DE3035259C2 - Cephalosporinverbindungen, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten - Google Patents
Cephalosporinverbindungen, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthaltenInfo
- Publication number
- DE3035259C2 DE3035259C2 DE3035259A DE3035259A DE3035259C2 DE 3035259 C2 DE3035259 C2 DE 3035259C2 DE 3035259 A DE3035259 A DE 3035259A DE 3035259 A DE3035259 A DE 3035259A DE 3035259 C2 DE3035259 C2 DE 3035259C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- group
- general formula
- formula
- cefoperazone
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- -1 Cephalosporin compounds Chemical class 0.000 title claims description 16
- 229930186147 Cephalosporin Natural products 0.000 title claims description 8
- 229940124587 cephalosporin Drugs 0.000 title claims description 8
- 239000003814 drug Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- GCFBRXLSHGKWDP-XCGNWRKASA-N cefoperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC(O)=CC=1)C(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 GCFBRXLSHGKWDP-XCGNWRKASA-N 0.000 description 17
- 229960004682 cefoperazone Drugs 0.000 description 17
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- HJJDBAOLQAWBMH-YCRCPZNHSA-N cefmenoxime Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NN=NN1C HJJDBAOLQAWBMH-YCRCPZNHSA-N 0.000 description 7
- 229960003791 cefmenoxime Drugs 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
- 101000723013 Bacillus subtilis (strain 168) Probable cysteine synthase Proteins 0.000 description 4
- 101000965752 Sinorhizobium fredii (strain NBRC 101917 / NGR234) Putative cysteine synthase Proteins 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000085494 Pseudomonas aeruginosa E2 Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical group O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZIANDIUXHXXHLX-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C(O)=O)C(=O)N1 ZIANDIUXHXXHLX-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000589513 Burkholderia cepacia Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000122973 Stenotrophomonas maltophilia Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- YDROWRWAIBYYQX-FBLFFUNLSA-N benzhydryl (6r)-7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CN1N=NN=C1SCC1=C(C(=O)OC(C=2C=CC=CC=2)C=2C=CC=CC=2)N2C(=O)C(N)[C@H]2SC1 YDROWRWAIBYYQX-FBLFFUNLSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 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
- 229960001139 cefazolin Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11878879A JPS5643288A (en) | 1979-09-18 | 1979-09-18 | Cephalosporin derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3035259A1 DE3035259A1 (de) | 1981-03-19 |
| DE3035259C2 true DE3035259C2 (de) | 1986-03-13 |
Family
ID=14745096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3035259A Expired DE3035259C2 (de) | 1979-09-18 | 1980-09-18 | Cephalosporinverbindungen, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4393058A (enExample) |
| JP (1) | JPS5643288A (enExample) |
| AR (2) | AR227398A1 (enExample) |
| BE (1) | BE885265A (enExample) |
| CA (1) | CA1148142A (enExample) |
| DE (1) | DE3035259C2 (enExample) |
| ES (1) | ES8200113A1 (enExample) |
| FR (1) | FR2465739A1 (enExample) |
| GB (1) | GB2058769B (enExample) |
| IT (1) | IT1145390B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4758557A (en) * | 1985-06-26 | 1988-07-19 | Meiji Seika Kaisha, Ltd. | Cephalosporin derivatives and bactericides containing the same |
| US5254571A (en) * | 1988-04-21 | 1993-10-19 | Smith Kline & French Laboratories Ltd. | Chemical compounds |
| DE19500760A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Substituierte 2-Phenylpyridine |
| KR20030071311A (ko) * | 2002-02-28 | 2003-09-03 | 주식회사 엘지생명과학 | 신규 세팔로스포린 화합물 및 그의 제조방법 |
| JP4046708B2 (ja) * | 2004-06-04 | 2008-02-13 | 明治製菓株式会社 | ３−アルケニルセフェム化合物の製造方法 |
| US9650395B2 (en) | 2011-08-29 | 2017-05-16 | Ptc Therapeutics, Inc. | Antibacterial compounds and methods for use |
| JP2014525453A (ja) | 2011-08-29 | 2014-09-29 | ピーティーシー セラピューティクス， インコーポレイテッド | 抗菌化合物および使用方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS551273B2 (enExample) * | 1972-12-21 | 1980-01-12 | ||
| CA1074784A (en) * | 1974-09-06 | 1980-04-01 | Sumitomo Chemical Company | N-ACYLAMINO-.alpha.-ARYLACETAMIDO CEPHALOSPORINS |
| JPS5293790A (en) * | 1976-02-02 | 1977-08-06 | Sumitomo Chem Co Ltd | 7-(n-acylamino-alpha-arylacetamide) cephalosporins |
| US4302454A (en) * | 1976-03-03 | 1981-11-24 | Sumitomo Chemical Company, Limited | Cephalosporins |
| JPS5344585A (en) * | 1976-10-02 | 1978-04-21 | Meiji Seika Kaisha Ltd | Cephalosporin derivatives and their preparation |
| DE2658905A1 (de) * | 1976-12-24 | 1978-10-19 | Bayer Ag | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4101661A (en) * | 1977-06-03 | 1978-07-18 | Warner-Lambert | Novel antibacterial amide compounds and process means for producing the same |
| DE2924948A1 (de) * | 1979-06-21 | 1981-01-22 | Thomae Gmbh Dr K | Neue cephalosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1979
- 1979-09-18 JP JP11878879A patent/JPS5643288A/ja active Pending
-
1980
- 1980-09-12 GB GB8029630A patent/GB2058769B/en not_active Expired
- 1980-09-12 CA CA000360265A patent/CA1148142A/en not_active Expired
- 1980-09-16 AR AR282537A patent/AR227398A1/es active
- 1980-09-17 IT IT49684/80A patent/IT1145390B/it active
- 1980-09-17 FR FR8020008A patent/FR2465739A1/fr active Granted
- 1980-09-17 ES ES495137A patent/ES8200113A1/es not_active Expired
- 1980-09-17 BE BE0/202127A patent/BE885265A/fr not_active IP Right Cessation
- 1980-09-18 US US06/188,417 patent/US4393058A/en not_active Expired - Lifetime
- 1980-09-18 DE DE3035259A patent/DE3035259C2/de not_active Expired
-
1981
- 1981-12-10 AR AR287751A patent/AR227452A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| ES495137A0 (es) | 1981-10-16 |
| AR227452A1 (es) | 1982-10-29 |
| JPS5643288A (en) | 1981-04-21 |
| BE885265A (fr) | 1981-01-16 |
| GB2058769A (en) | 1981-04-15 |
| AR227398A1 (es) | 1982-10-29 |
| IT8049684A0 (it) | 1980-09-17 |
| FR2465739A1 (fr) | 1981-03-27 |
| DE3035259A1 (de) | 1981-03-19 |
| CA1148142A (en) | 1983-06-14 |
| IT1145390B (it) | 1986-11-05 |
| FR2465739B1 (enExample) | 1983-06-17 |
| ES8200113A1 (es) | 1981-10-16 |
| GB2058769B (en) | 1984-04-18 |
| US4393058A (en) | 1983-07-12 |
Similar Documents
| Publication | Publication Date | Title |
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