Leonard J. Chyall, Ph.D.
`Chyall Pharma, 1281 Win Hentsehel Blvd, West Lafayette, Indiana 47906 USA
`Tel 765.237.3391 (office); Tel 765.413.3207 (mobile)
`
`Education
`
`l3.A. (Chemistry), 1986, Oberlin College, Oberlin, OH
`Ph.D. (Chemistry), 1991, University of Minnesota, Minneapolis, MN
`Postdoctoral Fellow, 1992-1996, Purdue University, West Lafayette, IN
`Pharmaceutical Solids and Regulatory Affairs Short Course, Purdue University, 2001
`
`Employment
`
`May 2011 —
`
`Chyall Pharmaceutical Consulting, LLC; West Lafayette, Indiana
`President and Consultant
`
`Independent consultant serving the pharmaceutical industry. Expertise
`in synthetic chemistry, and analytical testing of drug substances and
`drug products. Services directed toward scientific data and document
`review, laboratory testing, and technical assistance with IP matters.
`
`2000-2011
`
`Aptuit, Inc. (formerly SSCI, Inc.), West Lafayette, Indiana
`
`Director (August 2010 — May 2011)
`Principal (January 2007 — July 2010)
`Senior Research Investigator (2003 - 2006)
`Research Investigator (2000 - 2003)
`Project manager and group leader for external client projects involving
`various aspects of organic and analytical chemistry. These projects
`involve the development of new products (primarily pharmaceuticals)
`or providing scientific consulting to support patent litigation,
`counterfeit analysis or tampering analysis projects. Leader ofa
`department responsible for fee-for—service laboratory testing and
`
`consulting services. Responsible for business development, client
`relations, and strategic planning ofthe business. Administrative
`supervisor for numerous chemists throughout my tenure with the
`organization.
`
`1996-2000
`
`Great Lakes Chemical (now Chemtura), West Lafayette, Indiana
`Research Chemist
`
`Lead Scientist for a new technology development program in the
`GLCC Corporate R&D division. Technology Coordinator for contract
`research programs. Project Leader for a new product development
`project in GLCC Polymer Additives R&D.
`
`February-10-2016
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`Representative Technical Skills
`
`Analytical Chemistry
`- X-ray powder diffraction (XRPD)
`-
`Therrnogravimetric analyses (TGA)
`- Differential scanning calorimetry (DSC)
`- Optical microscopy
`-
`Infrared (IR) and Raman spectroscopy
`- Moisture sorption/desorption analyses
`- NMR spectroscopy
`-
`Spectrophotometry
`-
`Solubility and dissolution testing
`-
`pH measurements, potentiometric titrations
`- Karl Fischer analyses
`
`Organic Chemistry
`-
`Synthetic chemistry
`O mg to kg scale laboratory reactions
`0 high pressure reactions
`0 air-sensitive procedures
`- Crystallization methods
`-
`Enantiomer Resolutions
`-
`Polymorph, salt and cocrystal screening
`and characterization
`- Analytical chromatography (HPLC and
`TLC)
`Preparative chromatography
`
`-
`
`Professional Affiliations
`
`° American Chemical Society
`° American Association of Pharmaceutical Scientists
`
`°
`
`Purdue Research Park Life Sciences Executive Council
`
`Publications
`
`1. Chyall, L, J. Current Applications of X—Ray Powder Diffraction in the Pharmaceutical
`Industry/lm. Pharm. Rev. 2012, 15, 70-73.
`
`2. Park, A.; Chyall, L.; Dunlap, J.; Schertz, C.; Jonaitis, D.; Stahly, B.; Bates, S.;
`Shipplett, R.; Childs S. New solid—state chemistry technologies to bring better drugs
`to market: knowledge—based decision making. Exp. Opin. Drug Disc, 2007, 2(1),
`145-154.
`
`3. Lohani, S.; Zhang, Y.; Chyall, L. J.; Mougin—Andres, P.; Muller, F. X.; Grant, D. J.
`W. Carbamazepine—2,2,2—trifluoroethanol (1/1). Acta Cryst. 2005, E61, 1310-1312.
`
`4. Childs, S. L.; Chyall L. J.; Dunlap, J. T.; Smolenskaya, V. N.; Stahly B. C.; Stahly, G.
`
`P. Crystal Engineering Approach to Forming Cocrystals of Amine Hydrochlorides
`with Organic Acids. Molecular Complexes of Fluoxetine Hydrochloride with
`Benzoic, Suecinic,and Fumaric Acids. J. Am. Chem. Soc. 2004, 126, 13335-13342.
`
`5. Childs, S. L.; Chyall L. J.; Dunlap, J. T.; Coates, D. A.; Stahly B. C.; Stahly, G. P. A
`Metastable Polymorph of Metformin Hydrochloride:
`lsolation and Characterization
`Using Capillary Crystallization and Thermal Microscopy Techniques. Crystal
`Growth & Design 2004, 4, 441 -449.
`
`6. Chyall, L. J.; Tower, J. M.; Coates, D. A.; Houston, T. L.; Childs, S. L. Polymorph
`Generation in Capillary Spaces: The Preparation and Structural Analysis of a
`Metastable Polymorph of Nabumetone. Cry.s'tal Growth & Design 2002, 2, 505-510.
`
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`7. Morgan, A. B.; Harris, R. H., Jr.; Kashiwagi, T.; Chyall, L. J.; Gilman, J. W.
`Flammability of polystyrene layered silicate (clay) nanocomposites: Carbonaceous
`Char formation. Fire and M'atem'al.s' 2002, 26, 247-253.
`
`8. Hill, B. T.; Poutsma,J. C.; Chyall, L. J.; Hu, J.; Squires, R. R. Distonic ions of the
`
`"Ate" Class.
`
`J’. Am. Soc. Mass Spectrum. 1999, 10(9), 896-906.
`
`9. Gassman, P. G.; Han, S.; Chyall, L. J . Thermal rearrangement of trans-7,7-
`diha1obicyc1o[4.1 .0]hept-3-enes. Tetrahedron Letr. 1998, 39(31), 5459-5462.
`
`10. Poutsma, J. C.; Seburg, R. A.; Chyall, L. J.; Sunderlin, L. S.; Hill, B. T.; Hu, J.;
`Squires, R. R. Combining Electrospray lonization and the Flowing Afterglow
`Method. Rapid Commun. Ma.s'.v Spectrom. 1997, 11, 489-493.
`
`11. Chyall, L. J.; Squires, R. R. The Proton Affinity and Absolute Heat of Formation of
`Trifluoromethanol. J. Phys. Chem. 1996, 100, 16435-16440.
`
`12. Leeck, D. T.; Li, R.; Chyall, L. J.; Kenttamaa, H. I. Homolytic Se-H Bond Energy
`and lonization Energy of Benzeneselenol, and the Acidity of the Corresponding
`Radical Cation. J. Phys. Chem. 1996, 100, 6608-6611.
`
`13. Chyall, L. J.; Squires, R. R. Determination of the proton affinity and absolute heat of
`formation ofcyclopropenylidene. Int. J. Mass‘ Spectrum. Ion Pr()ceS.s'e.s' 1995,
`149/150, 257-266.
`
`14. Smith, R. L.; Chyall, L. J.; Beasley, B. J.; Kenttamaa, H. 1. The Site ofProtonation of
`Aniline. J. Am. Chem. Soc. 1995, 117, 7971-7973.
`
`15. Chou, P. K.; Smith, R. L.; Chyall, L. J.; Kenttamaa, H. 1. Reactivity ofthe Prototype
`Organosulfur Distonic 1on: 'CHgSHgl J. Am. Chem. Soc. 1995, 117, 4374-4378.
`
`16. Chyall, L. J.; Kenttamaa, H. I. Gas—phase reactions of the 4—dehydroanilinium ion
`and its isomers. J. Ma.v.s' Spectrom. 1995, 30, 81-87.
`
`17. Chyall, L. J.; Byrd, M. H. C.; Kenttamaa, H. 1. Reactions of the Charged Radical
`(CH3)~_:S+—CH3- with Cyclic Alkenes. J. Am. Chem. Soc. 1994, 1'16, 10767-10772.
`
`18. Chyall, L. J.; Brickhouse, M. D.; Schnute, M. E.; Squires, R. R. Kinetic Versus
`Thermodynamic Control in the Deprotonation of Unsymmetrical Ketones in the Gas
`Phase. J. Am. Chem. Soc. 1994, 1'16, 8681-8690.
