7006-50-0

Usage

Uses

Used in Pharmaceutical Industry:
(1-Benzyl-piperidin-4-yl)-methyl-amine is used as a key intermediate in the synthesis of Taladegib, a small molecule inhibitor of the hedgehog signaling pathway. This application is significant for the development of targeted therapies against various cancers, such as basal cell carcinoma, medulloblastoma, and other malignancies driven by the aberrant activation of the hedgehog signaling pathway. By inhibiting this pathway, Taladegib can help control tumor growth and potentially lead to improved treatment outcomes for patients with these types of cancer.

InChI:InChI=1/C13H20N2/c1-14-13-7-9-15(10-8-13)11-12-5-3-2-4-6-12/h2-6,13-14H,7-11H2,1H3

Upstream product

• 64951-37-7 ethyl (1-phenylmethyl-4-piperidyl)carbamate 
• 7144-05-0 4-Aminomethylpiperidine 
• 100-44-7 benzyl chloride 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 593-51-1 methylamine hydrochloride 
• 144-55-8 sodium hydrogencarbonate 
• 7732-18-5 water 
• 100-39-0 benzyl bromide 
• 73874-95-0 tert-butyl N-(piperidin-4-yl)carbamate hydrochloride 
• 620-08-6 4-methoxypyridine 
• 100-59-4 phenylmagnesium chloride 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 478832-19-8 N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoro-N-methylacetamide 
• 50541-93-0 4-amino-1-benzylpiperidine 

Downstream Products

• 76167-79-8 (1-Benzyl-piperidin-4-yl)-methyl-pyrimidin-2-yl-amine 
• 179557-27-8 1-benzyl-4-[N-methyl-N-(3-nitro-2-pyridinyl)amino]piperidine 
• 34737-89-8 1-Benzyl-3-methyl-4-piperidon 
• 179556-50-4 1-benzyl-4-(N-methyl-N-(3-methoxycarbonyl-2-pyridinyl)amino)piperidine 
• 179557-72-3 1-Benzyl-4-[N-methyl-N-(2-nitro-4-fluorophenyl)amino]piperidine 
• 147908-83-6 1-benzyl-4-(N-methyl-N-acetylamino)piperidine 
• 139679-51-9 N-Butyl-N'-[1-(phenylmethyl)-4-piperidinyl]urea 
• 111448-61-4 1-Benzyl-4-N-[4,4-bis(4-fluorophenyl)butyl]-N-methylaminopiperidine 
• 71879-36-2 N-(1-Benzyl-piperid-4-yl)-N-methyltrifluoracetamide hydrochloride 
• 1259510-81-0 C₂₆H₃₁N₅O₂S 
• 1269795-79-0 N-((1-benzylpiperidin-4-yl))-6-chloro-N-methylbenzo[d]thiazol-2-amine 
• 1580436-33-4 (1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-Nmethylaminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene] 
• 1258861-20-9 4-fluoro-N-methyl-N-{1-[4-(1-methyl-1H-pyrazole-5-yl)phthalazin-1-yl]piperidin-4-yl}-2-(trifluoromethyl)benzamide 

Relevant academic research and scientific papers

Nitrogen heterocyclic compound, pharmaceutical composition containing nitrogen heterocyclic compound, and preparation method and application of nitrogen heterocyclic compound

Disclosed are a nitrogen heterocyclic compound represented by a formula (I), a pharmaceutical composition comprising the same, and a preparation method and use of the nitrogen heterocyclic compound, and in particular, relates to the use of the nitrogen heterocyclic compound for prevention or treatment of diseases or conditions associated with RET activity.

Design, synthesis and evaluation of (R)-3-(7-(methyl?7H-pyrrolo?2, 3-d]pyrimidin-4-yl)amino)-5-azaspiro?2.4]heptan-5-yl)-3-oxopropanenitrile as a JAK1-selective inhibitor

Based on (R)-N-methyl-N-(5-azaspiro?2.4]heptan-7-yl)-7H-pyrrolo?2, 3-d]pyrimidin-4-amine as a core scaffold, we identified (R)-3-(7-(methyl?7H-pyrrolo?2, 3-d]pyrimidin-4-yl)amino)-5-azaspiro?2.4]heptan-5- yl)-3-oxopropanenitrile [(R)-6c] as a JAK1 selective inhibitor. The structural design was based on the combination of tofacitinib's 7-deazapurine and 5-azaspiro?2.4]heptan-7-amine. Compound (R)-6c exhibited an IC50 value of 8.5 nM against JAK1 with a selectivity index of 48 over JAK2. To optimize (R)-6c as a lead compound, we performed in vitro ADME, hERG, kinase profiling, and pharmacokinetic tests. Mouse and rat in vivo studies verified that (R)-6c exhibited desired efficacies in CIA and AIA models.

