NL1007302C2 - Werkwijze voor de bereiding van een ß-lactam antibioticum. - Google Patents

Werkwijze voor de bereiding van een ß-lactam antibioticum. Download PDF

Info

Publication number: NL1007302C2
Authority: NL; Netherlands
Prior art keywords: acylating agent; lactam; reaction; mixture; solution
Prior art date: 1997-10-17

Application number

NL1007302A

Other languages

English (en)

Dutch (nl)

Inventor

Harold Monro Moody

Theodorus Johannes Godf Dooren

Johanna Christ Wagemans-Smeets

Original Assignee

Dsm Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-10-17

Filing date

1997-10-17

Publication date

1999-04-20

1997-10-17 Priority to NL1007302A priority Critical patent/NL1007302C2/nl

1997-10-17 Application filed by Dsm Nv filed Critical Dsm Nv

1998-10-01 Priority to PCT/NL1998/000570 priority patent/WO1999020786A1/fr

1998-10-01 Priority to KR10-2000-7004098A priority patent/KR100516271B1/ko

1998-10-01 Priority to CNB988122804A priority patent/CN1165626C/zh

1998-10-01 Priority to US09/529,569 priority patent/US6287799B1/en

1998-10-01 Priority to AT98949243T priority patent/ATE234934T1/de

1998-10-01 Priority to ES98949243T priority patent/ES2195400T3/es

1998-10-01 Priority to BR9813079-0A priority patent/BR9813079A/pt

1998-10-01 Priority to AU95601/98A priority patent/AU9560198A/en

1998-10-01 Priority to TR2000/00991T priority patent/TR200000991T2/xx

1998-10-01 Priority to EP98949243A priority patent/EP1023454B1/fr

1998-10-07 Priority to IN2240MA1998 priority patent/IN188152B/en

1998-10-17 Priority to EG125898A priority patent/EG21235A/xx

1999-04-20 Application granted granted Critical

1999-04-20 Publication of NL1007302C2 publication Critical patent/NL1007302C2/nl

Links

238000000034 method Methods 0.000 title claims abstract description 41
239000003782 beta lactam antibiotic agent Substances 0.000 title claims abstract description 21
239000002132 β-lactam antibiotic Substances 0.000 title claims abstract description 21
229940124586 β-lactam antibiotics Drugs 0.000 title claims abstract description 21
238000002360 preparation method Methods 0.000 title claims abstract description 15
239000003795 chemical substances by application Substances 0.000 claims abstract description 55
150000003952 β-lactams Chemical class 0.000 claims abstract description 55
238000005917 acylation reaction Methods 0.000 claims abstract description 41
239000011541 reaction mixture Substances 0.000 claims abstract description 19
230000002255 enzymatic effect Effects 0.000 claims abstract description 14
239000002002 slurry Substances 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 33
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 claims description 24
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 23
230000007423 decrease Effects 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims description 3
LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 claims description 2
QNXHTHMVKRGOSJ-UHFFFAOYSA-N 7-amino-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1CC(Cl)=C(C(O)=O)N2C(=O)C(N)C21 QNXHTHMVKRGOSJ-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
230000010933 acylation Effects 0.000 abstract description 9
108090000790 Enzymes Proteins 0.000 description 51
102000004190 Enzymes Human genes 0.000 description 51
239000000243 solution Substances 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 30
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 description 29
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
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 description 13
230000015572 biosynthetic process Effects 0.000 description 13
238000003786 synthesis reaction Methods 0.000 description 13
QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 description 12
229960005361 cefaclor Drugs 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 12
239000007787 solid Substances 0.000 description 12
238000004448 titration Methods 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 10
229960000723 ampicillin Drugs 0.000 description 9
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 9
239000000725 suspension Substances 0.000 description 9
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 8
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
238000006911 enzymatic reaction Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
229960004841 cefadroxil Drugs 0.000 description 6
NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
230000020477 pH reduction Effects 0.000 description 6
239000000376 reactant Substances 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
108010093096 Immobilized Enzymes Proteins 0.000 description 5
108010073038 Penicillin Amidase Proteins 0.000 description 5
229940106164 cephalexin Drugs 0.000 description 5
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 4
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin 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=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 4
229960003022 amoxicillin Drugs 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
230000003247 decreasing effect Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
150000003951 lactams Chemical group 0.000 description 4
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 4
KIYRSYYOVDHSPG-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetamide Chemical compound NC(=O)[C@H](N)C1=CC=CC=C1 KIYRSYYOVDHSPG-SSDOTTSWSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
241000589220 Acetobacter Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000223218 Fusarium Species 0.000 description 2
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
241000589634 Xanthomonas Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
150000005331 phenylglycines Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
WDLWHQDACQUCJR-ZAMMOSSLSA-N (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)/C=C/C)C(O)=O)=CC=C(O)C=C1 WDLWHQDACQUCJR-ZAMMOSSLSA-N 0.000 description 1
PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 1
JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
241000607534 Aeromonas Species 0.000 description 1
108700023418 Amidases Proteins 0.000 description 1
241000726092 Aphanocladium Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000194110 Bacillus sp. (in: Bacteria) Species 0.000 description 1
229930186147 Cephalosporin Chemical class 0.000 description 1
241001619326 Cephalosporium Species 0.000 description 1
229920001661 Chitosan Polymers 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
241000588722 Escherichia Species 0.000 description 1
241000589565 Flavobacterium Species 0.000 description 1
241000427940 Fusarium solani Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
229910003556 H2 SO4 Inorganic materials 0.000 description 1
241000586779 Protaminobacter Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
102000005922 amidase Human genes 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
238000010923 batch production Methods 0.000 description 1
239000011324 bead Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 1
229950004030 cefaloglycin Drugs 0.000 description 1
229960001139 cefazolin Drugs 0.000 description 1
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 1
GPRBEKHLDVQUJE-VINNURBNSA-N cefotaxime Chemical compound N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CSC(N)=N1 GPRBEKHLDVQUJE-VINNURBNSA-N 0.000 description 1
229960004261 cefotaxime Drugs 0.000 description 1
229960002580 cefprozil Drugs 0.000 description 1
229960002588 cefradine Drugs 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010304 firing Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
JAPHQRWPEGVNBT-UTUOFQBUSA-N loracarbef Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CC[C@@H]32)C([O-])=O)=O)[NH3+])=CC=CC=C1 JAPHQRWPEGVNBT-UTUOFQBUSA-N 0.000 description 1
229960001977 loracarbef Drugs 0.000 description 1
SZBDOFWNZVHVGR-MRVPVSSYSA-N methyl (2r)-2-amino-2-(4-hydroxyphenyl)acetate Chemical compound COC(=O)[C@H](N)C1=CC=C(O)C=C1 SZBDOFWNZVHVGR-MRVPVSSYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000010626 work up procedure 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
- C12P35/04—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
- 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
- C12P37/00—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin
- C12P37/04—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin by acylation of the substituent in the 6 position

