109384-24-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to provide specific stereochemistry. This is crucial in the development of drugs that depend on the precise arrangement of atoms in three-dimensional space for their efficacy and safety.
Used in Medical Research:
In the field of medical research, (2S,4R)-1-Boc-2-carbamoyl-4-hydroxypyrrolidine serves as a valuable compound for studying the effects of stereochemistry on drug action and metabolism. Its stable chiral configuration allows researchers to explore the nuances of drug interactions with biological targets, potentially leading to the discovery of more effective and safer medications.

InChI:InChI=1/C10H18N2O4/c1-10(2,3)16-9(15)12-5-6(13)4-7(12)8(11)14/h6-7,13H,4-5H2,1-3H3,(H2,11,14)/t6-,7+/m1/s1

Upstream product

• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 80029-43-2 1-hydroxybenzotriazol-hydrate 
• 1336-21-6 ammonium hydroxide 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 483366-12-7 (2S,4R)-N-Boc-2-cyano-4-hydroxypyrrolidine 
• 928776-72-1 5-benzyloxy-2-(5-tert-butyldimethylsilyloxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 
• 928776-73-2 5-benzyloxy-2-(5-hydroxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of potent 3- or 4-substituted-2-cyanopyrrolidine dipeptidyl peptidase IV inhibitors

A series of 3- or 4-substituted-2-cyanopyrrolidines were synthesized and evaluated as 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 degradation of glucagon-like peptide-1 (GLP-1) and extend its duration of action. A series of 2-cyanopyrrolidines are among the most potent of DPP-IV inhibitors. We focused our attention on substitutions at the 3- or 4-position of 2-cyanopyrrolidines and synthesized and evaluated various derivatives. Among them, the 4-fluoro derivative was found to exhibit better DPP-IV inhibitory activity and higher plasma drug concentrations after oral administration to rats than the 4-unsubstituted derivative. We report here on the synthesis and biological data of the aforementioned derivatives.

2-CYANOPYRROLDINES, -PIPERIDINES OR -DAZEPINES AS HYPERGLYCEMIC AGENTS

Nitrogen containing compounds of Formula (I), pharmaceutical compositions comprising these compounds and their use in treating hypoglycaemia is disclosed.

(4-HYDROXYPYRROLIDIN-2-YL)-HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to bifunctional compounds of formula (I), which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands of formula (III).

DICYCLOAZAALKANE DERIVATES, PREPARATION PROCESSES AND MEDICAL USES THEREOF

Disclosed are new dicycloazaalkane derivates represented by general formula (I), preparation processes and pharmaceutical compositions containing them, and the uses for treatment especially for dipeptidyl peptidase inhibitor (DPP-IV), in which each substitute group of general formula (I) is as defined in specification.

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.

Mono- and dihydroxylated metabolites of thalidomide: Synthesis and TNF-α production-inhibitory activity

Mono- and dihydroxylated metabolites of thalidomide were efficiently prepared and characterized, and their inhibitory activity on tumor necrosis factor (TNF)-α production in the human monocytic leukemia cell line THP-1 was evaluated. 5,N-Dihydroxythalidomide was a much more potent TNF-α production inhibitor than thalidomide.

cis-2,5-dicyanopyrrolidine inhibitors of dipeptidyl peptidase IV: Synthesis and in vitro, in vivo, and x-ray crystallographic characterization

Inhibitors of the glucagon-like peptide-1 (GLP-1) degrading enzyme dipeptidyl peptidase IV (DPP-IV) have been shown to be effective treatments for type 2 diabetes in animal models and in human subjects. A novel series of cis-2,5-dicyanopyrrolidine α-amino amides were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. 1-({[1-(Hydroxymethyl)cyclopentyl]amino}-acetyl)pyrrolidine-2,5-cis- dicarbonitrile (1c) is an achiral, slow-binding (time-dependent) inhibitor of DPP-IV that is selective for DPP-IV over other DPP isozymes and proline specific serine proteases, and which has oral bioavailability in preclinical species and in vivo efficacy in animal models. The mode of binding of the cis-2,5-dicyanopyrrolidine moiety was determined by X-ray crystallography. The hydrochloride salt of 1c was further profiled for development as a potential new treatment for type 2 diabetes.

NEW COMPOUNDS

The present invention relates to the novel compounds of the general formula (I) possessing DPP-IV inhibitory activity. These compounds contain tropane building blocks.

CYANOPYRROLIDINE DERIVATIVES

A cyanopyrrolidine derivative represented by Formula (1): [wherein R1 is a halogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, R2 is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, or R1 and R2 together form an oxo, a hydroxyimino group, an alkoxyimino group having 1 to 5 carbon atoms or an alkylidene group having 1 to 5 carbon atoms, ???R3 and R4 are each a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms or an alkyl group having 1 to 5 carbon atoms, or R3 and R4 together form an oxo, a hydroxyimino group, an alkoxyimino group having 1 to 5 carbon atoms or an alkylidene group having 1 to 5 carbon atoms, ???X is an oxygen atom or a sulfur atom, ???Y is -CR5R6- (wherein R5 and R6 are the same or different, and are each a hydrogen atom, a halogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms or an optionally substituted alkenyl group having 2 to 10 carbon atoms), or -CR7R8-CR9R10- (wherein R7, R8, R9 and R10 are the same or different, and each a hydrogen atom, a halogen atom or an optionally substituted alkyl group having 1 to 10 carbon atoms, or R7 and R9 together with the carbon atom to which they are attached form an optionally substituted cycloalkyl group having 3 to 8 carbon atoms, an optionally substituted cycloalkenyl group having 4 to 8 carbon atoms, an optionally substituted bicycloalkyl group having 5 to 10 carbon atoms, or an optionally substituted bicycloalkenyl group having 5 to 10 carbon atoms) and ???Z is a hydrogen atom or an optionally substituted alkyl group having 1 to 10 carbon atoms, or Y and Z together with the nitrogen atom to which they are attached form an optionally substituted cyclic amino group having 2 to 10 carbon atoms], or a pharmaceutically acceptable salt thereof.

2-(heterocyclylthio)carbapenem derivatives, their preparation and their use as antibiotics

Compounds of formula (I): STR1 in which Ra is a group of formula (II): STR2 or a group of formula (III): STR3 (where one of R' is a bond to the remainder of the compound, one more of R' is R2 and the others of R' are all hydrogen), R1 is hydrogen or methyl, R2 is hydrogen, optionally substiuted alkyl, halogen, hydroxy, alkoxy, amino, alkanoylamino, alkanoyloxy, alkanoyl, carboxy, alkoxycarbonyl, cyano, --S(O)j R9 (where j is 0, 1 or 2 and R9 is alkyl), or --CONR6 R7 (which is optionally substituted carbamoyl or heterocyclyl-carbonyl), R2a is hydrogen, alkyl or alkanoyl, --NR3 R4 is optionally substituted amino or heterocyclic, and --COOR5 is carboxy, --COO-, --COOMx (where M is a cation and x is the reciprocal of the valence of the cation M) or protected carboxy and, where --COOR5 is carboxy, --COOMx or protected carboxy, the compound of formula (I) also contains an anion; l, m and n are independently 0, 1, 2 or 3, provided that (m+n) is an integer from 2 to 6; p is 0, 1 or 2; Y is a single bond, oxygen, sulfur or R8 N8 is hydrogen, alkyl or alkanoyl) and pharmaceutically acceptable salts and esters thereof are potentially valuable antibiotics.