JP2010168359A5 - - Google Patents
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- JP2010168359A5 JP2010168359A5 JP2009289494A JP2009289494A JP2010168359A5 JP 2010168359 A5 JP2010168359 A5 JP 2010168359A5 JP 2009289494 A JP2009289494 A JP 2009289494A JP 2009289494 A JP2009289494 A JP 2009289494A JP 2010168359 A5 JP2010168359 A5 JP 2010168359A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ethynyl
- butoxy
- phenyl
- indole
- 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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- -1 3-carboxypropyl group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011780 sodium chloride Substances 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- HLPSHXIVNYPKND-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F HLPSHXIVNYPKND-UHFFFAOYSA-N 0.000 claims 3
- HOXJOAWSVADHMC-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-2-methyl-7-[2-[4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C=C(F)C(F)=C1F HOXJOAWSVADHMC-UHFFFAOYSA-N 0.000 claims 3
- SILHYVDKGHXGBL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-7-[2-[4-[4-(3-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(F)=C1C SILHYVDKGHXGBL-UHFFFAOYSA-N 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- TXTOGNHBXCXSDY-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(F)C(F)=C(F)C=4F)F)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 TXTOGNHBXCXSDY-UHFFFAOYSA-N 0.000 claims 1
- URNRXOPHGYWKLX-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-7-[2-[4-[4-(3-chloro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(Cl)C=CC=4)C)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 URNRXOPHGYWKLX-UHFFFAOYSA-N 0.000 claims 1
- ZSIOUYAJBOECNZ-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-7-[2-[4-[4-(3-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(F)C=CC=4)C)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 ZSIOUYAJBOECNZ-UHFFFAOYSA-N 0.000 claims 1
- PYUVJTWRSZWPDP-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,5-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC(F)=C(F)C(F)=C1F PYUVJTWRSZWPDP-UHFFFAOYSA-N 0.000 claims 1
- HUIIHFBKBWWWJM-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C=C(F)C(F)=C1F HUIIHFBKBWWWJM-UHFFFAOYSA-N 0.000 claims 1
- BCNPNPHFYVYYGW-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(3,4,5-trifluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC(F)=C(F)C(F)=C1 BCNPNPHFYVYYGW-UHFFFAOYSA-N 0.000 claims 1
- OKNHXOCNFKQLBL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F OKNHXOCNFKQLBL-UHFFFAOYSA-N 0.000 claims 1
- CUZTUQOWAJAZCQ-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CN(CCCC(O)=O)C2=C1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F CUZTUQOWAJAZCQ-UHFFFAOYSA-N 0.000 claims 1
- AWYSEGZBFYYQQL-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(3-chloro-2-methylphenyl)butoxy]phenyl]ethynyl]-4-fluoro-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=CC(Cl)=C1C AWYSEGZBFYYQQL-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
Claims (11)
- R1が3−カルボキシプロピル基であり、R3が3−カルボキシプロピル基である請求項2記載の化合物。
- 化合物が、
(1) 4,4’−[2−メチル−7−({4−[4−(ペンタフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸、
(2) 4,4’−[7−({4−[4−(3−クロロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−1,3−ジイル]ジブタン酸、
(3) 4,4’−[2−メチル−7−({4−[4−(3,4,5−トリフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸、
(5) 4,4’−[7−({4−[4−(3−フルオロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−1,3−ジイル]ジブタン酸、
(6) 4,4’−[2−メチル−7−({4−[4−(2,3,4,5−テトラフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸、
(7) 4,4’−[2−メチル−7−({4−[4−(2,3,4,6−テトラフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸、
(8) 4,4’−[7−({4−[4−(4−フルオロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−1,3−ジイル]ジブタン酸、
(9) 4,4’−[7−({4−[4−(4−フルオロ−3−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−1,3−ジイル]ジブタン酸、
(10) 4,4’−[4−フルオロ−2−メチル−7−({4−[4−(ペンタフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸、
(11) 4,4’−[7−({4−[4−(3−クロロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−4−フルオロ−2−メチル−1H−インドール−1,3−ジイル]ジブタン酸、
(12) 4,4'−[4−フルオロ−7−({4−[4−(3−フルオロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−1,3−ジイル]ジブタン酸、
(13) 4,4’−[4−フルオロ−2−メチル−7−({4−[4−(2,3,4,6−テトラフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸、
(14) [3−{[1−(カルボキシメチル)シクロプロピル]メチル}−2−メチル−7−({4−[4−(ペンタフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1−イル]酢酸、
(15) (1−{[1−(カルボキシメチル)−7−({4−[4−(3−クロロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−3−イル]メチル}シクロプロピル)酢酸、
(16) [3−{[1−(カルボキシメチル)シクロプロピル]メチル}−7−({4−[4−(3−フルオロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−1−イル]酢酸、または
(17) 4,4’−[7−({4−[4−(ペンタフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸である
請求項1記載の化合物。 - 請求項1記載の一般式(I)で示される化合物、その塩、もしくはそれらの溶媒和物を有効成分として含有してなる医薬組成物。
- 4,4’−[2−メチル−7−({4−[4−(ペンタフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸、その塩、またはそれらの溶媒和物。
- 4,4’−[4−フルオロ−7−({4−[4−(3−フルオロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−1,3−ジイル]ジブタン酸、その塩、またはそれらの溶媒和物。
- 4,4’−[4−フルオロ−2−メチル−7−({4−[4−(2,3,4,6−テトラフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸、その塩、またはそれらの溶媒和物。
- 4,4’−[2−メチル−7−({4−[4−(ペンタフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸。
- 4,4’−[4−フルオロ−7−({4−[4−(3−フルオロ−2−メチルフェニル)ブトキシ]フェニル}エチニル)−2−メチル−1H−インドール−1,3−ジイル]ジブタン酸。
- 4,4’−[4−フルオロ−2−メチル−7−({4−[4−(2,3,4,6−テトラフルオロフェニル)ブトキシ]フェニル}エチニル)−1H−インドール−1,3−ジイル]ジブタン酸。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009289494A JP5012884B2 (ja) | 2008-12-22 | 2009-12-21 | エチニルインドール化合物 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008325815 | 2008-12-22 | ||
JP2008325815 | 2008-12-22 | ||
JP2009289494A JP5012884B2 (ja) | 2008-12-22 | 2009-12-21 | エチニルインドール化合物 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012050217A Division JP2012144546A (ja) | 2008-12-22 | 2012-03-07 | エチニルインドール化合物 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010168359A JP2010168359A (ja) | 2010-08-05 |
JP2010168359A5 true JP2010168359A5 (ja) | 2011-12-08 |
JP5012884B2 JP5012884B2 (ja) | 2012-08-29 |
Family
ID=42110130
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009289494A Active JP5012884B2 (ja) | 2008-12-22 | 2009-12-21 | エチニルインドール化合物 |
JP2012050217A Withdrawn JP2012144546A (ja) | 2008-12-22 | 2012-03-07 | エチニルインドール化合物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012050217A Withdrawn JP2012144546A (ja) | 2008-12-22 | 2012-03-07 | エチニルインドール化合物 |
Country Status (18)
Country | Link |
---|---|
US (1) | US8115014B2 (ja) |
EP (1) | EP2206698B1 (ja) |
JP (2) | JP5012884B2 (ja) |
KR (1) | KR101464778B1 (ja) |
CN (1) | CN101759628B (ja) |
AU (1) | AU2009250960C1 (ja) |
BR (1) | BRPI0905601A2 (ja) |
CA (1) | CA2688614C (ja) |
DK (1) | DK2206698T3 (ja) |
ES (1) | ES2387185T3 (ja) |
IL (1) | IL202869A (ja) |
MX (1) | MX2009013926A (ja) |
NZ (1) | NZ582208A (ja) |
PL (1) | PL2206698T3 (ja) |
PT (1) | PT2206698E (ja) |
RU (1) | RU2505531C2 (ja) |
TW (1) | TWI469965B (ja) |
ZA (1) | ZA200909096B (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011162222A1 (ja) | 2010-06-21 | 2011-12-29 | 小野薬品工業株式会社 | 4,4'-[4-フルオロ-7-({4-[4-(3-フルオロ-2-メチルフェニル)ブトキシ]フェニル}エチニル)-2-メチル-1h-インドール-1,3-ジイル]ジブタン酸、4,4'-[2-メチル-7-({4-[4-(ペンタフルオロフェニル)ブトキシ]フェニル}エチニル)-1h-インドール-1,3-ジイル]ジブタン酸および4,4'-[4-フルオロ-2-メチル-7-({4-[4-(2,3,4,6-テトラフルオロフェニル)ブトキシ]フェニル}エチニル)-1h-インドール-1,3-ジイル]ジブタン酸の新規結晶形 |
KR101171790B1 (ko) | 2010-07-30 | 2012-08-13 | 현대자동차주식회사 | 인출식 자전거 캐리어 |
WO2012089633A1 (fr) | 2010-12-28 | 2012-07-05 | Sanofi | Nouveaux derives de pyrimidines, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de phosphorylation d'akt(pkb) |
EP2537866A1 (en) * | 2011-06-21 | 2012-12-26 | Serumwerk Bernburg AG | Hydroxyethyl starch derivatives, method for manufacturing the same and therapeutical uses thereof |
CN103893146A (zh) * | 2012-12-25 | 2014-07-02 | 天津药物研究院 | 含福多司坦缓释剂型 |
WO2020079652A1 (en) * | 2018-10-17 | 2020-04-23 | Insilico Medicine Hong Kong Limited | Kinase inhibitors |
Family Cites Families (21)
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BE555319A (ja) | 1956-03-21 | 1900-01-01 | ||
US3095355A (en) | 1961-10-12 | 1963-06-25 | Revlon | Aerosol composition |
JPH01192476A (ja) | 1988-01-25 | 1989-08-02 | Kawasaki Steel Corp | 溶接鋼管の製造方法 |
JPH0347123A (ja) | 1989-05-05 | 1991-02-28 | G D Searle & Co | インドール―2―カルボキシレート化合物類を含有するcns疾患治療用組成物 |
US5229413A (en) | 1989-05-05 | 1993-07-20 | G. D. Searle & Co. | Compositions containing indole-2-carboxylate compounds for treatment of CNS disorders |
US5137910A (en) | 1989-05-05 | 1992-08-11 | C.D. Searle & Co. | Compositions containing indole-2-carboxylate compounds for treatment of CNS disorders |
CA2019335C (en) | 1989-06-27 | 2000-08-01 | Mitoshi Konno | Phenylalkan (en)oic acids |
GB9027018D0 (en) * | 1990-12-12 | 1991-01-30 | Ici Plc | Heterocyclic compounds |
US5530019A (en) | 1993-04-05 | 1996-06-25 | Fujisawa Pharmaceutical Co., Ltd. | Indole derivatives useful as testosterone 5α-reductase inhibitors |
US5965745A (en) | 1995-10-10 | 1999-10-12 | Pfizer Inc | Indole carbamates as leukotriene antagonists |
FR2766824B1 (fr) | 1997-07-30 | 1999-09-10 | Adir | Nouveaux composes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
GB9902455D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
AU2001270200A1 (en) | 2000-06-27 | 2002-01-08 | Smith Kline Beecham Corporation | Fatty acid synthase inhibitors |
JP2003025362A (ja) | 2001-07-18 | 2003-01-29 | Nippon Tokushu Toryo Co Ltd | 通気性を有する発泡プラスチック及びその製法 |
US6867224B2 (en) | 2002-03-07 | 2005-03-15 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods of preparation |
US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
AU2003239150A1 (en) | 2002-04-23 | 2003-11-10 | Aventis Pharmaceuticals Inc. | 3-substituted amino-1h-indole-2-carboxylic acid and 3-substituted amino-benzo |
SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
EP1628970A2 (en) | 2003-04-30 | 2006-03-01 | The Institutes of Pharmaceutical Discovery, LLC | Heterocycle substituted carboxylic acids as inhibitors of protein tyrosine phosphatase-1b |
US7763610B2 (en) * | 2003-09-01 | 2010-07-27 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derived benzoxazines as agents for the treatment of respiratory diseases |
EP1852420B1 (en) * | 2005-02-25 | 2012-10-17 | Ono Pharmaceutical Co., Ltd. | Indole compounds for treating respiratory disorders |
-
2009
- 2009-12-10 TW TW98142268A patent/TWI469965B/zh not_active IP Right Cessation
- 2009-12-15 CA CA2688614A patent/CA2688614C/en not_active Expired - Fee Related
- 2009-12-15 AU AU2009250960A patent/AU2009250960C1/en not_active Ceased
- 2009-12-17 MX MX2009013926A patent/MX2009013926A/es active IP Right Grant
- 2009-12-21 DK DK09180244.7T patent/DK2206698T3/da active
- 2009-12-21 RU RU2009147506/04A patent/RU2505531C2/ru not_active IP Right Cessation
- 2009-12-21 EP EP09180244A patent/EP2206698B1/en not_active Not-in-force
- 2009-12-21 IL IL202869A patent/IL202869A/en not_active IP Right Cessation
- 2009-12-21 NZ NZ582208A patent/NZ582208A/en not_active IP Right Cessation
- 2009-12-21 KR KR1020090128213A patent/KR101464778B1/ko not_active IP Right Cessation
- 2009-12-21 CN CN2009102608650A patent/CN101759628B/zh not_active Expired - Fee Related
- 2009-12-21 BR BRPI0905601-7A patent/BRPI0905601A2/pt not_active IP Right Cessation
- 2009-12-21 PL PL09180244T patent/PL2206698T3/pl unknown
- 2009-12-21 ZA ZA200909096A patent/ZA200909096B/en unknown
- 2009-12-21 PT PT09180244T patent/PT2206698E/pt unknown
- 2009-12-21 JP JP2009289494A patent/JP5012884B2/ja active Active
- 2009-12-21 ES ES09180244T patent/ES2387185T3/es active Active
- 2009-12-22 US US12/644,378 patent/US8115014B2/en not_active Expired - Fee Related
-
2012
- 2012-03-07 JP JP2012050217A patent/JP2012144546A/ja not_active Withdrawn
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