JP6345665B2 - ピペリジニウム第四級塩類 - Google Patents
ピペリジニウム第四級塩類 Download PDFInfo
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- JP6345665B2 JP6345665B2 JP2015526567A JP2015526567A JP6345665B2 JP 6345665 B2 JP6345665 B2 JP 6345665B2 JP 2015526567 A JP2015526567 A JP 2015526567A JP 2015526567 A JP2015526567 A JP 2015526567A JP 6345665 B2 JP6345665 B2 JP 6345665B2
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- JP
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- Prior art keywords
- diphenyl
- acetoxy
- propoxy
- piperidinium
- methyl
- Prior art date
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
Description
従って、本発明は、プロピベリン塩酸塩よりも親油性が遥かに低く、結果としてBBBを通過しない新規のプロピベリンの第四級塩類を提供する。
好都合には、Alkはエチル、プロピル、イソプロピル、n−ブチルまたは好ましくはメチルである。
(a)プロピベリン塩酸塩の水性懸濁液を無機塩基で処理し、有機溶媒からの抽出およびその溶媒の蒸発により粗製のプロピベリン塩基を回収し;そして
(b)その残留物をアルコール溶液中で(C1〜C4)アルキルハライドで処理し、沈殿する1−アルキル−1−メチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムハライドを単離する。
上記の試験は、本発明の1−アルキル−1−メチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムハライド類が全てのmAChRサブタイプM1〜M5に関して少なくともプロピベリン塩酸塩と同じくらい親和性であること、そしてそれらがBBBを通過することができないため、それらを高い用量においてさえも、CNSにおいて抗コリン作用性の有害な作用を誘導することなく、前記の疾患の全てを治療するために用いることができることを示している。
従って、本発明はさらに、活性成分として有効量の上記の式(I)の1−アルキル−1−メチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムハライドを医薬用キャリヤーとの混合状態で含む医薬組成物を提供する。
本発明の単位形態は、経口投与のための予め測定した量の液体溶液もしくは懸濁液、経皮適用のためのパッチ、または注射のための、もしくは局所適用のための水溶液であることができる。
プロピベリン塩酸塩(50mg、0.12mM)を水(10ml)中で懸濁する。2Mの水性炭酸ナトリウム(0.5ml、1.0mM)を添加し、その反応混合物を酢酸エチルで2回抽出する。有機相を無水硫酸ナトリウムで乾燥させ、減圧下で濃縮する。その残留物を乾燥エタノール(5ml)中で溶解させ、そのエタノール溶液を0℃に冷却する。次いでヨウ化メチル(25ml、0.40mM)を添加し、その反応混合物を室温で18時間攪拌する(白色固体の形成)。形成された固体を濾別し、少量のエタノールで洗浄し、真空下で乾燥させると、1,1−ジメチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムヨージド(メチルプロピベリニウムヨージド)が白色固体として得られる(30mg;収率:48%)。融点:248℃〜250℃。
[C24H32N03]+382.4 (m/z). 1H NMR 300 MHz (DMSO D6), d : 0.84 (t, 3H, j=7.5 Hz), 1.50 (qui, 2H, j1=7.5 Hz, j2=6.6 Hz), 1.82 (br.s., 2H), 2.06 (br.s., 2H), 2.91 (br.t, 2H, j=9.3 Hz), 2.94 (s, 3H), 3.02 (s, 3H), 3.14 (t, 2H, j=6.6 Hz), 3.35 (br.s., 2H), 5.00 (m, 1H), 7.37 (m, 10H)。
経口投与のためのカプセルを、以下の成分を混合することにより調製する。
成分 重量による部
メチルプロピベリニウムヨージド 1,500
マンニトール 4,475
コロイド性二酸化ケイ素(Aerosil(登録商標)) 25
混合した後、その混合物を40メッシュのふるいを通してふるいにかけ、15mgのメチルプロピベリニウムヨージドを含有する2ピース硬質ゼラチンカプセルNo.3中に導入する。
実施例3
経口投与のための即時放出錠剤を、3.5kgのメチルプロピベリニウムヨージド、0.25kgのゼラチン、0.25kgのステアリン酸マグネシウムおよび10kgのトウモロコシデンプンを混合し、その混合物を一般に用いられる打錠機により35mgのメチルプロピベリニウムヨージドを含有する錠剤へと形成することにより調製する。
Claims (8)
- 式(I)において、Alkがメチル基である、請求項1に記載の組成物。
- 前記式(I)の1−アルキル−1−メチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムハライドが、5mgから250mgまでの量で存在する、請求項1に記載の組成物。
- 前記式(I)の1−アルキル−1−メチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムハライドが、1,1−ジメチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムヨージドである、請求項1に記載の組成物。
- 前記1,1−ジメチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムヨージドが、1,1−ジメチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムヨージドの15mgを含有するカプセル中にある、請求項4に記載の組成物。
