DE2560655C2 - - Google Patents
Info
- Publication number
- DE2560655C2 DE2560655C2 DE2560655A DE2560655A DE2560655C2 DE 2560655 C2 DE2560655 C2 DE 2560655C2 DE 2560655 A DE2560655 A DE 2560655A DE 2560655 A DE2560655 A DE 2560655A DE 2560655 C2 DE2560655 C2 DE 2560655C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- thiol
- mercaptotetrazole
- treated
- crystals
- 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
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- -1 Tetrazole compounds Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000002641 lithium Chemical class 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 150000007970 thio esters Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- QEFGDOJRWHUFNH-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)acetic acid Chemical compound OC(=O)CSC=1N=NNN=1 QEFGDOJRWHUFNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002900 organolithium compounds Chemical class 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000013078 crystal Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- UOTQEHLQKASWQO-UHFFFAOYSA-N 2-(5-sulfanylidene-2h-tetrazol-1-yl)acetic acid Chemical compound OC(=O)CN1N=NN=C1S UOTQEHLQKASWQO-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000002024 ethyl acetate extract Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- VBWYAKMJWHGBIV-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)propanoic acid Chemical compound OC(=O)C(C)SC1=NN=NN1 VBWYAKMJWHGBIV-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- XBSGYVHOINMTIM-UHFFFAOYSA-N ethyl 3-isocyanatopropanoate Chemical compound CCOC(=O)CCN=C=O XBSGYVHOINMTIM-UHFFFAOYSA-N 0.000 description 2
- 210000002196 fr. b Anatomy 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- KPTNUCBVMWICQI-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione;sodium Chemical compound [Na].CN1NN=NC1=S KPTNUCBVMWICQI-UHFFFAOYSA-N 0.000 description 1
- RDHBKRQOSVEWGC-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)butanoic acid Chemical compound CCC(C(O)=O)SC1=NN=NN1 RDHBKRQOSVEWGC-UHFFFAOYSA-N 0.000 description 1
- CTXRELZEQZUMNY-UHFFFAOYSA-N 2-(2h-tetrazol-5-ylsulfanyl)pentanoic acid Chemical compound CCCC(C(O)=O)SC1=NN=NN1 CTXRELZEQZUMNY-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- MFXACNVJZDZTTB-UHFFFAOYSA-N [Na].[Na].C(=O)(O)N1N(NN=C1S)C Chemical compound [Na].[Na].C(=O)(O)N1N(NN=C1S)C MFXACNVJZDZTTB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- RJCGNNHKSNIUAT-UHFFFAOYSA-N ethyl 3-aminopropanoate;hydron;chloride Chemical compound Cl.CCOC(=O)CCN RJCGNNHKSNIUAT-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50299174A | 1974-09-03 | 1974-09-03 | |
| US05/590,971 US4297489A (en) | 1974-09-03 | 1975-06-27 | 7-α-Amino-substituted acylamino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2560655C2 true DE2560655C2 (en, 2012) | 1988-07-14 |
Family
ID=27054342
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2560655A Expired DE2560655C2 (en, 2012) | 1974-09-03 | 1975-09-01 | |
| DE2538804A Expired DE2538804C2 (de) | 1974-09-03 | 1975-09-01 | Cephalosporinderivate, Verfahren zu ihrer Herstellung und sie enthaltende Mittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2538804A Expired DE2538804C2 (de) | 1974-09-03 | 1975-09-01 | Cephalosporinderivate, Verfahren zu ihrer Herstellung und sie enthaltende Mittel |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4297489A (en, 2012) |
| JP (1) | JPS6150956B2 (en, 2012) |
| AR (1) | AR222771A1 (en, 2012) |
| BG (1) | BG27091A3 (en, 2012) |
| CA (4) | CA1135255A (en, 2012) |
| CH (1) | CH636882A5 (en, 2012) |
| DD (2) | DD123471A5 (en, 2012) |
| DE (2) | DE2560655C2 (en, 2012) |
| DK (4) | DK145262C (en, 2012) |
| ES (2) | ES440707A1 (en, 2012) |
| FI (1) | FI62841C (en, 2012) |
| FR (1) | FR2283686A1 (en, 2012) |
| HU (1) | HU169490B (en, 2012) |
| IE (1) | IE43123B1 (en, 2012) |
| IL (1) | IL48020A (en, 2012) |
| LU (1) | LU73306A1 (en, 2012) |
