426844-23-7

Usage

Uses

Used in Pharmaceutical and Chemical Research:
4-CIS-FLUORO-L-PROLINAMIDE HYDROCHLORIDE is used as a research compound for the development of therapeutic drugs. Its unique structure and properties make it a valuable building block in the synthesis of complex molecules, contributing to the advancement of medicinal chemistry.
Used in the Development of Therapeutic Drugs:
4-CIS-FLUORO-L-PROLINAMIDE HYDROCHLORIDE is used as a potential therapeutic agent in the development of new pharmaceutical products. Its properties and structure make it a promising candidate for further investigation and application in the treatment of various medical conditions.
Used in Antibacterial and Antifungal Applications:
4-CIS-FLUORO-L-PROLINAMIDE HYDROCHLORIDE has been studied for its potential antibacterial and antifungal properties. It is used as a candidate for the development of new pharmaceutical products with antimicrobial activity, offering potential benefits in the treatment of bacterial and fungal infections.
Used in the Synthesis of Complex Molecules:
4-CIS-FLUORO-L-PROLINAMIDE HYDROCHLORIDE is used as a key component in the synthesis of complex molecules, particularly in the field of medicinal chemistry. Its unique structure and properties make it a valuable building block for the creation of new compounds with potential therapeutic applications.

InChI:InChI=1/C5H9FN2O.ClH/c6-3-1-4(5(7)9)8-2-3;/h3-4,8H,1-2H2,(H2,7,9);1H/t3-,4-;/m0./s1

Upstream product

• 203866-14-2 (2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid 
• 426844-26-0 tert-butyl (2S,4R)-2-carbamoyl-4-fluoropyrrolidine-1-carboxylate 
• 88050-17-3 N-Fmoc-trans-4-Hydroxy-L-Proline 
• 1235447-40-1 (2S,4S)-N-Fmoc-4-fluoropyrrolidine-2-carbonyl fluoride 
• 1235447-46-7 (2S,4S)-N-Fmoc-4-fluoropyrrolidine-2-carboxamide 
• 748165-40-4 (2S,4S)-4-fluoropyrrolidine-2-carboxamide 
• 203866-13-1 (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid 
• 426844-22-6 tert-butyl (2S,4S)-2-carbamoyl-4-fluoropyrrolidine-1-carboxylate 

Downstream Products

• 596817-05-9 (2S,4S)-N-chloroacetyl-4-fluoropyrrolidine-2-carboxamide 
• 596817-06-0 (2S,4S)-1-(2-chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile 

Relevant academic research and scientific papers

4-fluoropyrrolidine-2-carbonyl fluorides: Useful synthons and their facile preparation with 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride

4-Fluoropyrrolidine derivatives are useful in medicinal chemistry applications such as dipeptidyl peptidase IV inhibitors. As attractive synthons for these, N-protected (2S,4S)-4-fluoropyrrolidine-2-carbonyl fluorides were synthesized in high yield by double fluorination of N-protected (2S,4R)-4-hydroxyproline with 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead). The 4-fluoropyrrolidine-2-carbonyl fluorides were converted to useful intermediates such as 4-fluoropyrrolidine-2-carboxamides, -N-methoxy-N-methylcarboxamide (Weinreb amide), -carboxylate methyl esters, and -carbonitriles in excellent yields. The crystalline N-Fmoc-cis-4- fluoropyrrolidine-2-carbonyl fluoride 2a is a particularly useful synthon due to its high yield of preparation and easy isolation as an enantiomerically pure compound by crystallization. Thus, the methodology using the synthons prepared by the stereospecific double fluorination has enabled a significant decrease in the synthetic steps needed for the preparation of the 4-fluoropyrrolidine derivatives useful for medicinal applications.

ETHER DERIVATIVES OF BICYCLIC HETEROARYLS

The invention relates to compounds of formula (I), wherein the substituents are as defined in the specification; to processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; such compounds as a medicament; such compounds for the treatment of a proliferative disease

NOVEL 4-FLUOROPYRROLIDINE-2-CARBONYL FLUORIDE COMPOUNDS AND THEIR PREPARATIVE METHODS

Novel 4-fluoropyrrolidine-2-carbonyl fluoride compounds as useful fluorinated intermediates are disclosed. Their preparative methods are also disclosed. Useful applications of the 4-fluoropyrrolidine-2-carbonyl fluorides are shown.

