JP2007528385A - オキシカルバゼピンの製造方法 - Google Patents
オキシカルバゼピンの製造方法 Download PDFInfo
- Publication number
- JP2007528385A JP2007528385A JP2007502423A JP2007502423A JP2007528385A JP 2007528385 A JP2007528385 A JP 2007528385A JP 2007502423 A JP2007502423 A JP 2007502423A JP 2007502423 A JP2007502423 A JP 2007502423A JP 2007528385 A JP2007528385 A JP 2007528385A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- oxcarbazepine
- carried out
- reaction
- 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
- 229960001816 oxcarbazepine Drugs 0.000 title claims abstract description 12
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- PIZOFBKQWNPKDK-UHFFFAOYSA-N 5-methoxybenzo[b][1]benzazepine-11-carboxamide Chemical compound COC1=CC2=CC=CC=C2N(C(N)=O)C2=CC=CC=C12 PIZOFBKQWNPKDK-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 5-methoxy-11h-benzo[b][1]benzazepine Chemical compound COC1=CC2=CC=CC=C2NC2=CC=CC=C12 ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/28—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a single bond between positions 10 and 11
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
Description
10−メトキシ−5H−ジベンゾ[b,f]アゼピン(II)100g(0.4479mol)を丸底フラスコに導入し、トルエン500mlを加えて懸濁させ、トリエチルアミン67.2g(0.6641mol)を加え、混合物を90℃まで加熱した。次に、温度を110℃まで上昇させながら、トルエン150ml中トリホスゲン66g(0.2224mol)からなる溶液を40分間かけて滴下した。
実施例1からの10−メトキシ−5H−ジベンゾ[b,f]アゼピン−5−カルボキサミド(IV)の懸濁液を入れた丸底フラスコに水600mlを加え、37%HCl約12gを滴下し、pH=1とした。懸濁液を95℃で4時間撹拌した。
重量:約80g;
収率:70%(モル),80%(w/w)。
純度(HPLC):>99%(面積%)。
Claims (7)
- 式IIの化合物に対して0.46:1〜0.54:1、より好ましくは約0.5:1のモル比のトリホスゲンを使用して前記クロロカルボニル化反応a)を実施する請求項1又は2に記載の方法。
- 式IIの化合物に対して1.4:1〜1.6:1、好ましくは約1.5:1のモル比のトリエチルアミンを塩基として使用して前記クロロカルボニル化反応a)を実施する請求項1から3のいずれか一項に記載の方法。
- トルエン中、90〜110℃の温度で前記クロロカルボニル化反応a)を実施する請求項1から4のいずれか一項に記載の方法。
- メタノール中でアンモニア水を使用して加アンモニア分解b)を実施する請求項2から5のいずれか一項に記載の方法。
- pH約1及び温度90〜95℃の水性媒体中で塩酸を使用して脱保護c)を実施する請求項2から6のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT000452A ITMI20040452A1 (it) | 2004-03-09 | 2004-03-09 | Processo per la preparazione di oxcarbazepina |
ITMI2004A000452 | 2004-03-09 | ||
PCT/IB2005/000452 WO2005092862A1 (en) | 2004-03-09 | 2005-02-21 | Process for preparing oxcarbazepine |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2007528385A true JP2007528385A (ja) | 2007-10-11 |
JP2007528385A6 JP2007528385A6 (ja) | 2008-01-17 |
JP4852528B2 JP4852528B2 (ja) | 2012-01-11 |
Family
ID=34960714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007502423A Expired - Fee Related JP4852528B2 (ja) | 2004-03-09 | 2005-02-21 | オキシカルバゼピンの製造方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7858779B2 (ja) |
EP (1) | EP1758867B1 (ja) |
JP (1) | JP4852528B2 (ja) |
KR (1) | KR101150558B1 (ja) |
DE (1) | DE602005023867D1 (ja) |
ES (1) | ES2353799T3 (ja) |
IL (1) | IL175620A0 (ja) |
IT (1) | ITMI20040452A1 (ja) |
WO (1) | WO2005092862A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100591672C (zh) | 2008-07-04 | 2010-02-24 | 浙江工业大学 | 一种奥卡西平的化学合成方法 |
US20150065704A1 (en) | 2011-07-13 | 2015-03-05 | Ketan Hirpara | Process for the preparation and purification of eslicarbazepine acetate and intermediates thereof |
