49637-20-9

Usage

Chemical composition

A hydrochloride salt of piperidinepentanoic acid, which is a derivative of piperidine, a six-membered heterocyclic ring compound.

Primary use

Primarily used as a reagent in chemical reactions and as a precursor in the synthesis of other compounds.

Pharmaceutical application

Commonly used in the pharmaceutical industry for the production of drugs such as the antiepileptic medication, levetiracetam.

Research and development

Utilized in research and development for the creation of new pharmaceutical compounds and in the synthesis of other organic chemicals.

Value in organic chemistry

1-Piperidinepentanoic acid, hydrochloride is a valuable intermediate in organic chemistry.

Wide range of applications

This chemical can be used in a variety of applications, making it a versatile compound in the field of chemistry.

Upstream product

• 62522-24-1 ethyl 5-piperidinevalerate 
• 14660-52-7 ethyl 5-bromovalerate 
• 110-89-4 piperidine 
• 14273-86-0 methyl 5-chloropentanoate 
• 49637-19-6 5-piperidin-1-yl-pentanoic acid methyl ester 

Downstream Products

• 160845-84-1 1-(4-amino-5-chloro-2-methoxy-phenyl)-5-(piperidin-1-yl)pentan-1-one 
• 864914-14-7 5-piperidin-1-yl-pentanoic acid-(2-amino-5-cyano-phenyl)-amide 

Relevant academic research and scientific papers

Conformational analysis of 5-piperidinevaleric acid, 5-(N- methylpiperidine)valerate and their hydrogen halides by MO calculations, X- ray, diffraction and FTIR spectroscopy

The most stable conformers of 5-(piperidine)valeric acid (1), 5-(N- methylpiperidine)valerate (2) and their hydrogen halides (3 and 4) were analyzed by the semiempirical PM3 method and selected compounds by the B3LYP/6-31G(d,p) method. As some of the investigated compounds are charged and the others can be neutral, some have acidic proton, others do not. They are capable of forming ionic bonds (via Coulombic attraction between the oppositely charged groups) or of forming the various types of hydrogen bonded conformers. As a result these compounds are ideally suited to study the importance of electrostatic interactions and hydrogen bonding on the relative stabilities of conformers. In the case of compounds containing N- methylpiperidine unit, for a particular conformer, the intramolecular attractive electrostatic interactions between the charged group play key roles in their relative stability in the gas phase. The electrostatic interaction of the X- ion with the positively charged nitrogen atom decreases their proton-acceptor properties and COOH···X- hydrogen bonds are present in all hydrogen halides (3). 5-Piperidine valeric acid with HF forms a molecular complex, while with HCl, HBr and HI an ion pair, according to the B3LYP calculations. The PM3 calculations predict a molecular complex also with HCl. The crystal structure of 5-(piperidine)valeric acid hydrogen bromide (4HBr), space group of crystals P21/n with a = 6.204(1), b = 32.777(7), c = 6.416(1) A, β = 106.21(3)°, Z = 4 and R = 0.0685 was characterized by X-ray crystallography methods. Br- ion forms two types of hydrogen bonds: Br···N(1), 3.247(14) A, and O(1) ···Br, 3.118(11) A. Moreover, C-H···Br short contacts, which can be recognized as weak hydrogen bonds, exist in the crystal. The FTIR spectrum of 1 in the solid state shows an intense broad absorption in the 1600-400 cm-1 region typical for a very short NHO hydrogen bonds. In solution the hydrogen bond seems to be longer. The bands of vC=O at 1708 cm-1 and v(as)COO- at 1615 cm-1 in CD3CN solution show that OH···N ? O-···HN+ equilibrium exists. Ab initio calculations predict molecular structures of three most stable conformers of 1 in the gas phase.

