Lamentations on Chemistry

So, I’m blundering through the literature on a snipe hunt when I run into this ICI patent- US 5,456,729. In the description, they teach a method of preparing an explosive composition using “lactic casein”. Having been in the dairy business long ago, and specifically having worked in a cottage cheese plant, I recognized this component as … cheese. Well, mostly. Example 5 discloses a composition comprising 25 % ammonium nitrate and 3 % lactic casein.

Unless you have lactose intolerance, cheese is not ordinarily an explosive. In the patent, the lactic casein is one of many examples of a foam stabilizer. Other stabilizers include animal and fish proteins as well as collagens. A collection of other chemical additives rounds off the list.

If they had specified gluten, they could have claimed the use of a pastrami and cheese on rye sandwich as stabilizer feedstock for their explosive composition.

The summer 2008 issue of the Lewis & Clark (Vol 12, No. 2) Law Review is dedicated to the matter of nonobviousness in patent law- Business Law Forum: Nonobviousness — The Shape of Things to Come.

The papers are scholarly articles and are very densely written (sorta like some posts in this blog!!). But if you can tolerate that style or are an insomniac, some of the work seems to be worth plowing through.

Nonobviousness is one of the most vexing aspects of patent law. I find that my natural inclinations about what constitutes obviousness are completely inapplicable to patents. Perhaps one day I’ll get it.

In the chemical technology world, it often happens that one company will engage another in the manufacture of some particular substance. Company A needs a particular material made according to certain specifications. Company A goes to Company B to ask for price and availability.  But first, Company A must disclose the identity and certain particulars of the material to Company B.

For Company A to disclose the identity of its material, it must work out a secrecy agreement with Company B. Company A’s business depends on the material and it does not want Company B to disclose the details of the material, the process, or any other aspect of the business. So, they execute a secrecy agreement.

What is interesting about such arrangements is the great diversity of “language” in the terms among companies. Some companies are very concerned about the faintest smidgeon of errant information and write detailed terms accordingly. Others are much more concerned about the broad strokes and are apparently willing to let the courts work out the details in a conflict.

Some companies are willing to yield on unreasonable terms and conditions while others will fight to the death on even the slightest change.  There is a strong correlation to the corporate culture and the extent to which a company is under a market pull influence (tolling operators) or is engaged in technology push (inventors).

In some companies, issues relating to intellectual property (IP) are strongly influenced by the lawyers.  In such an organization, it sometimes happens that management is completely immobilized by indecision in IP matters. Managers may not understand the IP, are unable to engage their own lawyers in detailed discussion about the issue, or may simply be terrified of making a mistake. Doing business with organizations that are highly rigid in deference to their lawyers tends to be a more difficult activity. The thinking is that if the lawyer makes the decision, then they can take the heat if it goes south. Of course, the lawyer won’t take the heat- they’ll just bill you to get you out of the mess.

In other companies, upper management will take legal advice, but will not leave the decisions to the lawyers. These managers understand that IP is company treasure that must be put to good use in order to bring in revenues. Lawyers get paid irrespective of the outcome in the advice dispensing trade. A good manager knowns how to ride a lawyer like a cutting horse, digging in the spurs now and then to show who’s boss.

IBM people are prodigous inventors. In 2007 alone, IBM was allowed 3,125 US patents. In the period from 1993 through 2007, IBM has acquired 38,707 US patents.  I can visualize the torrents of office actions flooding out of some pipe from the USPTO into the mailroom at IBM Galactic Headquarters.

Imagine trying to enforce this collection of patents. Crimony! With this many patents- and who knows how few are abandoned- IBM must be involved in litigation almost continuously. Imagine the legions of confident, white-shirted IBM attorneys marching in lockstep, “Think!” banners streaming in the breeze!  It would be fascinating to see how they make these patents actually result in cash flow. Who knows, IBM may have the biggest patent picket fence in the universe?!

I caught myself writing like a patent lawyer today. It was a little unnerving.

In the instant example … blah blah … the preferred embodiment … blahty blah blah … a plurality of moieties … blah blah … the said R group … yawn … including, but not limited to …

It is surprising how easy it is to fall into the style of writing that characterizes patent applications.  It is easy to poke fun at our lawyerly brethren for this.  But the stylistic manner and the use of precise vocabulary with elaborate sentence construction is the result of generations of bitter experience in court. A long time ago, lawyers figured out that you have to say precisely what you mean to get what you want.  

Judges and juries have to arrive at conclusions based on something, so if your fate rests on their interpretation of ambiguous language, you may be in for disappointment.  Precise language is meant to prevent misunderstanding and place rewards and liabilities where they belong.

For chemists who are busy inventing things, it is useful to actually study the form and the language in a handful of patents.  This will give a sense of how intellectual property is actually staked out and claimed.  It is useful for the chemist to provide some guidance to the attorney in drafting claims and maximizing the value of the patent.

I deleted the “plurality of moieties” in the final draft. Just couldn’t do it.

The website Latepatents.net has collated a top 100 list of companies with a link to their individual expired US patents.  Said patents have expired due to failure to pay maintenance fees and not due to normal expiry. I checked a random sampling at the USPTO and found that indeed the patents were expired.

Readers will have to determine for themselves the value of these heaps of company treasure lying about the Public Domain landscape like so many abandoned Buicks, tanks still full of gas.

Given the quality of the companies that have the prematurely expired patents, and the resources they surely spend on IP management, I’ll hazard a guess that most of these patents were allowed to expire on purpose.

