ES472335A1 - Process for the preparation of ethers of clavulanic acid. - Google Patents
Process for the preparation of ethers of clavulanic acid.Info
- Publication number
- ES472335A1 ES472335A1 ES472335A ES472335A ES472335A1 ES 472335 A1 ES472335 A1 ES 472335A1 ES 472335 A ES472335 A ES 472335A ES 472335 A ES472335 A ES 472335A ES 472335 A1 ES472335 A1 ES 472335A1
- Authority
- ES
- Spain
- Prior art keywords
- preparation
- clavulanic acid
- ethers
- esters
- salts
- 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
- 238000000034 method Methods 0.000 title abstract 4
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 title abstract 3
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 title abstract 3
- 229960003324 clavulanic acid Drugs 0.000 title abstract 3
- 150000002170 ethers Chemical class 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical class CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical group C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract 1
- 108090000204 Dipeptidase 1 Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 102000006635 beta-lactamase Human genes 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
This invention provides a process for the preparation of the ethyl and propyl ethers of clavulanic acid and salts and esters thereof, which process comprises the reduction of an ester of a compound of the formula (II): < CHEM > wherein R2 is a CH = CH2 or CH = CHCH3 group, and thereafter or simultaneously, if desired, converting the thus-formed ester of the ethyl or propyl ether of clavulanic acid to the corresponding acid or a salt thereof. The compounds of the formula (II) and salts and esters thereof are novel and have beta -lactamase inhibitory properties, and this invention further provides these compounds, a process for their preparation, and pharmaceutical compositions containing them.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3269977 | 1977-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES472335A1 true ES472335A1 (en) | 1980-03-01 |
Family
ID=10342695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES472335A Expired ES472335A1 (en) | 1977-08-04 | 1978-08-03 | Process for the preparation of ethers of clavulanic acid. |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0000804B1 (en) |
| JP (1) | JPS5427595A (en) |
| CA (1) | CA1107739A (en) |
| DE (1) | DE2862385D1 (en) |
| ES (1) | ES472335A1 (en) |
| IT (1) | IT1106618B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1501643A (en) * | 1974-10-28 | 1978-02-22 | Beecham Group Ltd | Antibacterial substituted azetidinones |
| GB1565209A (en) * | 1975-10-13 | 1980-04-16 | Beecham Group Ltd | Clavulanic acid derivatives |
| US4230622A (en) * | 1975-12-17 | 1980-10-28 | Glaxo Laboratories Limited | Halogen derivatives of clavulaic acid |
-
1978
- 1978-07-10 EP EP78300135A patent/EP0000804B1/en not_active Expired
- 1978-07-10 DE DE7878300135T patent/DE2862385D1/en not_active Expired
- 1978-07-27 CA CA308,302A patent/CA1107739A/en not_active Expired
- 1978-08-01 JP JP9501178A patent/JPS5427595A/en active Pending
- 1978-08-02 IT IT50575/78A patent/IT1106618B/en active
- 1978-08-03 ES ES472335A patent/ES472335A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5427595A (en) | 1979-03-01 |
| CA1107739A (en) | 1981-08-25 |
| IT7850575A0 (en) | 1978-08-02 |
| IT1106618B (en) | 1985-11-11 |
| DE2862385D1 (en) | 1984-04-12 |
| EP0000804A1 (en) | 1979-02-21 |
| EP0000804B1 (en) | 1984-03-07 |
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