NL9220025A - Werkwijze voor het bereiden van cephemderivaten. - Google Patents

Werkwijze voor het bereiden van cephemderivaten. Download PDF

Info

Publication number: NL9220025A
Authority: NL; Netherlands
Prior art keywords: mixture; formula; derivative; added; reaction
Prior art date: 1991-11-18

Application number

NL9220025A

Other languages

English (en)

Dutch (nl)

Original Assignee

Cheil Foods & Chem

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.)

1991-11-18

Filing date

1992-09-04

Publication date

1994-12-01

1992-09-04 Application filed by Cheil Foods & Chem filed Critical Cheil Foods & Chem

1994-12-01 Publication of NL9220025A publication Critical patent/NL9220025A/nl

Links

238000000034 method Methods 0.000 title claims description 33
150000001782 cephems Chemical class 0.000 title description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
239000000203 mixture Substances 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 23
-1 acetoxymethyl Chemical group 0.000 claims description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 17
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 16
150000007524 organic acids Chemical class 0.000 claims description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 12
VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
150000001805 chlorine compounds Chemical class 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
238000005917 acylation reaction Methods 0.000 claims description 6
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 6
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 6
238000002955 isolation Methods 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052751 metal Chemical class 0.000 claims description 2
239000002184 metal Chemical class 0.000 claims description 2
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 22
239000013078 crystal Substances 0.000 description 20
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
239000002253 acid Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
239000011877 solvent mixture Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
238000003756 stirring Methods 0.000 description 6
150000003952 β-lactams Chemical class 0.000 description 6
150000001408 amides Chemical class 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000010933 acylation Effects 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000012453 solvate Substances 0.000 description 3
ZVNOEZHWBDKVHV-UHFFFAOYSA-N Cl[PH3]Cl Chemical compound Cl[PH3]Cl ZVNOEZHWBDKVHV-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000012467 final product Substances 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
UAGHIUHHIGBDPQ-XCGJVMPOSA-N (6r)-4-[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1NC(=O)C(=O)N=C1SCC1C=C(C(O)=O)N2C(=O)C[C@H]2S1 UAGHIUHHIGBDPQ-XCGJVMPOSA-N 0.000 description 1
RJFPBECTFIUTHB-INEUFUBQSA-N (6r,7r)-7-azaniumyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC=C(C(O)=O)N2C(=O)[C@@H](N)[C@H]21 RJFPBECTFIUTHB-INEUFUBQSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
CPAITOJVTICXRP-UHFFFAOYSA-N 2-methyl-1h-1,2,4-triazine-5,6-dione Chemical compound CN1C=NC(=O)C(=O)N1 CPAITOJVTICXRP-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
150000003855 acyl compounds Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000005594 diketone group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
LULXBAGMGMJJRW-UHFFFAOYSA-N n,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)CC(=O)N[Si](C)(C)C LULXBAGMGMJJRW-UHFFFAOYSA-N 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- C07D501/06—Acylation of 7-aminocephalosporanic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- 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

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)

NL9220025A 1991-11-18 1992-09-04 Werkwijze voor het bereiden van cephemderivaten. NL9220025A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
KR910020505		1991-11-18
KR1019910020505A KR950014571B1 (ko)	1991-11-18	1991-11-18	세펨 유도체의 제조방법
PCT/KR1992/000041 WO1993010123A1 (en)	1991-11-18	1992-09-04	Process for the preparation of cephem derivatives
KR9200041		1992-09-04

Publications (1)

Publication Number	Publication Date
NL9220025A true NL9220025A (nl)	1994-12-01

Family

ID=19322986

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9220025A NL9220025A (nl)	1991-11-18	1992-09-04	Werkwijze voor het bereiden van cephemderivaten.