`
`19. Chyall, L. J.; Kenttamaa, H. I. The 4—Dehydroanilinium Ion: a Stable Distonic
`Isomer oflonized Aniline. J. Am. Chem. Soc. 1994, 116, 3135-3136.
`
`20. Smith, R. L.; Chyall, L. J.; Stirk, K. M.; Kenttamaa, H. l. Radical-type reactivity of
`the methylenedimethylsulfonium ion, (CH3)3S+-CH3‘ Org. Mass Spectrom. 1993, 28,
`1623-1631.
`
`21. Smith, R. L.; Chyall, L. J.; Chou, P. K.; Kenttéimaa, H. I. The Acyclic Distonic
`Isomer oflonized Cyclopentanone: 'CH3CH3CH3CH3CO+ J. Am. Chem. Soc. 1994,
`116, 781-782.
`
`22. Mlinaric-Majerski, K.; Vinkovic, V.; Chyall, L. J.; Gassman, P. G. Deuterium
`isotope effects on nuclear shielding. Cross—ring effects in rigid cyclic molecules.
`Magn. Reson. Chem. 1993, 31, 903-905.
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`23. Brickhouse, M. D.; Chyall, L. J.; Sunderlin, L. S.; Squires, R. R. Kinetics ofisobaric
`ion/molecule reactions determined by the flowing afterglow-triple quadrupole
`technique. Rapid Commtm. Ma.s'.v Spectrum. 1993, 7, 383-3
`
`Patents
`
`1. Gushurst, K. S.; Chyall, L. J.; Kozteeki, L. H.; Wolfe, B. S. Crystalline forms of
`oxymorphone hydrochloride US 8,563,571 (October 22, 2013).
`
`2. Quigley, K. A.; Still, E. J.; Chyall, L. J. 4—[3[(4—Cyclopropanecarbonyl—piperazine—l-
`earbonyl—4—fluorobenzyl]—2H—phthalazin— I —one. US 8,183,369 B2 (May 22, 2012).
`
`3. Chyall, L. J.; Hodgen, H. A.; Vyverberg, F. J.; Chapman, R. W. Intumescent
`
`Polymer Compositions. US 6,905,693 (June 14, 2005).
`
`4. Chyall, L. J.; Hodgen, H. A.; Vyverberg, F. J.; Chapman, R. W.; Chou, P. K.
`
`Intumeseent Polymer Compositions. US 6,632,442 B1 (October 14, 2003).
`
`5. Robin, M. L.; Mazae,C. J.; Chyall, L. J.; Kleindl, P. Bromine-containing 1,2-
`
`bis(phenyl)difluoromethanes and method of imparting flame retardancy to flammable
`
`materials. US 6,348,633 (February 19,2002).
`
`Papers Presented
`
`l.
`
`2.
`
`3.
`
`4.
`
`5.
`
`6.
`
`"Crystallization Studies of Nabumetone: Preparation and Characterization of a
`Novel, High—Energy Polymorph.“ Chyall, L. J.; Tower, .1. M.; Coates, D. A.; Houston,
`T. L., 223'" National Meeting of the American Chemical Society, Orlando, FL, April
`7-11, 2002: Abstract IEC 268
`
`"The Synthesis and Properties of 7,7—Dichloro—trans—bicyclo-[4.1.0]-hept—3—ene." P.
`G. Gassman and L. J. Chyall, 22"" Great Lakes Regional Meeting of the American
`Chemical Society, Duluth, MN, May 31-June 2, 1989: Abstract 98.
`
`“The Synthesis and Thermal lsomerization of 7,7-Dihalo-mm.s'-bicyclo-[4.1.0]-hept-
`3—enes.“ P. G. Gassman and L. J. Chyall, 201" National Meeting ofthe American
`Chemical Society, Atlanta, GA, April 14-19, 1991: Abstract ORGN 228.
`
`"Free Radical Rearrangements of Dihalo-trcms-bicyclo-[4. 1 .0]-hept-3-enes." P. G.
`Gassman and L. J. Chyall, 32"" National Organic Chemistry Symposium, University
`of Minnesota, Minneapolis, MN, June 16-20, 1991: Abstract B-65.
