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US4105668A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam

Assignee: Pfizer Inc
•
Filing: 1977-04-22
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Granted: 1978-08-08
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Expires: 1997-04-22
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Abstract

Abstract Certain 6-amino-2,2-dimethyl-3-(1-substituted tetrazol-5-yl)penam and 6-(protected amino)-2,2-dimethyl-3-(1-substituted tetrazolyl-5-yl)penam compounds react with hydrogen fluoride to produce 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, a useful intermediate for the synthesis of antibacterial agents.

Inventors

  • 👤 Susumu Nakanishi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 17:34
CPC Classifications
C; C07; C07D; C07D499/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 243 words
A process for the preparation of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, or an acid-addition salt thereof, which comprises reacting a compound of formula ##STR16## or an acid-addition salt thereof, with hydrogen fluoride, at a temperature within the range from about -20° C. to about 20° C; wherein R 1 is selected from the group consisting of hydrogen and ##STR17## wherein R 3 , R 4 , and R 5 are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having from one to four carbon atoms, alkoxy having from one to four carbon atoms and phenyl; and R 2 is selected from the group consisting of ##STR18## wherein R 7 is at the 3-, 4- or 5-position and it is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, bromo, iodo, alkyl having from one to six carbon atoms, alkoxy having from one to six carbon atoms, benzyloxy and phenyl; R 8 is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, unbranched-alkyl having from one to six carbon atoms and unbranched-alkoxy having from one to six carbon atoms; R 10 is selected from the group consisting of hydrogen and methyl; and X is selected from the group consisting of oxygen and sulfur; provided that at least one of R 7 and R 8 is selected from the group consisting of 2-hydroxy, 4-hydroxy, 4-alkoxy having from one to six carbon atoms, 2-(unbranched-alkoxy) having from one to six carbon atoms and 4-benzyloxy .
Claim 2
Dependent Claim 243 words
A process for the preparation of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, or an acid-addition salt thereof, which comprises reacting a compound of formula ##STR16## or an acid-addition salt thereof, with hydrogen fluoride, at a temperature within the range from about -20° C. to about 20° C; wherein R 1 is selected from the group consisting of hydrogen and ##STR17## wherein R 3 , R 4 , and R 5 are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, alkyl having from one to four carbon atoms, alkoxy having from one to four carbon atoms and phenyl; and R 2 is selected from the group consisting of ##STR18## wherein R 7 is at the 3-, 4- or 5-position and it is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, bromo, iodo, alkyl having from one to six carbon atoms, alkoxy having from one to six carbon atoms, benzyloxy and phenyl; R 8 is selected from the group consisting of hydrogen, hydroxy, fluoro, chloro, unbranched-alkyl having from one to six carbon atoms and unbranched-alkoxy having from one to six carbon atoms; R 10 is selected from the group consisting of hydrogen and methyl; and X is selected from the group consisting of oxygen and sulfur; provided that at least one of R 7 and R 8 is selected from the group consisting of 2-hydroxy, 4-hydroxy, 4-alkoxy having from one to six carbon atoms, 2-(unbranched-alkoxy) having from one to six carbon atoms and 4-benzyloxy .
Claim 3
Dependent Claim 18 words
The process according to claim 1, wherein at least about twenty molar equivalents of hydrogen fluoride are used.
Claim 4
Dependent Claim 21 words
The process according to claim 2, wherein the said temperature is in the range from about -5° C. to 5° C.
Claim 5
Dependent Claim 11 words
The process according to claim 3, wherein R 1 is triphenylmethyl.
Claim 6
Dependent Claim 11 words
The process according to claim 3, wherein R 1 is hydrogen.
Claim 7
Dependent Claim 11 words
The process according to claim 5, wherein R 2 is furfuryl.
Claim 8
Dependent Claim 11 words
The process according to claim 5, wherein R 2 is ##STR19##
Claim 9
Dependent Claim 23 words
The process according to claim 7, wherein R 7 is hydrogen and R 8 is 4-alkoxy having from one to six carbon atoms.
Claim 10
Dependent Claim 11 words
The process according to claim 8, wherein R 8 is 4-methoxy.
Claim 11
Dependent Claim 23 words
The process according to claim 1 wherein the action is carried out in the presence of at least one molar equivalent of anisole.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-08-07 1982-02-06 1982-08-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-08-07 1986-02-06 1986-08-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-08-07 1990-02-06 1990-08-08 $7700.00 Window Closed / Lapsed

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