WO2004110343A2 - 2-amino-9-(2-substituted ethyl)purines and preparing methods for 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]- 2- aminopurine using the same - Google Patents
2-amino-9-(2-substituted ethyl)purines and preparing methods for 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]- 2- aminopurine using the same Download PDFInfo
- Publication number
- WO2004110343A2 WO2004110343A2 PCT/KR2004/001405 KR2004001405W WO2004110343A2 WO 2004110343 A2 WO2004110343 A2 WO 2004110343A2 KR 2004001405 W KR2004001405 W KR 2004001405W WO 2004110343 A2 WO2004110343 A2 WO 2004110343A2
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- WIPO (PCT)
- Prior art keywords
- formula
- compound
- amino
- purine
- following formula
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- 0 C[N]1(CCC(CO)CO)c(N=C)c(/C=N\C/C=N\C)nc1 Chemical compound C[N]1(CCC(CO)CO)c(N=C)c(/C=N\C/C=N\C)nc1 0.000 description 4
- XCPHJACVZTYUJN-UHFFFAOYSA-N Nc(nc1)nc2c1nc[n]2CCO Chemical compound Nc(nc1)nc2c1nc[n]2CCO XCPHJACVZTYUJN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
Definitions
- the present invention relates to a new compound of 2-amino-9-(2-substituted ethyl)purine and an effective method for preparing
- the present invention relates to an effective method for preparing famciclovir of the following formula (I) using 2-amino-9-(2-substituted ethyl)purine of the following formula (IF), by which famciclovir can be prepared in high selectivity and high process efficiency under relatively mild reaction conditions:
- R represents hydroxy, halogen, mesyloxy or tosyloxy.
- reaction scheme (1) has a severe problem in that a palladium catalyst, which is highly explosive, must be used in the preparation of the final desired compound of formula (1) from the compound of formula (X). Thus, this method has low process efficiency which makes its industrial application unsuitable.
- US Patent No. 5,971,041 discloses a method for preparing 9-[4-acetoxy-3-(aectoxymethyl)but-l-yl]-2-aminopurine of the following formula (1) as shown in the following reaction scheme (4), in which (N-(2-amino-4,6- dichloro- 5-pyrimidinyl)formamide of the following formula (XV) is reacted with 2-Acetoxymethyl-4-aminobut-l-yl-acetate of the following formula (XVI) to give a compound of the following formula (XVII), which is then converted into 9-[4-acetoxy-3-(acetoxymethyl)but-l-yl]-2-amino-6-chloropurine using triethy- lorthoformate of the following formula (XVIII), which is, in turn, reduced into the compound of formula (I) using palladium as a reduction catalyst:
- a first object of the present invention is to provide a new compound which can be effectively used in the preparation of famciclovir, an antiviral purine derivative drug.
- a second object of the present invention is to provide a method for the preparation of famciclovir, which has high selectivity leading to high process efficiency.
- a third object of the present invention is to provide a method for the preparation of famciclovir, which allows the utilization of relatively mild reaction conditions and thus has high process efficiency.
- the present invention relates to a new compound of 2-amino-9-(2-substituted ethyl)purine of the following formula (H'), and a method for effectively preparing 9-[4-acetoxy-3-(acetoxymethyl)but-l-yl]-2-aminopurine (called 'famciclovir') of the following formula (I) using the same, in which the famciclovir is a purine derivative drug with effective antiviral activity (see European Patent No. 141,927): [33] (Formula I)
- R is a hydroxy, halogen, mesyloxy or tosyloxy group.
- 2-amino-9-(2-substituted ethyl)purine of formula (IF) the compound of formula (IF) shows 100% selectivity, so that 7-[4-acetoxy-3-(acetoxymethyl)but-l-yl] - 2-aminopurine of the following formula (XXIII), which is an isomer of the famciclovir represented by formula (I) and has no pharmacological activity, is not produced as a byproduct in a preparation process of famciclovir.
- the desired compound, famciclovir can be prepared in a high selectivity of 100%.
- the famciclovir of formula (I) as the desired compound can be prepared in 100% selectivity by a preparation method which is generally described just below.
