FI58493C - Analogifoerfarande foer framstaellning av terapeutiskt aktiva tiokarbaminsyraderivat - Google Patents
Analogifoerfarande foer framstaellning av terapeutiskt aktiva tiokarbaminsyraderivat Download PDFInfo
- Publication number
- FI58493C FI58493C FI854/73A FI85473A FI58493C FI 58493 C FI58493 C FI 58493C FI 854/73 A FI854/73 A FI 854/73A FI 85473 A FI85473 A FI 85473A FI 58493 C FI58493 C FI 58493C
- Authority
- FI
- Finland
- Prior art keywords
- group
- general formula
- tetrahydro
- compound
- formula
- Prior art date
Links
- 230000000694 effects Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 12
- -1 5,6,7,8-tetrahydro-2-naphthyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052751 metal Chemical group 0.000 claims description 2
- 239000002184 metal Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 11
- 229960004880 tolnaftate Drugs 0.000 description 11
- 206010061218 Inflammation Diseases 0.000 description 7
- 230000004054 inflammatory process Effects 0.000 description 7
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- FBGJJTQNZVNEQU-UHFFFAOYSA-N n,3-dimethylaniline Chemical compound CNC1=CC=CC(C)=C1 FBGJJTQNZVNEQU-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000223238 Trichophyton Species 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241001480035 Epidermophyton Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- NKAAEMMYHLFEFN-UHFFFAOYSA-M monosodium tartrate Chemical class [Na+].OC(=O)C(O)C(O)C([O-])=O NKAAEMMYHLFEFN-UHFFFAOYSA-M 0.000 description 1
- WAZUROKOCYSLSU-UHFFFAOYSA-N n-methyl-n-(3-methylphenyl)carbamothioyl chloride Chemical compound ClC(=S)N(C)C1=CC=CC(C)=C1 WAZUROKOCYSLSU-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005316 response function Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
- C07C333/08—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- 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
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2210272 | 1972-03-20 | ||
| IT2210272 | 1972-03-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58493B FI58493B (fi) | 1980-10-31 |
| FI58493C true FI58493C (fi) | 1981-02-10 |
Family
ID=11191518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI854/73A FI58493C (fi) | 1972-03-20 | 1973-03-20 | Analogifoerfarande foer framstaellning av terapeutiskt aktiva tiokarbaminsyraderivat |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3855263A (xx) |
| JP (1) | JPS528306B2 (xx) |
| AT (1) | AT320664B (xx) |
| AU (1) | AU472832B2 (xx) |
| BE (1) | BE796895A (xx) |
| CA (1) | CA988939A (xx) |
| CH (1) | CH581616A5 (xx) |
| DK (1) | DK134485B (xx) |
| ES (1) | ES412766A1 (xx) |
| FI (1) | FI58493C (xx) |
| FR (1) | FR2181835B1 (xx) |
| GB (1) | GB1364407A (xx) |
| HK (1) | HK54476A (xx) |
| IE (1) | IE37573B1 (xx) |
| IL (1) | IL41811A (xx) |
| KE (1) | KE2655A (xx) |
| MY (1) | MY7600270A (xx) |
| NL (1) | NL148883B (xx) |
| NO (1) | NO130539C (xx) |
| PH (1) | PH9599A (xx) |
| SE (1) | SE393801B (xx) |
| YU (1) | YU39705B (xx) |
| ZA (1) | ZA731497B (xx) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4136020A (en) * | 1976-11-11 | 1979-01-23 | Minerec Corporation | Flotation reagent and process |
| US4348407A (en) * | 1981-04-29 | 1982-09-07 | Adria Laboratories, Inc. | Orally active tolciclate and tolnaftate |
| US4554012A (en) * | 1982-06-10 | 1985-11-19 | Toyo Soda Manufacturing Co., Ltd. | Aryl N-alkyl-N-(pyridyl or pyrimidyl) carbamate |
| BR8303320A (pt) * | 1982-06-23 | 1984-02-07 | Toyo Soda Mfg Co Ltd | Composicao herbicida |