| NL (1) | NL161758C (en, 2012) |
| NO (1) | NO152509C (en, 2012) |
| OA (1) | OA05096A (en, 2012) |
| SE (3) | SE431548B (en, 2012) |
| YU (5) | YU213275A (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4286089A (en) * | 1974-12-27 | 1981-08-25 | Smithkline Corporation | 7-Acyl-3-(substituted tetrazolyl thiomethyl)cephalosporins |
| US4101656A (en) * | 1976-07-12 | 1978-07-18 | Smithkline Corporation | 7β-Acylamino-3-(alkanesulfonamidoalkyl substituted tetrazolylthiomethyl) cephalosporins, antibacterial compositions containing them and methods of treating bacterial infections with them |
| US4278670A (en) * | 1976-07-12 | 1981-07-14 | Smithkline Corporation | 7-Alpha-oxyiminoacylcephalosporins |
| DE2724092A1 (de) * | 1977-05-27 | 1978-12-07 | Smithkline Corp | Cephalosporine, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| FR2387235A1 (fr) * | 1978-01-23 | 1978-11-10 | Fujisawa Pharmaceutical Co | Procede de preparation de composes d'acide 3,7-disubstitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, ayant une forte activite antibacterienne |
| US4374994A (en) * | 1979-07-05 | 1983-02-22 | Bristol-Myers Company | Process for preparation of 5-mercaptotetrazolyl-1-acetic acid |
| US4243803A (en) * | 1979-07-05 | 1981-01-06 | Bristol-Myers Company | Production of 7-(2-aminomethylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
| EP0095029B1 (en) * | 1979-11-30 | 1986-11-05 | Fujisawa Pharmaceutical Co., Ltd. | 5-thio-tetrazol compounds and their preparation |
| JPS56158791A (en) * | 1980-05-10 | 1981-12-07 | Taisho Pharmaceut Co Ltd | Cephalosporin compound |
| IL63767A0 (en) * | 1980-09-17 | 1981-12-31 | Lilly Co Eli | Cephalosporin compounds |
| JPS57188594A (en) * | 1981-05-15 | 1982-11-19 | Eisai Co Ltd | Preparation of 7-(2-amino-2-phenylacetamido)cephem derivative |
| US4448958A (en) * | 1982-10-20 | 1984-05-15 | Bristol-Myers Company | Purification of ceforanide |
| US4749522A (en) * | 1985-10-31 | 1988-06-07 | Angio-Medical Corporation | Supercritical fluid extraction of animal derived materials |
| DE3641822A1 (de) * | 1986-12-06 | 1988-06-16 | Goedecke Ag | Verwendung von dihydrophenylaminosaeurederivaten und diese enthaltende arzneimittel zur immunmodulation und cytostase |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1953861A1 (de) * | 1969-10-25 | 1971-05-06 | Fujisawa Pharmaceutical Co | Neue 3,7-disubstituierte Cephalosporin-Derivate |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819623A (en) * | 1968-04-12 | 1974-06-25 | Fujisawa Pharmaceutical Co | 3,7-disubstituted cephalosporin compounds |
| US3814755A (en) * | 1972-08-30 | 1974-06-04 | Bristol Myers Co | 7-(omikron-aminomethylphenylacetamido)-3-(tetrazolo(4,5-b)pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid |
| GB1478055A (en) | 1973-07-27 | 1977-06-29 | Erba Carlo Spa | Cephalosporin compounds |
| US4074929A (en) | 1973-08-29 | 1978-02-21 | Amp Incorporated | Cable card edge connector |
| NL7414119A (nl) * | 1973-10-31 | 1975-05-02 | Fujisawa Pharmaceutical Co | Werkwijze ter bereiding van 1h-tetrazool-5-thiol- derivaten en 1-gesubstitueerde 1h-tetrazool- -5-thiolen. |
| US4205166A (en) * | 1974-02-20 | 1980-05-27 | Fujisawa Pharmaceutical Co., Ltd. | 7-Substituted-3-aminoalkyl-, acylaminoalkyl-, or hydroxyalkyl-substituted heterocyclic thiomethyl-3-cephem-4-carboxylic acid derivatives and preparation thereof |
| US4092476A (en) * | 1974-02-21 | 1978-05-30 | Beecham Group Limited | Phthalidyl esters of 7-[(α amino, 2 substituted acetamido)-3-(heterocyclic-thio methyl)]cephalosporins |
| US4068074A (en) * | 1974-04-05 | 1978-01-10 | Yamanouchi Pharmaceutical Co., Ltd. | Cephalosporin derivatives having at the 3-position of the cephem ring a heterocyclic thiomethyl group with a carboxy or sulfo group and at the 7-position of the cephem ring an α-heterocylic acylaminophenyl-acetamide group |