- this preparation method comprises: halogenating 2-amino-9-(2- hydroxyethyl)purine of the following formula (II) to give 2-amino-9-(2-halogenoethyl)purine of the following formula (III), subjecting the compound of formula (III) to substitution reaction with diethylmalonate of the following formula (IV) to give 2-amino-9-(ethyl 2- carboethoxybutanoate- 4-yl)purine of the following formula (V), reducing the compound of formula (V) to give 2-amino-9-[4-hydroxy-3-(hydroxymethyl)but-l-yl]purine of the following formula (VI), and acetylating the compound of formula (VI):
- the compounds of formulas II and III in the above general description about the inventive preparation method are core materials in the inventive preparation methods.
- the compound of formula (II) contains no a mino-7-(2-hydroxyethyl)purine) of the following formula (VII), which is its isomer, and thus, it has a high selectivity of 100%.
- the compounds of formula (H') may also be compounds having various sub- stituents, such as 2-amino-9-(2-mesyloxyethyl)purine of the following formula (XXVI) or 2-amino-9-(2-tosyloxyethyl)purine of the following formula (XXVII), in addition to 2-amino-9-(2-hydroxyethyl)purine of formula (II).
- Any of such compounds is highly useful as an intermediate for the preparation of a purine derivative drug, such as famciclovir with antiviral and antibacterial activities.
- the halogen in 2-amino-9-(2-halogenoethyl)purine of formula (III) is not specifically limited, but is most preferably bromine in view of the following advantages: (1) the preparation of the compound (III) is easy, (2) a reaction process is very efficient, and (3) a brominating agent results in a very high yield of more than 90%.
- 2-amino-9-(2-bromoethyl)purine having a bromine substituent is represented by the following formula (III-l):
- 2-amino-9-(2-hydroxyethyl)purine of formula (II) is reacted with a halogenating agent, such as c arbon tetrachloride, sodium iodide, potassium iodide, triphenylphosphine dibromide, carbon tetrabromide, or N- bromosuccinimide, in a polar or nonpolar organic solvent, at a temperature of about 0-100 ° C, and preferably about 20-40 ° C, for about 2-10 hours, and preferably about 3-5 hours, to give 2-amino-9-(2-halogenoethyl)purine of formula (III).
- a halogenating agent such as c arbon tetrachloride, sodium iodide, potassium iodide, triphenylphosphine dibromide, carbon tetrabromide, or N- bromosuccinimide
- the compound of formula (III) is then reacted with diethylmalonate of formula (IV) in the presence of a base, such as potassium carbonate, sodium carbonate, sodium methoxide or sodium ethoxide, in a polar organic solvent, at a temperature of about 0-100 ° C, and preferably 40-60 ° C, for about 2-10 hours, and preferably about 3-5 hours, to give 2-amino-9-(ethyl 2-carboethoxybutanoate-4-yl)purine of formula (V).
- a base such as potassium carbonate, sodium carbonate, sodium methoxide or sodium ethoxide
- the compound of formula (V) after separation or without separation, is reacted with a reducing agent, such as sodium borohydride or lithium aluminum hydride, in a polar or nonpolar organic solvent, at a temperature of about 0-100 ° C, and preferably about 40-60 ° C, for about 2-10 hours, and preferably about 3-5 hours, to give 2-amino-9-[4-hydroxy-3-(hydroxymethyl)but-l-yl]purines of formula (VI).
- a reducing agent such as sodium borohydride or lithium aluminum hydride
- the compound of formula (VI) is reacted with acetic acid anhydride in a nonpolar organic solvent at a temperature of about 0-100 ° C, and preferably about 20-40 ° C, for about 2-10 hours, and preferably about 3-5 hours, to produce the final desired compound (famciclovir) of formula (I).
- Preferred examples of the polar organic solvent which is used in the inventive preparation method include N,N-dimethylformamide, dimethylsulfoxide, acetonitrile, pyridine, acetic acid, and lower alcohol solvents with 1 to 3 carbon atoms, such as methanol, ethanol or isopropanol, and a mixture thereof.
- Preferred examples of the nonpolar organic solvent include ethylether, tetrahydrofuran, toluene, benzene, 1,4-dioxane, chloroform, dichloromethane, and a mixture thereof.
