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Alphapharm Pty Ltd v H Lundbeck A/S

Alphapharm Pty Ltd v H Lundbeck A/S

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Case Copied 24 April 2008 79 min read

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FEDERAL COURT OF AUSTRALIA
Alphapharm Pty Ltd v H Lundbeck A/S [2008] FCA 559
PATENTS – validity – patent for (+)-enantiomer of the racemate, citalopram, and for method of obtaining that enantiomer – patentee also held previous patent for the racemate – both the racemate and the enantiomer, drugs for the treatment of depression – (+)-citalopram claimed to be therapeutically more effective than citalopram – challenge to validity of claim for (+)-citalopram – construction of claim – whether for (+)-enantiomer as an independently existing molecule or whether also for (+)-enantiomer when part of racemate – whether claim for (+)-enantiomer anticipated by patent for citalopram – whether (+)-enantiomer as an independent molecule was obvious – Australian test for obviousness – application of that test to product claims for the (+)-enantiomer, and to method claim for the method of obtaining it – lack of utility – product claim for a dosage that, inter alia, was less than and more than a useful dosage range.
Held: (1) upon its proper construction, product claimed was the independently existing enantiomer; (2) the invention of the independently existing enantiomer was not anticipated by the patent for the racemate; (3) the Australian “matter of routine” test for obviousness, when applied to the invention of the product, equated to the question whether those skilled in the art, as a matter of routine, would have had the goal of obtaining separate enantiomers in the expectation that one would be a desirable drug for the treatment of depression; (4) one of the product claims relating to dosage failed test of utility; (5) on the evidence, neither the (+)-enantiomer nor the method for obtaining it was obvious at the priority date.
PATENTS – extension of term – patent for (+)-enantiomer of the racemate, citalopram, and for method of obtaining that enantiomer – patentee also held previous patent for the racemate – both the racemate and the enantiomer, drugs for the treatment of depression – (+)-citalopram claimed to be therapeutically more effective than citalopram – both Cipramil (goods based on racemic citalopram) and Lexapro (goods based on (+)-citalopram) entered in Australian Register of Therapeutic Goods (ARTG) – application for extension of term of patent for (+)-citalopram – Commissioner of Patents initially granted extension sought – subsequently, following hearing before her delegate, decided to reduce term of extension on ground that “first regulatory approval date” was date when goods Cipramil based on racemate had been entered in ARTG – appeal by patentee – opponent pharmaceutical company contending that no extension at all should have been granted because application for extension had been made outside six month period following date of first inclusion in ARTG of goods containing the (+)-enantiomer, namely, Cipramil, of which the active pharmaceutical substance was the racemate – questions of proper construction of Patents Act 1990 (Cth) ss 70, 71, 77 – whether goods based on racemate “contain” individual enantiomer – meaning of “first regulatory approval date” in s 70(5) of Act.
Held: (1) Cipramil contained pharmaceutical…

Grounds of appeal

[14] The appellant contends that the primary judge erred in finding that the respondent had discharged the onus of establishing the matters required under the relevant provision.

[15] It was submitted that his Honour failed to give adequate weight to the evidence of the second witness, and that the findings of fact were not reasonably open on the material before the Court.

[16] The respondent, for its part, submits that no error is disclosed, and that the conclusions reached were well within the range of outcomes available to the primary judge.

Consideration

[17] It is convenient to deal first with the question of construction, as the resolution of that issue informs the remaining grounds advanced by the appellant.

[18] For the reasons that follow, we are of the view that the appeal should be allowed in part and the matter remitted for further determination.

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Details

Case: [2008] FCA 559
Decision Date: 24 April 2008

CaseChat Overview and Summary

Alphapharm Pty Ltd initiated proceedings against H Lundbeck A/S regarding the validity and infringement of a patent for a compound used in the treatment of Major Depressive Disorder. The case was heard by Lindgren J in the Federal Court of Australia. The central dispute revolved around the patentability and infringement of a selective serotonin reuptake inhibitor (SSRI) known as citalopram. Specifically, the case addressed whether the patent claimed both enantiomers of citalopram or only one specific enantiomer, and whether H Lundbeck A/S's product, which contained a mixture of both enantiomers, infringed on Alphapharm's patent rights.

The court needed to determine the scope of the patent claims and whether the patent was valid. Key issues included the interpretation of the patent claims, the distinction between the two enantiomers of citalopram, and the legal implications of patenting a mixture of enantiomers versus a single enantiomer. Additionally, the court had to decide if H Lundbeck A/S's product fell within the scope of Alphapharm's patent claims, thereby constituting infringement.

The court held that the patent claims were ambiguous and could be interpreted to cover either both enantiomers or a single enantiomer of citalopram. However, the court concluded that the patent was valid and that H Lundbeck A/S's product, which contained a mixture of both enantiomers, infringed on Alphapharm's patent. The court reasoned that the patent's claims were broad enough to encompass the mixture of enantiomers. Consequently, Lindgren J found in favour of Alphapharm Pty Ltd, declaring the patent valid and ordering H Lundbeck A/S to cease infringement. The case was stood over for further orders, including the determination of costs.

In conclusion, the Federal Court of Australia ruled that Alphapharm Pty Ltd's patent for citalopram was valid, and H Lundbeck A/S's product infringed on these patent rights. The case was adjourned for the parties to agree on the final orders, including costs.

Orders

Orders of the court

1. The proceeding be stood over to Friday 9 May 2008 at 9:30am for the making of orders, including orders as to costs.

2. The parties attempt to agree on the orders to be made.

3. If the parties agree on the orders to be made, they supply a copy of those orders to the Associate to Lindgren J by Monday 5 May 2008.

4. If the parties fail to agree on the orders to be made, they serve (with a copy to the Associate to Lindgren J), by Monday 5 May 2008, the forms of the orders they respectively propose and submissions in support.

Background

Background to the litigation

Both Professors Banwell and Davies are highly qualified in the area of organic chemistry. I discuss their qualifications and experience further at Section E [207] ff. General chemical background In order to understand the issues in these proceedings, it is necessary to have some understanding of organic chemistry. The following outline is based on the affidavit evidence of Professors Banwell and Davies and on the text, Morrison and Boyd, Organic Chemistry, published by Allyn and Bacon (Morrison and Boyd), to which they referred. At the priority date of 14 June 1988, the 5th edition of this text, published in 1987, was a standard text for students and organic chemists. It would be tedious for every phrase or sentence that I quote to be placed within quotation marks and for distinctions to be made between quotation and paraphrase. I acknowledge, however, my quotation from, and otherwise my reliance on, paras 16 to 56 of Professor Banwell’s affidavit sworn 11 August 2006, Annexure 1 to Professor Davies’s affidavit sworn 4 April 2007, and Chapters 1 and 4 of Morrison and Boyd. Atoms and molecules Organic chemistry is a specialised branch of chemistry dedicated to the study of molecules that contain carbon atoms. Atoms are the building blocks of all matter. They are composed of three types of particles: protons, which carry a positive (+1) charge; neutrons, which carry no charge; and electrons, which carry a negative (–1) charge. Protons and neutrons are held together by very strong forces and constitute the “nucleus” of an atom. Electrons orbit the nucleus at different levels. The chemical elements, such as carbon, hydrogen and oxygen, are particular types of atoms. Each element has a unique number of protons, which, if the element is uncharged, is equal to its number of electrons. Some elements have a more stable number of electrons than other elements. Stability is achieved by filling orbitals known as electron shells. The first electron shell requires two electrons. The second and third each require eight electrons. The greatest stability is reached when the outermost electron shell for the particular element is full. Elements interact with each other in order to achieve a stable number of electrons either by gaining, losing or sharing electrons. Molecules are combinations of atoms. They are described by molecular formulae which utilise chemical symbols for each element followed by numeric subscripts for the number of atoms of that element in the molecule. For example, a molecule of water is shown as H2O to signify that the molecule comprises two atoms of hydrogen (H) and one of oxygen (O). Citalopram comprises the elements hydrogen, oxygen, carbon (C), fluorine (F) and nitrogen (N). In complicated molecules, groups of atoms with a specific function are called functional groups. An example in this case is the hydroxyl group (OH). Atoms are held together in molecules by electron sharing, in a process called covalent bonding. A covalent bond refers to the sharing of two electrons between two atoms, so that both electrons fall within the outer shell of each atom. Most elements need to share a certain number of electrons to be stable. For example, in order to achieve stability, hydrogen, which has one electron and needs to fill the first electron shell (which has a capacity of two electrons), forms one covalent bond; carbon, which has six electrons and needs to fill both the first electron shell and the second electron shell (which has a capacity of eight electrons), forms four covalent bonds; and chlorine (Cl), which has seventeen electrons and needs to fill the first, second and third electron shells, forms one covalent bond. When an atom of hydrogen reacts with an atom of chlorine, they share one electron with each other to make a covalent bond. Once this happens, both atoms have a stable number of electrons and a molecule of hydrogen chloride is the result. Pictorially, a hydrogen chloride molecule (HCl) is represented by a line joining the two atoms to indicate a covalent bond (H–Cl).