Country Status (13)

Country	Link
US (1)	US5317099A (de)
EP (1)	EP0613480B1 (de)
JP (1)	JPH0811755B2 (de)
KR (1)	KR950014571B1 (de)
AT (1)	AT403048B (de)
CH (1)	CH684091A5 (de)
DE (2)	DE4293959T1 (de)
DK (1)	DK56694A (de)
ES (1)	ES2070101B1 (de)
GB (1)	GB2275927B (de)
NL (1)	NL9220025A (de)
SE (1)	SE505050C2 (de)
WO (1)	WO1993010123A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5402609A (en) *	1992-08-13	1995-04-04	Kelley, Jr.; Michael L.	Concrete building block system
TW369530B (en) *	1993-06-10	1999-09-11	Lucky Ltd	Process for preparing cephalosporin compounds from reactive organic acid derivatives
KR100197788B1 (ko) *	1995-06-30	1999-06-15	김충환	세펨 유도체의 제조방법
IN181459B (de) *	1995-12-26	1998-06-20	Lupin Lab Ltd
WO2005076694A2 (en) *	2004-01-16	2005-08-25	Wockhardt Limited	Improved process for the production of cefotaxime sodium
CN108383857B (zh) *	2018-05-04	2021-02-05	山东四环药业股份有限公司	一种盐酸头孢甲肟的制备方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4196205A (en) *	1976-01-23	1980-04-01	Roussel Uclaf	3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives
DE2760123C2 (de) *	1976-01-23	1986-04-30	Roussel-Uclaf, Paris	7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
US4166115A (en) *	1976-04-12	1979-08-28	Fujisawa Pharmaceutical Co., Ltd.	Syn 7-oxoimino substituted derivatives of cephalosporanic acid
US4304770A (en) *	1976-04-12	1981-12-08	Fujisawa Pharmaceutical Co., Ltd.	Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
US4331664A (en) *	1976-04-12	1982-05-25	Fujisawa Pharmaceutical Co., Ltd.	Syn isomer of 7-[2-cyclo(lower) alkoxyimino-2-(2-amino-or substituted aminothiazol-4-yl)acetamido]-3-lower alkanoyloxymethyl or heterocyclicthiomethyl-3-cephem-4-carboxylic acid compounds
GR63088B (en) *	1976-04-14	1979-08-09	Takeda Chemical Industries Ltd	Preparation process of novel cephalosporins
US4370326A (en) *	1977-09-13	1983-01-25	Fujisawa Pharmaceutical Co., Ltd.	Cephem compounds and composition
DE2758000A1 (de) *	1977-12-24	1979-07-05	Hoechst Ag	Verfahren zur herstellung von penicillinen und cephalosporinen
CH641468A5 (de) *	1978-05-30	1984-02-29	Hoffmann La Roche	Cephemderivate.
MC1259A1 (fr) *	1978-05-30	1980-01-14	Hoffmann La Roche	Derives acyles
GB2025933B (en) *	1978-06-13	1982-10-27	Fujisawa Pharmaceutical Co	Cephem and cepham compounds
FR2462439A1 (fr) *	1979-07-26	1981-02-13	Roussel Uclaf	Nouveau procede de preparation de produits derives de l'acide 7-/(2-aryl) 2-hydroxyimino acetamido/cephalosporanique
DE3165922D1 (en) *	1980-03-28	1984-10-18	Biochemie Gmbh	New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production
KR870001332B1 (ko) *	1984-09-27	1987-07-18	한미약품공업 주식회사	세펨 유도체의 간단한 제조방법
DE68929368T2 (de) *	1988-03-16	2002-08-14	Eisai Co., Ltd.	Cephemderivate und Verfahren zu ihrer Herstellung
IT1234385B (it) *	1989-05-23	1992-05-18	Sbd Synthetic And Biolog Devel	Procedimento migliorato per la produzione di una sostanza antibiotica appartenente al gruppo delle cefalosporine

