SU691094A3 - Способ получени цефалоспорановых соединений или их эфиров или их солей - Google Patents
Способ получени цефалоспорановых соединений или их эфиров или их солейInfo
- Publication number
- SU691094A3 SU691094A3 SU752170664A SU2170664A SU691094A3 SU 691094 A3 SU691094 A3 SU 691094A3 SU 752170664 A SU752170664 A SU 752170664A SU 2170664 A SU2170664 A SU 2170664A SU 691094 A3 SU691094 A3 SU 691094A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- solution
- water
- mol
- added
- mixture
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims 3
- 150000002148 esters Chemical class 0.000 title claims 2
- 239000000243 solution Substances 0.000 claims description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 21
- -1 2-aminomethylphenylacetamido Chemical group 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 14
- 239000002244 precipitate Substances 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 8
- 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 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003610 charcoal Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical group 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000003518 caustics Substances 0.000 claims 2
- 239000002510 pyrogen Substances 0.000 claims 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims 2
- CUGNJQBWXZTHFQ-UHFFFAOYSA-N 2-cyclohexa-1,3-dien-1-ylacetic acid Chemical compound OC(=O)CC1=CC=CCC1 CUGNJQBWXZTHFQ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical group NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 claims 1
- MNEIPOIFQCXXGM-UHFFFAOYSA-M O.O.O.[OH-].[Na+] Chemical compound O.O.O.[OH-].[Na+] MNEIPOIFQCXXGM-UHFFFAOYSA-M 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- 244000144980 herd Species 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 claims 1
- 239000008174 sterile solution Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- SLAYUXIURFNXPG-KPMSDPLLSA-N (6r)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NCC1=CC=CC=C1CC(=O)NC1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)CC(O)=O)CS[C@@H]21 SLAYUXIURFNXPG-KPMSDPLLSA-N 0.000 description 1
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 206010051602 Laziness Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 241000860832 Yoda Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QMMZKDAXYSETFV-UHFFFAOYSA-N furan-2-carbonyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CO1 QMMZKDAXYSETFV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered 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
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by 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)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50299174A | 1974-09-03 | 1974-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU691094A3 true SU691094A3 (ru) | 1979-10-05 |
Family
ID=24000311
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752170664A SU691094A3 (ru) | 1974-09-03 | 1975-09-03 | Способ получени цефалоспорановых соединений или их эфиров или их солей |
| SU762388313A SU685157A3 (ru) | 1974-09-03 | 1976-08-10 | Способ получени 7-амино-3-/ (1-карбоксиметилтетразол-5-ил)тисметил/-3-пефем-4-карбоновой кислоты |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762388313A SU685157A3 (ru) | 1974-09-03 | 1976-08-10 | Способ получени 7-амино-3-/ (1-карбоксиметилтетразол-5-ил)тисметил/-3-пефем-4-карбоновой кислоты |
Country Status (14)
| Country | Link |
|---|---|
| JP (2) | JPS60222470A (enExample) |
| AT (3) | AT349140B (enExample) |
| AU (1) | AU503240B2 (enExample) |
| BE (1) | BE832725A (enExample) |
| BG (1) | BG27753A3 (enExample) |
