JP2000515552A - 抗腫瘍アシルフルベンの全合成 - Google Patents
抗腫瘍アシルフルベンの全合成Info
- Publication number
- JP2000515552A JP2000515552A JP10508128A JP50812898A JP2000515552A JP 2000515552 A JP2000515552 A JP 2000515552A JP 10508128 A JP10508128 A JP 10508128A JP 50812898 A JP50812898 A JP 50812898A JP 2000515552 A JP2000515552 A JP 2000515552A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
- give
- group
- 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
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
- C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
- C07C49/737—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 式(V)の化合物: 〔上式中、R’は(C1〜C4)アルキルである〕の合成方法であって、 式(II)のシクロペンテノン: 〔上式中、R4は−O−C(R9)2O(R9)であり、ここでR9は(C1〜C4) アルキルである〕を、式(III)の環状カルボニルイリド双極子: とカッブリングせしめて、式(IV)の化合物: を生成する段階;そして 化合物(IV)を塩基で処理して式(V)のケトンを生成する段階を含んで成る 方法。 2. 前記ケトンをジヒドロキシル化して、式(VI)の化合物:を生成する段階、そして 式(VI)の化合物を除去可能な1,2−ジオール保護試薬で処理して式(VII )の中間体: (上式中Xは除去可能な1,2−ジオール保護基である)を生成する段階 を更に含んで成る、請求項1に記載の方法。 3. 式(VII)の化合物をRMgCl〔ここでRは(C1〜C4)アルキルであ る〕で処理して式(VIII)のグリニャール生成物: を生成する段階、そして その酸素ブリッジを開裂せしめて式(IX)のジオール:を生成する段階 を更に含んで成る、請求項2に記載の方法。 4. 前記除去可能なジオール保護基を除去して式(X)のテトラオール: を生成する段階を更に含んで成る、請求項3に記載の方法。 5. 前記テトラオールを式(XI)のオルトエステル: 〔上式中、R”は(C1〜C3アルキルである〕に変換する段階;そして シス−ヒドロキシルを脱離せしめて式(XII)のジエノン: を生成する段階 を更に含んで成る、請求項4に記載の方法。 6. 生成するアルコールを脱水する条件下で式(XII)の化合物を還元する ことによりケトンをアルコールに変換して、式(XIII)のフルベン: を生成する段階を更に含んで成る、請求項5に記載の方法。 7. 式(XIII)のフルベンを酸化して式(I)の化合物: を生成する段階を更に含んで成る、請求項6に記載の方法。 8. R9がCH3である、請求項7に記載の方法。 9. R’がメチルである、請求項7に記載の方法。 10. Rがメチルである、請求項7に記載の方法。 11. 式(XIII)のジケトン: 〔上式中、R’は(C1〜C4)アルキルである〕の合成方法であって、 (a) 式(XIV)の化合物中の酸素ブリッジを開裂せしめて式(XIII)のジケトンを生成する段階を含んで成る方法。 12.(b) 式(XIII)の化合物中のヒドロキシル基を除去可能なヒドロキシル 保護基Xで保護する段階;そして (c) 五員環中に1つの二重結合を導入して式(XV)の化合物: (上式中R’1とR’2は一緒になってケトであり、そしてXは除去可能なヒドロ キシル保護基である)を生成する段階 を更に含んで成る、請求項11に記載の方法。 13.(d) 式(XVI)の化合物を生成する条件下で両方のケト基を還元してヒ ドロキシ基を生成する段階; (e) シクロペンテノールヒドロキシル基を脱離せしめる段階;そして (f) シクロヘキサノールヒドロキシル基を酸化しそしてヒドロキシル保護基 Xを除去して、式(XVII)の化合物:(上式中R1はOHでありそしてR2はHである)を生成する段階を更に含んで成 る、請求項12に記載の方法。 14.(g) 段階(d)の後に、前記アルコールを塩化メシルで処理して式(XVIII )のメシレート: (上式中、R”1は−OXであり、R”2は存在せず、そしてRは Hである)を生成する段階を更に含んで成る、請求項13に記載の方法。 15.Xが((C1〜C4)アルキル)3Si−である、請求項12に記載の方法。 16.式(XIII)の化合物のカルボニル基をアセタール基に変換して、式(XI X)の化合物: (上式中、R’1とR’2は一緒になってエチレンジオキシである)を生成する段 階を更に含んで成る、請求項11に記載の方法。 17.(b) 化合物(XIX)中のヒドロキシル基を除去可能なヒドロキシル保護 基Xで保護する段階;そして (c) 五員環中に1つの二重結合を導入して、式(XX)の化合物: (上式中、Xは除去可能な保護基である)を生成する段階 を更に含んで成る、請求項16に記載の方法。 18.(d) 式(XXI)の化合物を生成する条件下でケト基を還元してヒドロ キシル基にする段階; (e) シクロペンテノールヒドロキシル基を脱離せしめる段階; (f) ヒドロキシル保護基Xを除去して式(XXII)の化合物: を生成する段階;そして (g) シクロヘキサノールヒドロキシル基を酸化して式(XXIII)の化合物: を生成する段階 を更に含んで成る、請求項17に記載の方法。 19.(h) 段階(d)の後に、前記アルコールを塩基の存在下で塩化メシルで処理 して式(XXIV)のメシレート: を生成する段階を更に含んで成る、請求項18に記載の方法。 20.Xが((C1〜C4)アルキル)3Si−である、請求項17に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/689,461 | 1996-08-08 | ||
