228857-58-7

Usage

Chemical Properties

White powder

InChI:InChI=1/C9H15NO4/c1-9(2,3)14-8(13)10-5-4-6(10)7(11)12/h6H,4-5H2,1-3H3,(H,11,12)/t6-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 7729-30-8 (R)-azetidine-2-carboxylic acid 
• 2517-04-6 Azetidine-2-carboxylic acid 
• 174740-80-8 (R)-1-tosylazetidine-2-carboxylic acid 
• 7732-18-5 water 

Downstream Products

• 161511-90-6 (R)-1-t-butyloxycarbonyl-2-azetidinemethanol 
• 935668-80-7 (R)-azetidin-2-ylmethanol hydrochloride 
• 1005756-63-7 (R)-tert-butyl 2-(azidomethyl)azetidine-1-carboxylate 
• 887626-82-6 (R)-tert-butyl 2-(aminomethyl)azetidine-1-carboxylate 

Relevant academic research and scientific papers

CHEMICAL COMPOUNDS AS H-PGDS INHIBITORS

A compound of formula (I) wherein R1, R2, R3, R4, X, Y, and A are as defined herein. The compounds of the present invention are inhibitors of hematopoietic prostaglandin D synthase (H-PGDS) and can be useful in the treatment of Duchenne muscular dystrophy. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting H-PGDS activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS

Chemical entities that modulate smooth muscle myosin and/or non-muscle myosin, and chemical entities, pharmaceutical compositions and methods of treatment of diseases and conditions associated with smooth muscle myosin and/or non-muscle myosin are described.

N-HYDROXYAMIDE DERIVATIVES POSSESSING ANTIBACTERIAL ACTIVITY

Novel N-hydroxyamide derivatives are disclosed. These N-hydroxyamide derivatives inhibit UPD-3O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase, an enzyme present in gram negative bacteria and are therefore useful as antimicrobials and antibiotics. Methods of synthesis and of use of the compounds are also disclosed.

PROCESS FOR PRODUCING OPTICALLY ACTIVE AZETIDINE-2-CARBOXYLIC ACIDS

An optically active N-protected azetidine-2-carboxylic acid (5) can be produced by preparing an optically active 4-amino-2-halobutyric acid (3), ???by halogenating an optically active 3-hydroxy-2-pyrrolidinone (1) with inversion of configuration to prepare an optically active 3-halo-2-pyrrolidinone (2) followed by hydrolysis or, ???by halogenating an optically active 4-amino-2-hydroxybutyric acid ester (6) with inversion of configuration to prepare an optically active 4-amino-2-halobutyric acid ester (7) followed by hydrolysis or, ???by halogenating the compound (6) with inversion of configuration to prepare the compound (7), cyclizing the same to prepare the compound (2) followed by hydrolysis,???further cyclizing the compound (3) followed by treating the reaction product with an amino group-protecting agent.The optical purity of the thus-obtained compound (5) can be improved further by recrystallization.

3-Pyridyl enantiomers and their use as analgesics

The present invention relates to a method of controlling pain in mammals, including humans, comprising administering to a mammal or patient in need of treatment thereof selected compounds of formula I: STR1 or a pharmaceutically acceptable salt thereof. The invention further relates to selected (R) and (S) compounds of formula I above which are useful as analgesics as well as neuronal cell death preventors and anti-inflammatories.

3-pyridyloxymethyl heterocyclic ether compounds useful in controlling neurotransmitter release

Novel heterocyclic ether compounds of the formula: STR1 wherein n, *, R1, R2, R3 and y are specifically defined, or pharmaceutically acceptable salts or prodrugs thereof, which are useful in selectively controlling neurotransmitter release; therapeutically-effective pharmaceutical compositions of these compounds; and use of said compositions to selectively control neurotransmitter release in mammals.

Identification and initial structure-activity relationships of (R)-5- (2-azetidinylmethoxy)-2-chloropyridine (ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors

New members of a previously reported series of 3-pyridyl ether compounds are disclosed as novel, potent analgesic agents acting through neuronal nicotinic acetylcholine receptors. Both (R)-2-chloro-5-(2- azetidinylmethoxy)pyridine (ABT-594, 5) and its S-enantiomer (4) show potent analgesic activity in the mouse hot-plate assay following either intraperitoneal (ip) or oral (po) administration, as well as activity in the mouse abdominal constriction (writhing) assay, a model of persistent pain. Compared to the S-enantiomer and to the prototypical potent nicotinic analgesic agent (±)-epibatidine, 5 shows diminished activity in models of peripheral side effects. Structure-activity studies of analogues related to 4 and 5 suggest that the N-unsubstituted azetidine moiety and the 2-chloro substituent on the pyridine ring are important contributors to potent analgesic activity.