IE37846L - 6 - alkoxypenicillanic and 7 - alkoxycephalosporin acids - Google Patents

6 - alkoxypenicillanic and 7 - alkoxycephalosporin acids

Info

Publication number
IE37846L
IE37846L IE731052A IE105273A IE37846L IE 37846 L IE37846 L IE 37846L IE 731052 A IE731052 A IE 731052A IE 105273 A IE105273 A IE 105273A IE 37846 L IE37846 L IE 37846L
Authority
IE
Ireland
Prior art keywords
lactam
acylamido
ester
benzyl
formula
Prior art date
Application number
IE731052A
Other versions
IE37846B1 (en
Original Assignee
Lilly Co Eli
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lilly Co Eli filed Critical Lilly Co Eli
Publication of IE37846L publication Critical patent/IE37846L/en
Publication of IE37846B1 publication Critical patent/IE37846B1/en

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

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]
IE1052/73A 1972-07-03 1973-06-25 Process for preparing 6-alkoxypenicillanic and 7-alkoxycephalosporin acids IE37846B1 (en)

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 true IE37846L (en) 1974-01-03
IE37846B1 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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
BE801766A (en) 1974-01-02
FR2236857B1 (en) 1978-05-26
DE2333845A1 (en) 1974-01-24
CH590289A5 (en) 1977-07-29
JPS5775987A (en) 1982-05-12
IE37846B1 (en) 1977-10-26
FR2236857A1 (en) 1975-02-07
IL42603A0 (en) 1973-08-29
NL181008C (en) 1987-06-01
NL7309292A (en) 1974-01-07
JPS5749556B2 (en) 1982-10-22
GB1439371A (en) 1976-06-16
JPS618065B2 (en) 1986-03-11
NL181008B (en) 1987-01-02
JPS4942689A (en) 1974-04-22

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