- the compound of formula (H') which is used as a starting material in the inventive preparation method is a new material, and its preparation method will now be described in brief with reference to the following reaction scheme (7) by way of an example where the compound of formula (IF) is 2-amino-9-(2-hydroxyethyl)purine.
- 2-amino-4-(2-hydroxyethylamino)-5-nitropyrimidine is reacted with a reducing agent, such as Raney-nickel or iron powder, in a polar organic solvent at a temperature of about 0-100 ° C, and preferably about 30- 5O 0 C , for about 1-10 hours, and preferably about 2-5 hours, to give 2,5-diamino-4-(2-hydroxyethylamino)pyrimidine of formula (XXV).
- a reducing agent such as Raney-nickel or iron powder
- the compound of formula (XXV) is allowed to react immediately without separation, in triethylorthoformate of formula (XVIII) at a temperature of about 50-150 ° C, and preferably about 70-90 ° C, for about 5-15 hours, and preferably about 8-10 hours, to give 2-amino-9-(2-hydroxyethyl)purine.
- the compound of formula (XXIX) is then reacted with ethanolamine of formula (XXX) in a polar organic solvent at a temperature of about 0-100 ° C, and preferably about 10-20 ° C, for about 10-30 hours, and preferably about 15-20, to give 2-chloro-4-(2-hydroxyethylamino)-5-nitropyrimidine of formula (XXXI).
- IR n (cm "1 ): 3410, 3335, 3205, 2945, 1627, 1577 max
- IR n (cm "1 ): 3432, 3336, 3215, 3007, 2964, 1638 max
- the remaining concentrate was added to 300 ml of t-butanol and then warmed to 60 ° C, followed by the addition of 21.06 g (0.61 mole) of sodium borohydride. To the resulting mixture, 30 ml of methanol was added slowly, followed by stirring for five hours. After completion of the reaction, the reaction product was cooled to room temperature, neutralized with diluted hydrochloric acid, and then concentrated. The remaining concentrate was added to 100 ml of methanol and then stirred for two hours at room temperature, followed by filtration. The filtrate was concentrated under reduced pressure and crystallized from butanol, thereby giving 13.05 g (55% yield) of light yellow-colored 2-amino-9-[4-hydroxy-3-(hydroxymethyl)but-l-yl] purine.
- IR n (cm "1 ): 3330, 3160, 1743, 1728, 1645, 1606 max
- the preparation method according to the present invention allows famciclovir, a purine derivative drug with effective antiviral activity, to be prepared in a high selectivity of 100% in a pure form by using the inventive new compound of 2-amino-9-(2-substituted ethyl)purine.
- the inventive method allows the utilization of relatively mild reaction conditions, and thus, has high industrial process efficiency.
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/554,676 US7456282B2 (en) | 2003-06-13 | 2004-06-12 | 2-amino-9-(2-substituted ethyl)purines and preparing methods for 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine using the same |
DE602004026180T DE602004026180D1 (en) | 2003-06-13 | 2004-06-12 | PREPARATION OF 9-A4-ACETOXY-3- (ACETOXYMETHYL) BUT-1-YLÜ-2-AMINOPURINE USING A COMPOUND OF 2-AMINO-9- (2-SUBSTITUTED ETHYL) PURINE |
EP04773919A EP1636231B1 (en) | 2003-06-13 | 2004-06-12 | Methods for preparing 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine using a compound of 2-amino-9-(2-substituted ethyl)purines |
AT04773919T ATE461931T1 (en) | 2003-06-13 | 2004-06-12 | PRODUCTION METHOD FOR 9-Ä4-ACETOXY-3-(ACETOXYMETHYL)BUT-1-YLU-2-AMINOPURINE USING A COMPOUND OF 2-AMINO-9-(2-SUBSTITUTED ETHYL)PURINES |
JP2006500699A JP2006523614A (en) | 2003-06-13 | 2004-06-12 | 2-Amino-9- (2-substituted ethyl) purine and method for producing 9- [4-acetoxy-3- (acetoxymethyl) butyyl] -2-aminopurine using the same |