EP2900640A1 (en) | 2012-09-26 | 2015-08-05 | Ranbaxy Laboratories Limited | Process for the preparation of oxcarbazepine and its use as intermediate in the preparation of eslicarbazepine acetate |
CN108101844A (zh) * | 2018-03-14 | 2018-06-01 | 常州沃腾化工科技有限公司 | 10,11-二氢-10氧代-5H-二苯并[b,f]氮杂*-5-甲酰胺的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3642775A (en) * | 1969-03-10 | 1972-02-15 | Ciba Geigy Corp | 10-oxo-10 11-dihydro-dibenzazepine derivative |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUT63389A (en) * | 1991-12-27 | 1993-08-30 | Alkaloida Vegyeszeti Gyar | Improved process for producing 5-carbamoyl-10-oxo-10,11-dihydro-5h-dibenz/b,f/azepine |
IT1272897B (it) | 1995-01-13 | 1997-07-01 | I F C Iniziative Finanziaarie | Processo per la produzione di 10-oxo-10,11-diidro-sh- -dibenz(b,f) azepin-5-carbossiammide |
DE19740577A1 (de) | 1997-09-15 | 1999-03-18 | Eckert Gmbh Dr | Verfahren und Vorrichtung zur Herstellung von Phosgen aus Diphosgen und/oder Triphosgen |
IT1301825B1 (it) | 1998-06-26 | 2000-07-07 | Archimica Spa | Procedimento per la preparazione di (s)-n-terbutil-1,2,3,4-tetraidroisochinolin-3-carbossiammide. |
GB0002740D0 (en) | 2000-02-07 | 2000-03-29 | Novartis Ag | Organic compounds |
IT1318371B1 (it) | 2000-02-22 | 2003-08-25 | Inland Internat Ltd | Processo per la preparazione di eterocicli. |
US6670472B2 (en) | 2001-10-09 | 2003-12-30 | Max India Limited | Process for the preparation of 10-methoxycarbamazepine |
US20070032647A1 (en) * | 2004-10-15 | 2007-02-08 | Amoli Organics Ltd. | Novel process for preparation of 10-oxo-10, 11-dihydro-5h-dibenz [b,f] azepine-5-carbox- amide (oxcarbazepine) via intermediate, 10-methoxy-5h-debenz[b,f] azepine-5-carbonyl- chloride |
-
2004
- 2004-03-09 IT IT000452A patent/ITMI20040452A1/it unknown
-
2005
- 2005-02-21 JP JP2007502423A patent/JP4852528B2/ja not_active Expired - Fee Related
- 2005-02-21 KR KR1020067018221A patent/KR101150558B1/ko not_active IP Right Cessation
- 2005-02-21 US US10/580,145 patent/US7858779B2/en not_active Expired - Fee Related
- 2005-02-21 EP EP05708576A patent/EP1758867B1/en not_active Not-in-force
- 2005-02-21 ES ES05708576T patent/ES2353799T3/es active Active
- 2005-02-21 DE DE602005023867T patent/DE602005023867D1/de active Active
- 2005-02-21 WO PCT/IB2005/000452 patent/WO2005092862A1/en active Application Filing
-
2006
- 2006-05-14 IL IL175620A patent/IL175620A0/en not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3642775A (en) * | 1969-03-10 | 1972-02-15 | Ciba Geigy Corp | 10-oxo-10 11-dihydro-dibenzazepine derivative |
Also Published As
Publication number | Publication date |
---|---|
JP4852528B2 (ja) | 2012-01-11 |
EP1758867B1 (en) | 2010-09-29 |
KR101150558B1 (ko) | 2012-06-01 |
KR20070031280A (ko) | 2007-03-19 |
IL175620A0 (en) | 2006-09-05 |
WO2005092862A1 (en) | 2005-10-06 |
ITMI20040452A1 (it) | 2004-06-09 |
EP1758867A1 (en) | 2007-03-07 |
US20070149507A1 (en) | 2007-06-28 |
US7858779B2 (en) | 2010-12-28 |
DE602005023867D1 (de) | 2010-11-11 |
ES2353799T3 (es) | 2011-03-07 |
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