- 前記1,1−ジメチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムヨージドが、1,1−ジメチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムヨージドの20mgを含有するカプセル中にある、請求項4に記載の組成物。
- 前記1,1−ジメチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムヨージドが、1,1−ジメチル−4−[(2,2−ジフェニル−2−プロポキシ)アセトキシ]ピペリジニウムヨージドの35mgを含有するカプセル中にある、請求項4に記載の組成物。
- 過活動膀胱症候群(OABS)、慢性閉塞性肺疾患(COPD)、または喘息の治療の使用のための、請求項1−7のいずれか1項に記載の組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261681415P | 2012-08-09 | 2012-08-09 | |
US61/681,415 | 2012-08-09 | ||
PCT/US2013/052626 WO2014025569A1 (en) | 2012-08-09 | 2013-07-30 | Piperidinium quaternary salts |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2015524469A JP2015524469A (ja) | 2015-08-24 |
JP2015524469A5 JP2015524469A5 (ja) | 2016-09-15 |
JP6345665B2 true JP6345665B2 (ja) | 2018-06-20 |
Family
ID=50068488
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015526567A Active JP6345665B2 (ja) | 2012-08-09 | 2013-07-30 | ピペリジニウム第四級塩類 |
Country Status (14)
Country | Link |
---|---|
US (1) | US9896416B2 (ja) |
EP (1) | EP2882711B1 (ja) |
JP (1) | JP6345665B2 (ja) |
KR (2) | KR102240999B1 (ja) |
CN (2) | CN104603108A (ja) |
AU (1) | AU2013300009B2 (ja) |
BR (1) | BR112015002832B1 (ja) |
CA (1) | CA2881182C (ja) |
EA (1) | EA029678B9 (ja) |
HK (1) | HK1211572A1 (ja) |
IL (1) | IL236996A0 (ja) |
IN (1) | IN2015DN01018A (ja) |
MX (1) | MX356386B (ja) |
WO (1) | WO2014025569A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10596139B2 (en) | 2015-03-06 | 2020-03-24 | Chase Pharmaceuticals Corporation | Oxybutynin transdermal therapeutic system muscarinic agonist combination |
CA2992731A1 (en) * | 2015-07-20 | 2017-01-26 | Chase Pharmaceuticals Corporation | Muscarinic combination of a selective m2-antagonist and a peripheral non-selective antagonist for treating hypocholinergic disorders |
WO2021035206A1 (en) | 2019-08-22 | 2021-02-25 | Weihua Qiao | Policy control for multiple accesses |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
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DD106643A1 (ja) | 1973-07-12 | 1974-06-20 | ||
CN1285348A (zh) | 1999-08-20 | 2001-02-28 | 广东康美药业股份有限公司 | 盐酸丙哌维林合成工艺 |
DE10129832A1 (de) * | 2001-06-17 | 2003-07-10 | Berolina Drug Dev Ab Svedala | Deuterierte N- und alpha-substituierte Diphenylalkoxyessigsäureaminoalkylester sowie diese Verbindungen enthaltende Arzneimittel |
CA2384922C (en) * | 2002-05-03 | 2008-09-02 | Purepharm Inc. | Topical glycopyrrolate product for the reduction of sweating |
KR100510788B1 (ko) | 2003-07-22 | 2005-08-26 | 동방에프티엘 주식회사 | 프로필벤질릭산 에스터로부터 염산 프로피베린의 제조방법 |
KR100500760B1 (ko) | 2003-07-22 | 2005-07-14 | 동방에프티엘 주식회사 | 염산 프로피베린의 제조방법 |
CN100569235C (zh) * | 2004-02-06 | 2009-12-16 | Meda制药有限及两合公司 | 用于哮喘和copd长期治疗的抗胆碱能药和糖皮质激素的组合 |
CA2618933C (en) * | 2005-08-12 | 2016-09-20 | Dietmar Plenz | Neuronal avalanche assay |
CN1951938A (zh) * | 2005-10-21 | 2007-04-25 | 刘丽娅 | 戊乙奎醚季铵盐及其衍生物 |
SE0600876L (sv) | 2006-04-20 | 2007-10-21 | Sandvik Intellectual Property | Verktyg och skär för spånavskiljande bearbetning med primära och sekundära ingreppsmedel med rotationssymmetrisk form |
CN101490003A (zh) * | 2006-04-24 | 2009-07-22 | 阿斯利康(瑞典)有限公司 | 具有毒蕈碱m3受体拮抗剂活性、用于治疗入慢性支气管阻塞、哮喘和膀胱过动的新型环状氨基醇的取代烷基酯类化合物 |
US20090233965A1 (en) * | 2006-04-24 | 2009-09-17 | Astrazeneca Ab | Alkyl Esters Of Cyclic Amino Alcohols With Muscarinic M3 Receptor Antagonist Activity, Useful For Treating E.G. Chronic Bronchial Obstruction, Asthma And Overactive Bladder |
EP2470504B1 (en) * | 2010-03-15 | 2013-10-16 | Ramesha Andagar Ramakrishna | Synthesis of propiverine hydrochloride |
KR101149821B1 (ko) | 2010-04-05 | 2012-05-24 | 하나제약 주식회사 | 디페닐아세테이트 유도체의 새로운 제조방법 |
CN102218063B (zh) | 2011-04-12 | 2013-03-13 | 贵州神奇制药有限公司 | 盐酸丙哌维林药物的制备方法和产品及其检测方法 |
EA038489B1 (ru) * | 2012-09-05 | 2021-09-06 | Чейс Фамасьютикалз Корпорейшн | Антихолинэргическая нейропротективная композиция и способы |
-
2013
- 2013-07-30 CN CN201380042085.3A patent/CN104603108A/zh active Pending
- 2013-07-30 US US14/419,381 patent/US9896416B2/en active Active
- 2013-07-30 EP EP13827594.6A patent/EP2882711B1/en active Active
- 2013-07-30 CA CA2881182A patent/CA2881182C/en active Active
- 2013-07-30 EA EA201500209A patent/EA029678B9/ru unknown
- 2013-07-30 KR KR1020207005139A patent/KR102240999B1/ko active IP Right Grant
- 2013-07-30 CN CN201810664740.3A patent/CN108658842A/zh active Pending
- 2013-07-30 BR BR112015002832-2A patent/BR112015002832B1/pt active IP Right Grant
- 2013-07-30 JP JP2015526567A patent/JP6345665B2/ja active Active
- 2013-07-30 AU AU2013300009A patent/AU2013300009B2/en not_active Ceased
- 2013-07-30 WO PCT/US2013/052626 patent/WO2014025569A1/en active Application Filing
- 2013-07-30 MX MX2015001769A patent/MX356386B/es active IP Right Grant
- 2013-07-30 IN IN1018DEN2015 patent/IN2015DN01018A/en unknown
- 2013-07-30 KR KR20157006047A patent/KR20150040355A/ko not_active Application Discontinuation
-
2015
- 2015-01-29 IL IL236996A patent/IL236996A0/en unknown
- 2015-12-10 HK HK15112219.3A patent/HK1211572A1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
AU2013300009A1 (en) | 2015-02-26 |
KR102240999B1 (ko) | 2021-04-15 |
MX356386B (es) | 2018-05-28 |
AU2013300009B2 (en) | 2017-06-15 |
KR20150040355A (ko) | 2015-04-14 |
CN104603108A (zh) | 2015-05-06 |
EP2882711B1 (en) | 2017-10-25 |
EP2882711A1 (en) | 2015-06-17 |
CN108658842A (zh) | 2018-10-16 |
EP2882711A4 (en) | 2016-02-10 |
CA2881182A1 (en) | 2014-02-13 |
KR20200022522A (ko) | 2020-03-03 |
IN2015DN01018A (ja) | 2015-06-26 |
EA201500209A1 (ru) | 2015-05-29 |
HK1211572A1 (en) | 2016-05-27 |
MX2015001769A (es) | 2015-05-08 |
BR112015002832A2 (ja) | 2017-07-04 |
WO2014025569A1 (en) | 2014-02-13 |
EA029678B9 (ru) | 2018-07-31 |
US9896416B2 (en) | 2018-02-20 |
JP2015524469A (ja) | 2015-08-24 |
IL236996A0 (en) | 2015-03-31 |
BR112015002832B1 (pt) | 2022-08-16 |
EA029678B1 (ru) | 2018-04-30 |
CA2881182C (en) | 2021-01-26 |
US20150203452A1 (en) | 2015-07-23 |
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