209808-06-0

Usage

Uses

Used in Pharmaceutical Industry:
1-BOC-4-(4-CHLORO-BENZOYL)-PIPERIDINE is used as a reactant for the structural optimization of 4-chlorobenzoylpiperidine derivatives. These derivatives are being developed as potent, reversible, and selective monoacylglycerol lipase (MAGL) inhibitors. MAGL is an enzyme that plays a crucial role in the degradation of endocannabinoids, which are involved in various physiological processes, including pain, inflammation, and mood regulation. By inhibiting MAGL, these derivatives have the potential to modulate the endocannabinoid system and may be useful in the treatment of various conditions such as chronic pain, neuroinflammation, and mood disorders.

InChI:InChI=1/C17H22ClNO3/c1-17(2,3)22-16(21)19-10-8-13(9-11-19)15(20)12-4-6-14(18)7-5-12/h4-7,13H,8-11H2,1-3H3

Upstream product

• 160296-40-2 tert-butyl 1-[4-(4-fluorobenzoyl)piperidin-1-yl]carboxylate 
• 637-87-6 1-Chloro-4-iodobenzene 
• 139290-70-3 tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate 
• 104-88-1 4-chlorobenzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 639468-65-8 4-[(4-chlorophenyl)hydroxymethyl]piperidine-1-carboxylic acid tert-butyl ester 
• 25503-90-6 1-acetyl-piperidine-4-carboxylic acid 
• 59084-16-1 1-acetylpiperidine-4-carbonyl chloride 
• 59084-15-0 N-acetyl-4-(p-chlorobenzoyl)piperidine 
• 53220-41-0 4-(4-chlorobenzoyl)piperidine 
• 55695-51-7 4-(4-chlorobenzoyl)piperidine hydrochloride 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 99121-25-2 2-(4-Chlorphenyl)-2-deuterio-1,3-dithian 
• 10359-09-8 2-(4-chlorophenyl)-1,3-dithiane 

Downstream Products

• 209808-08-2 4-(α-hydroxy-α-(4-N-tert-butoxycarbonylpiperidinyl)-4-chlororobenzyl)-N,N-diethylbenzamide 
• 639468-65-8 4-[(4-chlorophenyl)hydroxymethyl]piperidine-1-carboxylic acid tert-butyl ester 
• 645379-32-4 1,1-dimethylethyl-4-[(4-chlorophenyl)carbonyl]-4-fluoro-1-piperidinecarboxylate 
• 885595-32-4 4-[amino(4-chlorophenyl)methyl]piperidine-1-carboxylic acid tert-butyl ester 
• 897630-52-3 C₁₇H₂₃ClN₂O₃ 
• 55695-51-7 4-(4-chlorobenzoyl)piperidine hydrochloride 
• 885595-34-6 C-(4-chlorophenyl)-C-piperidin-4-ylmethylamine hydrochloride 
• 42060-83-3 [1,1'-biphenyl]-4-yl(piperidin-4-yl)methanone 
• 918501-81-2 tert-butyl 4-((4-chlorophenyl)(methoxy)methyl)piperidine-1-carboxylate 
• 918501-97-0 C₁₉H₂₈ClNO₃ 
• 918502-07-5 C₁₉H₂₄ClN₃O₄ 
• 209807-41-0 N,N-Diethyl-4-(4-chlorophenyl-piperidin-4-ylidene-methyl)-benzamide 

Relevant academic research and scientific papers

MITOCHONDRIAL INHIBITORS FOR THE TREATMENT OF PROLIFERATION DISORDERS

The invention provides compounds of formula (I) or pharmaceutically acceptable salt thereof wherein ring A represents group A-I, A-II or A-III. Al represents -C(R4a)(R4a)-, -C(R4a)= -N(R4b)-, -N= -O- or -S-; A2 represents -C(R4c)(R4c)-, -C(R4c)= or -0-; A3 represents -C(R4c)(R4c)-, -C(R4c)= or -0-; A4 represents -C(R4a)(R4a)-, -C(R4a)= -N= -O- or -S-; A5 represents -C(R4a)(R4a)-, -C(R4a)= -N(R4b)-, -N= -O- or -S-; A6 represents -C(R4c)(R4c)- or -C(R4c)=; A7 represents -C(R4a)(R4a)-, -C(R4a)= -N= -O- or -S-; A8 represents -C(R4a)(R4a)-, -N(R4b)-, -O- or -S-; A9 represents -C(R4c)(R4c)- or -0-; A10 represents -C(R4c)(R4c)- or -0-; A11 represents -C(R4c)(R4c)- or -0-; A12 represents -C(R4a)(R4a)-, -O- or -S-; wherein group A-I, group A-II and group A-III de not contain adjacent oxygen atoms, adjacent oxygen and sulfur atoms or adjacent oxygen and nitrogen atoms or a moiety selected from the group consisting of N-C-N, N-C-S, S-C-S, O-C-N, O-C-O and O-C-S, wherein in each case the carbon atom in the N-C-N, N-C-S, S-C-S, O-C-N, O-C-O and O-C-S moiety is saturated; B1, B2, B3 and B4 represent independently C(R3) or N, wherein no more than two of B1, B2, B3 and B4 represent N; n is 1 or 2; and R1, R2, R3, R4a, R4b and R4c are as defined in the claims, as well as methods of using the compounds to treat proliferation diseases, in particular cancer.

C-H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

The difficulty in accessing and safely utilising non-stabilised diazo species has in the past limited the application of this class of compounds. Here we explore further the use of oxadiazolines, non-stabilised diazo precursors which are bench stable, in direct, non-catalytic, aldehyde C-H functionalisation reactions under UV photolysis in flow and free from additives. Commercially available aldehydes are coupled to afford unsymmetrical aryl-alkyl and alkyl-alkyl ketones while mild conditions and lack of transition metal catalysts allow for exceptional functional group tolerance. Examples are given on small scale and in a larger scale continuous production.

