195628-18-3

Upstream product

• 39478-61-0 (±)-cis-1-benzyl-4-(hydroxymethyl)piperidin-3-ol 
• 39478-61-0 trans-1-(phenylmethyl)-4-(hydroxymethyl)piperidin-3-ol 
• 219975-81-2 1,1-dimethylethyl (trans)-3-hydroxy-4-(hydroxy-methyl)-1-piperidinecarboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 138022-91-0 tert-butyl 4-(methoxymethylene)piperidine-1-carboxylate 
• 203663-26-7 t-butyl 4-(hydroxymethyl)-3,6-dihydropyridine-1(2H)-carboxylate 
• 39478-61-0 1-benzyl-3-hydroxy-4-hydroxymethylpiperidine 
• 219975-81-2 tert-butyl(3S,4S)-3-hydroxy-4-(hydroxymethyl)piperidine-1-carboxylate 
• 158984-76-0 1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinemethanol 
• 21472-88-8 5-hydroxy-6-oxo-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid ethyl ester 
• 39478-61-0 trans-1-(phenyl-methyl)-3-hydroxy-4-piperidinemethanol 
• 52763-21-0 ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride 
• 41632-40-0 (±)-cis-1-benzyl-4-(acetyloxymethyl)piperidin-3-yl acetate 

Downstream Products

• 219975-81-2 1,1-dimethylethyl trans-3-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate 
• 219975-81-2 1,1-dimethylethyl (trans)-3-hydroxy-4-(hydroxy-methyl)-1-piperidinecarboxylate 
• 39478-61-0 trans-1-(phenyl-methyl)-3-hydroxy-4-piperidinemethanol 
• 39478-61-0 (-)-(3S,4S)-3-hydroxy-1-(phenylmethyl)piperidine-4-methanol 
• 219975-81-2 rel-tert-Butyl (3R,4R)-3-hydroxy-4-(hydroxymethyl)piperidine-1-carboxylate 
• 219975-81-2 (trans)-tert-butyl 3-hydroxy-4-(hydroxymethyl)piperidine-1-carboxylate 
• 220218-58-6 tert-butyl 3-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate 
• 219975-81-2 (±)-cis-tert-butyl 1-[4-(hydroxymethyl)piperidin-3-ol-1-yl] carboxylate 

Relevant academic research and scientific papers

Aza-C-nucleosides as a new class of nucleosides

The synthesis of a new type of nucleoside analogue, aza-C-nucleosides, has been accomplished by the reaction of a number of hydroxylated piperidine and pyrrolidine derivatives with 5-bromouracil in pyridine. The conversion of the aza sugar (+)-cis-N-benzyl-4-hydroxymethylpiperidin-3-ol ((±)-5a) into (±)-5b with trans-configuration was accomplished in five steps by successive tritylation, mesylation, S(N)2 reaction with sodium acetate, deacetylation by treatment with sodium methoxide to give (±)-9 and finally detritylation with 80% acetic acid to give (±)-5b.

COMPOUNDS ACTIVE TOWARDS NUCLEAR RECEPTORS

Disclosed are compounds active towards nuclear receptors, pharmaceutical compositions containing the compounds and use of the compounds in therapy.

COMPOUNDS ACTIVE TOWARDS NUCLEAR RECEPTORS

Disclosed are compounds active towards nuclear receptors, pharmaceutical compositions containing the compounds and use of the compounds in therapy.

Design, Synthesis, and Monoamine Oxidase Inhibitory Activity of (+)-Cinchonaminone and Its Simplified Derivatives

The absolute structure of an indole alkaloid (+)-cinchonaminone by total synthesis of both (+)-cinchonaminone and its enantiomer was determined. The main focus of the study was the enantioselective synthesis of both enantiomers of a chiral cis-3,4-disubstituted piperidine. We also evaluated monoamine oxidase (MAO) inhibitory activities of these enantiomers. Furthermore, its structurally simplified derivatives were synthesized that did not have any chiral center. Two of these derivatives showed stronger MAO inhibitory activities than that of (+)-cinchonaminone.

Radiolabelling of 1,4-disubstituted 3-[18F]fluoropiperidines and its application to new radiotracers for NR2B NMDA receptor visualization

In order to develop a novel and useful building block for the development of radiotracers for positron emission tomography (PET), we studied the radiolabelling of 1,4-disubstituted 3-[18F]fluoropiperidines. Indeed, 3-fluoropiperidine became a useful building block in medicinal chemistry for the pharmacomodulation of piperidine-containing compounds. The radiofluorination was studied on substituted piperidines with electron-donating and electron-withdrawing N-substituents. In the instance of electron-donating N-substituents such as benzyl or butyl, configuration retention and satisfactory fluoride-18 incorporation yields up to 80% were observed. In the case of electron-withdrawing N-substituents leading to carbamate or amide functions, the incorporation yields depend on the 4-susbtitutent (2 to 63%). The radiolabelling of this building block was applied to the automated radiosynthesis of NR2B NMDA receptor antagonists and effected by a commercially available radiochemistry module. The in vivo evaluation of three radiotracers demonstrated minimal brain uptakes incompatible with the imaging of NR2B NMDA receptors in the living brain. Nevertheless, moderate radiometabolism was observed and, in particular, no radiodefluorination was observed which demonstrates the stability of the 3-position of the fluorine-18 atom. In conclusion, the 1,4-disubstituted 3-[18F]fluoropiperidine moiety could be of value in the development of other radiotracers for PET even if the evaluation of the NR2B NMDA receptor antagonists failed to demonstrate satisfactory properties for PET imaging of this receptor.

