FR2240227A1 - Penam- and cepham derivs prepn - by reaction of substd isopropenyl azetidin derivs and nucleophilic cpds: antibacterial - Google Patents

Penam- and cepham derivs prepn - by reaction of substd isopropenyl azetidin derivs and nucleophilic cpds: antibacterial

Info

Publication number
FR2240227A1
FR2240227A1 FR7423880A FR7423880A FR2240227A1 FR 2240227 A1 FR2240227 A1 FR 2240227A1 FR 7423880 A FR7423880 A FR 7423880A FR 7423880 A FR7423880 A FR 7423880A FR 2240227 A1 FR2240227 A1 FR 2240227A1
Authority
FR
France
Prior art keywords
derivs
cpds
reaction
substd
nucleophilic
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
FR7423880A
Other languages
French (fr)
Other versions
FR2240227B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujisawa Pharmaceutical Co Ltd
Original Assignee
Fujisawa Pharmaceutical Co Ltd
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
Priority claimed from JP11738472A external-priority patent/JPS5550955B2/ja
Priority claimed from JP12557272A external-priority patent/JPS5531789B2/ja
Priority claimed from JP12557372A external-priority patent/JPS5531791B2/ja
Priority claimed from JP12663772A external-priority patent/JPS5531794B2/ja
Priority claimed from JP47128658A external-priority patent/JPS5929597B2/en
Priority claimed from JP12890272A external-priority patent/JPS5641634B2/ja
Priority claimed from JP731201A external-priority patent/JPS5946950B2/en
Priority claimed from JP48087108A external-priority patent/JPS5946951B2/en
Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Publication of FR2240227A1 publication Critical patent/FR2240227A1/en
Publication of FR2240227B1 publication Critical patent/FR2240227B1/fr
Application granted granted Critical
Granted legal-status Critical Current

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
    • C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3

Abstract

Cpds. of gen formula (Ia) and (Ib): (where R1 = opt. substd. amino; R2 = opt. protected carboxy; R3 = lower alkyl; Y = a resdue of a nucleon hilic cpd.) are prepd. with a nucleophilic acid. (III), where R4 = residue of a thiol cpd. HR4. Reaction in inert solvent such as water, acetone, ethers, CHCl3, acetic acid etc. in the presence of an agent which removes HR4 such as a Lewis cid, CuO, Ag- or Hg-salts etc. Cpds. (III) are e.g. thicyanic acid, thiocyan, alphatic-aromatic- or cyclic thio-urea or -amines etc. (Ib) is formed by oxidation reaction of (Ia) using e.g. O3, inorganic- or organic per-acids, etc. pref. in the presence of tungstic-, molybdic-or vanadic acid or salts. (Ia) and (Ib) have antibacterial activity.
FR7423880A 1972-11-22 1974-07-09 Penam- and cepham derivs prepn - by reaction of substd isopropenyl azetidin derivs and nucleophilic cpds: antibacterial Granted FR2240227A1 (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP11738472A JPS5550955B2 (en) 1972-11-22 1972-11-22
JP12557272A JPS5531789B2 (en) 1972-12-13 1972-12-13
JP12557372A JPS5531791B2 (en) 1972-12-13 1972-12-13
JP12663772A JPS5531794B2 (en) 1972-12-15 1972-12-15
JP47128658A JPS5929597B2 (en) 1972-12-20 1972-12-20 Method for producing 2-substituted alkyl-2-alkylpenam-3-carboxylic acids
JP12890272A JPS5641634B2 (en) 1972-12-21 1972-12-21
JP731201A JPS5946950B2 (en) 1972-12-23 1972-12-23 Method for producing 3-substituted cepham-4-carboxylic acids
JP48087108A JPS5946951B2 (en) 1973-08-01 1973-08-01 Method for producing 3-substituted cefem-4-carboxylic acid-1-oxides

Publications (2)

Publication Number Publication Date
FR2240227A1 true FR2240227A1 (en) 1975-03-07
FR2240227B1 FR2240227B1 (en) 1977-11-25

Family

ID=27571429

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7423880A Granted FR2240227A1 (en) 1972-11-22 1974-07-09 Penam- and cepham derivs prepn - by reaction of substd isopropenyl azetidin derivs and nucleophilic cpds: antibacterial

Country Status (1)

Country Link
FR (1) FR2240227A1 (en)

Also Published As

Publication number Publication date
FR2240227B1 (en) 1977-11-25

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Legal Events

Date Code Title Description
ST Notification of lapse