944467-32-7

Upstream product

• 518285-15-9 1-tert-butoxycarbonylamino-2-(3-hydroxypropyl)benzene 
• 615-43-0 2-iodophenylamine 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 194979-77-6 tert-butyl 2-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate 
• 287477-27-4 2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]aniline 
• 944467-31-6 1-tert-butoxycarbonylamino-2-[3-(tetrahydropyran-2-yloxy)propyl]benzene 
• 944467-30-5 2-[3-(tetrahydropyran-2-yloxy)propyl]phenylamine 

Relevant academic research and scientific papers

Sc(OTf)3-catalyzed intramolecular diastereoselective cyclization from tert-butoxycarbonyl to acyliminium ion

An effective approach to access dyadic 1,3-oxazinan-2-ones 8a-8c and 4,4a,5,6-tetrahydro-[1,3]oxazino[3,4-a]quinolin-1(3H)-ones 8d-8h was developed through Sc(OTf)3-catalyzed intramolecular cyclization from tert-butoxycarbonyl to acyliminium io

O-Cyclopropyl hydroxylamines: gram-scale synthesis and utility as precursors for N-heterocycles

O-Cyclopropyl hydroxylamines, now accessibleviaa novel and scalable synthetic route, have been demonstrated to be bench-stable and practical precursors for the synthesis of N-heterocyclesviaa di-heteroatom [3,3]-sigmatropic rearrangement. In order to study the reactivity of these compounds in depth, a robust synthesis of both ring-substituted and ring-unsubstitutedO-cyclopropyl hydroxylamines has been developed. Metal-free conditions for the facileN-arylation of these precursors were also identified. It was found that theN-arylatedO-cyclopropyl hydroxamates can efficiently undergo a one-pot [3,3]-sigmatropic rearrangement/cyclization/rearomatization cascade under base-mediated conditions to furnish a structurally diverse set of substituted tetrahydroquinolines.

Palladium-Catalyzed Asymmetric Heck-Matsuda Reaction of 1,4-Dihydroquinolines with Aryl Diazonium Salts

A palladium-catalyzed asymmetric Heck-Matsuda reaction of N -Boc-1,4-dihydroquinolines and aryl diazonium tetrafluoroborates is realized in moderate to high yields and with high enantioselectivities. The method provides an efficient route to access optically active 2-arylhydroquinolines.

Identification of bicyclic hexafluoroisopropyl alcohol sulfonamides as retinoic acid receptor-related orphan receptor gamma (RORγ/RORc) inverse agonists. Employing structure-based drug design to improve pregnane X receptor (PXR) selectivity

We disclose the optimization of a high throughput screening hit to yield benzothiazine and tetrahydroquinoline sulfonamides as potent RORγt inverse agonists. However, a majority of these compounds showed potent activity against pregnane X receptor (PXR) and modest activity against liver X receptor α (LXRα). Structure-based drug design (SBDD) led to the identification of benzothiazine and tetrahydroquinoline sulfonamide analogs which completely dialed out LXRα activity and were less potent at PXR. Pharmacodynamic (PD) data for compound 35 in an IL-23 induced IL-17 mouse model is discussed along with the implications of a high Ymax in the PXR assay for long term preclinical pharmacokinetic (PK) studies.

RORγ MODULATORS

Described are RORγ modulators of the formula (I), or pharmaceutically acceptable salts thereof, wherein all substituents are defined herein. The invention includes stereoisomeric forms of the compounds of formula I, including stereoisomerically-pure, scalemic and racemic form, as well as tautomers thereof. Also provided are pharmaceutical compositions comprising the same. Such compounds and compositions are useful in methods for modulating RORγ activity in a cell and methods for treating a subject suffering from a disease or disorder in which the subject would therapeutically benefit from modulation of RORγ activity, for example, autoimmune and/or inflammatory disorders.

RORγ MODULATORS

Described are RORγ modulators of the formula (I), or pharmaceutically acceptable salts thereof, wherein all substituents are defined herein. The invention includes stereoisomeric forms of the compounds of formula I, including stereoisomerically-pure, scalemic and racemic form, as well as tautomers thereof. Also provided are pharmaceutical compositions comprising the same. Such compounds and compositions are useful in methods for modulating RORγ activity in a cell and methods for treating a subject suffering from a disease or disorder in which the subject would therapeutically benefit from modulation of RORγ activity, for example, autoimmune and/or inflammatory disorders.

Tetrahydroquinoline sulfonamides as vasopressin 1b receptor anatgonists

Vasopressin 1b (V1b) antagonists have been postulated as possible treatments for depression and anxiety. A novel series of potent and selective V1b antagonists has been identified starting from an in-house screen hit. The incorporation of a sulfonamide li

Synthesis of 2,6-dimethyl-9-aryl-9-phosphabicyclo[3.3.1]nonanes: their application to asymmetric synthesis of chiral tetrahydroquinolines and relatives

Synthesis of 2,6-dimethyl-9-aryl-9-phosphabicyclo[3.3.1]nonanes from 1,5-cyclooctadiene and their application to asymmetric cyclization leading to chiral tetrahydroquinolines and relatives through palladium-catalyzed allylic alkylation are described.