`
`“Kinetic Versus Equilibrium Control in the Deprotonation of Unsymmetrical Ketones
`in the Gas Phase.“ L. J. Chyall, M. D. Brickhouse, M. E. Schnute, and R. R. Squires,
`205"‘ National Meeting of the American Chemical Society, Denver, CO, March 28-
`April 2, 1993: Abstract ORGN 29.
`
`"Ion—Molecule Chemistry ofthe Methylene Diinethylstllfonitlin Ion: A Novel Alpha-
`Distonic Ion." L. J. Chyall, R, L. Smith, K, M Stirk, and H. I Kenttamaa, 41“ ASMS
`Conference on Mass Spectrometry, San Francisco, CA, May 30—June 4, 1993:
`Abstract MOD 12: 10
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`7'.
`
`8.
`
`"Radical—Type Reactivity of Distonic Ions: The 4-Dehydroanilinium Ion.“ L. J.
`Chyall and H. I Kenttamaa, 2081" National Meeting of the American Chemical
`Society, Washington, DC, August 21-25, 1994: Abstract ORGN 404.
`
`"Astrophysical Therrnochernistry: The Heats ofFormation of C3H2 Isomers.“ L. J.
`Chyall and R. R. Squires, 43'“ ASMS Conference on Mass Spectrometry, Atlanta,
`GA, May 21-26, 1995: Abstract WOE 11:50.
`
`Invited Lectures
`
`1. “Environmentally Friendly Fire Suppression Technology.” Department of Chemistry,
`Purdue University, West Lafayette, IN. April 8, 1997.
`
`2. “The Proton Affinity and Absolute Heat of Formation of Trifluoromethanol.” Joint
`Institute Laboratory for Astrophysics, University of Colorado, Boulder, CO. March
`1, 1996.
`
`3. “Understanding the Atmospheric Fate of Hydrofluorocarbons: Thermochemisty of
`Trifluoromethanol." Aeronomy Laboratory, National Oceanic and Atmospheric
`Administration, Boulder, CO. February 29, 1996.
`
`Dissertation
`
`Chyall, L. J. The synthesis and thermal rearrangements of 7,7—dibro1no—trans—
`bicyclo[4.l.0]hcpt—3—cnc and 7,7—dichloro—tran.s'—bicyclo[4.l .0]hept—3—cnc. (1991) 192
`
`pp. Avail.: Univ. Microfilms 1nt., Order No. DA92094l 7 From: Diss. Abstr. Int. B 1992,
`52(l O), 5264.
`
`Testimony at Deposition or at Trial (Previous 4 Years)
`
`Te.s't:'m(my provided on behalfof underlined party.
`
`1. Cephalon Inc. v. Mylan Pharmaceuticals, Inc. at al. MDL Docket No. 1:10-md—
`2200—GMS (D.Del.) (deposition).
`
`2. Shire LLC et al. V. Amneal Pharmaceuticals LLC et at’. C.A. No. 2:11-cv-03781-
`
`SRC—CLW (DNJ) (deposition).
`
`
`3. Apotex, Inc. and Apotex Corp. V. UCB Inc. Schwarz Pharma Inc. and Kremers
`Urban Pharmaceuticals Inc. C.A. No. 0:12-cv-60706-DMM (S.D. Fla.)
`(deposition and trial).
`
`4. Pfizer Inc., Wyeth Pharmaceuticals Inc. and PF Prism CV V. Apotex, Inc., et at’.
`C.A. No. 12-808—SLR Consolidated (D. Del.) (deposition).
`
`5. Opposition to Israel Patent Application No. ILl7'2563, Teva Pharmaceutical
`v. Merck & Co. (hearing).
`
`6. Pfizer Inc. and UCB Pharma GmbH V. Alkem Laboratories Ltd., at at’. C.A. No.
`13-11 10 (GMS) Consolidated (D. Del.) (deposition and trial).
`
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`7'. Supernus Pharmaceuticals, Inc. V. Actavis Inc. CA. No. 13-4740 (RMB)(JS) (D.
`Del.) (deposition and trial).
`
`8. Chiesi, Inc., Cornerstone Biophanna, Inc., and EKR Therapeutics, LLC V. Exela
`Pharma Sciences, LLC, Exela Pharmasci, Inc., and Exela Holdings, Inc. CA. No.
`l3—cv—0l275-GMS (D. Del.) (deposition).
`
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