JPH10502615A - ヌクレオシド類似体のジアステレオ選択的合成法 - Google Patents
ヌクレオシド類似体のジアステレオ選択的合成法Info
- Publication number
- JPH10502615A JPH10502615A JP7527349A JP52734995A JPH10502615A JP H10502615 A JPH10502615 A JP H10502615A JP 7527349 A JP7527349 A JP 7527349A JP 52734995 A JP52734995 A JP 52734995A JP H10502615 A JPH10502615 A JP H10502615A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- mixture
- isomers
- cis
- compound
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Treatment Of Water By Oxidation Or Reduction (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. プリンまたはピリミジン塩基またはそれらの類似体との反応をルイス酸 触媒を添加せずに実施することを特徴とする、プリンまたはピリミジン塩基また はそれらの類似体を、式(IVa)または(IVb) (式中、R3は置換カルボニルまたはカルボニル誘導体であり、そしてGはハロ 、シアノまたはR5SO2−を表し、ここでR5は1または2以上のハロにより置 換されていてもよいアルキル、または置換されていてもよいフェニルを表す)の 中間体と反応させる工程を含む、式(I) (式中、 WはS、S=O、SO2またはOであり、 XはS、S=O、SO2またはOであり、 R1は水素またはアシルであり、そして R2はプリンまたはピリミジン塩基またはそれらの類似体または誘導体である ) の化合物の立体選択的製造方法。 2. R3をR1OCH2基に還元する工程をさらに含む、請求項1に記載の方 法。 3. 還元をホウ水素化ナトリウムを使用してホウ酸塩またはリン酸塩の緩衝 剤の存在下に実施する、請求項2に記載の方法。 4. R2がピリミジン塩基である、請求項1〜3のいずれか一項に記載の方 法。 5. R2がシトシンまたは5−フルオロシトシンである、請求項4に記載の 方法。 6. R3が−C(=O)OR4基(ここでR4は置換されていてもよいアルキ ル基を表す)である、請求項1〜5のいずれか一項に記載の方法。 7. R4はキラル補助基を表す、請求項6に記載の方法。 8. R4が(d)−メンチル、(l)−メンチル、(d)−8−フェニルメ ンチル、(l)−8−フェニルメンチル、(+)−ノルエフェドリンおよび(− )−ノルエフェドリンから選択される、請求項7に記載の方法。 9. WがOであり、そしてXがSである、請求項1〜8のいずれか一項に記 載の方法。 10. GはCl、BrまたはIを表す、請求項1〜9のいずれか一項に記載 の方法。 11. 式(I)の化合物が水不溶性塩として単離される、請求項の1〜10 のいずれか一項に記載の方法。 12. 式(I)の化合物が4−アミノ−1−(2R−ヒドロキシメチル−[ 1,3]オキサチオラン−5S−イル)−1H−ピリジン−2−オンまたはその サリチル酸塩である、請求項1〜11のいずれか一項に記載の方法。 13. 式(IVa)および(IVb)の中間体を式(Va)および(Vb) (式中、R3、WおよびXは請求項1において定義した通りである)の対応する トランスアルコールから、またはエピマーのシスアルコールから、G基を導入す るために適当な試薬との反応により発生させる、請求項1〜12のいずれか一項 に記載の方法。 14. 式(IVa)および(IVb)の中間体をその場で発生させる、請求 項13に記載の方法。 15. 少なくとも部分的に溶解したトランスおよびシス異性体の混合物を、 トランス異性体の結晶化を完全に抑制せずに異性体の相互変換を行うことができ る薬剤で処理することを含む、トランスおよびシス異性体の混合物からのトラン ス異性体(Va)および(Vb)の収率を増大する方法。 16. 少なくとも部分的に溶解した異性体の混合物を、所望の単一の鏡像異 性体(Va)または(Vb)の結晶化を完全に抑制せずに異性体の相互変換を行 うことができる薬剤で処理することを含む、異性体の混合物からの式(Va)ま たは(Vb)の単一の鏡像異性体の収率を増大する方法。 17. R3が−C(=O)OR4(ここでR4はl−メンチルである)である 式(Va)の化合物をアルコール(Va)、(Vb)およびエピマーのシスアル コールを含有する立体異性体の混合物から選択的に結晶化させる、請求項16に 記載の方法。 18. R3が−C(=O)OR4(ここでR4はd−メンチルである)である 式(Vb)の化合物をアルコール(Va)、(Vb)およびエピマーのシスアル コールを含有する立体異性体の混合物から選択的に結晶化させる、請求項16に 記載の方法。 19. (2R,5R)−5−ヒドロキシ−[1,3]オキサチオラン−2− カルボン酸、2S−イソプロピル−5R−メチル−1R−シクロヘキシルエステ ルの選択的結晶化のための請求項17に記載の方法。 20. 所望の単一の鏡像異性体の結晶化を完全に抑制せずに異性体の相互変 換を行うことができる薬剤がトリエチルアミンである、請求項19に記載の方法 。 21. 式(I)の化合物のサリチル酸塩またはその水和物。 22. 4−アミノ−1−(2R−ヒドロキシメチル−[1,3]オキサチオ ラン−5S−イル)−1H−ピリジン−2−オンサリチル酸塩およびその水和物 。 23. スキーム1に本質的に記載された方法。 24. 実施例1を参照して本質的に本明細書に記載された方法。
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9408112A GB9408112D0 (en) | 1994-04-23 | 1994-04-23 | Process |
GB9408091A GB9408091D0 (en) | 1994-04-23 | 1994-04-23 | Process |
GB9408103A GB9408103D0 (en) | 1994-04-23 | 1994-04-23 | Chemical compounds |
GB9408091.8 | 1994-04-23 | ||
GB9408112.2 | 1994-04-23 | ||
GB9408103.1 | 1994-04-23 | ||
PCT/EP1995/001503 WO1995029174A1 (en) | 1994-04-23 | 1995-04-21 | Process for the diastereoselective synthesis of nucleoside analogues |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007130607A Division JP2007217425A (ja) | 1994-04-23 | 2007-05-16 | ヌクレオシド類似体のジアステレオ選択的合成法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH10502615A true JPH10502615A (ja) | 1998-03-10 |
JP4056558B2 JP4056558B2 (ja) | 2008-03-05 |
Family
ID=27267157
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP52734995A Expired - Lifetime JP4056558B2 (ja) | 1994-04-23 | 1995-04-21 | ヌクレオシド類似体のジアステレオ選択的合成法 |
JP2007130607A Pending JP2007217425A (ja) | 1994-04-23 | 2007-05-16 | ヌクレオシド類似体のジアステレオ選択的合成法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007130607A Pending JP2007217425A (ja) | 1994-04-23 | 2007-05-16 | ヌクレオシド類似体のジアステレオ選択的合成法 |
Country Status (30)
Country | Link |
---|---|
US (2) | US6051709A (ja) |
EP (1) | EP0757684B1 (ja) |
JP (2) | JP4056558B2 (ja) |
KR (1) | KR100241842B1 (ja) |
CN (2) | CN1290841C (ja) |
AP (1) | AP704A (ja) |
AT (1) | ATE181326T1 (ja) |
AU (1) | AU696612B2 (ja) |
BG (1) | BG62810B1 (ja) |
BR (1) | BR9507499A (ja) |
CZ (1) | CZ293827B6 (ja) |
DE (1) | DE69510347T2 (ja) |
DK (1) | DK0757684T3 (ja) |
EE (1) | EE03442B1 (ja) |
ES (1) | ES2133769T3 (ja) |
FI (1) | FI120401B (ja) |
GR (1) | GR3031043T3 (ja) |
HK (1) | HK1004221A1 (ja) |
HU (1) | HU218044B (ja) |
IL (1) | IL113432A (ja) |
IS (1) | IS1844B (ja) |
NO (2) | NO307179B1 (ja) |
NZ (1) | NZ285396A (ja) |
PL (1) | PL180090B1 (ja) |
RO (2) | RO118714B1 (ja) |
RU (1) | RU2158736C2 (ja) |
SK (1) | SK281327B6 (ja) |
TW (1) | TW487704B (ja) |
UA (1) | UA43362C2 (ja) |
WO (1) | WO1995029174A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009108080A (ja) * | 1998-08-12 | 2009-05-21 | Triangle Pharmaceuticals Inc | 1,3−オキサチオランヌクレオチドの製造方法 |
JP2013040192A (ja) * | 2001-03-01 | 2013-02-28 | Gilead Sciences Inc | 多形型および他の結晶型のシス−ftc |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5684164A (en) * | 1988-04-11 | 1997-11-04 | Biochem Pharma Inc. | Processes for preparing substituted 1,3-oxathiolanes with antiviral properties |
IL113432A (en) * | 1994-04-23 | 2000-11-21 | Glaxo Group Ltd | Process for the diastereoselective synthesis of nucleoside analogues |
CA2203262A1 (en) * | 1994-10-22 | 1996-05-02 | Byeong Seon Jeong | Nucleoside derivatives and process for preparing thereof |
GB9506644D0 (en) * | 1995-03-31 | 1995-05-24 | Wellcome Found | Preparation of nucleoside analogues |
US6113920A (en) * | 1996-10-31 | 2000-09-05 | Glaxo Wellcome Inc. | Pharmaceutical compositions |
GB9820417D0 (en) * | 1998-09-18 | 1998-11-11 | Glaxo Group Ltd | Antiviral combinations |
US6432966B2 (en) | 1999-10-29 | 2002-08-13 | Smithkline Beecham Corporation | Antiviral combinations |
CA2351049C (en) | 2001-06-18 | 2007-03-13 | Brantford Chemicals Inc. | Process for recovery of the desired cis-1,3-oxathiolane nucleosides from their undesired trans-isomers |
WO2003027106A1 (en) * | 2001-09-25 | 2003-04-03 | Cadila Healthcar Limited | Process for the preparation of crystalline polymorph ii of lamivudine |
ITMI20030578A1 (it) * | 2003-03-24 | 2004-09-25 | Clariant Lsm Italia Spa | Processo ed intermedi per la preparazione di emtricitabina |
US20050187913A1 (en) | 2003-05-06 | 2005-08-25 | Yoram Nelken | Web-based customer service interface |
CN101307048B (zh) | 2007-05-18 | 2011-03-23 | 上海迪赛诺医药发展有限公司 | 立体选择性制备拉米夫定的方法 |
WO2009037538A2 (en) * | 2007-09-17 | 2009-03-26 | Aurobindo Pharma Ltd | Process for the preparation of lamivudine form i |
EP2048151A1 (en) * | 2007-10-10 | 2009-04-15 | Cilag AG | Method for producing nucleosides by direct glycosylation of the nucleoside base |
BRPI0820224A2 (pt) * | 2007-11-29 | 2015-06-16 | Ranbaxy Lab Ltd | Composto de fórmula iii ou seus estereoisômeros; processo para sua preparação e seu uso; uso de um composto de formula iii(a) ou iii(b) em um processo para a preparação de lamivudina de fórmula i(a) ou um composto de fórmula i(c); processo para preparação de lamivudina de fórmula i(a) |
CN101918393A (zh) * | 2007-11-29 | 2010-12-15 | 兰贝克赛实验室有限公司 | 拉米夫定的晶形i及其制备方法 |
SI2225232T1 (sl) | 2007-11-29 | 2012-12-31 | Ranbaxy Laboratories Limited | Postopek za pripravo substituiranih 1,3-oksatiolanov |
US8350030B2 (en) * | 2007-12-07 | 2013-01-08 | Matrix Laboratories Limited | Process for producing 5-fluoro-1-(2R, 5S)-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine |
CN101391997B (zh) * | 2008-09-18 | 2010-12-22 | 江苏科本医药化学有限公司 | 一种恩曲他滨中间体的合成方法 |
CN101362752B (zh) * | 2008-09-18 | 2011-12-28 | 浙江教育学院 | 一种拉米夫定中间体的合成方法 |
US20110282046A1 (en) | 2009-01-19 | 2011-11-17 | Rama Shankar | Process for preparation of cis-nucleoside derivative |
KR101474570B1 (ko) | 2009-04-13 | 2014-12-19 | 주식회사 대희화학 | 라미부딘의 신규한 중간체 및 이의 제조방법 |
CN101544632B (zh) * | 2009-04-24 | 2011-09-07 | 湖南千金湘江药业股份有限公司 | 拉米夫定非对映选择合成方法 |
ES2540074T3 (es) | 2009-10-14 | 2015-07-08 | Mylan Laboratories Limited | Proceso para la preparación de lamivudina y nuevas sales en la fabricación de la misma |
TR201807704T4 (tr) | 2010-01-27 | 2018-06-21 | Viiv Healthcare Co | Anti-viral tedavi. |
WO2011095987A1 (en) | 2010-02-03 | 2011-08-11 | Matrix Laboratories Ltd. | Novel process for the preparation of cis-nucleoside derivative |
CN102167696B (zh) * | 2010-02-25 | 2013-09-18 | 南京正大天晴制药有限公司 | 拉米夫定草酸盐及其制备方法 |
EP2542551B1 (en) * | 2010-03-04 | 2014-08-27 | Ranbaxy Laboratories Limited | A process for stereoselective synthesis of 5-fluoro-1-(2r,5s)-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine |
CN101830893A (zh) * | 2010-05-31 | 2010-09-15 | 安徽一帆香料有限公司 | 一种拉米夫定中间体hdms的合成制备工艺 |
