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August 6, 2007
Here, Fix This, Would You?
As I mentioned the other day, drug companies manage the shift from med-chem to process in a lot of different ways. (For those outside the industry, the medicinal chemists are focused on making relatively small amounts of a lot of different compounds, while the process labs concentrate on making large amounts of a few). Some places allow the med-chem labs to use whatever wild chemistry they can think up, on the theory that if a compound is really interesting the process labs will find a way to make it on scale. Others strongly discourage some kinds of chemistry (particularly nasty solvents and reagents), since real problems can occur if a lead compound comes from that sort of background.
I incline more to the latter. Perhaps it's just a dislike of leaving messes for other people to clean up. But I'm not as pure as I might sound, because I have done some ugly reactions (mercury, organoazides, etc) in my med-chem analoging, and these were real possibilities for trouble if the compounds had ever taken off (they didn't). In these cases, the unappealing reactions were by far the fastest way into the compounds I wanted, and I figured that I'd take a quick look and see if they were any good. (The same reasoning, I'm sure, had led to most of nightmares that process groups find themselves in).
Other things being equal, though, I'd rather approach my drug analogs using something that isn't demonstrably foul. I suppose that's as good a middle ground as any - try not to use hideous reagents, but if they're the quick way into a series, go ahead - but be mindful of the tradeoff you're making. If you go the next step, where the ugly stuff is (as far as you can tell) the only way into a series, then you're taking a real risk and should only do it with a reasonable expectation that it'll be worth it. It's very hard to have reasonable expectations of that kind in medicinal chemistry, though - which is why this sort of thing shouldn't become a habit.
The comments that came in to my recent post on this topic were all over the place - I wouldn't mind seeing an informal head count of how various departments feel on this issue. If we get a decent sample, I'll post on the results.
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