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Fused Bicyclic Nitrogen-Containing Heterocycles

a technology of bicyclic nitrogen and heterocycles, which is applied in the field of fused bicyclic nitrogen-containing heterocycles, can solve the problems of often adverse effects of hypertriglyceridemia

Inactive Publication Date: 2007-10-18
JAPAN TOBACCO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides fused bicyclic nitrogen-containing heterocyclic compounds that can be used to treat or prevent conditions associated with DGAT in animals, particularly humans. These compounds have shown promising results in animal studies and are expected to have improved efficacy and safety compared to existing drugs. The patent also includes pharmaceutical compositions and methods for using these compounds for treating or preventing various metabolic disorders.

Problems solved by technology

Additionally, hypertriglyceridemia is often an adverse consequence of cancer therapy (see, Bast, et al.

Method used

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  • Fused Bicyclic Nitrogen-Containing Heterocycles
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  • Fused Bicyclic Nitrogen-Containing Heterocycles

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0129] This example illustrates the preparation of the compound designated Ex. 1.

[0130] To a suspension of 4,5-diamino-6-hydroxypyrimidine (1.0 g, 7.93 mmol) and 4-bromophenacyl bromide (2.2 g, 7.93 mmol) in EtOH (20 mL) was added NaHCO3 (666 mg, 7.93 mmol), and the mixture was stirred for 1.5 h at 80° C. After cooling, the reaction mixture was concentrated, and the residue was diluted with CHCl3 (40 mL). After filtration of insoluble material, the filtrate was concentrated. The residue was triturated with toluene to give the desired compound Ex. 1 (840 mg) as a pale yellow crystal, m.p.: >200° C. IR (cm−1): 3291, 3145, 1634, 1586. MS (ESI+): 305, 307 (100). 1H NMR(DMSO-d6, 400 MHz): 5.44 (s, 2H), 7.10 (br s, 2H), 7.69 (d, 2H, J=8.6 Hz), 7.93 (s, 1H), 8.03 (d, 2H, J=8.6 Hz).

example 1-2 to 1-37

[0131] The compounds shown in Table 1 were obtained in the same manner as in Example 1.

example 2

[0132] This example illustrates the preparation of the compound designated Ex. 2.

[0133] a)

[0134] At 0° C., to a solution of triethyl phosphonoacetate (2.6 mL, 12.91 mmol) in DMF (5.5 mL), sodium hydride (60% in oil, 517 mg, 12.91 mmol) was added portionwise, and the reaction mixture was stirred at room temperature for 30 min. A solution of 4-phenylcyclohexanone in DMF (2.0 mL) was added. After stirring for 0.5 h, the mixture was poured into 5% aq. KHSO4 (10 mL) and extracted with diethyl ether (10 mL). The organic layer was successively washed with water (5 mL) and brine (5 mL), dried over MgSO4 and concentrated. The residue was purified by column chromatography (hexane / AcOEt=7 / 1) to give compound 2 (2.0 g) as colorless oil.

[0135] b)

[0136] To a stirred solution of 2 (500 mg, 2.05 mmol) in EtOH (5 mL) was added 10% Pd / C (50 mg). The mixture was stirred at room temperature for 1 h under an atmospheric pressure of hydrogen. The catalyst was removed by filtration, and the filtrate...

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Abstract

Compounds, pharmaceutical compositions and methods that are useful in the treatment or prevention of metabolic and cell proliferative diseases or conditions are provided herein. In particular, the invention provides compounds which modulate the activity of proteins involved in lipid metabolism and cell proliferation.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application is a divisional of U.S. patent application Ser. No. 10 / 720,844, filed Nov. 21, 2003, which claims the benefit of U.S. Provisional Patent Application No. 60 / 428,600, filed Nov. 22, 2002, all of which are hereby incorporated by reference.BACKGROUND OF THE INVENTION [0002] Triglycerides represent the major form of energy stored in eukaryotes. Disorders or imbalances in triglyceride metabolism are implicated in the pathogenesis of and increased risk for obesity, insulin resistance syndrome and type II diabetes, nonalcoholic fatty liver disease and coronary heart disease (see, Lewis, et al, Endocrine Reviews (2002) 23:201 and Malloy and Kane, Adv Intern Med (2001) 47:111). Additionally, hypertriglyceridemia is often an adverse consequence of cancer therapy (see, Bast, et al. Cancer Medicine, 5th Ed., (2000) B. C. Decker, Hamilton, Ontario, Calif.). [0003] A key enzyme in the synthesis of triglycerides is acyl CoA:diacylglyce...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/55A61K31/542A61K31/5383C07D497/02C07D498/02C07D491/02A61K31/519A61K31/538C07D491/04C07D498/04C07D498/10C07D498/16
CPCC07D491/04A61P1/04A61P1/14A61P1/16A61P1/18A61P11/00A61P13/08A61P13/10A61P13/12A61P15/00A61P17/00A61P19/06A61P25/00A61P3/04A61P35/00A61P35/02A61P3/06A61P3/08A61P43/00A61P7/00A61P9/02A61P9/04A61P9/10A61P9/12A61P9/14A61P3/10C07D498/04C07D491/052C07D513/04
Inventor FOX, BRIANFURUKAWA, NOBORUHAO, XIAOLINIIO, KIYOSEIINABA, TAKASHIJACKSON, SIMONKAYSER, FRANKLABELLE, MARCLI, KEXUEMATSUI, TAKUYAMCMINN, DUSTINOGAWA, NOBUYARUBENSTEIN, STEVENSAGAWA, SHOICHISUGIMOTO, KAZUYUKISUZUKI, MASAHIROTANAKA, MASAHIROYE, GUOSENYOSHIDA, ATSUHITOZHANG, JIAN
Owner JAPAN TOBACCO INC
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