Pharmaceutical Chemistry Patent Blog

In re Ochiai, 72 F.3d 1565 (Fed. Cir. 1995).

Facts:

Ochiai filed a patent application directed to cephem compounds and a process for preparing them. Both the starting material and the product were novel and nonobvious although the process involved and an amine used in the claimed process were otherwise known and unpatentable. The examiner rejected the claim as obvious in light of six cited references which demonstrated that the same acylation process had previously been performed using the same amine starting material.

Holding:

The test for obviousness “requires that one compare the claim’s “subject matter as a whole” with the prior art “to which said subject matter pertains.”” The Court reversed the obviousness rejection, holding that it would not have been obvious to choose the reagent because the reagent was unknown and nonobvious.

“[T]he examiner discussed no references containing any suggestion or motivation either (a) to modify known acids to obtain the particular one recited in claim 6, or (b) to obtain the particular new and nonobvious cephem produced by the process of claim 6. In short, the prior art contains nothing at all to support the conclusion that the particular process recited in claim 6 is obvious.”

The court cited In re Dillon, stating that “[w]hen any applicant properly presents and argues suitable method claims, they should be examined in light of all . . . relevant factors, free from any presumed controlling effect of Durden” or any other precedent.

Rule: A process claim is not prima facie obvious if the starting material and product are novel and nonobvious.

Disposition: Reversed.

See Apfel v. Prudential-Bache Sec., Inc. for another case involving the patenting of investment related business methods.

Facts:

Signature Financial Group obtained a patent entitled “Data Processing System for Hub and Spoke Financial Services Configuration”. The invention involved a computer program in connection with a system in which mutual funds (“spokes”) pooled their assets in an investment portfolio (“hub”) that was organized as a partnership. The system managed the daily allocation of assets for mutual funds with investments in the same portfolio and made daily determinations of the true assets held by each fund. State Street made an unsuccessful attempt to obtain a license and subsequently brought a declaratory judgment action asserting that the patent was invalid because it was not patentable subject matter under 35 USC 101. The district court found that the patent was invalid and granted summary judgment in favor of State Street.

Issue: Is a machine or program that stores and calculates numbers in a useful manner eligible for a patent?

Holding:

Yes. A machine or program that stores and calculates numbers in a useful manner is patentable subject matter. The patent claim at issue was directed to a data processing system and recited each element as a means plus function. The court, citing In re Allapat, held that “”machine” claims having “means” clauses may only be reasonably viewed as process claims if there is no supporting structure in the written description that corresponds to the claimed “means” elements.” The court held that the claim was not invalid for lack of patentable subject matter because machines are patentable under 35 USC 101. The court also noted that the question of whether the claim was directed to a machine or a process was irrelevant because both are patentable subject matter.

The district court had also found the claim invalid because it fell within two judicially created exceptions to statutory subject matter. The district court held that the claimed subject matter fell within the “mathematical algorithm” exception and the “business method” exception. The Federal Circuit rejected these arguments. Citing Diamond v. Chakrabarty and Diamond v. Diehr, the court stated that Congress intended 35 USC 101 to extend to “anything under the sun that is made by man.”

“Today, we hold that the transformation of data, representing discrete dollar amounts, by a machine through a series of mathematical calculations into a final share price, constitutes a practical application of a mathematical algorithm, formula, or calculation, because it produces “a useful, concrete and tangible result”–a final share price momentarily fixed for recording and reporting purposes and even accepted and relied upon by regulatory authorities and in subsequent trades.”

Disposition: Reversed and remanded.

State St. Bank & Trust Co. v. Signature Fin. Group, Inc., 149 F.3d 1368 (Fed. Cir. 1998).

Additional case briefs are available at Lawnix.

In re Dillon, 919 F.2d 688 (Fed. Cir. 1990) (en banc).

Facts:

Diane Dillon filed a patent application entitled “Hydrocarbon Fuel Composition” directed to fuel compositions comprising tetra-orthoester compounds and their use in reducing the emission of soot during combustion. The PTO Board of Patent Appeals and Interferences affirmed the examiner’s rejection of all of the claims of the patent application and Dillon appealed to the Court of Appeals for the Federal Circuit.

The tetra-orthoester compounds were a known class of compounds, but the compounds had not been used in combination with hydrocarbon fuels previously. The soot-reducing properties of the compounds had not been disclosed in the prior art.

The Board rejected all of the claims as obvious in light of two key primary references. One of the references disclosed fuel compositions comprising tri-orthoesters as a dewatering agent. The other reference disclosed the use of tri-orthoesters in fuel compositions to prevent the phase separation of alcohol and fuel. The references did not address tetra-orthoesters. The Board also cited references that disclosed the use of tri- and tetra-orthoesters in non-hydrocarbon based fuels as dewatering agents.

