175340-20-2

Basic information

• Product Name: S 18986
• Synonyms: S 18986;1H-Pyrrolo[2,1-c][1,2,4]benzothiadiazine, 2,3,3a,4-tetrahydro-, 5,5-dioxide, (3aS)-;(3aS)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine 5,5-dioxide
• CAS NO: 175340-20-2
• Molecular Formula: C10H12N2O2S
• Molecular Weight: 224.27948
• Mol File: 175340-20-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: S 18986(CAS DataBase Reference)
• NIST Chemistry Reference: S 18986(175340-20-2)
• EPA Substance Registry System: S 18986(175340-20-2)

Safety Data

• Hazardous Substances Data: 175340-20-2(Hazardous Substances Data)

Usage

Uses

S 18986 is a novel cognitive enhancer.

Upstream product

• 37121-62-3 2,3-Dihydro-1H-pyrrolo<2,1-c><1,2,4>benzothiadiazin-5,5-dioxid 
• 3306-62-5 2-AMINOBENZENESULFONAMIDE 
• 4826-18-0 5,5-dioxo-3,5-dihydro-2H-5λ⁶-benzo[e]pyrrolo[2,1-c][1,2,4]thiadiazin-1-one 

Relevant articles and documents

Enantioselective synthesis of a pyrrolo-benzothiadiazine derivative S 18986, a new AMPA receptor positive modulator

Enantioselective reduction of pyrrolo-benzothiadiazine 6 using various chiral reducing agents has been studied and led to efficient synthesis of 8 (S 18986) which was established to be of (S) configuration by single crystal X-ray diffraction analysis. S 18986 is a potent and selective AMPA positive modulator which displays total stereoselectivity, the (R) enantiomer being completely inactive.

The synthesis of S 18986, a chiral AMPA receptor modulator, via catalytic asymmetric hydrogenation

The asymmetric hydrogenation of a dihydropyrrolo-benzothiadiazine dioxide 1 with a diphosphine ruthenium diamine catalyst has been used to synthesize the AMPA receptor positive modulator tetrahydropyrrolo-benzothiadiazine dioxide 2 (S 18986) in high enantiomeric excess. The use of factorial experimental design led to significant improvements in the process parameters and improved enantioselectivity.

Process for the synthesis of (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4] benzothiadiazine

Process for the industrial synthesis of (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H-pyrrolo-[2,1-c][1,2,4]benzothiadiazine of formula (I): by enantioselective catalytic hydrogenation of 5,5-dioxo-2,3-dihydro-1H-pyrrolo-[2,1-c][1,2,4]benzothiadiazine.

Benzothiadiazine compound

A compound of formula (I): STR1 in the form of its S enantiomer, its addition salts with a pharmaceutically acceptable acid or base and medicinal product containing the same are useful for the treatment or prevention of pathologies associated with dysfunction of glutamatergic neurotransmission.