S33005 is a

serotonin–norepinephrine reuptake inhibitor Serotonin–norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant drugs used to treat major depressive disorder (MDD), anxiety disorders, obsessive–compulsive disorder (OCD), social phobia, attention-deficit hyperactivity di ...

(SNRI) that was under

development Development or developing may refer to: Arts *Development hell, when a project is stuck in development *Filmmaking, development phase, including finance and budgeting *Development (music), the process thematic material is reshaped * Photograph ...

Servier Servier Laboratories (French: Laboratoires Servier, often abbreviated to Servier) is an international pharmaceutical company governed by a non-profit foundation, with its headquarters in France (Suresnes). The consolidated turnover for the 2018 ...

for the treatment of depression and related disorders. It is structurally related to

venlafaxine Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic ...

but has a more complex molecular structure. Venlafaxine appears to be a sigma modulator, but it is not known if S33005 shares this activity.

Synthesis

"The 1-cyano-benzocyclobutenes used as starting material are obtained, for example, by subjecting a β- rthohalogeno-phenyl

propionitrile Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to oth ...

to intramolecular condensation in the presence of

potassium amide Potassium amide is an inorganic compound with the chemical formula . Like other alkali metal amides, it is a white solid that hydrolyzes readily. It is a strong base. Production Potassium amide is produced by the reaction of ammonia with potassium ...

, or by brominating a

benzocyclobutene Benzocyclobutene (BCB) is a benzene ring fused to a cyclobutane ring. It has chemical formula . BCB is frequently used to create photosensitive polymers. BCB-based polymer dielectrics may be spun on or applied to various substrates for use in ...

in position 1 with ''N''-bromosuccinimide, followed by exchange of the bromine atom for a cyano group by means of

sodium cyanide Sodium cyanide is a poisonous compound with the formula Na C N. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its hi ...

References

External links

PubMed search

Binding Database
* The patent and synthesis discussion can be found in {{Navboxes , title =

Pharmacodynamics Pharmacodynamics (PD) is the study of the biochemical and physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or combinations of organisms ...

, titlestyle = background:#ccccff , list1 = {{Monoamine reuptake inhibitors {{Sigma receptor modulators Tertiary alcohols Antidepressants Benzocyclobutenes Phenol ethers Serotonin–norepinephrine reuptake inhibitors Sigma agonists

Synthesis

See also

References

External links