694495-63-1

Usage

Uses

Used in Pharmaceutical Industry:
3-METHOXYCARBONYLAMINO-4-METHYLPYRIDINE is used as a JAK3 inhibitor for its immunosuppressant properties. It plays a crucial role in modulating the immune response by targeting the Janus kinase 3 (JAK3) enzyme, which is involved in the signaling pathways of various cytokines and growth factors. Inhibition of JAK3 can help in the treatment of autoimmune diseases and transplant rejection by reducing inflammation and immune cell activation.

InChI:InChI=1/C8H10N2O2/c1-6-3-4-9-5-7(6)10-8(11)12-2/h3-5H,1-2H3,(H,10,11)

Upstream product

• 3430-27-1 3-amino-4-methylpyridine 
• 79-22-1 methyl chloroformate 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 1616760-91-8 methyl-(1-trityl-4-methylpiperidin-3-yl)carbamate 
• 1616833-40-9 1-triryI-N,4-dimethylpiperidin-3-amine 
• 1616761-04-6 (3S,4S)-1-trityl-N,4-dimethylpiperidin-3-amine di-p-toluyl-L-tartaric acid salt 
• 1616760-93-0 (3R,4R)-1-trityl-N,4-dimethylpiperidin-3-amine 
• 1616760-94-1 C₃₉H₃₈ClN₅O₂S 
• 1616760-95-2 C₂₀H₂₄ClN₅O₂S 
• 1616760-96-3 C₃₂H₃₂ClN₅ 
• 1616760-97-4 N-((3R,4R)-4-methyl-piperidin-3-yl)-N-methyl-2-chloro-7H-pyrrolo[2,3-D]pyrimidine-4-amine 
• 477600-74-1 tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate 
• 1259404-17-5 tasocitinib 
• 540737-29-9 Tofacitinib citrate 
• 540737-29-9 tofacitinib hemi-citrate 
• 1204176-45-3 methyl-(4-methylpiperidin-3-yI)carbamate 
• 1204176-45-3 cis-methyl (4-methylpyridin-3-yl)carbamate 

Relevant academic research and scientific papers

A synthetic cis - 1 - benzyl - 3 - methylamino - 4 - methyl - piperidine

The invention relates to a method for synthesizing cis-1-benzyl-3-methylamino-4-methyl-piperidine, in particular to a method for synthesizing cis-1-benzyl-3-methylamino-4-methyl-piperidine by taking 1-benzyl-3-methylamino-4-methyl-piperidine bromide as an

An Efficient Method for Synthesis of Tofacitinib Citrate

An efficient and mild synthetic method was developed for tofacitinib citrate from 3-amino-4-methylpyridine and 4-chloro-7H-pyrrolo[2,3-d]pyrimidine. The related reactions were systematically optimized. Sodium hydride instead of potassium tert-butoxide employed in the methoxycarbonylation reaction of compound 9 made the reaction proceed effectively to present compound 8 in a better yield. The replacement of benzaldehyde with benzyl bromide simplified the protection process of amino group. Red-Al provided a cost-effective method for the reduction of amides. The introduction of tosyl group into compound 10 enhanced the nucleophilic substitution of 10 with compound 4 dramatically. Thus, under the optimized conditions, tofacitinib citrate was obtained in 13.3% yield (based on compound 9) with a purity of 99.9%, much better than the reported yield 8.6%. This cost-effective and environmental friendly process is more suitable for scale-up production.

Design and synthesis of tricyclic jak3 inhibitors with picomolar affinities as novel molecular probes

The Janus kinase (JAK) signaling pathway is of particular importance in the pathology of inflammatory diseases and oncological disorders, and the inhibition of Janus kinase 3 (JAK3) with small molecules has proven to provide therapeutic immunosuppression. A novel class of tricyclic JAK inhibitors derived from the 3-methyl-1,6-dihydrodipyrrolo[2,3-b:2',3'-d]pyridine scaffold was designed based on the tofacitinib-JAK3 crystal structure by applying a rigidization approach. A convenient synthetic strategy to access the scaffold via an intramolecular Heck reaction was developed, and a small library of inhibitors was prepared and characterized using in vitro biochemical as well as cellular assays. IC50 values as low as 220 pm could be achieved with selectivity for JAK3 over other JAK family members. Both activity and selectivity were confirmed in a cellular STAT phosphorylation assay, providing also first-time data for tofacitinib. Our novel inhibitors may serve as tool compounds and useful probes to explore the role of JAK3 inhibition in pharmacodynamics studies.

THE PRESENT INVENTION RELATES TO PROCESS FOR THE PREPARATION OF TOFACITINIB AND INTERMEDIATES THEREOF.

The present invention relates to process for the preparation of tofacitinib and intermediates thereof.

HETEROCYCLIC COMPOUNDS AS JANUS KINASE INHIBITORS

The invention provides compounds of formula (I) or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula I and therapeutic methods for suppressing an immune response or treating cancer or a hematologic malignancy using compounds of formula (I).

THERAPEUTIC AGENTS

The invention provides a compound of formula (I): wherein R1, and W have any of the values defined in the application; or a salt thereof. The compounds and salts thereof have beneficial therapeutic properties (e.g. immunosuppressant properties).

PIPERIDINE INHIBITORS OF JANUS KINASE 3

The present invention relates to a new piperidine inhibitors of Janus Kinase 3 activity, pharmaceutical compositions thereof, and methods of use there-of.

Investigation of practical routes for the kilogram-scale production of cis-3-methylamino-4-methylpiperidines

Two routes for the synthesis of cis-N-protected-3-methylamino-4- methylpiperidine (3) were examined: a route hinging on the electrochemical oxidation of carbamate 1 to install a ketone at the 3 position of the piperidine followed by reductive animation (disconnection A), and a route involving the hydrogenation of an appropriately functionalized pyridine (disconnection B). While both routes to the desired compound were ultimately successful, the pyridine hydrogenation approach proved to be more amenable to kilogram-scale preparations due to the crystallinity and purity of intermediates in that route.

3-Amino-piperadine derivatives and methods of manufacture

This invention relates to 3-amino piperadine derivatives, their intermediates and methods of manufacture. As such, the present invention includes methods of making a compound of the formulas (Ia) and (Ib) wherein R1, R2, R3/sub