US08/689,461 US5723632A (en) | 1996-08-08 | 1996-08-08 | Total synthesis of antitumor acylfulvenes |
PCT/US1997/013644 WO1998005669A1 (en) | 1996-08-08 | 1997-08-05 | Total synthesis of antitumor acylfulvenes |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2000515552A true JP2000515552A (ja) | 2000-11-21 |
JP4267702B2 JP4267702B2 (ja) | 2009-05-27 |
Family
ID=24768581
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50812898A Expired - Fee Related JP4267702B2 (ja) | 1996-08-08 | 1997-08-05 | 抗腫瘍アシルフルベンの全合成 |
Country Status (12)
Country | Link |
---|---|
US (6) | US5723632A (ja) |
EP (2) | EP0918776B1 (ja) |
JP (1) | JP4267702B2 (ja) |
AT (1) | ATE263771T1 (ja) |
AU (1) | AU3744397A (ja) |
CA (1) | CA2262648A1 (ja) |
DE (1) | DE69728544T2 (ja) |
DK (1) | DK0918776T3 (ja) |
ES (1) | ES2215234T3 (ja) |
HK (1) | HK1019878A1 (ja) |
PT (1) | PT918776E (ja) |
WO (1) | WO1998005669A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002503714A (ja) * | 1998-02-20 | 2002-02-05 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 抗腫瘍剤 |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5932553A (en) * | 1996-07-18 | 1999-08-03 | The Regents Of The University Of California | Illudin analogs useful as antitumor agents |
US5723632A (en) | 1996-08-08 | 1998-03-03 | Mgi Pharma, Inc. | Total synthesis of antitumor acylfulvenes |
US7141603B2 (en) * | 1999-02-19 | 2006-11-28 | The Regents Of The University California | Antitumor agents |
US6635490B1 (en) * | 2000-05-25 | 2003-10-21 | Noble Laboratories | Procedure for the simultaneous quantitative and qualitative analysis of both flavonoid glycosides and steroidal glycosides |
DE60142313D1 (de) * | 2000-10-02 | 2010-07-15 | Univ Emory | Triptolid-analoga zur behandlung von autoimmunkranheiten und entzündungen |
US7015247B2 (en) * | 2000-10-12 | 2006-03-21 | Alvin Guttag | Ibuprofen-aspirin, hydroxymethylacylfulvene analogs and L-sugar illudin analogs |
US6436916B1 (en) | 2000-10-12 | 2002-08-20 | Alvin Guttag | Ibuprofen-aspirin and hydroxymethylacylfulvene analogs |
BR0210607B1 (pt) * | 2001-06-22 | 2011-06-28 | catalisador de metaloceno, sistema catalìtico para a polimerização de olefina, processos para a polimerização de olefina, e para a preparação de um catalisador e metaloceno, e, composto. | |
US7718385B2 (en) * | 2003-10-17 | 2010-05-18 | The Johns Hopkins University | Bioactivation of alkylating agents for cancer treatment |
WO2007019308A2 (en) * | 2005-08-03 | 2007-02-15 | The Regents Of The University Of California | Illudin analogs useful as anticancer agents |
JP5528806B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
US20080275016A1 (en) * | 2007-05-03 | 2008-11-06 | Arbiser Jack L | Fulvene and fulvalene analogs and their use in treating cancers |
