GB785047A - Anhydrotetracycline compounds - Google Patents

Anhydrotetracycline compounds

Info

Publication number
GB785047A
GB785047A GB37526/54A GB3752654A GB785047A GB 785047 A GB785047 A GB 785047A GB 37526/54 A GB37526/54 A GB 37526/54A GB 3752654 A GB3752654 A GB 3752654A GB 785047 A GB785047 A GB 785047A
Authority
GB
United Kingdom
Prior art keywords
acid
water
hydrogen chloride
sulphuric
salts
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
GB37526/54A
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 GB785047A publication Critical patent/GB785047A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to anhydrodesdimethylaminooxytetracycline, anhydrodiacetyloxytetracycline, anhydrodestimethylaminodesoxyoxytetracycline, anhydrodesdimethylaminochlortetracycline, anhydrodesdimethylaminotetracycline, anhydromethomycin, anhydroisodesdimethylaminooxytetracycline, and salts thereof. The anhydro compounds are prepared by reacting the appropriate tetracycline with an acid dehydrating agent until one molecule of water is removed, the reaction taking place in the presence of water but preferably in a substantially water-free polar organic sulvent at temperatures generally not greater than 50 DEG C. Preferred reactants are: (a) anhydrous hydrogen chloride in methanol; (b) anhydrous hydrogen chloride in acetone; (c) concentrated sulphuric acid in dimethylformamide; and (d) hydrogen chloride in acetic acid. Other dehydrating agents which may be used are mineral acids such as sulphuric, hydrobromic, phosphoric and anhydrides thereof; potassium acid sulphate, sodium acid sulphate, sodium dihydrogen phosphate, benzene sulphonic acid, toluene sulphonic acid and chloracetic acid. Anhydro compounds are generally insoluble at pH 4 to 7 and may be isolated by (a) neutralization followed by concentration or merely by diluting with water in the case of anhydrous solution; (b) extraction with a water-immiscible solvent such as butanol or benzyl alcohol in the case of aqueous solutions. The anhydrotetracyclines may be in the form of salts with (a) acids such as hydrochloric and sulphuric bases such as the alkali metals and alkaline earth metals, or in the form of an acetone derivative.
GB37526/54A 1954-01-15 1954-12-29 Anhydrotetracycline compounds Expired GB785047A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US785047XA 1954-01-15 1954-01-15

Publications (1)

Publication Number Publication Date
GB785047A true GB785047A (en) 1957-10-23

Family

ID=22144434

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37526/54A Expired GB785047A (en) 1954-01-15 1954-12-29 Anhydrotetracycline compounds

Country Status (1)

Country Link
GB (1) GB785047A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3043875A (en) * 1959-10-22 1962-07-10 Pfizer & Co C Halogenated tetracycline derivatives and processes for their preparation
US3043876A (en) * 1960-01-29 1962-07-10 Pfizer & Co C 4a, 12a-anhydro-4-desdimethylaminotetracycline and analogs thereof
US3081346A (en) * 1960-01-29 1963-03-12 Pfizer & Co C Novel 12alpha-(o-formyl)tetracyclines
US3159631A (en) * 1960-08-30 1964-12-01 Smith Kline French Lab Nu-aminomethyltetracycline derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3043875A (en) * 1959-10-22 1962-07-10 Pfizer & Co C Halogenated tetracycline derivatives and processes for their preparation
US3043876A (en) * 1960-01-29 1962-07-10 Pfizer & Co C 4a, 12a-anhydro-4-desdimethylaminotetracycline and analogs thereof
US3081346A (en) * 1960-01-29 1963-03-12 Pfizer & Co C Novel 12alpha-(o-formyl)tetracyclines
US3159631A (en) * 1960-08-30 1964-12-01 Smith Kline French Lab Nu-aminomethyltetracycline derivatives

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