CS203054B2 - Method of preparing imidazolyl compounds - Google Patents
Method of preparing imidazolyl compounds Download PDFInfo
- Publication number
- CS203054B2 CS203054B2 CS764839A CS483976A CS203054B2 CS 203054 B2 CS203054 B2 CS 203054B2 CS 764839 A CS764839 A CS 764839A CS 483976 A CS483976 A CS 483976A CS 203054 B2 CS203054 B2 CS 203054B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- formula
- compounds
- solution
- reacted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 125000002883 imidazolyl group Chemical group 0.000 title claims description 4
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- OWZZSHUHKDWWIP-UHFFFAOYSA-N 5-(2-aminoethylsulfanylmethyl)-2-methyl-1H-imidazol-4-ol Chemical compound OC=1N=C(NC1CSCCN)C OWZZSHUHKDWWIP-UHFFFAOYSA-N 0.000 abstract 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 abstract 1
- -1 N-methyl-N- [4- (4-imidazolyl) butyl] thiourea Chemical compound 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000001387 anti-histamine Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SODVIWFIWHJBNS-UHFFFAOYSA-N 1H-imidazole dihydrobromide Chemical compound Br.Br.C1=CNC=N1 SODVIWFIWHJBNS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- BJERXDWXCSKSCV-UHFFFAOYSA-N ethyl 5-(ethoxymethyl)-1h-imidazole-4-carboxylate Chemical compound CCOCC=1NC=NC=1C(=O)OCC BJERXDWXCSKSCV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- CJIFBUZRANSSAI-UHFFFAOYSA-N 2-(1h-imidazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CN1 CJIFBUZRANSSAI-UHFFFAOYSA-N 0.000 description 1
- QDDJLZCANXYOEL-UHFFFAOYSA-N 2-[[4-(hydroxymethyl)-1H-imidazol-5-yl]methylsulfanyl]ethylthiourea Chemical compound OCC1=C(N=CN1)CSCCNC(=S)N QDDJLZCANXYOEL-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-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
- SVXQBURXRIUSRP-UHFFFAOYSA-N CCOCC1=CNC(=S)N1 Chemical compound CCOCC1=CNC(=S)N1 SVXQBURXRIUSRP-UHFFFAOYSA-N 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 1
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 1
- 101100273648 Mus musculus Ccna2 gene Proteins 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZOKYZTUQSVAKHS-UHFFFAOYSA-N dimethoxymethylidenecyanamide Chemical compound COC(OC)=NC#N ZOKYZTUQSVAKHS-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- XHTHQRRQGWLZTB-UHFFFAOYSA-N ethyl 5-(ethoxymethyl)-2-sulfanylidene-1,3-dihydroimidazole-4-carboxylate Chemical compound C(C)OC(=O)C=1N=C(NC1COCC)S XHTHQRRQGWLZTB-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31968/75A GB1565647A (en) | 1975-07-31 | 1975-07-31 | Pharmacologically active compounds 4-substituted-imidazole-5-methanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203054B2 true CS203054B2 (en) | 1981-02-27 |
Family
ID=10331071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS764839A CS203054B2 (en) | 1975-07-31 | 1976-07-21 | Method of preparing imidazolyl compounds |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5219663A (en)) |
| AR (1) | AR213100A1 (en)) |
| AT (1) | AT356668B (en)) |
| AU (1) | AU508262B2 (en)) |
| BE (1) | BE843840A (en)) |
| CA (1) | CA1075702A (en)) |
| CS (1) | CS203054B2 (en)) |
| DD (1) | DD125205A5 (en)) |
| DE (1) | DE2634430A1 (en)) |
| DK (1) | DK316376A (en)) |
| ES (1) | ES450309A1 (en)) |
| FI (1) | FI762191A7 (en)) |
| FR (1) | FR2319341A1 (en)) |
| GB (1) | GB1565647A (en)) |
| GR (1) | GR61114B (en)) |
| HU (1) | HU174068B (en)) |
| IL (1) | IL50006A0 (en)) |
| LU (1) | LU75495A1 (en)) |
| NL (1) | NL7608505A (en)) |
| NO (1) | NO762659L (en)) |
| OA (1) | OA05405A (en)) |
| PH (1) | PH13417A (en)) |
| PT (1) | PT65377B (en)) |
| RO (1) | RO72312B (en)) |
| SE (1) | SE7608478L (en)) |
| SU (1) | SU655310A3 (en)) |
| ZA (1) | ZA763686B (en)) |
| ZM (1) | ZM9676A1 (en)) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO781300L (no) | 1977-04-20 | 1978-10-23 | Ici Ltd | Fremgangsmaate for fremstilling av fysiologisk aktive guanidinderivater |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4112234A (en) | 1977-08-22 | 1978-09-05 | Bristol-Myers Company | Imidazolylmethylthioethyl alkynyl guanidines |
