DE2362278C2 - 5-(2-Hydroxy-3-alkylamino)-propoxycarbostyril-Verbindungen, deren Salze mit Säuren, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel - Google Patents
5-(2-Hydroxy-3-alkylamino)-propoxycarbostyril-Verbindungen, deren Salze mit Säuren, Verfahren zu deren Herstellung und diese Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE2362278C2 DE2362278C2 DE2362278A DE2362278A DE2362278C2 DE 2362278 C2 DE2362278 C2 DE 2362278C2 DE 2362278 A DE2362278 A DE 2362278A DE 2362278 A DE2362278 A DE 2362278A DE 2362278 C2 DE2362278 C2 DE 2362278C2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- propoxycarbostyril
- hydroxy
- cooh
- comparison
- 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.)
- Expired
Links
- YNZNESKPSHZISM-UHFFFAOYSA-N 3-propoxy-1h-quinolin-2-one Chemical class C1=CC=C2NC(=O)C(OCCC)=CC2=C1 YNZNESKPSHZISM-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title description 19
- 239000002253 acid Substances 0.000 title description 6
- 150000003839 salts Chemical class 0.000 title description 6
- 150000007513 acids Chemical class 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 4
- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 14
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 10
- 102100038239 Protein Churchill Human genes 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WJSBHROJDVWBGB-UHFFFAOYSA-N 5-(oxiran-2-ylmethoxy)-1h-quinolin-2-one Chemical class C1=CC=C2NC(=O)C=CC2=C1OCC1CO1 WJSBHROJDVWBGB-UHFFFAOYSA-N 0.000 description 4
- XOXGLLQTNQBDKL-UHFFFAOYSA-N 5-hydroxyquinolin-2(1H)-one Chemical class N1C(=O)C=CC2=C1C=CC=C2O XOXGLLQTNQBDKL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N carbostyril Natural products C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 4
- -1 carbostyril compound Chemical class 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229960001317 isoprenaline Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 229940039009 isoproterenol Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- AQKPYMCBUMYZNK-UHFFFAOYSA-N 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1h-quinolin-2-one;hydrochloride Chemical compound Cl.N1C(=O)C=CC2=C1C=CC=C2OCC(O)CNC(C)(C)C AQKPYMCBUMYZNK-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- GYESAYHWISMZOK-UHFFFAOYSA-N quinolin-5-ol Chemical compound C1=CC=C2C(O)=CC=CC2=N1 GYESAYHWISMZOK-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47125857A JPS5239035B2 (en:Method) | 1972-12-14 | 1972-12-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2362278A1 DE2362278A1 (de) | 1974-06-20 |
| DE2362278C2 true DE2362278C2 (de) | 1983-03-24 |
Family
ID=14920647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2362278A Expired DE2362278C2 (de) | 1972-12-14 | 1973-12-14 | 5-(2-Hydroxy-3-alkylamino)-propoxycarbostyril-Verbindungen, deren Salze mit Säuren, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3953456A (en:Method) |
| JP (1) | JPS5239035B2 (en:Method) |
| AR (1) | AR197270A1 (en:Method) |
| BE (1) | BE808593A (en:Method) |
| CA (1) | CA1022555A (en:Method) |
| CH (1) | CH589060A5 (en:Method) |
| DE (1) | DE2362278C2 (en:Method) |
| DK (1) | DK136861B (en:Method) |
| ES (1) | ES421430A1 (en:Method) |
| FR (1) | FR2210408B1 (en:Method) |
| NL (1) | NL166931C (en:Method) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4022784A (en) * | 1974-01-31 | 1977-05-10 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-substituted-carbostyril and -3,4-dihydrocarbostyril derivatives |
