4045-30-1

Usage

Uses

Used in Pharmaceutical Industry:
4,4-Dimethylpiperidine is used as a key reactant for the preparation of oral quinoline-based ALDH1A1 inhibitors. ALDH1A1 is an enzyme that plays a crucial role in the development and progression of certain types of cancer. By inhibiting this enzyme, the quinoline-based inhibitors can potentially act as antitumor agents, offering a new avenue for cancer treatment and management.

InChI:InChI=1/C7H15N/c1-7(2)3-5-8-6-4-7/h8H,3-6H2,1-2H3

Upstream product

• 1123-40-6 3,3-dimethyl glutarimide 
• 106754-11-4 1-benzyl-4,4-dimethylpiperidine-2,6-dione 
• 17804-59-0 diethyl 3,3-dimethylglutarate 
• 1194-33-8 2,2-dimethylglutarimide 
• 62496-53-1 1,5-dichloro-3,3-dimethyl-pentane 
• 64-17-5 ethanol 

Downstream Products

• 858850-55-2 1-benzoyl-4,4-dimethyl-piperidine 
• 137795-33-6 (R)-4-(3-Chloro-benzoylamino)-5-(4,4-dimethyl-piperidin-1-yl)-5-oxo-pentanoic acid 
• 1200131-02-7 1-(4-bromobenzyl)-4,4-dimethylpiperidine 
• 1451007-40-1 methyl 2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]-triazolo[1,5-a]pyrimidin-6-yl)acetate 
• 1451007-41-2 methyl 2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]-triazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate 
• 1451007-42-3 methyl 2-tert-butoxy-2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate 
• 1451006-64-6 2-tert-butoxy-2-(7-(4,4-dimethylpiperidin-1-yl)-5-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetic acid 
• 1200127-40-7 3-(4-((4,4-dimethylpiperidin-1-yl)methyl)phenyl)-9H-pyrrolo[2,3-b:5,4-c′]dipyridine-6-carbonitrile 
• 1200131-03-8 4,4-dimethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]piperidine 
• 82679-31-0 1-acetyl-4,4-dimethylpiperidine 
• 137795-79-0 (R)-4-Benzyloxycarbonylamino-5-(4,4-dimethyl-piperidin-1-yl)-5-oxo-pentanoic acid benzyl ester 

Relevant academic research and scientific papers

C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles

Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming α-hydroxy-β-lactams from precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp2)-C(sp3) bond in α-hydroxy-β-lactams using a Rh-complex leads to α-acyl intermediates which undergo sequential Rh-catalyzed decarbonylation, 1,4-addition to an electrophile, and aldol cyclization, to afford N-fused bicycles including indolizidines. Computational studies provide mechanistic insight into the observed positional selectivity of C-C cleavage, which depends strongly on the groups bound to Rh trans to the phosphine ligand.

Discovery of spiro-piperidine inhibitors and their modulation of the dynamics of the M2 proton channel from influenza A virus

Amantadine has been used for decades as an inhibitor of the influenza A virus M2 protein (AM2) in the prophylaxis and treatment of influenza A infections, but its clinical use has been limited by its central nervous system (CNS) side effects as well as emerging drug-resistant strains of the virus. With the goal of searching for new classes of M2 inhibitors, a structure-activity relation study based on 2-[3-azaspiro(5,5)undecanol]-2-midazoline (BL-1743) was initiated. The first generation BL-1743 series of compounds has been synthesized and tested by two-electrode voltage-clamp (TEV) assays. The most active compound from this library, 3-azaspiro[5,5]undecane hydrochloride (9), showed an IC50 as low as0.92 ± 0.11 μM against AM2, more than an order of magnitude m ore potent than amantadine (IC50 = 16 μM). 15N and 13C solid-state NMR was employed to determine the effect of compound 9 on the structure and dynamics of the transmembrane domain of AM2 (AM2-TM) in phospholipid bilayers. Compared to amantadine, spiro-piperidine 9 (1) induces a more homogeneous conformation of the peptide,(2) reduces the dynamic disorder of the G34-I35 backbone near the water -filled central cavity of the helical bundle, and (3) influences the dynamics and magnetic environment of more residues within the transmembranehelices. These data suggest that spiro-piperidine 9 binds more extensiv ely with the AM2 channel, thus leading to stronger inhibitory potency.

