CA2602248C - Dipeptidyl peptidase-iv inhibiting compounds, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent - Google Patents

Dipeptidyl peptidase-iv inhibiting compounds, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent Download PDF

Info

Publication number
CA2602248C
CA2602248C CA2602248A CA2602248A CA2602248C CA 2602248 C CA2602248 C CA 2602248C CA 2602248 A CA2602248 A CA 2602248A CA 2602248 A CA2602248 A CA 2602248A CA 2602248 C CA2602248 C CA 2602248C
Authority
CA
Canada
Prior art keywords
trifluoromethyl
amino
dihydropyrido
oxo
butyl
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.)
Active
Application number
CA2602248A
Other languages
English (en)
French (fr)
Other versions
CA2602248A1 (en
Inventor
Chang-Seok Lee
Jong Sung Koh
Ki Dong Koo
Geun Tae Kim
Kyoung-Hee Kim
Sang Yong Hong
Sungsub Kim
Min-Jung Kim
Hyeon Joo Yim
Dongchul Lim
Hye Jin Kim
Hee Oon Han
Seong Cheol Bu
Oh Hwan Kwon
Sung Ho Kim
Gwong-Cheung Hur
Ji Young Kim
Zi-Ho Yeom
Dong-Jun Yeo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Life Sciences Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by LG Life Sciences Ltd filed Critical LG Life Sciences Ltd
Publication of CA2602248A1 publication Critical patent/CA2602248A1/en
Application granted granted Critical
Publication of CA2602248C publication Critical patent/CA2602248C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07D487/04—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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D413/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Diabetes (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Child & Adolescent Psychology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
CA2602248A 2005-04-01 2006-03-30 Dipeptidyl peptidase-iv inhibiting compounds, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent Active CA2602248C (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
KR10-2005-0027756 2005-04-01
KR20050027756 2005-04-01
KR10-2005-0053761 2005-06-22
KR20050053761 2005-06-22
KR10-2005-0085980 2005-09-15
KR20050085980 2005-09-15
KR20050122361 2005-12-13
KR10-2005-0122361 2005-12-13
PCT/KR2006/001169 WO2006104356A1 (en) 2005-04-01 2006-03-30 Dipeptidyl peptidase-iv inhibiting compounds, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent

Publications (2)

Publication Number Publication Date
CA2602248A1 CA2602248A1 (en) 2006-10-05
CA2602248C true CA2602248C (en) 2011-06-28

Family

ID=37053586

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2602248A Active CA2602248C (en) 2005-04-01 2006-03-30 Dipeptidyl peptidase-iv inhibiting compounds, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent

Country Status (28)

Country Link
US (1) US7879848B2 (OSRAM)
EP (1) EP1863812B1 (OSRAM)
JP (1) JP4977685B2 (OSRAM)
KR (3) KR100776623B1 (OSRAM)
CN (1) CN101151265B (OSRAM)
AR (1) AR053195A1 (OSRAM)
AT (1) ATE473976T1 (OSRAM)
AU (1) AU2006229520B2 (OSRAM)
BR (1) BRPI0609424B8 (OSRAM)
CA (1) CA2602248C (OSRAM)
DE (1) DE602006015443D1 (OSRAM)
DK (1) DK1863812T3 (OSRAM)
EA (1) EA012591B1 (OSRAM)
ES (1) ES2349178T3 (OSRAM)
IL (1) IL185479A (OSRAM)
MA (1) MA29586B1 (OSRAM)
MX (1) MX2007012175A (OSRAM)
MY (1) MY150102A (OSRAM)
NZ (1) NZ560789A (OSRAM)
PE (1) PE20061354A1 (OSRAM)
PL (1) PL1863812T3 (OSRAM)
PT (1) PT1863812E (OSRAM)
SI (1) SI1863812T1 (OSRAM)
TW (1) TWI357902B (OSRAM)
UA (1) UA89396C2 (OSRAM)
UY (1) UY29448A1 (OSRAM)
WO (1) WO2006104356A1 (OSRAM)
ZA (1) ZA200708304B (OSRAM)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007148185A2 (en) 2006-06-21 2007-12-27 Pfizer Products Inc. Substituted 3 -amino- pyrrolidino-4 -lactams as dpp inhibitors
BRPI0715160A2 (pt) 2006-08-08 2013-06-11 Sanofi Aventis imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso
CN101652147B (zh) 2007-04-03 2013-07-24 田边三菱制药株式会社 二肽基肽酶iv抑制化合物和甜味剂的并用
CN101357922B (zh) * 2007-08-02 2011-05-18 山东轩竹医药科技有限公司 新的dpp-iv抑制剂
EP2025674A1 (de) 2007-08-15 2009-02-18 sanofi-aventis Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
CN102026993A (zh) * 2007-12-05 2011-04-20 阿斯利康(瑞典)有限公司 新化合物iii
CA2710109C (en) * 2007-12-21 2016-07-19 Lg Life Sciences Ltd. Dipeptidyl peptidase-iv inhibiting compounds, methods of preparing the same, and pharmaceutical compositions containing the same as active agent
CL2008003653A1 (es) 2008-01-17 2010-03-05 Mitsubishi Tanabe Pharma Corp Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica.
CN101486689B (zh) * 2008-01-18 2011-08-10 山东轩竹医药科技有限公司 具有磺酰胺基甲酰胺哌嗪结构的dpp-iv抑制剂
WO2010003624A2 (en) 2008-07-09 2010-01-14 Sanofi-Aventis Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof
JO2870B1 (en) * 2008-11-13 2015-03-15 ميرك شارب اند دوهم كورب Amino Tetra Hydro Pirans as Inhibitors of Peptide Dipeptide IV for the Treatment or Prevention of Diabetes
WO2010068601A1 (en) 2008-12-08 2010-06-17 Sanofi-Aventis A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof
WO2010103281A1 (en) * 2009-03-13 2010-09-16 Sun Chemical B.V. Cyclic carbamate compounds useful in energy-curable compositions
ES2443016T3 (es) 2009-08-26 2014-02-17 Sanofi Nuevos hidratos cristalinos de fluoroglicósidos heteroaromáticos, productos farmacéuticos que comprenden estos compuestos, y su empleo
US8871760B2 (en) * 2009-09-21 2014-10-28 Roche Palo Alto Llc [1,2,4]triazolo[3,4-C][1,4]oxazines as P2X7 modulators
WO2011107494A1 (de) 2010-03-03 2011-09-09 Sanofi Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung
CN102260265B (zh) * 2010-05-24 2015-09-02 上海阳帆医药科技有限公司 六氢吡咯[3,4-b]吡咯衍生物、其制备方法及其用途
US8933024B2 (en) 2010-06-18 2015-01-13 Sanofi Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases
US8530413B2 (en) 2010-06-21 2013-09-10 Sanofi Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments
TW201215388A (en) 2010-07-05 2012-04-16 Sanofi Sa (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments
TW201215387A (en) 2010-07-05 2012-04-16 Sanofi Aventis Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament
TW201221505A (en) 2010-07-05 2012-06-01 Sanofi Sa Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament
CA2810393C (en) * 2010-09-03 2016-04-12 Lg Life Sciences Ltd. Method of preparing 3-amino-4-(2-oxo-piperidin-1-yl)-butyric acid derivative for synthesizing medicament
TWI519533B (zh) * 2010-11-01 2016-02-01 Ｌｇ生命科學有限公司 １－｛（２Ｓ）－２－胺基－４－［２，４－雙（三氟甲基）－５，８－二氫吡啶并［３，４－ｄ］嘧啶－７（６Ｈ）－基］－４－側氧丁基｝－５，５－二氟哌啶－２－酮酒石酸鹽之水合物
EP2766349B1 (de) 2011-03-08 2016-06-01 Sanofi Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung
WO2012120055A1 (de) 2011-03-08 2012-09-13 Sanofi Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
US8828994B2 (en) 2011-03-08 2014-09-09 Sanofi Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
WO2012120053A1 (de) 2011-03-08 2012-09-13 Sanofi Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
US8871758B2 (en) 2011-03-08 2014-10-28 Sanofi Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof
WO2012170702A1 (en) 2011-06-08 2012-12-13 Arena Pharmaceuticals, Inc. Modulators of the gpr119 receptor and the treatment of disorders related thereto
WO2013037390A1 (en) 2011-09-12 2013-03-21 Sanofi 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
WO2013045413A1 (en) 2011-09-27 2013-04-04 Sanofi 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
US20150297573A1 (en) 2012-10-24 2015-10-22 INSERM (Institut National de la Santé et de la Recherche Médicale) TPL2 KINASE INHIBITORS FOR PREVENTING OR TREATING DIABETES AND FOR PROMOTING Beta-CELL SURVIVAL
CN105085528A (zh) * 2014-05-15 2015-11-25 成都贝斯凯瑞生物科技有限公司 作为二肽基肽酶-iv抑制剂的氨基四氢吡喃衍生物
US10426818B2 (en) 2015-03-24 2019-10-01 Inserm (Institut National De La Sante Et De La Recherche Medicale) Method and pharmaceutical composition for use in the treatment of diabetes
MX2018010109A (es) 2016-02-23 2018-12-17 Univ Indiana Res & Tech Corp Terapias de combinacion para tratamiento de atrofia muscular espinal.
KR102068754B1 (ko) * 2017-04-20 2020-01-21 주식회사 엘지화학 의약품 합성용 중간체 화합물의 제조 방법
PE20210839A1 (es) * 2017-11-16 2021-05-06 Lg Chemical Ltd Metodo de produccion de un compuesto intermedio para sintetizar un medicamento
CN108191647B (zh) * 2018-02-22 2020-09-29 江苏尚莱特医药化工材料有限公司 2,2-二氟二羧酸二烷基酯的合成方法
CN111537622B (zh) * 2019-11-29 2021-11-26 杭州华东医药集团新药研究院有限公司 一种度格列汀及其盐的杂质的检测方法
KR20250097733A (ko) 2023-12-21 2025-06-30 이니스트에스티 주식회사 디펩티딜 펩티데이즈-iv (dpp-iv) 억제제의 신규한 염, 이의 제조 방법 및 이를 포함하는 약제학적 조성물
KR20250137744A (ko) 2024-03-11 2025-09-19 엠에프씨 주식회사 제미글립틴의 신규 결정형 및 이의 제조방법
KR20250147756A (ko) 2024-03-27 2025-10-14 엠에프씨 주식회사 신규한 형태의 제미글립틴 말산염 결정형 및 이의 제조방법
KR20250155700A (ko) 2024-04-24 2025-10-31 주식회사 다산제약 제미글립틴 산부가염 제조방법 및 이를 유효성분으로 포함하는 dpp-4 저해용 조성물