MODIFIED DRUGS FOR USE IN LIPOSOMAL NANOPARTICLES

Drag derivatives are provided herein which are suitable for loading into liposomal nanoparticle carriers. In some preferred aspects, the derivatives comprise a poorly water-soluble drag derivatized with a weak-base moiety that facilitates active loading of the drag through a LN transmembrane pH or ion gradient into the aqueous interior of the LN. The weak-base moiety can optionally comprise a lipophilic domain that facilitates active loading of the drag to the inner monolayer of the liposomal membrane. Advantageously, LN formulations of the drag derivatives exhibit improved solubility, reduced toxicity, enhanced efficacy, and/or other benefits relative to the corresponding free drags.

Discovery of a novel alpha-7 nicotinic acetylcholine receptor agonist series and characterization of the potent, selective, and orally efficacious agonist 5-(4-acetyl[1,4]diazepan-1-yl)pentanoic acid [5-(4-methoxyphenyl)-1H- pyrazol-3-yl] amide (SEN15924, WAY-361789)

Alpha-7 nicotinic acetylcholine receptors (α7 nAChR) are implicated in the modulation of many cognitive functions such as attention, working memory, and episodic memory. For this reason, α7 nAChR agonists represent promising therapeutic candidates for the treatment of cognitive impairment associated with Alzheimer's disease (AD) and schizophrenia. A medicinal chemistry effort, around our previously reported chemical series, permitted the discovery of a novel class of α7 nAChR agonists with improved selectivity, in particular against the α3 receptor subtype and better ADME profile. The exploration of this series led to the identification of 5-(4-acetyl[1,4] diazepan-1-yl)pentanoic acid [5-(4-methoxyphenyl)-1H-pyrazol-3-yl] amide (25, SEN15924, WAY-361789), a novel, full agonist of the α7 nAChR that was evaluated in vitro and in vivo. Compound 25 proved to be potent and selective, and it demonstrated a fair pharmacokinetic profile accompanied by efficacy in rodent behavioral cognition models (novel object recognition and auditory sensory gating).

BASIC AMINE COMPOUND AND USE THEREOF

Novel amine compounds which are represented by the following formula (1) and efficacious against diseases such as a viral infectious disease with HIV, rheumatism, and cancer metastasis; typically, A 1 and A 2 represent a hydrogen atom or a substitutable monocyclic or polycyclic heteroaromatic ring and W represents a substitutable benzene ring or any group represented by the following formula (10) or (11): where X represents O, CH 2 , C(=O), NR 11 , or CHR 35 and D represents a group represented by the following formula (6): where Q represents a single bond, NR 12 , or a group represented by the formula (13): and Y represents a group represented by the following formula (7) : where z represents a substitutable monocyclic or polycyclic aromatic ring; and B represents -NR 25 R 26 ; and R 1 to R 26 in the above formulae represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.

Aqueous basicity and proton affinity of zwitterionic ω-(N-methylpiperidine)-alkanocarboxylates and ω-(N-piperidine)-alkanocarboxylic acids

The pK a values of 5 ω-(N-methylpiperidine)-alkanocarboxylates (N-methylpiperidine betaines) and 5 ω-(N-piperidine)-alkanocarboxylic acid were determined by potentiometric titration of their hydrohalides with KOH. Semiempirical geometry optimizations were performed for gaseous betaines. Four conformers were characterized and their PA values estimated. The PA values fulfilled the linear correlation with the aqueous pKa values estimated in ref. 1. A linear correlation between the calculated heat of formation (ΔHt) and the sum of the N...O1 and N...O2 distances, for the conformers containing the same number of CH2 groups, indicates that they are stabilized by the intramolecular electrostatic interactions between the positively charged nitrogen atom and oxygen atoms of the carboxylate group.

