MXPA06013118A - Antagonistas de cxcr1 y cxcr2 de quimocina. - Google Patents
Antagonistas de cxcr1 y cxcr2 de quimocina.Info
- Publication number
- MXPA06013118A MXPA06013118A MXPA06013118A MXPA06013118A MXPA06013118A MX PA06013118 A MXPA06013118 A MX PA06013118A MX PA06013118 A MXPA06013118 A MX PA06013118A MX PA06013118 A MXPA06013118 A MX PA06013118A MX PA06013118 A MXPA06013118 A MX PA06013118A
- Authority
- MX
- Mexico
- Prior art keywords
- substituted
- unsubstituted
- group
- alkyl
- aryl
- Prior art date
Links
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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| MXPA06013118A true MXPA06013118A (es) | 2007-02-28 |
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| MXPA06013118A MXPA06013118A (es) | 2004-05-12 | 2005-05-11 | Antagonistas de cxcr1 y cxcr2 de quimocina. |
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| EP2009992B1 (en) * | 2006-04-21 | 2012-06-27 | GlaxoSmithKline LLC | Il-8 receptor antagonists |
| UA95480C2 (uk) * | 2006-06-08 | 2011-08-10 | Елі Ліллі Енд Компані | Заміщені карбоксаміди |
| JP2010504996A (ja) * | 2006-09-26 | 2010-02-18 | ケース ウエスタン リザーブ ユニバーシティ | サイトカインシグナリング |
| ATE484505T1 (de) * | 2006-11-23 | 2010-10-15 | Novartis Ag | 5-sulfanylmethylä1,2,4ütriazolä1,5-aüpyrimidin- - olderivate als cxcr2-antagonisten |
| EP2094697A1 (en) * | 2006-11-23 | 2009-09-02 | Novartis AG | 5-sulfanylmethyl-pyrazolo [1,5-a]pyrimidin-7-ol derivatives as cxcr2 antagonists |
| PL2116530T3 (pl) | 2007-02-26 | 2013-03-29 | Santen Pharmaceutical Co Ltd | Nowa pochodna pirolu zawierająca jako podstawniki grupę ureidową i grupę aminokarbonylową |
| WO2009026248A2 (en) * | 2007-08-17 | 2009-02-26 | The Government Of The United States, As Represented By The Secretary Of Health And Human Services, National Institutes Of Health, Office Of Technology Transfer | Hydrazide, amide, phthalimide and phthalhydrazide analogs as inhibitors of retroviral integrase |
| KR101039235B1 (ko) * | 2007-08-29 | 2011-06-07 | 메디포스트(주) | 제대혈 유래 간엽줄기세포를 포함하는 인터루킨-8 또는지알오-알파 발현 세포가 관련된 질병의 진단, 예방 또는치료용 조성물 |
| GB2455539B (en) * | 2007-12-12 | 2012-01-18 | Cambridge Entpr Ltd | Anti-inflammatory compositions and combinations |
| SG176464A1 (en) | 2008-05-09 | 2011-12-29 | Agency Science Tech & Res | Diagnosis and treatment of kawasaki disease |
| JP5716180B2 (ja) | 2008-11-11 | 2015-05-13 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 抗cxcr1組成物および方法 |
| JP5881705B2 (ja) * | 2010-09-03 | 2016-03-09 | フォーマ ティーエム, エルエルシー. | Namptの阻害のための新規化合物及び組成物 |
| WO2012172344A2 (en) * | 2011-06-13 | 2012-12-20 | Ith Immune Therapy Holdings | Treating conditions associated with sepsis |
| WO2013148370A1 (en) | 2012-03-30 | 2013-10-03 | Sloan-Kettering Institute For Cancer Research | S100a8/a9 as a diagnostic marker and a therapeutic target |
| WO2014062511A1 (en) * | 2012-10-15 | 2014-04-24 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| US8865723B2 (en) | 2012-10-25 | 2014-10-21 | Tetra Discovery Partners Llc | Selective PDE4 B inhibition and improvement in cognition in subjects with brain injury |
| WO2014205127A2 (en) | 2013-06-18 | 2014-12-24 | New York University | Cellular factors involved in the cytotoxicity of staphylococcus aureus leukocidins: novel therapeutic targets |
| WO2015054117A1 (en) * | 2013-10-08 | 2015-04-16 | Temple University-Of The Commonwealth System Of Higher Education | Functionalized furan-2-sulfonamides exhibiting endothelial lipase inhibition |
| US9763992B2 (en) | 2014-02-13 | 2017-09-19 | Father Flanagan's Boys' Home | Treatment of noise induced hearing loss |
| CA2961021C (en) | 2014-09-26 | 2022-08-02 | Shifa Biomedical Corporation | Anti-endothelial lipase compounds and methods of using the same in the treatment and/or prevention of cardiovascular diseases |
| WO2017040742A1 (en) * | 2015-09-04 | 2017-03-09 | Dow Agrosciences Llc | Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto |
| JP7092356B2 (ja) * | 2016-06-22 | 2022-06-28 | フーダン ユニヴァーシティ | ビアリール尿素誘導体またはそれらの塩、およびそれらの調製方法および使用 |
| US20190216790A1 (en) * | 2016-10-13 | 2019-07-18 | The Regents Of The University Of California | Methods for Treating Pruritis |
| EP3551034A1 (en) | 2016-12-07 | 2019-10-16 | Progenity, Inc. | Gastrointestinal tract detection methods, devices and systems |
| CA3045310A1 (en) | 2016-12-14 | 2018-06-21 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with a chemokine/chemokine receptor inhibitor |
| WO2020106704A2 (en) | 2018-11-19 | 2020-05-28 | Progenity, Inc. | Ingestible device for delivery of therapeutic agent to the gastrointestinal tract |
| CN121197633A (zh) | 2019-12-13 | 2025-12-26 | 比特比德科有限责任公司 | 用于将治疗剂递送至胃肠道的可摄取装置 |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3529247A1 (de) * | 1985-05-17 | 1986-11-20 | Bayer Ag, 5090 Leverkusen | Verwendung von thienylharnstoffen und -isoharnstoffen als leistungsfoerdernde mittel bei tieren, neue thienylharnstoffe und -isoharnstoffe und ihre herstellung |
| DE3785507T2 (de) * | 1986-07-31 | 1993-07-29 | Beecham Group Plc | Azabicyclische verbindungen, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung. |
| DE4412334A1 (de) * | 1994-04-11 | 1995-10-19 | Hoechst Ag | Substituierte N-Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US5780483A (en) * | 1995-02-17 | 1998-07-14 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| EP0809492A4 (en) | 1995-02-17 | 2007-01-24 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| WO1997049287A1 (en) | 1996-06-27 | 1997-12-31 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO1997049399A1 (en) | 1996-06-27 | 1997-12-31 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| EP0932405A4 (en) | 1996-06-27 | 2001-10-17 | Smithkline Beckman Corp | IL-8 RECEPTOR ANTAGONISTS |
| TR199802694T2 (xx) | 1996-06-27 | 1999-03-22 | Smithkline Beecham Corporation | IL-8 resept�r kar��tlar� |
| CZ425698A3 (cs) | 1996-06-27 | 1999-06-16 | Smithkline Beecham Corporation | Antagonista IL-8 receptoru |
| WO1998005329A1 (en) | 1996-08-06 | 1998-02-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| JP2002513384A (ja) | 1996-08-06 | 2002-05-08 | スミスクライン・ビーチャム・コーポレイション | Il―8受容体アンタゴニスト |
| WO1998005317A1 (en) | 1996-08-06 | 1998-02-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| AR008290A1 (es) | 1996-08-15 | 1999-12-29 | Smithkline Beecham Corp | Nuevos compuestos que contienen guanidina utiles como antagonistas de los receptores de il-8, composiciones farmaceuticas que los contienenprocedimiento para la preparacion de dichos compuestos y procedimiento para la preparacion de intermediarios. |
| WO1998006398A1 (en) | 1996-08-15 | 1998-02-19 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| JP2001527519A (ja) | 1996-08-15 | 2001-12-25 | スミスクライン・ビーチャム・コーポレイション | Il―8レセプターアンタゴニスト |
| EP0923373A4 (en) | 1996-08-15 | 2001-10-17 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGOISTS |
| JP2001501918A (ja) | 1996-08-21 | 2001-02-13 | スミスクライン・ビーチャム・コーポレイション | Il―8レセプターアンタゴニスト |
| KR20000070368A (ko) | 1997-01-23 | 2000-11-25 | 스튜어트 알. 수터, 스티븐 베네티아너, 피터 존 기딩스 | 인터루킨-8 수용체 길항제 |
| AR008331A1 (es) | 1997-01-23 | 1999-12-29 | Smithkline Beecham Corp | Compuestos antagonistas de un receptor de il-8, uso de los mismos para la fabricacion de medicamentos, procedimiento para su obtencion, composicionesfarmaceuticas que los contienen |
| AR015426A1 (es) | 1997-09-05 | 2001-05-02 | Smithkline Beecham Corp | Compuestos de benzotiazol antagonistas del receptor de il-8, composicion farmaceutica que los contiene, su uso para la manufactura de un medicamento,procedimiento para su preparacion, compuestos intermediarios y procedimiento para su preparacion |
| 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 |
| JP4437270B2 (ja) * | 1997-12-22 | 2010-03-24 | バイエル コーポレイション | 置換複素環式尿素を用いたrafキナーゼの阻害 |
| WO1999036070A1 (en) | 1998-01-20 | 1999-07-22 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| US6525069B1 (en) * | 1998-12-18 | 2003-02-25 | Bristol-Myers Squibb Pharma Co. | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| CO5200760A1 (es) * | 1999-06-16 | 2002-09-27 | Smithkline Beecham Corp | Antagonistas del receptor de la il-8 ceptor il-8 |
| PE20010321A1 (es) | 1999-06-16 | 2001-05-18 | Smithkline Beecham Corp | Antagonistas de los receptores de la il-8 |
| EP1202718A2 (en) * | 1999-07-21 | 2002-05-08 | Kadmus Pharmaceuticals, Inc. | Substituted guanidines for the treatment of cancer and pain |
| ES2208227T3 (es) * | 1999-12-03 | 2004-06-16 | Pfizer Products Inc. | Compuestos de heteroarilfenilpirazol como agentes antiinflamatorios/analgesicos. |
| EP1274413A4 (en) | 2000-03-01 | 2005-08-10 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| AU2001243351A1 (en) | 2000-03-01 | 2001-09-12 | Smith Kline Beecham Corporation | Il-8 receptor antagonists |
| AR031098A1 (es) | 2000-03-16 | 2003-09-10 | Smithkline Beecham Corp | Compuestos de hidroxifenil urea sustituidos con sulfonamidas, composiciones farmaceuticas que los comprenden, y uso de los mismos en la fabricacion de medicamentos para tratar una enfermedad mediada por una quimioquina |
| UY26627A1 (es) | 2000-03-24 | 2001-09-28 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
| CA2413421A1 (en) * | 2000-06-21 | 2001-12-27 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| PL367534A1 (en) | 2001-02-02 | 2005-02-21 | Schering Corporation | 3,4-di-substituted cyclobutene-1, 2-diones as cxc chemokine receptor antagonists |
| US20040106794A1 (en) * | 2001-04-16 | 2004-06-03 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| US7132445B2 (en) * | 2001-04-16 | 2006-11-07 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
| EP1270551A1 (en) * | 2001-06-26 | 2003-01-02 | Aventis Pharma Deutschland GmbH | Urea derivatives with antiproteolytic activity |
| AUPR738301A0 (en) * | 2001-08-30 | 2001-09-20 | Starpharma Limited | Chemotherapeutic agents |
| MXPA04003439A (es) | 2001-10-12 | 2004-07-08 | Schering Corp | Compuestos de maleimida 3,4 disustituidos como antagonistas de receptor de quimiocina cxc. |
| US6878709B2 (en) * | 2002-01-04 | 2005-04-12 | Schering Corporation | 3,4-di-substituted pyridazinediones as CXC chemokine receptor antagonists |
| BR0308739A (pt) * | 2002-03-18 | 2005-01-11 | Schering Corp | Tratamentos em combinação para doenças mediadas por quimiocina |
| EP1402888A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| ATE422203T1 (de) | 2002-10-09 | 2009-02-15 | Schering Corp | Thiadiazoldioxide und thiadiazoloxide als cxc- und cc-chemokinrezeptor liganden |
| JP4939229B2 (ja) * | 2003-12-19 | 2012-05-23 | シェーリング コーポレイション | Cxc−ケモカインレセプターリガンドおよびcc−ケモカインレセプターリガンドとしてのチアジアゾール |
| TW200530231A (en) * | 2003-12-22 | 2005-09-16 | Schering Corp | Isothiazole dioxides as CXC-and CC-chemokine receptor ligands |
| JP2009500328A (ja) * | 2005-06-29 | 2009-01-08 | シェーリング コーポレイション | Cxc−ケモカインレセプターリガンドとしての5,6−ジ−置換オキサジアゾロピラジンおよびチアジアゾロピラジン |
| EP1912971A2 (en) * | 2005-06-29 | 2008-04-23 | Shering Corporation | Di-substituted oxadiazoles as cxc-chemokine receptor ligands |
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2005
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- 2005-05-11 JP JP2007513317A patent/JP2007537272A/ja not_active Ceased
- 2005-05-11 EP EP05779979.3A patent/EP1745032B1/en not_active Expired - Lifetime
- 2005-05-11 US US11/126,977 patent/US7326729B2/en not_active Expired - Fee Related
- 2005-05-11 WO PCT/US2005/016507 patent/WO2005113534A2/en not_active Ceased
- 2005-05-11 CA CA002565519A patent/CA2565519A1/en not_active Abandoned
- 2005-05-11 AU AU2005245399A patent/AU2005245399A1/en not_active Abandoned
- 2005-05-11 MX MXPA06013118A patent/MXPA06013118A/es active IP Right Grant
- 2005-05-11 KR KR1020067023571A patent/KR20070011475A/ko not_active Withdrawn
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2006
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- 2006-11-09 IL IL179162A patent/IL179162A0/en unknown
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2007
- 2007-07-10 US US11/775,567 patent/US20070248594A1/en not_active Abandoned
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2011
- 2011-10-11 JP JP2011224353A patent/JP2012006982A/ja not_active Withdrawn
Also Published As
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| CA2565519A1 (en) | 2005-12-01 |
| CN1984899B (zh) | 2011-07-27 |
| ZA200609237B (en) | 2008-08-27 |
| EP1745032B1 (en) | 2013-07-31 |
| US20070248594A1 (en) | 2007-10-25 |
| JP2012006982A (ja) | 2012-01-12 |
| WO2005113534A3 (en) | 2006-10-26 |
| WO2005113534A2 (en) | 2005-12-01 |
| US20060014794A1 (en) | 2006-01-19 |
| CN1984899A (zh) | 2007-06-20 |
| US7326729B2 (en) | 2008-02-05 |
| EP1745032A2 (en) | 2007-01-24 |
| KR20070011475A (ko) | 2007-01-24 |
| JP2007537272A (ja) | 2007-12-20 |
| IL179162A0 (en) | 2007-03-08 |
| AU2005245399A1 (en) | 2005-12-01 |
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