GB1065715A - Tetracycline derivatives - Google Patents
Tetracycline derivativesInfo
- Publication number
- GB1065715A GB1065715A GB2663764A GB2663764A GB1065715A GB 1065715 A GB1065715 A GB 1065715A GB 2663764 A GB2663764 A GB 2663764A GB 2663764 A GB2663764 A GB 2663764A GB 1065715 A GB1065715 A GB 1065715A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compound
- formula
- bond
- benzyl
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to tetracycline compounds having the following formulae <FORM:1065715/C2/1> wherein R1 is H, benzyl, phenethyl, cyclohexyl or C2- 6 alkyl, R2 is H, hydroxy -C2- 6 alkyl or C2- 6 alkyl; and when R1 or R2 is H, the other R is other than H, X is H or CH3, X1 is OH, or X and X1 together are methylene, or X1 represents a second bond connecting C6 and C5a, X2 is H or OH, X being CH3 when the C6-C5a bond is a single bond and/or X2 is OH, and Y is H or chloro, <FORM:1065715/C2/2> wherein at least one of R1 and R2 is H, X, X2, Y and R1 and R2 having the above meanings, and also to their salts. Compounds of Formula I are prepared by alkylating a compound of Formula II, e.g. by means of an alkyl, hydroxyalkyl, alicylic or aralkyl iodide or alkyl sulphate in the presence of an acid acceptor (base) or acid scavenger (propylene oxide). Alternatively, an aldehyde or ketone in the presence of a reducing agent and a catalyst may be used. Compounds of general Formula II are prepared by reacting a compound of Formula III <FORM:1065715/C2/3> in which X, X1, X2 and Y are as defined above, Z is H, Cl or F, X being CH3 when the 6-5a bond is a single bond and Z is H, or Z is halogen when X and X1 are together methylene, and when X1 is OH, the compound III being also in its 4-6 hemiketal form, with ammonia or a primary amine under reductive amination conditions; or with a compound H2NR3 wherein R3 is OH, NHCONH2, NHC(NH)NH2, NHCSNH2, 4-(beta-hydroxyethyl) piperazino or NR4R5 wherein R4 is H, C1- 6\ alkyl, phenyl, benzyl or cyclohexyl and R5 is H, C1- 6 alkyl, phenyl or benzyl, said compound of formula H2NR3 being reacted as a free base or as its acid salt and, if one of the reactants is a compound of formula H2NR3, reducing the reaction product.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US36034564A | 1964-04-16 | 1964-04-16 | |
US36043564A | 1964-04-16 | 1964-04-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1065715A true GB1065715A (en) | 1967-04-19 |
Family
ID=27000853
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2663764A Expired GB1065715A (en) | 1964-04-16 | 1964-06-24 | Tetracycline derivatives |
GB733066A Expired GB1065716A (en) | 1964-04-16 | 1964-06-26 | Tetracycline derivatives and process for their preparation |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB733066A Expired GB1065716A (en) | 1964-04-16 | 1964-06-26 | Tetracycline derivatives and process for their preparation |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE650353A (en) |
CH (2) | CH462149A (en) |
FR (1) | FR4359M (en) |
GB (2) | GB1065715A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES315101A1 (en) * | 1965-07-08 | 1966-01-01 | Folch Vazquez Conrado | Salts of Tetracycline Antibiotics |
EP1805134B1 (en) * | 2004-10-25 | 2012-06-20 | Paratek Pharmaceuticals, Inc. | 4-aminotetracyclines and methods of use thereof |
JP6301335B2 (en) * | 2012-08-31 | 2018-03-28 | テトラフェース ファーマシューティカルズ,インコーポレイテッド | Tetracycline compound |
EP3529236B1 (en) | 2016-10-19 | 2024-02-07 | Tetraphase Pharmaceuticals, Inc. | Crystalline forms of eravacycline |
-
1964
- 1964-06-24 GB GB2663764A patent/GB1065715A/en not_active Expired
- 1964-06-26 GB GB733066A patent/GB1065716A/en not_active Expired
- 1964-07-08 CH CH893964A patent/CH462149A/en unknown
- 1964-07-08 CH CH388767A patent/CH462155A/en unknown
- 1964-07-09 FR FR981287A patent/FR4359M/fr not_active Expired
- 1964-07-09 BE BE650353D patent/BE650353A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
BE650353A (en) | 1965-01-11 |
CH462149A (en) | 1968-09-15 |
CH462155A (en) | 1968-09-15 |
FR4359M (en) | 1966-08-22 |
GB1065716A (en) | 1967-04-19 |
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