KR101255356B1 - 염증 및 면역 질병의 치료를 위한 ccr1 길항물질로서사용하기 위한 1-아릴-4-치환된 피페라진 유도체 - Google Patents

염증 및 면역 질병의 치료를 위한 ccr1 길항물질로서사용하기 위한 1-아릴-4-치환된 피페라진 유도체 Download PDF

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KR101255356B1
KR101255356B1 KR1020047020177A KR20047020177A KR101255356B1 KR 101255356 B1 KR101255356 B1 KR 101255356B1 KR 1020047020177 A KR1020047020177 A KR 1020047020177A KR 20047020177 A KR20047020177 A KR 20047020177A KR 101255356 B1 KR101255356 B1 KR 101255356B1
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alkyl
group
haloalkyl
chloro
compound
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KR20050042754A (ko
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앤드류 엠 케이 펜넬
제임즈 비 애겐
제이 제이 킴 라이트
수브하브라타 센
브라이언 이 맥매스터
대니얼 조지프 다이라기
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케모센트릭스, 인크.
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KR1020047020177A 2002-06-12 2003-06-11 염증 및 면역 질병의 치료를 위한 ccr1 길항물질로서사용하기 위한 1-아릴-4-치환된 피페라진 유도체 Expired - Fee Related KR101255356B1 (ko)

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US45371102P 2002-06-12 2002-06-12
US60/453,711 2002-06-12
PCT/US2003/018660 WO2003105853A1 (en) 2002-06-12 2003-06-11 1-aryl-4-substituted piperazines derivatives for use as ccr1 antagonists for the treatment of inflammation and immune disorders

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KR20050042754A KR20050042754A (ko) 2005-05-10
KR101255356B1 true KR101255356B1 (ko) 2013-04-17

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EP (1) EP1531822B1 (cg-RX-API-DMAC7.html)
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Families Citing this family (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003236500B9 (en) 2002-06-12 2009-07-02 Chemocentryx, Inc. 1-aryl-4-substituted piperazine derivatives for use as CCR1 antagonists for the treatment of inflammation and immune disorders
US7589199B2 (en) 2002-06-12 2009-09-15 Chemocentryx, Inc. Substituted piperazines
US7842693B2 (en) * 2002-06-12 2010-11-30 Chemocentryx, Inc. Substituted piperazines
US20050256130A1 (en) * 2002-06-12 2005-11-17 Chemocentryx, Inc. Substituted piperazines
JP4960085B2 (ja) * 2003-03-19 2012-06-27 エクセリクシス, インク. Tie−2モジュレータと使用方法
US7754711B2 (en) * 2003-07-30 2010-07-13 Xenon Pharmaceuticals Inc. Pyridazine derivatives and their use as therapeutic agents
AU2011265309B2 (en) * 2003-11-21 2014-06-05 Array Biopharma, Inc. AKT protein kinase inhibitors
PH12012501891A1 (en) 2003-11-21 2013-09-02 Array Biopharma Inc Akt protein kinase inhibitors
CN100542534C (zh) * 2003-12-09 2009-09-23 凯莫森特里克斯股份有限公司 取代的哌嗪
GB0401269D0 (en) * 2004-01-21 2004-02-25 Astrazeneca Ab Compounds
US7479496B2 (en) 2004-02-19 2009-01-20 Bristol-Myers Squibb Company Substituted spiro azabicyclics as modulators of chemokine receptor activity
US7381738B2 (en) 2004-02-19 2008-06-03 Bristol-Myers Squibb Company Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity
US7288563B2 (en) 2004-02-19 2007-10-30 Bristol-Myers Squibb Company Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity
US7230022B2 (en) 2004-02-19 2007-06-12 Bristol-Myers Squibb Company Substituted fused bicyclic amines as modulators of chemokine receptor activity
US7435831B2 (en) * 2004-03-03 2008-10-14 Chemocentryx, Inc. Bicyclic and bridged nitrogen heterocycles
JP4845873B2 (ja) * 2004-03-03 2011-12-28 ケモセントリックス インコーポレーティッド 二環式および架橋した窒素複素環
RU2006140687A (ru) * 2004-06-18 2008-07-27 Ньюросерч А/С (DK) Новые алкил-замещенные производные пиперазина и их применение в качестве ингибиторов обратного захвата моноаминовых нейротрансмиттеров
PE20060484A1 (es) * 2004-07-14 2006-07-06 Ucb Farchim Sa Preparaciones farmaceuticas liquidas que comprenden un compuesto de benzhidril piperizina
KR101220615B1 (ko) 2004-07-26 2013-01-11 메르크 세로노 에스.에이. N-히드록시아미드 유도체 및 그의 용도
CA2580860A1 (en) 2004-09-20 2006-03-30 Xenon Pharmaceuticals Inc. Pyridine derivatives for inhibiting human stearoyl-coa-desaturase
US7482353B2 (en) 2005-06-15 2009-01-27 Applied Biosystems Inc. Compositions and methods pertaining to PNA synthons and oligomers comprising a universal base
US7777035B2 (en) * 2005-06-22 2010-08-17 Chemocentryx, Inc. Azaindazole compounds and methods of use
SI1906965T1 (sl) * 2005-06-22 2015-09-30 Chemocentryx, Inc. Azaindolne spojine in postopki uporabe
US7790726B2 (en) * 2005-08-16 2010-09-07 Chemocentryx, Inc. Monocyclic and bicyclic compounds and methods of use
WO2007073432A2 (en) * 2005-10-11 2007-06-28 Chemocentryx, Inc. Piperidine derivatives and methods of use
EP1847543A1 (de) 2006-04-19 2007-10-24 Boehringer Ingelheim Pharma GmbH & Co. KG Dihydrothienopyrimidine zur Behandlung von entzündlichen Erkrankungen
WO2007146230A2 (en) * 2006-06-14 2007-12-21 Merck & Co., Inc. Non-nucleoside reverse transcriptase inhibitors
AR061481A1 (es) 2006-06-16 2008-08-27 Lundbeck & Co As H Compuestos con actividad combinada sobre sert, 5-ht3 y 5-ht1a
US20090252779A1 (en) * 2006-06-22 2009-10-08 Chemocentryx, Inc. Azaindazole compounds and methods of use
MX2009012567A (es) * 2007-05-22 2010-02-17 Chemocentryx Inc 3-(imidazolil)-pirazolo[3,4-b]piridinas.
US8536198B2 (en) 2007-07-24 2013-09-17 Bristol-Myers Squibb Company Piperidine derivatives as modulators of chemokine receptor activity
CA2722923C (en) 2008-04-29 2016-08-02 Boehringer Ingelheim International Gmbh Indazole compounds as ccr1 receptor antagonists
ES2392485T3 (es) * 2008-04-30 2012-12-11 Bayer Cropscience Ag Ésteres y tioésteres de ácido tiazol-4-carboxílico como agentes fitoprotectores
EP2297112B1 (en) 2008-05-06 2013-04-03 Boehringer Ingelheim International GmbH Pyrazole compounds as ccr1 antagonists
TWI433838B (zh) 2008-06-25 2014-04-11 必治妥美雅史谷比公司 作為趨化因子受體活性調節劑之六氫吡啶衍生物
EP2323663B1 (en) 2008-09-11 2015-02-25 ChemoCentryx, Inc. 4-amino-3-(imidazolyl)-pyrazolo[3,4-d]pyrimidines
AP2739A (en) * 2008-09-26 2013-09-30 Boehringer Ingelheim Int Azaindazole compounds as CCRI receptor antagonists
CA2742306A1 (en) * 2008-11-03 2010-05-06 Chemocentryx, Inc. Compounds for the treatment of osteoporosis and cancers
EP2424840B1 (en) * 2009-04-27 2014-08-06 Boehringer Ingelheim International GmbH Cxcr3 receptor antagonists
US8362249B2 (en) * 2009-04-27 2013-01-29 Boehringer Ingelheim International Gmbh CXCR3 receptor antagonists
PE20121433A1 (es) 2009-10-21 2012-11-10 Boehringer Ingelheim Int Compuestos de indazol y pirazolopiridina como antagonistas del receptor de ccr1
US8927550B2 (en) 2009-10-27 2015-01-06 Boehringer Ingelheim International Gmbh Heterocyclic compounds as CCR1 receptor antagonists
JP2013517281A (ja) * 2010-01-13 2013-05-16 テンペロ、ファーマシューティカルズ、インコーポレイテッド 化合物及び方法
EP2563787B1 (en) 2010-04-30 2014-11-26 Boehringer Ingelheim International GmbH Azaindazole amide compounds as ccr1 receptor antagonists
JP5684406B2 (ja) 2010-12-23 2015-03-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ccr1受容体アンタゴニストとしてのピラゾロピペリジン化合物
US20140329809A1 (en) 2011-10-28 2014-11-06 Galderma Research & Development New leukocyte infiltrate markers for rosacea and uses thereof
US8822464B2 (en) 2011-11-28 2014-09-02 Boehringer Ingelheim International Gmbh N-aryl-piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors
US8741892B2 (en) 2011-12-05 2014-06-03 Boehringer Ingelheim International Gmbh Compounds
US8642774B2 (en) 2011-12-08 2014-02-04 Boehringer Ingelheim International Gmbh Compounds
US8846948B2 (en) 2011-12-13 2014-09-30 Boehringer Ingelheim International Gmbh Compounds
US8796467B2 (en) 2011-12-13 2014-08-05 Boehringer Ingelheim International Gmbh Compounds
US8716277B2 (en) 2011-12-14 2014-05-06 Boehringer Ingelheim International Gmbh Substituted imidazole compounds useful as positive allosteric modulators of mGlu5 receptor activity
US8883789B2 (en) 2011-12-14 2014-11-11 Boehringer Ingelheim International Gmbh Piperazine derivatives and their use as positive allosteric modulators of mGluR5 receptors
US8937176B2 (en) 2011-12-14 2015-01-20 Boehringer Ingelheim International Gmbh Compounds
US8889677B2 (en) 2012-01-17 2014-11-18 Boehringer Ingellheim International GmbH Substituted triazoles useful as mGlu5 receptor modulators
KR102295416B1 (ko) 2013-07-22 2021-08-30 이도르시아 파마슈티컬스 리미티드 1-(피페라진-1-일)-2-([1,2,4]트리아졸-1-일)-에타논 유도체
AR099789A1 (es) 2014-03-24 2016-08-17 Actelion Pharmaceuticals Ltd Derivados de 8-(piperazin-1-il)-1,2,3,4-tetrahidro-isoquinolina
AR103399A1 (es) 2015-01-15 2017-05-10 Actelion Pharmaceuticals Ltd Derivados de (r)-2-metil-piperazina como moduladores del receptor cxcr3
SI3245203T1 (sl) 2015-01-15 2019-03-29 Idorsia Pharmaceuticals Ltd Derivati hiroksialkil-piperazina kot modulatorji receptorja CXCR3
SG11201811023UA (en) * 2016-06-23 2019-01-30 St Jude Childrens Res Hospital Small molecule modulators of pantothenate kinases
IL275658B2 (en) 2017-12-27 2024-04-01 St Jude Childrens Res Hospital Inc Small molecule modulators of pantothenate kinases
WO2019133632A1 (en) 2017-12-27 2019-07-04 St. Jude Children's Research Hospital Methods of treating disorders associated with castor
CN114206338B (zh) 2019-07-10 2025-12-12 凯莫森特里克斯股份有限公司 作为pd-l1抑制剂的二氢化茚类
WO2021039961A1 (ja) * 2019-08-30 2021-03-04 大日本住友製薬株式会社 縮環ピラゾール誘導体
US11713307B2 (en) 2019-10-16 2023-08-01 Chemocentryx, Inc. Heteroaryl-biphenyl amides for the treatment of PD-L1 diseases
PH12022550877A1 (en) 2019-10-16 2023-03-27 Chemocentryx Inc Heteroaryl-biphenyl amines for the treatment of pd-l1 diseases

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002014314A2 (en) * 2000-08-14 2002-02-21 Ortho Mcneil Pharmaceutical, Inc. Substituted pyrazoles
US20020022624A1 (en) * 2000-07-13 2002-02-21 Kevin Dinnell Azaindole derivatives and their use as therapeutic agents

Family Cites Families (89)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE663344A (cg-RX-API-DMAC7.html) * 1964-05-04
US3362956A (en) * 1965-08-19 1968-01-09 Sterling Drug Inc 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines
US3491098A (en) * 1967-05-29 1970-01-20 Sterling Drug Inc 1-((imidazolyl)-lower-alkyl)-4-substituted-piperazines
US3778433A (en) * 1969-04-18 1973-12-11 Sumitomo Chemical Co Process for producing benzodiazepine derivatives
DE2247187A1 (de) * 1972-09-26 1974-03-28 Bayer Ag Imidazolylessigsaeureamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
JPS5944313B2 (ja) * 1974-11-26 1984-10-29 中外製薬株式会社 インダゾ−ル誘導体の製法
US3994890A (en) * 1974-01-31 1976-11-30 Chugai Seiyaku Kabushiki Kaisha 1-Aminoalkyl, 3-phenyl indazoles
US4174393A (en) * 1975-07-09 1979-11-13 Duphar International Research B.V. 1,3,4-Substituted pyrazoline derivatives
US4166452A (en) * 1976-05-03 1979-09-04 Generales Constantine D J Jr Apparatus for testing human responses to stimuli
US4256108A (en) * 1977-04-07 1981-03-17 Alza Corporation Microporous-semipermeable laminated osmotic system
US4243619A (en) * 1978-03-31 1981-01-06 Union Carbide Corporation Process for making film from low density ethylene hydrocarbon copolymer
US4310429A (en) * 1978-06-19 1982-01-12 The B. F. Goodrich Company Stabilized polymers, novel stabilizers, and synthesis thereof
DE2842539A1 (de) * 1978-09-29 1980-04-10 Bayer Ag 1-isocyanato-anthrachinone
US4265874A (en) 1980-04-25 1981-05-05 Alza Corporation Method of delivering drug with aid of effervescent activity generated in environment of use
DE3132915A1 (de) * 1981-08-20 1983-03-03 Kali-Chemie Pharma Gmbh, 3000 Hannover 1,5-diphenylpyrazolin-3-on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JPS5852256A (ja) * 1981-09-24 1983-03-28 Nippon Nohyaku Co Ltd 置換又は非置換脂肪酸アミド誘導体及びその塩類
DE3306771A1 (de) * 1983-02-25 1984-08-30 Bayer Ag, 5090 Leverkusen Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
US4547505A (en) 1983-03-25 1985-10-15 Degussa Aktiengesellschaft N-Phenyl-N-'-cycloalkylalkanoylpiperazine useful as analgetics and process for its production
US4562189A (en) * 1984-10-09 1985-12-31 American Cyanamid Company Pyrazolylpiperazines
DE3442860A1 (de) * 1984-11-24 1986-05-28 Kali-Chemie Pharma Gmbh, 3000 Hannover 5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3- on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
IE61724B1 (en) * 1986-02-27 1994-11-30 Duphar Int Res Aryl-subsituted (N-piperidinyl)methyl-and(N-piperazinyl)methylazoles having antipsychotic properties
IL85700A0 (en) * 1987-03-24 1988-08-31 Takeda Chemical Industries Ltd 1,4-disubstituted piperazine compounds,their production and use
US4997836A (en) * 1988-11-11 1991-03-05 Takeda Chemical Industries, Ltd. Trisubstituted piperazine compounds, their production and use
EP0385043A1 (en) * 1989-02-28 1990-09-05 Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. (Faes) New derivatives of 4-substituted piperazines
US5215989A (en) * 1989-12-08 1993-06-01 Merck & Co., Inc. Nitrogen-containing heterocyclic compounds as class III antiarrhythmic agents
FR2672052B1 (fr) * 1991-01-28 1995-05-24 Esteve Labor Dr Derives d'aryl (ou heteroaryl)-piperazinyl-alkyl-azoles, leur preparation et leur application en tant que medicaments.
GB9021453D0 (en) * 1990-10-03 1990-11-14 Wyeth John & Brother Ltd Piperazine derivatives
GB9021535D0 (en) * 1990-10-03 1990-11-14 Wyeth John & Brother Ltd Piperazine derivatives
FR2673628B1 (fr) * 1991-03-07 1993-07-09 Esteve Labor Dr Procede de preparation de derives d'aryl (ou heteroaryl)-piperazinyl-butyl-azoles.
GB9305623D0 (en) * 1993-03-18 1993-05-05 Merck Sharp & Dohme Therapeutic agents
US5681954A (en) * 1993-05-14 1997-10-28 Daiichi Pharmaceutical Co., Ltd. Piperazine derivatives
US5464788A (en) * 1994-03-24 1995-11-07 Merck & Co., Inc. Tocolytic oxytocin receptor antagonists
US5486534A (en) * 1994-07-21 1996-01-23 G. D. Searle & Co. 3,4-substituted pyrazoles for the treatment of inflammation
US5607936A (en) * 1994-09-30 1997-03-04 Merck & Co., Inc. Substituted aryl piperazines as neurokinin antagonists
US5719156A (en) * 1995-05-02 1998-02-17 Schering Corporation Piperazino derivatives as neurokinin antagonists
WO1997003067A1 (en) * 1995-07-13 1997-01-30 Knoll Aktiengesellschaft Piperazine derivatives as therapeutic agents
GB9518552D0 (en) 1995-09-11 1995-11-08 Fujisawa Pharmaceutical Co New heterocyclic compounds
US5760028A (en) * 1995-12-22 1998-06-02 The Dupont Merck Pharmaceutical Company Integrin receptor antagonists
US5646151A (en) * 1996-03-08 1997-07-08 Adolor Corporation Kappa agonist compounds and pharmaceutical formulations thereof
JP4176148B2 (ja) 1996-05-20 2008-11-05 帝人ファーマ株式会社 ジアリールアルキル環状ジアミン誘導体およびその治療薬としての使用
US5760225A (en) * 1996-11-15 1998-06-02 Neurogen Corporation Certain pyrazole derivatives as corticotropin-releasing factor receptor CRF1 specific ligands
EP0955293B1 (en) * 1996-12-03 2003-03-19 Banyu Pharmaceutical Co., Ltd. Urea derivatives
AU5522498A (en) 1996-12-13 1998-07-03 Merck & Co., Inc. Substituted aryl piperazines as modulators of chemokine receptor activity
PT971713E (pt) * 1997-03-03 2003-09-30 Eisai Co Ltd Utilizacao de inibidores da colinesterase para tratamento de desordens da atencao
US6979686B1 (en) * 2001-12-07 2005-12-27 Pharmacia Corporation Substituted pyrazoles as p38 kinase inhibitors
US6207665B1 (en) * 1997-06-12 2001-03-27 Schering Aktiengesellschaft Piperazine derivatives and their use as anti-inflammatory agents
US5968938A (en) * 1997-06-18 1999-10-19 Merck & Co., Inc. Piperazine oxytocin receptor antagonists
ES2125206B1 (es) * 1997-07-21 1999-11-16 Esteve Labor Dr Derivados de acil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos.
GB9716657D0 (en) 1997-08-07 1997-10-15 Zeneca Ltd Chemical compounds
EP1009405A4 (en) 1997-08-28 2001-05-09 Merck & Co Inc PAYRROLIDINE AND PIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
JP2001519413A (ja) * 1997-10-09 2001-10-23 オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド 良性の前立腺過形成の治療に有用な複素環化合物およびそれらの中間体
CN100418951C (zh) 1997-11-18 2008-09-17 帝人医药株式会社 环胺衍生物及其作为药物的用途
ZA9811576B (en) 1997-12-19 2000-06-19 Takeda Chemical Industries Ltd Anilide derivative, production and use thereof.
US6433165B1 (en) 1998-01-21 2002-08-13 Millennium Pharmaceuticals, Inc. Chemokine receptor antagonists and methods of use therefor
DK1049700T3 (da) * 1998-01-21 2006-02-20 Millennium Pharm Inc Kemokinreceptorantagonister og fremgangsmåder til anvendelse deraf
DE69920888T2 (de) * 1998-03-27 2006-02-02 Bristol-Myers Squibb Pharma Co. Disubstituierte pyrazoline und triazoline als faktor xa inhibitoren
US6492375B2 (en) * 1998-06-30 2002-12-10 Neuromed Technologies, Inc. Partially saturated calcium channel blockers
US6288083B1 (en) * 1998-09-04 2001-09-11 Millennium Pharmaceuticals, Inc. Chemokine receptor antagonists and methods of use therefor
HUP0104364A2 (hu) 1998-11-20 2002-04-29 F. Hoffmann-La Roche Ag. Pirrolidinszármazékok, CCR-3 receptor antagonisták és ezeket tartalmazó gyógyszerkészítmények
GB9902452D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
GB9902459D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
GB9902461D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
GB9902453D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
JP3533134B2 (ja) 1999-02-15 2004-05-31 三井化学株式会社 フッ素化剤及びその製法と使用
GB9905010D0 (en) * 1999-03-04 1999-04-28 Merck Sharp & Dohme Therapeutic agents
AU2942000A (en) 1999-03-11 2000-09-28 Banyu Pharmaceutical Co., Ltd. Novel piperidine derivatives
WO2000069815A1 (en) 1999-05-13 2000-11-23 Teijin Limited Ureido-substituted cyclic amine derivatives and their use as drug
ES2225143T3 (es) 1999-05-14 2005-03-16 Bristol-Myers Squibb Pharma Research Labs, Inc. Derivados de aminas ciclicas y sus usos.
US6492516B1 (en) 1999-05-14 2002-12-10 Merck & Co., Inc. Compounds having cytokine inhibitory activity
EP1246795B1 (en) * 2000-01-13 2007-10-31 Amgen Inc. Antibacterial agents
AU2001250404A1 (en) * 2000-03-27 2001-10-08 Basf Aktiengesellschaft Use of dopamine-d3 receptor ligands for the treatment of diseases of the central nervous system
KR20020084273A (ko) * 2000-03-31 2002-11-04 화이자 프로덕츠 인코포레이티드 신규한 피페라진 유도체
US20020045613A1 (en) * 2000-04-27 2002-04-18 Heinz Pauls 1-aroyl-piperidinyl benzamidines
WO2001082930A1 (en) * 2000-05-03 2001-11-08 Tularik Inc. Pyrazole antimicrobial agents
PE20020665A1 (es) * 2000-06-15 2002-08-14 Pharmacia Corp ACIDO CICLOALQUIL FENIL ALCANOICO COMO ANTAGONISTA DE INTEGRINAS OVß3
JP2004525071A (ja) 2000-07-20 2004-08-19 ニューロジェン コーポレイション カプサイシン受容体リガンド
YU30603A (sh) * 2000-10-19 2006-05-25 Pfizer Products Inc. Derivati premošćenog piperazina
US6451399B1 (en) * 2001-02-05 2002-09-17 Daniel G. Boyce Display mat
EP1368354A1 (en) 2001-03-07 2003-12-10 Pfizer Products Inc. Modulators of chemokine receptor activity
CN1157388C (zh) * 2001-05-29 2004-07-14 北京大学 哌嗪基二硫代甲酸酯类化合物,它们的制备方法和在抗肿瘤药物中的应用
ES2180456B1 (es) * 2001-07-20 2004-05-01 Laboratorios S.A.L.V.A.T., S.A. Isoxazoles sustituidos y su utilizacion como antibioticos.
WO2003024450A1 (en) 2001-09-20 2003-03-27 Eisai Co., Ltd. Methods for treating prion diseases
AU2002351731A1 (en) * 2001-12-14 2003-06-30 Novo Nordisk A/S Compounds and uses thereof for decreasing activity of hormone-sensitive lipase
NO315724B1 (no) * 2001-12-20 2003-10-13 Sten Hellvik Datainnsamlingssystem for et fartöy
US20050256130A1 (en) 2002-06-12 2005-11-17 Chemocentryx, Inc. Substituted piperazines
US7842693B2 (en) * 2002-06-12 2010-11-30 Chemocentryx, Inc. Substituted piperazines
AU2003236500B9 (en) * 2002-06-12 2009-07-02 Chemocentryx, Inc. 1-aryl-4-substituted piperazine derivatives for use as CCR1 antagonists for the treatment of inflammation and immune disorders
PA8575901A1 (es) 2002-07-18 2004-07-20 Pfizer Prod Inc Derivados de piperidina novedosos
CA2494114A1 (en) * 2002-08-02 2004-02-12 Argenta Discovery Limited Substituted thienyl-hydroxamic acids as histone deacetylase inhibitors

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020022624A1 (en) * 2000-07-13 2002-02-21 Kevin Dinnell Azaindole derivatives and their use as therapeutic agents
WO2002014314A2 (en) * 2000-08-14 2002-02-21 Ortho Mcneil Pharmaceutical, Inc. Substituted pyrazoles

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