SE505050C2 - Process för framställning av cephemderivat - Google Patents
Process för framställning av cephemderivatInfo
- Publication number
- SE505050C2 SE505050C2 SE9401706A SE9401706A SE505050C2 SE 505050 C2 SE505050 C2 SE 505050C2 SE 9401706 A SE9401706 A SE 9401706A SE 9401706 A SE9401706 A SE 9401706A SE 505050 C2 SE505050 C2 SE 505050C2
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- mixture
- give
- added
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 150000001782 cephems Chemical class 0.000 title description 2
- -1 acetoxy methyl Chemical group 0.000 claims abstract description 31
- 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 abstract description 21
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001805 chlorine compounds Chemical class 0.000 claims abstract description 11
- 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 abstract description 10
- 238000002955 isolation Methods 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 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 claims description 6
- 230000010933 acylation Effects 0.000 claims description 5
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002184 metal Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 239000013078 crystal Substances 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 239000012046 mixed solvent Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 150000003952 β-lactams Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000006884 silylation reaction Methods 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- 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 2
- 239000012467 final product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- ASGIQPRGHDBJBR-XCGJVMPOSA-N (6r)-4-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1C=C(C(O)=O)N2C(=O)C[C@H]2S1 ASGIQPRGHDBJBR-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
- 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 1
- 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 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 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
- 230000007547 defect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- ASWXNYNXAOQCCD-UHFFFAOYSA-N dichloro(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Cl)(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 ASWXNYNXAOQCCD-UHFFFAOYSA-N 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
- 238000009413 insulation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 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)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9401706D0 SE9401706D0 (sv) | 1994-05-18 |
| SE9401706L SE9401706L (sv) | 1994-07-07 |
| SE505050C2 true SE505050C2 (sv) | 1997-06-16 |
Family
ID=19322986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9401706A SE505050C2 (sv) | 1991-11-18 | 1994-05-18 | Process för framställning av cephemderivat |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5317099A (ko) |
| EP (1) | EP0613480B1 (ko) |
| JP (1) | JPH0811755B2 (ko) |
| KR (1) | KR950014571B1 (ko) |
| AT (1) | AT403048B (ko) |
| CH (1) | CH684091A5 (ko) |
| DE (2) | DE4293959C2 (ko) |
| DK (1) | DK56694A (ko) |
| ES (1) | ES2070101B1 (ko) |
| GB (1) | GB2275927B (ko) |
| NL (1) | NL9220025A (ko) |
| SE (1) | SE505050C2 (ko) |
| WO (1) | WO1993010123A1 (ko) |
Families Citing this family (6)
| 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 (ko) * | 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| US4196205A (en) * | 1976-01-23 | 1980-04-01 | Roussel Uclaf | 3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives |
| 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 |
| DE2760484C2 (ko) * | 1976-04-14 | 1992-12-03 | Takeda Chemical Industries, Ltd., Osaka, Jp | |
| 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 |
| CY1365A (en) * | 1980-03-28 | 1987-08-07 | 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 |
| ATE155469T1 (de) * | 1988-03-16 | 1997-08-15 | Eisai Co Ltd | Verfahren zur herstellung von cephemderivaten |
| 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 IP Right Cessation
-
1992
- 1992-09-04 AT AT0903092A patent/AT403048B/de not_active IP Right Cessation
- 1992-09-04 EP EP92919241A patent/EP0613480B1/en not_active Expired - Lifetime
- 1992-09-04 DE DE4293959A patent/DE4293959C2/de not_active Expired - Fee Related
- 1992-09-04 WO PCT/KR1992/000041 patent/WO1993010123A1/en active IP Right Grant
- 1992-09-04 CH CH2208/93A patent/CH684091A5/de not_active IP Right Cessation
- 1992-09-04 NL NL9220025A patent/NL9220025A/nl not_active Application Discontinuation
- 1992-09-04 JP JP5509158A patent/JPH0811755B2/ja not_active Expired - Fee Related
- 1992-09-04 GB GB9409758A patent/GB2275927B/en not_active Expired - Fee Related
- 1992-09-04 DE DE4293959T patent/DE4293959T1/de active Pending
- 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 |
|---|---|
| NL9220025A (nl) | 1994-12-01 |
| ATA903092A (de) | 1997-03-15 |
| SE9401706D0 (sv) | 1994-05-18 |
| US5317099A (en) | 1994-05-31 |
| KR930010043A (ko) | 1993-06-21 |
| JPH0811755B2 (ja) | 1996-02-07 |
| WO1993010123A1 (en) | 1993-05-27 |
| CH684091A5 (de) | 1994-07-15 |
| EP0613480B1 (en) | 1999-03-31 |
| EP0613480A1 (en) | 1994-09-07 |
| DE4293959T1 (de) | 1995-01-26 |
| KR950014571B1 (ko) | 1995-12-08 |
| ES2070101A1 (es) | 1995-05-16 |
| GB2275927B (en) | 1995-10-04 |
| AT403048B (de) | 1997-10-27 |
| JPH07501072A (ja) | 1995-02-02 |
| GB2275927A (en) | 1994-09-14 |
| GB9409758D0 (en) | 1994-07-20 |
| SE9401706L (sv) | 1994-07-07 |
| ES2070101B1 (es) | 1996-02-16 |
| DK56694A (da) | 1994-05-18 |
| DE4293959C2 (de) | 1996-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |