Delving into the Latest Updates on BMS-505130 with Synapse

Overview

Basic Info

Drug Type

Small molecule drug

Synonyms

BMS-5051, BMS-505130, C11-BMS-505130

Target

SERT

Action-

Mechanism

Serotonin reuptake inhibitors

Therapeutic Areas

Urogenital Diseases

Active Indication-

Inactive Indication

Male sexual dysfunctionPremature Ejaculation

Originator Organization

Bristol Myers Squibb Co.

Active Organization-

Inactive Organization

Bristol Myers Squibb Co.

License Organization-

Drug Highest PhasePendingPreclinical

First Approval Date-

Regulation-

Structure/Sequence

Molecular FormulaC19H21N3O4

InChIKeyQYXJWBDKQAIHJM-ZMPXXIOZSA-N

CAS Registry859230-84-5

Process development of a selective serotonin reuptake inhibitor (1) is described.The synthesis features Nishiyama catalyst-mediated asym. cyclopropanation of vinyl indole 2 with ethyldiazoacetate to install the trans-disubstituted cyclopropane.The active pharmaceutical ingredient (1) was prepared in 13 chem. steps with 9 isolations and proceeded in an overall yield of 34%.

01 Jun 2005·Organic lettersQ1 · CHEMISTRY

Catalytic Asymmetric Diazoacetate Cyclopropanation of 1-Tosyl-3-vinylindoles. A Route to Conformationally Restricted Homotryptamines

Q1 · CHEMISTRY

Article

Author: Denhart, Derek J. ; Mattson, Ronald J. ; Marcin, Lawrence R.

[reaction: see text] Substituted 1-tosyl-3-vinylindoles undergo catalytic asymmetric cyclopropanation with ethyl- and tert-butyldiazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogues such as BMS-505130.

100 Deals associated with BMS-505130

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R&D Status

10 top R&D records.

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Indication	Highest Phase	Country/Location	Organization	Date
Premature Ejaculation	Preclinical	United States	Bristol Myers Squibb Co.	01 Mar 2005
Male sexual dysfunction	Discovery	United States	Bristol Myers Squibb Co.	-