Skip to main content
SpringerLink
Log in

Impact of solid / vapour equilibria on conditions of crystallization of pharmaceutical compounds

  • Published:
Transactions of Tianjin University Aims and scope Submit manuscript

Abstract

The influence of solvent (in its gaseous state) on the stability of crystallized organic compounds was investigated. Through two examples of studies on the solid/vapour equilibria made in our lab, several behaviors were highlighted: (i) a new hydrated phase (thermodynamically stable) of an active pharmaceutical ingredient (API) was detected after the recrystallization starting from a deliquescent state, (ii) a spontaneous resolution of a hydrated racemic compound towards an anhydrous conglomerate can occur during the desolvation under the precise conditions of temperature and humidity. This study illustrates that knowledge about solid/vapour equilibrium is a crucial step during the complete characterization of solid organic compounds.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Authelin J R. Thermodynamics of non-stoichiometric pharmaceutical hydrates[J]. International Journal of Pharmaceutics, 2005, 303(1/2):37–53.

    Article  Google Scholar 

  2. Henck J O, Griesser U J, Burger A. Polymorphism of drug substances: An economic challenge[J]. Pharm Ind, 1997, 59(2): 165–169 (in German).

    Google Scholar 

  3. Khanhari R, Chen L, Grant D J W. Physical characterization of nedocromil sodium hydrates[J]. J Pharm Sci, 1998, 87(9): 1052–1061.

    Article  Google Scholar 

  4. Petit S, Coquerel G. Mechanism of several solid-solid transformations between dihydrated and anhydrous copper (II) 8-hydroxyquinolinates. Proposition for a unified model for the dehydration of molecular crystals[J]. Chem Mater, 1996, 8(9): 2247–2258.

    Article  Google Scholar 

  5. Chan M N, Kreidenweis S M, Chan C K. Measurements of hygroscopic and deliquescence properties of organic compounds of different solubilities in water and their relationship with cloud condensation nuclei activities [J]. Env Sci Tech, 2008, 42(10): 3602–3608.

    Article  Google Scholar 

  6. Coquerel G, Sanselme M, Lafontaine A. Method of Measuring Scattering of X-rays, Its Applications and Implementation Device: WO, 136921. A1 [P]. 2011-04-06 (in French).

  7. Descamps G. Purification by Crystallization of a New Organic Phosphored Active Pharmaceutical Ingredient [D]. University of Rouen, Rouen, 2009 (in French).

    Google Scholar 

  8. Amharar Y, Petit S, Sanselme M et al. Crystal structures, dehydration mechanism and chiral discrimination in the solid state of hydantoin derivatives [J]. Cryst Growth Des, 2011, 11(6): 2453–2462.

    Article  Google Scholar 

  9. Descamps G, Amharar Y, Cartigny Y et al. Novel Polymorphic Form of CHDMAPP, Method of Preparation Thereof, and Pharmaceutical Composition Comprising Same: WO, 029062.A1 [P]. 2010-03-18.

  10. Newman W, Reutzel-Edens S M, Zografi G. Characterization of the “hygroscopic” properties of an active pharmaceutical ingredient[J]. J Pharm Sci, 2008, 97(3): 1047–1059.

    Article  Google Scholar 

  11. Sakai K, Hirayama N, Tamura R. Topics in Current Chemistry (Novel Optical Resolution Technologies)[M]. Berlin Heidelberg, Springer, 2007: 1–50.

    Google Scholar 

  12. Courvoisier L, Ndzié E, Petit M-N et al. Influence of the process on the mechanisms and the performances of the preferential crystallization: Example with (±)-5-(4-bromophenyl)-5-methylhydantoin[J]. Chem Letter, 2001, 30 (4): 364–365.

    Article  Google Scholar 

  13. Belokon Y. (S)-2-[N-(N′-benzylprolyl) amino] benzophenone (BPB): A reagent for the synthesis of optically pure α-amino acids [J]. Janssen Chimica Acta, 1992, 10(2):4–12.

    Google Scholar 

  14. Tauvel G, Cartigny Y, Sanselme M et al. Study of solidliquid and solid-vapor equilibria in tenatoprazole potassium salt/solvents systems [C]. In: 37th Conference on Phase Equilibria Proceedings. EDP Sciences, 2011.

  15. Couvrat N, Cartigny Y, Coquerel G. Influence of solid/vapour equilibria on the stability of organic solids [J]. In: 35th Conference on Phase Equilibria Proceedings. EDP Sciences, 2009.

  16. Descamps G, Cartigny Y, Sanselme M et al. Structural and physico-chemical characterization of a solid solution produced by antisolvent crystallization of a new phosphoantigen [J]. Crystal Growth Des, 2009, 9(9): 3910–3917.

    Article  Google Scholar 

  17. Balavoine F, Madec J, Schneider J-M et al. Method for the Preparation of (3S,3S′) 4,4′-Disulfanediylbis(3-Aminobutane 1-sulfonic acid): WO, 045849[P]. 2012-04-12.

Download references

Author information

Authors and Affiliations

  1. Laboratory of Separative methods and Sciences, Crystallogenesis Unit, University of Rouen, 76821, Mont Saint Aignan Cedex, France

    Yohann Cartigny & Gerard Coquerel

Authors
  1. Yohann Cartigny
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gerard Coquerel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yohann Cartigny.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cartigny, Y., Coquerel, G. Impact of solid / vapour equilibria on conditions of crystallization of pharmaceutical compounds. Trans. Tianjin Univ. 19, 53–57 (2013). https://doi.org/10.1007/s12209-013-1800-7

Download citation

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12209-013-1800-7

Keywords

Search

Navigation