FR2379536A1 - 9- (2,6-DIHALOGENOBENZYL) PURE ADENINES USEFUL AS MEDICINAL PRODUCTS, PROCESS FOR THEIR PREPARATION AND PURIFICATION - Google Patents
9- (2,6-DIHALOGENOBENZYL) PURE ADENINES USEFUL AS MEDICINAL PRODUCTS, PROCESS FOR THEIR PREPARATION AND PURIFICATIONInfo
- Publication number
- FR2379536A1 FR2379536A1 FR7803115A FR7803115A FR2379536A1 FR 2379536 A1 FR2379536 A1 FR 2379536A1 FR 7803115 A FR7803115 A FR 7803115A FR 7803115 A FR7803115 A FR 7803115A FR 2379536 A1 FR2379536 A1 FR 2379536A1
- Authority
- FR
- France
- Prior art keywords
- isomer
- adenines
- purification
- useful
- preparation
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La présente invention concerne des 9-(2,6-dihalogénobenzyl) adénines sensiblement exemptes du 3-isomère ainsi que leur préparation et leur purification. L'un des procédés de préparation de ces composés consiste à alcoyler un sel d'adénine avec des halogénures de 2,6-dihalogénobenzyle dans un système à deux phases en présence d'un catalyseur de transfert de phase et à traiter ensuite le mélange résultant d'isomères de position, contenant principalement le 9-isomère désiré contaminé par des quantites importantes du 3-isomère mutagène, en désalcoylant selectivement le 3-isomère avec de l'acide sulfurique en présence d'un piège à ions carbénium pour obtenir le 9-isomère sensiblement exempt du 3-isomère. Les adénines ainsi obtenues sont utiles comme agents de traitement et de prévention de la coccidiose chez la volaille.The present invention relates to substantially 3-isomer-free 9- (2,6-dihalobenzyl) adenines and their preparation and purification. One of the methods of preparing these compounds is to alkylate an adenine salt with 2,6-dihalobenzyl halides in a two-phase system in the presence of a phase transfer catalyst and then process the resulting mixture. of positional isomers, mainly containing the desired 9-isomer contaminated with significant amounts of the mutagenic 3-isomer, by selectively dealkylating the 3-isomer with sulfuric acid in the presence of a carbenium ion trap to obtain 9 -isomer substantially free from the 3-isomer. The adenines thus obtained are useful as agents for the treatment and prevention of coccidiosis in poultry.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/766,326 US4100159A (en) | 1977-02-07 | 1977-02-07 | Process for preparation of 9-(2,6-dihalobenzyl)adenines |
| US05/768,235 US4098787A (en) | 1977-02-14 | 1977-02-14 | Process for preparation of 9-(dihalobenzyl) adenines |
| US84391977A | 1977-10-20 | 1977-10-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2379536A1 true FR2379536A1 (en) | 1978-09-01 |
| FR2379536B1 FR2379536B1 (en) | 1983-10-07 |
Family
ID=27419624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7803115A Granted FR2379536A1 (en) | 1977-02-07 | 1978-02-03 | 9- (2,6-DIHALOGENOBENZYL) PURE ADENINES USEFUL AS MEDICINAL PRODUCTS, PROCESS FOR THEIR PREPARATION AND PURIFICATION |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS53124294A (en) |
| AR (1) | AR225000A1 (en) |
| AT (1) | AT361008B (en) |
| CH (1) | CH636614A5 (en) |
| DD (1) | DD136744A5 (en) |
| DE (1) | DE2804723A1 (en) |
| DK (1) | DK36078A (en) |
| EG (1) | EG13333A (en) |
| ES (1) | ES466647A1 (en) |
| FI (1) | FI64596C (en) |
| FR (1) | FR2379536A1 (en) |
| GB (1) | GB1586537A (en) |
| GR (1) | GR64457B (en) |
| IE (1) | IE46399B1 (en) |
