Leonard J. Chyall, Ph.D. __________________
`
`Chyall Pharma, 1281 Win Hentschel Blvd, West Lafayette, Indiana 47906 USA
`Tel 765.237.3391 (office); Tel 765.413.3207 (mobile)
`
`Education
`
`B.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
`
`June 2020 –
`
`May 2011 –
`
`2000-2011
`
`1996-2000
`
`Purdue University; West Lafayette, Indiana
`Lecturer – Department of Chemistry
`Teaching responsibilities include introductory organic chemistry
`courses offered to undergraduate life sciences majors.
`
`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.
`
`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. Projects involved
`new product developments (primarily pharmaceuticals) or providing
`scientific consulting to support patent litigation and counterfeit/-
`tampering analysis. Department leader responsible for fee-for-service
`laboratory testing and consulting services. Responsible for business
`development, client relations, and strategic planning of the business.
`Administrative supervisor for numerous chemists throughout my
`tenure with the company.
`
`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.
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`Representative Technical Skills
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`Analytical Chemistry
`• Mass Spectrometry
`- Triple Quadrupole Systems
`- Ion Cyclotron Resonance MS
`- Ion-Molecule Chemistry
`• Chromatography (HPLC, MPLC, TLC and
`preparative chromatography)
`Infrared (IR) and Raman Spectrometry
`•
`• NMR spectroscopy
`• Spectrophotometry
`• Solubility and dissolution testing
`- USP dissolution testing
`- Intrinsic dissolution rate studies
`• Powder dissolution testing
`• pH measurements
`• Potentiometric titrations
`• Karl Fischer titration
`
`
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`Professional Affiliations and Activities
`
`
`Organic Chemistry
`• Synthetic chemistry
`- mg to kg scale laboratory reactions
`- high pressure reactions
`- air-sensitive procedures
`• Crystallization methods
`• Enantiomer resolutions
`• Polymorph, salt and cocrystal screening
`and characterization
`
`
`Solid Form Analytical Techniques
`• X-ray powder diffraction (XRPD)
`• Thermogravimetric analyses (TGA)
`• Differential scanning calorimetry (DSC)
`• Optical microscopy
`• Moisture sorption/desorption analyses
`
`
`
`• American Chemical Society
`• American Association of Pharmaceutical Scientists
`• Purdue Research Park Life Sciences Executive Council
`• Guest Lecturer, Chemistry Department, Purdue University (Undergraduate
`Organic Chemistry Courses) 2016 – 2017.
`
`
`Publications
`
`1. Chyall, L, J. Current Applications of X-Ray Powder Diffraction in the Pharmaceutical
`Industry Am. 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, Succinic, and Fumaric Acids. J. Am. Chem. Soc. 2004, 126, 13335-13342.
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`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: Isolation 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. Crystal Growth & Design 2002, 2, 505-510.
`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 Materials 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 Spectrom. 1999, 10(9), 896-906.
`9. Gassman, P. G.; Han, S.; Chyall, L. J. Thermal rearrangement of trans-7,7-
`dihalobicyclo[4.1.0]hept-3-enes. Tetrahedron Lett. 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 Ionization and the Flowing Afterglow
`Method. Rapid Commun. Mass 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.; Kenttämaa, H. I. Homolytic Se-H Bond Energy
`and Ionization 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 of cyclopropenylidene. Int. J. Mass Spectrom. Ion Processes 1995,
`149/150, 257-266.
`14. Smith, R. L.; Chyall, L. J.; Beasley, B. J.; Kenttämaa, H. I. The Site of Protonation of
`Aniline. J. Am. Chem. Soc. 1995, 117, 7971-7973.
`15. Chou, P. K.; Smith, R. L.; Chyall, L. J.; Kenttämaa, H. I. Reactivity of the Prototype
`Organosulfur Distonic Ion: •CH2SH2+ J. Am. Chem. Soc. 1995, 117, 4374-4378.
`16. Chyall, L. J.; Kenttämaa, H. I. Gas-phase reactions of the 4-dehydroanilinium ion
`and its isomers. J. Mass Spectrom. 1995, 30, 81-87.
