GB910874A - Tetracycline compounds and the preparation thereof - Google Patents

Tetracycline compounds and the preparation thereof

Info

Publication number
GB910874A
GB910874A GB812760A GB812760A GB910874A GB 910874 A GB910874 A GB 910874A GB 812760 A GB812760 A GB 812760A GB 812760 A GB812760 A GB 812760A GB 910874 A GB910874 A GB 910874A
Authority
GB
United Kingdom
Prior art keywords
desdimethylamino
deoxy
prepared
deoxytetracyclines
deoxytetracycline
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
GB812760A
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
Priority claimed from US813652A external-priority patent/US3047617A/en
Priority claimed from US813653A external-priority patent/US2976318A/en
Priority claimed from US813654A external-priority patent/US3002021A/en
Priority claimed from US5336A external-priority patent/US3043876A/en
Application filed by Pfizer Inc, Charles Pfizer and Co Inc filed Critical Pfizer Inc
Publication of GB910874A publication Critical patent/GB910874A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C233/00—Carboxylic acid amides

Abstract

12a-Deoxytetracyclines may be prepared by treating the corresponding 12a-(O-monoacyl), 12a-(O-arylcarbamyl) or 10,12a or 12,12a or 5,12a-(O,O-diacyl) compound with hydrogen in the presence of a hydrogenolysis catalyst such as palladium, platinum black or platinum dioxide. When a di-acyl compound is used as starting material, the resulting 12a-deoxy mono-acyl compound may be further treated with an alkaline agent such as aqueous ammonia to form a 12a-deoxy compound. Examples describe the production of many 12a-deoxy compounds of which the following are typical: 12a-deoxytetracycline, 6-demethyl-6,12a - dideoxytetracycline, 5 - hydroxy - 12a - deoxy-tetracycline and 4-desdimethylamino-12a-deoxytetracycline. 5a,6-anhydro compounds may be prepared by treating 6-hydroxy-12a-deoxytetracyclines with an acid dehydrating agent, and 4a,12a-anhydro-4-desdimethylamino tetracyclines may be prepared by treating the corresponding 12a-deoxytetracycline with a peracid in an inert solvent or with an aminonitrogen alkylating agent in the presence of an acid scavanger. Hydrogenation of the 4a,12a - anhydro - 4 - desdimethylamino-tetracyclines provides 4 - desdimethylamino-12a-deoxytetracyclines. Pharmaceutical compositions may be prepared including any of the above compounds which have pharmaceutical activity, and the pharmaceutically acceptable acid addition salts thereof.
GB812760A 1959-05-18 1960-03-08 Tetracycline compounds and the preparation thereof Expired GB910874A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US813652A US3047617A (en) 1959-05-18 1959-05-18 Alkanoic acid esters of 5-hydroxytetracycline and process for preparation
US813653A US2976318A (en) 1959-05-18 1959-05-18 Tetracycline derivatives and process of producing the same
US813654A US3002021A (en) 1959-05-18 1959-05-18 New derivatives of the tetracycline-type antibiotics
US5336A US3043876A (en) 1960-01-29 1960-01-29 4a, 12a-anhydro-4-desdimethylaminotetracycline and analogs thereof

Publications (1)

Publication Number Publication Date
GB910874A true GB910874A (en) 1962-11-21

Family

ID=27485479

Family Applications (1)

Application Number Title Priority Date Filing Date
GB812760A Expired GB910874A (en) 1959-05-18 1960-03-08 Tetracycline compounds and the preparation thereof

Country Status (2)

Country Link
DE (1) DE1141638B (en)
GB (1) GB910874A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2812349A (en) * 1954-03-11 1957-11-05 Pfizer & Co C Alkanoic acid esters of tetracycline antibiotics
US2731497A (en) * 1954-05-14 1956-01-17 American Cyanamid Co Production of tetracycline

Also Published As

Publication number Publication date
DE1141638B (en) 1962-12-27

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