GB855170A - 6-demethyl-6-deoxytetracycline and the 4-epimers thereof - Google Patents
6-demethyl-6-deoxytetracycline and the 4-epimers thereofInfo
- Publication number
- GB855170A GB855170A GB522158A GB522158A GB855170A GB 855170 A GB855170 A GB 855170A GB 522158 A GB522158 A GB 522158A GB 522158 A GB522158 A GB 522158A GB 855170 A GB855170 A GB 855170A
- Authority
- GB
- United Kingdom
- Prior art keywords
- deoxytetracycline
- demethyl
- acid
- hydrogen
- aluminium
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to 6-demethyl-6-deoxytetracycline having the formula: <FORM:0855170/IV(b)/1> the 4-epimer thereof, and salts of these compounds with an acid or a base and complexes with metal salts, e.g. aluminium, magnesium and calcium, e.g. aluminium gluconate. The base is obtained by catalytically reducing by means of hydrogen a 6-demethyltetracycline of formula: <FORM:0855170/IV(b)/2> wherein Z is hydrogen, chlorine or bromine, or the 4-epimer thereof, in a solvent solution in the presence of a substance which forms a chelate ring with a peri-dioxygenated hydro-naphthalene, e.g. boric acid, boron trihalides such as boron trifluoride, aluminium salts such as aluminium chloride and magnesium salts such as magnesium acetate. Where Z is hydrogen one mole of hydrogen is used and where Z is chlorine or bromine 2 moles of hydrogen are used. The reduction is carried out at temperatures of 0 DEG C. to 100 DEG C. and preferably at room temperature to 50 DEG C. and at hydrogen pressures of 1/2 to 100 atmospheres. The catalyst may be a metal of the platinum family especially 5% palladium hydroxide on charcoal. Specified solvents are water, dioxane, glacial acetic acid, 2-ethoxyethanol and ethyl acetate; a mixture of water and dimethylformamide (1 : 1) containing perchloric acid is preferred. The 4-epimer of 6-demethyl-6-deoxytetracycline is produced by allowing a concentrated solution of 6-demethyl-6-deoxytetracycline to stand at pH 3 to 5 and preferably 3,5 to 4,5 for 1 to 7 days. A suitable solvent is methanol, ethanol, butanol, acetone, 2-ethoxyethanol, 2-methoxypropanol, glacial acetic acid, tetrahydrofuran dimethylformamide and mixtures thereof. A suitable buffer is sodium dihydrogen phosphate. Acid salts are prepared by treating the 6-demethyl-6-deoxytetracycline with an acid, e.g. hydrochloric, sulphuric, phosphoric and trichloroacetic at pH below 4. Alkali metal and alkaline earth metal salts are obtained by treating the 6-demethyl-6-deoxytetracycline with a base such as sodium hydroxide, potassium hydroxide, calcium hydroxide or barium hydroxide at a pH above 6,0. The free 6-demethyl-6-deoxytetracycline may be obtained by adjusting a solution of the salt to pH 4 to 6. 6-demethyl-6-deoxytetracycline aluminium gluconate complex is produced by mixing 6-demethyl-6-deoxytetracycline with aluminium gluconate in aqueous solution. 6-demethyl-6-deoxytetracycline is a broad spectrum antibiotic more active against staphyloccus aureus than tetracycline and possessing some stability in acid and alkaline aqueous media. Specification 855,169 is referred to.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US64322757A | 1957-03-01 | 1957-03-01 | |
US64321857A | 1957-03-01 | 1957-03-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB855170A true GB855170A (en) | 1960-11-30 |
Family
ID=43466745
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB522158A Expired GB855170A (en) | 1957-03-01 | 1958-02-18 | 6-demethyl-6-deoxytetracycline and the 4-epimers thereof |
GB522258A Expired GB845649A (en) | 1957-03-01 | 1958-02-18 | 6-deoxytetracycline and 6-deoxyoxytetracycline |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB522258A Expired GB845649A (en) | 1957-03-01 | 1958-02-18 | 6-deoxytetracycline and 6-deoxyoxytetracycline |
Country Status (7)
Country | Link |
---|---|
AT (2) | AT206434B (en) |
CH (2) | CH384568A (en) |
DE (2) | DE1076675B (en) |
DK (2) | DK92251C (en) |
FR (2) | FR1241126A (en) |
GB (2) | GB855170A (en) |
MC (2) | MC49A1 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1430859A (en) * | 1960-05-23 | 1966-05-25 | ||
DE1793556C2 (en) * | 1960-05-23 | 1982-06-16 | Pfizer Inc., 10017 New York, N.Y. | 7-chloro-5-hydroxy-6-deoxy-6-desmethyl-6-methylene tetracycline, 5-hydroxy-6-deoxy-6-desmethyl-6-methylene tetracycline and their salts with acids and bases and antibiotics containing these compounds |
US20030171340A1 (en) * | 2002-02-07 | 2003-09-11 | Jenefir Isbister | Methods of disease treatment using metal-complexed tetracycline antibiotics |
AU2004261143B2 (en) | 2003-07-25 | 2009-11-05 | Allergan Pharmaceuticals International Limited | A doxycycline metal complex in a solid dosage form |
CN107445855B (en) * | 2017-08-07 | 2018-12-14 | 绍兴市逸晨医疗科技有限公司 | A kind of preparation method of Doxycycline Hyclate impurity C |
-
1958
- 1958-02-18 GB GB522158A patent/GB855170A/en not_active Expired
- 1958-02-18 GB GB522258A patent/GB845649A/en not_active Expired
- 1958-02-20 CH CH5612158A patent/CH384568A/en unknown
- 1958-02-20 CH CH5612058A patent/CH382728A/en unknown
- 1958-02-21 FR FR758758A patent/FR1241126A/en not_active Expired
- 1958-02-21 MC MC57A patent/MC49A1/en unknown
- 1958-02-21 FR FR758759A patent/FR1241127A/en not_active Expired
- 1958-02-21 MC MC59A patent/MC48A1/en unknown
- 1958-02-25 DE DEA28947A patent/DE1076675B/en active Pending
- 1958-02-25 DE DEA28948A patent/DE1076676B/en active Pending
- 1958-02-27 DK DK69558A patent/DK92251C/en active
- 1958-02-27 DK DK69458A patent/DK92351C/en active
- 1958-02-28 AT AT146658A patent/AT206434B/en active
- 1958-02-28 AT AT146758A patent/AT206435B/en active
Also Published As
Publication number | Publication date |
---|---|
CH384568A (en) | 1964-11-30 |
AT206435B (en) | 1959-11-25 |
MC49A1 (en) | 1958-09-11 |
DE1076675B (en) | 1960-03-03 |
DK92351C (en) | 1961-12-11 |
GB845649A (en) | 1960-08-24 |
DE1076676B (en) | 1960-03-03 |
FR1241127A (en) | 1960-12-20 |
DK92251C (en) | 1961-11-27 |
MC48A1 (en) | 1958-09-11 |
CH382728A (en) | 1964-10-15 |
FR1241126A (en) | 1960-12-20 |
AT206434B (en) | 1959-11-25 |
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