IE801963L - Penicillanic acid derivatives - Google Patents
Penicillanic acid derivativesInfo
- Publication number
- IE801963L IE801963L IE801963A IE196380A IE801963L IE 801963 L IE801963 L IE 801963L IE 801963 A IE801963 A IE 801963A IE 196380 A IE196380 A IE 196380A IE 801963 L IE801963 L IE 801963L
- Authority
- IE
- Ireland
- Prior art keywords
- carboxy group
- acid derivatives
- penicillanic acid
- antibiotics
- stands
- Prior art date
Links
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 title abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 229940088710 antibiotic agent Drugs 0.000 abstract 2
- 239000003781 beta lactamase inhibitor Substances 0.000 abstract 2
- 229940126813 beta-lactamase inhibitor Drugs 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003413 degradative effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 150000003462 sulfoxides Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
- 239000010937 tungsten Substances 0.000 abstract 1
Classifications
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds of the formula I <IMAGE> in which R1 stands for hydrogen, alkyl, alkoxy, halogen, or trifluoromethyl, and R2 stands for a carboxy group or for a protected carboxy group, in particular an esterified carboxy group; or, if appropriate, a salt thereof, are obtained by oxidising the corresponding penicillanic acid derivatives or their sulfoxides with hydrogen peroxide in the presence of a tungsten or molybdenum catalyst. This process eliminates secondary degradative oxidative side reactions and simplifies the isolation and purification of the product, thus providing high yields and thereby being particularly suited for large scale production. The compounds of formula I, depending upon the meanings of R1 and R2, are of value as beta -lactamase inhibitors and/or antibiotics, and/or as intermediates in the production of antibiotics and/or beta -lactamase inhibitors.
[GB2059960A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7935284 | 1979-10-11 | ||
| GB7942062 | 1979-12-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE801963L true IE801963L (en) | 1981-04-11 |
| IE50650B1 IE50650B1 (en) | 1986-06-11 |
Family
ID=26273161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1963/80A IE50650B1 (en) | 1979-10-11 | 1980-09-22 | Method for producing penicillanic acid derivatives |
Country Status (11)
| Country | Link |
|---|---|
| CA (1) | CA1142174A (en) |
| CH (1) | CH646174A5 (en) |
| DE (1) | DE3037896A1 (en) |
| DK (1) | DK154085C (en) |
| FR (1) | FR2467210A1 (en) |
| GB (1) | GB2059960B (en) |
| IE (1) | IE50650B1 (en) |
| IT (1) | IT1132938B (en) |
| LU (1) | LU82842A1 (en) |
| NL (1) | NL8005626A (en) |
| SE (1) | SE449613B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4331599A (en) * | 1981-02-02 | 1982-05-25 | Pfizer Inc. | Sparingly water-soluble salts of penicillanic acid 1,1-dioxide |
| IN159362B (en) * | 1981-03-23 | 1987-05-09 | Pfizer | |
| US4381263A (en) * | 1981-03-23 | 1983-04-26 | Pfizer Inc. | Process for the preparation of penicillanic acid esters |
| US4502988A (en) * | 1983-08-08 | 1985-03-05 | Eli Lilly And Company | Oxidation process |
| GB2206579B (en) * | 1987-07-10 | 1991-05-29 | Erba Farmitalia | 6a and 6b-(substituted methyl)-penicillanic acid derivatives |
| CN102977120B (en) * | 2012-12-14 | 2015-05-27 | 江西富祥药业股份有限公司 | Method for preparing and crystallizing sulbactam pivoxyl |
-
1980
- 1980-09-22 IE IE1963/80A patent/IE50650B1/en unknown
- 1980-09-23 GB GB8030709A patent/GB2059960B/en not_active Expired
- 1980-10-07 DE DE19803037896 patent/DE3037896A1/en not_active Withdrawn
- 1980-10-08 DK DK424080A patent/DK154085C/en active
- 1980-10-09 CA CA000362093A patent/CA1142174A/en not_active Expired
- 1980-10-09 IT IT25223/80A patent/IT1132938B/en active
- 1980-10-10 CH CH760280A patent/CH646174A5/en not_active IP Right Cessation
- 1980-10-10 FR FR8021730A patent/FR2467210A1/en active Granted
- 1980-10-10 SE SE8007141A patent/SE449613B/en not_active IP Right Cessation
- 1980-10-10 LU LU82842A patent/LU82842A1/en unknown
- 1980-10-10 NL NL8005626A patent/NL8005626A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1132938B (en) | 1986-07-09 |
| SE449613B (en) | 1987-05-11 |
| DE3037896A1 (en) | 1981-04-23 |
| GB2059960A (en) | 1981-04-29 |
| DK154085C (en) | 1989-02-27 |
| CH646174A5 (en) | 1984-11-15 |
| FR2467210B1 (en) | 1983-08-19 |
| IT8025223A0 (en) | 1980-10-09 |
| IE50650B1 (en) | 1986-06-11 |
| NL8005626A (en) | 1981-04-14 |
| GB2059960B (en) | 1983-10-19 |
| LU82842A1 (en) | 1981-06-04 |
| CA1142174A (en) | 1983-03-01 |
| DK424080A (en) | 1981-04-12 |
| SE8007141L (en) | 1981-04-12 |
| DK154085B (en) | 1988-10-10 |
| FR2467210A1 (en) | 1981-04-17 |
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