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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 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 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. 

This is a long and drawn out post on intellectual property, possibly not suitable for those with attention deficit disorder.

<<<< Warning! This post may cause somnolence or ED. >>>>

In this post, I have attempted to make a case that current practice in granting US patents contains a flaw that may be counter to the public interest. See what you think.

In my view, there is a curious discontinuity between the practice of determining obviousness and the allowance of Markush claims in US Patent law.  A Markush claim in the context of chemistry refers to a claim of a generic chemical structure defined by symbols that represent sets of functionally related moieties or structures.  Very often a core moiety is defined and one or more substructure symbols or other symbols representing various chemical elements are attached. 

As an example of Markush claims, consider US 4,237,133, an expired Pfizer patent dated December 2, 1980.  I “randomly” found this patent by searching under the key words “bromination” and “aromatics” at the USPTO website. This patent is illustrative of the point I want to make and my use here is not meant to defame or otherwise irritate Pfizer. I have no connection to this art in any sense.

The ‘133 patent is a fairly ordinary chemical patent. It contains 10 claims- two independent claims (claims 1 and 10) and 8 dependent claims that are ultimately based on claim 1.  Claim 1 is a Markush claim that defines a set of chemical compositions that the PTO has allowed the assignee, Pfizer, to have a legal monopoly on.   Basically, Pfizer was allowed two varieties of claims: a) a composition of matter,  and b) the process of producing analgesia in mammals, based on the compounds in claim 1.

Claims 2 through 8 are a series of “necking down” refinements to more preferred embodiments that are especially meaningful to the assignee.  Preferred embodiments are specific features that the assignee apparently wished to have clear definition to avoid ambiguity.

A patent must be “enabling”. That is, the patent must teach enough of the art to allow a Phosita the chance to see and avoid the patented art.  This is the whole purpose of publishing a patent.  If the state is to grant exclusive rights to a composition of matter or a process, then the public needs to have a fair chance to avoid infringement. The content ahead of the claim section is called the specification and it must contain information that, when combined with the claims, enable a reader to understand exactly what is being claimed and under what constraints.  In the case of composition of matter, it is common to disclose the procedures used to make the composition so there is no doubt by Phosita as to what conditions lead to the claimed material.

The patent claims a tricyclic ring systen festooned with functionalities, some of which are variable.  Variable groups are R1, R2, R3, R4, Z, and W.  R1 is further subdivided into other moieties, some bearing variable groups R’ and R” and appended to a chain bearing p methylene units -(CH2)-, where p may range from 0 to 4 .  Z and W are also comprised of features subject to variability.

The point is that the set of all claimed species is quite large.  Not surprisingly, one could easily wander into claimed composition space because, ordinarily, CAS does not capture all of the compositions from the Markush claim.

It is not required that the applicant prove that they have prepared each permutation in the set of claims, nor is it required that the enabling procedures specifically address each claimed species. The ‘133 patent has 43 procedures, many of which are for intermediate compounds, at best a number that falls far short of the entire set of claimed compositions.  Usually, it is sufficient for illustrative examples or preferred embodiments to be set forth in procedure.

If you think of each group as a spatial dimension, a generic core species with n variable groups essentially maps out a set of structures occupying a kind of n-dimensional space, subject to specific exclusions. When the variable groups are defined as alkyl, aryl, alkoxy, alkenyl, etc., the number of claimed species can be quite large due to the vast number of possible combinations of groups.  Even limited ranges, i.e., R = C20 alkyl, etc., can result in huge collections of claimed species owing to structural isomerism. 

The concept of obviousness in patent prosecution is one of the most vexing and mercurial ideas I can think of.  The code is set forth in 35 USC 103.  A patent attorney will caution that there is no hard and fast universal definition in advance of litigation because what really matters is how a judge decides the matter.  In a practical sense, though, obviousness depends on how the examiners interpret the code.