`17. Chyall, L. J.; Byrd, M. H. C.; Kenttämaa, H. I. Reactions of the Charged Radical
`(CH3)2S+-CH2• with Cyclic Alkenes. J. Am. Chem. Soc. 1994, 116, 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, 116, 8681-8690.
`19. Chyall, L. J.; Kenttämaa, H. I. The 4-Dehydroanilinium Ion: a Stable Distonic
`Isomer of Ionized Aniline. J. Am. Chem. Soc. 1994, 116, 3135-3136.
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`20. Smith, R. L.; Chyall, L. J.; Stirk, K. M.; Kenttämaa, H. I. Radical-type reactivity of
`the methylenedimethylsulfonium ion, (CH3)2S+-CH2• Org. Mass Spectrom. 1993, 28,
`1623-1631.
`21. Smith, R. L.; Chyall, L. J.; Chou, P. K.; Kenttämaa, H. I. The Acyclic Distonic
`Isomer of Ionized Cyclopentanone: •CH2CH2CH2CH2CO+ 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.
`23. Brickhouse, M. D.; Chyall, L. J.; Sunderlin, L. S.; Squires, R. R. Kinetics of isobaric
`ion/molecule reactions determined by the flowing afterglow-triple quadrupole
`technique. Rapid Commun. Mass Spectrom. 1993, 7, 383-3
`
`Patents
`1. Gushurst, K. S.; Chyall, L. J.; Koztecki, 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-1-
`carbonyl-4-fluorobenzyl]-2H-phthalazin-1-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.
`Intumescent Polymer Compositions. US 6,632,442 B1 (October 14, 2003).
`5. Robin, M. L.; Mazac, 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
`
`1. "Crystallization Studies of Nabumetone: Preparation and Characterization of a
`Novel, High-Energy Polymorph." Chyall, L. J.; Tower, J. M.; Coates, D. A.; Houston,
`T. L., 223rd National Meeting of the American Chemical Society, Orlando, FL, April
`7-11, 2002: Abstract IEC 268
`2. "The Synthesis and Properties of 7,7-Dichloro-trans-bicyclo-[4.1.0]-hept-3-ene." P.
`G. Gassman and L. J. Chyall, 22nd Great Lakes Regional Meeting of the American
`Chemical Society, Duluth, MN, May 31-June 2, 1989: Abstract 98.
`3. "The Synthesis and Thermal Isomerization of 7,7-Dihalo-trans-bicyclo-[4.1.0]-hept-
`3-enes." P. G. Gassman and L. J. Chyall, 201st National Meeting of the American
`Chemical Society, Atlanta, GA, April 14-19, 1991: Abstract ORGN 228.
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`4. "Free Radical Rearrangements of Dihalo-trans-bicyclo-[4.1.0]-hept-3-enes." P. G.
`Gassman and L. J. Chyall, 32nd National Organic Chemistry Symposium, University
`of Minnesota, Minneapolis, MN, June 16-20, 1991: Abstract B-65.
`5. "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,
`205th National Meeting of the American Chemical Society, Denver, CO, March 28-
`April 2, 1993: Abstract ORGN 29.
`6. "Ion-Molecule Chemistry of the Methylene Dimethylsulfonium Ion: A Novel Alpha-
`Distonic Ion." L. J. Chyall, R. L. Smith, K. M Stirk, and H. I Kenttämaa, 41st ASMS
`Conference on Mass Spectrometry, San Francisco, CA, May 30-June 4, 1993:
`Abstract MOD 12:10
`7. "Radical-Type Reactivity of Distonic Ions: The 4-Dehydroanilinium Ion." L. J.
`Chyall and H. I Kenttämaa, 208th National Meeting of the American Chemical
`Society, Washington, DC, August 21-25, 1994: Abstract ORGN 404.
`8. "Astrophysical Thermochemistry: The Heats of Formation of C3H2 Isomers." L. J.
`Chyall and R. R. Squires, 43rd 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
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`Chyall, L. J. The synthesis and thermal rearrangements of 7,7-dibromo-trans-
`bicyclo[4.1.0]hept-3-ene and 7,7-dichloro-trans-bicyclo[4.1.0]hept-3-ene. (1991) 192
`pp. Avail.: Univ. Microfilms Int., Order No. DA9209417 From: Diss. Abstr. Int. B 1992,
`52(10), 5264.
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