KinasePro

Kinase Chemistry – Just a year and a half behind the times.

AV-412

Posted by kinasepro on October 23, 2006

>> Update: Revise the structures to the acrylamide as in WO/2007/103233.

Hello Hello Aveo,EGFR Phase one recruitment initiated. Red Team, Blue Team, Go! Go! Go!

I see you’ve liscenced this AV-412 / MP-412 thingamajig, from Mitsubishi Pharma which had KinasePro a little worried at first, since he doesn’t like slogging through Japanese patents. Luckily for him though, the patents are written in english. More luckier: There’s only two real compounds in the claims.

Most of the kinasefans out here will already recognize this is bound to be a quinazoline patent, the only question is how did they get around the deluge of Tarceva / Iressa knock-offs. EP1690856 seems to be the only EGFR series coming from Mitsubishi:

Yep that’ll do. But only 2 compounds? Well so it is… In case your joining the party late. Tarceva bound to EGFR is: 1m17 and 1XKK also looks interesting when trying to interperet the above structures. So much for that region merely being accessible to sovlent, eh?

CC(N4CCN(C)CC4)(C)C#CC1=C(NC(CCOC5=CC=CC=C5)=O)C=C2C(N=CN=C2NC3=CC(Cl)=C(F)C=C3)=C1 CC(N4CCN(C)CC4)(C)C#CC1=C(NC(CCS(C5=CC=CC=C5)(=O)=O)=O)C=C2C(N=CN=C2NC3=CC(Cl)=C(F)C=C3)=C1

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3 Responses to “AV-412”

  1. kinasepro said

    Finkelstein on a quinazoline?  This is from the EP application.  I may have to try this just to have something to post up on Org Prep Daily!

    (EXAMPLE 1) 7-iodo-6-nitro-4-(3H)-quinazolinone:

    7-chloro-6-nitro-4 (3H)-quinazolinone (50.0 g, 222 mmol) and sodium iodide (332 g, 2216 mmol) were added to N-methylpyrrolidone (500 mL), and were stirred for 5 h at 170°C.

    The reaction solution was poured into water (1500 mL) and was stirred for 1 h.

    The precipitated crystals were collected by filtration, and after washing with water, were dried under reduced pressure to obtain 7-iodo-6-nitro-4 (3H)-quinazolinone (1) (44.7 g, 64%)
    O=C1NC=NC2=C1C=C([N+]([O-])=O)C(I)=C2

  2. milkshake said

    But they heat the hell out of it. With 10 equivs of NaI and the NMP pudding for a solvent, it has to go.

    I was more surprised when I saw this Cl/Br exchange for I on non-activated aromatics with a transition metal, Co or Ni salt if I remember correctly.

  3. kinasepro said

    Humbug, doesn’t look available anyway. Guess I’ll have to find something else fun to try.

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