| FI58329C (fi) * | 1974-11-08 | 1981-01-12 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av i 8-staellning substituerade 5-(3'-alkylamino-2'-hydroxi)propoxi-3,4-dihydrokarbostyrilderivat |
| GB1504424A (en) * | 1975-08-09 | 1978-03-22 | Beecham Group Ltd | Isoquinoline-derived aminoethers |
| CH619453A5 (en:Method) * | 1976-03-17 | 1980-09-30 | Otsuka Pharma Co Ltd | |
| DE2719562C2 (de) * | 1976-05-08 | 1986-05-07 | Otsuka Pharmaceutical Co. Ltd., Tokio/Tokyo | 3, 4-Dihydrocarbostyrilderivate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten |
| US4139537A (en) * | 1976-06-29 | 1979-02-13 | Cooper Laboratories, Inc. | 3-Aryloxy-1-(2- or 4-iminodihydro-1-pyridyl)-2-propanol antiarrhythmic compounds |
| IE46852B1 (en) * | 1977-06-10 | 1983-10-05 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives |
| AU518814B2 (en) * | 1979-01-30 | 1981-10-22 | Otsuka Pharamaceutical Co. | Glaucoma treatment |
| DE2934609A1 (de) | 1979-08-28 | 1981-03-12 | Cassella Ag, 6000 Frankfurt | Tetrahydrochinolinderivate, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende pharmazeutische zubereitungen. |
| DE3034237A1 (de) * | 1979-09-18 | 1981-04-16 | Otsuka Pharmaceutical Co. Ltd., Tokyo | Carbostyrilderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende, antihistaminisch wirkende mittel |
| PH17194A (en) * | 1980-03-06 | 1984-06-19 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives,and pharmaceutical composition containing the same |
| ES2048108B1 (es) * | 1992-07-17 | 1994-10-01 | Lusochimica Spa | Procedimiento para la preparacion de 5-(3-terc-butilamino-2-hidroxipropoxi)-3,4-dihidrocarboestirilo. |
| JP5313125B2 (ja) | 2007-02-28 | 2013-10-09 | 旭化成ファーマ株式会社 | スルホンアミド誘導体 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1058822A (en) * | 1963-07-30 | 1967-02-15 | Ici Ltd | 3-amino-2-hydroxypropoxy heterocyclic derivatives |
| GB1047927A (en) * | 1964-03-09 | 1966-11-09 | Ici Ltd | Alkanolamine derivatives |
| GB1079989A (en) * | 1965-09-28 | 1967-08-16 | Ici Ltd | Carbocyclic propanolamines |
-
1972
- 1972-12-14 JP JP47125857A patent/JPS5239035B2/ja not_active Expired
-
1973
- 1973-12-06 CA CA187,578A patent/CA1022555A/en not_active Expired
- 1973-12-07 DK DK663673AA patent/DK136861B/da not_active IP Right Cessation
- 1973-12-12 AR AR251483A patent/AR197270A1/es active
- 1973-12-13 BE BE138830A patent/BE808593A/xx not_active IP Right Cessation
- 1973-12-13 ES ES421430A patent/ES421430A1/es not_active Expired
- 1973-12-13 NL NL7317090.A patent/NL166931C/xx not_active IP Right Cessation
- 1973-12-14 CH CH1751373A patent/CH589060A5/xx not_active IP Right Cessation
- 1973-12-14 US US05/424,965 patent/US3953456A/en not_active Expired - Lifetime
- 1973-12-14 FR FR7344825A patent/FR2210408B1/fr not_active Expired
- 1973-12-14 DE DE2362278A patent/DE2362278C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5239035B2 (en:Method) | 1977-10-03 |
| NL7317090A (en:Method) | 1974-06-18 |
| DK136861B (da) | 1977-12-05 |
| ES421430A1 (es) | 1976-05-01 |
| AR197270A1 (es) | 1974-03-22 |
| BE808593A (fr) | 1974-03-29 |
| AU6338573A (en) | 1975-07-10 |
| JPS4981372A (en:Method) | 1974-08-06 |
| US3953456A (en) | 1976-04-27 |
| FR2210408B1 (en:Method) | 1977-03-11 |
| CH589060A5 (en:Method) | 1977-06-30 |
| DK136861C (en:Method) | 1978-05-08 |
| FR2210408A1 (en:Method) | 1974-07-12 |
| NL166931C (nl) | 1981-10-15 |
| NL166931B (nl) | 1981-05-15 |
| CA1022555A (en) | 1977-12-13 |
| DE2362278A1 (de) | 1974-06-20 |
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