The Board concluded that the structural similarity between tri- and tetra-orthoesters gave rise to a reasonable expectation that the claimed compounds would have similar properties and that it had been established that the claims were prima facie obvious. Dillon did not present secondary indicia of non-obviousness and the examiner’s rejection was affirmed.

Issue:

The issue was whether a prima facie case of obviousness had been established when the claimed additives were structurally similar to compounds appearing in the prior art with a different disclosed utility, and where the utility disclosed in the application was neither taught nor suggested in the prior art.

Holding:

A prima facie case of obviousness does not require showing both a structural similarity and a suggestion or expectation that the claimed compound will have the same or similar properties as those disclosed in the application.

The court held that “structural similarity between claimed and prior art subject matter, proved by combining references or otherwise, where the prior art gives reason or motivation to make the claimed compositions, creates a prima facie case of obviousness, and that the burden (and opportunity) then falls on an applicant to rebut that prima facie case. Such rebuttal or argument can consist of a comparison of test data showing that the claimed compositions possess unexpectedly improved properties or properties that the prior art does not have, that the prior art is so deficient that there is no motivation to make what might otherwise appear to be obvious changes, or any other argument or presentation of evidence that is pertinent. There is no question that all evidence of the properties of the claimed compositions and the prior art must be considered in determining the ultimate question of patentability, but it is also clear that the discovery that a claimed composition possesses a property not disclosed for the prior art subject matter, does not by itself defeat a prima facie case. Each situation must be considered on its own facts, but it is not necessary in order to establish a prima facie case of obviousness that both a structural similarity between a claimed and prior art compound (or a key component of a composition) be shown and that there be a suggestion in or expectation from the prior art that the claimed compound or composition will have the same or a similar utility as one newly discovered by applicant.”

Disposition: Affirmed.

In re Diane M. Dillon

An ether is a functional group characterized by an oxygen atom attached on each side to an alkyl, alkenyl, alkynyl, or aryl group. The reactivity and properties of dialkyl ethers are significantly different from those that contain one or more alkenyl, alkynyl, or aryl groups.

Nomenclature

Ethers commonly are named using the formula “alkoxyalkane” in which the alkoxy and alkane components of the name are derived from the alkyl groups attached to the ether oxygen. An alkyl chain attached to an oxygen atom can also be referred to as an alkoxy substituent when the group acts as a substituent.

Physical Properties

In general ethers have relatively low polarity. The C-O-C bond angle is approximately 110^o. The individual C-O dipoles are largely opposed and the resulting dipole moment is relatively small compared to other oxygen-containing organic compounds.

Ether moieties are unable to form hydrogen bonds to other ethers. While the oxygen atom of an ether is a good hydrogen bond acceptor, the group is unable to act as a hydrogen bond donor. Ethers are relatively soluble in solvents that are able to act as hydrogen bond donors such as water and lower alcohols; for example, tetrahydrofuran and 1,4-dioxane are totally miscible with water. Ethers are capable of solvating metal ions and can act as ligands in transition metal complexes.

Reactions

Ethers are generally relatively unreactive. As protective groups they are able to withstand a wider range of conditions than esters or other common alcohol protective groups. Their relative stability often makes their removal more difficult however. Ethers undergo the following reactions:

• Nucleophilic displacement

Strained ethers such as epoxides (three membered ring cyclic ethers) are far more susceptible to fragmentation by nucleophiles, generally with retention of configuration. Displacement can occur under both basic and acidic conditions.

• Peroxide formation

Primary and secondary ethers can form peroxides in the presence of oxygen. These compounds are highly explosive and become concentrated when the solvent is evaporated. It is therefore important to handle ethereal solvents carefully and to avoid evaporating ether solvents to dryness and, if possible, to handle them under an inert atmosphere.

• Hydrolysis

Ethers typically are hydrolyzed with relatively strong Lewis acids such as boron tribromide or heating in hydrobromic acid. Hydrolysis will occur slowly upon treatment with lower halogen mineral acids such as hydrochloric acid. Ethers react with hydrobromic acid and hydroiodic acid at a higher rate. Certain aryl ethers can undergo cleavage under relatively milder conditions, such as treatment with aluminum trichloride.

• Reduction to alkene

Epoxides can undergo deoxygenation to the corresponding alkene via treatment with tungsten hexachloride. The reaction generally proceeds with retention of configuration.

Synthesis

Ethers can be prepared in the laboratory in several different ways.

• Williamson Ether Synthesis

R-O- + R-X → R-O-R + X-

This reaction involves the nucleophilic displacement of a halide ion from an alkyl halide with an alkoxide. An alkoxide is treated with a compound possession a good leaving group that is susceptible to nucleophilic displacement. Suitable leaving groups (X) include sulfonates, bromides, and iodides. The reaction proceeds in competition with elimination and can therefore give a mixture of substitution and elimination products. The Finkelstein Reaction is commonly employed to prepare alkyl iodide compounds for use in the Williamson Ether synthesis from the corresponding chlorides and bromides.

Reactions in which the leaving group resides on a benzylic carbon atom are particularly facile because the positive charge on the carbon atom bearing the leaving group in the transition state is stabilized by conjugation with the phenyl ring.

• Electrophilic addition of alcohols to alkenes

This reaction proceeds under Lewis acidic conditions. Mercury trifluoroacetate frequently is used as a Lewis acid catalyst. The resulting ether proceeds via anti addition and affords the ether possessing Markovnikov regiochemistry.

Epoxides (three membered ring cyclic ethers) can be prepared by the following methods:

• By the base-promoted intramolecular displacement of a good leaving group (e.g. halogen, OTs) by a hydroxyl moiety on a carbon atom adjacent to the leaving group.
• MCPBA oxidation of an alkene (affords syn addition product).

Lear, Inc. v. Adkins, 395 U.S. 653 (1969).

Facts:

Lear hired Adkins as an engineer, agreeing that Adkins would retain ownership of any inventions he developed. The agreement also provided that Adkins would license his inventions to Lear.

Adkins filed a patent application directed to an improvement he developed. Lear and Adkins entered into a licensing agreement that provided that if no patent issued or any issued patent were subsequently held to be invalid, Lear would be able to terminate the agreement. See American Machine & Metals v. De Bothezat Impeller.

During prosecution, Lear claimed that a reference uncovered during a search by the USPTO anticipated fully Adkins’ invention. Lear subsequently ceased paying the full amount of royalties due under the agreement.

Upon issue of the patent, Adkins brought suit against Lear for breach of the licensing agreement. The trial judge held that Lear was estopped by its licensing agreement from arguing that the patent was invalid as a defense to infringement. On appeal, the California Supreme Court held that the licensing agreement was still in effect, that Lear did not have the right to cease paying royalties, and that Lear was estopped from challenging the validity of the patent.

Holding:

The court overruled the holding of Automatic Radio Manufacturing Co. v. Hazeltine Research, Inc., 339 U. S. 827, 339 U. S. 836 which had held that a licensee was estopped from challenging the validity of a patent. The licensee is not estopped from challenging the validity of a patent and is not obligated to continue to make royalty payments after the date of issue of the patent if it can prove that the patent is invalid. Whether Lear was obligated to pay royalties under the agreement for the period prior to issue of the patent was left as a matter of state law.

The Claisen Condensation is an important carbon-carbon bond forming reaction that produces a 1,3-dicarbonyl compound from an ester and another carbonyl compound. The intramolecular variant of the reaction is known as the Dieckmann Condensation. The reaction is performed under basic conditions, usually using the alkoxide form of the alcohol component of the ester to avoid transesterification.

The reaction usually involves the reaction of two molecules of the same ester to avoid forming a mixture of different condensation products. An ester and a different carbonyl compound can be used however, particularly when the ester does not possess an enolizable hydrogen atom α to the carbonyl. This variant is known as the Crossed Claisen Condensation.

The mechanism involves formation of the enolate of the compound that will react with the ester as a nucleophile. The enolate is formed via deprotonation of a hydrogen atom α to the carbonyl. The enolate then attacks the carbonyl carbon of the ester, and the tetrahedral intermediate undergoes elimination of alkoxide.

The driving force of the reaction is the deprotonation of the resulting 1,3-dicarbonyl compound condensation product. Hydrogen atoms that are α to two carbonyl carbon atoms are significantly more acidic than either the alcohol or the starting materials and essentially all of the 1,3-dicarbonyl product will be deprotonated in solution. For example, the pKa of ethyl acetoacetate (shown above) is 11, whereas the pKa of ethanol is 16.

The Claisen Condensation differs from the Aldol Condensation because the Aldol Condensation forms an intermediate β-hydroxy carbonyl compound which undergoes elimination to form an α,β-unsaturated carbonyl compound. In the Claisen Condensation however, the resulting tetrahedral intermediate is a hemiketal which can eliminate alkoxide to form the ketone.

In re Hall, 781 F.2d 897 (Fed. Cir. 1986).

Facts:

The examiner rejected the claims of Hall’s reissue application on the grounds that they were anticipated under 35 USC 102(b) by a doctoral thesis in a university library in the Federal Republic of Germany that was made available to the public more than one year prior to the critical date. The examiner’s rejection was sustained on appeal to the Board of Patent Appeals and Interferences.