| CH (1) | CH623330A5 (enExample) |
| CS (3) | CS202056B2 (enExample) |
| CY (1) | CY1120A (enExample) |
| GB (1) | GB1525626A (enExample) |
| HK (1) | HK45081A (enExample) |
| KE (1) | KE3157A (enExample) |
| MY (1) | MY8200111A (enExample) |
| SU (2) | SU691094A3 (enExample) |
| ZA (1) | ZA755543B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093723A (en) | 1976-05-19 | 1978-06-06 | Smithkline Corporation | 7-Acyl-3-(sulfonic acid and sulfamoyl substituted tetrazolyl thiomethyl) cephalosporins |
| US4082912A (en) | 1976-06-30 | 1978-04-04 | Bristol-Myers Company | Certain 7-acylamido-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylmethyl)-3-cephem-4-carboxylic acids their salts and easily hydrolyzed esters |
| US4278670A (en) * | 1976-07-12 | 1981-07-14 | Smithkline Corporation | 7-Alpha-oxyiminoacylcephalosporins |
| US4066762A (en) * | 1976-07-12 | 1978-01-03 | Smithkline Corporation | Derivatives of 7-(2-substituted-2-hydroxyiminoacetamido)-3-(1-substituted tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid |
| US4117125A (en) | 1977-06-24 | 1978-09-26 | Smithkline Corporation | 7-Acylamino-3-[1-[2-(carboxymethylamino]ethyl) tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acids |
| DK225179A (da) | 1978-06-22 | 1979-12-23 | Chugai Pharmaceutical Co Ltd | Fremgangsmaade til fremstilling af cephalosporinderivater |
| JPH01300075A (ja) * | 1988-05-25 | 1989-12-04 | Tokyo Seimitsu Hatsujo Kk | 流動体注入装置 |
-
1975
- 1975-08-25 BE BE159447A patent/BE832725A/xx not_active IP Right Cessation
- 1975-08-29 ZA ZA00755543A patent/ZA755543B/xx unknown
- 1975-09-01 BG BG036219A patent/BG27753A3/xx unknown
- 1975-09-02 GB GB36079/75A patent/GB1525626A/en not_active Expired
- 1975-09-02 CY CY1120A patent/CY1120A/xx unknown
- 1975-09-02 AU AU84469/75A patent/AU503240B2/en not_active Expired
- 1975-09-02 AT AT676475A patent/AT349140B/de not_active IP Right Cessation
- 1975-09-02 CH CH1134575A patent/CH623330A5/de not_active IP Right Cessation
- 1975-09-03 SU SU752170664A patent/SU691094A3/ru active
- 1975-09-03 CS CS755997A patent/CS202056B2/cs unknown
-
1976
- 1976-08-10 SU SU762388313A patent/SU685157A3/ru active
-
1977
- 1977-06-07 CS CS773751A patent/CS202058B2/cs unknown
- 1977-06-07 CS CS773750A patent/CS202057B2/cs unknown
- 1977-10-10 AT AT723377A patent/AT348520B/de not_active IP Right Cessation
-
1978
- 1978-04-24 AT AT294178A patent/AT349638B/de not_active IP Right Cessation
-
1981
- 1981-08-25 KE KE3157A patent/KE3157A/xx unknown
- 1981-09-03 HK HK450/81A patent/HK45081A/xx unknown
-
1982
- 1982-12-30 MY MY111/82A patent/MY8200111A/xx unknown
-
1985
- 1985-03-11 JP JP60046700A patent/JPS60222470A/ja active Granted
- 1985-03-11 JP JP60046699A patent/JPS60222489A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CS202057B2 (en) | 1980-12-31 |
| CY1120A (en) | 1981-12-04 |
| CS202058B2 (en) | 1980-12-31 |
| KE3157A (en) | 1981-09-18 |
| JPS6135200B2 (enExample) | 1986-08-12 |
| BG27753A3 (en) | 1979-12-12 |
| JPS60222470A (ja) | 1985-11-07 |
| AT348520B (de) | 1979-02-26 |
| ATA676475A (de) | 1978-08-15 |
| SU685157A3 (ru) | 1979-09-05 |
| AT349638B (de) | 1979-04-10 |
| GB1525626A (en) | 1978-09-20 |
| ATA294178A (de) | 1978-09-15 |
| HK45081A (en) | 1981-09-11 |
| JPS60222489A (ja) | 1985-11-07 |
| AU503240B2 (en) | 1979-08-30 |
| MY8200111A (en) | 1982-12-31 |
| BE832725A (fr) | 1976-02-25 |
| AT349140B (de) | 1979-03-26 |
| ATA723377A (de) | 1978-07-15 |
| CH623330A5 (en) | 1981-05-29 |
| CS202056B2 (en) | 1980-12-31 |
| ZA755543B (en) | 1976-07-28 |
| AU8446975A (en) | 1977-03-10 |
| JPS6348870B2 (enExample) | 1988-09-30 |
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