JANUS KINASE 1 SELECTIVE INHIBITOR AND PHARMACEUTICAL USE THEREOF

Janus kinase 1 selective inhibitors and pharmaceutical use thereof are provided.

Benzamide Hedgehog inhibitor as well as preparation method and application thereof

The invention discloses a benzamide Hedgehog inhibitor as well as a preparation method and application thereof. The inhibitor has the structure show as a general formula (I) (shown in the specification). Compared with the prior art, a novel benzamide compound provided by the invention is capable of targeting Smoothened proteins in a Hedgehog signal channel, the drug resistance caused by mutation of a Smoothened acceptor can be effectively avoided, so that the Hedgehog signal channel can be effectively inhibited, and Hedgehog signal channel relevant tumors, such as basal cell carcinoma (BCCs), medulloblastoma, breast carcinoma, colon cancer or lung cancer, can be effectively treated.

An efficient palladium-catalyzed synthesis of 1-heteroaryl-4-aminopiperidine derivatives from heteroaryl chlorides

An efficient protocol for the synthesis of 1-heteroaryl-4-(N-methyl)aminopiperidines starting from heteroaryl chloride derivatives is described. A broad range of 1-heteroaryl-4-(N-Boc-N-methyl)aminopiperidine derivatives were obtained in good to excellent

A novel and efficient route for synthesis of Taladegib

Taladegib (LY-2940680), a small molecule Hedgehog signalling pathway inhibitor, was obtained from N-benzyl-4-piperidone via Borch reductive amination, acylation with 4-fluoro-2-(trifluoromethyl)benzoyl chloride, debenzylation, substitution with 1,4-dichlorophthalazine and Suzuki cross-coupling reaction with 1-methyl-1H-pyrazole-5-boronic acid. The advantages of this synthesis route were the elimination of Boc protection and deprotection and the inexpensive starting materials. Furthermore, the debenzylation reaction was achieved with simplified operational procedure using ammonium formate as hydrogen source that provided high reaction yield. This synthetic procedure was suitable for large-scale production of the compound for biological evaluation and further study.

Synthetic method of Taladegib

The invention discloses a synthetic method of Taladegib. The synthetic method is characterized by comprising the following steps that reductive amination is carried out on N-benzyl-4-piperidone to obtain a compound in formula VI; in the presence of an organic base, an acylation reaction is carried out on the compound in the formula VI and an acylation reagent to obtain a compound in the formula VIII; the acylation reagent is 4-fluoro-2-(trifluoromethyl)benzoyl chloride; in the presence of a hydrogen source and a palladium catalyst, debenzylation is carried out on the compound in formula VIII to obtain a compound in the formula IX; in the presence of an inorganic base, the compound in the formula IX is reacted with 1,4-dichloro phthalazine to obtain a compound in the formula X; in the presence of the inorganic base and the palladium catalyst, an SUZUKI coupling reaction is carried out on the compound in the formula X and 1-methyl-1H-pyrazole-5-boronic acid pinacol ester to obtain Taladegib. According to the invention, the process route is improved, cheap N-benzyl-4-piperidone is taken as a starting material, the processes of Boc protection and deprotection are removed to reduce the synthesis steps and reduce the production cost.

QUINAZOLINE COMPOUNDS AND THEIR USE IN THERAPY

This invention relates to quinazoline compounds of Formula (I) which are inhibitors of the histone lysine methyltransferase (HKMTase) EZH2, and to uses of such compounds as medicaments, in particular in the treatment of a disease or disorder in which inhibition of EZH2 provides a therapeutic or prophylactic effect.

Substituted Benzamide Compounds

Substituted benzamide compounds corresponding to formula (I) in which R5, R6, R7, R8, a, b, c, d, t, D and X have defined meanings, a process for their preparation, pharmaceutical compositions comprising such compounds, and a method of using such compounds to treat pain and other conditions mediated at least in part via the bradykinin 1 receptor.

NEW COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS RELATING THERETO

New compounds are disclosed which have utility in the treatment of a variety of metabolic related conditions in a patient. The compounds of this invention have the structure (I): wherein X1, X2, X3, X4, Y1