IE36677B1 - Manufacture of 6-methylenetetracyclines - Google Patents
Manufacture of 6-methylenetetracyclinesInfo
- Publication number
- IE36677B1 IE36677B1 IE1381/71A IE138171A IE36677B1 IE 36677 B1 IE36677 B1 IE 36677B1 IE 1381/71 A IE1381/71 A IE 1381/71A IE 138171 A IE138171 A IE 138171A IE 36677 B1 IE36677 B1 IE 36677B1
- Authority
- IE
- Ireland
- Prior art keywords
- tetracycline
- acid salt
- halo
- base
- methylene
- Prior art date
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
1370318 Preparation of 6-methylenetetracyclines RACHELLE LABORATORIES ITALIA SpA 21 Dec 1971 [28 Dec 1970 26 Oct 1971] 59247/71 Heading C2A A process for the preparation of a 6-methylenetetracycline comprises halogenating a tetracycline base or an acid salt thereof in solution at sub-ambient temperatures while maintaining the pH of the reaction mixture at from 3À0 to 5À0 to spontaneously crystallize the 11a-halo-6,12- hemiketal substantially entirely in the enolic form. Then the 11a-halo-6,12-hemiketal base is converted to the corresponding acid salt, e.g. the perchlorate, this salt is dehydrated to the corresponding 11a-halo-6-methylene tetracycline and this is dehalogenated to provide the desired 6-methylene tetracycline. The hemiketal base may be treated with acid at a temperature from -10 C. to 20 C. in order to convert it to the corresponding acid salt. The 6-methylene tetracyclines which may be prepared include 6- methylene-5-oxytetracycline, for which the initial tetracycline reactant is 5-oxytetracycline. The 11a-halo-6-methylenetetracycline may be dehalogenated to form an acid salt of the 6- methylene tetracycline and the acid salt converted to the free base of the desired 6-methylenetetracycline by neutralizing it at a temperature of from 50 C. to 90 C. in an aqueous solution maintained at a pH of from 6À5 to 7À5. The 11a-halo-6,12-hemiketal base may be formed by halogenating the tetracycline base or acid salt thereof in solution at a temperature below 0 C. and at a pH of from 3À5 to 5À0.
[GB1370318A]
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10168870A | 1970-12-28 | 1970-12-28 | |
US19233671A | 1971-10-26 | 1971-10-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE36677L IE36677L (en) | 1972-06-28 |
IE36677B1 true IE36677B1 (en) | 1977-02-02 |
Family
ID=26798521
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE1381/71A IE36677B1 (en) | 1970-12-28 | 1971-11-01 | Manufacture of 6-methylenetetracyclines |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS5343956B1 (en) |
BE (1) | BE777356A (en) |
CA (1) | CA949066A (en) |
CH (1) | CH586191A5 (en) |
DE (1) | DE2164840A1 (en) |
DK (1) | DK139674B (en) |
FR (1) | FR2120865A5 (en) |
GB (1) | GB1370318A (en) |
IE (1) | IE36677B1 (en) |
IL (1) | IL38383A (en) |
NL (1) | NL152544B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106946816A (en) * | 2017-04-12 | 2017-07-14 | 扬州联博药业有限公司 | A kind of preparation method of chloro terramycin |
CN111393319B (en) * | 2020-04-24 | 2023-03-28 | 山东国邦药业有限公司 | Preparation method of oxytetracycline chloride |
-
1971
- 1971-11-01 IE IE1381/71A patent/IE36677B1/en unknown
- 1971-11-09 CA CA127,257A patent/CA949066A/en not_active Expired
- 1971-12-16 IL IL38383A patent/IL38383A/en unknown
- 1971-12-21 GB GB5924771A patent/GB1370318A/en not_active Expired
- 1971-12-23 DK DK631871AA patent/DK139674B/en unknown
- 1971-12-24 FR FR7146557A patent/FR2120865A5/fr not_active Expired
- 1971-12-24 CH CH1893371A patent/CH586191A5/xx not_active IP Right Cessation
- 1971-12-24 JP JP10478371A patent/JPS5343956B1/ja active Pending
- 1971-12-27 DE DE19712164840 patent/DE2164840A1/en not_active Ceased
- 1971-12-28 BE BE777356A patent/BE777356A/en unknown
- 1971-12-28 NL NL717117996A patent/NL152544B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE2164840A1 (en) | 1972-07-06 |
NL152544B (en) | 1977-03-15 |
JPS5343956B1 (en) | 1978-11-24 |
DK139674C (en) | 1979-09-10 |
IL38383A0 (en) | 1972-02-29 |
FR2120865A5 (en) | 1972-08-18 |
BE777356A (en) | 1972-04-17 |
CH586191A5 (en) | 1977-03-31 |
GB1370318A (en) | 1974-10-16 |
CA949066A (en) | 1974-06-11 |
IE36677L (en) | 1972-06-28 |
NL7117996A (en) | 1972-06-30 |
IL38383A (en) | 1974-12-31 |
DK139674B (en) | 1979-03-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
IE42340L (en) | 11,12-secoprostaglandins | |
ES423325A1 (en) | Production of synthetic fluorspar | |
IE36677L (en) | Manufacture of 6-methylenetetracyclines | |
IE35673L (en) | Alpha-6-deoxytetracyclines | |
GB1349062A (en) | Process for the preparation of leuco crystal violet lactone | |
ES406320A1 (en) | Process for the preparation of 8,14-cedranoxide | |
ES448524A1 (en) | Synthesis of m-benzoyl-hydratropic acid | |
AU3859172A (en) | Method of manufacture ofan acid compound with controlled release | |
SU371193A1 (en) | METHOD OF OBTAINING 1,3-DICHLORADAMANTAN | |
JPS5214708A (en) | Process for preparation of choline chloride | |
GB1245071A (en) | Improved process for the manufacture of 5-alkenyl-2-norbornenes | |
SU458544A1 (en) | Method for producing fatty acid amides | |
SU463323A1 (en) | Process for preparing substituted lactones of 2-(2'-hydroxyethyl)-nicotinic acid or their n-oxides | |
US3341590A (en) | Process for preparing oximes | |
SU401132A1 (en) | The method of obtaining 1-adamantanecarboxylic acid | |
JPS55167243A (en) | Preparation of aluminum soap for gelation of high-boiling organic solvent and animal or vegetable oil | |
JPS5236622A (en) | Process for preparation of bromoacetic acid | |
GB1332757A (en) | Manufacture of aromatic amino compounds | |
ES391289A1 (en) | 6-methylene-tetracyclines prepn - via the 11a-halo-6,12-hemiacetal | |
IE34961L (en) | Alicyclic ketenes | |
GB1046047A (en) | Process for the manufacture of trans-2-chlorobutene-(2) | |
GB1041537A (en) | Mixtures containing crotonylidene diurea | |
GB1319230A (en) | 4-aminoindane-5,7-disulphonic acid and a method for the preparation thereof | |
GB1346876A (en) | Process for prepar'ng naphthalene-1,8-dicarboxylic acid imide | |
JPS5262239A (en) | Process for preparation of 6-chloro-3-toluidine-4-sulfonic acid |