Patents are obtained for many reasons. One invention might lead to prompt and exclusive sales and profits for its owner. Another invention might lead to possible cash flow in the future if certain circumstances align properly. Some patents may be intended to be put up for lease or sale. Still other inventions serve to block competitors from facile entry into your line of business, so called “picket fence” patents.

It is not unusual for a given bit of intellectual property to become obsolete before the natural expiration of the patent. Technology can advance sufficiently such that a process or composition is no longer competitive. A company can move away from a technology package for business reasons having nothing to do with the suitability of the patented art.

Finally, I think that some patents are obtained simply because the company has a “policy” that requires the disclosure of inventions and subsequent mechanical submission to the attorneys. If you are a hammer, everything looks like a nail. If you’re running an intellectual property office, every disclosure looks like a patent. 

If too many “improvements” turn into applications, it may not be the fault of over-eager patent attorneys. More likely, it is the result of choices made by company management. I have witnessed a few circumstances where managers have been reluctant to exercise business judgement and have heaped the decision to patent solely upon the hapless attorney. What choice does the attorney have but to prosecute the patent?

It is my opinion that business people far too frequently allow their attorneys to make IP business decisions for them. The typical excuse is that it is a “legal matter”. The question for a business person is this- Can we make a choice that prevents the issue from becoming a legal matter?  Sometimes we use lawyers because we need a surrogate to do the dirty work for us.

The common default choice found in IP is that if it can be patented it should be patented. This is an expensive and weak-minded philosophy and I’ll wager that the patents in the aforementioned list are expired as a result of some second thoughts on the value of these inventions.

The Google Patent Search tool seems to be rather useful for some kinds of patent search activity. I had been using SciFinder or other search tools to find patent numbers that I would then enter into pat2pdf.org to get a single download file copy of the patent. The reason for going to pat2pdf was that it would combine the individual pages of the patent  from the USPTO and download a single combined pdf document of the patent. The Google search tool does this and more.

Our patent office seems to have failed to catch on to the fact that users would prefer not to download patents 1 page per file. Maybe the USPTO has changed this recently or has an upgrade in process. I don’t know.

Among the nice features, it provides links to citation and reference patents. It also provides links to the US classification designations listed in the patent. The default page seems to include the claims and with the click of a button the user can pull up the description or abstract. It also provides a link to download a pdf of the patent or a direct link to the USPTO.  A person can scan a patent without having to download a pdf.

I would say that Google has a handy search tool for at least fairly superficial work.

The USPTO is proposing changes in the rules related to the practice of writing “Markush” claims. Markush claims are used heavily in chemical patent applications and allow applicants to claim vast arrays of chemical species by way of composition of matter or by association with a claimed process. The Markush claim makes use of generic formulae that represent the substance of interest as well as a class of equivalent entities.  It is not difficult to specify features of a simple formula that claim many hundreds or thousands of chemical species. 

The PTO admits that it is overwhelmed with the workload associated with these large collections of substances.  I have no doubt that this is true. Patent prosecution requires a search of the prior art for the novelty requirement. A Markush space filled with a large number of compounds slows down the workflow.  

I would hope that the congress and the PTO consider the cost to the public in performing due diligence as well.  I wonder if our cheminformatics friends can find a way to map the space defined by a Markush claim. This would make a due diligence exercise more cost effective and reliable.

I suppose most of us have not considered what kind of training patent examiners complete before they are cut loose on our applications.  The USPTO provides a lengthy training period for beginning examiners.  The program seems to be quite substantial both in terms of knowledge of the MPEP and case law. 

For some interesting reading it is worth visiting the blog Patently Academic.  This site operated by “Relativity”, which can only be homage to the architect of the Theory of Relativity and former Swiss patent examiner, Albert Einstein.

While tunneling deep through the compacted patent strata, I happened to notice that E. J. Corey’s oxazaborolidine patent appears to be expired.  US Patent 4,943,635 (July 24, 1990) was assigned to the President and Fellows of Harvard College and listed Professor Elias J. Corey as inventor.  This is a patent with 30 claims, of which 3 are independent claims.  All of the claims are for composition of matter. 

The description teaches methods of preparation of a variety of oxazaborolidines, with a special emphasis on the preferred embodiment based on proline.  The use of the catalyst for asymmetric reductions is taught in the description as well. 

Curiously, Corey is the only inventor on the patent. Hmmm.  Knowing that he was well into his career by 1988 when the application was filed, I can only guess that he must have been very busy running multiple reactions, doing flash columns, and burning NMR spectra. \

The next oxazaborolidine patent to expire will be the Merck US 5,039,802 (Aug. 13, 1991) patent.  This is a process patent claiming a method for the preparation of the diarylproline system using aryl Grignard addition to a pyrrolo[1,2-c]oxazole-1,3-dione.

Incidentally, I did witness a famous professor actually doing bench chemistry.  A friend and I were wandering around the chemistry building at her alma mater, (The) Ohio State University, in March of 1993 when we happened past the lab of Mel Newman.

There he was, in his 90’s, intently shaking a 2-liter separatory funnel of some dark hellbroth. He was isolating a polyaromatic hydrocarbon that he made.  Newman graciously stopped to talk about his work. Having freshly graduated from a stereochemistry group and a stereochemistry post-doc, I nearly fainted when I met him. It was like meeting Elvis.  Newman passed away a few weeks later.