JP2008546703A5 - - Google Patents
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- Publication number
- JP2008546703A5 JP2008546703A5 JP2008517073A JP2008517073A JP2008546703A5 JP 2008546703 A5 JP2008546703 A5 JP 2008546703A5 JP 2008517073 A JP2008517073 A JP 2008517073A JP 2008517073 A JP2008517073 A JP 2008517073A JP 2008546703 A5 JP2008546703 A5 JP 2008546703A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylamino
- contacting
- hydrogen
- amino
- formula
- 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
- 150000001875 compounds Chemical class 0.000 claims description 27
- -1 6- (azolyl) -substituted purines Chemical class 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 239000001257 hydrogen Substances 0.000 claims 32
- 125000003282 alkyl amino group Chemical group 0.000 claims 31
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000004442 acylamino group Chemical group 0.000 claims 17
- 239000002212 purine nucleoside Substances 0.000 claims 17
- 125000004414 alkyl thio group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 239000002798 polar solvent Substances 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 229910021529 ammonia Inorganic materials 0.000 claims 9
- MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- 230000002152 alkylating effect Effects 0.000 claims 6
- 125000003943 azolyl group Chemical group 0.000 claims 6
- 229960002436 cladribine Drugs 0.000 claims 6
- 230000004913 activation Effects 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 230000001279 glycosylating effect Effects 0.000 claims 4
- 239000002777 nucleoside Substances 0.000 claims 4
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 4
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 3
- 125000003147 glycosyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims 2
- ZPSIVTRVNOXGMN-UHFFFAOYSA-N 6-(1h-pyrrol-2-yl)-7h-purine Chemical compound C1=CNC(C=2C=3NC=NC=3N=CN=2)=C1 ZPSIVTRVNOXGMN-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 235000011962 puddings Nutrition 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- XRPXPIBYTXETSJ-UHFFFAOYSA-N 6-imidazol-1-yl-7h-purine Chemical compound C1=NC=CN1C1=NC=NC2=C1NC=N2 XRPXPIBYTXETSJ-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- 150000003212 purines Chemical class 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 description 3
- 125000006241 alcohol protecting group Chemical group 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000004996 haloaryloxy group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69030705P | 2005-06-14 | 2005-06-14 | |
| US60/690,307 | 2005-06-14 | ||
| PCT/US2006/023193 WO2006138396A2 (en) | 2005-06-14 | 2006-06-14 | Methods for selective n-9 glycosylation of purines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008546703A JP2008546703A (ja) | 2008-12-25 |
| JP2008546703A5 true JP2008546703A5 (enExample) | 2011-12-01 |
| JP4966969B2 JP4966969B2 (ja) | 2012-07-04 |
Family
ID=37571119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008517073A Active JP4966969B2 (ja) | 2005-06-14 | 2006-06-14 | プリンの選択的ｎ−９グリコシル化のための方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7855285B2 (enExample) |
| EP (1) | EP1895841A4 (enExample) |
| JP (1) | JP4966969B2 (enExample) |
| CN (1) | CN101257797B (enExample) |
| AU (1) | AU2006259431B2 (enExample) |
| CA (1) | CA2653247C (enExample) |
| IL (1) | IL188123A (enExample) |
| WO (1) | WO2006138396A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8232387B2 (en) * | 2009-08-18 | 2012-07-31 | Scinopharm Taiwan, Ltd. | Process for the preparation of cladribine |
| EP2343074A1 (en) | 2009-12-23 | 2011-07-13 | Merck Serono S.A. | Use of purine analogues for treating airway diseases |
| US20150376219A1 (en) * | 2014-06-30 | 2015-12-31 | Minghong Zhong | Selective Preparations of Purine Nucleosides and Nucleotides: Reagents and Methods |
| CN109928930A (zh) * | 2019-03-13 | 2019-06-25 | 宁夏倬昱新材料科技有限公司 | 一种2-丙基咪唑制备工艺 |
| CN116462719B (zh) * | 2023-04-28 | 2025-08-29 | 上海兆维科技发展有限公司 | α构型的脱氧核苷的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2709634A1 (de) | 1977-03-05 | 1978-09-07 | Basf Ag | Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| IL64501A (en) | 1980-12-22 | 1985-07-31 | Astra Laekemedel Ab | 9-substituted 4-hydroxybutyl guanine derivatives,their preparation and antiviral use |
| US4579849A (en) | 1984-04-06 | 1986-04-01 | Merck & Co., Inc. | N-alkylguanine acyclonucleosides as antiviral agents |
| US4760137A (en) | 1984-08-06 | 1988-07-26 | Brigham Young University | Method for the production of 2'-deoxyadenosine compounds |
| US4801710A (en) | 1984-10-26 | 1989-01-31 | Merck & Co., Inc. | Regioselective synthesis of 9-substituted purine acyclonucleoside derivatives |
| US5459255A (en) | 1990-01-11 | 1995-10-17 | Isis Pharmaceuticals, Inc. | N-2 substituted purines |
| JP3906488B2 (ja) | 1995-02-21 | 2007-04-18 | 味の素株式会社 | プリン誘導体の製造方法 |
| US5989569A (en) * | 1997-06-06 | 1999-11-23 | The Procter & Gamble Company | Delivery system for a tooth whitener using a permanently deformable strip of material |
| CZ9901996A3 (cs) | 1999-06-04 | 2001-01-17 | Ústav organické chemie a biochemie AV ČR | Nové 6-fenylpurinové 9-ß-D-ribonukleosidy s antineoplastickým účinkem, jejich použití k přípravě farmaceutických preparátů a farmaceutické přípravky, které je obsahují |
| MXPA02008075A (es) * | 2000-02-18 | 2005-06-06 | Southern Res Inst | Metodos para sintetizar 2-cloro -9-(2 -deoxi-2 -fluoro -beta- arabinofura-nosil)- 9h- purin- 6-amina. |
| US20030008841A1 (en) * | 2000-08-30 | 2003-01-09 | Rene Devos | Anti-HCV nucleoside derivatives |
| US6884880B2 (en) | 2002-08-21 | 2005-04-26 | Ash Stevens, Inc. | Process for the preparation of 9-β-anomeric nucleoside analogs |
-
2006
- 2006-06-14 JP JP2008517073A patent/JP4966969B2/ja active Active
- 2006-06-14 CA CA2653247A patent/CA2653247C/en active Active
- 2006-06-14 CN CN2006800297083A patent/CN101257797B/zh active Active
- 2006-06-14 AU AU2006259431A patent/AU2006259431B2/en active Active
- 2006-06-14 EP EP06784893A patent/EP1895841A4/en not_active Withdrawn
- 2006-06-14 WO PCT/US2006/023193 patent/WO2006138396A2/en not_active Ceased
- 2006-06-14 US US11/917,544 patent/US7855285B2/en active Active
-
2007
- 2007-12-13 IL IL188123A patent/IL188123A/en active IP Right Grant
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