GB1370318A - Manufacture of 6-methylenetetracyclines - Google Patents
Manufacture of 6-methylenetetracyclinesInfo
- Publication number
- GB1370318A GB1370318A GB5924771A GB5924771A GB1370318A GB 1370318 A GB1370318 A GB 1370318A GB 5924771 A GB5924771 A GB 5924771A GB 5924771 A GB5924771 A GB 5924771A GB 1370318 A GB1370318 A GB 1370318A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetracycline
- acid salt
- halo
- base
- methylene
- 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
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.
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1370318A true GB1370318A (en) | 1974-10-16 |
Family
ID=26798521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5924771A Expired GB1370318A (en) | 1970-12-28 | 1971-12-21 | 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) |
Cited By (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 |
| CN111393319A (en) * | 2020-04-24 | 2020-07-10 | 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
Cited By (3)
| 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 |
| CN111393319A (en) * | 2020-04-24 | 2020-07-10 | 山东国邦药业有限公司 | Preparation method of oxytetracycline chloride |
| CN111393319B (en) * | 2020-04-24 | 2023-03-28 | 山东国邦药业有限公司 | Preparation method of oxytetracycline chloride |
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 |
| CA949066A (en) | 1974-06-11 |
| IE36677L (en) | 1972-06-28 |
| NL7117996A (en) | 1972-06-30 |
| IL38383A (en) | 1974-12-31 |
| IE36677B1 (en) | 1977-02-02 |
| DK139674B (en) | 1979-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 414F | Notice of opposition given (sect. 14/1949) | ||
| 49R | Reference inserted (sect. 9/1949) | ||
| 414A | Case decided by the comptroller ** specification amended (sect. 14/1949) | ||
| SPA | Amended specification published | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |