133737-32-3

Usage

Uses

Anti-anxiety agent.

Brand name

Bextra (Interneuron).

InChI:InChI=1/C23H22ClN3O2/c1-14(2)7-10-16(28)13-19-17-5-3-4-6-18(17)23(29)27(19)21-12-9-15-8-11-20(24)25-22(15)26-21/h3-6,8-9,11-12,14,19H,7,10,13H2,1-2H3

Upstream product

• 136604-91-6 [(5-methyl-2-oxo)hexyl]triphenylphosphonium bromide 
• 42809-49-4 6-methyl-1-hepten-3-one 
• 100-52-7 benzaldehyde 
• 55243-02-2 2,7-dichloro-1,8-naphthyridine 
• 33779-03-2 2-(2-methoxycarbonylethyl)benzoic acid 
• 3849-22-7 (3-oxo-2,3-dihydro-1H-isoindol-1-yl)-acetic acid 
• 55112-41-9 2-hydroxy-7-N-phthalimidyl-1,8-naphthyridine 
• 632620-24-7 2-amino-7-hydroxy-1,8-naphthyridine sulfate 
• 134664-69-0 isoamylcarbonylmethylenetriphenyl phosphorane 
• 55112-38-4 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one 
• 141-86-6 2.6-diaminopyridine 
• 110-12-3 5-Methyl-2-hexanone 
• 147031-30-9 (±)-2-[1-(7-chloro-1,8-naphthyridin-2-ylamino)-6-methyl-3-oxoheptyl]benzoic acid 
• 15944-33-9 2-chloro-7-amino-1,8-naphthyridine 

Downstream Products

• 147031-30-9 (±)-2-[1-(7-chloro-1,8-naphthyridin-2-ylamino)-6-methyl-3-oxoheptyl]benzoic acid 

Relevant academic research and scientific papers

Preparation method of anti-anxiety drug pagoclone or pazinaclone

The invention discloses a method for catalytically synthesizing an anti-anxiety drug pagoclone or pazinaclone and analogues thereof by utilizing Rh(III). The method comprises the following steps: reacting benzaldehyde and 2-aminopyridine compounds in a solvent in the presence of a rhodium catalyst and acetate, and producing an effective guide group in situ; and reacting the guide group and substituted olefin under rhodium catalysis, and performing after-treatment after the reaction is completed, thereby obtaining a compound having a nitrogen heterocyclic framework. According to the preparationmethod, two independent reactions (amide formation and carbon-hydrogen activation) are catalyzed by using rhodium, and a synthetic strategy of self-assembling high-efficiency guide groups is successfully realized. The reaction is carried out based on simple raw materials, an isoindoxone skeleton having substitution characteristics is synthesized in a simple and mild catalytic system by utilizinga 'one-pot process', the operation is simple and convenient, the reaction conditions are mild, the yield is high, and atom economy is high.

Multicomponent Synthesis of Isoindolinones by RhIII Relay Catalysis: Synthesis of Pagoclone and Pazinaclone from Benzaldehyde

A practical one-pot isoindolinone synthesis enabled by RhIII catalysis was developed. The advantage of this protocol is that it does not require pre-preparation of amide substrates, because RhIII participates in two reactions independently. This mild, operationally multicomponent process transforms a wide variety of commercially available aldehydes into the corresponding γ-lactams in good yields, thereby demonstrating that N-pyridin-2-yl benzamide is an effective directing group. Notably, the anxiolytic drugs pagoclone and pazinaclone can be directly prepared by this methodology.

Cu/Fe Catalyzed Intermolecular Oxidative Amination of Benzylic C-H Bonds

We report a Cu/Fe co-catalyzed Ritter-type C-H activation/amination reaction that allows efficient and selective intermolecular functionalization of benzylic C-H bonds. This new reaction is featured by simple reaction conditions, readily available reagents and general substrate scope, allowing facile synthesis of biologically interesting nitrogen containing heterocycles. The Cu and Fe salts were found to play distinct roles in this cooperative catalysis. With a little help: A Ritter-type intermolecular amination of benzylic C-H bonds with acetonitrile, co-catalyzed by CuII/FeIII is reported. A wide array of biologically interesting nitrogen containing heterocycles was prepared from 2-alkyl benzoic acids and heteroaromatic carboxylic acids under operationally simple conditions. The Cu and Fe salts were found to play distinct roles in this cooperative catalysis.

Methods for making 2-(7-chloro-1,8-naphthyridine-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isoindolinone

The present invention relates to methods for making racemic 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone and (+)-2-(7-chloro-1,8-naphthyridine-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isoindolinone.

An Efficient and Cost-Effective Synthesis of Pagoclone

The compound (+)-2-(7-chloro-1,8-naphthyridin-2-yl)-3S-(5-methyl-2- oxohexyl)-l-isoindolinone (pagoclone) shows anxiolytic activity due to partial agonism of the benzodiazepine site of the GABAA receptor. We describe the development of an economical and practical process for a 100+ kg pilot plant production used to supply development needs. For the key reaction, a β-keto phosphonium salt was prepared by selectively reacting a primary α-bromo ketone with triphenylphosphine in the presence of a secondary α-bromo ketone. A novel Wittig reaction with a 1-isoindolinone was used to produce racemic pagoclone. The enantiomerically pure drug substance was prepared by hydrolyzing a γ-lactam and resolving the resulting enantiomeric carboxylic acids with (+)-ephedrine hemihydrate. An alternate resolution, involving chiral multicolumn chromatography (MCC) was also developed. The synthesis was completed by a racemization-free lactam formation to afford pagoclone.

2-amino naphthyridine derivative, its preparation and its use

The present invention relates to a novel 2-aminonaphthyridine compounds that are useful in preparing a 2-isoindolinyl napthyridine compound that exhibits remarkable anxiolytic, hypnotic, anticonvulsant, antiepileptic and muscle-relaxant properties. The in

Pyrrole derivatives, and pharmaceutical compositions which contain them and pharmacological methods of use

Pyrrole derivatives of formula (I): STR1 in which A forms with the pyrrole ring an isoindoline, 6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine, 2,3,6,7-tetrahydro-5H-[1,4]oxathiino[2,3-c]pyrrole or 2,3,6,7-tetrahydro-5H-[1,4]dithiino[2,3-c]pyrrole ring-system, Het=naphthyridinyl, pyridyl or quinolyl which are unsubstituted or substituted with halogen, (1 to 4 C) alkyl, (1 to 4 C) alkyloxy, (1 to 4 C) alkylthio or CF3, Y=CO, C=NOH or CHOH and R=(3 to 10 C) alkenyl, alkyl which is unsubstituted or substituted with OH, alkyloxy, alkylthio, (3 to 6 C) cycloalkyl, NH2, alkylamino, dialkylamino, alkylcarbonylamino, piperazinyl, piperidyl, 1-azetidinyl, morpholino, pyrrolidinyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, (1-piperazinyl)carbonyl, piperidinocarbonyl, pyrrolidinocarbonyl, phenyl, pyridyl, 1-imidazolyl or alternatively R=2- or 3-pyrrolididnyl, 2-, 3- or 4-piperidyl, (3 to 6 C) cycloalkyl or phenyl which is unsubstituted or substituted with halogen, (1 to 4 C) alkyl, (1 to 4 C) alkyloxy, (1 to 4 C) alkylthio, the said alkyl radicals and portions containing, except where specifically stated, 1 to 10 C, and the piperazinyl, piperidino, piperidyl, pyrrolidinyl, azetidinyl radicals being unsubstituted or substituted at any position by alkyl, alkylcarbonyl, benzyl or hydroxyalkyl, or can alternatively form a lactam group with the nitrogen atom of the ring, and their salts and optical isomers are useful as anxiolytics.