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US4375434A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for 6'-amino-penicillanoyloxymethyl penicillanate 1,1-dioxide

Assignee: Pfizer Inc
•
Filing: 1982-06-21
•
Granted: 1983-03-01
•
Expires: 2002-06-21
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Abstract

Abstract 6'-Aminopenicillanoyloxymethyl penicillanate 1,1-dioxide is prepared by a two-step procedure. The first step consists of coupling a salt of a 6-(protected amino)penicillanic acid with a halomethyl, an alkylsulfonyloxymethyl or an arylsulfonyloxymethyl ester of penicillanic acid 1,1-dioxide, to give a 6'-(protected amino)penicillanoyloxymethyl penicillanate 1,1-dioxide, wherein the protection at the 6-position has been achieved by coupling the 6-aminopenicillanic acid with a beta-dicarbonyl compound. The second step consists of removal of the protecting group on the 6'-amino group, using aqueous acid. 6'-Aminopenicillanoyloxymethyl penicillanate 1,1-dioxide is a chemical intermediate for preparing antibacterial agents. Also claimed are the 6'-(protected amino)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds used as intermediates in the process of this invention.

Inventors

  • 👤 David L. Hageman

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 16:19
CPC Classifications
C; C07; C07D; C07D499/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 166 words
A process for preparing the compound of the formula ##STR10## or an acid addition salt thereof, which comprises: (i) contacting a compound of the formula ##STR11## with from 0.5 to 1.5 molar equivalents of a compound of the formula ##STR12## in a reaction-inert organic solvent, at a temperature in the range from 0°-60° C., to give a compound of the formula ##STR13## and (ii) exposing the product of step (i) to aqueous or partially aqueous reaction conditions, at a pH in the range from 0.5 to 3.0, at a temperature in the range from 0° to 30° C., until conversion to an acid-addition salt of the compound of formula IV is substantially complete; wherein R 2 is selected from the group consisting of alkyl having 1 to 3 carbons, alkoxy having 1 to 3 carbons and phenyl, M is a carboxylate salt forming cation and X is selected from the group consisting of chloro, bromo, iodo, alkylsulfonyloxy having from 1 to 4 carbons, benzenesulfonyloxy and toluenesulfonyloxy.
Claim 2
Dependent Claim 166 words
A process for preparing the compound of the formula ##STR10## or an acid addition salt thereof, which comprises: (i) contacting a compound of the formula ##STR11## with from 0.5 to 1.5 molar equivalents of a compound of the formula ##STR12## in a reaction-inert organic solvent, at a temperature in the range from 0°-60° C., to give a compound of the formula ##STR13## and (ii) exposing the product of step (i) to aqueous or partially aqueous reaction conditions, at a pH in the range from 0.5 to 3.0, at a temperature in the range from 0° to 30° C., until conversion to an acid-addition salt of the compound of formula IV is substantially complete; wherein R 2 is selected from the group consisting of alkyl having 1 to 3 carbons, alkoxy having 1 to 3 carbons and phenyl, M is a carboxylate salt forming cation and X is selected from the group consisting of chloro, bromo, iodo, alkylsulfonyloxy having from 1 to 4 carbons, benzenesulfonyloxy and toluenesulfonyloxy.
Claim 3
Dependent Claim 12 words
The process according to claim 1, wherein R 2 is said alkoxy.
Claim 4
Dependent Claim 11 words
The process according to claim 2, wherein R 2 is methoxy.
Claim 5
Dependent Claim 16 words
The process according to claim 2 or claim 3, wherein X is chloro, bromo or iodo.
Claim 6
Dependent Claim 10 words
The process according to claim 4, wherein X is iodo.
Claim 7
Dependent Claim 12 words
The process according to claim 5, wherein M is a tetra-n-butylammonium cation.

References Cited (Backward Citations)

GB2044255A Cited
US4244951A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-02-28 1986-08-30 1987-03-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-02-28 1990-08-30 1991-03-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-02-28 1994-08-30 1995-03-01 $7700.00 Window Closed / Lapsed

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