IE36677B1 - Manufacture of 6-methylenetetracyclines - Google Patents

Manufacture of 6-methylenetetracyclines

Info

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
Application number
IE1381/71A
Other versions
IE36677L (en
Original Assignee
Rachelle Lab Italia Spa
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rachelle Lab Italia Spa filed Critical Rachelle Lab Italia Spa
Publication of IE36677L publication Critical patent/IE36677L/en
Publication of IE36677B1 publication Critical patent/IE36677B1/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic 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]
IE1381/71A 1970-12-28 1971-11-01 Manufacture of 6-methylenetetracyclines IE36677B1 (en)

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)

* Cited by examiner, † Cited by third party
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

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

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