On to the point of this posting.  While it is possible for an applicant to claim compositions never made or compositions that should exist by reasonable extrapolation, claims in the reverse sense are more problematic. But what do I mean?

Consider US 7,235,700, a process patent claiming the preparation of a cyclohexenone functionalized on the beta carbon with an enol ether group.  [Disclaimer: again, this patent was “randomly” chosen. I have no specific axe to grind with the assignees or the inventors.  I do, however, have an axe to grind with US patent law.]

This process is a good piece of journeyman organic synthesis featuring the preparation of an alpha/omega functionalized fragment with a Grignard functional group on one end and a silyl-protected oxygen on the other.  From Example 2 of the ‘700 patent, to the Grignard reagent, made in the customary fashion in diethyl ether with dibromoethane as an entrainment additive, was added a THF solution of the cyclohexenone enol ether.  The Grignard added to the enone in 1,2 fashion to afford a tertiary alcohol which upon acid hydrolysis, the resulting alcohol eliminates and the 3-alkoxy enol ether hydrolyzes to afford the product cyclohexenone on workup. 

The patent teaches that the inventors had a poor process before this patented process (column 1, line 37).  So, this must be an improvement, right? It seems to be. But, should it receive a patent?

From my copy of Kharasch and Reinmuth, I see that 1,2-additions of Grignard reagents to cyclohexenone were reported as early as 1941 (Whitmore, Pedlow JACS, 1941, 63, 758-760).  So the knowledge of 1,2- vs 1,4-additions by RMgX nucleophilic additions to cyclohexenones resulting in primarily 1,2-addition is not new. 

The use of nucleophiles with protected incompatible functional groups is not new.  The hydrolysis of enol ethers is not new.  Indeed, nowhere in the description do the inventors state that the disclosed transformations were “surprising” or “unexpected” in their outcome.  As a phosita myself, I look at this patent and see good solid organic synthesis.  I see the results of workers who have undergone training in the usual graduate level chemistry curriculum. Advanced organic synthesis with attention to donors and acceptors, functional group transformations, and protection/deprotection schemes.  They took known transformations and assembled the pieces into the desired molecule.

My objection is this.  Under the convention that Markush claims are allowed under current practices, many compositions of matter can be claimed by virtue of simple declaration despite the fact that homologous series or the usual genus groups of radicals (alkyl, alkenyl, alkynyl, aryl, heteroaryl, etc.) may be rather obvious additions to the list.  A Phosita would reasonably state that if methyl is feasible, then so is ethyl, propyl, butyl, …, alkyl.  Markush claims invoke a kind of obviousness that is allowed. 

However, the same principle may not apply in reverse. That aspect of the body of scientific work teaching that certain generalizations are possible does not seem to be allowed in determinations of obviousness. 

In the instant example, the generalization is that Grignards as a class might be expected to add in the fashion claimed in the ‘700 patent.  Or that enol ethers as a class would be expected to undergo acid catalyzed hydrolysis to ketones.  In the ‘700 patent, elements of the claim are novel only by virtue of being obscure members of a very large set of possibilities.

So, on the novelty and obviousness side of examination, the fact that a claim uses known transformations or schemes on heretofore unreported substrates bearing known features seems to be sufficient to cause an examiner to allow the claim.  The allowance of Markush claims then allows broad generalization into large sets of claimed structures.

But generalization from a broad area of knowledge may not necessarily bar an unreported claim element when acted upon by known influences resulting in transformations that are consistent with the broad knowledge, as in the case of the ‘700 patent.

A patent lawyer reading this might object that the novelty of the substrate and the lack of specific precedence confers novelty and non-obviousness under current precedent.  That lawyers opinion might be internally consistent with precedent and most would leave it at that. 

But the overarching concern that I want to draw attention to is that the current practice in relation to novelty and obviousness may not serve the public interest. I’m seeing far too many patents being allowed for the application of known transformations to substrates that are merely obscure.  What passes for inventorship is often just good craftsmanship. Reacting a Grignard reagent with a ketone followed by elimination is a general process that we might teach to students in a classroom. 

