JP2007523909A5 - - Google Patents
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- Publication number
- JP2007523909A5 JP2007523909A5 JP2006554337A JP2006554337A JP2007523909A5 JP 2007523909 A5 JP2007523909 A5 JP 2007523909A5 JP 2006554337 A JP2006554337 A JP 2006554337A JP 2006554337 A JP2006554337 A JP 2006554337A JP 2007523909 A5 JP2007523909 A5 JP 2007523909A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- halo
- alkoxy
- cyclohexyl
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 8
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 8
- 102000036530 EDG receptors Human genes 0.000 claims description 7
- 108091007263 EDG receptors Proteins 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 210000004698 lymphocyte Anatomy 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 241001465754 Metazoa Species 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 230000004075 alteration Effects 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 230000002074 deregulated effect Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000011664 signaling Effects 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- WECBDLFIELAVDJ-UHFFFAOYSA-N 1-[[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-2,3-dihydrochromen-7-yl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C(CCO2)=NOCC=3C=C(C(C4CCCCC4)=CC=3)C(F)(F)F)C2=C1 WECBDLFIELAVDJ-UHFFFAOYSA-N 0.000 claims 1
- UXOSEONDYXAAQY-UHFFFAOYSA-N 1-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-3-methoxy-7,8-dihydro-6h-naphthalen-2-yl]methyl]azetidine-3-carboxylic acid Chemical compound COC1=CC=2C(=NOCC=3C=C(C(C4CCCCC4)=CC=3)C(F)(F)F)CCCC=2C=C1CN1CC(C(O)=O)C1 UXOSEONDYXAAQY-UHFFFAOYSA-N 0.000 claims 1
- GNOYLVBEQDEBEV-UHFFFAOYSA-N 1-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-7,8-dihydro-6h-naphthalen-2-yl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C(CCC2)=NOCC=3C=C(C(C4CCCCC4)=CC=3)C(F)(F)F)C2=C1 GNOYLVBEQDEBEV-UHFFFAOYSA-N 0.000 claims 1
- QQJPDUFMQSQWLT-UHFFFAOYSA-N 1-[[8-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-6,7-dihydro-5h-naphthalen-2-yl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(CCCC2=NOCC=3C=C(C(C4CCCCC4)=CC=3)C(F)(F)F)C2=C1 QQJPDUFMQSQWLT-UHFFFAOYSA-N 0.000 claims 1
- UFDZQYQZIYVKMA-UHFFFAOYSA-N 3-[[3-chloro-5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-7,8-dihydro-6h-naphthalen-2-yl]methylamino]propanoic acid Chemical compound C1=2C=C(Cl)C(CNCCC(=O)O)=CC=2CCCC1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 UFDZQYQZIYVKMA-UHFFFAOYSA-N 0.000 claims 1
- NBWVHSJZOUXTGG-UHFFFAOYSA-N 3-[[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-2,3-dihydrochromen-6-yl]methylamino]propanoic acid Chemical compound C12=CC(CNCCC(=O)O)=CC=C2OCCC1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 NBWVHSJZOUXTGG-UHFFFAOYSA-N 0.000 claims 1
- WXQRXFBWRZRHQT-UHFFFAOYSA-N 3-[[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-2,3-dihydrochromen-7-yl]methylamino]propanoic acid Chemical compound C1COC2=CC(CNCCC(=O)O)=CC=C2C1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 WXQRXFBWRZRHQT-UHFFFAOYSA-N 0.000 claims 1
- GUYNHJIYFMAAHR-UHFFFAOYSA-N 3-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-3-ethyl-7,8-dihydro-6h-naphthalen-2-yl]methylamino]propanoic acid Chemical compound C1CCC=2C=C(CNCCC(O)=O)C(CC)=CC=2C1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 GUYNHJIYFMAAHR-UHFFFAOYSA-N 0.000 claims 1
- XQQIHUKEIBQKKB-UHFFFAOYSA-N 3-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-3-methoxy-7,8-dihydro-6h-naphthalen-2-yl]methylamino]propanoic acid Chemical compound C1CCC=2C=C(CNCCC(O)=O)C(OC)=CC=2C1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 XQQIHUKEIBQKKB-UHFFFAOYSA-N 0.000 claims 1
- KXUGYIBWAYBOQD-UHFFFAOYSA-N 3-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-7,8-dihydro-6h-naphthalen-2-yl]methylamino]propanoic acid Chemical compound C1CCC2=CC(CNCCC(=O)O)=CC=C2C1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 KXUGYIBWAYBOQD-UHFFFAOYSA-N 0.000 claims 1
- HIHLNVLPMUSWPM-UHFFFAOYSA-N 3-[[6-chloro-4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-2,3-dihydrochromen-7-yl]methylamino]propanoic acid Chemical compound C1=2C=C(Cl)C(CNCCC(=O)O)=CC=2OCCC1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 HIHLNVLPMUSWPM-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 125000000815 N-oxide group Chemical group 0.000 claims 1
- 206010029113 Neovascularisation Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Chemical group 0.000 claims 1
- 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 description 9
- 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000027455 binding Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 101000693269 Homo sapiens Sphingosine 1-phosphate receptor 3 Proteins 0.000 description 1
- 101000653759 Homo sapiens Sphingosine 1-phosphate receptor 5 Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102100025747 Sphingosine 1-phosphate receptor 3 Human genes 0.000 description 1
- 102100029802 Sphingosine 1-phosphate receptor 5 Human genes 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54771204P | 2004-02-24 | 2004-02-24 | |
| US60/547,712 | 2004-02-24 | ||
| PCT/US2005/006123 WO2005082841A1 (en) | 2004-02-24 | 2005-02-24 | Immunosuppressant compounds and compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007523909A JP2007523909A (ja) | 2007-08-23 |
| JP2007523909A5 true JP2007523909A5 (https=) | 2008-04-10 |
| JP4740884B2 JP4740884B2 (ja) | 2011-08-03 |
Family
ID=34910931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006554337A Expired - Fee Related JP4740884B2 (ja) | 2004-02-24 | 2005-02-24 | 免疫抑制性化合物および組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7718704B2 (https=) |
| EP (1) | EP1718604A4 (https=) |
| JP (1) | JP4740884B2 (https=) |
| CN (1) | CN1922135B (https=) |
| AU (1) | AU2005217641B2 (https=) |
| CA (1) | CA2553572A1 (https=) |
| WO (1) | WO2005082841A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7781617B2 (en) | 2004-07-16 | 2010-08-24 | Kyorin Pharmaceutical Co., Ltd | Effective use method of medicaments and method of preventing expression of side effect |
| EP1806338B1 (en) | 2004-10-12 | 2016-01-20 | Kyorin Pharmaceutical Co., Ltd. | Process for producing 2-amino-2-[2-[4-(3-benzyloxy-phenylthio)-2-chlorophenyl[ethyl]-1,3-propanediol hydrochloride and hydrates thereof. and intermediates the production thereof |
| PL1932522T3 (pl) * | 2005-10-07 | 2012-09-28 | Kyorin Seiyaku Kk | Środek terapeutyczny do leczenia choroby wątroby zawierający jako składnik czynny pochodną 2-amino-1,3-propanodiolu |
| TWI389683B (zh) * | 2006-02-06 | 2013-03-21 | Kyorin Seiyaku Kk | A therapeutic agent for an inflammatory bowel disease or an inflammatory bowel disease treatment using a 2-amino-1,3-propanediol derivative as an active ingredient |
| JP5140593B2 (ja) | 2006-08-08 | 2013-02-06 | 杏林製薬株式会社 | アミノアルコール誘導体及びそれらを有効成分とする免疫抑制剤 |
| CA2659598A1 (en) | 2006-08-08 | 2008-02-14 | Kyorin Pharmaceutical Co., Ltd. | Amino phosphate derivative and s1p receptor modulator having same as an active ingredient |
| TW200946105A (en) | 2008-02-07 | 2009-11-16 | Kyorin Seiyaku Kk | Therapeutic agent or preventive agent for inflammatory bowel disease containing amino alcohol derivative as active ingredient |
| US8580841B2 (en) | 2008-07-23 | 2013-11-12 | Arena Pharmaceuticals, Inc. | Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders |
| HRP20160890T1 (hr) | 2008-08-27 | 2016-09-23 | Arena Pharmaceuticals, Inc. | Derivati supstituirane tricikličke kiseline kao agonisti s1p1-receptora korisni u liječenju autoimunih i upalnih poremećaja |
| JP5856980B2 (ja) | 2010-01-27 | 2016-02-10 | アリーナ ファーマシューティカルズ， インコーポレイテッド | （Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸およびその塩の調製のためのプロセス |
| CN105503882B (zh) | 2010-03-03 | 2019-07-05 | 艾尼纳制药公司 | 制备s1p1受体调节剂及其晶体形式的方法 |
| CA2862375A1 (en) * | 2012-02-03 | 2013-08-08 | Novartis Ag | Process for preparing n-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-acetimidic acid ethyl ester |
| MA41139B1 (fr) | 2014-12-11 | 2026-02-27 | Laboratoires Juvise Pharmaceuticals | Combinaison pharmaceutique comprenant du ponesimod et son utilisation dans le traitement de la sclérose en plaque |
| KR20200013086A (ko) | 2014-12-11 | 2020-02-05 | 액테리온 파마슈티칼 리미티드 | 선택적 s1p1 수용체 효능제에 대한 투약 섭생 |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| MX2019009841A (es) | 2017-02-16 | 2020-01-30 | Arena Pharm Inc | Compuestos y metodos para el tratamiento de la colangitis biliar primaria. |
| MX2019009843A (es) | 2017-02-16 | 2020-01-30 | Arena Pharm Inc | Compuestos y metodos para el tratamiento de la enfermedad inflamatoria intestinal con manifestaciones extraintestinales. |
| CA3102136A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| CN112955431A (zh) | 2018-09-06 | 2021-06-11 | 艾尼纳制药公司 | 可用于治疗自身免疫性病症和炎性病症的化合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3872113A (en) | 1972-05-30 | 1975-03-18 | Endo Lab | Hydroxy- and acetoxy-phthalaldehydric acid, O-(substituted) oximes |
| US5674879A (en) * | 1993-09-24 | 1997-10-07 | G.D. Searle & Co. | Compositions including and methods of using conformationally restricted angiotensin II antagonist |
| HUP0103714A3 (en) * | 1998-05-11 | 2003-05-28 | Takeda Pharmaceutical | Oxyiminoalkanoic acid derivatives with hypoglycemic and hypolipidemic activity, medicaments containing them and their use |
| US7300917B2 (en) * | 2002-06-26 | 2007-11-27 | Ono Pharmaceuticals Co., Ltd. | Remedy for chronic disease |
| PL378134A1 (pl) * | 2003-02-11 | 2006-03-06 | Irm Llc | Nowe pochodne bicykliczne i kompozycje farmaceutyczne zawierające pochodne bicykliczne |
| MY150088A (en) * | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| MXPA05012459A (es) * | 2003-05-19 | 2006-02-22 | Irm Llc | Compuestos y composiciones inmunosupresoras. |
-
2005
- 2005-02-24 US US10/590,606 patent/US7718704B2/en not_active Expired - Fee Related
- 2005-02-24 CN CN2005800059907A patent/CN1922135B/zh not_active Expired - Fee Related
- 2005-02-24 CA CA002553572A patent/CA2553572A1/en not_active Abandoned
- 2005-02-24 EP EP05723826A patent/EP1718604A4/en not_active Withdrawn
- 2005-02-24 WO PCT/US2005/006123 patent/WO2005082841A1/en not_active Ceased
- 2005-02-24 AU AU2005217641A patent/AU2005217641B2/en not_active Ceased
- 2005-02-24 JP JP2006554337A patent/JP4740884B2/ja not_active Expired - Fee Related
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