IL45888A - Process for the preparation of dataxoxyspalosporin C - Google Patents
Process for the preparation of dataxoxyspalosporin CInfo
- Publication number
- IL45888A IL45888A IL45888A IL4588874A IL45888A IL 45888 A IL45888 A IL 45888A IL 45888 A IL45888 A IL 45888A IL 4588874 A IL4588874 A IL 4588874A IL 45888 A IL45888 A IL 45888A
- Authority
- IL
- Israel
- Prior art keywords
- deacetoxycephalosporin
- growth
- nrrl
- column
- medium
- Prior art date
Links
- NNQIJOYQWYKBOW-VMAXQDLPSA-N deacetoxycephalosporin-c Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@H](N)C(O)=O)[C@H]12 NNQIJOYQWYKBOW-VMAXQDLPSA-N 0.000 title claims abstract 5
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 15
- 241000187395 Streptomyces microflavus Species 0.000 claims abstract description 16
- 241000424942 Streptomyces clavuligerus ATCC 27064 Species 0.000 claims abstract description 13
- 238000010564 aerobic fermentation Methods 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 230000003115 biocidal effect Effects 0.000 claims description 26
- 239000002609 medium Substances 0.000 claims description 25
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- 241001655322 Streptomycetales Species 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- NNQIJOYQWYKBOW-UHFFFAOYSA-N desacetoxycephalosphorin G Natural products S1CC(C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 NNQIJOYQWYKBOW-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 12
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 abstract description 7
- 239000002207 metabolite Substances 0.000 abstract description 7
- CSGFFYNMTALICU-ZWNOBZJWSA-N adipyl-7-aminodesacetoxycephalosporanic acid Natural products CC1=C(N2[C@H](SC1)[C@H](NC(=O)CCCCC(O)=O)C2=O)C(O)=O CSGFFYNMTALICU-ZWNOBZJWSA-N 0.000 abstract description 6
- 238000012258 culturing Methods 0.000 abstract description 4
- NNQIJOYQWYKBOW-JWKOBGCHSA-N deacetoxycephalosporin C Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 NNQIJOYQWYKBOW-JWKOBGCHSA-N 0.000 description 49
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- 238000005406 washing Methods 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- GMKMEZVLHJARHF-UHFFFAOYSA-N (2R,6R)-form-2.6-Diaminoheptanedioic acid Natural products OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 description 1
- NNQIJOYQWYKBOW-YHBRXECLSA-N (6R)-7-[(5-amino-5-carboxypentanoyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC(CCCC(=O)NC1[C@@H]2N(C(=C(CS2)C)C(=O)O)C1=O)C(=O)O NNQIJOYQWYKBOW-YHBRXECLSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ORQHMODRGXTBFU-UHFFFAOYSA-N 7-Methoxycephalosporin C Natural products S1CC(COC(C)=O)=C(C(O)=O)N2C(=O)C(OC)(NC(=O)CCCC(N)C(O)=O)C21 ORQHMODRGXTBFU-UHFFFAOYSA-N 0.000 description 1
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- 241000736839 Chara Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
- QWIZNVHXZXRPDR-UHFFFAOYSA-N D-melezitose Natural products O1C(CO)C(O)C(O)C(O)C1OC1C(O)C(CO)OC1(CO)OC1OC(CO)C(O)C(O)C1O QWIZNVHXZXRPDR-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- MIFYHUACUWQUKT-UHFFFAOYSA-N Isopenicillin N Natural products OC(=O)C1C(C)(C)SC2C(NC(=O)CCCC(N)C(O)=O)C(=O)N21 MIFYHUACUWQUKT-UHFFFAOYSA-N 0.000 description 1
- GMKMEZVLHJARHF-WHFBIAKZSA-N LL-2,6-diaminopimelic acid Chemical compound OC(=O)[C@@H](N)CCC[C@H](N)C(O)=O GMKMEZVLHJARHF-WHFBIAKZSA-N 0.000 description 1
