GB808702A - Production of tertiary-butyl derivatives of anhydrotetracyclines - Google Patents

Production of tertiary-butyl derivatives of anhydrotetracyclines

Info

Publication number
GB808702A
GB808702A GB3307/56A GB330756A GB808702A GB 808702 A GB808702 A GB 808702A GB 3307/56 A GB3307/56 A GB 3307/56A GB 330756 A GB330756 A GB 330756A GB 808702 A GB808702 A GB 808702A
Authority
GB
United Kingdom
Prior art keywords
tertiary butyl
derivatives
produced
acid
butyl 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
GB3307/56A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB808702A publication Critical patent/GB808702A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/65—Tetracyclines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
    • C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to the tertiary butyl derivatives of anhydrotetracycline, anhydrochlortetracycline and anhydrobromtetracycline, particularly the mono- and di-tertiary butyl derivatives, which have antibacterial activity. The compounds are produced by reacting the nitrile of the appropriate tetracycline with a strong mineral acid especially sulphuric acid. The reaction is carried out by mixing the nitrile with glacial acetic acid or other fatty acid such as formic, propionic, butyric, valeric or caproic, or with an organic solvent such as methoxyethanol or dimethoxyethane, and treating with isobutylene. In the examples, concentrated sulphuric acid is added to a slurry of tetracyclinonitrile or chlortetracyclinonitrile in glacial acetic acid and isobutylene gas is bubbled through the solution for 4 hours at 20 DEG C. Both the mono- and di-tertiary butyl derivatives are produced. In the case of tetracycline, the derivatives are separated by partition chromatography employing methoxyethanol as the stationary phase and petroleum ether as the mobile phase. In the case of chlortetracycline, the reaction solution is diluted with benzene, extracted with water, the aqueous extract is cooled and allowed to stand. The crystalline solid produced is dissolved in methanol, adjusted to pH 4.0 by means of sodium acetate and the tertiary butyl anhydrochlortetracycline which crystallizes is treated with carbon and then crystallized from ethanol. Reference has been directed by the Comptroller to Specification 766,512.
GB3307/56A 1955-02-14 1956-02-02 Production of tertiary-butyl derivatives of anhydrotetracyclines Expired GB808702A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US808702XA 1955-02-14 1955-02-14

Publications (1)

Publication Number Publication Date
GB808702A true GB808702A (en) 1959-02-11

Family

ID=22160171

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3307/56A Expired GB808702A (en) 1955-02-14 1956-02-02 Production of tertiary-butyl derivatives of anhydrotetracyclines

Country Status (1)

Country Link
GB (1) GB808702A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3159631A (en) * 1960-08-30 1964-12-01 Smith Kline French Lab Nu-aminomethyltetracycline derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3159631A (en) * 1960-08-30 1964-12-01 Smith Kline French Lab Nu-aminomethyltetracycline derivatives

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