| US4605668A (en) * | 1983-05-17 | 1986-08-12 | Sumitomo Chemical Company, Limited | Fungicidal carbamate compounds |
| JPS6058916A (ja) * | 1983-09-13 | 1985-04-05 | Toyo Soda Mfg Co Ltd | 抗真菌剤 |
| USRE32145E (en) * | 1984-11-05 | 1986-05-13 | Hercules Incorporated | Orally active tolciclate .[.(and tolnaftate).]. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1337797A (fr) * | 1961-06-21 | 1963-09-20 | Nippon Soda Co | Procédé de fabrication de thionocarbamates d'aryle substitués à l'azote et les thionocarbamates conformes à ceux obtenus par le présent procédé ou procédé simi laire |
| US3334126A (en) * | 1961-06-21 | 1967-08-01 | Nippon Soda Co | Aryl n-methyl substituted thionocarbamates |
| US3334116A (en) * | 1964-06-08 | 1967-08-01 | Martin Marietta Corp | Phthalocyanine dyestuffs |
| FR2081575A1 (en) * | 1970-03-13 | 1971-12-10 | Squibb & Sons Inc | Indane thiocarbamic esters |
-
1973
- 1973-03-05 ZA ZA731497A patent/ZA731497B/xx unknown
- 1973-03-07 AU AU53070/73A patent/AU472832B2/en not_active Expired
- 1973-03-09 IE IE394/73A patent/IE37573B1/xx unknown
- 1973-03-12 YU YU644/73A patent/YU39705B/xx unknown
- 1973-03-13 US US00340932A patent/US3855263A/en not_active Expired - Lifetime
- 1973-03-15 AT AT231173A patent/AT320664B/de not_active IP Right Cessation
- 1973-03-16 NL NL737303735A patent/NL148883B/xx not_active IP Right Cessation
- 1973-03-16 GB GB1268773A patent/GB1364407A/en not_active Expired
- 1973-03-16 BE BE128896A patent/BE796895A/xx not_active IP Right Cessation
- 1973-03-16 DK DK143673AA patent/DK134485B/da unknown
- 1973-03-17 ES ES412766A patent/ES412766A1/es not_active Expired
- 1973-03-19 CH CH396773A patent/CH581616A5/xx not_active IP Right Cessation
- 1973-03-19 CA CA166,408A patent/CA988939A/en not_active Expired
- 1973-03-19 NO NO1108/73A patent/NO130539C/no unknown
- 1973-03-19 IL IL41811A patent/IL41811A/en unknown
- 1973-03-19 SE SE7303779A patent/SE393801B/xx unknown
- 1973-03-20 FR FR7309993A patent/FR2181835B1/fr not_active Expired
- 1973-03-20 PH PH14448*UA patent/PH9599A/en unknown
- 1973-03-20 JP JP48032572A patent/JPS528306B2/ja not_active Expired
- 1973-03-20 FI FI854/73A patent/FI58493C/fi active
-
1976
- 1976-08-10 KE KE2655*UA patent/KE2655A/xx unknown
- 1976-09-02 HK HK544/76*UA patent/HK54476A/xx unknown
- 1976-12-30 MY MY270/76A patent/MY7600270A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2313845B2 (de) | 1975-10-30 |
| ES412766A1 (es) | 1976-03-16 |
| CA988939A (en) | 1976-05-11 |
| IL41811A (en) | 1976-01-30 |
| IE37573B1 (en) | 1977-08-31 |
| IE37573L (en) | 1973-09-20 |
| NL7303735A (xx) | 1973-09-24 |
| JPS528306B2 (xx) | 1977-03-08 |
| NO130539B (xx) | 1974-09-23 |
| ZA731497B (en) | 1973-12-19 |
| YU64473A (en) | 1982-02-28 |
| BE796895A (fr) | 1973-07-16 |
| KE2655A (en) | 1976-08-20 |
| NL148883B (nl) | 1976-03-15 |
| AU472832B2 (en) | 1976-06-03 |
| JPS495955A (xx) | 1974-01-19 |
| AU5307073A (en) | 1974-09-12 |
| HK54476A (en) | 1976-09-10 |
| PH9599A (en) | 1976-01-19 |
| FI58493B (fi) | 1980-10-31 |
| SE393801B (sv) | 1977-05-23 |
| CH581616A5 (xx) | 1976-11-15 |
| YU39705B (en) | 1985-04-30 |
| AT320664B (de) | 1975-02-25 |
| NO130539C (xx) | 1975-01-02 |
| MY7600270A (en) | 1976-12-31 |
| FR2181835A1 (xx) | 1973-12-07 |
| DK134485C (xx) | 1977-04-18 |
| IL41811A0 (en) | 1973-05-31 |
| US3855263A (en) | 1974-12-17 |
| DE2313845A1 (de) | 1973-10-18 |
| FR2181835B1 (xx) | 1976-05-14 |
| DK134485B (da) | 1976-11-15 |
| GB1364407A (en) | 1974-08-21 |
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