New Page added under Obviousness:
Obviousness of Chemical Processes
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A “method of making” a compound may be non-obvious if the starting material or final product are themselves non-obvious.
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In re Ohciai has been good law for 20+ years.
Category Archives: Case Law
Cabazitaxel Method Claims Unpatentable
September 21, 2017
MYLAN LABORATORIES LIMITED, (Petitioner)
v.
AVENTIS PHARMA S.A. (Patent Owner)
Case IPR2016-00712
Patent 8,927,592 B2
The PTAB ordered that Sanofi’s (Aventis Pharma S.A.) patent claims to uses of Cabazitaxel have been proved to be unpatentable by a preponderance of the evidence.
Cabazitaxel
4α-acetoxy-2α-benzoyloxy-5β, 20-epoxy-lβ-hydroxy-7β, 10β-dimethoxy-9-oxo-ll-taxen-13α-yl(2R,3S)-3tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate.
Onglyza® and Kombiglyze® XR (saxagliptin) Patent Survives Challenge from Mylan
September 12, 2017
Mylan and other generic manufacturers petitioned the Patent Trial and Appeal Board (PTAB) to institute an inter partes review of AstraZeneca’s patent claiming compositions including saxagliptin. AstraZeneca markets saxagliptin as Onglyza® and Kombiglyze® XR for diabetes.
Case IPR2015-01340 / Patent RE44,186 E
The PTAB’s Administrative Patent Judges (APJ) decided that the petitioners did not show with preponderance of the evidence that the claims of Reissue RE44,186 of U.S. Patent No. 6,395,767 would have been obvious to a skilled artisan. Particularly, saxagliptin was not obvious over “compound 25.”
Saxagliptin:
Saxagliptin Structure
Prior art: “Compound 25”
Structure of “Compound-25”
State of the Art:
Experienced medicinal chemists (Persons of Ordinary Skill in the Art [PHOSITA]) knew saxagliptin bound to DP 4. But they did not have detailed knowledge of DP 4’s active site for guidance in designing inhibitors because DP 4’s crystalline structure was unknown. At the time of invention, knowledge of DP 4’s binding requirements came from structure-activity relationship (“SAR”) studies.
Lead Compound Analysis:
Petitioners cited a publication by Ashworth containing Compound-25, which they argued would have been selected as a lead compound. (Ashworth et al., 2-“Cyanopyrrolidides as Potent, Stable Inhibitors of Dipeptidyl Peptidase IV,” 6(10) Bioorganic &Med. Chem. Lett., 1163–66 (1996)).
“Compound-25” would not have been selected as a lead compound
The PTAB reasoned that a medicinal chemist would not have selected compound 25 as a lead compound because, among other reasons, (i) Compound 25 was only one of several other similar compounds (ii) Compound 25 only had in vitro data obtained using non-physiological conditions, (ii) there were two much more advanced compounds in clinical trials (i.e., NVP-DPP728 & P32/98) and (iii) Ashworth’s subsequent publication focused on different series of compounds.
Clinical Compounds NVP-DPP728 & P32/98
The PTAB’s analysis could have ended there. But even accepting Petitioners’ assertion that a skilled artisan would have chosen compound 25 as a lead compound, the PTAB determined that the Petitioners didn’t demonstrate that a skilled artisan would have had reason to modify compound 25 with a reasonable expectation of success to arrive at the claimed saxagliptin.
Check out PatentDocs’s Post for further discussion:
http://www.patentdocs.org/2017/09/mylan-pharm-v-astrazeneca-ab-ptab-2017.html
Velcade® Patent Validated by CAFC
August 8, 2017
Millennium Pharmaceuticals, Inc. v. Sandoz Inc. (Fed. Cir. 2017)
A Court of Appeals for the Federal Circuit (CAFC) panel reversed the district court’s holding that Millennium’s licensed patent, U.S. Patent No. 6,713,446 (“the ‘446 Patent”) was invalid for being obvious. The ‘446 Patent claimed a lyophilized mannitol ester prodrug of Bortezomib (See Claim 20). Claim 20 was not obvious according to the panel because, among other reasons, the inventors unexpectedly “discovered that the reason for the dramatic improvement in dissolution and stability for this formulation was the formation of a new chemical compound during lyophilization: the claimed ester of bortezomib and mannitol.”
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Claim 20: The lyophilized compound D-mannitol N-(2-pyrazine)carbonyl-L-phenylalanine-L-leucine boronate.
Earlier, the district court concluded that the new compound was obvious reasoning that Bortezomib was already known (U.S. Patent No. 5,780,454), Lyophilization is already known known, and that the claimed compound is “the inherent result of an allegedly obvious process” of lyophilizing bortezomib and mannitol together.
- There was no evidence that anyone “foresaw, or expected, or would have intended, the reaction between bortezomib and mannitol, or that the resulting ester would have the long-sought properties and advantages”
- “The district court did not find that the prior art taught or suggested that the claimed new compound would be formed, or taught or suggested making the claimed new compound by any method, or taught or suggested that this new compound would have the properties of stability, solubility, and dissociability that it exhibited.”
- “No reference taught or suggested reacting bortezomib with mannitol, and no reference hinted that such an esterification reaction might occur during lyophilization.”
- “No reference taught or suggested that the product of such lyophilization would be a new chemical compound that would solve the problems that had inhibited development of bortezomib in oncology.”
