Inhibitors of fatty acid amide hydrolase

Details Inhibitors of fatty acid amide hydrolase Inhibitors of fatty acid amide hydrolase

2005-05-10

2005-05-10

Dentz, Bernard (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C544S184000, C544S236000, C544S255000, C544S350000, C548S180000, C548S217000, C548S218000, C548S309400

Reexamination Certificate

active

06891043

ABSTRACT:
Potent inhibitors of fatty acid amide hydrolase (FAAH) are constructed having K1's below 200 pM and activities 102-103times more potent than the corresponding trifluoromethyl ketones. The potent inhibitors combine several features, viz.: 1.) an α-keto heterocylic head group; 2.) a hydrocarbon linkage unit employing an optimal C12-C8 chain length; and 3.) a phenyl or other π-unsaturation corresponding to the arachidonyl Δ8,9/Δ11,12and/or oleyl Δ9,10positions. A preferred α-keto heterocylic head group is α-keto N4 oxazolopyridine, with incorporation of a second weakly basic nitrogen. Fatty acid amide hydrolase is an enzyme responsible for the degradation of oleamide (an endogenous sleep-inducing lipid) and anandamide (an endogenous ligand for cannabinoid receptors).

REFERENCES:
Chemical Abstracts Online, Registry No. 76115-66-7.*
Chemical Abstracts Online, Registry No. 225108-75-5.*
Chemical Abstracts Online, Registry No. 115951-83-2.*
Chemical Abstracts Online,Registry No. 38866-32-9.*
Chem. Abstracts Online, Registry No. 37547-85-6.*
Chem. Absracts Onlinem Registry No. 27411-62-7.*
Chemical Abstracts Online, Registry No. 76115-66-7.
Chemical Abstracts Online, Registry No. 225108-72-5.
Chemical Abstracts Online, Registry No. 115951-83-2.
Chemical Abstracts Online, Registry No. 38866-32-9.
Chemical Abstracts Online, Registry No. 37547-85-6.
Chemical Abstracts Online, Registry No. 27411-62-7.

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