187679-58-9

Usage

Chemical classification

Piperidinecarboxylic acid derivative

Usage

Pharmaceutical industry for drug synthesis

Stereochemistry

(2S,3S)configuration

Biological activity

Importance due to stereochemistry

Potential applications

Development of new drugs for various medical conditions

Medicinal chemistry promise

Ability to target specific biological pathways and receptors in the human body

Upstream product

• 239437-22-0 (2S,3S)-3-Dibenzylamino-2-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 500021-57-8 (S)-3-[(E)-Methoxyimino]-2-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 562817-62-3 C₁₈H₂₄N₂O₄ 
• 191669-62-2 (S)-tert-butyl 3-carbonyl-2-phenylpiperidine-1-carboxylic acid 
• 159249-47-5 tert-butyl (2S,3S)-3-hydroxy-2-phenylpiperidine-1-carboxylate 
• 562817-61-2 (S)-1-(tert-butoxycarbonyl)-2-phenyl-3-piperidone oxime 
• 562817-59-8 (2S,3S)-3-hydroxy-1-(4-methoxybenzyl)-2-phenylpiperidine 
• 562817-58-7 (-)-(5S,6S)-5-hydroxy-1-(4-methoxybenzyl)-6-phenyl-5,6-dihydropyridin-2(1H)-one 
• 187679-57-8 tert-butyl (2S,3S)-3-({[2-(methyloxy)phenyl]methyl}amino)-2-phenylpiperidinecarboxylate 
• 1018989-20-2 C₁₆H₂₂N₄O₂ 
• 24424-99-5 di-tert-butyl dicarbonate 
• 81112-82-5 rendement diastéréoisomèrique 
• 100-52-7 benzaldehyde 
• 148701-46-6 cis-(3S)-hydroxy-(2S)-phenylpiperidine 

Downstream Products

• 187679-57-8 tert-butyl (2S,3S)-3-({[2-(methyloxy)phenyl]methyl}amino)-2-phenylpiperidinecarboxylate 
• 136982-36-0 (2S,3S)-3-(2-methoxybenzylamino)-2-phenylpiperidine 
• 145742-28-5 (2S,3S)-3-(2-methoxy-5-trifluoromethoxybenzyl)-amino-2-phenylpiperidine 
• 187679-68-1 (2S,3S)-1-tert-butoxycarbonyl-3-(6-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)methylamino-2-phenylpiperidine 
• 187679-89-6 (2S,3S)-1-tert-butoxycarbonyl-3-[(7-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)methyl]amino-2-phenylpiperidine 
• 187679-77-2 (2S,3S)-1-tert-butoxycarbonyl-3-[[6-methoxy-1-(2,2,2-trifluoroethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl]methyl]amino-2-phenylpiperidine 
• 187679-71-6 (2S,3S)-1-tert-butoxycarbonyl-3-(1-isopropyl-6-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methylamino-2-phenylpiperidine 
• 187679-74-9 (2S,3S)-1-tert-butoxycarbonyl-3-[(6-difluoromethoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]amino-2-phenylpiperidine 
• 187679-80-7 (2S,3S)-1-tert-butoxycarbonyl-3-[[1-methyl-6-(2,2,2-trifluoroethoxy)-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl]methyl]amino-2-phenylpiperidine 
• 187679-83-0 (2S,3S)-1-tert-butoxycarbonyl-3-[(6-methoxy-1-methyl-2-thioxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]amino-2-phenylpiperidine 
• 187679-86-3 (2S,3S)-1-tert-butoxycarbonyl-3-[(7-methoxy-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzazepin-8-yl)methyl]amino-2-phenylpiperidine 
• 187679-93-2 (2S,3S)-1-tert-butoxycarbonyl-3-[(7-methoxy-1-methyl-2-oxo-4-trifluoromethyl-1,2,3,4-tetrahydroquinolin-6-yl)methyl]amino-2-phenylpiperidine 
• 187679-95-4 (2S,3S)-1-tert-butoxycarbonyl-3-[(6-methoxy-1-methyl-2-oxo-4H-3,1-benzoxazin-7-yl)methyl]amino-2-phenylpiperidine 
• 187679-98-7 (2S,3S)-1-tert-butoxycarbonyl-3-[(6-methoxy-1-methyl-2-oxo-4H-3,1-benzothiazin-7-yl)methyl]amino-2-phenylpiperidine 

Relevant academic research and scientific papers

Synthesis of 2-Arylpiperidines via pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids

The first Pd-catalyzed arylation of aza-Achmatowicz rearrangement products with arylboronic acids is achieved, providing versatile 2-Aryldihydropyridinones for facile synthesis of highly functionalized 2-Arylpiperidines. Key to this arylation is the use of non-phosphine-ligand palladium precatalyst. The substrate scope is demonstrated with >26 examples, and the utility of 2-Aryldihydropyridinones is illustrated by the synthesis of a small collection of 2-Arylpiperidines with substituents or functional groups at any carbon (C2-C6) as well as two NK1 receptor antagonists (+)-CP-999,94 and (+)-L-733,060.

