CA1129412A - Process for the preparation of imidazo-and pyrimido-pyridoindoles - Google Patents
Process for the preparation of imidazo-and pyrimido-pyridoindolesInfo
- Publication number
- CA1129412A CA1129412A CA343,699A CA343699A CA1129412A CA 1129412 A CA1129412 A CA 1129412A CA 343699 A CA343699 A CA 343699A CA 1129412 A CA1129412 A CA 1129412A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- formula
- alkyl
- compound
- derivatives
- 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
- REDWVXCYDSLNMN-UHFFFAOYSA-N C1=NC=NC2=CC3=C(NC=C4)C4=CC=C3N=C21 Chemical class C1=NC=NC2=CC3=C(NC=C4)C4=CC=C3N=C21 REDWVXCYDSLNMN-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 20
- 230000008569 process Effects 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- -1 alkoxy radical Chemical class 0.000 claims abstract description 30
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 8
- 239000012458 free base Substances 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 abstract description 3
- 206010010904 Convulsion Diseases 0.000 abstract description 2
- 230000036461 convulsion Effects 0.000 abstract description 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229960004279 formaldehyde Drugs 0.000 description 4
- 235000019256 formaldehyde Nutrition 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- RBHDFGBPJGEYCK-UHFFFAOYSA-N 2-(5-methyl-1h-indol-3-yl)ethylazanium;chloride Chemical compound Cl.CC1=CC=C2NC=C(CCN)C2=C1 RBHDFGBPJGEYCK-UHFFFAOYSA-N 0.000 description 1
- IKGHURAEQOXMHK-UHFFFAOYSA-N 2-(9h-pyrido[3,4-b]indol-2-ium-1-yl)acetate Chemical compound C12=CC=CC=C2NC2=C1C=CN=C2CC(=O)O IKGHURAEQOXMHK-UHFFFAOYSA-N 0.000 description 1
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- CJWIZJLFHYLSDT-UHFFFAOYSA-N N-methyl-2-(1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-yl)acetamide Chemical compound CNC(CC1(NCCC2=C1NC1=CC=CC=C21)C)=O CJWIZJLFHYLSDT-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 1
- JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- TWLQNEMSPNGMFK-UHFFFAOYSA-N ethyl 1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-1-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C(C(=O)OCC)(C)NCC2 TWLQNEMSPNGMFK-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- DUWIGDFPHOOAHN-UHFFFAOYSA-N n,1-dimethyl-2,3,4,9-tetrahydropyrido[3,4-b]indole-1-carboxamide Chemical compound N1C2=CC=CC=C2C2=C1C(C(=O)NC)(C)NCC2 DUWIGDFPHOOAHN-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7902839 | 1979-02-05 | ||
| FR7902839A FR2447921A1 (fr) | 1979-02-05 | 1979-02-05 | Imidazo et pyrimido-pyrido-indoles et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1129412A true CA1129412A (en) | 1982-08-10 |
Family
ID=9221588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA343,699A Expired CA1129412A (en) | 1979-02-05 | 1980-01-15 | Process for the preparation of imidazo-and pyrimido-pyridoindoles |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0015786B1 (enExample) |
| JP (1) | JPS55104282A (enExample) |
| AT (1) | ATE878T1 (enExample) |
| AU (1) | AU528425B2 (enExample) |
| CA (1) | CA1129412A (enExample) |
| DE (1) | DE3060292D1 (enExample) |
| DK (1) | DK17080A (enExample) |
| ES (1) | ES487712A1 (enExample) |
| FR (1) | FR2447921A1 (enExample) |
| GR (1) | GR74450B (enExample) |
| IE (1) | IE49629B1 (enExample) |
| IL (1) | IL59127A (enExample) |
| NO (1) | NO151289C (enExample) |
| PT (1) | PT70697A (enExample) |
| ZA (1) | ZA80241B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2485538B1 (fr) * | 1980-06-24 | 1985-01-11 | Chinoin Gyogyszer Es Vegyeszet | Nouveau procede de preparation d'indolo(2',3';3,4)-pyrido(1,2-b)quinazoline-5-ones |
| DE3827727A1 (de) * | 1988-08-16 | 1990-02-22 | Boehringer Ingelheim Kg | Anellierte tetrahydropyridinessigsaeurederivate, verfahren zu deren herstellung und verwendung solcher verbindungen zur kardioprotektion |
-
1979
- 1979-02-05 FR FR7902839A patent/FR2447921A1/fr active Granted
- 1979-12-27 NO NO794270A patent/NO151289C/no unknown
-
1980
- 1980-01-14 JP JP300280A patent/JPS55104282A/ja active Granted
- 1980-01-15 DE DE8080400049T patent/DE3060292D1/de not_active Expired
- 1980-01-15 AU AU54629/80A patent/AU528425B2/en not_active Ceased
- 1980-01-15 ZA ZA00800241A patent/ZA80241B/xx unknown
- 1980-01-15 AT AT80400049T patent/ATE878T1/de active
- 1980-01-15 EP EP80400049A patent/EP0015786B1/fr not_active Expired
- 1980-01-15 CA CA343,699A patent/CA1129412A/en not_active Expired
- 1980-01-15 DK DK17080A patent/DK17080A/da not_active Application Discontinuation
- 1980-01-15 ES ES487712A patent/ES487712A1/es not_active Expired
- 1980-01-15 IL IL59127A patent/IL59127A/xx unknown
- 1980-01-15 GR GR60961A patent/GR74450B/el unknown
- 1980-01-15 PT PT70697A patent/PT70697A/pt unknown
- 1980-01-15 IE IE77/80A patent/IE49629B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA80241B (en) | 1980-12-31 |
| PT70697A (fr) | 1980-02-01 |
| NO794270L (no) | 1980-08-06 |
| AU528425B2 (en) | 1983-04-28 |
| ATE878T1 (de) | 1982-05-15 |
| IL59127A0 (en) | 1980-05-30 |
| FR2447921A1 (fr) | 1980-08-29 |
| ES487712A1 (es) | 1980-06-16 |
| EP0015786B1 (fr) | 1982-04-21 |
| IL59127A (en) | 1983-12-30 |
| DK17080A (da) | 1980-08-06 |
| IE49629B1 (en) | 1985-11-13 |
| JPS616073B2 (enExample) | 1986-02-24 |
| JPS55104282A (en) | 1980-08-09 |
| FR2447921B1 (enExample) | 1982-01-29 |
| DE3060292D1 (en) | 1982-06-03 |
| NO151289C (no) | 1985-03-13 |
| NO151289B (no) | 1984-12-03 |
| AU5462980A (en) | 1980-08-14 |
| GR74450B (enExample) | 1984-06-28 |
| IE800077L (en) | 1980-08-05 |
| EP0015786A1 (fr) | 1980-09-17 |
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