IL320810A - Glucagon-like peptide 1 agonists - Google Patents

Glucagon-like peptide 1 agonists

Info

Publication number
IL320810A
IL320810A IL320810A IL32081025A IL320810A IL 320810 A IL320810 A IL 320810A IL 320810 A IL320810 A IL 320810A IL 32081025 A IL32081025 A IL 32081025A IL 320810 A IL320810 A IL 320810A
Authority
IL
Israel
Prior art keywords
methoxy
oxetan
methyl
carboxylic acid
ylmethyl
Prior art date
Application number
IL320810A
Other languages
Hebrew (he)
Inventor
Qi Chen
Todd Fields
Pushkar Gajendra Ghanekar
Jared Thomas Hammill
Eric Michael Woerly
Original Assignee
Lilly Co Eli
Qi Chen
Todd Fields
Pushkar Gajendra Ghanekar
Jared Thomas Hammill
Eric Michael Woerly
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 Lilly Co Eli, Qi Chen, Todd Fields, Pushkar Gajendra Ghanekar, Jared Thomas Hammill, Eric Michael Woerly filed Critical Lilly Co Eli
Publication of IL320810A publication Critical patent/IL320810A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero 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
    • A61K31/435—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
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
    • C07D413/14—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Engineering & Computer Science (AREA)
  • Child & Adolescent Psychology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (9)

30435_OUS -43- Claims
1. A compound of the formula: wherein is phenyl, a 5 or 6-membered heteroaryl or pyridone, which phenyl, heteroaryl or pyridone is optionally substituted with one or two R; R at each occurrence is independently CN, halo, C1-C3alkyl, C1-C3alkoxy, -C(O)NH2 or 5-membered heteroaryl; R at each occurrence is independently halo or methyl; R is C1-C4alkoxy optionally substituted with C1-C2alkoxy; or a pharmaceutically acceptable salt thereof.
2. The compound according to claim 1, which is of the formula: wherein R is F or OCH3; R is F or CH3; and R is -OCH3, or -OCH2CH2OCH3, or a pharmaceutically acceptable salt thereof.
3. The compound according to claim 1, which is selected from: 2-[[4-[6-[(4-Cyano-2-fluoro-phenyl)methoxy]-2-pyridyl]-2-fluoro-5-methyl- phenyl]methyl]-7-methoxy-3-[[oxetan-2-yl]methyl]benzimidazole-5-carboxylic acid; 2-(4-(6-((4-Cyano-2-fluorobenzyl)oxy)pyridin-2-yl)-2,5-difluorobenzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 30435_OUS -44- 2-(4-(6-((5-Cyanopyridin-2-yl)methoxy)pyridin-2-yl)-2,5-difluorobenzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(4-(6-((6-Cyanopyridin-3-yl)methoxy)pyridin-2-yl)-2,5-difluorobenzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(4-(6-((4-Cyano-2-fluorobenzyl)oxy)pyridin-2-yl)-2,5-difluorobenzyl)-4-(2- methoxyethoxy)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-[[4-[6-[(6-Cyano-2-methyl-3-pyridyl)methoxy]-2-pyridyl]-2,5-difluoro-phenyl]methyl]-7-methoxy-3-[[oxetan-2-yl]methyl]benzimidazole-5-carboxylic acid; 2-[[4-[6-[(6-carbamoyl-2-methyl-3-pyridyl)methoxy]-2-pyridyl]-2,5-difluoro-phenyl]methyl]-7-methoxy-3-[[oxetan-2-yl]methyl]benzimidazole-5-carboxylic acid; 2-[[2,5-Difluoro-4-[6-[(1-methyl-6-oxo-3-pyridyl)methoxy]-2-pyridyl]phenyl]methyl]-7-(2-methoxyethoxy)-3-[[oxetan-2-yl]methyl]benzimidazole-5-carboxylic acid; 2-(4-(6-((5-cyanothiophen-2-yl)methoxy)pyridin-2-yl)-2,5-difluorobenzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(4-(6-((4-cyano-2-methylbenzyl)oxy)pyridin-2-yl)-2,5-difluorobenzyl)-4-methoxy-1- (oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(2,5-difluoro-4-(6-((2-methyl-2H-1,2,3-triazol-4-yl)methoxy)pyridin-2-yl)benzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(4-(6-((4-(1H-1,2,4-triazol-1-yl)benzyl)oxy)pyridin-2-yl)-2,5-difluorobenzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(2,5-difluoro-4-(6-(isoxazol-3-ylmethoxy)pyridin-2-yl)benzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(4-(6-((4-cyano-2-methoxybenzyl)oxy)pyridin-2-yl)-2,5-difluorobenzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(2,5-difluoro-4-(6-((1-methyl-1H-pyrazol-3-yl)methoxy)pyridin-2-yl)benzyl)-4- methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; 2-(2,5-difluoro-4-(6-((2-methyl-2H-tetrazol-5-yl)methoxy)pyridin-2-yl)benzyl)-4-methoxy-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylic acid; or a pharmaceutically acceptable salt thereof. 30435_OUS -45-
4. A pharmaceutical composition comprising a compound, or a pharmaceutically acceptable salt thereof, according to any one of claims 1 to 3 and at least one pharmaceutically acceptable carrier, diluent, or excipient.
5. A compound, or a pharmaceutically acceptable salt thereof, according to any one of claims 1 to 3 for use in therapy.
6. A compound, or a pharmaceutically acceptable salt thereof, according to any one of claims 1 to 3 for use in the treatment of type II diabetes mellitus.
7. A compound, or a pharmaceutically acceptable salt thereof, according to any one of claims 1 to 3 for use in lowering blood glucose levels.
8. A compound, or a pharmaceutically acceptable salt thereof, according to any one of claims 1 to 3 for use in the treatment of hyperglycemia.
9. A compound, or a pharmaceutically acceptable salt thereof, according to any one of claims 1 to 3 for use in the treatment of obesity.
IL320810A 2022-11-16 2023-11-15 Glucagon-like peptide 1 agonists IL320810A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202263425751P 2022-11-16 2022-11-16
PCT/US2023/079720 WO2024107781A1 (en) 2022-11-16 2023-11-15 Glucagon-like peptide 1 receptor agonists

Publications (1)

Publication Number Publication Date
IL320810A true IL320810A (en) 2025-07-01

Family

ID=89378473

Family Applications (1)

Application Number Title Priority Date Filing Date
IL320810A IL320810A (en) 2022-11-16 2023-11-15 Glucagon-like peptide 1 agonists

Country Status (13)

Country Link
EP (1) EP4619098A1 (en)
JP (1) JP2025538389A (en)
KR (1) KR20250085816A (en)
CN (1) CN120344520A (en)
AU (1) AU2023379473A1 (en)
CL (1) CL2025001423A1 (en)
CO (1) CO2025005958A2 (en)
CR (1) CR20250178A (en)
DO (1) DOP2025000110A (en)
IL (1) IL320810A (en)
JO (1) JOP20250110A1 (en)
MX (1) MX2025005718A (en)
WO (1) WO2024107781A1 (en)

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MX2025005718A (en) 2025-06-02
EP4619098A1 (en) 2025-09-24
JP2025538389A (en) 2025-11-28
WO2024107781A1 (en) 2024-05-23
AU2023379473A1 (en) 2025-05-15
CL2025001423A1 (en) 2025-08-08
DOP2025000110A (en) 2025-06-15
JOP20250110A1 (en) 2025-05-13
CR20250178A (en) 2025-06-06
CN120344520A (en) 2025-07-18
KR20250085816A (en) 2025-06-12
CO2025005958A2 (en) 2025-05-29

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