IE37846B1 - Process for preparing 6-alkoxypenicillanic and 7-alkoxycephalosporin acids - Google Patents
Process for preparing 6-alkoxypenicillanic and 7-alkoxycephalosporin acidsInfo
- Publication number
- IE37846B1 IE37846B1 IE1052/73A IE105273A IE37846B1 IE 37846 B1 IE37846 B1 IE 37846B1 IE 1052/73 A IE1052/73 A IE 1052/73A IE 105273 A IE105273 A IE 105273A IE 37846 B1 IE37846 B1 IE 37846B1
- Authority
- IE
- Ireland
- Prior art keywords
- lactam
- acylamido
- ester
- benzyl
- formula
- Prior art date
Links
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
-
- 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)
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1439371 Process for making 6-oxypenam and 7-oxycephem compounds ELI LILLY & CO 2 July 1973 [3 July 1972] 31538/73 Heading C2C Hydroxylated, alkoxylated, or aralkoxylated # -lactam compounds of the Formula I wherein R is an acyl group forming the acylamido substituent of the #-lactam compound; R 2 is hydrogen or a carboxylic-acid-protecting ester-forming group; R 3 is hydrogen, C 1-4 alkyl, benzyl, p-nitrobenzyl or 2,2,2-trichloroethyl; and Y is the 3-carbon fragment or the substituted 2-carbon fragment wherein Q is methyl or acetoxymethyl, are prepared by (a) reacting in an inert solvent a thio-substituted #-lactam ester compound of the formula wherein R 1 is C 1-4 alkyl or benzyl, R 2 is a carboxylic-acid-protecting ester-forming group and R and Y are as above-defined; with chlorine or bromine at a temperature from -80 to -25 C. to form the (3-lactam halosulphonium halide of the formula wherein R 2 is a carboxylic-acid-protecting ester-forming group and X is chloro or bromo; (b) reacting said (3-lactam halosulphonium halide in the presence of one equivalent of a base or a hydrogen halide acceptor with the alcohol R 3 0H wherein R 3 is C 1-4 alkyl, benzyl, p-nitrobenzyl, or 2,2,2-trichloroethyl, (c) when a compound of Formula I in which R 3 is hydrogen is desired, de-etherifying a resultant compound from step (b) in which R 3 is benzyl, pnitrobenzyl or 2,2,2-trichloroethyl; and (d) optionally de-esterifying the #-lactam ester thus obtained from steps (b) and (c). 6-Alkoxy- 6 - acylamido - penicillanic acids or 7 - alkoxy- 7 - acylamido - cephalosporanic acids are prepared by reacting an alkoxylated #-lactam ester with zinc in formic acid. 6-Hydroxy-6- acylamido - penicillanic acids and 7 - hydroxy- 7 - acylamido - cephalosporanic acids are prepared by using zinc in formic acid in step (c). Therapeutic compositions having antibacterial activity comprise above products (I) and are preferably administered parenterally. Reference has been directed by the Comptroller to Specifications 1,348,984 and 1,339,007.
[GB1439371A]
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26836272A | 1972-07-03 | 1972-07-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE37846L IE37846L (en) | 1974-01-03 |
IE37846B1 true IE37846B1 (en) | 1977-10-26 |
Family
ID=23022650
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE1052/73A IE37846B1 (en) | 1972-07-03 | 1973-06-25 | Process for preparing 6-alkoxypenicillanic and 7-alkoxycephalosporin acids |
Country Status (9)
Country | Link |
---|---|
JP (2) | JPS5749556B2 (en) |
BE (1) | BE801766A (en) |
CH (1) | CH590289A5 (en) |
DE (1) | DE2333845A1 (en) |
FR (1) | FR2236857B1 (en) |
GB (1) | GB1439371A (en) |
IE (1) | IE37846B1 (en) |
IL (1) | IL42603A0 (en) |
NL (1) | NL181008C (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5896161A (en) * | 1981-12-04 | 1983-06-08 | Tokyo Roki Kk | Fuel heater for engine |
US4656637A (en) * | 1985-02-14 | 1987-04-07 | Sundstrand Data Control, Inc. | Multiple ring laser gyro power supply |
-
1973
- 1973-06-25 IE IE1052/73A patent/IE37846B1/en unknown
- 1973-06-26 IL IL42603A patent/IL42603A0/en unknown
- 1973-06-29 BE BE1005206A patent/BE801766A/en unknown
- 1973-07-02 GB GB3153873A patent/GB1439371A/en not_active Expired
- 1973-07-02 FR FR7324163A patent/FR2236857B1/fr not_active Expired
- 1973-07-03 DE DE19732333845 patent/DE2333845A1/en active Pending
- 1973-07-03 JP JP48075182A patent/JPS5749556B2/ja not_active Expired
- 1973-07-03 CH CH970973A patent/CH590289A5/xx not_active IP Right Cessation
- 1973-07-03 NL NLAANVRAGE7309292,A patent/NL181008C/en not_active IP Right Cessation
-
1981
- 1981-07-08 JP JP56106842A patent/JPS5775987A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
FR2236857B1 (en) | 1978-05-26 |
BE801766A (en) | 1974-01-02 |
GB1439371A (en) | 1976-06-16 |
NL7309292A (en) | 1974-01-07 |
JPS4942689A (en) | 1974-04-22 |
NL181008B (en) | 1987-01-02 |
DE2333845A1 (en) | 1974-01-24 |
CH590289A5 (en) | 1977-07-29 |
JPS618065B2 (en) | 1986-03-11 |
JPS5749556B2 (en) | 1982-10-22 |
JPS5775987A (en) | 1982-05-12 |
IE37846L (en) | 1974-01-03 |
IL42603A0 (en) | 1973-08-29 |
FR2236857A1 (en) | 1975-02-07 |
NL181008C (en) | 1987-06-01 |
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