Structural Optimization of 4-Chlorobenzoylpiperidine Derivatives for the Development of Potent, Reversible, and Selective Monoacylglycerol Lipase (MAGL) Inhibitors

Monoacylglycerol lipase (MAGL) inhibitors are considered potential therapeutic agents for a variety of pathological conditions, including several types of cancer. Many MAGL inhibitors are reported in literature; however, most of them showed an irreversible mechanism of action, which caused important side effects. The use of reversible MAGL inhibitors has been only partially investigated so far, mainly because of the lack of compounds with good MAGL reversible inhibition properties. In this study, starting from the (4-(4-chlorobenzoyl)piperidin-1-yl)(4-methoxyphenyl)methanone (CL6a) lead compound that showed a reversible mechanism of MAGL inhibition (Ki = 8.6 μM), we started its structural optimization and we developed a new potent and selective MAGL inhibitor (17b, Ki = 0.65 μM). Furthermore, modeling studies suggested that the binding interactions of this compound replace a structural water molecule reproducing its H-bonds in the MAGL binding site, thus identifying a new key anchoring point for the development of new MAGL inhibitors.

SULFONYL PIPERIDINE DERIVATIVES AND THEIR USE FOR TREATING PROKINETICIN MEDIATED GASTROINTESTINAL DISORDERS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof (Formula (I)) in which m, n, W, X, Y, Z, R1, R22, R3, R4 and R5 are as defined in the specificatio

Preparation of unsymmetrical ketones from tosylhydrazones and aromatic aldehydes via formyl C-H bond insertion

Preparation of ketones by insertion of diazo compounds into the formyl C-H bond of an aldehyde is an attractive procedure, but use of structurally diverse diazo compounds is hampered by preparation and safety issues. A convenient procedure for the synthesis of unsymmetrical ketones from bench-stable tosylhydrazones and aryl aldehydes is reported. The procedure can be performed in one pot from the parent carbonyl compound and needs only a base, with no additional promoters being required.

1-SULFONYL PIPERIDINE DERIVATIVES AS MODULATORS OF PROKINETICIN RECEPTORS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof in which m, n, W, X, Y, Z, R1 , R2, R3, R4 and R5 are as defined in the specification, composition

THERAPEUTIC COMPOUNDS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof in which m, n, W, X, Y, Z, R, R1, R2, R3 and R4 are as defined in the specification, for use in therapy.

SULFONYL PIPERIDINE DERIVATIVES AND THEIR USE FOR TREATING PROKINETICIN MEDIATED DISEASES

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof : (I) in which m, n, W, X, Y, Z, R1, R2, R3 and R4 are as defined in the specification, for use in the treatm

Identification of 4-(4-aminopiperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidines as selective inhibitors of protein kinase B through fragment elaboration

Fragment-based screening identified 7-azaindole as a protein kinase B inhibitor scaffold. Fragment elaboration using iterative crystallography of inhibitor-PKA-PKB chimera complexes efficiently guided improvements in the potency and selectivity of the compounds, resulting in the identification of nanomolar 6-(piperidin-1-yl)purine, 4-(piperidin-1-yl)-7-azaindole, and 4-(piperidin-1-yl)pyrrolo[2,3-d]pyrimidine inhibitors of PKBβ with antiproliferative activity and showing pathway inhibition in cells. A divergence in the binding mode was seen between 4-aminomethylpiperidine and 4-aminopiperidine containing molecules. Selectivity for PKB vs PKA was observed with 4-aminopiperidine derivatives, and the most PKB-selective inhibitor (30-fold) showed significantly different bound conformations between PKA and PKA-PKB chimera.

PHARMACEUTICAL COMPOUNDS

The invention provides a compound having the formula (I): or salts, solvates, tautomers or N-oxides thereof, wherein T is N or CR5; J1-J2 is N=C(R6), (R7)C=N, (R8)N-C(O), (R8)2C-C(O), N=N or (R7)C=C(R6); A is an optionally substituted saturated C1-7 hydrocarbon linker group having a maximum chain length of 5 atoms extending between R1 and NR2R3 and a maximum chain length of 4 atoms extending between E and NR2R3, one of the carbon atoms in the linker group being optionally replaced by oxygen or nitrogen; E is a monocyclic or bicyclic carbocyclic or heterocyclic group or an acyclic group X-G wherein X is CH2, O, S or NH and G is a C1-4 alkylene chain wherein one of the carbon atoms is optionally replaced by O, S or NH; R1 is hydrogen or an aryl or heteroaryl group; R2 and R3 are each hydrogen, optionally substituted C1-4 hydrocarbyl or optionally substituted C1-4 acyl; or NR2R3 forms an imidazole group or a saturated monocyclic heterocyclic group having 4-7 ring members; or NR2R3 and A together form a saturated monocyclic heterocyclic group having 4-7 ring members which is optionally substituted by C1-4 alkyl; or NR2R3 and the adjacent carbon atom of linker group A together form a cyano group; or R1, A and NR2R3 together form a cyano group; and R4, R5, R6, R7 and R8 are each independently selected from hydrogen and various substituents as defined in the claims, wherein the compound is for use in: (a) the treatment or prophylaxis of a disease or condition in which the modulation (e.g. inhibition) of ROCK kinase or protein kinase p70S6K is indicated; and/or (b) the treatment of a subject or patient population in which the modulation (e.g. inhibition) of ROCK kinase or protein kinase p70S6K is indicated.