PHARMACEUTICAL COMPOUNDS

The invention provides a compound of the formula (I) or a salt, solvate, tautomer or N-oxide thereof; wherein A is a saturated hydrocarbon linker group; E is a monocyclic or bicyclic carbocyclic or heterocyclic group; L1 is a bond or a linker selected from C1-C4 alkenylene, C1-C4 alkynylene, -CONR’, -NR’CO, -S, -C(O)-, -C(NR11)-, -C(S)-, -N(R11)2, C(=CHR11), -SO- and -SO2-; or L1 together with t R16 forms and 8-12 membered fused bicyclic heteroaryl ring system; L3 is a bond or a linker selected from CONH and HNCO; provided that L1 and L3 cannot both be linkers simultaneously; and provided also that L1 and L3 cannot both be a bond simultaneously; R16 is an optionally substituted 5- to 12-membered monocyclic or bicyclic carbocyclic or heterocyclic ring; L2 is absent or is a linker selected from C]-C4 alkylene, Ci-C4 alkenylene, Ci-C4 alkynylene, -CONR’-, -NR’CO-, -O-, -S-, -C(O)-, C(=CHR11), C(S)-, -N(R11)2, C3-4 cycloalkanediyl, -SO- and -SO2-; R17 is absent or is C1-6 alkyl or an optionally substituted 5 to 12 membered carbocyclic or heterocyclic ring; provided that when R17 is absent, then L2 is also absent; and R2, R3, R4, R5, R11 and R’ are as defined in the claims.

N-sulfonylurea apoptosis promoters

Compounds having the formula are apoptosis promoters. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

Rate Increase in Consecutive Nucleophilic Aromatic Substitution Reactions of Trichlorotrinitrobenzene: The Synthesis of 1-(Alkylamino)-3,5-dichloro-2,4,6-trinitrobenzenes

The title compounds are formed by the nucleophilic aromatic substitution reaction between symtrichlorotrinitrobenzene and amines. The yields and relative rates of formation depend critically on the degree of alkylation of the nucleophile. Contrary to the usual behavior, the introduction of a second and third donor is facilitated in the case of ammonia and monoalkylamines, while this is not the case for secondary amines. This behavior is rationalized on the basis of intramolecular hydrogen bonding and substantiated by an X-ray analysis of 3,5-dichloro-2,4,6-trinitroaniline.

BENZOTHIAZEPINE AND BENZOXAZEPINE DERIVATIVES AS CHOLECYSTOKININ RECEPTOR ANTAGONISTS

The present invention relates to novel substituted benzothiazepines and benzoxazepines of the formula STR1 wherein R 1, R 2, R. sup. 7, R 8, R 9 and X are as defined below, and to novel intermediates used in the synthesis of such compounds. Such compounds are useful in the treatment and prevention of gastrointestinal disorders, pain and anxiety disorders.

Benzodiazepine derivatives

Compounds of Formula (I), and salts and prodrugs thereof, wherein R1 represents H, optionally substituted C1-6 alkyl or C3-7 cycloalkyl; R2 is NHR12 or (CH2)s R13 where 5 is 0, 1 or 2; R3 represents C1-6 alkyl, halo or NR6 R7 ; R4 and R5 are H, C1-12 alkyl optionally substituted by NR9 R9' or an azacyclic or azabicyclic group, optionally substituted C4-9 cycloalkyl, C4-9 cycloalkyl C1-4 alkyl, aryl, arylC1-6 alkyl or azacyclic or azabicyclic groups, or R4 and R5 together form the residue of an optionally substituted azacyclic or azabicyclic ring system; x is 0, 1, 2 or 3; R12 is optionally substituted phenyl or pyridyl; R13 represents a group (A) wherein R14 is H or C1-6 alkyl; R15 is H, C1-6 alkyl, halo or NR6 R7 ; and the dotted line is an optional covalent bond; are CCK and/or gastrin antagonists useful in therapy. STR1

Asymmetric synthesis catalyzed by chiral ferrocenylphosphine transition metal complexes. 10 gold(I)-catalyzed asymmetric aldol reaction of isocyanoacetate

Optically active ferrocenylbisphosphine ligands containing 2-(dialkylamino)ethylamino group on the ferrocenylmethyl position have been prepared and used for the gold(I)-catalyzed asymmetric aldol reaction of isocyanoacetate with aldehydes. Six-membered ring amines, such as morpholino or piperidino group, at the terminal of the side chain were most stereoselective to give optically active trans-4- methoxycarbonyl-5-alkyl-2-oxazolines (up to 97% ee) with high enantio- and diastereoselectivity in a quantitative yield.