CH508637A - Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline - Google Patents
Verfahren zur Herstellung neuer, halogensubstituierter TetrahydrochinazolineInfo
- Publication number
- CH508637A CH508637A CH895370A CH895370A CH508637A CH 508637 A CH508637 A CH 508637A CH 895370 A CH895370 A CH 895370A CH 895370 A CH895370 A CH 895370A CH 508637 A CH508637 A CH 508637A
- Authority
- CH
- Switzerland
- Prior art keywords
- chlorine
- inorganic
- hydrogen
- formula
- organic acids
- Prior art date
Links
- 230000001754 anti-pyretic effect Effects 0.000 title abstract description 3
- 239000002221 antipyretic Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
- 150000007524 organic acids Chemical class 0.000 claims abstract description 5
- 235000005985 organic acids Nutrition 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical class C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- -1 aralkyl radical Chemical class 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims 1
- AJOQVCHLLULVGK-HAQNSBGRSA-N C1C[C@@H](O)CC[C@@H]1N1CC2=CC(Br)=CC(Br)=C2NC1 Chemical compound C1C[C@@H](O)CC[C@@H]1N1CC2=CC(Br)=CC(Br)=C2NC1 AJOQVCHLLULVGK-HAQNSBGRSA-N 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 206010011224 Cough Diseases 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- UZVFOBCSRACABZ-UHFFFAOYSA-N 6-chloro-3-cyclohexyl-2,4-dihydro-1H-quinazoline Chemical compound ClC=1C=C2CN(CNC2=CC1)C1CCCCC1 UZVFOBCSRACABZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZQMASBWYHYABMJ-NWDGAFQWSA-N (1R,3S)-3-(6,8-dibromo-2,4-dihydro-1H-quinazolin-3-yl)cyclohexan-1-ol Chemical compound BrC=1C=C2CN(CNC2=C(C1)Br)[C@@H]1C[C@@H](CCC1)O ZQMASBWYHYABMJ-NWDGAFQWSA-N 0.000 description 1
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 1
- WBDGOIMOYXCYHI-UHFFFAOYSA-N 2-methyl-1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NC(C)NCC2=C1 WBDGOIMOYXCYHI-UHFFFAOYSA-N 0.000 description 1
- WMQSKECCMQRJRX-UHFFFAOYSA-N 2-methyl-3,1-benzoxazin-4-one Chemical class C1=CC=C2C(=O)OC(C)=NC2=C1 WMQSKECCMQRJRX-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SWRCDJRBDHNBAF-UHFFFAOYSA-N 3-benzyl-6-chloro-2,4-dihydro-1H-quinazoline Chemical compound ClC=1C=C2CN(CNC2=CC1)CC1=CC=CC=C1 SWRCDJRBDHNBAF-UHFFFAOYSA-N 0.000 description 1
- HSGGWUGAVYTADI-UHFFFAOYSA-N 5-chloro-n-cyclohexyl-2-(methylamino)benzamide Chemical compound CNC1=CC=C(Cl)C=C1C(=O)NC1CCCCC1 HSGGWUGAVYTADI-UHFFFAOYSA-N 0.000 description 1
- RNPDORPZTWKTAF-UHFFFAOYSA-N 6-chloro-3-(2-methylpropyl)-2,4-dihydro-1H-quinazoline Chemical compound ClC=1C=C2CN(CNC2=CC1)CC(C)C RNPDORPZTWKTAF-UHFFFAOYSA-N 0.000 description 1
- ZQMASBWYHYABMJ-RYUDHWBXSA-N BrC=1C=C2CN(CNC2=C(C1)Br)[C@@H]1C[C@H](CCC1)O Chemical compound BrC=1C=C2CN(CNC2=C(C1)Br)[C@@H]1C[C@H](CCC1)O ZQMASBWYHYABMJ-RYUDHWBXSA-N 0.000 description 1
- HCPOTMGUGUQVOY-UHFFFAOYSA-N CCN(CC)CCN(CNCC1=CC(Br)=C2)C1=C2Br Chemical compound CCN(CC)CCN(CNCC1=CC(Br)=C2)C1=C2Br HCPOTMGUGUQVOY-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET0030948 | 1966-04-20 | ||
| CH1648169A CH493531A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH508637A true CH508637A (de) | 1971-06-15 |
Family
ID=36887743
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH895370A CH508637A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
| CH1648369A CH493533A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
| CH483567A CH483433A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
| CH1648169A CH493531A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
| CH1648269A CH493532A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1648369A CH493533A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
| CH483567A CH483433A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
| CH1648169A CH493531A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
| CH1648269A CH493532A (de) | 1966-04-20 | 1967-04-06 | Verfahren zur Herstellung neuer, halogensubstituierter Tetrahydrochinazoline |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3454574A (2) |
| BE (1) | BE697188A (2) |
| CH (5) | CH508637A (2) |