Heterocyclic esters of alkylphenyl benzopyranopyridines

Heterocyclic esters of alkylphenyl benzopyranopyridines represented by the formula STR1 wherein R1 is hydrogen, loweralkyl, loweralkanoyl, cycloalkylloweralkyl, cycloalkylloweralkanoyl, loweralkenyl, loweralkynyl, haloloweralkenyl, phenylloweralkyl, phenylloweralkenyl or phenylloweralkynyl; R2 is loweralkyl; R3 is STR2 WHEREIN X is a straight or branched chain alkylene group having from one to eight carbon atoms, a is an integer from 1 to 4, b is an integer from 1 to 4 and Z is CH2, O, S or NR7, with R7 being hydrogen or loweralkyl, with the limitation that when X is O, S or NR7, the sum of a and b is 3 or 4; and R8 is hydrogen or loweralkyl; Y is a straight or branched chain alkylene group having from one to ten carbon atoms; and each R4 and R5 and R6 are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl; and the pharmaceutically acceptable acid addition salts thereof.

Anesthesia methods using benzopyrans and esters thereof as pre-anesthesia medication

Improved anesthesia methods comprising pretreating a patient to be anesthetized with a benzopyran of formula I STR1 wherein, in the C ring, X is NR1, S, CH2 or STR2 R1 is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, loweralkanoyl, cycloalkyloweralkyl, cycloalkylloweralkanoyl, cycloalkyl, haloloweralkyl, haloloweralkenyl, phenylloweralkyl, phenyloweralkenyl or phenyloweralkylnyl; m is an integer from 0 to 3, n is an integer from 0 to 3 and n + m = 2 or 3; or the C ring is quinuclidine ring STR3 R2 is loweralkyl; R3 is hydrogen or STR4 wherein Y is a straight or branched chain alkylene group having from one to eight carbon atoms, a is an integer from 1 to 4, b is an integer from 1 to 4, Z is CH2, O, S or NR6, R6 being hydrogen or loweralkyl, with the limitation that when Z is O, S or NR5, the sum of a and b is 3 or 4, and R5 is hydrogen or loweralkyl; R4 is C1 -C20 straight or branched chain alkyl, cycloalkyl, or STR5 wherein Y is a straight or branched chain alkylene group having from one to ten carbon atoms, and each R7, R8 and R9 are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl; and the pharmaceutically acceptable salts thereof, with the limitation that when X is STR6 m = 2 and n = 2, R3 cannot be hydrogen.

Novel heterocyclic esters of benzopyranopyridines

Novel heterocyclic esters of benzopyranopyridines represented by the formula STR1 wherein R1 is hydrogen, lower alkyl, lower alkanoyl, cycloalkyl-lower alkyl, cycloalkyl-lower alkanoyl, lower alkenyl, lower alkynyl, halo-loweralkenyl, phenyl-lower alkyl, phenyl-lower alkenyl or phenyl-lower alkynyl; R2 is lower alkyl; R3 is an alkyl having one to twenty carbon atoms or a cycloalkyl-lower alkyl, Y is a straight or branched chain alkylene having one to eight carbon atoms, and R4 is a group of the formula STR2 a is an integer from 1 to 4, b is an integer from 1 to 4 and X is CH2, O, S or N--R5 with R5 being hydrogen or lower alkyl, with the limitation that when X is O, S or N--R5, a and b each must be 2 and R6 is hydrogen or a lower alkyl group bonded to a carbon in the ring; and the acid addition salts thereof.

Heterocyclic esters of benzopyranopyridines

Novel heterocyclic esters of benzopyranopyridines represented by the formula SPC1 Wherein R1 is hydrogen, lower alkyl, lower alkanoyl, cycloalkyl-lower alkyl, cycloalkyl-lower alkanoyl, lower alkenyl, lower alkynyl, halo-loweralkenyl, phenyl-lower alkyl, phenyl-lower alkenyl or phenyl-lower alkynyl; R2 is lower alkyl; R3 is an alkyl having one to twenty carbon atoms or a cycloalkyl-lower alkyl, Y is a straight or branched chain alkylene having one to eight carbon atoms, and R4 is a group of the formula EQU1 a is an integer from 1 to 4, b is an integer from 1 to 4 and X is CH2, O, S or N--R5 with R5 being hydrogen or lower alkyl, with the limitation that when X is O, S or N--R5, a and b each must be 2 and R6 is hydrogen or a lower alkyl group bonded to a carbon in the ring; and the acid addition salts thereof.