NOVEL PROCESSES FOR THE PREPARATION OF DPP IV INHIBITORS

The present invention relates to novel processes for preparing DPP-IV inhibitors having the structure of formula I, and pharmaceutically acceptable salt thereof, which are useful for treatment of Type 2 diabetes.

Synthesis and structure-activity relationships of potent 1-(2-substituted-aminoacetyl)-4-fluoro-2-cyanopyrrolidine dipeptidyl peptidase IV inhibitors

Dipeptidyl peptidase IV (DPP-IV) inhibitors have attracted attention as potential drugs for use in the treatment of type 2 diabetes because they prevent the degradation of glucagon-like peptide-1 (GLP-1) and extend its duration of action. We previously reported that 2-cyano-4-fluoropyrrolidines act as potent DPP-IV inhibitors and have been modifying the 1-position of pyrrolidine to obtain more useful inhibitors. An L-tert-butylglycine derivative was found to be a stable and potent DPP-IV inhibitor that exhibits a glucose lowering effect in vivo. Here, we report the synthesis of and biological data on the aforementioned derivatives.

NOVEL DIPEPTIDYL PEPTIDASE INHIBITORS AND PROCESSES FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

The present invention relates to novel compounds representated by formula (I), where R, R1, R2, R3, X, Y, m, n are as defined.The present invention relates to compounds of the general formula I their derivatives, their analogs, their tautomeric forms, their stereoisomers, their diastereomers, their bioisosteres, their polymorphs, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them which are predominantly dipeptidyl peptidase IV inhibitors. The present invention also relates to the processes for the preparation of novel compounds of formula (I) and their use in treating type II diabetes and diabetic complications thereof and also for treating dislipidemia, hypercholesterolemia, obesity and hyperglycemia.

CYANOFLUOROPYRROLIDINE DERIVATIVE

A cyanofluoropyrrolidine compound of Formula (I) or a pharmaceutically acceptable salt thereof or a hydrate thereof, which is useful as an agent for preventing or treating diseases or conditions capable of being improved by inhibition of dipeptidyl peptidase IV (DPPIV), diabetes mellitus, immune diseases and the like: [wherein A represents a hydrogen atom or a fluorine atom, R1 and R2 are as defined in the specification, X represents a single bond or a C1-3 alkylene group, and R3 represents a group represented by the formula: -N(R4)COR5, -N(R4)SO2R5, -NR4R6, -SO2R5, -SO2NR4R5, -OCONR4R5, -CH=CH-R7 or -C≡C-R7, or represents a heteroaryl group selected from a heteroaryl group which contains at least one oxygen and/or sulfur atom and which may further contain a nitrogen atom, and a 6-membered nitrogen-containing aromatic ring or a 9- to 11-membered condensed ring thereof (wherein the heteroaryl group may be substituted with one or more substituents selected from the substituent Y3 group)].

NOVEL 5-SUBSTITUTED INDOLE DERIVATIVES AS DIPEPTIDYL PEPTIDASE IV (DPP-IV) INHIBITORS

The present invention relates to 5-substituted indole derivatives of formula (I): having inhibitory potential of dipeptidyl peptidase IV (DPP IV) enzyme where x and R1 are defined as defined in the specification

PROCESS FOR PRODUCTION OF CIS-4-FLUORO-L-PROLINE DERIVATIVES

The present invention provides a safer method for production of a cis-4-fluoro-L-proline derivative under milder conditions and in good yield to give a product of high purity on an industrial scale at low cost. Namely, the present invention provides a method for producing a cis-4-fluoro-L-proline derivative, which comprises reacting a trans-4-hydroxy-L-proline derivative of the following Formula [I]: (wherein R1 represents a protecting group for an α-amino group, and R2 represents a protecting group for a carboxyl group) with N,N-diethyl-N-(1,1,2,3,3,3-hexafluoropropyl)amine in the presence of a hydrogen fluoride-scavenger.

2-CYANOPYRROLIDINECARBOXAMIDE COMPOUND

A compound of the formula (I) or a pharmaceutically acceptable salt thereof: [wherein X1 and X2 each is independently lower alkylene; X3 is =CH2, =CHF or =CF2; R1 is substituent, R2 and R3 each is independently H or lower alkyl; n is 0, 1, 2, 3 or 4.] having the activity inhibiting DPP-IV activity. They are therefore useful in the treatment of conditions mediated by DPP-IV, such as NIDDM.