1991
- 1991-11-18 KR KR1019910020505A patent/KR950014571B1/ko not_active Expired - Fee Related
1992
- 1992-09-04 EP EP92919241A patent/EP0613480B1/de not_active Expired - Lifetime
- 1992-09-04 DE DE4293959T patent/DE4293959T1/de active Pending
- 1992-09-04 CH CH2208/93A patent/CH684091A5/de not_active IP Right Cessation
- 1992-09-04 JP JP5509158A patent/JPH0811755B2/ja not_active Expired - Fee Related
- 1992-09-04 WO PCT/KR1992/000041 patent/WO1993010123A1/en not_active Ceased
- 1992-09-04 AT AT0903092A patent/AT403048B/de not_active IP Right Cessation
- 1992-09-04 GB GB9409758A patent/GB2275927B/en not_active Expired - Fee Related
- 1992-09-04 NL NL9220025A patent/NL9220025A/nl not_active Application Discontinuation
- 1992-09-04 DE DE4293959A patent/DE4293959C2/de not_active Expired - Fee Related
- 1992-10-13 US US07/959,359 patent/US5317099A/en not_active Expired - Lifetime
1993
- 1993-07-16 ES ES09350013A patent/ES2070101B1/es not_active Expired - Fee Related
1994
- 1994-05-18 SE SE9401706A patent/SE505050C2/sv not_active IP Right Cessation
- 1994-05-18 DK DK056694A patent/DK56694A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
KR950014571B1 (ko)	1995-12-08
AT403048B (de)	1997-10-27
CH684091A5 (de)	1994-07-15
SE9401706L (sv)	1994-07-07
EP0613480B1 (de)	1999-03-31
US5317099A (en)	1994-05-31
SE505050C2 (sv)	1997-06-16
ES2070101B1 (es)	1996-02-16
DK56694A (da)	1994-05-18
GB2275927B (en)	1995-10-04
EP0613480A1 (de)	1994-09-07
KR930010043A (ko)	1993-06-21
GB2275927A (en)	1994-09-14
JPH0811755B2 (ja)	1996-02-07
SE9401706D0 (sv)	1994-05-18
JPH07501072A (ja)	1995-02-02
WO1993010123A1 (en)	1993-05-27
ATA903092A (de)	1997-03-15
DE4293959C2 (de)	1996-08-29
DE4293959T1 (de)	1995-01-26
GB9409758D0 (en)	1994-07-20
ES2070101A1 (es)	1995-05-16

Legal Events

Date	Code	Title
1996-04-01	BA	A request for search or an international-type search has been filed
1996-05-01	BC	A request for examination has been filed
1999-06-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US20080207912A1 (en)	2008-08-28	Method for manufacture of ceftiofur
FR2512448A1 (fr)	1983-03-11	Isoquinoleinium-betaines de cephalosporine et son application pharmaceutique
NL9220025A (nl)	1994-12-01	Werkwijze voor het bereiden van cephemderivaten.
EP0628561B1 (de)	1997-09-03	Verfahren zur Herstellung von Cephalosporinverbindungen aus reaktiven organischen Säurederivaten
KR20040008158A (ko)	2004-01-28	세프포독심 산의 제조 방법
US4145418A (en)	1979-03-20	Thienopyridine substituted cephalosporins
JPH05202060A (ja)	1993-08-10	ベータラクタム製造に関する改良法
JPH0461000B2 (de)	1992-09-29
DE3783048T2 (de)	1993-04-15	Verfahren zur herstellung von cephalosporinverbindungen.
KR930007260B1 (ko)	1993-08-04	세팔로스포린 유도체의 제조방법
KR0184037B1 (ko)	1999-05-01	세펨 유도체의 제조방법
EP0117872A1 (de)	1984-09-12	Herstellungsverfahren von cephalosporinverbindungen
US4137406A (en)	1979-01-30	Cephalosporins having a sulfur containing functional group in the 7-position side chain
KR0129567B1 (ko)	1998-04-09	반응성 유기산 유도체로부터 세팔로스포린 화합물의 제조방법
US4251657A (en)	1981-02-17	Method for removing protective groups
KR950013571B1 (ko)	1995-11-09	(6r, 7r)-7-[(z)-2-(2-아미노티아졸-4-일)-2-(2-카르복시프로프-2-옥시이미노)아세트아미도]-3-(1-피리디늄메틸)세프-3-엠-4-카르복실레이트 이염산염의 제조방법
CH627756A5 (en)	1982-01-29	Process for the preparation of 3-acyloxymethylcephem compounds
US4626533A (en)	1986-12-02	7-(2-thienylacetamido)-3-acylaminomethyl-cephalosporins
KR0139590B1 (ko)	1998-06-01	세펨 유도체의 제조방법
US5138049A (en)	1992-08-11	Cephalosporin derivative
KR0161796B1 (ko)	1998-12-01	티아졸릴 유도체의 제조방법
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