| US4160086A (en) * | 1974-04-27 | 1979-07-03 | Beecham Group Limited | 3-Heterocyclicthio-7-α-carboxy 2-aryl acetamido cephalosporanic acid |
| JPS612674B2 (en, 2012) * | 1974-06-20 | 1986-01-27 | Meiji Seika Co | |
| US4172196A (en) * | 1974-09-03 | 1979-10-23 | Bristol-Myers Company | Certain 7-α-substituted-α-hydroxyacetamido-3-(1-carboxymethyltetrazol-5-yl-thiomethyl)-3-cephem-4-carboxylic acids |
| US4182863A (en) * | 1974-09-03 | 1980-01-08 | Bristol-Myers Company | 7-Amino-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US4286089A (en) * | 1974-12-27 | 1981-08-25 | Smithkline Corporation | 7-Acyl-3-(substituted tetrazolyl thiomethyl)cephalosporins |
| US4183925A (en) * | 1975-03-27 | 1980-01-15 | Pfizer Inc. | 7-Aminophenylacetamido-Δ3 -cephem antibacterial agents and method of use |
| JPS525787A (en) * | 1975-06-27 | 1977-01-17 | Bristol Myers Co | Antiibacterial agent |
| US4013648A (en) * | 1975-07-23 | 1977-03-22 | Bristol-Myers Company | Δ2,3 -0-2-Isocephem-4-carboxylic acid and derivatives as antibacterial agents |
| US4220644A (en) * | 1976-05-03 | 1980-09-02 | Smithkline Corporation | 7-Acylamino-3-(substituted tetrazolyl thiomethyl) cephalosporins |
| US4118563A (en) * | 1977-11-25 | 1978-10-03 | Bristol-Myers Company | Production of 7-(2-aminomethylphenylacetamido-3-(1-carboxymethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
-
1975
- 1975-06-27 US US05/590,971 patent/US4297489A/en not_active Expired - Lifetime
- 1975-08-21 YU YU02132/75A patent/YU213275A/xx unknown
- 1975-08-27 CA CA000234276A patent/CA1135255A/en not_active Expired
- 1975-08-29 FI FI752434A patent/FI62841C/fi not_active IP Right Cessation
- 1975-08-29 DK DK391075A patent/DK145262C/da not_active IP Right Cessation
- 1975-09-01 DE DE2560655A patent/DE2560655C2/de not_active Expired
- 1975-09-01 BG BG030902A patent/BG27091A3/xx unknown
- 1975-09-01 IL IL48020A patent/IL48020A/xx unknown
- 1975-09-01 SE SE7509702A patent/SE431548B/xx not_active IP Right Cessation
- 1975-09-01 NO NO752983A patent/NO152509C/no unknown
- 1975-09-01 DE DE2538804A patent/DE2538804C2/de not_active Expired
- 1975-09-02 LU LU73306A patent/LU73306A1/xx unknown
- 1975-09-02 FR FR7526936A patent/FR2283686A1/fr active Granted
- 1975-09-02 HU HUBI521A patent/HU169490B/hu unknown
- 1975-09-02 OA OA55597A patent/OA05096A/xx unknown
- 1975-09-03 ES ES440707A patent/ES440707A1/es not_active Expired
- 1975-09-03 IE IE1916/75A patent/IE43123B1/en unknown
- 1975-09-03 NL NL7510391.A patent/NL161758C/xx active
- 1975-09-03 JP JP50106106A patent/JPS6150956B2/ja not_active Expired
- 1975-09-03 AR AR260237A patent/AR222771A1/es active
- 1975-09-03 DD DD188166A patent/DD123471A5/xx unknown
- 1975-09-03 DD DD7500196946A patent/DD130787A5/xx unknown
-
1977
- 1977-04-20 ES ES457998A patent/ES457998A1/es not_active Expired
-
1979
- 1979-08-31 DK DK367279A patent/DK147483C/da active
- 1979-09-14 SE SE7907672A patent/SE435279B/sv not_active IP Right Cessation
-
1980
- 1980-12-02 CH CH890980A patent/CH636882A5/de not_active IP Right Cessation
-
1981
- 1981-03-12 CA CA372,810A patent/CA1123840A/en not_active Expired
- 1981-03-12 CA CA000372811A patent/CA1135254A/en not_active Expired
- 1981-08-24 CA CA000384513A patent/CA1135256A/en not_active Expired
- 1981-09-16 YU YU2231/81A patent/YU44964B/xx unknown
- 1981-09-16 YU YU02230/81A patent/YU223081A/xx unknown
- 1981-09-16 YU YU2232/81A patent/YU44669B/xx unknown
- 1981-09-16 YU YU2233/81A patent/YU44833B/xx unknown
-
1982
- 1982-05-27 DK DK240582A patent/DK148796C/da not_active IP Right Cessation
-
1983
- 1983-09-16 DK DK423383A patent/DK162388C/da active
- 1983-10-07 SE SE8305539A patent/SE453507B/sv not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1953861A1 (de) * | 1969-10-25 | 1971-05-06 | Fujisawa Pharmaceutical Co | Neue 3,7-disubstituierte Cephalosporin-Derivate |
Non-Patent Citations (1)
| Title |
|---|
| J. Med. Chem., 17 (1974), 34 * |
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