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GB873049A - Improvements in or relating to penicillin derivatives - Google Patents

Improvements in or relating to penicillin derivatives

Info

Publication number
GB873049A
GB873049A GB31847/58A GB3184758A GB873049A GB 873049 A GB873049 A GB 873049A GB 31847/58 A GB31847/58 A GB 31847/58A GB 3184758 A GB3184758 A GB 3184758A GB 873049 A GB873049 A GB 873049A
Authority
GB
United Kingdom
Prior art keywords
amino
substituted
penicillin
group
acid
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
GB31847/58A
Inventor
Frank Peter Doyle
John Herbert Charles Nayler
Harry Smith
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 Research Laboratories Ltd
Original Assignee
Beecham Research Laboratories 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26251956&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=GB873049(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to GB31847/58A priority Critical patent/GB873049A/en
Application filed by Beecham Research Laboratories Ltd filed Critical Beecham Research Laboratories Ltd
Priority to ES0252422A priority patent/ES252422A1/en
Priority to NO133325A priority patent/NO115737B/no
Priority to FR806723A priority patent/FR246M/fr
Priority to DK356359AA priority patent/DK126118B/en
Priority to CH7907859A priority patent/CH387635A/en
Priority to CH638961A priority patent/CH407126A/en
Priority to FR863883A priority patent/FR12F/en
Publication of GB873049A publication Critical patent/GB873049A/en
Priority to CY24262A priority patent/CY242A/en
Priority to GB4154162A priority patent/GB978178A/en
Priority to MY6200044A priority patent/MY6200044A/en
Priority to OA50915A priority patent/OA00880A/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
    • C07D499/68—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 with aromatic rings as additional substituents on the carbon chain
    • 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
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to penicillins of the general formula <FORM:0873049/IV (b)/1> where X is an amino-substituted acyl group containing up to 20 carbon atoms and having the formula <FORM:0873049/IV (b)/2> where R is hydrogen or an amino, carboxyl or substituted or unsubstituted alkyl, aryl, aralkyl or heterocyclic group, and n is zero or an integer, and non-toxic salts thereof. X may be <FORM:0873049/IV (b)/3> where n is zero or 1 to 6, and R is hydrogen or an alkyl, aryl, aralkyl or heterocyclic group which may be substituted; R being phenyl, chlorophenyl, methoxyphenyl, furyl or cyclohexyl when n is zero <FORM:0873049/IV (b)/4> <FORM:0873049/IV (b)/5> where n is 1 to 4. Typical penicillins are a -aminobenzyl penicillin, a -amino-p-methoxybenzyl penicillin, a -amino-2-furylpenicillin, a -aminoheptylpenicillin, a -aminopentyl penicillin, a -aminocyclohexyl penicillin and a -amino-p-chlorobenzyl penicillin. The non-toxic salts are, e.g. the sodium, potassium, calcium, aluminium, ammonium and substituted ammonium salts, e.g. salts of trialkylamines, procaine, dibenzylamine, N-benzyl-beta-phenylethylamine, 1-ephenamine, N,N1-dibenzylethylene diamine, dehydroabietylamine and N,N1-bis-dehydroabietylethylene diamine. The penicillins are produced by reacting 6-aminopenicillinic acid with an acid of general formula XOH (where X is as defined above) having its amino group or groups protected, or a salt thereof, and thereafter removing the protecting group or groups under sufficiently mild conditions to avoid destruction of the penicillin nucleus. The acid may be in the form of a mixed anhydride prepared by reacting the amino-substituted carboxylic acid, or a salt thereof, having its amino groups protected, with an ester of chlorocarbonic acid. The protecting group may be a trityl group or a group of general formula R11O.CO- where R11 is an alkyl, benzyl, substituted benzyl, phenyl or substituted phenyl group. The protecting groups may be removed by catalytic hydrogenation using palladium on a barium carbonate support. Specifications 870,395 and 870,396 are referred to.
GB31847/58A 1958-10-06 1958-10-06 Improvements in or relating to penicillin derivatives Expired GB873049A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
GB31847/58A GB873049A (en) 1958-10-06 1958-10-06 Improvements in or relating to penicillin derivatives
ES0252422A ES252422A1 (en) 1958-10-06 1959-10-02 Improvements in or relating to penicillin derivatives
NO133325A NO115737B (en) 1958-10-06 1959-10-05
FR806723A FR246M (en) 1958-10-06 1959-10-05
DK356359AA DK126118B (en) 1958-10-06 1959-10-06 Process for the preparation of 6-aminopenicillanic acid derivatives or salts thereof.
CH7907859A CH387635A (en) 1958-10-06 1959-10-06 Process for the production of penicillins
CH638961A CH407126A (en) 1958-10-06 1961-06-01 Process for the preparation of epimeric α-amino-benzylpenicillins
FR863883A FR12F (en) 1958-10-06 1961-06-05 Penicillin derivatives and their preparation process.
CY24262A CY242A (en) 1958-10-06 1962-07-03 Improvements in or relating to penicillin derivatives
GB4154162A GB978178A (en) 1958-10-06 1962-11-02 Penicillins
MY6200044A MY6200044A (en) 1958-10-06 1962-12-31 Improvements in or relating to penicillin derivatives
OA50915A OA00880A (en) 1958-10-06 1964-12-18 Derivatives of penicellin and their preparation process.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB31847/58A GB873049A (en) 1958-10-06 1958-10-06 Improvements in or relating to penicillin derivatives
GB1630359 1959-05-12

Publications (1)

Publication Number Publication Date
GB873049A true GB873049A (en) 1961-07-19

Family

ID=26251956

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31847/58A Expired GB873049A (en) 1958-10-06 1958-10-06 Improvements in or relating to penicillin derivatives

Country Status (8)

Country Link
CH (1) CH387635A (en)
CY (1) CY242A (en)
DK (1) DK126118B (en)
ES (1) ES252422A1 (en)
FR (1) FR246M (en)
GB (1) GB873049A (en)
NO (1) NO115737B (en)
OA (1) OA00880A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK104060C (en) * 1962-08-18 1966-03-28 Beecham Res Lab Process for the preparation of α-aminobenzylpenicillin or salts thereof.
US3245984A (en) * 1961-09-26 1966-04-12 Lepetit Spa Amino-alpha-phenylalkyl penicillins
DE1296142B (en) * 1962-01-29 1969-05-29 Bristol Myers Co Process for the preparation of ª ‡ -aminobenzylpenicillin
EP0477639A1 (en) * 1990-09-22 1992-04-01 Bayer Ag Substituted amino acid amide derivatives, their preparation and use
US5158962A (en) * 1989-11-01 1992-10-27 Bayer Aktiengesellschaft Fungicidal substituted amino acid amides
US5723646A (en) * 1991-01-24 1998-03-03 Bayer Aktiengesellschaft Substituted amino acid amide derivatives their preparation and use as fungicides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3245984A (en) * 1961-09-26 1966-04-12 Lepetit Spa Amino-alpha-phenylalkyl penicillins
DE1296142B (en) * 1962-01-29 1969-05-29 Bristol Myers Co Process for the preparation of ª ‡ -aminobenzylpenicillin
DK104060C (en) * 1962-08-18 1966-03-28 Beecham Res Lab Process for the preparation of α-aminobenzylpenicillin or salts thereof.
US5158962A (en) * 1989-11-01 1992-10-27 Bayer Aktiengesellschaft Fungicidal substituted amino acid amides
EP0477639A1 (en) * 1990-09-22 1992-04-01 Bayer Ag Substituted amino acid amide derivatives, their preparation and use
US5723646A (en) * 1991-01-24 1998-03-03 Bayer Aktiengesellschaft Substituted amino acid amide derivatives their preparation and use as fungicides
US5942541A (en) * 1991-01-24 1999-08-24 Bayer Aktiengesellschaft Substituted amino acid amide derivatives their preparation and use as fungicides

Also Published As

Publication number Publication date
DK126118B (en) 1973-06-12
ES252422A1 (en) 1960-01-01
CH387635A (en) 1965-02-15
NO115737B (en) 1968-11-25
FR246M (en) 1900-01-01
CY242A (en) 1962-07-03
OA00880A (en) 1968-03-22

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