WO2010093845A1 - Triazole and imidazole derivatives for use as tgr5 agonists in the treatment of diabetes and obesity - Google Patents

Triazole and imidazole derivatives for use as tgr5 agonists in the treatment of diabetes and obesity Download PDF

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Publication number
WO2010093845A1
WO2010093845A1 PCT/US2010/023981 US2010023981W WO2010093845A1 WO 2010093845 A1 WO2010093845 A1 WO 2010093845A1 US 2010023981 W US2010023981 W US 2010023981W WO 2010093845 A1 WO2010093845 A1 WO 2010093845A1
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WIPO (PCT)
Prior art keywords
fluorophenyl
methyl
methylethyl
chloro
alkyl
Prior art date
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Ceased
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PCT/US2010/023981
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English (en)
French (fr)
Inventor
Venkataiah Bollu
Brant Clayton Boren
Jackline Eve Dalgard
Brenton T. Flatt
Nadia Haq
Sarah Hudson
Raju Mohan
Michael Morrissey
Benjamin Pratt
Tie-Lin Wang
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Exelixis Inc
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Exelixis Inc
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Priority to US13/148,811 priority Critical patent/US8785488B2/en
Priority to CN2010800163259A priority patent/CN102395567A/zh
Priority to EP10704701A priority patent/EP2396304A1/en
Priority to JP2011550244A priority patent/JP2012517479A/ja
Publication of WO2010093845A1 publication Critical patent/WO2010093845A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/84—Sulfur 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • 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
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
    • A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
    • 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
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

Definitions

  • R C21 is halogen (e.g., fluoro) and R C20 is -OR C12 or -OCi-C 4 alkyl-R c ⁇ , heteroaryl optionally substituted with one, two, or three R C1 ° groups, pyridyl optionally substituted with one, two, or three R C1 ° groups,
  • R 5 is optionally substituted with 0-4 R A10A groups and 1 R A10B group.
  • R 5 is optionally substituted with 0-3 R A10A groups and 1-2 R A10B groups.
  • R D1 is selected from phenyl, -N(H)-phenyl, cyclohexyl, cyclopentyl, piperidinyl, piperazinyl, pyrrolidinyl, morpholinyl, 1,2,3,6-tetrahydropyridine, heteroarylheterocycloalkyl, pyridinyl, oxazolyl, pyrazinyl, quinolinyl, 1,2,4-oxadiazolyl, 1,2,3,4-tetrahydroquinolinyl, and pyrazolyl, wherein R D1 is substituted with 1, 2 or 3 R D1 °, provided that substitution of the R D1 ° can only occur by replacing a hydrogen that is covalently bound to either a carbon or a nitrogen of the R D1 °, wherein the 1-3 R D1 ° groups are 0-2 A groups and 1 B group; each A group, when they occur, is independently selected from halo, -CF 3 ,
  • R c is phenyl, -CH 2 -phenyl or pyridinyl, wherein the cyclic group of R c can be optionally substituted with 1, 2 or 3 R C1 °, provided that substitution of R c can only occur by replacing a hydrogen that is covalently bound to either a carbon or a nitrogen of R c , and wherein the 1, 2 or 3 R C1 ° groups are independently selected from R C1OA and R C1OB , provided that R c cannot be substituted with more than 1 R C1OB group; each R C1OA , when they occur, is independently selected from -(Ci-C 3 )alkyl optionally substituted with 1-3 groups selected from -OH, methoxy, -CF 3 and halo;
  • R D11B is -S(O) 2 OH.
  • R D11B is -C(O)-(C i-C 3 )alkyl.
  • Sulfonylureas e.g., tolbutamide (3-butyl-l-(4-methylphenyl)sulfonylurea), acetohexamide (4-acetyl- ⁇ /-(cyclohexylcarbamoyl)benzenesulfonamide), tolazamide (3-azepan-l-yl-l-(4-methylphenyl)sulfonyl-urea), chlorpropamide (N- (4-chlorophenyl)sulfonylmethanamide), glipizide (N-[I-[A- (cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-5-methyl-pyrazine-2-carboxamide), glyburide (5-chloro- ⁇ /-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2- meth
  • Administration of the compounds of this disclosure, or their pharmaceutically acceptable salts, in pure form or in an appropriate pharmaceutical composition can be carried out via any of the accepted modes of administration or agents for serving similar utilities.
  • administration can be, for example, orally, nasally, parenterally (intravenous, intramuscular, or subcutaneous), topically, transdermally, intravaginally, intravesically, intracistemally, or rectally, in the form of solid, semi-solid, lyophilized powder, or liquid dosage forms, such as for example, tablets, suppositories, pills, soft elastic and hard gelatin capsules, powders, solutions, suspensions, or aerosols, or the like, preferably in unit dosage forms suitable for simple administration of precise dosages.
  • the compositions will include a conventional pharmaceutical carrier, excipient, and/or diluent and a compound of this disclosure as the/an active agent, and, in addition, can include carriers and adjuvants, etc.
  • Spiro ring refers to a ring originating from a particular annular carbon of another ring. For example, as depicted below:
  • Step (j): Compounds of formula (I c ) may be prepared by reaction of amine HN(R Y )R D1 with sulfonyl chloride (IX) in a suitable solvent, such as DCM, and in the presence of a base, such as triethylamine.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
PCT/US2010/023981 2009-02-12 2010-02-12 Triazole and imidazole derivatives for use as tgr5 agonists in the treatment of diabetes and obesity Ceased WO2010093845A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US13/148,811 US8785488B2 (en) 2009-02-12 2010-02-12 Triazole and imidazole derivatives for use as TGR5 agonists in the treatment of diabetes and obesity
CN2010800163259A CN102395567A (zh) 2009-02-12 2010-02-12 在治疗糖尿病和肥胖症中用作的tgr5激动剂的三唑和咪唑衍生物
EP10704701A EP2396304A1 (en) 2009-02-12 2010-02-12 Triazole and imidazole derivatives for use as tgr5 agonists in the treatment of diabetes and obesity
JP2011550244A JP2012517479A (ja) 2009-02-12 2010-02-12 糖尿病および肥満の処置においてｔｇｒ５アゴニストとして使用するためのトリアゾールおよびイミダゾール誘導体

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US15216309P 2009-02-12 2009-02-12
US61/152,163 2009-02-12
US28413909P 2009-12-11 2009-12-11
US61/284,139 2009-12-11

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WO2010093845A1 true WO2010093845A1 (en) 2010-08-19

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US (1) US8785488B2 (enExample)
EP (1) EP2396304A1 (enExample)
JP (2) JP2012517479A (enExample)
KR (1) KR20110119790A (enExample)
CN (1) CN102395567A (enExample)
AR (1) AR075255A1 (enExample)
TW (1) TW201040168A (enExample)
WO (1) WO2010093845A1 (enExample)

Cited By (26)

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WO2011071565A1 (en) * 2009-12-11 2011-06-16 Exelixis, Inc. Tgr5 agonists
WO2011140160A1 (en) 2010-05-06 2011-11-10 Bristol-Myers Squibb Company Bicyclic heteroaryl compounds as gpr119 modulators
WO2012082947A1 (en) * 2010-12-16 2012-06-21 Irm Llc Compounds and compositions as tgr5 agonists
WO2012109646A1 (en) 2011-02-11 2012-08-16 Vertex Pharmaceuticals Incorporated Treatment of hcv in hiv infection patients
WO2012149236A1 (en) 2011-04-28 2012-11-01 Bristol-Myers Squibb Company Novel bicyclic nitrogen containing heteroaryl tgr5 receptor modulators
WO2013054338A1 (en) * 2011-07-06 2013-04-18 Cadila Healthcare Limited 2-thio-imidazole derivatives as tgr5 modulators
WO2012174164A3 (en) * 2011-06-15 2013-04-25 Metabolex, Inc. Agonists of gpr131 and uses thereof
WO2013062887A1 (en) * 2011-10-26 2013-05-02 Merck Sharp & Dohme Corp. Substituted pyridine derivatives useful as gpr131 agonists
US20130143929A1 (en) * 2010-09-29 2013-06-06 Ei Du Pont De Nemours And Company Fungicidal imidazoles
WO2013102929A1 (en) 2011-12-26 2013-07-11 Cadila Healthcare Limited Novel compounds for treatment of diabetes, obesity or related disorders
WO2013164838A1 (en) * 2012-03-07 2013-11-07 Cadila Healthcare Limited Heterocyclic compounds and their use for treatment of diabetes, obesity or related disorders
WO2014062044A1 (en) 2012-10-15 2014-04-24 Vilnius University Fluorinated benzenesulfonamides as inhibitors of carbonic anhydrase
WO2014100025A1 (en) * 2012-12-17 2014-06-26 Exelixis, Inc. Tgr5 agonists having an imidazole or triazole core with subtituent having a quaternary nitrogen
WO2014100021A1 (en) * 2012-12-17 2014-06-26 Exelixis, Inc. Tgr5 agonists: imidazole and triazole compounds containing a quaternary nitrogen
US8883714B2 (en) 2008-04-07 2014-11-11 Arena Pharmaceuticals, Inc. Pharmaceutical compositions comprising GPR119 agonists which act as peptide YY (PYY) secretagogues