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CO5150173A1 (es) 1998-12-10 2002-04-29 Novartis Ag Compuestos n-(glicilo sustituido)-2-cianopirrolidinas inhibidores de peptidasa de dipeptidilo-iv (dpp-iv) los cuales son efectivos en el tratamiento de condiciones mediadas por la inhibicion de dpp-iv
UA74912C2 (en) 2001-07-06 2006-02-15 Merck & Co Inc Beta-aminotetrahydroimidazo-(1,2-a)-pyrazines and tetratriazolo-(4,3-a)-pyrazines as inhibitors of dipeptylpeptidase for the treatment or prevention of diabetes
US6861440B2 (en) * 2001-10-26 2005-03-01 Hoffmann-La Roche Inc. DPP IV inhibitors
AU2002360732A1 (en) * 2001-12-26 2003-07-24 Guilford Pharmaceuticals Change inhibitors of dipeptidyl peptidase iv
AU2003225916A1 (en) * 2002-03-25 2003-10-13 Merck & Co., Inc. Beta-amino heterocyclic dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
ATE404538T1 (de) 2002-04-29 2008-08-15 Merck & Co Inc Tetrahydropyranylcyclopentyltetrahydroisochino- linmodulatoren der chemokinrezeptoraktivität
JP4530852B2 (ja) * 2002-07-15 2010-08-25 メルク・シャープ・エンド・ドーム・コーポレイション 糖尿病治療のためのピペリジノピリミジンジペプチジルペプチダーゼ阻害剤
JP2004285325A (ja) * 2002-12-17 2004-10-14 Fuji Photo Film Co Ltd パターン形成方法及び物質付着パターン材料
WO2004058266A1 (en) * 2002-12-20 2004-07-15 Merck & Co., Inc. 3-amino-4-phenylbutanoic acid derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
EP1589969A4 (en) * 2003-01-17 2008-08-13 Merck & Co Inc 3-AMINO-4-PHENYLBUTANEAN DERIVATEALS DIPEPTIDYLPEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
EP1592689A4 (en) 2003-01-31 2008-12-24 Merck & Co Inc 3-AMINO-4-PHENYLBUTANEAN DERIVATIVES AS DIPEPTIDYLPEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
BRPI0507971A (pt) * 2004-02-23 2007-07-24 Tufts College composto, composição farmacêutica, uso de um composto,método para inibir a atividade proteolìtica de uma enzima de clivagem pós-prolina e remédio empacotado
US7291427B2 (en) * 2004-03-19 2007-11-06 Fujifilm Corporation Surface graft material, conductive pattern material, and production method thereof
DE102004020908A1 (de) * 2004-04-28 2005-11-17 Grünenthal GmbH Substituierte 5,6,7,8,-Tetrahydro-pyrido[4,3-d]pyrimidin-2-yl- und 5,6,7,8,-Tetrahydro-chinazolin-2-yl-Verbindungen
DE102005016170A1 (de) * 2005-04-07 2006-10-12 Grünenthal GmbH 4,5,6,7- Tetrahydro-isoxazolo(4,5c)pyridin-Verbindungen und deren Verwendung zur Herstellung von Arzneimitteln
AU2006244206A1 (en) * 2005-05-10 2006-11-16 Vertex Pharmaceuticals Incorporated Bicyclic derivatives as modulators of ion channels
US20090176825A1 (en) * 2006-05-16 2009-07-09 Fitch Duke M Prolyl hydroxylase inhibitors
CA2712265A1 (en) * 2008-01-17 2009-07-23 Gruenenthal Gmbh Substituted sulfonamide derivatives

