GB859580A - Production of 12a-deoxytetracyclines - Google Patents

Production of 12a-deoxytetracyclines

Info

Publication number
GB859580A
GB859580A GB33564/58A GB3356458A GB859580A GB 859580 A GB859580 A GB 859580A GB 33564/58 A GB33564/58 A GB 33564/58A GB 3356458 A GB3356458 A GB 3356458A GB 859580 A GB859580 A GB 859580A
Authority
GB
United Kingdom
Prior art keywords
deoxytetracycline
hydrogen
demethyl
tetracycline
acid
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
GB33564/58A
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 GB859580A publication Critical patent/GB859580A/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
    • 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)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention relates to 12a-deoxytetracyclines of formula: <FORM:0859580/IV(b)/1> wherein R1 is hydrogen or chlorine, R2 is hydrogen or methyl, and R3 is hydrogen or hydroxy, with the proviso that at least one of the substituents R1, R3 and R3 is hydrogen; and acid addition salts. They are 12a-deoxytetracycline, 6-demethyl-6, 12a-dideoxytetracycline 7-chloro-6-demethyl -12a-deoxytetracycline, 6, 12a dideoxytetracycline and 6-demethyl-12a deoxytetracycline. They are prepared by contacting the corresponding tetracycline having a 12a-hydroxy substituent with metallic zinc in an aqueous alkaline solution so as to cause reduction of 12a-hydroxy substituent. Aqueous sodium or potassium hydroxide may be used but aqueous ammonia is preferred at pH 10 to 13 containing 10 to 20% ammonia. The concentration of the tetracycline may be 4% w/v and 2 to 4 parts zinc per part of tetracycline are used. The temperature is 10-50 DEG C. The 12a-deoxytetracycline is recovered by acidifying the reaction mixture and extracting with a water-imiscible solvent such as ether, methyl acetate, ethyl acetate, methylene chloride or chloroform. Acid salts are prepared by treating the amphoteric compound with an acid, the mineral acids, e.g. hydrochloric, sulphuric, nitric and phosphoric being preferred. Specifications 845,649, 855,169, 855,170 and 859,581 are referred to.
GB33564/58A 1957-10-29 1958-10-21 Production of 12a-deoxytetracyclines Expired GB859580A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US859580XA 1957-10-29 1957-10-29

Publications (1)

Publication Number Publication Date
GB859580A true GB859580A (en) 1961-01-25

Family

ID=22195082

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33564/58A Expired GB859580A (en) 1957-10-29 1958-10-21 Production of 12a-deoxytetracyclines

Country Status (1)

Country Link
GB (1) GB859580A (en)

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