GB0715576D0 (en) * | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
EP2240460A4 (en) * | 2008-01-07 | 2012-02-22 | Univ Emory | BRANCHED DIEPXYDE COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS |
CN106458922A (zh) | 2014-04-10 | 2017-02-22 | Af化学药品有限责任公司 | 亲和药物共轭物 |
US11135182B2 (en) | 2014-04-10 | 2021-10-05 | Af Chemicals, Llc | Affinity medicant conjugates |
US10285955B2 (en) | 2014-04-10 | 2019-05-14 | Af Chemicals, Llc | Affinity medicant conjugate |
CN104650160A (zh) * | 2015-01-13 | 2015-05-27 | 济南大学 | 卡培他滨关键中间体1,2,3-o-三乙酰基-5-脱氧-d-核糖的合成新方法 |
MX2021002529A (es) * | 2018-09-04 | 2021-08-11 | Lantern Paharma Inc | Analogos de illudin, usos de los mismos y metodos para sintetizar los mismos. |
US11160807B1 (en) | 2018-12-11 | 2021-11-02 | Af Chemicals, Llc | Methods, compositions and devices for treating cancer with illudofulvenes |
US11591295B2 (en) | 2019-11-25 | 2023-02-28 | Af Chemicals Llc | Affinity illudofulvene conjugates |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4559157A (en) * | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
LU84979A1 (fr) * | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
US4612302A (en) * | 1983-11-14 | 1986-09-16 | Brigham And Women's Hospital | Clinical use of somatostatin analogues |
US4684620A (en) * | 1984-09-04 | 1987-08-04 | Gibson-Stephens Neuropharmaceuticals, Inc. | Cyclic polypeptides having mu-receptor specificity |
JPS62234040A (ja) * | 1986-04-02 | 1987-10-14 | Kyowa Hakko Kogyo Co Ltd | Dc1043物質 |
US4853371A (en) * | 1986-06-17 | 1989-08-01 | The Administrators Of The Tulane Educational Fund | Therapeutic somatostatin analogs |
US4820508A (en) * | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
US4992478A (en) * | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
US4938949A (en) * | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
US5439936A (en) * | 1989-10-03 | 1995-08-08 | The Regents Of The University Of California | Method of treating certain tumors using illudin analogs |
JPH05503077A (ja) * | 1989-10-03 | 1993-05-27 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 抗腫瘍剤としてのイルージンアナログ |
GB9017024D0 (en) * | 1990-08-03 | 1990-09-19 | Erba Carlo Spa | New linker for bioactive agents |
DZ1773A1 (fr) * | 1993-04-27 | 2002-02-17 | Smithkline Beecham Corp | Antagonistes de récepteurs d'endothéline. |
US6303120B1 (en) * | 1994-03-15 | 2001-10-16 | Memorial Sloan-Kettering Institute For Cancer Research | Synthesis of glycoconjugates of the lewis y epitope and uses thereof |
US5708163A (en) * | 1994-03-15 | 1998-01-13 | Sloan-Kettering Institute Of Cancer Research | Synthesis of the breast tumor-associated antigen defined by monoclonalantibody MBRL and uses thereof |
US5932553A (en) * | 1996-07-18 | 1999-08-03 | The Regents Of The University Of California | Illudin analogs useful as antitumor agents |
US5723632A (en) * | 1996-08-08 | 1998-03-03 | Mgi Pharma, Inc. | Total synthesis of antitumor acylfulvenes |
US6025328A (en) | 1998-02-20 | 2000-02-15 | The Regents Of The University Of California | Antitumor agents |
-
1996
- 1996-08-08 US US08/689,461 patent/US5723632A/en not_active Expired - Lifetime
-
1997
- 1997-08-05 CA CA002262648A patent/CA2262648A1/en not_active Abandoned
- 1997-08-05 DK DK97934366T patent/DK0918776T3/da active
- 1997-08-05 PT PT97934366T patent/PT918776E/pt unknown
- 1997-08-05 WO PCT/US1997/013644 patent/WO1998005669A1/en active IP Right Grant
- 1997-08-05 JP JP50812898A patent/JP4267702B2/ja not_active Expired - Fee Related
- 1997-08-05 AT AT97934366T patent/ATE263771T1/de not_active IP Right Cessation
- 1997-08-05 EP EP97934366A patent/EP0918776B1/en not_active Expired - Lifetime
- 1997-08-05 EP EP20040007952 patent/EP1454890A3/en not_active Withdrawn
- 1997-08-05 DE DE69728544T patent/DE69728544T2/de not_active Expired - Lifetime
- 1997-08-05 ES ES97934366T patent/ES2215234T3/es not_active Expired - Lifetime
- 1997-08-05 US US09/242,091 patent/US6160184A/en not_active Expired - Lifetime
- 1997-08-05 AU AU37443/97A patent/AU3744397A/en not_active Abandoned
- 1997-10-31 US US08/961,650 patent/US5856580A/en not_active Expired - Fee Related
-
1999
- 1999-11-08 HK HK99105109A patent/HK1019878A1/xx not_active IP Right Cessation
-
2000
- 2000-10-05 US US09/679,831 patent/US6252093B1/en not_active Expired - Fee Related
-
2001
- 2001-06-05 US US09/874,839 patent/US6469184B2/en not_active Expired - Fee Related
-
2002
- 2002-08-30 US US10/231,575 patent/US6717017B2/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002503714A (ja) * | 1998-02-20 | 2002-02-05 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 抗腫瘍剤 |
Also Published As
Publication number | Publication date |
---|---|
US5723632A (en) | 1998-03-03 |
US6469184B2 (en) | 2002-10-22 |
ES2215234T3 (es) | 2004-10-01 |
US6160184A (en) | 2000-12-12 |
WO1998005669A1 (en) | 1998-02-12 |
EP1454890A8 (en) | 2004-11-03 |
CA2262648A1 (en) | 1998-02-12 |
EP1454890A2 (en) | 2004-09-08 |
US20010029303A1 (en) | 2001-10-11 |
DE69728544D1 (de) | 2004-05-13 |
HK1019878A1 (en) | 2000-03-03 |
AU3744397A (en) | 1998-02-25 |
US6252093B1 (en) | 2001-06-26 |
US6717017B2 (en) | 2004-04-06 |
JP4267702B2 (ja) | 2009-05-27 |
PT918776E (pt) | 2004-07-30 |
DK0918776T3 (da) | 2004-07-12 |
US5856580A (en) | 1999-01-05 |
EP1454890A3 (en) | 2004-11-10 |
EP0918776B1 (en) | 2004-04-07 |
US20030050495A1 (en) | 2003-03-13 |
ATE263771T1 (de) | 2004-04-15 |
DE69728544T2 (de) | 2004-09-16 |
EP0918776A1 (en) | 1999-06-02 |
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