DE2155081B2 - 7- (lsoxazol-5-yl-acetamido)cephalosporansäurederivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen - Google Patents
7- (lsoxazol-5-yl-acetamido)cephalosporansäurederivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische ZusammensetzungenInfo
- Publication number
- DE2155081B2 DE2155081B2 DE2155081A DE2155081A DE2155081B2 DE 2155081 B2 DE2155081 B2 DE 2155081B2 DE 2155081 A DE2155081 A DE 2155081A DE 2155081 A DE2155081 A DE 2155081A DE 2155081 B2 DE2155081 B2 DE 2155081B2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- acetamido
- cephalosporanic acid
- isoxazol
- protons
- 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.)
- Granted
Links
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- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 4
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000002253 acid Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
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- 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 description 8
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- 229930186147 Cephalosporin Natural products 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5304070A GB1364453A (en) | 1970-11-06 | 1970-11-06 | Penicillanic and cepholosporanic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2155081A1 DE2155081A1 (de) | 1972-05-10 |
| DE2155081B2 true DE2155081B2 (de) | 1975-05-15 |
| DE2155081C3 DE2155081C3 (enrdf_load_stackoverflow) | 1975-12-18 |
Family
ID=10466394
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2155081A Granted DE2155081B2 (de) | 1970-11-06 | 1971-11-05 | 7- (lsoxazol-5-yl-acetamido)cephalosporansäurederivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
| DE19712166468 Pending DE2166468A1 (de) | 1970-11-06 | 1971-11-05 | Neue isoxazolylderivate und verfahren zu deren herstellung |
| DE19712166467 Pending DE2166467A1 (de) | 1970-11-06 | 1971-11-05 | Neue penicillansaeurederivate, deren herstellungsverfahren und diese enthaltende pharmazeutische zusammensetzungen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712166468 Pending DE2166468A1 (de) | 1970-11-06 | 1971-11-05 | Neue isoxazolylderivate und verfahren zu deren herstellung |
| DE19712166467 Pending DE2166467A1 (de) | 1970-11-06 | 1971-11-05 | Neue penicillansaeurederivate, deren herstellungsverfahren und diese enthaltende pharmazeutische zusammensetzungen |
Country Status (14)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1459392A (en) * | 1972-12-22 | 1976-12-22 | Gist Brocades Nv | Heterocyclic compounds |
| AU6620274A (en) * | 1973-03-02 | 1975-09-04 | Gist Brocades Nv | Penicillanic and cephalosporanic acid derivatives |
| JPS5760345B2 (enrdf_load_stackoverflow) * | 1974-12-19 | 1982-12-18 | Takeda Chemical Industries Ltd | |
| 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 |
| CA1088049A (en) * | 1975-06-03 | 1980-10-21 | Takashi Masugi | 3-substituted-7-substituted alkanamido-3-cephem-4- carboxylic acid compounds and processes for preparation thereof |
| MD227C2 (ro) * | 1976-01-23 | 1995-11-30 | Roussel Uclaf, Societe Anonyme | Procedeu de obţinere a derivaţilor acidului 7-(2-(2-aminotiazolil-4)-2-oxiiminoacetamido)-3-acetoximetil-3-cefem- 4-carbonic sub formă de sin-izomeri |
| JPS6052713B2 (ja) * | 1978-04-11 | 1985-11-20 | 三共株式会社 | ７−メトキシセフアロスポリン化合物、その製法及びその化合物を主成分とする抗菌剤 |
