GB1033257A - Penicillins - Google Patents

Penicillins

Info

Publication number
GB1033257A
GB1033257A GB16799/64A GB1679964A GB1033257A GB 1033257 A GB1033257 A GB 1033257A GB 16799/64 A GB16799/64 A GB 16799/64A GB 1679964 A GB1679964 A GB 1679964A GB 1033257 A GB1033257 A GB 1033257A
Authority
GB
United Kingdom
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
GB16799/64A
Inventor
Brian William Hatt
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 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
Priority to GB16799/64A priority Critical patent/GB1033257A/en
Priority to BR16892265A priority patent/BR6568922D0/en
Priority to BE662478D priority patent/BE662478A/xx
Priority to FR13595A priority patent/FR4394M/fr
Priority to CH553365A priority patent/CH442311A/en
Priority to DE19651545586 priority patent/DE1545586A1/en
Priority to AT365565A priority patent/AT264711B/en
Priority to NL6505163A priority patent/NL6505163A/xx
Priority to ES0312185A priority patent/ES312185A1/en
Publication of GB1033257A publication Critical patent/GB1033257A/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.
GB16799/64A 1964-04-23 1964-04-23 Penicillins Expired GB1033257A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB16799/64A GB1033257A (en) 1964-04-23 1964-04-23 Penicillins
BR16892265A BR6568922D0 (en) 1964-04-23 1965-04-13 A PROCESS OF OBTAINING NEW PENICILLINES
BE662478D BE662478A (en) 1964-04-23 1965-04-14
FR13595A FR4394M (en) 1964-04-23 1965-04-16
CH553365A CH442311A (en) 1964-04-23 1965-04-21 Process for the production of new penicillins
DE19651545586 DE1545586A1 (en) 1964-04-23 1965-04-21 Diaminobenzylpenicillins and processes for their preparation
AT365565A AT264711B (en) 1964-04-23 1965-04-21 Process for the production of new penicillins
NL6505163A NL6505163A (en) 1964-04-23 1965-04-22
ES0312185A ES312185A1 (en) 1964-04-23 1965-04-23 Penicillins

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
GB1033257A true GB1033257A (en) 1966-06-22

Family

ID=10083873

Family Applications (1)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4619785A (en) * 1982-06-29 1986-10-28 Astra Lakemedel Aktiebolag Novel synthesis route for bacampicillin

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4619785A (en) * 1982-06-29 1986-10-28 Astra Lakemedel Aktiebolag Novel synthesis route for bacampicillin

Also Published As

Publication number Publication date
BE662478A (en) 1965-10-14
ES312185A1 (en) 1965-08-16
CH442311A (en) 1967-08-31
DE1545586A1 (en) 1969-07-31
BR6568922D0 (en) 1973-08-07
FR4394M (en) 1966-09-05
AT264711B (en) 1968-09-10
NL6505163A (en) 1965-10-25

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