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US4423230A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of an intermediate for N-(methylsulfonyl)-1,2,8,8a-cyclopropa[c][1,2-b:-4,3-b']dipyrol-4(5H)-one

Assignee: Pharmacia and Upjohn Co
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Filing: 1982-02-08
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Granted: 1983-12-27
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Expires: 2002-02-08
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Abstract

Abstract Novel antibacterially-active compound, 1,2,8,8a-cyclopropa[c]benzo[1,2-b:-4,3-b']dipyrol-4(5H)-one, prepared by a novel chemical process. This compound, as well as antibacterially-active intermediates, can be used to eradicate or control susceptible bacteria, for example, B. subtilis, K. pneumonia, S. lutea, S. aureus, and M. avium. Included is a process for the preparation of an intermediate compound of the formula ##STR1## wherein R 2 , R 3 and R 4 are as defined hereinafter.

Inventors

  • 👤 Wendell Wierenga

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 20:29
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/06; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/12

Claims Analysis

Total Claims: 2
Claim 1
Independent Claim 160 words
A process for preparing a compound of the formula wherein R 2 and R 3 are H, alkyl of from 1 to 5 carbon atoms, inclusive, and phenyl; R 4 is selected from the group consisting of SO 2 R 2 , SO 2 CH 2 CO phenyl, CO 2 CH 2 Z where Z is selected from the group consisting of CH 2 I, CCl 3 , CH 2 SO 2 R 2 , Ph(phenyl), and fluorenylmethyl, and X is selected from the group consisting of OSO 2 R 2 , Cl, Br, and I, which comprises reacting a compound of the formula ##STR4## wherein R 2 , R 3 , and R 4 are as defined above, with a reagent selected from the group consisting of sulfonyl chloride, carbon tetrachloride/triphenylphosphine, carbon tetrabromide/triphenylphosphine, and N-iodosuccinimide triphenylphosphine, separating the organic phase from the reaction mixture, drying and concentrating said organic phase, and recovering the desired product by silica gel chromatography.
Claim 2
Dependent Claim 160 words
A process for preparing a compound of the formula wherein R 2 and R 3 are H, alkyl of from 1 to 5 carbon atoms, inclusive, and phenyl; R 4 is selected from the group consisting of SO 2 R 2 , SO 2 CH 2 CO phenyl, CO 2 CH 2 Z where Z is selected from the group consisting of CH 2 I, CCl 3 , CH 2 SO 2 R 2 , Ph(phenyl), and fluorenylmethyl, and X is selected from the group consisting of OSO 2 R 2 , Cl, Br, and I, which comprises reacting a compound of the formula ##STR4## wherein R 2 , R 3 , and R 4 are as defined above, with a reagent selected from the group consisting of sulfonyl chloride, carbon tetrachloride/triphenylphosphine, carbon tetrabromide/triphenylphosphine, and N-iodosuccinimide triphenylphosphine, separating the organic phase from the reaction mixture, drying and concentrating said organic phase, and recovering the desired product by silica gel chromatography.

References Cited (Backward Citations)

US4169888A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-12-26 1987-06-27 1987-12-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-12-26 1991-06-27 1991-12-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-12-26 1995-06-27 1995-12-27 $7700.00 Window Closed / Lapsed

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