CN102399213A (zh) * | 2010-09-08 | 2012-04-04 | 重庆医药工业研究院有限责任公司 | 拉米夫定单邻苯二甲酸盐及其合成方法 |
WO2012062835A1 (en) | 2010-11-12 | 2012-05-18 | Glaxo Wellcome Manufacturing Pte Ltd | Novel pharmaceutical compositions |
CN103282369A (zh) | 2011-04-08 | 2013-09-04 | 劳乐斯实验室私营有限公司 | 抗逆转录病毒化合物与抗氧化酸的固体形式、其制备方法以及其药物组合物 |
CN102796088B (zh) * | 2012-05-21 | 2015-06-10 | 湖南千金湘江药业股份有限公司 | 一种拉米夫定的制备方法 |
CN103450166A (zh) * | 2012-05-31 | 2013-12-18 | 上海迪赛诺药业有限公司 | 制备核苷化合物的方法 |
CN103864835A (zh) * | 2013-03-26 | 2014-06-18 | 安徽贝克联合制药有限公司 | 一种提高拉米夫定中间体立体选择性制备方法 |
CN103288806A (zh) * | 2013-07-02 | 2013-09-11 | 山东大学 | 一种曲沙他滨的合成方法 |
CN103694231A (zh) * | 2013-11-28 | 2014-04-02 | 安徽一帆香料有限公司 | 一种拉米夫定中间体hdms的合成制备方法 |
US9571109B2 (en) * | 2015-03-27 | 2017-02-14 | International Business Machines Corporation | Voltage controlled oscillator runaway prevention |
CN106146481A (zh) * | 2015-04-07 | 2016-11-23 | 江苏普信制药有限公司 | 一种核苷类似物的制备方法 |
CN105037340B (zh) * | 2015-07-14 | 2018-08-10 | 福建广生堂药业股份有限公司 | 一种拉米夫定关键中间体手性异构体杂质的制备方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5684164A (en) * | 1988-04-11 | 1997-11-04 | Biochem Pharma Inc. | Processes for preparing substituted 1,3-oxathiolanes with antiviral properties |
US5047407A (en) * | 1989-02-08 | 1991-09-10 | Iaf Biochem International, Inc. | 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties |
US5466806A (en) * | 1989-02-08 | 1995-11-14 | Biochem Pharma Inc. | Processes for preparing substituted 1,3-oxathiolanes with antiviral properties |
AU3154993A (en) * | 1989-02-08 | 1994-07-19 | Biochem Pharma Inc. | Process for preparing substituted 1,3-oxathiolanes with antiviral properties |
US5204466A (en) * | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
GB9009861D0 (en) * | 1990-05-02 | 1990-06-27 | Glaxo Group Ltd | Chemical compounds |
US5587480A (en) * | 1990-11-13 | 1996-12-24 | Biochem Pharma, Inc. | Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties |
IL100502A (en) * | 1991-01-03 | 1995-12-08 | Iaf Biochem Int | PHARMACEUTICAL PREPARATIONS CONTAINING CIS-4-AMINO-1-) 2-HYDROXIMETHIL-1,3-OXETYOLEN-5-IL (- |
DK0513917T4 (da) | 1991-05-16 | 2001-06-25 | Glaxo Group Ltd | Antivirale kombinationer indeholdende nukleosidanaloger |
GB9110874D0 (en) * | 1991-05-20 | 1991-07-10 | Iaf Biochem Int | Medicaments |
ZA923640B (en) * | 1991-05-21 | 1993-02-24 | Iaf Biochem Int | Processes for the diastereoselective synthesis of nucleosides |
GB9116601D0 (en) * | 1991-08-01 | 1991-09-18 | Iaf Biochem Int | 1,3-oxathiolane nucleoside analogues |
IL113432A (en) * | 1994-04-23 | 2000-11-21 | Glaxo Group Ltd | Process for the diastereoselective synthesis of nucleoside analogues |
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1995
- 1995-04-20 IL IL11343295A patent/IL113432A/xx not_active IP Right Cessation
