67853-64-9Relevant academic research and scientific papers
Characterization of tunable piperidine and piperazine carbamates as inhibitors of endocannabinoid hydrolases
Long, Jonathan Z.,Jin, Xin,Adibekian, Alexander,Li, Weiwei,Cravatt, Benjamin F.
experimental part, p. 1830 - 1842 (2010/08/19)
Monoacylglycerol lipase (MAGL) and fatty acid amide hydrolase (FAAH) are two enzymes from the serine hydrolase superfamily that degrade the endocannabinoids 2-arachidonoylglycerol and, anandamide, respectively. We have recently discovered that, MAGL and, FAAH are both inhibited by carbamates bearing an N-piperidine/piperazine group. Piperidine/piperazine carbamates show excellent in vivo activity, raising brain endocannabinoid levels and producing CB1-dependent behavioral effects in mice, suggesting that they represent a promising class of inhibitors for studying the endogenous functions of MAGL and FAAH. Herein, we disclose a full account of the syntheses, structure-activity relationships, and, inhibitory activities of piperidine/piperazine carbamates against members of the serine hydrolase family. These scaffolds can be tuned for MAGL-selective or dual MAGL-FAAH inhibition by the attachment of an, appropriately substituted bisarylcarbinol or aryloxybenzyl moiety, respectively, on the piperidine/piperazine ring. Modifications to the piperidine/piperazine ring ablated inhibitory activity, suggesting a strict requirement for a six-membered ring to maintain potency.
4-[(diaryl)hydromethyl]-1-piperidinealkanols and esters and carbamates thereof useful in the treatment of allergic disorders
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, (2008/06/13)
Novel compounds of the formula: STR1 are disclosed wherein Ar and Ar1 are phenyl, sustituted phenyl or pyridinyl, "alk" is a C1 -C12 straight or branched hydrocarbon chain, and R is H, loweralkylcarbonyl, arylcarbonyl, or aminocarbonyl where the amino is unsubstituted or substituted by one or two groups selected from loweralkyl or aryl. The compounds of this invention are useful in the treatment of allergic disorders.
4-[diaryl)hydroxymethyl]-1-piperidinealkylcarboxylic acids, salts and esters useful in the treatment of allergic disorders
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, (2008/06/13)
Novel compounds useful in the treatment of allergic disorders and having the formula: STR1 where Ar and Ar1 are pyridinyl, phenyl, or substituted phenyl and where Y is --OH,--O? M≈ m,--O--loweralkyl, --O--Aryl, or NR1 R2 (R1, R2 =H, loweralkyl, aryl) are herein disclosed.
Arylalkylheterocyclic amines,N-substituted by aryloxyalkyl group in a method for allergy treatment
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, (2008/06/13)
A method of inhibiting Type 1 allergic responses in a living animal body with substituted heterocyclic amines is disclosed wherein the active agents are expressed generally by the formula which includes certain known and certain known compounds: STR1 wherein P is zero, one or two; m is one to six inclusive; A is selected from hydrogen, hydroxy or cyano; d is zero or one; Q is --CH--, CH2 -- or STR2 n is zero or one and when Q is --CH-- and n is one, a double bond is formed with one of the adjacent carbons but not both at the same time, and when n and d are zero at the same time, a double bond is formed between the α carbon and a carbon of the central heterocyclic amine ring; Ar, D and R are selected from phenyl, substituted phenyl, pyridinyl, thienyl, furanyl or naphthyl and in addition, R may have the values benzyl, substituted benzyl, cycloalkyl or loweralkyl and D may additionally have the values: 2H-1-benzopyran-2-one,4-oxo-4H-1-benzopyran-2-carboxylic acid loweralkyl ester, 2,3-dihydro-4H-1-benzopyran-4-one, 1,4-benzodioxanloweralkyl-2-yl or 1,1'-biphenyl-4-yl and the pharmaceutically acceptable salts thereof.
Synthesis and Antiallergy Activity of 4-(Diarylhydroxymethyl)-1-piperidines and Structurally Related Compounds
Walsh, David A.,Franzyshen, Stephen K.,Yanni, John M.
, p. 105 - 118 (2007/10/02)
A series of 4-(diarylhydroxymethyl)-1-piperidines was synthesized and evaluated for antiallergy activity.Several analogues had potent activity in the passive foot anaphylaxis (PFA) assay, an IgE-mediated model useful in the detection of compounds possessing antiallergic activity.In particular 1--1-piperidinyl>propoxy>-3-methoxyphenyl>ethanone (1, AHR-5333) was more potent than oxatomide and terfenadine in this assay.
4-[(α,α-diaryl)-hydroxymethyl]-1-piperidinylalkyl-cyclic carbamate derivatives as allergic response inhibitors
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, (2008/06/13)
4-[(α,α-Diaryl)-hydroxymethyl]-1-piperidinylalkylcyclic carbamate derivatives having the formula: STR1 wherein; R is hydrogen, loweralkyl, cycloalkyl, phenyl and substituted phenyl; Ar and Ar1 are phenyl, substituted phenyl or pyridinyl; alk is a straight or branched hydrocarbon chain; R1 is loweralkyl substituted for hydrogen on a ring carbon. The compounds are useful antihistamines and in controlling allergic response.