| IL (1) | IL53922A (en) |
| IT (1) | IT1105174B (en) |
| NL (1) | NL7800896A (en) |
| NO (1) | NO148374C (en) |
| NZ (1) | NZ186357A (en) |
| PL (1) | PL118655B1 (en) |
| PT (1) | PT67606B (en) |
| SE (1) | SE440355B (en) |
| YU (1) | YU27778A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4900826A (en) * | 1981-09-24 | 1990-02-13 | Kohjin Co., Ltd. | Process for preparing N6,9-disubstituted adenine |
| EP0411467A3 (en) * | 1989-08-01 | 1992-03-04 | Lonza Ag | Process for the preparation of pure adenin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846426A (en) * | 1971-03-03 | 1974-11-05 | Int Minerals & Chem Corp | 6-amino-9-(substituted benzyl) purines and their n{11 oxides |
-
1978
- 1978-01-23 FI FI780200A patent/FI64596C/en not_active IP Right Cessation
- 1978-01-25 DK DK36078A patent/DK36078A/en not_active Application Discontinuation
- 1978-01-25 NL NL7800896A patent/NL7800896A/en not_active Application Discontinuation
- 1978-01-26 SE SE7800977A patent/SE440355B/en not_active IP Right Cessation
- 1978-01-26 NO NO780284A patent/NO148374C/en unknown
- 1978-01-30 IL IL53922A patent/IL53922A/en unknown
- 1978-01-31 NZ NZ186357A patent/NZ186357A/en unknown
- 1978-01-31 AR AR270912A patent/AR225000A1/en active
- 1978-02-02 GR GR55327A patent/GR64457B/en unknown
- 1978-02-02 PT PT67606A patent/PT67606B/en unknown
- 1978-02-03 DD DD78203555A patent/DD136744A5/en unknown
- 1978-02-03 CH CH124478A patent/CH636614A5/en not_active IP Right Cessation
- 1978-02-03 ES ES466647A patent/ES466647A1/en not_active Expired
- 1978-02-03 DE DE19782804723 patent/DE2804723A1/en active Granted
- 1978-02-03 FR FR7803115A patent/FR2379536A1/en active Granted
- 1978-02-04 PL PL1978204447A patent/PL118655B1/en unknown
- 1978-02-06 IT IT47941/78A patent/IT1105174B/en active
- 1978-02-06 EG EG76/78A patent/EG13333A/en active
- 1978-02-06 IE IE253/78A patent/IE46399B1/en unknown
- 1978-02-06 YU YU00277/78A patent/YU27778A/en unknown
- 1978-02-06 GB GB4691/78A patent/GB1586537A/en not_active Expired
- 1978-02-06 AT AT79778A patent/AT361008B/en not_active IP Right Cessation
- 1978-02-07 JP JP1290178A patent/JPS53124294A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT67606B (en) | 1980-03-03 |
| IL53922A0 (en) | 1978-04-30 |
| GB1586537A (en) | 1981-03-18 |
| IE46399B1 (en) | 1983-06-01 |
| IT7847941A0 (en) | 1978-02-06 |
| ATA79778A (en) | 1980-07-15 |
| DK36078A (en) | 1978-08-08 |
| FI64596B (en) | 1983-08-31 |
| DD136744A5 (en) | 1979-07-25 |
| PL118655B1 (en) | 1981-10-31 |
| FI64596C (en) | 1983-12-12 |
| GR64457B (en) | 1980-03-24 |
| IE780253L (en) | 1978-08-07 |
| DE2804723A1 (en) | 1978-08-10 |
| NO148374B (en) | 1983-06-20 |
| YU27778A (en) | 1983-12-31 |
| PL204447A1 (en) | 1979-06-04 |
| FI780200A (en) | 1978-08-08 |
| AR225000A1 (en) | 1982-02-15 |
| EG13333A (en) | 1981-06-30 |
| SE7800977L (en) | 1978-08-08 |
| SE440355B (en) | 1985-07-29 |
| NO780284L (en) | 1978-08-08 |
| ES466647A1 (en) | 1980-12-16 |
| PT67606A (en) | 1978-03-01 |
| IL53922A (en) | 1981-02-27 |
| JPS53124294A (en) | 1978-10-30 |
| CH636614A5 (en) | 1983-06-15 |
| FR2379536B1 (en) | 1983-10-07 |
| DE2804723C2 (en) | 1990-11-29 |
| IT1105174B (en) | 1985-10-28 |
| AT361008B (en) | 1981-02-10 |
| NL7800896A (en) | 1978-08-09 |
| NO148374C (en) | 1983-09-28 |
| NZ186357A (en) | 1981-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |