CS223812B2 - Method of making the 6-aminopenicillane acid - Google Patents
Method of making the 6-aminopenicillane acid Download PDFInfo
- Publication number
- CS223812B2 CS223812B2 CS722414A CS241472A CS223812B2 CS 223812 B2 CS223812 B2 CS 223812B2 CS 722414 A CS722414 A CS 722414A CS 241472 A CS241472 A CS 241472A CS 223812 B2 CS223812 B2 CS 223812B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- filament
- enzyme
- penicillins
- ring structure
- substance
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 14
- 230000007062 hydrolysis Effects 0.000 claims abstract description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 12
- 229920002284 Cellulose triacetate Polymers 0.000 claims abstract description 4
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims abstract description 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 31
- 239000000835 fiber Substances 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 12
- 229940056360 penicillin g Drugs 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 abstract description 20
- 102000004190 Enzymes Human genes 0.000 abstract description 20
- 229930182555 Penicillin Natural products 0.000 abstract description 20
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 230000002255 enzymatic effect Effects 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000012429 reaction media Substances 0.000 abstract description 5
- 241000588724 Escherichia coli Species 0.000 abstract description 4
- 230000000717 retained effect Effects 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 241000194107 Bacillus megaterium Species 0.000 abstract description 2
- 241000588915 Klebsiella aerogenes Species 0.000 abstract description 2
- 150000002960 penicillins Chemical class 0.000 abstract 6
- 239000000126 substance Substances 0.000 abstract 6
- 229930186147 Cephalosporin Natural products 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229940124587 cephalosporin Drugs 0.000 abstract 2
- 150000001780 cephalosporins Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 241000186046 Actinomyces Species 0.000 abstract 1
- 241000588813 Alcaligenes faecalis Species 0.000 abstract 1
- 241000223600 Alternaria Species 0.000 abstract 1
- 241000228212 Aspergillus Species 0.000 abstract 1
- 241000123650 Botrytis cinerea Species 0.000 abstract 1
- 239000001856 Ethyl cellulose Substances 0.000 abstract 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 1
- 241000235395 Mucor Species 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 241000187747 Streptomyces Species 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 229940005347 alcaligenes faecalis Drugs 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- -1 ampicillin Chemical class 0.000 abstract 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 abstract 1
- 229960000723 ampicillin Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229920001249 ethyl cellulose Polymers 0.000 abstract 1
- 235000019325 ethyl cellulose Nutrition 0.000 abstract 1
- 230000002538 fungal effect Effects 0.000 abstract 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 abstract 1
- 108700004370 poly-gamma-methylglutamate Proteins 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000098 polyolefin Polymers 0.000 abstract 1
- 238000002317 scanning near-field acoustic microscopy Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 17
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 17
- 229940049954 penicillin Drugs 0.000 description 14
- 229940088598 enzyme Drugs 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000238876 Acari Species 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108010073038 Penicillin Amidase Proteins 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 101100016034 Nicotiana tabacum APIC gene Proteins 0.000 description 1
- 241000228150 Penicillium chrysogenum Species 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 238000000711 polarimetry Methods 0.000 description 1
- ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000029219 regulation of pH Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 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
- C12P35/02—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin by desacylation of the substituent in the 7 position
-
- 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
- C12P35/04—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin by acylation of the substituent in the 7 position
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Cephalosporin Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS812270A CS224610B2 (cs) | 1972-04-11 | 1981-03-27 | Způsob výroby polosyntetického penicilinu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2377771 | 1971-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS223812B2 true CS223812B2 (en) | 1983-11-25 |
Family
ID=11209882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS722414A CS223812B2 (en) | 1971-04-28 | 1972-04-11 | Method of making the 6-aminopenicillane acid |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5413514B1 (en)) |
| AR (1) | AR192936A1 (en)) |
| AT (1) | AT318805B (en)) |
| BE (1) | BE782646A (en)) |
| BR (1) | BR7202723D0 (en)) |
| CH (2) | CH565181A5 (en)) |
| CS (1) | CS223812B2 (en)) |
| DD (1) | DD100721A5 (en)) |
| DE (1) | DE2221046A1 (en)) |
| EG (1) | EG10474A (en)) |
| ES (1) | ES402865A1 (en)) |
| FR (1) | FR2134530B1 (en)) |
| GB (1) | GB1348359A (en)) |
| HU (1) | HU168856B (en)) |
| IE (1) | IE36334B1 (en)) |
| IL (1) | IL39158A (en)) |
| LU (1) | LU65258A1 (en)) |
| NL (1) | NL7205609A (en)) |
| PL (1) | PL98632B1 (en)) |
| YU (3) | YU112572A (en)) |
| ZA (1) | ZA722837B (en)) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1492937A (en) * | 1973-12-28 | 1977-11-23 | Beecham Group Ltd | Enzyme complexes and their use |
| DE2409569C2 (de) * | 1974-02-28 | 1982-02-18 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 7-Amino- Ω3-cephem-Derivaten |
| US4113566A (en) * | 1976-11-26 | 1978-09-12 | Pfizer Inc. | Process for preparing 6-aminopenicillanic acid |
| US4596777A (en) * | 1983-08-10 | 1986-06-24 | E. R. Squibb & Sons, Inc. | Process for preparing (3S)-3-[[[2-(protected or unprotected amino)-4-thiazolyl]acetyl]amino]-2-oxo-1-azetidinesulfonic acid and 4-substituted derivatives thereof |
| CZ69593A3 (en) * | 1992-04-24 | 1993-12-15 | Lilly Co Eli | Process for preparing cephalosporins |
| DE19646550A1 (de) * | 1996-10-31 | 1998-05-07 | Fzb Biotechnik Gmbh | Kombiniertes Verfahren zur lösungsmittelarmen Gewinnung von Produkten aus der biokatalytischen Spaltung von Penicillin- oder Cephalosporin G-Lösungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE727506A (en)) * | 1968-02-15 | 1969-07-01 | ||
| ES365631A1 (es) * | 1968-04-05 | 1971-03-16 | Beecham Group Ltd | Un procedimiento para la preparacion de acido 6-aminopeni- cilanico. |
-
1972
- 1972-04-07 IL IL39158A patent/IL39158A/en unknown
- 1972-04-09 EG EG140/72A patent/EG10474A/xx active
- 1972-04-11 CS CS722414A patent/CS223812B2/cs unknown
- 1972-04-25 NL NL7205609A patent/NL7205609A/xx unknown
- 1972-04-26 FR FR7214799A patent/FR2134530B1/fr not_active Expired
- 1972-04-26 JP JP4215072A patent/JPS5413514B1/ja active Pending
- 1972-04-26 BE BE782646A patent/BE782646A/xx not_active IP Right Cessation
- 1972-04-26 AR AR241744A patent/AR192936A1/es active
- 1972-04-26 DD DD162592A patent/DD100721A5/xx unknown
- 1972-04-26 PL PL1972154991A patent/PL98632B1/pl unknown
- 1972-04-27 ES ES402865A patent/ES402865A1/es not_active Expired
- 1972-04-27 YU YU01125/72A patent/YU112572A/xx unknown
- 1972-04-27 IE IE561/72A patent/IE36334B1/xx unknown
- 1972-04-27 ZA ZA722837A patent/ZA722837B/xx unknown
- 1972-04-27 GB GB1972672A patent/GB1348359A/en not_active Expired
- 1972-04-27 BR BR2723/72A patent/BR7202723D0/pt unknown
- 1972-04-27 HU HUSA2349A patent/HU168856B/hu unknown
- 1972-04-27 LU LU65258D patent/LU65258A1/xx unknown
- 1972-04-28 CH CH440373A patent/CH565181A5/xx not_active IP Right Cessation
- 1972-04-28 DE DE19722221046 patent/DE2221046A1/de active Pending
- 1972-04-28 CH CH643472A patent/CH550822A/fr not_active IP Right Cessation
- 1972-04-28 AT AT377372A patent/AT318805B/de not_active IP Right Cessation
-
1979
- 1979-09-05 YU YU02166/79A patent/YU216679A/xx unknown
-
1980
- 1980-04-17 YU YU01061/80A patent/YU106180A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL39158A (en) | 1977-08-31 |
| CH565181A5 (en)) | 1975-08-15 |
| AT318805B (de) | 1974-11-25 |
| PL98632B1 (pl) | 1978-05-31 |
| EG10474A (en) | 1976-04-30 |
| DD100721A5 (en)) | 1973-10-05 |
| ES402865A1 (es) | 1976-02-01 |
| BE782646A (fr) | 1972-08-16 |
| YU216679A (en) | 1982-05-31 |
| DE2221046A1 (de) | 1973-11-15 |
| NL7205609A (en)) | 1972-10-31 |
| JPS5413514B1 (en)) | 1979-05-31 |
| AR192936A1 (es) | 1973-03-21 |
| YU106180A (en) | 1982-05-31 |
| BR7202723D0 (pt) | 1974-02-19 |
| ZA722837B (en) | 1973-02-28 |
| HU168856B (en)) | 1976-07-28 |
| FR2134530B1 (en)) | 1975-10-17 |
| IE36334B1 (en) | 1976-10-13 |
| IE36334L (en) | 1972-10-28 |
| LU65258A1 (en)) | 1972-07-14 |
| IL39158A0 (en) | 1972-06-28 |
| FR2134530A1 (en)) | 1972-12-08 |
| CH550822A (fr) | 1974-06-28 |
| GB1348359A (en) | 1974-03-13 |
| YU112572A (en) | 1982-02-28 |
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