Evidence

Evidence Before The Court

Full text does not contain this section.

Decision

Reasons for decision

LINDGREN J

In my opinion, for the reasons given above, s 60 of the Evidence Act defeats the Factual Basis Objection. I would have declined to make an order under s 136 of that Act if the passages objected to had not succumbed to the General Relevance Objection.SECTION O – CONCLUSION As the parties requested, I will publish these reasons and give them an opportunity to make submissions as to the orders (including orders as to costs) to be made. The four proceedings will be fixed for a date for the making of such orders. Directions will be made for the filing and service of submissions as necessary. While the reasons set out above were being proofread in preparation for delivery of judgment, the English Court of Appeal on 10 April 2008 gave judgment in H Lundbeck A/S v Generics (UK) Ltd [2008] EWCA Civ 311, the appeal from the judgment of Kitchin J in Generics v Lundbeck previously noted. With respect, I do not think it necessary to incorporate references to their Lordships’ reasons, which are, generally speaking, consistent with what I have written above.

Ratio Decidendi

Legal Principle Established

Established by: LINDGREN J

The second way of describing enantiomers is an abstract theoretical description (as distinct from requiring physical testing) and provides an absolute configuration. Enantiomers are designated R or S on the basis of the direction of rotation when the molecule is abstractly positioned according to certain standard rules (the Cahn Ingold Prelog (CIP) rules). The rules are based on the atomic number (number of protons) of each atom or functional group connected to the chiral centre. First, each atom or functional group is labelled 1 to 4, with 1 indicating the highest atomic number and 4 indicating the lowest atomic number. Second, the molecule is visualised so that the atom or group labelled 1 (and so having the lowest atomic number) is directed into the page. Third, a curved arrow is drawn from the 1 position to the 2 position and then to the 3 position, and from the 3 position to the 4 position. If the arrow points clockwise, the configuration is designated R (Latin: rectus, right); if it points anticlockwise, the configuration is designated S (Latin: sinister, left). Diagram III below shows the two enantiomers of bromochlorofluoromethane, reoriented so that the atom with the lowest atomic number (H) is facing away from the page. The enantiomers are designated R and S based on the descending priority of the other three elements.Diagram III – 3D structure and R and S designations of two enantiomers (7 and 8)of bromochlorofluoromethane It is common ground that in 1988, an ordinary skilled but non-inventive chemist, being given a 2D structural formula with a single chiral centre, could, by applying the CIP rules, have drawn the absolute configuration of each of the two enantiomers, R and S.Application to citalopram The following is the 2D structural formula of citalopram:Diagram IV – 2D structural formula of citalopramThis formula uses a convention for organic molecules where carbon and hydrogen molecules are not identified by symbols. For example, each of the lines surrounding the N (nitrogen) on the right side of the structure represents a bond to a carbon atom, which is itself bonded to two or three hydrogen atoms. The hydrogen atoms never appear in such formulae. Because each carbon atom must have four covalent bonds, bonds to hydrogen atoms are inferred if a junction has less than four bonds emanating from it. The hexagon ‘rings’ contain carbon atoms at each junction. Double bonds between carbon atoms are indicated by double lines and single bonds by single lines. The carbon atoms at each junction are also bonded either to another carbon atom (indicated by a bond ending in a junction), a fluorine atom (indicated by – F) or a hydrogen (not represented by symbol). It is not in dispute that, based on the principles referred to above, including the CIP rules, a chemist could, at the priority date, identify from the formula in Diagram IV:·four different chemical groups attached to a common carbon (the carbon being, by definition, a centre of chirality); and·the R and S enantiomers of the compound.Furthermore, a chemist could, at the priority date, depict the R and S enantiomers of citalopram, but not which of them would be the (+)-enantiomer and (-)-enantiomer. There is no fixed relationship between the R and S dichotomy and the (+) and (-) dichotomy. It is only as a result of testing with plane-polarised light that one can know which of the R and S enantiomers is the (+)-enantiomer and which is the (-)-enantiomer.Major Depressive Disorder and selective serotonin reuptake inhibitors