Formation of solid solutions between racemic and enantiomeric citalopram oxalate

Chirality

Volumn 23, Issue 5, 2011, Pages 408-416

  De Diego, Heidi Lopez ^a,c   Bond, Andrew D ^b   Dancer, Robert James ^a  

^a H LUNDBECK A S   (Denmark)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c Department of Process Research ^*  (Denmark)

Author keywords

binary phase diagram; citalopram; crystal structure; disorder; escitalopram oxalate; isostructural; racemic compound; solid solutions; ternary phase diagram

Indexed keywords

CITALOPRAM; CITALOPRAM OXALATE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SOLUBILITY; DRUG STRUCTURE; ENANTIOMER; MELTING POINT; PRIORITY JOURNAL; RACEMIC MIXTURE; SOLID STATE; X RAY DIFFRACTION; X RAY POWDER DIFFRACTION;

ANTIDEPRESSIVE AGENTS, SECOND-GENERATION; CALORIMETRY, DIFFERENTIAL SCANNING; CITALOPRAM; MOLECULAR CONFORMATION; OXALATES; SOLUBILITY; SOLUTIONS; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 79954608037     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20943     Document Type: Article

References (16)

1. Moss GP,. Basic terminology of stereochemistry (IUPAC Recommentations 1996). Pure Appl Chem 1996; 68: 2193-2222.
2. Jacques J, Collet A, Wilen SH,. Enantiomers, racemates and resolutions. New York: John Wiley & sons; 1981.
3. Tabora JE, Corry J, Osifchin R, Lepore JV, Davidson OA, Thien MP,. Identification and characterization of an anomalous racemate. Fluid Phase Equilib 2007; 258: 140-147. (Pubitemid 47102020)
4. Polenske D, Lorenz H, Seidel-Morgenstern A,. Potential of different techniques of preferential crystallization for enantioseparation of racemic compound forming systems. Chirality 2009; 21: 728-737.
5. Burke WJ,. Escitalopram. Expert Opin Investig Drugs 2002; 11: 1477-1486. (Pubitemid 35174942)
6. Hyttel J, Bøgesø KP, Perregaard J, Sánchez C,. The pharmacological effect of citalopram resides in the (S)-(+) enantiomer. J Neural Transm 1992; 88: 157-160.
7. Sanchez C, Bogeso KP, Ebert B, Reines EH, Braestrup C,. Escitalopram versus citalopram; the surprising role of the R-enantiomer. Psychopharmacology 2004; 174: 163-176. (Pubitemid 38916289)
8. Elati CR, Kolla N, Vankawala PJ, Gangula S, Chalamala S, Sundaram V, Bhattacharya A, Vurimidi H, Mathad VT,. Substrate modification approach to achieve efficient resolution: didesmethylcitalopram: a key intermediate for escitalopram. Org Process Res Dev 2007; 11: 289-292.
9. Dancer RJ, Lopez de Diego H,. Attempted resolution of citalopram using (-)-O-O'-di-p-toluoyl-(R,R)-tartaric acid, and reflections on an alkylation reaction; Comment on an Article by Elati et al. Org Process Res Dev 2009; 13: 23-33.
10. Harrison WTA., Yathirajan HS, Bindya S, Anilkumar HG, Devaraju,. Escitalopram oxalate: co-existence of oxalate dianions and oxalic acid molecules in the same crystal. Acta Crystallogr C 2007; 63, o129-o131.
11. Apex 2: Bruker AXS. Apex 2. Version 1.0-22. Madison, WI: Bruker AXS; 2004.
12. Sheldrick GM,. A short story of SHELX. Acta Crystallogr A 2008; 64: 112-122.
13. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, van de Streek J,. Mercury: visualization and analysis of crystal structures. J Appl Cryst 2006; 39: 453-457. (Pubitemid 43806296)
14. Chen AM, Wang Y, Wenslow RM,. Purification of partially resolved enantiomeric mixtures with the guidance of ternary phase diagram. Org Process Res Dev 2008; 12: 271-281.
15. Huans J, Chen S, Guzei IA, Yu L,. Discovery of a solid solution of enantiomers in a racemate-forming system by seeding. J Am Chem Soc 2006; 128: 11985-11992. (Pubitemid 44360236)
16. Rollinger JM, Burger A,. Polymorphism of racemic felodipine and the unusual series of solid solutions in the binary system of its enantiomers. J Pharm Sci 2001; 90: 949-959. (Pubitemid 32645951)