286961-15-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER is used as a reactant for the synthesis of potent and orally bioavailable inhibitors of βII tryptase. These inhibitors are crucial in the treatment of allergic diseases, as they help regulate the immune response and alleviate symptoms associated with allergies.
Application Reason:
4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID BENZYL ESTER's unique structure allows for the development of inhibitors with high specificity and efficacy against βII tryptase, a key enzyme involved in the pathogenesis of allergic reactions. By targeting this enzyme, the synthesized inhibitors can potentially provide effective relief for patients suffering from various allergic conditions, such as asthma, rhinitis, and atopic dermatitis.

InChI:InChI=1/C19H26BNO4/c1-18(2)19(3,4)25-20(24-18)16-10-12-21(13-11-16)17(22)23-14-15-8-6-5-7-9-15/h5-10H,11-14H2,1-4H3

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 286961-24-8 benzyl 1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylate 
• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 1121057-75-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride 
• 501-53-1 benzyl chloroformate 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 161609-91-2 benzyl 4-phenyl-3,6-dihydropyridine-1(2H)-carboxylate 
• 286961-23-7 benzyl 4-(4-methoxyphenyl)-3,6-dihydropyridine-1(2H)-carboxylate 
• 851961-34-7 C₃₀H₃₈N₂O₆ 
• 630116-80-2 3-cyano-3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid benzyl ester 
• 865111-73-5 1,1-dimethylethyl 7-(1-{[(phenylmethyl)oxy]carbonyl}-1,2,3,6-tetrahydro-4-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate 
• 890531-23-4 4-(10-benzyl-2-methyl-11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepin-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylic benzyl ester 
• 1251537-33-3 (1-((benzyloxy)carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acid 
• 1206967-78-3 tert-butyl 4-[2-(4-ethoxycarbonyl-3-fluorophenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate 
• 1206967-77-2 5-[1-(5-Isopropyl-1,2,4-oxadiazol-3-yl)piperidin-4-yl]-2-(4-methanesulfonylphenoxymethyl)pyridine 
• 1206968-68-4 N-Hydroxy-4-[2-(4-methanesulfonylphenoxymethyl)-pyridin-5-yl]piperidin-1-carboxamidine 
• 1206968-67-3 4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-carbonitrile 

Relevant academic research and scientific papers

Technological method for synthesizing N-substituted-1,2,5,6-tetrahydropyridine-4-boric acid ester

The invention relates to an organic compound synthesis method, in particular to a technological method for synthesizing N-substituted-1,2,5,6-tetrahydropyridine-4-boric acid ester. The method comprises the step that N-substituted-1,2,5,6-tetrahydropyridine-4-halide serves as a raw material to react with bi-boric acid ester, cuprous halide or cuprous oxide, a ligand and organic base in a solvent, so that N-substituted-1,2,5,6-tetrahydropyridine-4-boric acid ester is obtained. The method is innovative, and easy and convenient to operate, the technological route is short, the cost is low, the product purity is high, the reaction conditions are mild, the situation that metal palladium coupling or a high-activity Grignard reagent and a low temperature condition are adopted in a traditional method is avoided, and the method has potential cost advantage, and is suitable for industrialized scale-up production.

Synthesis method of N-substituted-1,2,5,6-tetrahydropyridine-4-borate

The invention discloses a synthesis method of N-substituted-1,2,5,6-tetrahydropyridine-4-borate. According to the synthesis method, N-substituted-4-piperidone is taken as the raw material, N-substituted-4-piperidone, triaryl phosphite, halogen, and organic alkali carry out reactions, the carbonyl group is converted into vinyl halogen, and finally the reaction product reacts with isopropyl magnesium chloride-lithium chloride and alkoxyl borate to generate N-substituted-1,2,5,6-tetrahydropyridine-4-borate. The synthesis method has the advantages that the raw materials are easily available, the operation is simple and convenient, the product purity is high, the ultralow temperature condition and palladium catalytic coupling are not needed, the cost is reduced, the route is optimized, and thus the product is competitive in the market.