The director and manager of the university library loan department had made a statement that approximated the date the thesis would have been available to the public based on the library’s procedures for processing doctoral theses. The estimated date was over two months prior to the critical date. He also stated that theses were made available to the public by indexing in a dissertations catalog and placement in a dissertations section within the general stacks.

Issues:

1) Can the date the thesis was made accessible to the public be established based on a statement regarding the general practice of the library regarding the processing of theses, without specific evidence regarding the thesis itself?

2) Does a single thesis cataloged in a university library constitute sufficient accessibility to those interested in the art exercising reasonable diligence?

Holding:

1) Yes. Competent evidence of general practice can be used to establish the date the thesis became available to the public.

2) Yes. “The Sec. 102 publication bar is a legal determination based on underlying fact issues, and therefore must be approached on a case-by-case basis.” Under these facts, a copy of a thesis indexed and available to the public is a “printed publication” under 35 USC 102(b).

Disposition: Affirmed.

Further information:

In re Leo M. HALL

In re Gosteli, 872 F.2d 1008 (Fed. Cir. 1989).

Facts:

Gosteli filed a patent application with claims directed to Markush groups and dependent claims disclosing specific compounds used in the synthesis of antibiotics. The examiner rejected the claims under 102(e) as anticipated by two compounds disclosed but not claimed in United States Patent No. 4,155,912 by Menard.

Gosteli claimed the benefit of the foreign priority date of a patent application filed in Luxembourg that disclosed the two compounds of the Menard patent. The Menard patent would not have been an effective reference under 102(e) if Gosteli were entitled to the priority date of the Luxembourg patent application.

On appeal to the Board of Patent Appeals and Interferences, the Board upheld the examiner’s rejection and denied Gosteli the benefit of the filing date of the Luxembourg patent application. The Board reasoned that because the claims at issue contained additional subject matter not disclosed in the Luxembourg patent application, the claims in the US patent application were not the “same invention” as required under 35 USC 112. The court held that the effective priority date was the filing date of the US patent application because the Luxembourg application did not provide a written description of the entire scope of the claims at issue.

Issues:

1) Are patent claims entitled to the benefit of their foreign priority date only if the foreign patent application provides adequate support for the entire scope of the claims as required under 35 USC 112?

2) May an applicant use a reduction to practice outside the US to swear behind a prior art reference under 37 CFR 1.131(a)?

Holding:

1) Yes. The priority date of the earlier filed foreign application is available only if the foreign application provides adequate support for the claims in the US patent application.

2) No. An applicant may only use activity within the United States as a basis for swearing behind a prior art reference under 37 CFR 1.131(a).

Disposition: Affirmed.

Markman v. Westview Instruments, Inc., 517 U.S. 370 (1996).

Facts:

Markman obtained a patent for a system of monitoring clothes through the dry-cleaning process. The system included generating and attaching a bar code that could be read by optical detectors to each item of clothing. According to the claim at issue, the invention can “maintain an inventory level” and “detect and localize spurious additions to inventory.” The jury heard an expert witness testify regarding the claim’s meaning and found that Westview had infringed Markman’s patent. The trial court nevertheless entered a directed verdict for Westview, stating that the accused device did not track inventory within the meaning of Markman’s claim. The Court of Appeals affirmed and held that claim interpretation is a matter of law and therefore a matter to be decided by the court and not the jury.

Issue: Is claim interpretation a matter of fact to be decided by the finder of fact, or a matter of law to be decided by the court?

Holding:

Claim construction is a matter of law to be decided by the court. The Seventh Amendment right to trial by jury is to be defined according the right under English common law when the Amendment was adopted. The court held that infringement cases at common law were decided by juries. Terms in the specifications however were interpreted by the judge. This case has led to the practice of holding “Markman hearings” in which the court will hear testimony and receive evidence prior to trial in order to determine interpret the scope of the claims at issue.

Disposition: Affirmed

Argued: January 8, 1996

Decided: April 23, 1996

Majority by: Souter

Joined by: Unanimous

The Aldol Condensation is one of the most fundamental carbon-carbon-bond forming reactions in organic synthesis. Two carbonyl compounds, each of which may be either an aldehyde or a ketone, undergo a base-promoted condensation to afford an α,β-unsaturated carbonyl compound.

The reaction takes place in two stages. First, the enol form of one of the carbonyl compounds attacks the non-enolized carbonyl carbon atom of the second compound. This results in the formation of a β-hydroxy carbonyl compound. In the second stage, the intermediate tautomerizes to the enol form and a molecule of water is eliminated. This second step is possible only if the first enolizable compound possesses two hydrogen atoms on a carbon adjacent to the carbonyl because it must be able to tautomerize to the enol form twice. If only one such hydrogen atom is present, the reaction can proceed no farther than the β-hydroxy carbonyl compound.