- 1995-04-21 AU AU24471/95A patent/AU696612B2/en not_active Expired
- 1995-04-21 RO ROA200101248A patent/RO118714B1/ro unknown
- 1995-04-21 AT AT95918579T patent/ATE181326T1/de active
- 1995-04-21 NZ NZ285396A patent/NZ285396A/xx not_active IP Right Cessation
- 1995-04-21 HU HU9602925A patent/HU218044B/hu unknown
- 1995-04-21 DK DK95918579T patent/DK0757684T3/da active
- 1995-04-21 AP APAP/P/1996/000871A patent/AP704A/en active
- 1995-04-21 ES ES95918579T patent/ES2133769T3/es not_active Expired - Lifetime
- 1995-04-21 UA UA96103961A patent/UA43362C2/uk unknown
- 1995-04-21 CZ CZ19963096A patent/CZ293827B6/cs not_active IP Right Cessation
- 1995-04-21 WO PCT/EP1995/001503 patent/WO1995029174A1/en active IP Right Grant
- 1995-04-21 EE EE9600134A patent/EE03442B1/xx unknown
- 1995-04-21 RO RO96-02034A patent/RO117916B1/ro unknown
- 1995-04-21 BR BR9507499A patent/BR9507499A/pt not_active Application Discontinuation
- 1995-04-21 KR KR1019960705918A patent/KR100241842B1/ko not_active IP Right Cessation
- 1995-04-21 DE DE69510347T patent/DE69510347T2/de not_active Expired - Lifetime
- 1995-04-21 US US08/722,224 patent/US6051709A/en not_active Expired - Lifetime
- 1995-04-21 PL PL95316904A patent/PL180090B1/pl unknown
- 1995-04-21 CN CNB031452116A patent/CN1290841C/zh not_active Expired - Lifetime
- 1995-04-21 SK SK1355-96A patent/SK281327B6/sk not_active IP Right Cessation
- 1995-04-21 EP EP95918579A patent/EP0757684B1/en not_active Expired - Lifetime
- 1995-04-21 CN CNB95193466XA patent/CN1151146C/zh not_active Expired - Lifetime
- 1995-04-21 JP JP52734995A patent/JP4056558B2/ja not_active Expired - Lifetime
- 1995-04-21 RU RU96122244/04A patent/RU2158736C2/ru active
- 1995-04-27 TW TW084104194A patent/TW487704B/zh not_active IP Right Cessation
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1996
- 1996-09-27 IS IS4366A patent/IS1844B/is unknown
- 1996-10-16 BG BG100916A patent/BG62810B1/bg unknown
- 1996-10-22 FI FI964251A patent/FI120401B/fi not_active IP Right Cessation
- 1996-10-22 NO NO964487A patent/NO307179B1/no not_active IP Right Cessation
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1998
- 1998-04-27 HK HK98103525A patent/HK1004221A1/xx not_active IP Right Cessation
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1999
- 1999-06-23 US US09/338,493 patent/US6329522B1/en not_active Expired - Lifetime
- 1999-08-19 GR GR990402121T patent/GR3031043T3/el unknown
- 1999-11-17 NO NO19995646A patent/NO313096B1/no not_active IP Right Cessation
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2007
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2009108080A (ja) * | 1998-08-12 | 2009-05-21 | Triangle Pharmaceuticals Inc | 1,3−オキサチオランヌクレオチドの製造方法 |
JP2013040192A (ja) * | 2001-03-01 | 2013-02-28 | Gilead Sciences Inc | 多形型および他の結晶型のシス−ftc |
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