Radiolabelling of 1,4-disubstituted 3-[18F]fluoropiperidines and its application to new radiotracers for NR2B NMDA receptor visualization

In order to develop a novel and useful building block for the development of radiotracers for positron emission tomography (PET), we studied the radiolabelling of 1,4-disubstituted 3-[18F]fluoropiperidines. Indeed, 3-fluoropiperidine became a useful building block in medicinal chemistry for the pharmacomodulation of piperidine-containing compounds. The radiofluorination was studied on substituted piperidines with electron-donating and electron-withdrawing N-substituents. In the instance of electron-donating N-substituents such as benzyl or butyl, configuration retention and satisfactory fluoride-18 incorporation yields up to 80% were observed. In the case of electron-withdrawing N-substituents leading to carbamate or amide functions, the incorporation yields depend on the 4-susbtitutent (2 to 63%). The radiolabelling of this building block was applied to the automated radiosynthesis of NR2B NMDA receptor antagonists and effected by a commercially available radiochemistry module. The in vivo evaluation of three radiotracers demonstrated minimal brain uptakes incompatible with the imaging of NR2B NMDA receptors in the living brain. Nevertheless, moderate radiometabolism was observed and, in particular, no radiodefluorination was observed which demonstrates the stability of the 3-position of the fluorine-18 atom. In conclusion, the 1,4-disubstituted 3-[18F]fluoropiperidine moiety could be of value in the development of other radiotracers for PET even if the evaluation of the NR2B NMDA receptor antagonists failed to demonstrate satisfactory properties for PET imaging of this receptor.

PIPERIDINE-CONTAINING COMPOUNDS AND USE THEREOF

A method for preventing and/or treating a metabolic disease, cerebrovascular disease, etc. which comprises administering to a mammal an effective amount of the compound of the formula (I) wherein all symbols have the same meanings as defined in the specification; a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrug thereof. And a novel compound of the formula (I-1): wherein all symbols have the same meanings as defined in the specification; a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrug thereof has an anti-diabetic effect and a neuroprotective effect. Accordingly, the compound of the formula (I) and the compound of the formula (I-1) are useful in a method for preventing and/or treating for a metabolic disease such as diabetes, cerebrovascular disease such as stroke, etc.

Development of two diastereoselective routes towards trans-4-aminomethyl-piperidin-3-ol building blocks

Two diastereoselective, scaleable routes towards trans-3,4-disubstituted piperidines with a 4-hydroxymethyl-3-hydroxy or 4-aminomethyl-3-hydroxy substitution pattern are being described. In the first route, the 3,4-trans configuration was introduced regio- and diastereoselectively via a hydroboration/oxidation sequence starting from 4-hydroxymethylpyridine. In the second route, regioselective epoxide ring opening of N-benzyl-3,4-epoxy-piperidine was achieved with LiCN, in situ generated from acetocyanohydrin and LiNH2. The regioselectivity of both the hydroboration and the epoxide ring opening was positively influenced by the presence of the basic piperidine nitrogen. Both routes have been optimized to be performed at large scale.

QUINOLONE ANTIBACTERIAL AGENTS

Compounds of formula (I, II, III, IV, V, and VI) and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula (I) as well as pharmaceutically acceptable compositions comprising compounds of formula (I). Compounds of formula (I) as disclosed herein can be used in a variety of applications including use as antibacterial agents.

Synthesis and pharmacological evaluation of benzamide derivatives as selective 5-HT4 receptor agonists

It is thought that selective 5-HT4 receptor agonists-such as 4-amino-5-chloro-2-methoxy-N-[1-(6-oxo-6-phenylhexyl)piperidin-4-ylmethyl] benzamide (2)-have the ability to enhance both upper and lower gastrointestinal motility without any significant adverse effects. Modification of 2 was performed. Variation of the piperidin-4-ylmethyl moiety of 2 led to a decrease in the binding affinity for the 5-HT4 receptor. Following conversion of the carbonyl group on the benzoyl part to a hydroxyl or sulfoxide group, the binding affinity for the 5-HT4 receptor was retained although the effect on defecation was reduced. Many of the 4-amino-5-chloro-2-methoxy-N- (piperidin-4-ylmethyl)benzamides that had a ether or sulfide moiety in the side-chain part at the 1-position of the piperidine exhibited high affinity for the 5-HT4 receptor. Among these, phenylthio 41c and benzylthio derivative 44 were selective 5-HT4 receptor agonists, and had a similar effect on defecation to compound 2.