WO1993004070A1 - Derives d'acide acrylamido-penicillanique substitue - Google Patents

Derives d'acide acrylamido-penicillanique substitue Download PDF

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Publication number
WO1993004070A1
WO1993004070A1 PCT/GB1992/001484 GB9201484W WO9304070A1 WO 1993004070 A1 WO1993004070 A1 WO 1993004070A1 GB 9201484 W GB9201484 W GB 9201484W WO 9304070 A1 WO9304070 A1 WO 9304070A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
group
sodium
compound
exo
Prior art date
Application number
PCT/GB1992/001484
Other languages
English (en)
Inventor
Roger John Ponsford
Andrew Valentine Stachulski
Original Assignee
Smithkline Beecham, 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 Smithkline Beecham, Plc filed Critical Smithkline Beecham, Plc
Publication of WO1993004070A1 publication Critical patent/WO1993004070A1/fr

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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
    • 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

Definitions

  • Y is a group of formula:
  • a preferred am i no-protecting group R 1 in the intermediate of formula (llI) is acetyl, which R 1 group may suitably be removed from the product of formula (I) by treatment with aqueous sodium hydroxide.
  • the acid halide may be prepared by reacting the acid (lll) with a halogenating (eg chlorinating or brominating) agent such as phosphorus pentachloride, thionyl chloride or oxalyl chloride.
  • a halogenating agent such as phosphorus pentachloride, thionyl chloride or oxalyl chloride.
  • N represents a 5 or 6-membered heterocyclic ring, which may contain, in addition to the nitrogen atom, one or two further heteroatoms, selected from oxygen, nitrogen and sulphur and which may be substituted or fused to a benzene ring which may itself be substituted.
  • Compounds of formula (lll) may be prepared by routes analogous to those disdosed in US-A-3,622,569, US-A-4,416,880 and EP-A-0 161 617.
  • Aldehydes of formula RCHO are commer ⁇ ally available or can be obtained by oxidizing commerdally available alcohols, using a suitable oxidizing agent such as pyridinium chlorochromate or dichromate.
  • B is hydrogen, halogen or a group of formula:
  • Methyl endo 7-oxabicyclo[2.2.1]heptane-2-carboxylate (1.04g; W.L. Nelson, D.R. Allen, and F.F. Vicenzi, J.Med.Chem., 1971, 14, 698; W.L. Nelson and D.R. Allen, J.Het.Chem., 1972, 9, 561) was stirred in anhydrous dichloromethane (10ml) under argon at -90°C and treated with 1.0M di-isobutylaluminium hydride in hexane (6.7ml). After 2h at the same temperature, methanol (1ml) was added, foliowed by a solution of sodium sulphate (2g) in water (20ml).
  • E-isomer (0.90g) was a colourless oil; ⁇ max (CHCI 3 ) 1710 and 1620cm- 1 ; ⁇ (CDCl 3 ) 1.00-1.50 (6H, m), 1.65-1.88 (1H, m), 2.40-2.60 (2H, m), 2.66-2.83 (1H, m), 3.11 and 3.14 (6H, 2s), 3.74 (3H, s), 6.24 (1H, dd, J7.5Hz), 6.39 (1H, dd, J7.5Hz), 6.64 (1H, s), 6.75 (1H, d, J10.6Hz), and 8.60 (1H, s).

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

Abstract

Cette invention concerne des bêta-lactamines de formule (I) ou un de leurs sels. Dans cette formule, X représente hydrogène ou un groupe NHR1, dans lequel R1 représente hydrogène ou un groupe protecteur amino, et R représente un groupe bicyclique ou tricyclique spiro, fusionné ou ponté facultativement substitué, contenant facultativement au moins un hétéroatome sélectionné parmi oxygène, azote et soufre. Ces nouveaux composés sont utiles dans le traitement des infections bactériennes chez l'homme et les animaux.
PCT/GB1992/001484 1991-08-17 1992-08-10 Derives d'acide acrylamido-penicillanique substitue WO1993004070A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB919117783A GB9117783D0 (en) 1991-08-17 1991-08-17 Novel compounds
GB9117783.2 1991-08-17

Publications (1)

Publication Number Publication Date
WO1993004070A1 true WO1993004070A1 (fr) 1993-03-04

Family

ID=10700133

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1992/001484 WO1993004070A1 (fr) 1991-08-17 1992-08-10 Derives d'acide acrylamido-penicillanique substitue

Country Status (3)

Country Link
AU (1) AU2399292A (fr)
GB (1) GB9117783D0 (fr)
WO (1) WO1993004070A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0049448A2 (fr) * 1980-10-08 1982-04-14 Bayer Ag Antibiotiques bêta-lactame, leur préparation et compositions les contenant
EP0337643A2 (fr) * 1988-04-06 1989-10-18 Beecham Group Plc Dérivés d'acide pénicillanique 6-acrylamino substitué, préparation et application
EP0421751A2 (fr) * 1989-10-05 1991-04-10 Beecham Group p.l.c. Esters d'acide acrylamidopénicillanique substitués
EP0421752A2 (fr) * 1989-10-05 1991-04-10 Beecham Group p.l.c. Dérivés d'acide acrylamido-pénicillanique substitués

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0049448A2 (fr) * 1980-10-08 1982-04-14 Bayer Ag Antibiotiques bêta-lactame, leur préparation et compositions les contenant
EP0337643A2 (fr) * 1988-04-06 1989-10-18 Beecham Group Plc Dérivés d'acide pénicillanique 6-acrylamino substitué, préparation et application
EP0421751A2 (fr) * 1989-10-05 1991-04-10 Beecham Group p.l.c. Esters d'acide acrylamidopénicillanique substitués
EP0421752A2 (fr) * 1989-10-05 1991-04-10 Beecham Group p.l.c. Dérivés d'acide acrylamido-pénicillanique substitués

Also Published As

Publication number Publication date
GB9117783D0 (en) 1991-10-09
AU2399292A (en) 1993-03-16

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