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
Links
- 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 (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1718604A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4740884B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1922135B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2005217641B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2553572A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2005082841A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101905023B (zh) * | 2004-07-16 | 2012-07-11 | 杏林制药株式会社 | 有效的医药使用方法及与副作用发生的防御相关的方法 |
| PL1806338T3 (pl) | 2004-10-12 | 2016-07-29 | Kyorin Seiyaku Kk | Sposób wytwarzania chlorowodorku 2-amino-2-[2-[4-(3-benzyloksyfenylotio)-2-chlorofenyio]etylo]-1,3-propanodioiu i jego hydratów oraz produkty pośrednie w ich wytwarzaniu |
| WO2007043433A1 (ja) * | 2005-10-07 | 2007-04-19 | Kyorin Pharmaceutical Co., Ltd. | ２－アミノ－１，３－プロパンジオール誘導体を有効成分とする肝臓疾患治療剤および肝臓疾患治療方法 |
| 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 |
| KR101339976B1 (ko) | 2006-08-08 | 2013-12-10 | 교린 세이야꾸 가부시키 가이샤 | 아미노인산에스테르 유도체 및 그들을 유효성분으로 하는 ｓ1ｐ 수용체 조절제 |
| KR20090041424A (ko) * | 2006-08-08 | 2009-04-28 | 교린 세이야꾸 가부시키 가이샤 | 아미노알코올 유도체 및 그것들을 유효성분으로 하는 면역 억제제 |
| JP5452237B2 (ja) | 2008-02-07 | 2014-03-26 | 杏林製薬株式会社 | アミノアルコール誘導体を有効成分とする炎症性腸疾患の治療剤又は予防剤 |
| HRP20161133T1 (hr) | 2008-07-23 | 2016-12-02 | Arena Pharmaceuticals, Inc. | DERIVATI SUSPSTITUIRANE 1,2,3,4-TETRAHIDROCIKLOPENTA[b]INDOL-3-IL-OCTENE KISELINE KORISNI U LIJEČENJU AUTOIMUNIH I UPALNIH POREMEĆAJA |
| CN105816453B (zh) | 2008-08-27 | 2021-03-05 | 艾尼纳制药公司 | 用于治疗自身免疫性病症和炎性病症的作为s1p1受体激动剂的经取代的三环酸衍生物 |
| EP2528894A1 (en) | 2010-01-27 | 2012-12-05 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| CA2789480A1 (en) | 2010-03-03 | 2011-09-09 | Arena Pharmaceuticals, Inc. | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
| CA2862375A1 (en) | 2012-02-03 | 2013-08-08 | Novartis Ag | Process for preparing n-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-acetimidic acid ethyl ester |
| PT3256125T (pt) | 2014-12-11 | 2022-05-06 | Actelion Pharmaceuticals Ltd | Regime de dosagem para ponesimod, um agonista de recetor s1p1 seletivo |
| MA41139A (fr) | 2014-12-11 | 2017-10-17 | Actelion Pharmaceuticals Ltd | Combinaison pharmaceutique comportant un agoniste sélectif du récepteur sip1 |
| WO2016112075A1 (en) | 2015-01-06 | 2016-07-14 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| KR102603199B1 (ko) | 2015-06-22 | 2023-11-16 | 아레나 파마슈티칼스, 인크. | Ｓ1ｐ1 수용체-관련 장애에서의 사용을 위한 (ｒ)-2-(7-(4-시클로펜틸-3-(트리플루오로메틸)벤질옥시)-1,2,3,4-테트라히드로시클로-펜타[ｂ]인돌-3-일)아세트산 (화합물 1)의 결정성 ｌ-아르기닌 염 |
| MA47504A (fr) | 2017-02-16 | 2019-12-25 | Arena Pharm Inc | Composés et méthodes de traitement de l'angiocholite biliaire primitive |
| MA47503A (fr) | 2017-02-16 | 2021-04-21 | Arena Pharm Inc | Composés et méthodes pour le traitement de maladies inflammatoires chroniques de l'intestin avec manifestations extra-intestinales |
| CN112601516A (zh) | 2018-06-06 | 2021-04-02 | 艾尼纳制药公司 | 治疗与s1p1受体相关的病况的方法 |
| US11555015B2 (en) | 2018-09-06 | 2023-01-17 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
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 |
| KR100388120B1 (ko) * | 1998-05-11 | 2003-06-18 | 다케다 야쿠힌 고교 가부시키가이샤 | 저혈당 및 저지질혈 활성을 갖는 옥시이미노알칸산 유도체 |
| EP1550461A1 (en) * | 2002-06-26 | 2005-07-06 | Ono Pharmaceutical Co., Ltd. | Remedy for chronic disease |
| EP1594508B1 (en) * | 2003-02-11 | 2012-08-08 | Irm Llc | Novel bicyclic compounds and compositions |
| MY150088A (en) * | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| WO2004103309A2 (en) * | 2003-05-19 | 2004-12-02 | Irm Llc | Immunosuppressant compounds and compositions |
-
2005
- 2005-02-24 CN CN2005800059907A patent/CN1922135B/zh not_active Expired - Fee Related
- 2005-02-24 AU AU2005217641A patent/AU2005217641B2/en not_active Ceased
- 2005-02-24 WO PCT/US2005/006123 patent/WO2005082841A1/en not_active Ceased
- 2005-02-24 JP JP2006554337A patent/JP4740884B2/ja not_active Expired - Fee Related
- 2005-02-24 EP EP05723826A patent/EP1718604A4/en not_active Withdrawn
- 2005-02-24 US US10/590,606 patent/US7718704B2/en not_active Expired - Fee Related
- 2005-02-24 CA CA002553572A patent/CA2553572A1/en not_active Abandoned
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