GB1072108A - Penicillanic acid, its salts and esters - Google Patents

Penicillanic acid, its salts and esters

Info

Publication number
GB1072108A
GB1072108A GB2194364A GB2194364A GB1072108A GB 1072108 A GB1072108 A GB 1072108A GB 2194364 A GB2194364 A GB 2194364A GB 2194364 A GB2194364 A GB 2194364A GB 1072108 A GB1072108 A GB 1072108A
Authority
GB
United Kingdom
Prior art keywords
treatment
salts
esters
penicillanic acid
derivatives
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
GB2194364A
Inventor
Michel Claesen
Hubert Vanderhaeghe
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.)
RIT RECH IND THERAPEUT
Original Assignee
RIT RECH IND THERAPEUT
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 RIT RECH IND THERAPEUT filed Critical RIT RECH IND THERAPEUT
Publication of GB1072108A publication Critical patent/GB1072108A/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

Abstract

The invention relates to penicillanic acid having the formula <FORM:1072108/C2/1> its salts and esters. These compounds are prepared by hydrogenation, particularly catalytic hydrogenation, of a 6-halopenicillanic acid, or a salt or ester thereof of formula <FORM:1072108/C2/2> where Hal is chloro, bromo or iodo and M is H, a cation, alkyl or aryl. Penicillanic acid, its salts and esters are converted to (a) penicillins by treatment with an acyl halide or acyl anhydride, (b) 6-azo derivatives by treatment with diazonium salts, (c) 6-alkyl and 6-aryl derivatives by treatment with a reactive halide, (d) 6-alkylidene and 6-arylidene derivatives by treatment with ketones and aldehydes and (e) Mannich bases by treatment with aldehydes and ketones in the presence of primary or secondary amines.
GB2194364A 1963-05-29 1964-05-27 Penicillanic acid, its salts and esters Expired GB1072108A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US28395463A 1963-05-29 1963-05-29

Publications (1)

Publication Number Publication Date
GB1072108A true GB1072108A (en) 1967-06-14

Family

ID=23088289

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2194364A Expired GB1072108A (en) 1963-05-29 1964-05-27 Penicillanic acid, its salts and esters

Country Status (2)

Country Link
BE (1) BE648188A (en)
GB (1) GB1072108A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2405950A1 (en) * 1977-05-09 1979-05-11 Ciba Geigy Ag NEW 1 PENICILLANIC ACID OXIDES USEFUL IN THE SYNTHESIS OF DRUGS
US4234579A (en) * 1977-06-07 1980-11-18 Pfizer Inc. Penicillanic acid 1,1-dioxides as β-lactamase inhibitors
US4241050A (en) * 1978-09-01 1980-12-23 Pfizer Inc. Penam 1,1-dioxides as beta-lactamase inhibitors
US4276285A (en) * 1977-06-07 1981-06-30 Pfizer Inc. Combinations of penicillanic acid 1,1-dioxide with 7-(D-2-[4-ethylpiperazin-2,3-dione-1-carboxamido]-2-[4-hydroxyphenyl]acetamido)-3-([1-methyl-5-tetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid
US4340539A (en) 1980-01-21 1982-07-20 Bristol-Myers Company Derivatives of 6-bromo penicillanic acid
US4420426A (en) 1979-03-05 1983-12-13 Pfizer Inc. 6-Alpha-halopenicillanic acid 1,1-dioxides
US4714761A (en) * 1979-03-05 1987-12-22 Pfizer Inc. 6,6-dihalopenicillanic acid 1,1-dioxides and process

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2405950A1 (en) * 1977-05-09 1979-05-11 Ciba Geigy Ag NEW 1 PENICILLANIC ACID OXIDES USEFUL IN THE SYNTHESIS OF DRUGS
US4331676A (en) 1977-05-09 1982-05-25 Ciba-Geigy Corporation Thia-aza compounds with a β-lactam ring
US4234579A (en) * 1977-06-07 1980-11-18 Pfizer Inc. Penicillanic acid 1,1-dioxides as β-lactamase inhibitors
US4276285A (en) * 1977-06-07 1981-06-30 Pfizer Inc. Combinations of penicillanic acid 1,1-dioxide with 7-(D-2-[4-ethylpiperazin-2,3-dione-1-carboxamido]-2-[4-hydroxyphenyl]acetamido)-3-([1-methyl-5-tetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid
US4241050A (en) * 1978-09-01 1980-12-23 Pfizer Inc. Penam 1,1-dioxides as beta-lactamase inhibitors
US4420426A (en) 1979-03-05 1983-12-13 Pfizer Inc. 6-Alpha-halopenicillanic acid 1,1-dioxides
US4714761A (en) * 1979-03-05 1987-12-22 Pfizer Inc. 6,6-dihalopenicillanic acid 1,1-dioxides and process
US4340539A (en) 1980-01-21 1982-07-20 Bristol-Myers Company Derivatives of 6-bromo penicillanic acid

Also Published As

Publication number Publication date
BE648188A (en) 1964-09-16

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