SE454987B - Acylerade 1,2,4-triazol-derivat, forfarande for framstellning derav och virostatiska lekemedelspreparat innehallande 1,2,4-triazolderivaten - Google Patents
Acylerade 1,2,4-triazol-derivat, forfarande for framstellning derav och virostatiska lekemedelspreparat innehallande 1,2,4-triazolderivatenInfo
- Publication number
- SE454987B SE454987B SE8304715A SE8304715A SE454987B SE 454987 B SE454987 B SE 454987B SE 8304715 A SE8304715 A SE 8304715A SE 8304715 A SE8304715 A SE 8304715A SE 454987 B SE454987 B SE 454987B
- Authority
- SE
- Sweden
- Prior art keywords
- compounds
- general formula
- methyl
- carbon atoms
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 230000001790 virustatic effect Effects 0.000 title claims description 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title claims 4
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- -1 hydroxy, amino- Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 230000008707 rearrangement Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- 239000000203 mixture Substances 0.000 description 12
- 241000700605 Viruses Species 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XGWWZKBCQLBJNH-UHFFFAOYSA-N 3-methylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound CSC1=NN=C(N)N1 XGWWZKBCQLBJNH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004113 cell culture Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 5
- 241000712079 Measles morbillivirus Species 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 230000035755 proliferation Effects 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- ANCYIKYMJVRRJH-UHFFFAOYSA-N (5-amino-3-methylsulfanyl-1,2,4-triazol-1-yl)-(2-methylphenyl)methanone Chemical compound N1=C(SC)N=C(N)N1C(=O)C1=CC=CC=C1C ANCYIKYMJVRRJH-UHFFFAOYSA-N 0.000 description 2
- AZAUSLJPGDVATA-UHFFFAOYSA-N 2-methyl-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)C)=N1 AZAUSLJPGDVATA-UHFFFAOYSA-N 0.000 description 2
- 102100024940 Cathepsin K Human genes 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 101000761509 Homo sapiens Cathepsin K Proteins 0.000 description 2
- 101000740970 Homo sapiens Cathepsin O Proteins 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000007541 cellular toxicity Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000712461 unidentified influenza virus Species 0.000 description 2
- RDAJAIIWUXPLPB-UHFFFAOYSA-N (5-amino-3-methylsulfanyl-1,2,4-triazol-1-yl)-(4-chlorophenyl)methanone Chemical compound N1=C(SC)N=C(N)N1C(=O)C1=CC=C(Cl)C=C1 RDAJAIIWUXPLPB-UHFFFAOYSA-N 0.000 description 1
- WAWCVJQGMFGSOH-UHFFFAOYSA-N (5-amino-3-methylsulfanyl-1,2,4-triazol-1-yl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(N)=NC(SC)=N1 WAWCVJQGMFGSOH-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- UCDUHAURQVKFJE-UHFFFAOYSA-N 2-bromo-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)Br)=N1 UCDUHAURQVKFJE-UHFFFAOYSA-N 0.000 description 1
- DCFOYOSOUSTEAG-UHFFFAOYSA-N 2-chloro-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)Cl)=N1 DCFOYOSOUSTEAG-UHFFFAOYSA-N 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- DZCLOAYHWVZIHH-UHFFFAOYSA-N 2-hydroxy-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)O)=N1 DZCLOAYHWVZIHH-UHFFFAOYSA-N 0.000 description 1
- APJVLEWAJUWHQH-UHFFFAOYSA-N 2-methyl-n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)benzenecarbothioamide Chemical compound CSC1=NNC(NC(=S)C=2C(=CC=CC=2)C)=N1 APJVLEWAJUWHQH-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
- 108700028369 Alleles Proteins 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 101001007415 Homo sapiens LEM domain-containing protein 1 Proteins 0.000 description 1
- 241001135569 Human adenovirus 5 Species 0.000 description 1