Also Published As

Publication number Publication date
US7879848B2 (en) 2011-02-01
KR20070098774A (ko) 2007-10-05
EA200701854A1 (ru) 2008-02-28
AU2006229520A1 (en) 2006-10-05
MY150102A (en) 2013-11-29
KR20060105609A (ko) 2006-10-11
EA012591B1 (ru) 2009-10-30
IL185479A (en) 2013-08-29
DE602006015443D1 (de) 2010-08-26
CA2602248A1 (en) 2006-10-05
WO2006104356A1 (en) 2006-10-05
AR053195A1 (es) 2007-04-25
UY29448A1 (es) 2006-10-31
ES2349178T3 (es) 2010-12-28
BRPI0609424A2 (pt) 2010-03-30
CN101151265A (zh) 2008-03-26
PE20061354A1 (es) 2007-01-02
AU2006229520B2 (en) 2010-07-29
ZA200708304B (en) 2008-11-26
PT1863812E (pt) 2010-08-04
EP1863812B1 (en) 2010-07-14
DK1863812T3 (da) 2010-10-18
KR100830902B1 (ko) 2008-05-22
IL185479A0 (en) 2008-01-06
ATE473976T1 (de) 2010-07-15
MX2007012175A (es) 2007-11-21
EP1863812A1 (en) 2007-12-12
KR100776623B1 (ko) 2007-11-15
MA29586B1 (fr) 2008-07-01
KR20070094714A (ko) 2007-09-21
NZ560789A (en) 2009-11-27
KR100794184B1 (ko) 2008-01-11
SI1863812T1 (sl) 2010-11-30
BRPI0609424B8 (pt) 2021-05-25
JP4977685B2 (ja) 2012-07-18
UA89396C2 (ru) 2010-01-25
BRPI0609424B1 (pt) 2021-01-26
US20080188471A1 (en) 2008-08-07
PL1863812T3 (pl) 2011-02-28
TW200724542A (en) 2007-07-01
JP2008534581A (ja) 2008-08-28
CN101151265B (zh) 2012-11-28
TWI357902B (en) 2012-02-11
EP1863812A4 (en) 2009-06-24

Similar Documents

Publication Publication Date Title
CA2602248C (en) Dipeptidyl peptidase-iv inhibiting compounds, methods of preparing the same, and pharmaceutical compositions containing the same as an active agent
US12202836B2 (en) Bicyclic-fused heteroaryl or aryl compounds
US20090312310A1 (en) Imidazothiazole derivatives
AU2018244349A1 (en) Compounds that inhibit Mcl-1 protein
CA3079557A1 (en) Dihydropyrimidine compounds and uses thereof in medicine
JPWO2009151069A1 (ja) ４，７−ジアザスピロ［２．５］オクタン環構造を有するイミダゾチアゾール誘導体
CA3160522A1 (en) Compounds active towards nuclear receptors
CN114828963A (zh) 作为Kv1.3钾SHAKER通道阻滞剂的芳基杂二环化合物
JP2009298713A (ja) イミダゾチアゾール誘導体
HK1234395A1 (en) Bicyclic-fused heteroaryl or aryl compounds and their use as irak4 inhibitors
HK1234395B (zh) 双环稠合的杂芳基或芳基化合物以及它们作为irak4拟制剂的用途

Legal Events

Date Code Title Description
EEER Examination request