- 241000227653 Lycopersicon Species 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 241000187708 Micromonospora Species 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000364057 Peoria Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 1
- 241000228417 Sarocladium strictum Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000203640 Thermomonospora Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229950008644 adicillin Drugs 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 239000007613 bennett's agar Substances 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 1
- 229940106164 cephalexin Drugs 0.000 description 1
- QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000012225 czapek media Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- QWIZNVHXZXRPDR-WSCXOGSTSA-N melezitose Chemical compound O([C@@]1(O[C@@H]([C@H]([C@@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)CO)CO)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QWIZNVHXZXRPDR-WSCXOGSTSA-N 0.000 description 1
- GMKMEZVLHJARHF-SYDPRGILSA-N meso-2,6-diaminopimelic acid Chemical compound [O-]C(=O)[C@@H]([NH3+])CCC[C@@H]([NH3+])C([O-])=O GMKMEZVLHJARHF-SYDPRGILSA-N 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- MIFYHUACUWQUKT-GPUHXXMPSA-N penicillin N Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@H](NC(=O)CCC[C@@H](N)C(O)=O)C(=O)N21 MIFYHUACUWQUKT-GPUHXXMPSA-N 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
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000035440 response to pH Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000012807 shake-flask culturing Methods 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 241001446247 uncultured actinomycete Species 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
- C12P35/06—Cephalosporin C; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US421303A US3862008A (en) | 1973-12-03 | 1973-12-03 | Process for deacetoxycephalosporin c. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45888A0 IL45888A0 (en) | 1974-12-31 |
| IL45888A true IL45888A (en) | 1977-05-31 |
Family
ID=23669982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45888A IL45888A (en) | 1973-12-03 | 1974-10-21 | Process for the preparation of dataxoxyspalosporin C |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3862008A (en, 2012) |
| JP (1) | JPS5094190A (en, 2012) |
| AR (1) | AR202671A1 (en, 2012) |
| AT (1) | AT335598B (en, 2012) |
| BE (1) | BE822872A (en, 2012) |
| CS (1) | CS176292B2 (en, 2012) |
| DD (1) | DD116835A5 (en, 2012) |
| DE (1) | DE2455683A1 (en, 2012) |
| DK (1) | DK625074A (en, 2012) |
| ES (1) | ES432549A1 (en, 2012) |
| FR (1) | FR2253090A1 (en, 2012) |
| GB (1) | GB1485814A (en, 2012) |
| HU (1) | HU168206B (en, 2012) |
| IE (1) | IE40094B1 (en, 2012) |
| IL (1) | IL45888A (en, 2012) |
| NL (1) | NL7415773A (en, 2012) |
| PH (1) | PH11354A (en, 2012) |
| RO (2) | RO70548A (en, 2012) |
| SE (1) | SE7414461L (en, 2012) |
| ZA (1) | ZA746646B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE425254B (sv) * | 1973-06-16 | 1982-09-13 | Takeda Chemical Industries Ltd | Sett att framstella deacetoxiefalosporin c genom odling av vissa organismer, i nagra fall pa medier med visst aminosyrainnehall |