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)
Cephalosporin Compounds (AREA)

NL1007302A 1997-10-17 1997-10-17 Werkwijze voor de bereiding van een ß-lactam antibioticum. NL1007302C2 (nl)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
NL1007302A NL1007302C2 (nl)	1997-10-17	1997-10-17	Werkwijze voor de bereiding van een ß-lactam antibioticum.
AU95601/98A AU9560198A (en)	1997-10-17	1998-10-01	Process for the preparation of a beta-lactam antibiotic
CNB988122804A CN1165626C (zh)	1997-10-17	1998-10-01	用于制备β-内酰胺抗生素的方法
US09/529,569 US6287799B1 (en)	1997-10-17	1998-10-01	Process for the preparation of aβ-lactam antibiotic
AT98949243T ATE234934T1 (de)	1997-10-17	1998-10-01	Verfahren zur herstellung von einem beta-laktam antibiotikum
ES98949243T ES2195400T3 (es)	1997-10-17	1998-10-01	Procedimiento de preparacion de un antibiotico beta-lactamico.
PCT/NL1998/000570 WO1999020786A1 (fr)	1997-10-17	1998-10-01	PROCEDE DE PREPARATION D'UN ANTIBIOTIQUE DE β-LACTAME
KR10-2000-7004098A KR100516271B1 (ko)	1997-10-17	1998-10-01	β-락탐 항생제의 제조방법
TR2000/00991T TR200000991T2 (tr)	1997-10-17	1998-10-01	Bir beta-laktam antibiyotiğinin hazırlanması için işlem.
EP98949243A EP1023454B1 (fr)	1997-10-17	1998-10-01	Procede de preparation d'un antibiotique de (beta)-lactame
BR9813079-0A BR9813079A (pt)	1997-10-17	1998-10-01	Processo para a preparação de um antibiótico beta-lactama
IN2240MA1998 IN188152B (fr)	1997-10-17	1998-10-07
EG125898A EG21235A (en)	1997-10-17	1998-10-17	Process for the preparation of a b-lactam antibiotic

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1007302		1997-10-17
NL1007302A NL1007302C2 (nl)	1997-10-17	1997-10-17	Werkwijze voor de bereiding van een ß-lactam antibioticum.