| CA1128526A (en) * | 1979-10-05 | 1982-07-27 | Cdc Life Sciences Inc. | 3,4-diarylisoxazol-5-acetic acids |
| US4526977A (en) * | 1981-10-07 | 1985-07-02 | American Home Products Corporation | 2-(3-Amino-5-isoxazolyl)-2-oxyimino-acetic acids |
| JPS60141367U (ja) * | 1984-02-29 | 1985-09-19 | タキロン株式会社 | 天窓のロツク装置 |
| US4562187A (en) * | 1985-01-22 | 1985-12-31 | Hoechst-Roussel Pharmaceuticals Inc. | (Isoxazol-3-yl)arylmethanones, compositions and pharmaceutical use |
| US7427680B2 (en) * | 2001-01-12 | 2008-09-23 | The Regents Of The University Of California | Fluorogenic substrates for BETA-lactamase gene expression |
| AU2002251755C1 (en) * | 2001-01-12 | 2008-07-10 | The Regents Of The University Of California | Beta-lactamase substrates having phenolic ethers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3218318A (en) * | 1962-08-31 | 1965-11-16 | Lilly Co Eli | 7-heterocyclic-substituted-acylamido cephalosporins |
| US3459746A (en) * | 1965-10-04 | 1969-08-05 | Lilly Co Eli | 7 - heteromonocyclic-substituted acylamido derivatives of desacetyl cephalosporanic acid |
-
1970
- 1970-11-06 GB GB5304070A patent/GB1364453A/en not_active Expired
-
1971
- 1971-11-03 US US195482A patent/US3891635A/en not_active Expired - Lifetime
- 1971-11-05 BE BE775012A patent/BE775012A/xx unknown
- 1971-11-05 DE DE2155081A patent/DE2155081B2/de active Granted
- 1971-11-05 ZA ZA717433A patent/ZA717433B/xx unknown
- 1971-11-05 HU HUKO2471A patent/HU162822B/hu unknown
- 1971-11-05 NL NL717115231A patent/NL150117B/xx unknown
- 1971-11-05 DE DE19712166468 patent/DE2166468A1/de active Pending
- 1971-11-05 FR FR7139822A patent/FR2112504B1/fr not_active Expired
- 1971-11-05 CH CH1400275A patent/CH572935A5/xx not_active IP Right Cessation
- 1971-11-05 SU SU1713952A patent/SU520050A3/ru active
- 1971-11-05 DE DE19712166467 patent/DE2166467A1/de active Pending
- 1971-11-05 AU AU35431/71A patent/AU463230B2/en not_active Expired
- 1971-11-05 CA CA126,985A patent/CA983920A/en not_active Expired
- 1971-11-05 CH CH1616271A patent/CH573436A5/xx not_active IP Right Cessation
- 1971-11-05 JP JP46088177A patent/JPS5212200B1/ja active Pending
- 1971-11-05 ES ES396720A patent/ES396720A1/es not_active Expired
- 1971-11-05 CH CH1400375A patent/CH572936A5/xx not_active IP Right Cessation
-
1974
- 1974-03-01 ES ES423795A patent/ES423795A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH573436A5 (enrdf_load_stackoverflow) | 1976-03-15 |
| SU520050A3 (ru) | 1976-06-30 |
| AU463230B2 (en) | 1975-07-17 |
| GB1364453A (en) | 1974-08-21 |
| ZA717433B (en) | 1972-07-26 |
| JPS5212200B1 (enrdf_load_stackoverflow) | 1977-04-05 |
| CH572936A5 (enrdf_load_stackoverflow) | 1976-02-27 |
| DE2166467A1 (de) | 1974-02-14 |
| DE2166468A1 (de) | 1974-02-14 |
| US3891635A (en) | 1975-06-24 |
| HU162822B (enrdf_load_stackoverflow) | 1973-04-28 |
| BE775012A (fr) | 1972-05-05 |
| CH572935A5 (enrdf_load_stackoverflow) | 1976-02-27 |
| FR2112504B1 (enrdf_load_stackoverflow) | 1975-10-31 |
| ES396720A1 (es) | 1975-04-16 |
| CA983920A (en) | 1976-02-17 |
| NL7115231A (enrdf_load_stackoverflow) | 1972-05-09 |
| ES423795A1 (es) | 1976-12-16 |
| DE2155081A1 (de) | 1972-05-10 |
| NL150117B (nl) | 1976-07-15 |
| AU3543171A (en) | 1973-05-10 |
| FR2112504A1 (enrdf_load_stackoverflow) | 1972-06-16 |
| DE2155081C3 (enrdf_load_stackoverflow) | 1975-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |