JP2005500345A5 - - Google Patents
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- Publication number
- JP2005500345A5 JP2005500345A5 JP2003516514A JP2003516514A JP2005500345A5 JP 2005500345 A5 JP2005500345 A5 JP 2005500345A5 JP 2003516514 A JP2003516514 A JP 2003516514A JP 2003516514 A JP2003516514 A JP 2003516514A JP 2005500345 A5 JP2005500345 A5 JP 2005500345A5
- Authority
- JP
- Japan
- Prior art keywords
- indol
- alkyl
- substituted
- sulfonyl
- aryl
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 47
- 125000003118 aryl group Chemical group 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 229910052799 carbon Inorganic materials 0.000 claims 24
- 125000000547 substituted alkyl group Chemical group 0.000 claims 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000001624 naphthyl group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- -1 substituted Chemical class 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 230000037396 body weight Effects 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- NELPBEUIKAVHQD-UHFFFAOYSA-N 2-(2-methyl-5-naphthalen-1-ylsulfonyl-1h-indol-3-yl)ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=CC=C4NC(=C(C4=C3)CCN)C)=CC=CC2=C1 NELPBEUIKAVHQD-UHFFFAOYSA-N 0.000 claims 3
- UREMGOQLUQXFJL-UHFFFAOYSA-N 2-[5-(3,5-difluorophenyl)sulfonyl-1,2-dimethylindol-3-yl]-n-methylethanamine Chemical compound C1=C2C(CCNC)=C(C)N(C)C2=CC=C1S(=O)(=O)C1=CC(F)=CC(F)=C1 UREMGOQLUQXFJL-UHFFFAOYSA-N 0.000 claims 3
- RQBLNPUMXBCFNO-UHFFFAOYSA-N 2-[5-(3,5-difluorophenyl)sulfonyl-1,2-dimethylindol-3-yl]ethanamine Chemical compound C=1C=C2N(C)C(C)=C(CCN)C2=CC=1S(=O)(=O)C1=CC(F)=CC(F)=C1 RQBLNPUMXBCFNO-UHFFFAOYSA-N 0.000 claims 3
- LLIOTKAPGWUDLW-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)-1,2-dimethylindol-3-yl]ethanamine Chemical compound C=1C=C2N(C)C(C)=C(CCN)C2=CC=1S(=O)(=O)C1=CC=CC=C1 LLIOTKAPGWUDLW-UHFFFAOYSA-N 0.000 claims 3
- UZKANRSZEKXWBK-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)-1-methylindol-3-yl]ethanamine Chemical compound C=1C=C2N(C)C=C(CCN)C2=CC=1S(=O)(=O)C1=CC=CC=C1 UZKANRSZEKXWBK-UHFFFAOYSA-N 0.000 claims 3
- MNKKKEXJDXIOMJ-UHFFFAOYSA-N 2-(1,2-dimethyl-5-naphthalen-1-ylsulfonylindol-3-yl)ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=C4C(CCN)=C(N(C4=CC=3)C)C)=CC=CC2=C1 MNKKKEXJDXIOMJ-UHFFFAOYSA-N 0.000 claims 2
- JDDNLLGCJUJSHT-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)-1,2-dimethylindol-3-yl]-n-methylethanamine Chemical compound C1=C2C(CCNC)=C(C)N(C)C2=CC=C1S(=O)(=O)C1=CC=CC=C1 JDDNLLGCJUJSHT-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010003805 Autism Diseases 0.000 claims 2
- 208000020706 Autistic disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- MLUOGHSPITZEOK-UHFFFAOYSA-N 2-(1,2-dimethyl-5-naphthalen-1-ylsulfonylindol-3-yl)-n-methylethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=CC=C4N(C)C(C)=C(C4=C3)CCNC)=CC=CC2=C1 MLUOGHSPITZEOK-UHFFFAOYSA-N 0.000 claims 1
- ITFGBWUSEPYTHU-UHFFFAOYSA-N 2-[1,2-dimethyl-5-(4-methylphenyl)sulfonylindol-3-yl]-n-methylethanamine Chemical compound C1=C2C(CCNC)=C(C)N(C)C2=CC=C1S(=O)(=O)C1=CC=C(C)C=C1 ITFGBWUSEPYTHU-UHFFFAOYSA-N 0.000 claims 1
- ZIEOCPTYWQLJCV-UHFFFAOYSA-N 2-[1,2-dimethyl-5-(4-methylphenyl)sulfonylindol-3-yl]ethanamine Chemical compound C=1C=C2N(C)C(C)=C(CCN)C2=CC=1S(=O)(=O)C1=CC=C(C)C=C1 ZIEOCPTYWQLJCV-UHFFFAOYSA-N 0.000 claims 1
- RAOZZDDCVWLTRO-UHFFFAOYSA-N 2-[1,2-dimethyl-5-[4-(trifluoromethyl)phenyl]sulfonylindol-3-yl]-n-methylethanamine Chemical compound C1=C2C(CCNC)=C(C)N(C)C2=CC=C1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 RAOZZDDCVWLTRO-UHFFFAOYSA-N 0.000 claims 1
- WBQZOOCVAVTLOQ-UHFFFAOYSA-N 2-[1,2-dimethyl-5-[4-(trifluoromethyl)phenyl]sulfonylindol-3-yl]ethanamine Chemical compound C=1C=C2N(C)C(C)=C(CCN)C2=CC=1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 WBQZOOCVAVTLOQ-UHFFFAOYSA-N 0.000 claims 1
- OUGAFGRZMQOEIF-UHFFFAOYSA-N 2-[1-methyl-5-(4-methylphenyl)sulfonylindol-3-yl]ethanamine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC=C(N(C)C=C2CCN)C2=C1 OUGAFGRZMQOEIF-UHFFFAOYSA-N 0.000 claims 1
- PXKPSYOITWSBKH-UHFFFAOYSA-N 2-[2-methyl-5-(4-methylphenyl)sulfonyl-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=C(C)NC2=CC=C1S(=O)(=O)C1=CC=C(C)C=C1 PXKPSYOITWSBKH-UHFFFAOYSA-N 0.000 claims 1
- JQJQAQDABDUXML-UHFFFAOYSA-N 2-[2-methyl-5-[4-(trifluoromethyl)phenyl]sulfonyl-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=C(C)NC2=CC=C1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 JQJQAQDABDUXML-UHFFFAOYSA-N 0.000 claims 1
- OQHKVIGXVGSBCT-UHFFFAOYSA-N 2-[5-(3,5-difluorophenyl)sulfonyl-2-methyl-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=C(C)NC2=CC=C1S(=O)(=O)C1=CC(F)=CC(F)=C1 OQHKVIGXVGSBCT-UHFFFAOYSA-N 0.000 claims 1
- HJHIRISEUZGYTQ-UHFFFAOYSA-N 2-[5-(3-methoxyphenyl)sulfonyl-1,2-dimethylindol-3-yl]-n-methylethanamine Chemical compound C1=C2C(CCNC)=C(C)N(C)C2=CC=C1S(=O)(=O)C1=CC=CC(OC)=C1 HJHIRISEUZGYTQ-UHFFFAOYSA-N 0.000 claims 1
- BARSALPWPUGACB-UHFFFAOYSA-N 2-[5-(3-methoxyphenyl)sulfonyl-1,2-dimethylindol-3-yl]ethanamine Chemical compound COC1=CC=CC(S(=O)(=O)C=2C=C3C(CCN)=C(C)N(C)C3=CC=2)=C1 BARSALPWPUGACB-UHFFFAOYSA-N 0.000 claims 1
- KDCIXEOCFNUDCE-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)-1,2-dimethylindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=C2C(CCN(C)C)=C(C)N(C)C2=CC=C1S(=O)(=O)C1=CC=CC=C1 KDCIXEOCFNUDCE-UHFFFAOYSA-N 0.000 claims 1
- RWGCLAKCGJWBIT-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)-2-methyl-1h-indol-3-yl]-n-methylethanamine Chemical compound C1=C2C(CCNC)=C(C)NC2=CC=C1S(=O)(=O)C1=CC=CC=C1 RWGCLAKCGJWBIT-UHFFFAOYSA-N 0.000 claims 1
- UAKBZSDLNOGZRK-UHFFFAOYSA-N 2-[5-(benzenesulfonyl)-2-methyl-1h-indol-3-yl]ethanamine Chemical compound C1=C2C(CCN)=C(C)NC2=CC=C1S(=O)(=O)C1=CC=CC=C1 UAKBZSDLNOGZRK-UHFFFAOYSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- SGZZILDVPIWUDJ-UHFFFAOYSA-N COc1cccc(c1)S(=O)(=O)c1ccc2[nH]c(C)c(CCN)c2c1.COc1cccc(c1)S(=O)(=O)c1ccc2n(C)c(C)c(CCN)c2c1 Chemical compound COc1cccc(c1)S(=O)(=O)c1ccc2[nH]c(C)c(CCN)c2c1.COc1cccc(c1)S(=O)(=O)c1ccc2n(C)c(C)c(CCN)c2c1 SGZZILDVPIWUDJ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- QJGQUHMNIGDVPM-BJUDXGSMSA-N Nitrogen-13 Chemical compound [13N] QJGQUHMNIGDVPM-BJUDXGSMSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-BJUDXGSMSA-N ac1l2y5h Chemical compound [18FH] KRHYYFGTRYWZRS-BJUDXGSMSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-BJUDXGSMSA-N carbon-11 Chemical compound [11C] OKTJSMMVPCPJKN-BJUDXGSMSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 claims 1
- WDFVUCPIPLUHNA-UHFFFAOYSA-N n-methyl-2-[1-methyl-5-(4-methylphenyl)sulfonylindol-3-yl]ethanamine Chemical compound C1=C2C(CCNC)=CN(C)C2=CC=C1S(=O)(=O)C1=CC=C(C)C=C1 WDFVUCPIPLUHNA-UHFFFAOYSA-N 0.000 claims 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 claims 1
- QVGXLLKOCUKJST-BJUDXGSMSA-N oxygen-15 atom Chemical compound [15O] QVGXLLKOCUKJST-BJUDXGSMSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002600 positron emission tomography Methods 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- SSAVDLPACQMBQP-UHFFFAOYSA-N tert-butyl n-[2-[5-(benzenesulfonyl)-1,2-dimethylindol-3-yl]ethyl]-n-methylcarbamate Chemical compound C1=C2C(CCN(C)C(=O)OC(C)(C)C)=C(C)N(C)C2=CC=C1S(=O)(=O)C1=CC=CC=C1 SSAVDLPACQMBQP-UHFFFAOYSA-N 0.000 claims 1
- GPSPPHXFEULOET-UHFFFAOYSA-N tert-butyl n-[2-[5-(benzenesulfonyl)-1,2-dimethylindol-3-yl]ethyl]carbamate Chemical compound C=1C=C2N(C)C(C)=C(CCNC(=O)OC(C)(C)C)C2=CC=1S(=O)(=O)C1=CC=CC=C1 GPSPPHXFEULOET-UHFFFAOYSA-N 0.000 claims 1
- OGGRXWQJARUWQH-UHFFFAOYSA-N tert-butyl n-[2-[5-(benzenesulfonyl)-1-methylindol-3-yl]ethyl]carbamate Chemical compound C=1C=C2N(C)C=C(CCNC(=O)OC(C)(C)C)C2=CC=1S(=O)(=O)C1=CC=CC=C1 OGGRXWQJARUWQH-UHFFFAOYSA-N 0.000 claims 1
- DJNPSJIAUHAEOX-UHFFFAOYSA-N tert-butyl n-[2-[5-(benzenesulfonyl)-1h-indol-3-yl]ethyl]carbamate Chemical compound C1=C2C(CCNC(=O)OC(C)(C)C)=CNC2=CC=C1S(=O)(=O)C1=CC=CC=C1 DJNPSJIAUHAEOX-UHFFFAOYSA-N 0.000 claims 1
- XNKVQFRXQMVMRV-UHFFFAOYSA-N tert-butyl n-[2-[5-(benzenesulfonyl)-2-methyl-1h-indol-3-yl]ethyl]carbamate Chemical compound C1=C2C(CCNC(=O)OC(C)(C)C)=C(C)NC2=CC=C1S(=O)(=O)C1=CC=CC=C1 XNKVQFRXQMVMRV-UHFFFAOYSA-N 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30983201P | 2001-08-03 | 2001-08-03 | |
| US32688501P | 2001-10-03 | 2001-10-03 | |
| PCT/US2002/024759 WO2003011284A1 (en) | 2001-08-03 | 2002-08-01 | 5-arylsulfonyl indoles having 5-ht6 receptor affinity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005500345A JP2005500345A (ja) | 2005-01-06 |
| JP2005500345A5 true JP2005500345A5 (enExample) | 2005-09-29 |
Family
ID=26977033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003516514A Pending JP2005500345A (ja) | 2001-08-03 | 2002-08-01 | ５−ｈｔ６受容体親和性を有する５−アリールスルホニルインドール |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6565829B2 (enExample) |
| EP (1) | EP1411925A1 (enExample) |
| JP (1) | JP2005500345A (enExample) |
| BR (1) | BR0211561A (enExample) |
| CA (1) | CA2452743A1 (enExample) |
| MX (1) | MXPA04001089A (enExample) |
| WO (1) | WO2003011284A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04009318A (es) | 2002-03-27 | 2005-01-25 | Glaxo Group Ltd | Derivados de quinolina y su uso como ligados 5-ht6. |
| US7393537B2 (en) | 2003-04-25 | 2008-07-01 | Allergan, Inc. | Botulinum toxin for treatment of obsessive compulsive finger biting disorder |
| WO2004096269A2 (en) * | 2003-04-25 | 2004-11-11 | Allergan, Inc. | Botulinum neurotoxin for treating tics and obsessive compulsive behaviors |
| ATE407671T1 (de) * | 2003-05-09 | 2008-09-15 | Esteve Labor Dr | Verwendung von sulfonamid-derivate zur herstellung eines medikaments für die vorbeugung oder behandlung von essstörungen |
| JP4198733B2 (ja) | 2003-07-22 | 2008-12-17 | 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 | 関連性障害の予防および処置に有用な、５−ｈｔ２ａセロトニンレセプターのモジュレーターとしてのジアリールおよびアリールへテロアリールウレア誘導体 |
| DE102004048716A1 (de) * | 2004-10-06 | 2006-04-20 | Dr. Willmar Schwabe Gmbh & Co. Kg | Verwendung von Lavendelöl zur Prophylaxe und Behandlung von Neurasthenie, Somatisierungsstörungen und von anderen stress-assoziierten Erkrankungen |
| GB0422263D0 (en) * | 2004-10-07 | 2004-11-10 | Glaxo Group Ltd | Novel compounds |
| ES2337482T3 (es) * | 2004-12-21 | 2010-04-26 | F. Hoffmann-La Roche Ag | Derivados de tetralina y de indano y usos de los mismos. |
| DE602005007064D1 (de) * | 2004-12-21 | 2008-07-03 | Hoffmann La Roche | Chromanderivate und ihre verwendung als liganden des 5-ht-rezeptors |
| MX2007007481A (es) * | 2004-12-21 | 2007-07-20 | Hoffmann La Roche | Derivados de tetralina e indano y usos de los mismos. |
| CA2618636C (en) * | 2005-08-12 | 2011-01-18 | Suven Life Sciences Limited | Aminoaryl sulphonamide derivatives as functional 5-ht6 ligands |
| WO2007051735A1 (en) * | 2005-11-03 | 2007-05-10 | F. Hoffmann-La Roche Ag | Arylsulfonylchromans as 5-ht6 inhibitors indolylmaleimide derivatives as protein kinase inhibitors |
| BRPI0713742A2 (pt) * | 2006-06-20 | 2013-02-13 | Hoffmann La Roche | derivados de arilsulfonila naftaleno e usos destes |
| CN101500611A (zh) * | 2006-06-23 | 2009-08-05 | 埃斯蒂维实验室股份有限公司 | 胆碱脂酶抑制剂与具有5-ht6受体亲和力的化合物的组合 |
| EP2508177A1 (en) | 2007-12-12 | 2012-10-10 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| EP2236511A4 (en) | 2007-12-21 | 2011-04-13 | Alla Chem Llc | LIGANDS OF ALPHA ADRENOCEPTORS AND OF DOPAMINE, HISTAMIN, IMIDAZOLIN AND SEROTONIN RECEPTORS AND THEIR APPLICATION THEREOF |
| US20110021538A1 (en) | 2008-04-02 | 2011-01-27 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| WO2016201373A1 (en) | 2015-06-12 | 2016-12-15 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives useful for the prophylaxis and treatment of rem sleep behavior disorder |
| HK1247555A1 (zh) | 2015-07-15 | 2018-09-28 | Axovant Sciences Gmbh | 用於预防和治疗与神经变性疾病相关的幻觉的作为5-ht2a血清素受体的调节剂的二芳基脲和芳基杂芳基脲衍生物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9226532D0 (en) | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| CA2322162A1 (en) | 1998-02-25 | 1999-09-02 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| GB9820113D0 (en) * | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| MY122278A (en) * | 1999-07-19 | 2006-04-29 | Upjohn Co | 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| DK1379239T3 (da) * | 2001-03-29 | 2008-01-07 | Lilly Co Eli | N(2-aryl-ethyl)-benzyl-aminer som antagonister af 5 HT6 receptoren |
-
2002
- 2002-08-01 EP EP02756958A patent/EP1411925A1/en not_active Withdrawn
- 2002-08-01 WO PCT/US2002/024759 patent/WO2003011284A1/en not_active Ceased
- 2002-08-01 CA CA002452743A patent/CA2452743A1/en not_active Abandoned
- 2002-08-01 US US10/210,377 patent/US6565829B2/en not_active Expired - Fee Related
- 2002-08-01 MX MXPA04001089A patent/MXPA04001089A/es unknown
- 2002-08-01 BR BR0211561-1A patent/BR0211561A/pt not_active IP Right Cessation
- 2002-08-01 JP JP2003516514A patent/JP2005500345A/ja active Pending
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