IP Watchdog Post by Jay Pattumudi:
http://www.ipwatchdog.com/2017/08/10/inherent-obviousness-motivation-modify-lead-compound-surprising-unexpected-results/id=86661/
Patent Docs Post:
http://www.patentdocs.org/2017/07/millennium-pharmaceuticals-inc-v-sandoz-inc-fed-cir-2017.html
Dilworth IP Post:
http://www.dilworthip.com/nonobviousness-push-back-millennium-pharma-v-sandoz/
VELCADE® Prescribing Information:
http://www.velcade.com/Files/PDFs/VELCADE_PRESCRIBING_INFORMATION.pdf
VELCADE® (bortezomib) Official Website:
http://www.velcade.com/
Canada’s Supreme Court strengthened patent protection for brand-named-drug makers
July 17, 2017
Canada’s Supreme Court strengthened patent protection for brand-named-drug makers.
http://cen.acs.org/articles/95/i28/Canadas-Supreme-Court-boosts-protection.html
Recent Doctrine of Equivalence Case: “Insubstantial Differences” Test May Be More Suitable than a “Function-Way-Result” Test for Chemical Arts.
The Doctrine of Equivalence is alive and well. For the chemical arts, the CAFC recently suggested that the “Insubstantial Differences” test may be more suitable than a “Function-Way-Result” Test.
See Christopher E. Loh’s post for Fitzpatrick, Cella, Harper & Scinto
When is and “and?” When is and “or?”
May 12, 2017 – [Looking back to 2008 case]
“And” Connotes Alternatives in Topiramate Litigation
When is and “and?” When is and “or?” That sounds silly. But reading Chisum on Patents in the law library reminded me of one of the holdings in the topiramate litigation of Ortho-McNeil v. Mylan, 520 F.3d 1358 (Fed. Cir. 2008), in which the meaning of and was taken seriously. While most dictionary definitions of “and” are additive, dictionary definitions also show use of “and” to “connote alternatives.”
In the Ortho-McNeil v. Mylan case, the Court of Appeals of the Federal Circuit (CAFC) held that the term “and,” in Ortho-McNeil’s claim [US Pat. No. 4,513,006 “Anticonvulsant Sulfamate Derivatives”] was used to connote alternatives rather than in the additive sense.
Ortho-McNeil’s US Pat. No. 4,513,006 claimed a genus of sulfamates covering Topiramate. The disputed clause stated: “R2, R3, R4, and R5 are independently hydrogen or lower alkyl and R2 and R3 and/or R4 and R5 together may be a group of formula (II).” (Emphasis added) [A full copy of claim 1 appears below.]
The CAFC said that the two subsets did not need to simultaneously exist. The claim was not limited to compounds that were in both subsets because, construed in context, the claim to compounds that were of a first subset “and” a second subset covered compounds that were either in the first group “or” the second subset.
Here “and” meant to “join alternatives” because, in this case, the claim did not use the word “and” in isolation. Rather, the claim used “and” in a larger context with clarifying adverbs “independently” and “together.”
More on the word “AND”
Chef America v. lamb-Weston, 358 F.3d 1371 (Fed. Cir. 2004)
- A court may not re-write a patent claim even to avoid a nonsensical result.
- Here, however, giving “and” its most common dictionary meaning would fail to cover the patent owners own drug product and render dependent claims meaningless
The CAFC distinguished Chef America:
To the contrary, this court and the district court must interpret the term to give proper meaning to the claim in light of the language and intrinsic evidence. Giving and its most common dictionary meaning would produce in this case the nonsensical result of not covering topiramate and rendering several other dependent claims meaningless. In Chef America, the only possible interpretation of the claim led to a nonsensical result. This situation is distinguishable because claim 1 can and should be interpreted as the patentees intended, with the meaning of and connoting alternatives.
https://en.wikipedia.org/wiki/Topiramate
4-Aminopyridine: Acorda Win & Loss
May 3, 2017
Acorda won at the PTAB but lost in the US District Court.
Acorda Therapeutics, Inc. is fighting is to extend the life of their 4-aminopyridine formulations and methods.
Acorda will retain market exclusivity to AMPYRA® (dalfampridine) Extended Release Tablets, 10 mg at least through July 2018.
The US District Court in Delaware ruled that Acorda’s four patents set to expire between 2025 and 2027 are invalid. A few weeks earlier, the United States Patent and Trademark Office (USPTO) Patent Trials and Appeal Board (PTAB) upheld the four patents challenged via the inter partes review (IPR) process [U.S. Patent Nos. 8,663,685 (the ‘685 patent), 8,440,703 (the ‘703 patent), 8,354,437 (the ‘437 patent) and 8,007,826 (the ‘826 patent)]. These patents, if valid and enforceable, are calculated to expire in 2025, 2025, 2026 and 2027, respectively.
ACORDA THERAPEUTICS, INC., et al. v. ROXANE LABORATORIES, INC., et al.
Case #: 14-882
Judge: Chief Judge Leonard P. Stark
Next?: Acorda will appeal. Meanwhile Acorda announced restructuring and layoffs
http://cen.acs.org/articles/95/i15/Troubled-biotechs-cut-jobs.html
Fierce Pharma
http://www.fiercepharma.com/pharma/court-nixes-4-acorda-patents-teeing-up-amprya-generics-for-2018
Acorda press releases
Steadymed wins IPR Challenge of United Therapeutics’s Remodulin® Product-by-Process Patent Claims
Final Decision – March 31, 2017
IPR2016-00006
STEADYMED LTD., (Petitioner) v. UNITED THERAPEUTICS CORPORATION, (Patent Owner)
U.S. Patent No. 8,497,393 B2 “Process to Prepare Treprostinil, the Active Ingredient in Remodulin®”
Link to PDF: https://ptabdata.uspto.gov/ptab-api/documents/663936/native
Pharmacosmos v. Luitpold
A pair of PTAB disputes between Pharmacosmos A/S v. Luitpold Parms. Inc should be interesting read. I’ll follow up with more detail.
IPR2015-01495
IPR2015-01490