AU2004246958A AU2004246958B2 (en) | 2003-06-13 | 2004-06-12 | 2-amino-9-(2-substituted ethyl)purines and preparing methods for 9-(4-acetoxy-3-(acetoxymethyl)but-1-yl)- 2- aminopurine using the same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2003-0038417 | 2003-06-13 | ||
KR1020030038417A KR100573860B1 (en) | 2003-06-13 | 2003-06-13 | Preparing methods for 9-[4-acetoxy-3-acetoxymethylbut-1-yl]-2-aminopurine using 2-amino-9-2-substituted ethylpurines |
Publications (2)
Publication Number | Publication Date |
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WO2004110343A2 true WO2004110343A2 (en) | 2004-12-23 |
WO2004110343A3 WO2004110343A3 (en) | 2005-09-01 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/KR2004/001405 WO2004110343A2 (en) | 2003-06-13 | 2004-06-12 | 2-amino-9-(2-substituted ethyl)purines and preparing methods for 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]- 2- aminopurine using the same |
Country Status (9)
Country | Link |
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US (1) | US7456282B2 (en) |
EP (1) | EP1636231B1 (en) |
JP (1) | JP2006523614A (en) |
KR (1) | KR100573860B1 (en) |
CN (1) | CN100455583C (en) |
AT (1) | ATE461931T1 (en) |
AU (1) | AU2004246958B2 (en) |
DE (1) | DE602004026180D1 (en) |
WO (1) | WO2004110343A2 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006123175A1 (en) * | 2005-05-20 | 2006-11-23 | Arrow International Limited | Preparation of famciclovir and other purine derivatives |
WO2008072074A1 (en) * | 2006-12-11 | 2008-06-19 | Aurobindo Pharma Limited | An improved process for the preparation of purine derivative |
CN106749254A (en) * | 2017-01-10 | 2017-05-31 | 青岛科技大学 | A kind of 6 adenine phosphate ethylnaphthalene acetate compounds and its purposes as plant growth regulator |
CN109456329A (en) * | 2018-11-19 | 2019-03-12 | 威海迪素制药有限公司 | A kind of preparation method of famciclovir |
WO2022090101A1 (en) | 2020-10-26 | 2022-05-05 | Boehringer Ingelheim International Gmbh | Process for synthesis of 2,4-dichloro-5-aminopyrimidine |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040097528A1 (en) * | 2002-08-26 | 2004-05-20 | Ben-Zion Dolitzky | Crystalline solid famciclovir forms I, II, III and preparation thereof |
TW200510415A (en) * | 2003-04-30 | 2005-03-16 | Teva Pharma | Process for the preparation of famciclovir |
KR100573861B1 (en) * | 2003-07-18 | 2006-04-25 | 경동제약 주식회사 | Preparing Methods for 2-Amino-9-2-halogenoethylpurine and 2-Amino-6,8-dichloro-9-2-hydroxyethylpurine as an Intermediate thereof |
KR100618232B1 (en) * | 2004-09-22 | 2006-09-04 | 한미약품 주식회사 | Method for the preparation of famciclovir |
EP2170840A1 (en) * | 2007-06-21 | 2010-04-07 | Aurobindo Pharma Ltd | An improved process for preparing purine derivative |
CN101555249B (en) * | 2008-04-08 | 2011-05-11 | 浙江海正药业股份有限公司 | Method for synthesizing famciclovir |
CN102924455A (en) * | 2011-08-11 | 2013-02-13 | 重庆圣华曦药业股份有限公司 | Synthetic method of famciclovir intermediate |
CN108314685B (en) * | 2018-03-16 | 2020-08-25 | 上药康丽(常州)药业有限公司 | Preparation method of 2-amino-6-chloro-9- (4-acetoxyl-3-acetoxymethyl butyl) purine |
Citations (5)
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EP0420559A2 (en) * | 1989-09-28 | 1991-04-03 | Beecham Group p.l.c. | Process for the preparation of purine compounds |
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US5917041A (en) * | 1994-02-04 | 1999-06-29 | Glaxo Wellcome Inc. | Chloropyrimidine intermediates |
-
2003
- 2003-06-13 KR KR1020030038417A patent/KR100573860B1/en active IP Right Grant