Publications (1)

Publication Number	Publication Date
NL1007302C2 true NL1007302C2 (nl)	1999-04-20

Family

ID=19765855

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1007302A NL1007302C2 (nl)	1997-10-17	1997-10-17	Werkwijze voor de bereiding van een ß-lactam antibioticum.

Country Status (13)

Country	Link
US (1)	US6287799B1 (fr)
EP (1)	EP1023454B1 (fr)
KR (1)	KR100516271B1 (fr)
CN (1)	CN1165626C (fr)
AT (1)	ATE234934T1 (fr)
AU (1)	AU9560198A (fr)
BR (1)	BR9813079A (fr)
EG (1)	EG21235A (fr)
ES (1)	ES2195400T3 (fr)
IN (1)	IN188152B (fr)
NL (1)	NL1007302C2 (fr)
TR (1)	TR200000991T2 (fr)
WO (1)	WO1999020786A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL1006266C2 (nl)	1997-06-10	1998-12-14	Chemferm Vof	Werkwijze voor de bereiding van ampicilline.
EP1394262A1 (fr) *	2002-08-30	2004-03-03	Bioferma Murcia, S.A.	Procédé enzymatique de préparation de composés de bêta-lactame
MX2007007937A (es) *	2004-12-27	2007-08-21	Dsm Ip Assets Bv	Procedimiento para la sintesis de cefaclor.
WO2007134987A1 (fr) *	2006-05-19	2007-11-29	Dsm Ip Assets B.V.	Procédé de cristallisation du céfadroxil
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CN103937692B (zh) *	2014-04-30	2016-03-23	江南大学	一株丝枝霉菌株及其生产β-葡萄糖苷酶的方法
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Also Published As

Publication number	Publication date
US6287799B1 (en)	2001-09-11
ATE234934T1 (de)	2003-04-15
IN188152B (fr)	2002-08-24
EG21235A (en)	2001-03-31
EP1023454A1 (fr)	2000-08-02
KR20010024519A (ko)	2001-03-26
ES2195400T3 (es)	2003-12-01
CN1165626C (zh)	2004-09-08
WO1999020786A1 (fr)	1999-04-29
AU9560198A (en)	1999-05-10
TR200000991T2 (tr)	2000-07-21
KR100516271B1 (ko)	2005-09-20
BR9813079A (pt)	2000-08-15
EP1023454B1 (fr)	2003-03-19
CN1282377A (zh)	2001-01-31

Publication	Publication Date	Title
NL1007302C2 (nl)	1999-04-20	Werkwijze voor de bereiding van een ß-lactam antibioticum.
US6048708A (en)	2000-04-11	Process for preparation of β-lactams at constantly high concentration of reactants
CN101631872A (zh)	2010-01-20	制备β-内酰胺化合物的工艺
NL1007077C2 (nl)	1999-03-22	Werkwijze voor de winning van een ß-lactam antibioticum.
NL1006266C2 (nl)	1998-12-14	Werkwijze voor de bereiding van ampicilline.
CN100507000C (zh)	2009-07-01	制备头孢拉定的方法
NL1007076C2 (nl)	1999-03-22	Werkwijze voor de winning van een ß-lactam antibioticum.
KR20010043038A (ko)	2001-05-25	β-락탐 항생제의 결정화 방법
CA2168923C (fr)	2009-09-15	Methode pour la synthese enzymatique d'antibiotiques de type .beta.-lactames en presence d'inhibiteurs enzymatiques
NL1007828C2 (nl)	1999-06-21	Complexen van beta-lactam antibiotica en 1-naftol.
NL1010506C2 (nl)	2000-05-09	Werkwijze voor de bereiding van bêta-lactam antibiotica.
NL1007827C2 (nl)	1999-06-21	Complexen van beta-lactam antibiotica.
US7588913B2 (en)	2009-09-15	Process for the preparation of cephradine
MXPA00003769A (en)	2001-12-04	PROCESS FOR THE PREPARATION OF A&bgr;-LACTAM ANTIBIOTIC
WO1998056945A1 (fr)	1998-12-17	PROCEDE DE PREPARATION D'UNE β-LACTAMINE PAR ACTION ENZYMATIQUE ET ANTIBIOTIQUE AINSI PRODUIT
WO2002020819A2 (fr)	2002-03-14	Procede enzymatique pour l'elaboration de composes a base de beta-lactamines
EP0815256A1 (fr)	1998-01-07	Procede de preparation d'une beta-lactamine
MXPA00010537A (en)	2001-09-07	A METHOD FOR CRYSTALLIZING A&bgr;-LACTAM ANTIBIOTIC
ITMI960033A1 (it)	1997-07-11	Procedimento per la sintesi enzimatica di antibiotici b-lattamici in presenza di un inibitore dell'enzima

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