GB1324752A - Penicillins - Google Patents

Penicillins

Info

Publication number
GB1324752A
GB1324752A GB1899071A GB1324752DA GB1324752A GB 1324752 A GB1324752 A GB 1324752A GB 1899071 A GB1899071 A GB 1899071A GB 1324752D A GB1324752D A GB 1324752DA GB 1324752 A GB1324752 A GB 1324752A
Authority
GB
United Kingdom
Prior art keywords
acid
isocyanate
acetyl
furoyl
nitrobenzoyl
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.)
Expired
Application number
GB1899071A
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 PLC filed Critical Beecham Group PLC
Publication of GB1324752A publication Critical patent/GB1324752A/en
Expired 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
    • 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.
GB1899071A 1971-06-04 1972-05-23 Penicillins Expired GB1324752A (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
GB1324752A true GB1324752A (en) 1973-07-25

Family

ID=10121898

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1899071A Expired GB1324752A (en) 1971-06-04 1972-05-23 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
DE2226822A1 (en) 1973-12-13
ES403453A1 (en) 1975-05-01
NL7207381A (en) 1972-12-06
BE784374A (en) 1972-12-04
IL39497A0 (en) 1972-07-26
ZA723522B (en) 1973-03-28
IE36365B1 (en) 1976-10-13
AT315371B (en) 1974-05-27
IE36365L (en) 1972-12-04
AT317431B (en) 1974-08-26

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees