GB898658A - Therapeutic glutarimide derivatives and preparation thereof - Google Patents

Therapeutic glutarimide derivatives and preparation thereof

Info

Publication number
GB898658A
GB898658A GB16593/60A GB1659360A GB898658A GB 898658 A GB898658 A GB 898658A GB 16593/60 A GB16593/60 A GB 16593/60A GB 1659360 A GB1659360 A GB 1659360A GB 898658 A GB898658 A GB 898658A
Authority
GB
United Kingdom
Prior art keywords
dihydro
esters
desacetyl
formula
compound
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
GB16593/60A
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.)
Pfizer Inc
Original Assignee
Pfizer Inc
Charles Pfizer and Co Inc
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 Pfizer Inc, Charles Pfizer and Co Inc filed Critical Pfizer Inc
Publication of GB898658A publication Critical patent/GB898658A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/20—Bacteria; Culture media therefor
    • C12N1/205—Bacterial isolates
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/465—Streptomyces

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Virology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compound "Dihydro E-73" of structural formula <FORM:0898658/IV (b)/1> its esters, its N-alkyl derivatives and desacetyl dihydro E-73 and esters thereof, together with processes for their preparation by reducing the keto group of compound E-73 or an ester thereof to a secondary hydroxyl group, preferably by hydrogenation over a platinum catalyst or with a metal hydride under conditions that avoid hydrolysis of the imide and acetoxyl groups, and thereafter, if desired, N-alkylating, mono- or di-acylating dihydro E-73, or hydrolysing its 5-acyloxy group to yield a desacetyl derivative which may then be mono-, di-or tri-acylated. Dihydro E-73 on treatment with an aldehyde or ketone yields a 1,3-dioxane derivative. Examples detail the preparation of dihydro E-73, its monoacetate, benzoate and stearate, diacetate, dibenzoate, dipalmitate and other esters, its benzylidene, N-methyl and desacetyl derivatives, and its partial hydrolysis to a substituted glutaric acid lactone of formula <FORM:0898658/IV (b)/2> which is then esterified with diazomethane and ammonolysed to give the diamide of formula <FORM:0898658/IV (b)/3> The isolation of Compound E-73 from a fermentation broth of Streptomyces albulus ATCC 12757 is described.ALSO:Pharmaceutical compositions having antitumour and antiprotozoal activity comprise Compound Dihydro E-73 having the formula <FORM:0898658/VI/1> desacetyl dihydro E-73, esters of these compounds or an N-alkyl derivative of dihydro E-73 together with a pharmaceutically acceptable carrier. The compositions may contain other medicinal agents including local anaesthetics, antibiotics, antibacterial agents, hypnotics, analgesics and also buffering agents and inorganic salts, and may be administered orally or preferably p parenterally either in aqueous solution or in suspension.
GB16593/60A 1959-05-18 1960-05-11 Therapeutic glutarimide derivatives and preparation thereof Expired GB898658A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US81369559A 1959-05-18 1959-05-18

Publications (1)

Publication Number Publication Date
GB898658A true GB898658A (en) 1962-06-14

Family

ID=25213107

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16593/60A Expired GB898658A (en) 1959-05-18 1960-05-11 Therapeutic glutarimide derivatives and preparation thereof

Country Status (2)

Country Link
FR (1) FR477M (en)
GB (1) GB898658A (en)

Also Published As

Publication number Publication date
FR477M (en) 1961-05-02

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