WO2015189330A1 (en) * 2014-06-12 2015-12-17 Universite De Lille 2 Droit Et Sante Imidazol- or 1,2,4-triazol-derivatives and their use
US9593109B2 (en) 2011-08-26 2017-03-14 Cymabay Therapeutics, Inc. Bicyclic agonists of GPR131 and uses thereof
WO2017042380A1 (en) * 2015-09-11 2017-03-16 Universite De Lille 2 Droit Et Sante Novel 5-amino-2-thioimidazole compounds and their use
EP3210469A1 (de) 2016-02-23 2017-08-30 Bayer Cropscience AG Verwendung von substituierten thio-1,2,4-triazolen zur steigerung der stresstoleranz in pflanzen
JP2017536379A (ja) * 2014-11-26 2017-12-07 エナンタ ファーマシューティカルズ インコーポレイテッド Ｆｘｒ／ｔｇｒ５アゴニストとしての胆汁酸誘導体およびその使用方法
US11040998B2 (en) 2015-03-31 2021-06-22 Enanta Pharmaceuticals, Inc. Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof
WO2021174048A1 (en) 2020-02-28 2021-09-02 Kallyope, Inc. Gpr40 agonists
US11279702B2 (en) 2020-05-19 2022-03-22 Kallyope, Inc. AMPK activators
US11407768B2 (en) 2020-06-26 2022-08-09 Kallyope, Inc. AMPK activators
US11512065B2 (en) 2019-10-07 2022-11-29 Kallyope, Inc. GPR119 agonists
EP4377297A4 (en) * 2021-07-30 2025-05-28 The Regents of the University of California Compounds for modulating epithelial 15-(s)-lipoxygenase-2 and methods of use for same

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US9664677B2 (en) 2010-04-19 2017-05-30 Massachusetts Institute Of Technology Polymer-nanostructure composition for selective molecular recognition
CN103864754B (zh) * 2012-12-10 2016-12-21 中国科学院上海药物研究所 五元唑类杂环化合物及其制备方法、药物组合物和用途
CN103755652B (zh) * 2013-12-20 2015-08-05 陕西理工学院 一种磺酰胺类化合物及其应用
CN105017170A (zh) * 2015-07-13 2015-11-04 佛山市赛维斯医药科技有限公司 一类腈基苯三氮唑亚砜类11β-HSD1抑制剂及其用途
CN104987312A (zh) * 2015-07-13 2015-10-21 佛山市赛维斯医药科技有限公司 一类胺基苯三氮唑亚砜类11β-HSD1抑制剂及其用途
CN104987313A (zh) * 2015-07-13 2015-10-21 佛山市赛维斯医药科技有限公司 一类末端取代的三氮唑亚砜类化合物、其制备方法及其用途
CN105001171A (zh) * 2015-07-13 2015-10-28 佛山市赛维斯医药科技有限公司 一类硝基苯三氮唑亚砜类11β-HSD1抑制剂及其用途
WO2018005801A2 (en) * 2016-07-01 2018-01-04 Venenum Biodesign Llc Novel non-systemic tgr5 agonists
CN106432222A (zh) * 2016-09-19 2017-02-22 丹诺医药(苏州）有限公司 8‑氯‑1‑环丙基‑7‑氟‑9‑甲基‑4‑氧‑4‑氢‑喹嗪‑3‑羧酸酯及其制备方法
CN111039880B (zh) * 2019-12-10 2022-06-21 河南大学 咪康唑及其衍生物作为tgr5激动剂的应用
CN111763173B (zh) * 2020-07-14 2022-11-01 河南大学 苯乙基咪唑类衍生物及其用途
US12221423B1 (en) 2023-10-23 2025-02-11 King Faisal University 3-(3-fluorophenyl)-5-(4-methoxybenzylthio)-4-phenyl-4H-1,2,4-triazole as an antimicrobial compound
CN120787220A (zh) * 2024-02-04 2025-10-14 成都麻沸散医药科技有限公司 一种杂环化合物及其制药用途

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