IE36365B1 - Penicillins - Google Patents

Penicillins

Info

Publication number
IE36365B1
IE36365B1 IE669/72A IE66972A IE36365B1 IE 36365 B1 IE36365 B1 IE 36365B1 IE 669/72 A IE669/72 A IE 669/72A IE 66972 A IE66972 A IE 66972A IE 36365 B1 IE36365 B1 IE 36365B1
Authority
IE
Ireland
Prior art keywords
acid
isocyanate
acetyl
furoyl
nitrobenzoyl
Prior art date
Application number
IE669/72A
Other versions
IE36365L (en
Original Assignee
Beecham Group 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
Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd
Publication of IE36365L publication Critical patent/IE36365L/en
Publication of IE36365B1 publication Critical patent/IE36365B1/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
    • C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
    • C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
    • C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
    • C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1324752 N-Acylallophanamidobenzyl penicillins BEECHAM GROUP Ltd 23 May 1972 [4 June 1971] 18990/71 Headings C2A and C2C Novel penicillins having the Formula (I) and salts and esters thereof, wherein R is phenyl or substituted phenyl and R<SP>1</SP> is an acyl group are prepared by either (i) reacting 6- aminopenicillanic acid or a salt or ester thereof with an acylating reactive derivative of an acid of Formula (II) or (ii) reacting an α-amino-benzyl or substituted benzyl-penicillin or a salt or ester thereof with an N - methyl - N - nitroso - N<SP>1</SP> - acylbiuret; and optionally converting the product in each case into a salt or ester. The salts may be of sodium, potassium, calcium, aluminium, ammonium or substituted ammonium. Esters may be acetoxymethyl or pivaloyloxymethyl esters. Suitable substituents of R are halogen, alkyl, alkoxy or hydroxy groups. In the examples, the group R<SP>1</SP> is acetyl, benzoyl, p-nitrobenzoyl and furoyl. N<SP>1</SP>-Acetyl-N-methyl biuret is prepared by acylating N-methylbiuret with acetic anhydride. It is treated with nitrous acid (NaNO 2 and formic acid) to give N<SP>1</SP>-acetyl-N-methyl-N-nitrosobiuret. D ( - )-α-Ureidophenylacetic acid is prepared by reacting D ( - )-α-aminophenylacetic acid with potassium isocyanate and hydrolysing the product. It is subsequently reacted with (i) benzoyl isocyanate, (ii) p-nitrobenzoyl isocyanate, and (iii) Z-furoyl isocyanate, followed in each case by hydrolysis, to give acids of Formula (II) above wherein R<SP>1</SP> is respectively: benzoyl, p-nitrobenzoyl and 2-furoyl. [GB1324752A]
IE669/72A 1971-06-04 1972-05-19 Penicillins IE36365B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1899071 1971-06-04

Publications (2)

Publication Number Publication Date
IE36365L IE36365L (en) 1972-12-04
IE36365B1 true IE36365B1 (en) 1976-10-13

Family

ID=10121898

Family Applications (1)

Application Number Title Priority Date Filing Date
IE669/72A IE36365B1 (en) 1971-06-04 1972-05-19 Penicillins

Country Status (9)

Country Link
AT (2) AT315371B (en)
BE (1) BE784374A (en)
DE (1) DE2226822A1 (en)
ES (1) ES403453A1 (en)
GB (1) GB1324752A (en)
IE (1) IE36365B1 (en)
IL (1) IL39497A0 (en)
NL (1) NL7207381A (en)
ZA (1) ZA723522B (en)

Also Published As

Publication number Publication date
AT315371B (en) 1974-05-27
BE784374A (en) 1972-12-04
GB1324752A (en) 1973-07-25
AT317431B (en) 1974-08-26
IL39497A0 (en) 1972-07-26
IE36365L (en) 1972-12-04
NL7207381A (en) 1972-12-06
ZA723522B (en) 1973-03-28
ES403453A1 (en) 1975-05-01
DE2226822A1 (en) 1973-12-13

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