ES312185A1 - Penicillins - Google Patents

Penicillins

Info

Publication number
ES312185A1
ES312185A1 ES0312185A ES312185A ES312185A1 ES 312185 A1 ES312185 A1 ES 312185A1 ES 0312185 A ES0312185 A ES 0312185A ES 312185 A ES312185 A ES 312185A ES 312185 A1 ES312185 A1 ES 312185A1
Authority
ES
Spain
Prior art keywords
amino
acid
aralkyl
aryl
alkyl
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
ES0312185A
Other languages
Spanish (es)
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 ES312185A1 publication Critical patent/ES312185A1/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

Landscapes

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

Abstract

The invention comprises penicillins of the general formula:-<FORM:1033257/C2/1> and non-toxic salts thereof, e.g. 6-[D(-)a -amino-a - (m - aminophenyl)acetamido] penicillanic acid. The penicillins are produced by reacting 6-aminopenicillanic acid with a di-substituted phenylacetic acid of general formula <FORM:1033257/C2/2> or a non-toxic salt thereof, where A and B are the same or different and each is a group capable of conversion into the amino group, and subsequently treating the intermediate penicillin so formed in order to convert A and B into amino groups. Catalytic hydrogenation and/or mild acid hydrolysis is used. A and B may be benzyloxycarbonylamino, which may be substituted, azido (B only), nitro (A only), or enamine groups or o-hydroxyarylideneamino groups of formulae <FORM:1033257/C2/3> and <FORM:1033257/C2/4> respectively, wherein R1 is alkyl, aralkyl, aryl R2 is alkyl, aralkyl, aryl, alkoxy, aralkoxy, aryloxy R3 is H, alkyl, aralkyl or aryl or R3 with either R1 or R2 is carbocyclic Z is residue of a substituted or unsubstituted benzene or naphthalene ring. D(-)a -amino-m-aminophenylacetic acid is produced by the catalytic hydrogenation of D(-)a -amino-m-nitrophenylacetic acid, which is obtained by the nitration of D(-)a -amino-phenylacetic acid. DL - a - benzyloxycarbonylamino - a - (m-benzyl oxycarbonylaminophenyl) acetic acid is produced by treating DL-a -amino-a -(m-amino-phenyl) acetic acid with benzyl chlorocarbonate in aqueous alkali. The corresponding p-amino-phenyl derivative is likewise prepared.
ES0312185A 1964-04-23 1965-04-23 Penicillins Expired ES312185A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB16799/64A GB1033257A (en) 1964-04-23 1964-04-23 Penicillins

Publications (1)

Publication Number Publication Date
ES312185A1 true ES312185A1 (en) 1965-08-16

Family

ID=10083873

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0312185A Expired ES312185A1 (en) 1964-04-23 1965-04-23 Penicillins

Country Status (9)

Country Link
AT (1) AT264711B (en)
BE (1) BE662478A (en)
BR (1) BR6568922D0 (en)
CH (1) CH442311A (en)
DE (1) DE1545586A1 (en)
ES (1) ES312185A1 (en)
FR (1) FR4394M (en)
GB (1) GB1033257A (en)
NL (1) NL6505163A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1190897B (en) * 1982-06-29 1988-02-24 Opos Biochimica Srl PROCEDURE FOR THE PREPARATION OF THE 1-ETHOXYCARBONYLOXYETHYL ACID ACID 6- (D (-) - ALPHA AMINOALPHA-PHENYLACETAMIDE) -PENICILLANIC

Also Published As

Publication number Publication date
CH442311A (en) 1967-08-31
AT264711B (en) 1968-09-10
BR6568922D0 (en) 1973-08-07
BE662478A (en) 1965-10-14
NL6505163A (en) 1965-10-25
FR4394M (en) 1966-09-05
DE1545586A1 (en) 1969-07-31
GB1033257A (en) 1966-06-22

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