Indeed, the current practice of teaching chemists is to expose the student to systematic generalizations of reaction-types so that they can go out and put generalizations into practice rather that have to memorize countless specifics. 

When these chemists apply their training by reducing generalizations to practice on specific substrates, however, it seems they can claim to have made an invention under US patent law. 

The upshot is that a good deal of technology resulting from ordinary problem solving skills is barred from the public domain for 20 years.  Not that I believe that privately developed inventions should be in the public domain. But I will point out that it is quite easy for a company to get clobbered by an infringement suit for stumbling into claimed art by practicing what their chemists learned to do in graduate school. Reducing general reactions to practice.

I suspect that it is common practice for companies to believe that if something is patentable, then a patent is manditory.  Unfortunately, the current system seems over-generous in granting 20 year monopolies for dubious inventions. When the threshold for obtaining a patent is too low, when practices are too easily removed from the commons, others trying to practice the art are unreasonably restrained.

Reform of matters as basic as the definition of obviousness and novelty cannot come from the USPTO, the courts, or from patent attorneys. Applicants and their attorneys will continue to game the system to the extent allowed by the courts. Fundamental change must come from legislation.

The chemical business is, after all, a business.  You have to make something that somebody wants. Brilliant ideas are a dime a dozen. Getting a new product to market is harder than you might expect, even if you have a purchase order in hand. The transition from bench to 1000 gallon reactor is often full of unanticipated problems.  The process of forcing a new product or technology on a market that didn’t exactly ask for might be called “Technology Push”.  The process of responding directly to a clear market demand is called “Market Pull”.

Market pull is a force that business types, especially the MBA’s, feel best about.  It is easy to justify the allocation of resources to launch into a product development cycle that addresses a clear and quantifiable demand.  Duh. It’s a no-brainer. That is, if there are no bottlenecks to get through. The merits of market pull are only valid if the proposed technology has been shown to work to specifications. Beware of the inventor who cannot produce a prototype to back his/her patent.

Technology push is a circumstance wherein a company has a product or technology that might stimulate demand if it were marketed properly.  Now, an economist might say that there is no such thing as stimulating demand. They’ll patiently explain that this only stimulates an underlying demand that may not have been articulated. Whatever formalism you prefer, it is possible to dazzle potential customers with a new capability.  Clever people can dream up applications that the original inventors could have never anticipated. Look at Symyx with their fantastic technology package for high throughput experimentation.

It is a bit easier to write a business plan based on market pull because the job of forecasting revenue flows should be based on measurable market conditions. Again, the assumption is that the proposed response to the market pull is a technology that works.

A business plan based on technology push has to incorporate estimates of acceptance of change. You see, technology push is the realm of the paradigm shift.  Predicting outcomes from the early side of the timeline is very tricky.  Customers for paradigm shift technologies may be scarce.  Not all companies are interested in being an early adopter or a buyer of first generation technology. 

Market pull is the domain of orthodoxy, of the rightous and proper company president who is also a CPA and who worked his way up the ladder from the accounts receivable department. Technology push is the domain of the engineers and scientists.  These are the dreamers who know in their hearts that if you build it, they will come.

Successful technology companies are somehow able to give a voice to the technology people in the allocation of resources.  Very often, these companies are managed by chemical engineers. While ChemE’s may not be trained in advanced synthesis R&D, they are involved in the scale up and economics of new processes.  Chemists live in a 2-dimensional world of space and time.  Chemical engineers live in the 3-dimensional world of space, time, and money.  Their knowledge of economics is what causes them to rise to the top of the corporate ladder more frequently than chemists.

It seems to me that companies that thrive today are those who do both market pull and technology push. Market pull is the cash cow.  Technology push is the seed corn for next years crop.


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