IE42370L - Isoclavulanic acid derivatives - Google Patents
Isoclavulanic acid derivativesInfo
- Publication number
- IE42370L IE42370L IE752645A IE264575A IE42370L IE 42370 L IE42370 L IE 42370L IE 752645 A IE752645 A IE 752645A IE 264575 A IE264575 A IE 264575A IE 42370 L IE42370 L IE 42370L
- Authority
- IE
- Ireland
- Prior art keywords
- hydrogen
- group
- carbon atoms
- hydrocarbon group
- derivatives
- Prior art date
Links
- HZZVJAQRINQKSD-INJCQMSSSA-N Isoclavulanic acid Chemical class OC(=O)[C@H]1C(=C/CO)\O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-INJCQMSSSA-N 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 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 abstract 1
- 229960003324 clavulanic acid Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Isoclavulanic acid and derivatives of it are disclosed which have .beta.-lactamase inhibitory and antibacterial properties, the preferred compounds being of the formula (I) wherein R is hydrogen or wherein n is 0 or an integer from 1 to 6; R1 is a hydrogen or a phenol or phenoxy group and R2 is a hydrogen or halogen atom or a C1-4 alkyl, C1-4 alkoxy, -CO2R3 group where R3 is a hydrocarbon group of 1-8 carbon atoms or ; or pharmaceutically acceptable salts thereof of the group of sodium, potassium, calcium, magnesium and aluminum; or pharmaceutically acceptable esters thereof of the formula . wherein A is a hydrocarbon group of 1 to 9 carbon atoms or a hydrocarbon group of 1 to 9 carbon atoms substituted by one or more halogen, lower alkyl, lower acyl, lower etherified or acylated hydroxy groups. These compounds are prepared by isomerization of clavulanic acid or derivatives, for example in the presence of a transition metal catalyst and hydrogen, or by ultra-violet irradiation.
[CA1064039A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB54788/74A GB1534508A (en) | 1974-12-18 | 1974-12-18 | Isoclavulanic acid derivatives |
| GB1521175 | 1975-04-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42370L true IE42370L (en) | 1976-06-18 |
| IE42370B1 IE42370B1 (en) | 1980-07-30 |
Family
ID=26251138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2645/75A IE42370B1 (en) | 1974-12-18 | 1975-12-04 | Isoclavulanic acid derivatives |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS51138693A (en) |
| AU (1) | AU500572B2 (en) |
| CA (1) | CA1064039A (en) |
| CH (1) | CH619230A5 (en) |
| DE (1) | DE2555626A1 (en) |
| DK (1) | DK142702B (en) |
| FR (1) | FR2294701A1 (en) |
| IE (1) | IE42370B1 (en) |
| IL (1) | IL48607A (en) |
| NL (1) | NL7514545A (en) |
| SE (1) | SE428564B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53116395A (en) * | 1976-10-25 | 1978-10-11 | Glaxo Lab Ltd | Novel antibiotics and process for preparing same |
| GB1587612A (en) * | 1976-10-30 | 1981-04-08 | Beecham Group Ltd | Isoclavulanic acid derivatives |
-
1975
- 1975-12-04 IE IE2645/75A patent/IE42370B1/en unknown
- 1975-12-05 IL IL48607A patent/IL48607A/en unknown
- 1975-12-10 DE DE19752555626 patent/DE2555626A1/en not_active Withdrawn
- 1975-12-11 SE SE7514029A patent/SE428564B/en unknown
- 1975-12-12 AU AU87521/75A patent/AU500572B2/en not_active Expired
- 1975-12-12 NL NL7514545A patent/NL7514545A/en not_active Application Discontinuation
- 1975-12-15 FR FR7538284A patent/FR2294701A1/en active Granted
- 1975-12-17 DK DK574875AA patent/DK142702B/en unknown
- 1975-12-17 CH CH1634675A patent/CH619230A5/en not_active IP Right Cessation
- 1975-12-17 CA CA241,930A patent/CA1064039A/en not_active Expired
- 1975-12-18 JP JP50152683A patent/JPS51138693A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2294701A1 (en) | 1976-07-16 |
| JPS51138693A (en) | 1976-11-30 |
| IL48607A (en) | 1979-07-25 |
| DK142702B (en) | 1980-12-22 |
| SE428564B (en) | 1983-07-11 |
| CH619230A5 (en) | 1980-09-15 |
| SE7514029L (en) | 1976-06-21 |
| CA1064039A (en) | 1979-10-09 |
| FR2294701B1 (en) | 1982-07-23 |
| DK142702C (en) | 1981-08-10 |
| DK574875A (en) | 1976-06-19 |
| IE42370B1 (en) | 1980-07-30 |
| DE2555626A1 (en) | 1976-07-01 |
| AU500572B2 (en) | 1979-05-24 |
| IL48607A0 (en) | 1976-02-29 |
| NL7514545A (en) | 1976-06-22 |
| AU8752175A (en) | 1977-06-16 |
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