Imidazopyridine compounds

• US 8,124,617 B2
• Filed: 09/01/2006
• Issued: 02/28/2012
• Est. Priority Date: 09/01/2005
• Status: Expired due to Fees

• Current Assignee: Takeda San Diego, Inc. (Takeda Pharmaceutical Company Limited)
• Original Assignee: Takeda Pharmaceutical Company Limited, Takeda San Diego, Inc. (Takeda Pharmaceutical Company Limited)
• Inventors: Iwata, Hidehisa, Kohara, Yasuhisa, Cao, Sheldon X., Guntupalli, Prasuna, Gwaltney, Stephen L., Hosfield, David J., Liu, Yan, Stafford, Jeffrey A, Wolgast, Beverly
• Primary Examiner(s): Andres, Janet
• Assistant Examiner(s): Rahmani, Niloofar
• Application Number:
  US12/065,607
• Publication Number:
  US 20100069431A1
• Time in Patent Office: 2,006 Days
• Field of Search: 514/303, 546/118
• US Class Current: 514/303
• CPC Class Codes: A61K 31/437 the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
• CPC Class Codes: A61K 9/2018 Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
• CPC Class Codes: A61K 9/4858 Organic compounds
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/02 Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 1/12 Antidiarrhoeals
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 1/18 for pancreatic disorders, e.g. pancreatic enzymes
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 13/02 of urine or of the urinary tract, e.g. urine acidifiers
• CPC Class Codes: A61P 13/12 of the kidneys
• CPC Class Codes: A61P 15/00 Drugs for genital or sexual disorders for disorders of sex hormones A61P5/24; Contraceptives
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/06 Antigout agents, e.g. antihyperuricemic or uricosuric agents
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 21/04 for myasthenia gravis
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/02 : for peripheral neuropathies
• CPC Class Codes: A61P 25/26 : Psychostimulants, e.g. nicotine, cocaine
• CPC Class Codes: A61P 27/02 : Ophthalmic agents
• CPC Class Codes: A61P 27/12 : for cataracts
• CPC Class Codes: A61P 27/16 : Otologicals
• CPC Class Codes: A61P 29/00 : Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/04 : Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 3/06 : Antihyperlipidemics
• CPC Class Codes: A61P 3/10 : for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 31/00 : Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/18 : for HIV
• CPC Class Codes: A61P 35/00 : Antineoplastic agents
• CPC Class Codes: A61P 35/02 : specific for leukemia
• CPC Class Codes: A61P 37/04 : Immunostimulants
• CPC Class Codes: A61P 37/08 : Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 5/00 : Drugs for disorders of the endocrine system
• CPC Class Codes: A61P 5/28 : Antiandrogens
• CPC Class Codes: A61P 5/30 : Oestrogens
• CPC Class Codes: A61P 5/48 : of the pancreatic hormones
• CPC Class Codes: A61P 7/00 : Drugs for disorders of the blood or the extracellular fluid
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/04 : Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
• CPC Class Codes: A61P 9/08 : Vasodilators for multiple indications
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/12 : Antihypertensives
• CPC Class Codes: C07D 471/02 : in which the condensed system contains two hetero rings
• CPC Class Codes: C07D 471/04 : Ortho-condensed systems
• CPC Class Codes: C12N 9/1205 : Phosphotransferases with an alcohol group as acceptor (2.7.1), e.g. protein kinases
• CPC Class Codes: C12Y 207/01001 : Hexokinase (2.7.1.1)

Abstract

Compounds, pharmaceutical compositions, kits and methods are provided for use with glucokinase that comprise a compound selected from the group consisting of formula (I) wherein the variables are as defined herein.

Claims

1. A compound represented by the formula (II):

3. A pharmaceutical agent comprising a compound according to claim 1 and one or more pharmacologically acceptable carriers.

2. A compound selected from the group consisting of:

2-(3-(benzyloxy)-5-((1-methyl-1H-imidazol-2-yl)methoxy)phenyl)-3H-imidazo[4,5-b]pyridine;

2-(3-(benzyloxy)-5-((1-methyl-1H-imidazol-2-yl)methoxy)phenyl)-6-bromo-3H-imidazo[4,5-b]pyridine;

6-bromo-2-(3-((1-methyl-1H-imidazol-2-yl)methoxy)-5-(2-(thiophen-3-yl) ethoxy)phenyl)-3H-imidazo[4,5-b]pyridine;

2-(3-(2-fluorobenzyloxy)-5-((1-methyl-1H-imidazol-2y1)methoxy) phenyl)-3H-imidazo[4,5-b]pyridine;

6-chloro-2-(3-(2-fluorobenzyloxy)-5-((1-methyl-1H-imidazol-2-yl)methoxy)phenyl)-3H-imidazo[4,5-b]pyridine;

6-bromo-2-(3-(2-fluorobenzyloxy)-5-((1-methyl-1H-imidazol-2-yl)methoxy)phenyl)-3H-imidazo[4,5-b]pyridine;

3-(2-(3-(2-fluorobenzyloxy)-5-((1-methyl-1H-imidazol-2-yl)methoxy)phenyl)-3H-imidazo[4,5-b]pyridin-6-yl)propan-1-ol;

(R)-2-(3-(2-fluorobenzyloxy)-5-(1-methoxypropan-2-yloxy)phenyl)-3H-imidazo [4,5-b]pyridine;

(R)-6-chloro-2-(3-(2-fluorobenzyloxy)-5-(1-methoxypropan-2-yloxy) phenyl)-3H-imidazo[4,5-b]pyridine;

(R)-6-bromo-2-(3-(2-fluorobenzyloxy)-5-(1-methoxypropan-2-yloxy) phenyl)-3H-imidazo[4,5-b]pyridine;

(S)-3-(2-(3-(2-fluorobenzyloxy)-5-(1-methoxypropan-2-yloxy)phenyl)-3H-imidazo [4,5-b]pyridin-6-yl)propan-1 -ol;

(S)-methyl 2-(3-(2-fluorobenzyloxy)-5-(1-methoxypropan-2-yloxy) phenyl)-3H-imidazo[4,5-b] pyridine-6-carboxylate; and

(S)-2-(3 -(2-fluorobenzyloxy)-5 -(1-methoxypropan-2-yloxy)phenyl)-3H-imidazo [4,5-b]pyridine-6-carboxylic acid.