- 102100028300 LEM domain-containing protein 1 Human genes 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000035931 haemagglutination Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000002941 microtiter virus yield reduction assay Methods 0.000 description 1
- HUDLSVXTUBASBN-UHFFFAOYSA-N n-(3-ethylsulfanyl-1h-1,2,4-triazol-5-yl)-2-methylbenzamide Chemical compound CCSC1=NNC(NC(=O)C=2C(=CC=CC=2)C)=N1 HUDLSVXTUBASBN-UHFFFAOYSA-N 0.000 description 1
- ZTJAGNZJYVNBSD-UHFFFAOYSA-N n-(3-methylsulfanyl-1h-1,2,4-triazol-5-yl)-2-nitrobenzamide Chemical compound CSC1=NNC(NC(=O)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 ZTJAGNZJYVNBSD-UHFFFAOYSA-N 0.000 description 1
- 231100000065 noncytotoxic Toxicity 0.000 description 1
- 230000002020 noncytotoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU822797A HU191475B (en) | 1982-09-01 | 1982-09-01 | Process for producing new acylized 1,2,4-triazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8304715D0 SE8304715D0 (sv) | 1983-08-31 |
| SE8304715L SE8304715L (sv) | 1984-03-02 |
| SE454987B true SE454987B (sv) | 1988-06-13 |
Family
ID=10961139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8304715A SE454987B (sv) | 1982-09-01 | 1983-08-31 | Acylerade 1,2,4-triazol-derivat, forfarande for framstellning derav och virostatiska lekemedelspreparat innehallande 1,2,4-triazolderivaten |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4537899A (de) |
| JP (1) | JPS5993063A (de) |
| AT (1) | AT384425B (de) |
| BE (1) | BE897607A (de) |
| CH (1) | CH655105A5 (de) |
| DE (1) | DE3331591A1 (de) |
| FR (1) | FR2532311B1 (de) |
| GB (1) | GB2130200B (de) |
| HU (1) | HU191475B (de) |
| NL (1) | NL8303032A (de) |
| SE (1) | SE454987B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60239362A (ja) * | 1982-12-16 | 1985-11-28 | アルミニウム カンパニ− オブ アメリカ | ベ−タシリコンアルミニウムオキシナイトライド耐火材料を製造する方法 |
| JP2003510359A (ja) * | 1999-10-01 | 2003-03-18 | スミスクライン・ビーチャム・コーポレイション | 化合物および方法 |
| KR100849021B1 (ko) | 2007-06-19 | 2008-07-29 | (주)더페이스샵코리아 | 카페익산 유도체 및 이를 함유하는 조성물 |
| US9056867B2 (en) | 2011-09-16 | 2015-06-16 | Novartis Ag | N-substituted heterocyclyl carboxamides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD113362A1 (de) * | 1974-02-07 | 1975-06-05 | ||
| JPS5559463A (en) * | 1978-10-30 | 1980-05-02 | Konishiroku Photo Ind Co Ltd | Color photographic material |
| MA19269A1 (fr) * | 1980-09-16 | 1982-04-01 | Lilly Co Eli | Perfectionnement relatif a des derives de n-arylbenzamides . |
-
1982
- 1982-09-01 HU HU822797A patent/HU191475B/hu not_active IP Right Cessation
-
1983
- 1983-08-25 US US06/526,694 patent/US4537899A/en not_active Expired - Fee Related
- 1983-08-29 BE BE1010858A patent/BE897607A/fr unknown
- 1983-08-31 FR FR838313963A patent/FR2532311B1/fr not_active Expired - Lifetime
- 1983-08-31 JP JP58158128A patent/JPS5993063A/ja active Pending
- 1983-08-31 SE SE8304715A patent/SE454987B/sv not_active IP Right Cessation
- 1983-08-31 NL NL8303032A patent/NL8303032A/nl not_active Application Discontinuation
- 1983-08-31 AT AT0311083A patent/AT384425B/de not_active IP Right Cessation
- 1983-08-31 CH CH4765/83A patent/CH655105A5/de not_active IP Right Cessation
- 1983-09-01 GB GB08323422A patent/GB2130200B/en not_active Expired
- 1983-09-01 DE DE3331591A patent/DE3331591A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| NL8303032A (nl) | 1984-04-02 |
| GB2130200B (en) | 1986-05-08 |
| GB2130200A (en) | 1984-05-31 |
| AT384425B (de) | 1987-11-10 |
| HU191475B (en) | 1987-02-27 |
| SE8304715L (sv) | 1984-03-02 |
| CH655105A5 (de) | 1986-03-27 |
| ATA311083A (de) | 1987-04-15 |
| GB8323422D0 (en) | 1983-10-05 |
| JPS5993063A (ja) | 1984-05-29 |
| US4537899A (en) | 1985-08-27 |
| BE897607A (fr) | 1984-02-29 |
| FR2532311A1 (fr) | 1984-03-02 |
| SE8304715D0 (sv) | 1983-08-31 |
| FR2532311B1 (fr) | 1990-05-11 |
| DE3331591A1 (de) | 1984-03-01 |
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