| JPS5718878B2 (en, 2012) * | 1974-03-06 | 1982-04-19 | ||
| US4110165A (en) * | 1974-04-20 | 1978-08-29 | Beecham Group Limited | Process for the production of clavulanic acid |
| GB8521516D0 (en) * | 1985-08-29 | 1985-10-02 | Beecham Group Plc | Compounds |
| US6709859B1 (en) * | 1986-01-31 | 2004-03-23 | Beecham Group P.L.C. | Chromosomal DNA Fragments Encoding Enzymes for Encoding B-Lactam Biosynthesis Enzymes, and Vector and Transformants for Their Expression |
| DE3789880T2 (de) * | 1986-01-31 | 1994-09-08 | Beecham Group Plc | Isolierung und Expression von bei der Biosynthese von Beta-Laktamen beteiligten Genen. |
| CA2898725A1 (en) | 2013-02-11 | 2014-08-14 | Bayer Cropscience Lp | Compositions comprising a streptomyces-based biological control agent and an insecticide |
| CN113234093A (zh) * | 2021-04-13 | 2021-08-10 | 伊犁川宁生物技术股份有限公司 | 一种3-去乙酰氧基头孢菌素c钠盐及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3719563A (en) * | 1970-08-03 | 1973-03-06 | Lilly Co Eli | Process for producing 7-(5-amino-5-carboxyvaleramido)-7-methoxycephalosporamic acid |
| US3770590A (en) * | 1971-12-01 | 1973-11-06 | Merck & Co Inc | Fermentation process |
-
1973
- 1973-12-03 US US421303A patent/US3862008A/en not_active Expired - Lifetime
-
1974
- 1974-10-18 ZA ZA00746646A patent/ZA746646B/xx unknown
- 1974-10-21 IL IL45888A patent/IL45888A/en unknown
- 1974-10-25 PH PH16453A patent/PH11354A/en unknown
- 1974-10-29 IE IE2227/74A patent/IE40094B1/xx unknown
- 1974-11-12 AR AR256478A patent/AR202671A1/es active
- 1974-11-18 SE SE7414461A patent/SE7414461L/xx unknown
- 1974-11-25 DE DE19742455683 patent/DE2455683A1/de active Pending
- 1974-11-29 AT AT958674A patent/AT335598B/de not_active IP Right Cessation
- 1974-12-02 GB GB52026/74A patent/GB1485814A/en not_active Expired
- 1974-12-02 DK DK625074A patent/DK625074A/da unknown
- 1974-12-02 HU HUEI579A patent/HU168206B/hu unknown
- 1974-12-02 FR FR7439426A patent/FR2253090A1/fr not_active Withdrawn
- 1974-12-03 ES ES432549A patent/ES432549A1/es not_active Expired
- 1974-12-03 DD DD182734A patent/DD116835A5/xx unknown
- 1974-12-03 CS CS8273A patent/CS176292B2/cs unknown
- 1974-12-03 NL NL7415773A patent/NL7415773A/xx not_active Application Discontinuation
- 1974-12-03 BE BE151085A patent/BE822872A/xx unknown
- 1974-12-03 JP JP49140108A patent/JPS5094190A/ja active Pending
- 1974-12-04 RO RO7490299A patent/RO70548A/ro unknown
- 1974-12-04 RO RO7490300A patent/RO70549A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO70549A (ro) | 1981-09-24 |
| PH11354A (en) | 1977-11-02 |
| CS176292B2 (en, 2012) | 1977-06-30 |
| IL45888A0 (en) | 1974-12-31 |
| DD116835A5 (en, 2012) | 1975-12-12 |
| US3862008A (en) | 1975-01-21 |
| IE40094L (en) | 1975-06-03 |
| HU168206B (en, 2012) | 1976-03-28 |
| AR202671A1 (es) | 1975-06-30 |
| AT335598B (de) | 1977-03-25 |
| ES432549A1 (es) | 1977-02-16 |
| DE2455683A1 (de) | 1975-06-05 |
| ZA746646B (en) | 1976-05-26 |
| NL7415773A (nl) | 1975-06-05 |
| SE7414461L (en, 2012) | 1975-06-04 |
| DK625074A (en, 2012) | 1975-07-28 |
| FR2253090A1 (en, 2012) | 1975-06-27 |
| IE40094B1 (en) | 1979-03-14 |
| JPS5094190A (en, 2012) | 1975-07-26 |
| RO70548A (ro) | 1981-09-24 |
| GB1485814A (en) | 1977-09-14 |
| BE822872A (fr) | 1975-06-03 |
| ATA958674A (de) | 1976-07-15 |
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