Azetidine derivatives, preparation, pharm.

[pHarmacist]

Patent US6479479

1-2-3 ACiD

[Rhodium]

A lot of interesting chemistry, I agree, but exactly what had you in mind?

[pHarmacist]

Besides very interesting chem, I agree on that one, I also got suprised when I (reading this patent) found how broad applications these familly of substances can have.

...chronic treatments and alcohol or drug abuse (opioids, barbiturates, cannabis, cocaine, amphetamine, phencyclide, hallucinogens, benzodiazepines for example), as analgesics or potentiators of the analgesic activity of the narcotic and nonnarcotic drugs....
 

Interesting property:
"...The compounds of formula (I) exhibit advantageous pharmacological properties. These compounds possess a high affinity for the cannabinoid receptors..."

Wouldn't you agree?
1-2-3 ACiD

[Rhodium]

When you have read a few more patents, you'll be surprised about how broad usage every patented molecule has, and in addition to that they can go on for several pages with structural modifications that can be done while the authors pretend they all have the same effect.

It is just a commercial thing. They exaggerate as much as legally possible.

[pHarmacist]

I wouldn't know relly, I don't know anything about patent-law and commercial/legal issues when it comes to patenting. I guess you're right. But I was mostly amazed to come across a familly of compuonds that looked as promising as for instance indole familly, meaning that they can be used in lot of different areas when it comes to human body/mind...
1-2-3 ACiD

[Rhodium]

I don't think the compound itself is interesting per se, but there were sure a lot of exciting reactions (with references) in it. For example formation of mesylates from alcohols, followed by amination - I saw you were looking for such references earlier.

[pHarmacist]

Indeed!! So you remember!! I read it, very good information, all I neded to know actually, I actually came across that patent when I was looking for formation of mesylates from alcohols...

Why isn't this approach popular when it comes to amination of (MD)P2Pol? I can't understand that...

1-2-3 ACiD

[Rhodium]

...because noone at the Hive has ever used any route going through (MD)P2Pol, that is besides Siegfried -

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mdma.tosylate.html

The reason for this is the existance of safrole (as long as that is available, pepple in general aren't going to use another route to MDMA), and the existance of pseudoephedrine (which is what the methheads will use).

Sometimes I really hope for a tight ban on both of the, so that we could get some really interesting chemistry going...    

PS: If you stay here for a while, you'll be amazed how unimportant stuff from the Hive I'll remember for years... I don't know how I do it, but I somehow remember almost all the discussions I have read here the last 1-2 years, half of the ones 2-3 years old, and so on... It is in one way a good thing, but I wish I could trade some of this memory for some short-term memory instead. I always misplace my cellphone, forget to call places and names of people. As late as today I forgot I was supposed to go to school...

[Cyrax]

I remember that a important side reaction with the mesylate / tosylate is elimination (it's discussed in a french article of you - Rhodium, that was translated by Hypo [if my memory serves me right]).  That's why I think it's better to work with the ketone ...

pHarmacist, if you are looking for procedures to mesylate or tosylate alcohols, check out

Post 336537

(Cyrax: "Tosylate and friends", Chemistry Discourse)

[pHarmacist]

Cool man, good post!!! Informative too! great work  
1-2-3 ACiD

[Ritter]

Hey Rodium,

I can think of at least one other guy who did some work with the amination of MDP2Pol tosylates