| CS (1) | CS162434B1 (2) |
| DE (1) | DE1620541C3 (2) |
| DK (1) | DK120345B (2) |
| ES (4) | ES339371A1 (2) |
| FI (1) | FI48929C (2) |
| FR (2) | FR6442M (2) |
| GB (1) | GB1131164A (2) |
| GR (1) | GR33644B (2) |
| IL (1) | IL27764A (2) |
| NL (2) | NL6705206A (2) |
| SE (1) | SE323685B (2) |
| YU (4) | YU32364B (2) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5924990B2 (ja) * | 1979-11-21 | 1984-06-13 | 協和醗酵工業株式会社 | 新規なピペリジン誘導体 |
| US4753944A (en) * | 1985-11-04 | 1988-06-28 | American Cyanamid Company | Pharmaceutical methods of using 3-heteroarylalkyl-4-quinazolinones |
| US4710502A (en) * | 1985-11-04 | 1987-12-01 | American Cyanamid Company | 3-heteroarylalkyl-4-quinazolinones |
| CS272018B1 (en) * | 1988-11-01 | 1990-12-13 | Fisnerova Ludmila | Ethereal derivatives of 4/3h/-quinazolinone |
| BRPI0413347A (pt) | 2003-08-06 | 2006-10-10 | Senomyx Inc | novos sabores, modificadores de sabor, agentes de sabor, realçadores de sabor, agentes de sabor e/ou realçadores umami ou doces, e utilização correspondente |
| KR101387563B1 (ko) | 2006-04-21 | 2014-04-25 | 세노믹스, 인코포레이티드 | 고효능의 조미용 향료를 포함하는 식품 조성물 및 이의 제조 방법 |
| CN102898383A (zh) * | 2012-11-16 | 2013-01-30 | 葛长乐 | 一种氨溴索反式杂质6,8-二溴-3-(反式-4-羟基环己基)-1,2,3,4-四氢喹唑啉的制备方法 |
-
0
- NL NL131479D patent/NL131479C/xx active
-
1966
- 1966-04-20 DE DE1620541A patent/DE1620541C3/de not_active Expired
-
1967
- 1967-03-30 DK DK173367AA patent/DK120345B/da unknown
- 1967-04-06 CH CH895370A patent/CH508637A/de not_active IP Right Cessation
- 1967-04-06 CH CH1648369A patent/CH493533A/de not_active IP Right Cessation
- 1967-04-06 CH CH483567A patent/CH483433A/de not_active IP Right Cessation
- 1967-04-06 CH CH1648169A patent/CH493531A/de not_active IP Right Cessation
- 1967-04-06 CH CH1648269A patent/CH493532A/de not_active IP Right Cessation
- 1967-04-10 IL IL27764A patent/IL27764A/en unknown
- 1967-04-10 US US629417A patent/US3454574A/en not_active Expired - Lifetime
- 1967-04-13 NL NL6705206A patent/NL6705206A/xx unknown
- 1967-04-13 GB GB17098/67A patent/GB1131164A/en not_active Expired
- 1967-04-15 YU YU0756/67A patent/YU32364B/xx unknown
- 1967-04-15 ES ES339371A patent/ES339371A1/es not_active Expired
- 1967-04-17 ES ES339394A patent/ES339394A1/es not_active Expired
- 1967-04-18 ES ES339432A patent/ES339432A1/es not_active Expired
- 1967-04-18 BE BE697188D patent/BE697188A/xx unknown
- 1967-04-18 FR FR103182A patent/FR6442M/fr not_active Expired
- 1967-04-18 FR FR103183A patent/FR1524445A/fr not_active Expired
- 1967-04-19 ES ES339483A patent/ES339483A1/es not_active Expired
- 1967-04-19 GR GR670133644A patent/GR33644B/el unknown
- 1967-04-20 SE SE5557/67A patent/SE323685B/xx unknown
- 1967-04-20 FI FI671165A patent/FI48929C/fi active
-
1968
- 1968-09-25 CS CS6704A patent/CS162434B1/cs unknown
-
1973
- 1973-03-19 YU YU740/73A patent/YU35360B/xx unknown
- 1973-03-19 YU YU742/73A patent/YU33957B/xx unknown
- 1973-03-19 YU YU74173A patent/YU35587B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES339394A1 (es) | 1968-07-16 |
| FR6442M (2) | 1968-11-12 |
| YU74173A (en) | 1980-09-25 |
| ES339371A1 (es) | 1968-07-16 |
| IL27764A (en) | 1971-02-25 |
| GB1131164A (en) | 1968-10-23 |
| YU74073A (en) | 1980-06-30 |
| YU32364B (en) | 1974-10-31 |
| CH493531A (de) | 1970-07-15 |
| US3454574A (en) | 1969-07-08 |
| BE697188A (2) | 1967-10-18 |
| ES339483A1 (es) | 1968-07-16 |
| YU35587B (en) | 1981-04-30 |
| FI48929C (fi) | 1975-02-10 |
| NL131479C (2) | |
| YU74273A (en) | 1978-02-28 |
| GR33644B (el) | 1968-01-03 |
| CH483433A (de) | 1969-12-31 |
| CH493533A (de) | 1970-07-15 |
| ES339432A1 (es) | 1968-07-16 |
| CS162434B1 (2) | 1975-07-15 |
| DK120345B (da) | 1971-05-17 |
| YU75667A (en) | 1974-04-30 |
| FI48929B (2) | 1974-10-31 |
| DE1620541C3 (de) | 1975-09-25 |
| NL6705206A (2) | 1967-10-23 |
| DE1620541A1 (de) | 1970-04-16 |
| SE323685B (2) | 1970-05-11 |
| CH493532A (de) | 1970-07-15 |
| YU35360B (en) | 1980-12-31 |
| FR1524445A (fr) | 1968-05-10 |
| YU33957B (en) | 1978-09-08 |
| DE1620541B2 (de) | 1975-02-20 |
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