GB1360998A - Recovery of doxycycline and products thereof - Google Patents
Recovery of doxycycline and products thereofInfo
- Publication number
- GB1360998A GB1360998A GB3012171A GB3012171A GB1360998A GB 1360998 A GB1360998 A GB 1360998A GB 3012171 A GB3012171 A GB 3012171A GB 3012171 A GB3012171 A GB 3012171A GB 1360998 A GB1360998 A GB 1360998A
- Authority
- GB
- United Kingdom
- Prior art keywords
- deoxytetracyclines
- deoxy
- reaction mixture
- acid
- june
- 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
- 229960003722 doxycycline Drugs 0.000 title 1
- XQTWDDCIUJNLTR-CVHRZJFOSA-N doxycycline monohydrate Chemical compound O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O XQTWDDCIUJNLTR-CVHRZJFOSA-N 0.000 title 1
- 238000011084 recovery Methods 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 239000011541 reaction mixture Substances 0.000 abstract 3
- 239000012535 impurity Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004098 Tetracycline Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 159000000007 calcium salts Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 abstract 1
- 239000007857 degradation product Substances 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 235000019364 tetracycline Nutrition 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 0.000 abstract 1
- 229940040944 tetracyclines Drugs 0.000 abstract 1
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
1360998 Purification of α-6-deoxytetracyclines I VILLAX 28 June 1971 [3 July 1970 10 Sept 1970 9 June 1971] 30121/71 Heading C2A A process for the purification of α-6-deoxytetracyclines from a reaction mixture containing, besides α-6-deoxytetracyclines, reaction byproducts, degradation products and the # isomer as impurities, is characterized in that the crude reaction mixture is acidified with a concentrated aqueous solution of a strong organic or inorganic acid, then heated up to a temperature of 60-90‹ C. until the impurities are further degraded, the reaction mixture is cooled and the α-6-deoxytetracyclines are recovered by precipitation as a water-insoluble derivative and subsequent formation of the free base, the hydrochloride or the calcium salt. Suitable tetracyclines which may be purified by this method include α - 6 - deoxytetracycline, α - 6 - deoxy- 5 - hydroxytetiacycline, α - 6 - deoxy - 7- chlorotetracycline and α-6-deoxy-7-chloro-5- hydoxytetracycline. Suitable acids are methanesulphonic acid, sulphuric acid and hydrochloric acid in concentrations between 2 and 18 per cent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT5410970 | 1970-07-03 | ||
| PT5410971 | 1971-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1360998A true GB1360998A (en) | 1974-07-24 |
Family
ID=26653423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3012171A Expired GB1360998A (en) | 1970-07-03 | 1971-06-28 | Recovery of doxycycline and products thereof |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5632303B1 (en) |
| AT (1) | AT318803B (en) |
| CA (1) | CA945546A (en) |
| CH (1) | CH588445A5 (en) |
| DE (1) | DE2131945B2 (en) |
| ES (1) | ES392575A1 (en) |
| FR (1) | FR2148660A5 (en) |
| GB (1) | GB1360998A (en) |
| HK (1) | HK78879A (en) |
| NL (1) | NL7109000A (en) |
| ZA (1) | ZA714323B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005011707A1 (en) * | 2003-07-25 | 2005-02-10 | Warner Chilcott Company, Inc. | A doxycycline metal complex in a solid dosage form |
| CN107162924A (en) * | 2017-05-16 | 2017-09-15 | 扬州联博药业有限公司 | A kind of method that Doxycycline is reclaimed in the refinement mother liquor from Doxycycline Hyclate |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3795707A (en) * | 1970-12-28 | 1974-03-05 | Rachelle Labor Italia Spa | Manufacture of alpha-6-deoxytetracyclines |
-
1971
- 1971-06-25 CA CA116,691A patent/CA945546A/en not_active Expired
- 1971-06-26 DE DE19712131945 patent/DE2131945B2/en not_active Withdrawn
- 1971-06-28 GB GB3012171A patent/GB1360998A/en not_active Expired
- 1971-06-29 NL NL7109000A patent/NL7109000A/xx not_active Application Discontinuation
- 1971-06-30 CH CH961271A patent/CH588445A5/xx not_active IP Right Cessation
- 1971-07-01 ZA ZA714323A patent/ZA714323B/en unknown
- 1971-07-02 FR FR7124329A patent/FR2148660A5/fr not_active Expired
- 1971-07-02 JP JP7148699A patent/JPS5632303B1/ja active Pending
- 1971-07-05 AT AT580271A patent/AT318803B/en not_active IP Right Cessation
-
1972
- 1972-06-23 ES ES392575A patent/ES392575A1/en not_active Expired
-
1979
- 1979-11-15 HK HK788/79A patent/HK78879A/en unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005011707A1 (en) * | 2003-07-25 | 2005-02-10 | Warner Chilcott Company, Inc. | A doxycycline metal complex in a solid dosage form |
| US7485319B2 (en) | 2003-07-25 | 2009-02-03 | Warner Chilcott Company, Inc. | Doxycycline metal complex in a solid dosage form |
| AU2004261143B2 (en) * | 2003-07-25 | 2009-11-05 | Allergan Pharmaceuticals International Limited | A doxycycline metal complex in a solid dosage form |
| US8415331B2 (en) | 2003-07-25 | 2013-04-09 | Warner Chilcott Company, Llc | Doxycycline metal complex in a solid dosage form |
| CN103040773A (en) * | 2003-07-25 | 2013-04-17 | 沃纳奇尔科特有限责任公司 | Doxycycline metal complex in a solid dosage form |
| CN107162924A (en) * | 2017-05-16 | 2017-09-15 | 扬州联博药业有限公司 | A kind of method that Doxycycline is reclaimed in the refinement mother liquor from Doxycycline Hyclate |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2131945A1 (en) | 1972-01-20 |
| CH588445A5 (en) | 1977-06-15 |
| NL7109000A (en) | 1972-01-05 |
| DE2131945B2 (en) | 1973-06-07 |
| ES392575A1 (en) | 1973-01-01 |
| ZA714323B (en) | 1972-03-29 |
| JPS5632303B1 (en) | 1981-07-27 |
| AT318803B (en) | 1974-10-25 |
| HK78879A (en) | 1979-11-23 |
| CA945546A (en) | 1974-04-16 |
| FR2148660A5 (en) | 1973-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |