JP2006508079A5 - - Google Patents
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- JP2006508079A5 JP2006508079A5 JP2004543449A JP2004543449A JP2006508079A5 JP 2006508079 A5 JP2006508079 A5 JP 2006508079A5 JP 2004543449 A JP2004543449 A JP 2004543449A JP 2004543449 A JP2004543449 A JP 2004543449A JP 2006508079 A5 JP2006508079 A5 JP 2006508079A5
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| CN103724304B (zh) * | 2013-12-24 | 2016-08-17 | 定陶县友帮化工有限公司 | 5-溴苯并呋喃的制备方法 |
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Family Cites Families (61)
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| US3115496A (en) * | 1963-05-13 | 1963-12-24 | Upjohn Co | Certain 3, 4-disubstituted-1, 2, 5-thiadiazole-1, 1-dioxides and their preparation |
| DE1669798A1 (de) | 1966-07-28 | 1971-08-26 | Huels Chemische Werke Ag | Verfahren zum Stabilisieren markomolekularer Polyacetale |
| CS214745B2 (en) * | 1976-08-28 | 1982-05-28 | Huels Chemische Werke Ag | Shaped and non-shaped products from plastic materials |
| FI76795C (fi) | 1979-09-04 | 1988-12-12 | Bristol Myers Co | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 3,4-disubstituerade 1,2,5-tiadiazol-1-oxider och -1,1-dioxider samt nya mellanprodukter. |
| DE3175201D1 (en) | 1980-04-30 | 1986-10-02 | Merck & Co Inc | Aminothiadiazoles as gastric secretion inhibitors |
| US4394508A (en) * | 1980-06-07 | 1983-07-19 | Bristol-Myers Company | Chemical compounds |
| US4510309A (en) * | 1981-03-03 | 1985-04-09 | Bristol-Myers Company | Histamine H2 -antagonists |
| IE53068B1 (en) | 1981-06-15 | 1988-05-25 | Merck & Co Inc | Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors |
| GB2124622A (en) | 1982-07-08 | 1984-02-22 | Glaxo Group Ltd | Thiadiazole derivatives |
| FI832519L (fi) * | 1982-07-12 | 1984-01-13 | Bristol Myers Co | Farmaceutiska foerfaranden och sammansaettningar |
| US4863936A (en) * | 1982-12-14 | 1989-09-05 | Smith Kline & French Laboratories Limited | 3,5-Substituted-2-pyridyl-alkylaminocyclobutenediones having histamine h1 -antagonist activity |
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| JO1279B1 (en) * | 1982-12-23 | 1985-04-20 | جون ايف روبرت | Pyridine derivatives |
| DE3309655A1 (de) * | 1983-03-17 | 1984-09-20 | Bayer Ag, 5090 Leverkusen | 1,2,5-thiadiazol-1-oxide und 1,1-dioxide, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4497810A (en) * | 1983-10-14 | 1985-02-05 | Merck & Co., Inc. | Thiatriazine dioxides as gastric anti-secretory agents |
| US4562184A (en) * | 1984-04-02 | 1985-12-31 | Merck & Co., Inc. | Substituted-aminohydroxypropoxy-thiadiazoles, β-blocking compositions and use |
| JPS60255756A (ja) * | 1984-06-01 | 1985-12-17 | Ikeda Mohandou:Kk | アミノアルキルフエノキシ誘導体 |
| GB8501535D0 (en) * | 1985-01-22 | 1985-02-20 | Smith Kline French Lab | Chemical compounds |
| US4978665A (en) | 1987-01-20 | 1990-12-18 | Nissan Chemical Industries Ltd. | 3(2H)pyridazinone, and antagonistic agent against SRS-A containing it |
| JPH02256668A (ja) | 1988-12-20 | 1990-10-17 | Nissan Chem Ind Ltd | ピリダジノン誘導体 |
| US5206252A (en) * | 1992-05-08 | 1993-04-27 | American Home Products Corporation | Thiadiazolyl-amino derivatives of benzopyrans and indanes |
| GB9312210D0 (en) | 1993-06-14 | 1993-07-28 | Smithkline Beecham Plc | Chemical compounds |
| US5354763A (en) * | 1993-11-17 | 1994-10-11 | American Home Products Corporation | Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones |
| US5506252A (en) * | 1993-11-17 | 1996-04-09 | American Home Products Corporation | Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones |
| US5550139A (en) * | 1994-01-03 | 1996-08-27 | The Wichita State University | Serine protease inhibitors |
| US5466712A (en) | 1994-11-04 | 1995-11-14 | American Home Products Corporation | Substituted n-aryl-1,2-diaminocyclobutene-3,4-diones |
| JPH10509145A (ja) | 1994-11-16 | 1998-09-08 | アメリカン・ホーム・プロダクツ・コーポレイション | ジアミノシクロブテン−3,4−ジオン |
| US5494925A (en) * | 1994-12-02 | 1996-02-27 | Sterling Winthrop Inc. | 2-heterocyclyloxymethyl and 2-heterocyclylthiomethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxides and compositions and method of use thereof |
| US5958957A (en) * | 1996-04-19 | 1999-09-28 | Novo Nordisk A/S | Modulators of molecules with phosphotyrosine recognition units |
| IL131004A0 (en) * | 1997-01-23 | 2001-01-28 | Smithkline Beecham Corp | Il-8 receptor antagonists |
| AU6250298A (en) | 1997-01-30 | 1998-08-25 | American Home Products Corporation | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones |
| US5840764A (en) * | 1997-01-30 | 1998-11-24 | American Home Products Corporation | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones |
| AR015425A1 (es) * | 1997-09-05 | 2001-05-02 | Smithkline Beecham Corp | Compuestos de benzotiazol, composicion farmaceutica que los contiene, su uso en la manufactura de un medicamento, procedimiento para su preparacion,compuestos intermediarios y procedimiento para su preparacion |
| EP1117633B1 (en) | 1998-10-02 | 2002-09-18 | Neurosearch A/S | Diaminocyclobutene-3,4-dione derivatives, their preparation and use |
| ATE284387T1 (de) | 1998-10-08 | 2004-12-15 | Smithkline Beecham Plc | 3-(3-chloro-4-hydroxyphenylamino)-4-(2- nitrophenyl)-1h-pyrrol-2,5-dion als glykogen synthase kinase-3 inhibitor (gsk-3) |
| US6376555B1 (en) * | 1998-12-04 | 2002-04-23 | American Home Products Corporation | 4-substituted-3-substituted-amino-cyclobut-3-ene-1,2-diones and analogs thereof as novel potassium channel openers |
| WO2000035855A1 (en) | 1998-12-14 | 2000-06-22 | American Home Products Corporation | 3,4-diamino-3-cyclobutene-1,2-dione derivatives which inhibit leukocyte adhesion mediated by vla-4 |
| US6420396B1 (en) * | 1998-12-16 | 2002-07-16 | Beiersdorf Ag | Biphenyl and biphenyl-analogous compounds as integrin antagonists |
| NZ512339A (en) | 1998-12-16 | 2003-03-28 | Bayer Ag | New biphenyl and biphenyl-analogous compounds as integrin antagonists |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| CO5190696A1 (es) | 1999-06-16 | 2002-08-29 | Smithkline Beecham Corp | Antagonistas de los receptores il-8 |
| US6586446B1 (en) | 1999-10-15 | 2003-07-01 | Bristol-Myers Squibb Company | Bicyclic and tricyclic amines as modulators of chemokine receptor activity |
| CA2384240A1 (en) | 1999-10-15 | 2001-04-26 | Dean A. Wacker | Benzylcycloalkyl amines as modulators of chemokine receptor activity |
| AU2001243351A1 (en) | 2000-03-01 | 2001-09-12 | Smith Kline Beecham Corporation | Il-8 receptor antagonists |
| AR033803A1 (es) * | 2000-03-01 | 2004-01-07 | Smithkline Beecham Corp | Compuestos de dianilino escuarano, composiciones farmaceuticas que los comprenden, y el uso de los mismos en la fabricacion de medicamentos para tratar enfermedades mediadas por quimioquinas |
| AU2001245724A1 (en) | 2000-03-14 | 2001-09-24 | Smith Kline Beecham Corporation | Il-8 receptor antagonists |
| HUP0302382A3 (en) * | 2000-05-30 | 2004-09-28 | Smithkline Beecham Corp | Il-8 receptor antagonists and pharmaceutical compositions containing them |
| US6395762B1 (en) * | 2000-07-17 | 2002-05-28 | American Home Products Corporation | Phenyl amino squarate and thiadiazole dioxide beta-3 adrenergic receptor agonists |
| ATE419845T1 (de) * | 2001-01-16 | 2009-01-15 | Smithkline Beecham Corp | Il-8-rezeptor-antagonisten |
| ATE346043T1 (de) * | 2001-01-16 | 2006-12-15 | Smithkline Beecham Corp | Il-8-rezeptorantagonisten |
| CA2436351A1 (en) * | 2001-02-02 | 2002-10-03 | Schering Corporation | 3,4-di-substituted cyclobutene-1, 2-diones as cxc chemokine receptor antagonists |
| US20030204085A1 (en) * | 2001-02-02 | 2003-10-30 | Taveras Arthur G. | 3, 4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor antagonists |
| DK1381590T3 (da) | 2001-04-16 | 2007-10-22 | Schering Corp | 3,4-disubstituerede cyclobuten-1,2-dioner som CXC-kemokinreceptorligander |
| US7132445B2 (en) * | 2001-04-16 | 2006-11-07 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| US6903131B2 (en) * | 2001-10-12 | 2005-06-07 | Schering Corporation | 3,4-di-substituted maleimide compounds as CXC chemokine receptor antagonists |
| US6878709B2 (en) * | 2002-01-04 | 2005-04-12 | Schering Corporation | 3,4-di-substituted pyridazinediones as CXC chemokine receptor antagonists |
| WO2003080053A1 (en) * | 2002-03-18 | 2003-10-02 | Schering Corporation | Combination treatments for chemokine-mediated diseases |
| DE60326080D1 (en) * | 2002-10-09 | 2009-03-19 | Schering Corp | Thiadiazoldioxide und thiadiazoloxide als cxc- und cc-chemokinrezeptor liganden |
| ATE406356T1 (de) * | 2003-12-19 | 2008-09-15 | Schering Corp | Thiadiazole als cxc- und cc- chemokinrezeptorliganden |
| TW200530231A (en) * | 2003-12-22 | 2005-09-16 | Schering Corp | Isothiazole dioxides as CXC-and CC-chemokine receptor ligands |
-
2003
- 2003-10-07 DE DE60326080T patent/DE60326080D1/de not_active Expired - Lifetime
- 2003-10-07 CA CA002501535A patent/CA2501535A1/en not_active Abandoned
- 2003-10-07 CN CN2003801051392A patent/CN1720240B/zh not_active Expired - Fee Related
- 2003-10-07 AU AU2003288922A patent/AU2003288922A1/en not_active Abandoned
- 2003-10-07 PE PE2003001019A patent/PE20040570A1/es not_active Application Discontinuation
- 2003-10-07 EP EP03781311A patent/EP1551818B1/en not_active Expired - Lifetime
- 2003-10-07 ES ES03781311T patent/ES2321186T3/es not_active Expired - Lifetime
- 2003-10-07 MY MYPI20033827A patent/MY139601A/en unknown
- 2003-10-07 WO PCT/US2003/031707 patent/WO2004033440A1/en not_active Ceased
- 2003-10-07 AT AT03781311T patent/ATE422203T1/de not_active IP Right Cessation
- 2003-10-07 MX MXPA05003867A patent/MXPA05003867A/es not_active Application Discontinuation
- 2003-10-07 JP JP2004543449A patent/JP4664074B2/ja not_active Expired - Fee Related
- 2003-10-07 US US10/680,393 patent/US20040186142A1/en not_active Abandoned
- 2003-10-08 AR ARP030103663A patent/AR043052A1/es unknown
- 2003-10-08 TW TW092127957A patent/TW200413342A/zh unknown
-
2007
- 2007-01-09 US US11/651,128 patent/US7691856B2/en not_active Expired - Fee Related
-
2010
- 2010-09-02 JP JP2010197184A patent/JP2010270151A/ja not_active Withdrawn
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