JP2002510691A5 - - Google Patents
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- JP2002510691A5 JP2002510691A5 JP2000542324A JP2000542324A JP2002510691A5 JP 2002510691 A5 JP2002510691 A5 JP 2002510691A5 JP 2000542324 A JP2000542324 A JP 2000542324A JP 2000542324 A JP2000542324 A JP 2000542324A JP 2002510691 A5 JP2002510691 A5 JP 2002510691A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
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- 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.)
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- 150000001875 compounds Chemical class 0.000 description 21
- 238000000034 method Methods 0.000 description 14
- -1 cyclic acetal Chemical class 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 125000005104 aryl silyl group Chemical group 0.000 description 2
- GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 0 CC(*)*=C(*)*=C(C)[C@]1[C@](C)*C*1CC[C@@](C)C* Chemical compound CC(*)*=C(*)*=C(C)[C@]1[C@](C)*C*1CC[C@@](C)C* 0.000 description 1
- JNTOCHDNEULJHD-UHFFFAOYSA-N Penciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2 JNTOCHDNEULJHD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 229960004396 famciclovir Drugs 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-M phenyl carbonate Chemical compound [O-]C(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical group COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9807114.5A GB9807114D0 (en) | 1998-04-02 | 1998-04-02 | Novel process |
| GB9807114.5 | 1998-04-02 | ||
| PCT/EP1999/002308 WO1999051603A1 (en) | 1998-04-02 | 1999-03-30 | Process for the production of purine derivatives and intermediates therefor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002510691A JP2002510691A (ja) | 2002-04-09 |
| JP2002510691A5 true JP2002510691A5 (https=) | 2006-05-25 |
| JP4524040B2 JP4524040B2 (ja) | 2010-08-11 |
Family
ID=10829763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000542324A Expired - Fee Related JP4524040B2 (ja) | 1998-04-02 | 1999-03-30 | プリン誘導体の製法およびその中間体 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US6555685B1 (https=) |
| EP (1) | EP1068209B1 (https=) |
| JP (1) | JP4524040B2 (https=) |
| KR (1) | KR100701114B1 (https=) |
| CN (1) | CN1153769C (https=) |
| AT (1) | ATE304541T1 (https=) |
| AU (1) | AU3420099A (https=) |
| BR (1) | BR9908964A (https=) |
| CA (1) | CA2322583A1 (https=) |
| DE (1) | DE69927251T2 (https=) |
| DK (1) | DK1068209T3 (https=) |
| ES (1) | ES2247793T3 (https=) |
| GB (1) | GB9807114D0 (https=) |
| IL (1) | IL138288A (https=) |
| WO (1) | WO1999051603A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1288215B8 (en) | 2001-08-30 | 2005-04-06 | Ajinomoto Co., Inc. | Production method of famciclovir and production and crystallization method of intermediate therefor |
| EP1532151A2 (en) * | 2002-08-26 | 2005-05-25 | Teva Pharmaceutical Industries Limited | Crystalline solid famciclovir forms i, ii, iii and preparation thereof |
| EP1511750A1 (en) * | 2003-04-30 | 2005-03-09 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of famciclovir |
| EP1556383A1 (en) * | 2003-09-04 | 2005-07-27 | Teva Pharmaceutical Industries Ltd. | Process for preparing famciclovir |
| WO2005103025A1 (en) * | 2004-04-21 | 2005-11-03 | Novogen Research Pty Ltd | Isoflavene synthetic method and catalyst |
| GB2426247A (en) * | 2005-05-20 | 2006-11-22 | Arrow Int Ltd | Methods of preparing purine derivatives such as famciclovir |
| MX342459B (es) | 2010-08-27 | 2016-09-29 | Grünenthal Gmbh * | 2-oxo- y 2-tioxo-dihidroquinolin-3-carboxamidas sustituidas, como moduladores de kcnq2/3. |
| CA2805932A1 (en) | 2010-08-27 | 2012-03-01 | Gruenenthal Gmbh | Substituted 2-amino-quinoline-3-carboxamides as kcnq2/3 modulators |
| RU2595894C2 (ru) | 2010-08-27 | 2016-08-27 | Грюненталь Гмбх | Замещенные 2-окси-хинолин-3-карбоксамиды в качестве модуляторов kcnq2/3 |
| CA2807886A1 (en) | 2010-09-01 | 2012-03-08 | Gruenenthal Gmbh | Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as kcnq2/3 modulators |
| CN102070636B (zh) * | 2011-01-17 | 2012-05-23 | 浙江大学 | 喷昔洛韦的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73682A (en) | 1983-12-20 | 1991-08-16 | Medivir Ab | Antiviral pharmaceutical compositions containing 9-hydroxy aliphatic derivatives of guanine,some new such derivatives and process for their preparation |
| SE8406538D0 (sv) | 1984-12-21 | 1984-12-21 | Astra Laekemedel Ab | Novel derivatives of purine |
| GB8817607D0 (en) * | 1988-07-23 | 1988-09-01 | Beecham Group Plc | Novel process |
| JPH06279443A (ja) * | 1993-01-27 | 1994-10-04 | Asahi Chem Ind Co Ltd | ６’−ホモネプラノシンａ誘導体およびその製造法 |
| GB9407698D0 (en) | 1994-04-19 | 1994-06-15 | Smithkline Beecham Plc | Pharmaceuticals |
-
1998
- 1998-04-02 GB GBGB9807114.5A patent/GB9807114D0/en not_active Ceased
-
1999
- 1999-03-30 AU AU34200/99A patent/AU3420099A/en not_active Abandoned
- 1999-03-30 IL IL13828899A patent/IL138288A/xx not_active IP Right Cessation
- 1999-03-30 JP JP2000542324A patent/JP4524040B2/ja not_active Expired - Fee Related
- 1999-03-30 DE DE69927251T patent/DE69927251T2/de not_active Expired - Fee Related
- 1999-03-30 ES ES99915738T patent/ES2247793T3/es not_active Expired - Lifetime
- 1999-03-30 WO PCT/EP1999/002308 patent/WO1999051603A1/en not_active Ceased
- 1999-03-30 CA CA002322583A patent/CA2322583A1/en not_active Abandoned
- 1999-03-30 CN CNB998044008A patent/CN1153769C/zh not_active Expired - Fee Related
- 1999-03-30 DK DK99915738T patent/DK1068209T3/da active
- 1999-03-30 US US09/623,662 patent/US6555685B1/en not_active Expired - Lifetime
- 1999-03-30 EP EP99915738A patent/EP1068209B1/en not_active Expired - Lifetime
- 1999-03-30 KR KR1020007010707A patent/KR100701114B1/ko not_active Expired - Fee Related
- 1999-03-30 BR BR9908964-5A patent/BR9908964A/pt active Search and Examination
- 1999-03-30 AT AT99915738T patent/ATE304541T1/de not_active IP Right Cessation
-
2003
- 2003-02-19 US US10/369,841 patent/US6806375B2/en not_active Expired - Lifetime
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