GB1034933A - 4-demethylamino-4-substituted amino 6-demethyl tetracyclines - Google Patents
4-demethylamino-4-substituted amino 6-demethyl tetracyclinesInfo
- Publication number
- GB1034933A GB1034933A GB41431/63A GB4143163A GB1034933A GB 1034933 A GB1034933 A GB 1034933A GB 41431/63 A GB41431/63 A GB 41431/63A GB 4143163 A GB4143163 A GB 4143163A GB 1034933 A GB1034933 A GB 1034933A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- formula
- tetracycline
- hydroxy
- 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
-
- 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
Abstract
The invention relates to broad-spectrum tetracycline derivatives of formula <FORM:1034933/C2/1> where R is hydrogen or halogen; R1 is hydrogen or C1- 6 alkyl; R2 is C1- 6 alkyl or hydroxy C1- 6 alkyl, with the proviso that R1 and R2 cannot both be methyl. Specified are 4-dedimethyl-amino - 4 - methylamino - 6 - demethyltetracyline and -chlortetracycline; 4-dedimethylamino - 4 - ethylamino - 6 - demethyltetracycline and -bromotetracycline; 4 - dedimethylamino - 4 - methylethylamino - 6-demethyl-tetracycline and -7-iodo-tetracycline; 4 - n - propylamino-, 4 - n - butylamino-, 4 -(beta hydroxyethyl)-, 4-(3-hydroxypropy)-, 4 - methyl - n - propylamino-, 4 - diethylamino and 4 - methyl - (beta hydroxyethyl)amino-derivatives of 4-dedimethylamino-6-demethyl tetracycline. The 4-mono substituted amino compounds of formula <FORM:1034933/C2/2> where R is hydrogen or halogen and R2 is C1- 6 alkyl or hydroxy C1- 6 alkyl, are prepared by reductively aminating a 4-hydroxy-tetracyl-oxide of formula <FORM:1034933/C2/3> where R is as defined above, with a C1- 6 alkylamine or hydroxy C1- 6 alkylamine at 0 DEG to 50 DEG C. and 1 to 4 atmospheres. Compounds of Formula I are produced by alkylating the corresponding tetracycline of Formula I in which at least R1 or R2 is hydrogen by means of (a) an alkyl halide, alkyl sulphonate or alkyl sulphate or (b) an alkanal (i.e. aldehyde) in a reducing medium at 0 DEG C. to 50 DEG C. Hydrogen and a catalyst, zinc, tin or iron in hydrochloric acid, aluminium amalgam or formic acid are suitable reducing agents.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23394662A | 1962-10-29 | 1962-10-29 | |
US30582963A | 1963-08-30 | 1963-08-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1034933A true GB1034933A (en) | 1966-07-06 |
Family
ID=26927398
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB41431/63A Expired GB1034933A (en) | 1962-10-29 | 1963-10-21 | 4-demethylamino-4-substituted amino 6-demethyl tetracyclines |
Country Status (4)
Country | Link |
---|---|
CH (1) | CH439271A (en) |
ES (1) | ES292885A1 (en) |
FR (1) | FR3382M (en) |
GB (1) | GB1034933A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014036502A3 (en) * | 2012-08-31 | 2014-04-24 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
US8796245B2 (en) | 2008-08-08 | 2014-08-05 | Tetraphase Pharmaceuticals, Inc. | C7-fluoro substituted tetracycline compounds |
US9315451B2 (en) | 2009-05-08 | 2016-04-19 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
US9624166B2 (en) | 2009-08-28 | 2017-04-18 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
US10961190B2 (en) | 2016-10-19 | 2021-03-30 | Tetraphase Pharmaceuticals, Inc. | Crystalline forms of eravacycline |
-
1963
- 1963-10-21 GB GB41431/63A patent/GB1034933A/en not_active Expired
- 1963-10-25 ES ES292885A patent/ES292885A1/en not_active Expired
- 1963-10-28 FR FR951942A patent/FR3382M/en active Active
- 1963-10-29 CH CH1332963A patent/CH439271A/en unknown
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8796245B2 (en) | 2008-08-08 | 2014-08-05 | Tetraphase Pharmaceuticals, Inc. | C7-fluoro substituted tetracycline compounds |
US8906887B2 (en) | 2008-08-08 | 2014-12-09 | Tetraphase Pharmaceuticals, Inc. | C7-fluoro substituted tetracycline compounds |
US10072007B2 (en) | 2009-05-08 | 2018-09-11 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
US9315451B2 (en) | 2009-05-08 | 2016-04-19 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
US9624166B2 (en) | 2009-08-28 | 2017-04-18 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
US9573895B2 (en) | 2012-08-31 | 2017-02-21 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
WO2014036502A3 (en) * | 2012-08-31 | 2014-04-24 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
CN108276404A (en) * | 2012-08-31 | 2018-07-13 | 四相制药公司 | Tetracycline compound |
AU2013308504B2 (en) * | 2012-08-31 | 2016-11-10 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
EA031523B1 (en) * | 2012-08-31 | 2019-01-31 | Тетрафейз Фармасьютикалс, Инк. | Tetracycline compounds |
US10315992B2 (en) | 2012-08-31 | 2019-06-11 | Tetraphase Pharmaceuticals, Inc. | Tetracyline compounds |
EA036088B1 (en) * | 2012-08-31 | 2020-09-25 | Тетрафейз Фармасьютикалс, Инк. | Tetracycline compounds |
US10913712B2 (en) | 2012-08-31 | 2021-02-09 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
US10961190B2 (en) | 2016-10-19 | 2021-03-30 | Tetraphase Pharmaceuticals, Inc. | Crystalline forms of eravacycline |
US11578044B2 (en) | 2016-10-19 | 2023-02-14 | Tetraphase Pharmaceuticals, Inc. | Crystalline forms of eravacycline |
Also Published As
Publication number | Publication date |
---|---|
CH439271A (en) | 1967-07-15 |
ES292885A1 (en) | 1964-03-01 |
FR3382M (en) | 1965-06-21 |
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