| USRE31588E (en) * | 1977-06-03 | 1984-05-22 | Bristol-Myers Company | Imidazolylmethylthioethyl alkynyl guanidines |
| US4233302A (en) | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
| EP0008596A1 (fr) * | 1978-09-04 | 1980-03-19 | DEVINTER Europe S.A. Société anonyme dite: | Procédé de préparation de dérivés du type 4-hydroxyméthyl imidazole à partir d'esters d'acides 4-imidazole carboxyliques correspondants |
| US4200760A (en) * | 1978-09-26 | 1980-04-29 | Bristol-Myers Company | Imidazolylalkylthioalkylamino-ethylene derivatives |
| JPS5914460B2 (ja) * | 1978-12-27 | 1984-04-04 | 相互薬工株式会社 | Ｈ↓２受容体「きつ」抗剤シメチジンの製造法 |
| DE3069889D1 (en) | 1979-01-18 | 1985-02-14 | Ici Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| CN103288742A (zh) * | 2013-06-04 | 2013-09-11 | 四川百利药业有限责任公司 | 一种高纯度英加韦林原料的制备方法 |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA938556A (en) * | 1970-06-25 | 1973-12-18 | Smith Kline And French Laboratories Limited | Pharmaceutical compositions containing thiourea derivatives |
-
1975
- 1975-07-31 GB GB31968/75A patent/GB1565647A/en not_active Expired
-
1976
- 1976-06-21 ZA ZA763686A patent/ZA763686B/xx unknown
- 1976-07-06 BE BE168682A patent/BE843840A/xx not_active IP Right Cessation
- 1976-07-09 PH PH18667A patent/PH13417A/en unknown
- 1976-07-09 IL IL50006A patent/IL50006A0/xx unknown
- 1976-07-13 DK DK316376A patent/DK316376A/da unknown
- 1976-07-16 PT PT65377A patent/PT65377B/pt unknown
- 1976-07-20 FR FR7622069A patent/FR2319341A1/fr active Granted
- 1976-07-21 CS CS764839A patent/CS203054B2/cs unknown
- 1976-07-22 CA CA257,589A patent/CA1075702A/en not_active Expired
- 1976-07-23 ZM ZM96/76A patent/ZM9676A1/xx unknown
- 1976-07-27 SE SE7608478A patent/SE7608478L/xx unknown
- 1976-07-27 GR GR51356A patent/GR61114B/el unknown
- 1976-07-27 AT AT552376A patent/AT356668B/de not_active IP Right Cessation
- 1976-07-29 LU LU75495A patent/LU75495A1/xx unknown
- 1976-07-30 NO NO762659A patent/NO762659L/no unknown
- 1976-07-30 JP JP51092242A patent/JPS5219663A/ja active Pending
- 1976-07-30 ES ES450309A patent/ES450309A1/es not_active Expired
- 1976-07-30 AR AR264157A patent/AR213100A1/es active
- 1976-07-30 HU HU76SI1532A patent/HU174068B/hu unknown
- 1976-07-30 DD DD194154A patent/DD125205A5/xx unknown
- 1976-07-30 FI FI762191A patent/FI762191A7/fi not_active Application Discontinuation
- 1976-07-30 SU SU762386215A patent/SU655310A3/ru active
- 1976-07-30 AU AU16447/76A patent/AU508262B2/en not_active Expired
- 1976-07-30 NL NL7608505A patent/NL7608505A/xx not_active Application Discontinuation
- 1976-07-30 DE DE19762634430 patent/DE2634430A1/de not_active Withdrawn
- 1976-07-31 RO RO87167A patent/RO72312B/ro unknown
- 1976-07-31 OA OA55903A patent/OA05405A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7608505A (nl) | 1977-02-02 |
| NO762659L (en)) | 1977-02-01 |
| PH13417A (en) | 1980-03-30 |
| ES450309A1 (es) | 1977-12-01 |
| HU174068B (hu) | 1979-10-28 |
| GB1565647A (en) | 1980-04-23 |
| ZA763686B (en) | 1977-05-25 |
| AR213100A1 (es) | 1978-12-15 |
| AT356668B (de) | 1980-05-12 |
| JPS5219663A (en) | 1977-02-15 |
| SE7608478L (sv) | 1977-02-01 |
| CA1075702A (en) | 1980-04-15 |
| AU508262B2 (en) | 1980-03-13 |
| IL50006A0 (en) | 1976-09-30 |
| PT65377A (en) | 1976-08-01 |
| GR61114B (en) | 1978-09-13 |
| ATA552376A (de) | 1979-10-15 |
| BE843840A (fr) | 1977-01-06 |
| ZM9676A1 (en) | 1977-07-21 |
| FI762191A7 (en)) | 1977-02-01 |
| SU655310A3 (ru) | 1979-03-30 |
| FR2319341A1 (fr) | 1977-02-25 |
| RO72312B (ro) | 1984-03-31 |
| OA05405A (fr) | 1981-02-28 |
| DK316376A (da) | 1977-02-01 |
| RO72312A (ro) | 1984-03-15 |
| LU75495A1 (en)) | 1977-03-03 |
| PT65377B (en) | 1978-01-19 |
| DE2634430A1 (de) | 1977-02-10 |
| DD125205A5 (en)) | 1977-04-06 |
| AU1644776A (en) | 1978-02-02 |
| FR2319341B1 (en)) | 1979-01-12 |
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