-
2004
- 2004-06-12 CN CNB2004800132912A patent/CN100455583C/en not_active Expired - Lifetime
- 2004-06-12 DE DE602004026180T patent/DE602004026180D1/en not_active Expired - Fee Related
- 2004-06-12 EP EP04773919A patent/EP1636231B1/en not_active Expired - Lifetime
- 2004-06-12 AU AU2004246958A patent/AU2004246958B2/en not_active Ceased
- 2004-06-12 AT AT04773919T patent/ATE461931T1/en not_active IP Right Cessation
- 2004-06-12 JP JP2006500699A patent/JP2006523614A/en active Pending
- 2004-06-12 WO PCT/KR2004/001405 patent/WO2004110343A2/en active Application Filing
- 2004-06-12 US US10/554,676 patent/US7456282B2/en not_active Expired - Fee Related
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US20010004668A1 (en) * | 1983-08-18 | 2001-06-21 | Beecham Group Plc | Process for the preparation of purine derivatives |
US5684153A (en) * | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
US5138057A (en) * | 1988-09-21 | 1992-08-11 | Beecham Group P.L.C. | Chemical process for the preparation of purine derivatives |
EP0420559A2 (en) * | 1989-09-28 | 1991-04-03 | Beecham Group p.l.c. | Process for the preparation of purine compounds |
WO1994007892A1 (en) * | 1992-09-30 | 1994-04-14 | Smithkline Beecham Plc | Process for the preparation of 2-amino-6-chloropurine |
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Non-Patent Citations (1)
Title |
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CLAYETTE P. ET AL: 'Anti-VIH activities of novel nucleoside analogues: acyclic and tricyclic base nucleosides.' ANTIVIRAL CHEMISTRY & CHEMOTHERAPY. vol. 2, no. 6, 1991, pages 329 - 336, XP001237245 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006123175A1 (en) * | 2005-05-20 | 2006-11-23 | Arrow International Limited | Preparation of famciclovir and other purine derivatives |
US7601835B2 (en) | 2005-05-20 | 2009-10-13 | Arrow International Limited | Preparation of famciclovir and other purine derivatives |
AU2006248745B2 (en) * | 2005-05-20 | 2011-06-23 | Arrow International Limited | Preparation of famciclovir and other purine derivatives |
CN101233134B (en) * | 2005-05-20 | 2013-01-23 | 箭锋国际有限公司 | Preparation of famciclovir and other purine derivatives |
WO2008072074A1 (en) * | 2006-12-11 | 2008-06-19 | Aurobindo Pharma Limited | An improved process for the preparation of purine derivative |
CN106749254A (en) * | 2017-01-10 | 2017-05-31 | 青岛科技大学 | A kind of 6 adenine phosphate ethylnaphthalene acetate compounds and its purposes as plant growth regulator |
CN106749254B (en) * | 2017-01-10 | 2018-05-25 | 青岛科技大学 | A kind of adenine ethylnaphthalene acetate compounds and its purposes as plant growth regulator |
CN109456329A (en) * | 2018-11-19 | 2019-03-12 | 威海迪素制药有限公司 | A kind of preparation method of famciclovir |
CN109456329B (en) * | 2018-11-19 | 2021-03-09 | 迪嘉药业集团有限公司 | Preparation method of famciclovir |
WO2022090101A1 (en) | 2020-10-26 | 2022-05-05 | Boehringer Ingelheim International Gmbh | Process for synthesis of 2,4-dichloro-5-aminopyrimidine |
Also Published As
Publication number | Publication date |
---|---|
KR100573860B1 (en) | 2006-04-25 |
CN1791602A (en) | 2006-06-21 |
US20060258862A1 (en) | 2006-11-16 |
EP1636231B1 (en) | 2010-03-24 |
US7456282B2 (en) | 2008-11-25 |
WO2004110343A3 (en) | 2005-09-01 |
KR20040107812A (en) | 2004-12-23 |
EP1636231A2 (en) | 2006-03-22 |
JP2006523614A (en) | 2006-10-19 |
AU2004246958B2 (en) | 2010-09-16 |
AU2004246958A1 (en) | 2004-12-23 |
ATE461931T1 (en) | 2010-04-15 |
DE602004026180D1 (en) | 2010-05-06 |
CN100455583C (en) | 2009-01-28 |
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