INHIBITORS OF FATTY ACID AMIDE HYDROLASE

Provided herein are compounds of formula (I): or pharmaceutically acceptable salts, solvates or prodrugs thereof or mixtures thereof, wherein Z1, Z2, X1, X2, X3, R1, R2 R3/

DIARYL KETIMINE DERIVATIVE HAVING ANTAGONISM AGAINST MELANIN-CONCENTRATING HORMONE RECEPTOR

[Problems] To provide an antagonist of a melanin-concentrating hormone receptor, which is useful as a medicine for a central nervous system disease, a cardiovascular disease or a metabolic disease. [Means for Solving Problems] The antagonist comprises, as an active ingredient, a compound represented by the formula (I) wherein R1a and R1b independently represent a hydrogen atom or a C1-6 alkyl group; R2a, R2b, R3a and R3b independently represent a hydrogen atom, a C1-6 alkyl group, or the like; Y represents H or —OH; Z represents —OR8, or the like; R8 represents a hydrogen atom, a C1-6 alkyl group which may have a substituent, or the like; R9a and R9b independently represent a hydrogen atom, a C1-6 alkyl group, or the like; Ar1 represents an aromatic carbon ring group, or an aromatic heteroring group; Ar2 represents a group produced by removing two hydrogen atoms from an aromatic carbon ring, or the like; and the ring group A represents an unsaturated heteroring group.

SMALL MOLECULE INHIBITORS OF PROTEIN ARGININE METHYLTRANSFERASES (PRMTS)

The present invention relates to compounds that are useful as inhibitors of protein arginine methyltransferase that have a formula selected from Formula (I), Formula (II) and Formula (III), as well as racemic mixtures, diastereomers, enantiomers and tautomers thereof and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof as defined herein. Said compound are useful as inhibitors of PRMTs and/or CARM-I. The invention further relates to compositions comprising such compounds and methods for their use.

Discovery of 3-methyl-N-(1-oxy-3′,4′,5′,6′- tetrahydro-2′H-[2,4′-bipyridine]-1′-ylmethyl)benzamide (ABT-670), an orally bioavailable dopamine D4 agonist for the treatment of erectile dysfunction

The goal of this study was to identify a structurally distinct D4-selective agonist with superior oral bioavailability to our first-generation clinical candidate 1a (ABT-724) for the potential treatment of erectile dysfunction. Arylpiperazines such as (heteroarylmethyl)piperazine 1a, benzamide 2, and acetamides such as 3a,b exhibit poor oral bioavailability. Structure-activity relationship (SAR) studies with the arylpiperidine template provided potent partial agonists such as 4d and 5k that demonstrated no improvement in oral bioavailability. Further optimization with the (N-oxy-2-pyridinyl)piperidine template led to the discovery of compound 6b (ABT-670), which exhibited excellent oral bioavailability in rat, dog, and monkey (68%, 85%, and 91%, respectively) with comparable efficacy, safety, and tolerability to 1a. The N-oxy-2-pyridinyl moiety not only provided the structural motif required for agonist function but also reduced metabolism rates. The SAR study leading to the discovery of 6b is described herein.

CYCLOALKANOPYRIDINE DERIVATIVE

Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.

Structure based design of 4-(3-aminomethylphenyl)piperidinyl-1-amides: Novel, potent, selective, and orally bioavailable inhibitors of βII tryptase

Tryptase is a serine protease found almost exclusively in mast cells. It has trypsin-like specificity, favoring cleavage of substrates with an arginine (or lysine) at the P1 position, and has optimal catalytic activity at neutral pH. Current evidence suggests tryptase β is the most important form released during mast cell activation in allergic diseases. It is shown to have numerous pro-inflammatory cellular activities in vitro, and in animal models tryptase provokes broncho-constriction and induces a cellular inflammatory infiltrate characteristic of human asthma. Screening of in-house inhibitors of factor Xa (a closely related serine protease) identified β-amidoester benzamidines as potent inhibitors of recombinant human βII tryptase. X-ray structure driven template modification and exchange of the benzamidine to optimize potency and pharmacokinetic properties gave selective, potent and orally bioavailable 4-(3-aminomethyl phenyl)piperidinyl-1-amides.

Acetamides and benzamides that are useful in treating sexual dysfunction

The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.