Preparation method of chiral ortho-amino alcohol intermediates, antagonists and analogues of antagonists

The invention belongs to the field of chemical synthesis, relates to a preparation method of chiral ortho-amino alcohols and antagonists, and particularly relates to a preparation method of chiral ortho-amino alcohols and antagonists CP-122, 721 and L-733

Divergent syntheses of L-733, 060 and CP-122721 from functionalized pieridinones made by one-pot tandem cyclization

An efficient diastereoselective approach to access trans-5-hydroxy-6-substituted 2-piperidinones skeleton has been developed through one-pot intramolecular tandem process of O-benzyl protected aldimine 11 with Grignard reagents. The diastereoselectivity of substitution at C-6 position of 2-piperidinone was controlled by α-benzyloxy group. In addition, the utility of this straightforward cascade process is demonstrated by the asymmetric syntheses of (+)-L-733, 060 (2) and its 2-substituted analogue 3, as well as (+)-CP-122721 (5).

Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction

The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.

Concise asymmetric synthesis of (+)-CP-99,994 and (+)-l-733,060 via efficient construction of homochiral syn-1,2-diamines and syn-1,2-amino alcohols

(Chemical Equation Presented) An efficient asymmetric synthesis of human NK-1 SP receptor antagonists (+)-CP-99,994 and (+)-L-733,060 was achieved starting from a common chiral intermediate (5). Our route featured the SmI 2-induced reductive co

RADIOLABELED NEUROKININ-1 RECEPTOR ANTAGONISTS

The present invention is directed to radiolabeled neurokinin-1 receptor antagonists which are useful for the labeling and diagnostic imaging of neurokinin-1 receptors in mammals.

Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands

(E)-Arylaldehyde oxime ethers bearing a (1S)-2-hydroxy-1-phenylethyl or (2R)-1-hydroxy-2-phenylethyl group as a chiral auxiliary, both derived from a single precursor, methyl (R)-mandelate, underwent nucleophilic addition with organolithium reagents via six-membered chelates to give the diastereomerically enriched (R)- and (S)-adducts, respectively, which, after chiral auxiliary removal by reductive N-O bond cleavage, led to the corresponding (R)- and (S)-1-(aryl)ethylamines. This organolithium addition protocol using methyllithium was applied in an enantiodivergent fashion to the preparation of both enantiomers of 1-(2-hydroxyphenyl)ethylamine, which has been previously used as an efficient chiral auxiliary for the synthesis of natural products in this laboratory. The synthetic utility of this methodology involving diastereoselective methyl addition was demonstrated by further application to the asymmetric synthesis of a new type of calcium receptor agonist (calcimimetics), (R)-(+)-NPS R-568 and its thio analogue. Furthermore, diastereoselective vinylation was accomplished by application of the hydroxy oxime ether-based protocol using vinyllithium, which allowed the development of the enantioselective synthesis of the NK-1 receptor antagonists, (+)-CP-99,994 and (+)-CP-122,721.

SUBSTITUTED BENZOLACTAM COMPOUNDS

This invention relates to compounds of general formula (I): or a pharmaceutically acceptable salt thereof, W, T, Y, X, Q, R, R, and R are defined herein. This invention also relates to compounds of formula (I), depicted above, wherein Y is -NH-; T is (2S,3S)-2-phenylpiperidin-3-yl, where the phenyl group of said (2S, 3S)-2-phenylpiperidine-3-yl may optionally be substituted with fluoro; Q is oxygen and is double bonded to the carbon atom to which it is attached, X is methoxy or ethoxy, R is hydrogen, methyl or halo-C1-C2 alkyl, W is methylene, ethylene or vinylene; R and R are independently hydrogen or methyl, or one of R or R may be hydroxy, when W is ethylene, R and R are both methyl, when W is methylene, and R and R are both hydrogen, when W is vinylene. The invention is further directed to methods of treating various CNS and other disorders using said compounds and pharmaceutical compositions thereof.

Substituted benzolactam compounds

This invention relates to compounds of the general formula (1): or a pharmaceutically acceptable salt thereof, W, T, Y, X, Q, R1, R2, and R3 are defined herein. This invention also relates to compounds of the formula I, depicted above, wherein Y is —NH—; T is (2S,3S)-2-phenylpiperidin-3-yl, where the phenyl group of said (2S, 3S)-2-phenylpiperidine-3-yl may optionally be substituted with fluoro; Q is oxygen and is double bonded to the carbon atom to which it is attached, X is methoxy or ethoxy, R1 is hydrogen, methyl or halo-C1-C2 alkyl, W is methylene, ethylene or vinylene; R2 and R3 are independently hydrogen or methyl, or one of R2 or R3 may be hydroxy, when W is ethylene, R2 and R3 are both methyl, when W is methylene, and R2 and R3 are both hydrogen, when W is vinylene. The invention is further directed to methods of treating various CNS and other disorders using said compounds and pharmaceutical compositions thereof.

Asymmetric synthesis of (+)-L-733, 060 and (+)-CP-99, 994 based on a new chiral 3-piperidinol synthon.

[reaction: see text] Selective and potent neurokinin substance P receptor antagonists (+)-L-733, 060 (1) and (+)-CP-99, 994 (2) have been synthesized starting from a new (3S)-piperidinol synthon derived from l-glutamic acid. The methods featured a C-2 reg