09-10 | Астразенека Аб | Хинолиновые производные для лечения воспалительных заболеваний |
| RU2348611C1 (ru) * | 2007-05-02 | 2009-03-10 | Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ) | Способ получения n,n-диалкилзамещенных амидов адамантилалкилкарбоновых кислот |
| RU2344122C1 (ru) * | 2007-07-09 | 2009-01-20 | Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ) | Способ получения диалкиламидов 3-бром-1-адамантилалканкарбоновых кислот |
| PE20091036A1 (es) | 2007-11-30 | 2009-08-15 | Astrazeneca Ab | Derivado de quinolina como antagonista del receptor p2x7 |
| US9227990B2 (en) | 2012-10-29 | 2016-01-05 | Cipla Limited | Antiviral phosphonate analogues and process for preparation thereof |
| JP6434980B2 (ja) * | 2013-12-09 | 2018-12-05 | ユニリーバー・ナームローゼ・ベンノートシヤープ | アダマンタンアミド製造方法 |
| WO2017093354A1 (en) | 2015-11-30 | 2017-06-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Nmdar antagonists for the treatment of diseases associated with angiogenesis |
| US11548893B2 (en) | 2017-07-15 | 2023-01-10 | Arisan Therapeutics Inc. | Enantiomerically pure adamantane carboxamides for the treatment of filovirus infection |
| CN121490829B (zh) * | 2026-01-14 | 2026-06-02 | 山东新和成药业有限公司 | 一种复合催化剂及其制备方法和应用 |
-
1964
- 1964-06-18 US US376259A patent/US3352912A/en not_active Expired - Lifetime
- 1964-07-18 DE DE19641792295 patent/DE1792295B1/de not_active Withdrawn
- 1964-07-18 DE DE19641793207 patent/DE1793207A1/de active Pending
- 1964-07-18 DE DE19641793208 patent/DE1793208A1/de active Pending
- 1964-07-20 CH CH946964A patent/CH476673A/de not_active IP Right Cessation
- 1964-07-20 BR BR160975/64A patent/BR6460975D0/pt unknown
- 1964-07-20 CH CH1457468A patent/CH479535A/de not_active IP Right Cessation
- 1964-07-23 SE SE9752/67A patent/SE320363B/xx unknown
- 1964-07-23 DK DK367964AA patent/DK112027B/da unknown
- 1964-07-23 SE SE09751/67A patent/SE330693B/xx unknown
- 1964-07-23 ES ES0302369A patent/ES302369A1/es not_active Expired
- 1964-07-23 SE SE8987/64A patent/SE321924B/xx unknown
- 1964-07-23 IL IL21753A patent/IL21753A/xx unknown
- 1964-07-23 FI FI1584/64A patent/FI42322B/fi active
- 1964-07-23 BE BE650919D patent/BE650919A/xx unknown
- 1964-07-24 FR FR1572956D patent/FR1572956A/fr not_active Expired
- 1964-07-24 NL NL6408505A patent/NL6408505A/xx unknown
- 1964-08-04 GB GB30940/64A patent/GB1069563A/en not_active Expired
- 1964-08-07 AT AT06819/68A patent/AT279581B/de not_active IP Right Cessation
-
1965
- 1965-07-09 DK DK353265AA patent/DK114769B/da unknown
- 1965-07-09 DK DK353365AA patent/DK114199B/da unknown
-
1969
- 1969-01-22 FI FI0198/69A patent/FI42211B/fi active
- 1969-01-22 FI FI0197/69A patent/FI42548B/fi active
-
1971
- 1971-02-17 NL NL7102097A patent/NL7102097A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| CH476673A (de) | 1969-08-15 |
| SE330693B (enExample) | 1970-11-30 |
| SE321924B (enExample) | 1970-03-23 |
| FI42322B (enExample) | 1970-03-31 |
| DE1793207A1 (de) | 1972-03-30 |
| DE1468769B1 (de) | 1972-06-29 |
| ES302369A1 (es) | 1965-03-16 |
| IL21753A (en) | 1968-01-25 |
| US3352912A (en) | 1967-11-14 |
| BR6460975D0 (pt) | 1973-08-09 |
| NL6408505A (enExample) | 1965-01-25 |
| DE1793208A1 (de) | 1972-04-06 |
| AT279581B (de) | 1970-03-10 |
| DK114769B (da) | 1969-08-04 |
| FI42211B (enExample) | 1970-03-02 |
| DK114199B (da) | 1969-06-09 |
| FR1572956A (enExample) | 1969-07-04 |
| NL7102097A (enExample) | 1971-05-25 |
| CH479535A (de) | 1969-10-15 |
| GB1069563A (en) | 1967-05-17 |
| SE320363B (enExample) | 1970-02-09 |
| FI42548B (enExample) | 1970-06-01 |
| BE650919A (enExample) | 1964-11-16 |
| DK112027B (da) | 1968-11-04 |
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