CA2722139C - Carboxamide compounds for the treatment of metabolic disorders - Google Patents

Carboxamide compounds for the treatment of metabolic disorders Download PDF

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Publication number
CA2722139C
CA2722139C CA2722139A CA2722139A CA2722139C CA 2722139 C CA2722139 C CA 2722139C CA 2722139 A CA2722139 A CA 2722139A CA 2722139 A CA2722139 A CA 2722139A CA 2722139 C CA2722139 C CA 2722139C
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CA
Canada
Prior art keywords
alkyl
piperidin
substituted
phenyl
trifluoromethyl
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CA2722139A
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English (en)
French (fr)
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CA2722139A1 (en
Inventor
Jiaxin Yu
Hui Hong
Ihab S. Darwish
Xiang Xu
Rajinder Singh
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Rigel Pharmaceuticals Inc
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Rigel Pharmaceuticals Inc
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Publication of CA2722139A1 publication Critical patent/CA2722139A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Hydrogenated Pyridines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA2722139A 2008-04-23 2009-04-22 Carboxamide compounds for the treatment of metabolic disorders Active CA2722139C (en)

Applications Claiming Priority (17)

Application Number Priority Date Filing Date Title
US4739908P 2008-04-23 2008-04-23
US61/047,399 2008-04-23
US4899708P 2008-04-30 2008-04-30
US61/048,997 2008-04-30
US5403508P 2008-05-16 2008-05-16
US61/054,035 2008-05-16
US5493408P 2008-05-21 2008-05-21
US61/054,934 2008-05-21
US5885408P 2008-06-04 2008-06-04
US61/058,854 2008-06-04
US7816608P 2008-07-03 2008-07-03
US7820908P 2008-07-03 2008-07-03
US7818008P 2008-07-03 2008-07-03
US61/078,180 2008-07-03
US61/078,209 2008-07-03
US61/078,166 2008-07-03
PCT/US2009/041448 WO2009132136A1 (en) 2008-04-23 2009-04-22 Carboxamide compounds for the treatment of metabolic disorders

Publications (2)

Publication Number Publication Date
CA2722139A1 CA2722139A1 (en) 2009-10-29
CA2722139C true CA2722139C (en) 2017-04-11

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Family Applications (1)

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CA2722139A Active CA2722139C (en) 2008-04-23 2009-04-22 Carboxamide compounds for the treatment of metabolic disorders

Country Status (15)

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US (6) US8314107B2 (enExample)
EP (1) EP2276761B1 (enExample)
JP (2) JP5658138B2 (enExample)
KR (1) KR101662333B1 (enExample)
CN (4) CN106928211B (enExample)
AU (1) AU2009240643B2 (enExample)
BR (1) BRPI0911681B8 (enExample)
CA (1) CA2722139C (enExample)
EA (1) EA021119B1 (enExample)
ES (1) ES2552549T3 (enExample)
IL (1) IL208513A0 (enExample)
MX (1) MX2010011288A (enExample)
NZ (1) NZ588652A (enExample)
WO (1) WO2009132136A1 (enExample)
ZA (1) ZA201007127B (enExample)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008083124A1 (en) 2006-12-28 2008-07-10 Rigel Pharmaceuticals, Inc. N-substituted-heterocycloalkyloxybenzamide compounds and methods of use
JP5544296B2 (ja) 2007-11-16 2014-07-09 ライジェル ファーマシューティカルズ， インコーポレイテッド 代謝障害のためのカルボキサミド、スルホンアミド、およびアミン化合物
ES2553340T3 (es) * 2007-12-12 2015-12-07 Rigel Pharmaceuticals, Inc. Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos
JP5658138B2 (ja) 2008-04-23 2015-01-21 ライジェル ファーマシューティカルズ， インコーポレイテッド 代謝障害の処置のためのカルボキサミド化合物
US8273900B2 (en) 2008-08-07 2012-09-25 Novartis Ag Organic compounds
CN102365275B (zh) * 2009-01-28 2014-09-24 里格尔药品股份有限公司 羧酰胺化合物及其使用方法
WO2011123681A1 (en) 2010-03-31 2011-10-06 Rigel Pharmaceuticals, Inc. Methods for using carboxamide, sulfonamide and amine compounds
JPWO2011142359A1 (ja) * 2010-05-10 2013-07-22 日産化学工業株式会社 スピロ化合物及びアディポネクチン受容体活性化薬
KR101764952B1 (ko) 2010-07-29 2017-08-03 리겔 파마슈티칼스, 인크. Ａｍｐｋ-활성화 헤테로시클릭 화합물 및 그의 사용 방법
US9005909B2 (en) 2011-01-06 2015-04-14 Rigel Pharmaceuticals, Inc. Whole blood assay for measuring AMPK activation
US9120776B2 (en) 2011-09-22 2015-09-01 Takeda Pharmaceutical Company Limited Condensed heterocyclic compound
US9409884B2 (en) 2012-02-01 2016-08-09 Rigel Pharmaceuticals, Inc. 5- or 6-substituted benzofuran-2-carboxamide compounds and methods for using them
US8889730B2 (en) 2012-04-10 2014-11-18 Pfizer Inc. Indole and indazole compounds that activate AMPK
EP2970177A1 (en) 2013-03-15 2016-01-20 Pfizer Inc. Indole compounds that activate ampk
AU2014279240A1 (en) * 2013-06-10 2016-01-07 Astellas Pharma Inc. Bicyclic nitrogen-containing aromatic heterocyclic amide compound
US20160214967A1 (en) * 2013-09-30 2016-07-28 The University Of Tokyo Activator of adiponectin receptor
US20180183429A1 (en) * 2016-12-28 2018-06-28 Sirectifier Electronic Co., Ltd. Integrated series schottky diode rectifier
JP7065589B2 (ja) 2017-10-31 2022-05-12 株式会社明治 ＩＬ－１β血清濃度低下用発酵乳、ＣＸＣＬ１血清濃度低下用発酵乳、癌に伴うＩＬ－１βの過度な血清濃度上昇の抑制用発酵乳、または、癌に伴うＣＸＣＬ１の過度な血清濃度上昇の抑制用発酵乳
CN110372638B (zh) * 2018-04-13 2023-09-22 中国药科大学 哌嗪类ampk激动剂及其医药用途
CN110372574A (zh) * 2018-04-13 2019-10-25 中国药科大学 哌啶类ampk激动剂及其医药用途
KR102364681B1 (ko) 2020-04-10 2022-02-18 엘지전자 주식회사 디퓨저 및 이를 포함하는 헤어드라이어
CN116323608A (zh) 2020-05-19 2023-06-23 卡尔优普公司 Ampk活化剂
EP4172162A4 (en) 2020-06-26 2024-08-07 Kallyope, Inc. AMPK ACTIVATORS

Family Cites Families (86)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE316476B (enExample) 1960-10-14 1969-10-27 Beecham Group Ltd
US3035047A (en) 1961-09-25 1962-05-15 Yvon G Perron Phthalamido penicillins
EP0094744A1 (en) 1982-04-23 1983-11-23 Beecham Group Plc Azabicyclobenzamides, their preparation and their pharmaceutical compositions
AU1508183A (en) 1982-06-04 1983-12-08 Beecham Group Plc Benzamide and anilide derivatives of 8-azabicyclo-(3.2.1)- -octane
US4694016A (en) 1985-10-18 1987-09-15 International Minerals & Chemical Corp. Phthalamide derivatives with anthelmintic activity
US6137002A (en) 1993-07-22 2000-10-24 Eli Lilly And Company Glycoprotein IIb/IIIa antagonists
EA001437B1 (ru) 1996-03-28 2001-02-26 Глаксо Груп Лимитед Производные пирролопирролона в качестве ингибиторов нейтрофильной эластазы
HRP970371A2 (en) * 1996-07-13 1998-08-31 Kathryn Jane Smith Heterocyclic compounds
GEP20012390B (en) 1996-11-11 2001-03-25 Byk Gulden Lomberg Chem Fab Benzonaphthyridines as Bronchial Therapeutics
GB9715584D0 (en) 1997-07-23 1997-10-01 Eisai Co Ltd Compounds
DE19738615A1 (de) 1997-09-04 1999-03-11 Clariant Gmbh Neue Lichtschutzmittel auf Basis von sterisch gehinderten Aminen
US5969014A (en) 1997-09-23 1999-10-19 Clariant Finance (Bvi) Limited Synergistic polyamide stabilization method
US6589954B1 (en) 1998-05-22 2003-07-08 Scios, Inc. Compounds and methods to treat cardiac failure and other disorders
AU772477B2 (en) 1998-08-28 2004-04-29 Scios Inc. Inhibitors of p38-alpha kinase
DE19843793C2 (de) 1998-09-24 2000-08-03 Gruenenthal Gmbh Substituierte Benzamide
US5965261A (en) 1998-11-16 1999-10-12 Clariant Finance (Bvi) Limited Polyester
US6953855B2 (en) 1998-12-11 2005-10-11 Targacept, Inc. 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof
DK1218380T3 (da) 1999-10-08 2004-03-15 Gruenenthal Gmbh Bicykliske imidazo-3-yl-aminoderivater substitueret i seksledsringen
US6436965B1 (en) 2000-03-02 2002-08-20 Merck Frosst Canada & Co. PDE IV inhibiting amides, compositions and methods of treatment
US7273868B2 (en) 2000-04-28 2007-09-25 Tanabe Seiyaku Co., Ltd. Pyrazine derivatives
JP2002371059A (ja) * 2000-05-16 2002-12-26 Takeda Chem Ind Ltd メラニン凝集ホルモン拮抗剤
AU2001273040A1 (en) 2000-06-27 2002-01-08 Du Pont Pharmaceuticals Company Factor xa inhibitors
AU2001280187A1 (en) 2000-08-28 2002-03-13 Toray Industries, Inc. Cyclic amine derivatives
DE10050663A1 (de) 2000-10-13 2002-04-18 Gruenenthal Gmbh Verwendung von substituierten Imidazo[1,2-a]pyridin-, -pyrimidin- und pyrazin-3-yl-amin-Derivaten zur Herstellung von Medikamenten zur NOS-Inhibierung
EP1415987B1 (en) 2000-10-20 2007-02-28 Eisai R&D Management Co., Ltd. Nitrogenous aromatic ring compounds as anti cancer agents
SE0102764D0 (sv) 2001-08-17 2001-08-17 Astrazeneca Ab Compounds
BR0212123A (pt) 2001-08-24 2004-07-20 Upjohn Co 7-aza[2.2.1]biciclo-heptanos substituìdos com arila para o tratamento de doenças
EP1425286B1 (en) 2001-09-12 2007-02-28 Pharmacia & Upjohn Company LLC Substituted 7-aza-[2.2.1]bicycloheptanes for the treatment of diseases
US6858613B2 (en) 2002-02-19 2005-02-22 Pfizer Inc. Fused bicyclic-N-bridged-heteroaromatic carboxamides for the treatment of disease
WO2003072578A1 (en) 2002-02-20 2003-09-04 Pharmacia & Upjohn Company Azabicyclic compounds with alfa7 nicotinic acetylcholine receptor activity
AU2003245669A1 (en) 2002-06-21 2004-01-06 Cellular Genomics, Inc. Certain aromatic monocycles as kinase modulators
DE10238865A1 (de) * 2002-08-24 2004-03-11 Boehringer Ingelheim International Gmbh Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
RU2005118407A (ru) 2002-12-13 2006-03-10 СмитКлайн Бичем Корпорейшн (US) Производные пиперидина в качестве антагонистов ccr5
BR0317659A (pt) * 2002-12-23 2005-12-06 Aventis Pharma Gmbh Derivados de pirazol como inibidores de fator xa
TW200503994A (en) 2003-01-24 2005-02-01 Novartis Ag Organic compounds
US7208491B2 (en) 2003-02-07 2007-04-24 Hoffmann-La Roche Inc. N-monoacylated o-phenylenediamines
GB2400101A (en) 2003-03-28 2004-10-06 Biofocus Discovery Ltd Compounds capable of binding to the active site of protein kinases
GB0314054D0 (en) 2003-06-17 2003-07-23 Pfizer Ltd Amide derivatives as selective serotonin re-uptake inhibitors
TWI372050B (en) 2003-07-03 2012-09-11 Astex Therapeutics Ltd (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles
WO2005020921A2 (en) 2003-08-29 2005-03-10 Exelixis, Inc. C-kit modulators and methods of use
EP1780211A3 (en) * 2003-09-30 2007-06-06 Amgen Inc. Vanilloid receptor ligands and their use in treatments
EP1892306A3 (en) 2003-10-06 2008-06-11 Bayer HealthCare AG Methods and kits for investigating cancer
GB0324159D0 (en) 2003-10-15 2003-11-19 Glaxo Group Ltd Novel compounds
US7196100B2 (en) * 2003-12-12 2007-03-27 Eli Lilly And Company Opioid receptor antagonists
US7544803B2 (en) 2004-01-23 2009-06-09 Amgen Inc. Vanilloid receptor ligands and their use in treatments
PE20060315A1 (es) 2004-05-24 2006-05-15 Irm Llc Compuestos de tiazol como moduladores de ppar
CA2566526C (en) * 2004-06-02 2012-10-23 F. Hoffmann-La Roche Ag Naphthaline derivatives useful as histamine-3-receptor ligands
US7714021B2 (en) 2004-06-15 2010-05-11 Merck & Co., Inc. Pyrrolidin-3-yl compounds useful as beta-secretase inhibitors for the treatment of Alzheimer's disease
ES2306170T3 (es) * 2004-06-21 2008-11-01 F. Hoffmann-La Roche Ag Derivados de indol como antagonistas redeptores de histamina.
ATE460410T1 (de) * 2004-08-25 2010-03-15 Boehringer Ingelheim Pharma 2-arylcarbamoyl-indole als zytokinhemmer
MX2007004465A (es) 2004-10-19 2007-05-07 Hoffmann La Roche Derivados de quinolina.
AU2005301568B2 (en) 2004-11-08 2011-06-09 Msd K.K. Novel fused imidazole derivative
ATE440833T1 (de) * 2004-11-29 2009-09-15 Lilly Co Eli Antithrombotische diamide
CA2588517A1 (en) 2004-12-01 2006-06-08 Devgen N.V. 5-carboxamido substituted thiazole derivatives that interact with ion channels, in particular with ion channels from the kv family
AP2334A (en) 2004-12-17 2011-12-06 Glenmark Pharmaceuticals Sa Novel heterocyclic compounds useful for the treatment of inflamatory and allergic disorders.
US20080207634A1 (en) 2004-12-17 2008-08-28 Kristjan Gudmundsson Chemical Compounds
GB0428235D0 (en) 2004-12-23 2005-01-26 Glaxo Group Ltd Novel compounds
US7998974B2 (en) 2005-03-03 2011-08-16 Sirtris Pharmaceuticals, Inc. Fused heterocyclic compounds and their use as sirtuin modulators
MX2007011234A (es) 2005-03-14 2007-11-12 Transtech Pharma Inc Derivados de benzazol, composiciones y metodos de uso en la forma de inhibidores de b-secretasa.
WO2006101434A1 (en) 2005-03-22 2006-09-28 Astrazeneca Ab NOVEL TETRAHYDRO-1H-PYRIDO [4,3-b] INDOLE DERIVATIVES AS CB1’ RECEPTOR LIGANDS
GB0508472D0 (en) 2005-04-26 2005-06-01 Glaxo Group Ltd Compounds
WO2007050124A1 (en) * 2005-05-19 2007-05-03 Xenon Pharmaceuticals Inc. Fused piperidine derivatives and their uses as therapeutic agents
EP1907376A2 (en) 2005-07-05 2008-04-09 Aryx Therapeutics, Inc. Stereoisomeric pyridyl and pyridonyl compounds and methods for the treatment of gastrointestinal and central nervous system disorders
WO2007063000A1 (en) 2005-11-30 2007-06-07 F. Hoffmann-La Roche Ag 5-substituted indole-2-carboxamide derivatives
EP1968967B1 (en) 2005-11-30 2011-04-27 F. Hoffmann-La Roche AG 1,1-dioxo-thiomorpholinyl indolyl methanone derivatives for use as h3 modulators
WO2007062999A2 (en) 2005-11-30 2007-06-07 F. Hoffmann-La Roche Ag 1,5-substituted indol-2-yl amide derivatives
JP2009521451A (ja) * 2005-12-21 2009-06-04 シェーリング コーポレイション ヒスタミンｈ３アンタゴニストとして有用な置換アニリン誘導体
WO2007087548A2 (en) 2006-01-25 2007-08-02 Smithkline Beecham Corporation Chemical compounds
AR059197A1 (es) 2006-01-25 2008-03-19 Smithkline Beecham Corp Derivados de indazolo piridina para el tratamiento de hiv
US20090036429A1 (en) 2006-02-17 2009-02-05 Ohler Norman E Hydroxypiperidine Derivatives and Uses Thereof
WO2007099423A1 (en) 2006-03-02 2007-09-07 Pfizer Products Inc. 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists
JP2009531314A (ja) * 2006-03-10 2009-09-03 ニューロジェン・コーポレーション ピペラジニルオキソアルキルテトラヒドロイソキノリン類および関連類似物
TWI543988B (zh) 2006-03-16 2016-08-01 科學製藥股份有限公司 結合於細胞凋亡抑制蛋白（ｉａｐ）之桿狀病毒ｉａｐ重複序列（ｂｉｒ）區域之化合物
CA2645551C (en) * 2006-03-16 2016-06-28 Renovis, Inc. Bicycloheteroaryl compounds as p2x7 modulators and uses thereof
EP2463283B1 (en) 2006-04-20 2014-06-11 Pfizer Products Inc. Fused phenyl Amido heterocyclic compounds for the prevention and treatment of glucokinase-mediated diseases
CA2654792A1 (en) 2006-06-12 2007-12-21 Merck Frosst Canada Ltd. Azetidine derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase
JP2009539885A (ja) 2006-06-13 2009-11-19 メルク フロスト カナダ リミテツド ステアロイルコエンザイムａデルタ−９デサチュラーゼの阻害剤としてのアザシクロペンタン誘導体
WO2008007979A1 (en) 2006-07-12 2008-01-17 Auckland Uniservices Limited (2,6-dioxo-3-piperinyl)amidobenzoic immunomodulatory and anti-cancer derivatives
TW200821303A (en) 2006-08-08 2008-05-16 Speedel Experimenta Ag Organic compounds
WO2008083124A1 (en) 2006-12-28 2008-07-10 Rigel Pharmaceuticals, Inc. N-substituted-heterocycloalkyloxybenzamide compounds and methods of use
CN101668746A (zh) * 2007-03-01 2010-03-10 詹森药业有限公司 作为组胺h3受体调节剂的四氢异喹啉化合物
WO2008133975A1 (en) * 2007-04-26 2008-11-06 Avalon Pharmaceuticals Multi-ring compounds and uses thereof
JP5544296B2 (ja) * 2007-11-16 2014-07-09 ライジェル ファーマシューティカルズ， インコーポレイテッド 代謝障害のためのカルボキサミド、スルホンアミド、およびアミン化合物
ES2553340T3 (es) * 2007-12-12 2015-12-07 Rigel Pharmaceuticals, Inc. Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos
JP5658138B2 (ja) * 2008-04-23 2015-01-21 ライジェル ファーマシューティカルズ， インコーポレイテッド 代謝障害の処置のためのカルボキサミド化合物
CN102365275B (zh) * 2009-01-28 2014-09-24 里格尔药品股份有限公司 羧酰胺化合物及其使用方法

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