Salt Selection and Simultaneous Polymorphism Assessment via High-Throughput Crystallization: The Case of Sertraline

Organic Process Research and Development

Volumn 7, Issue 6, 2003, Pages 990-996

  Remenar, Julius F ^a   MacPhee, J Michael ^a   Larson, Bridget K ^a   Tyagi, Viraj A ^a   Ho, Jason H ^a   McIlroy, David A ^a   Hickey, Magali B ^a   Shaw, Paul B ^a   Almarsson, Örn ^a  

^a TransForm Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SERTRALINE;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL REACTION; CRYSTAL; CRYSTALLIZATION; DRUG SYNTHESIS; PREDICTION; REACTION ANALYSIS; SOLID;

EID: 0346104829     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op034115+     Document Type: Article

References (23)

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2. Gould, P. L. Int. J. Pharm. 1986, 33, 201-217.
3. Bernstein, J. Polymorphism and Patents; In Polymorphism in Molecular Crystals; Oxford: New York, 2002; pp 297-307.
4. Desrosiers, R. High Throughput Screening Techniques for Preformulation: Salt Selection and Polymorph Studies. 2001. Scientific Update. International Symposium on Polymorphism and Crystallization. San Francisco, November 13, 2001.
5. Morris, K. R.; Fakes, M. G.; Thakur, A. B.; Newman, A. W.; Singh, A. K.; Venit, J. J.; Spagnuolo, C. J.; Serajuddin, A. T. M. Int. J. Pharm. 1994, 105, 209-217.
6. Tong, W.; Whitesell, G. Pharm. Dev. Technol. 1998, 3, 215-223.
7. Morissette, S. L.; Read, M.; Soukasene, S.; Tauber, M.; Scoppettuolo, L. ; Apgar, J.; Guzman, H.; Sauer, J.; Collins, D.; Jadhav, P. K.; Engler, T.; Gardner, C. R. High Throughput Crystallization of Polymorphs and Salts: Applications in Early Lead Optimization. Abstracts of the 225th National Meeting, American Chemical Society, New Orleans, 2003.
8. Bauer, J.; Spanton, S.; Henry, R.; Quick, J.; Dziki, W.; Porter, W.; Morris, J. Pharm. Res. 2001, 18, 859-866.
9. Patent information on forms of sertraline hydrochloride was collected from the following documents: (a) (Pfizer). U.S. Patent 5,248,699. (b) (Torcan). EP 0 928 784 A1; (c) (Teva). WO 00/32551 A1. (d) (CIBA Specialty Chemicals Holding Inc.). WO 01/32601 A1. (e) (Teva). WO 01/45692 A1.
10. Patent information on forms of sertraline hydrochloride was collected from the following documents: (a) (Pfizer). U.S. Patent 5,248,699. (b) (Torcan). EP 0 928 784 A1; (c) (Teva). WO 00/32551 A1. (d) (CIBA Specialty Chemicals Holding Inc.). WO 01/32601 A1. (e) (Teva). WO 01/45692 A1.
11. Patent information on forms of sertraline hydrochloride was collected from the following documents: (a) (Pfizer). U.S. Patent 5,248,699. (b) (Torcan). EP 0 928 784 A1; (c) (Teva). WO 00/32551 A1. (d) (CIBA Specialty Chemicals Holding Inc.). WO 01/32601 A1. (e) (Teva). WO 01/45692 A1.
12. Patent information on forms of sertraline hydrochloride was collected from the following documents: (a) (Pfizer). U.S. Patent 5,248,699. (b) (Torcan). EP 0 928 784 A1; (c) (Teva). WO 00/32551 A1. (d) (CIBA Specialty Chemicals Holding Inc.). WO 01/32601 A1. (e) (Teva). WO 01/45692 A1.
13. Patent information on forms of sertraline hydrochloride was collected from the following documents: (a) (Pfizer). U.S. Patent 5,248,699. (b) (Torcan). EP 0 928 784 A1; (c) (Teva). WO 00/32551 A1. (d) (CIBA Specialty Chemicals Holding Inc.). WO 01/32601 A1. (e) (Teva). WO 01/45692 A1.
14. Almarsson, Ö.; Hickey, M. B.; Peterson, M. L.; Morissette, S. L.; McNulty, C.; Soukasene, S.; Tawa, M.; MacPhee, M.; Remenar, J. F. Cryst. Growth Des. 2003. In press.
15. Morissette, S. L.; Soukasene, S.; Levinson, D.; Cima, M. J.; Almarsson, Ö. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 2180-2184.
16. Peterson, M. L.; Morissette, S. L.; McNulty, C.; Goldsweig, A.; Shaw, P. ; LeQuesne, M.; Monagle, J.; Encina, N.; Marchionna, J.; Johnson, A.; Gonzales-Zugasti, J.; Lemmo, A. V.; Ellis, S. J.; Cima, M. J.; Almarsson, Ö. J. Am. Chem. Soc. 2002, 124, 10958-10959.
17. Stracer, L. H. CAD4-EXPRESS, Enraf-Nonius, Delft, The Netherlands, 1992.
18. Watkin, D. J.; Prout, C.; Caruthers, J.; Betteridge, P. W.; Cooper, R. I. CRYSTALS, Issue 11.8, Chemical Crystallography Laboratory, University of Oxford: Oxford, U.K. 2002; Watkin, D. J.; Prout, C. K.; Pearce, L. J. CAMERON: Chemical Crystallography Laboratory, University of Oxford: Oxford, U.K. 2002.
19. Watkin, D. J.; Prout, C.; Caruthers, J.; Betteridge, P. W.; Cooper, R. I. CRYSTALS, Issue 11.8, Chemical Crystallography Laboratory, University of Oxford: Oxford, U.K. 2002; Watkin, D. J.; Prout, C. K.; Pearce, L. J. CAMERON: Chemical Crystallography Laboratory, University of Oxford: Oxford, U.K. 2002.
20. w = 0.0437.
21. Hydrogen bonds involved in the primary motif: N(1)-H(1)⋯Br(1) [2 - x, 1/2 + y, 3/2 - z, 3.320Å, 155°], N(1)-H(2)⋯Br(1) [x, y, z, 3.301Å, 157°].
22. Secondary hydrogen bonds: C(17)-H(171)⋯Cl(2) [3 79 Å 162°] C(7)-H(71)⋯Cl(2) [3.83 Å, 147°], C(10)-H(101) ⋯Cl(1) [3.69 Å, 130°]
23. Caruso, F.; Besmer, A.; Rossi, M. Acta Crystallogr., Sect. C 1999, 55, 1712.