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Poly (ortho esters)

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Biopolymers I

Part of the book series: Advances in Polymer Science ((POLYMER,volume 107))

Abstract

The synthesis and characterization of four distinct families of poly (ortho esters) are described and designated as poly (ortho esters) I, II, III and IV. Poly (ortho ester) I is prepared by the transesterification of diethoxytetrahydrofuran with diols. Poly (ortho ester) II is prepared by the condensation of 3,9-bis (ethylidene 2,4,8,10-tetraoxaspiro [5, 5] undecane) with diols to produce a linear polymer or with a triol to produce a crosslinked polymer. Poly (ortho ester) III is prepared by the condensation of a flexible triol with and alkyl orthoacetate to produce ointment-like materials. Poly (ortho ester) IV is prepared by the condensation of a rigid triol with and alkyl orthoacetate to produce solid materials. The detailed mechanism of hydrolysis of these polymers has been determined and drug release data for a number of therapeutic agents are presented.

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5 References

  1. Heller J, Baker RW, Gale RM, Rodin JO (1978) J Appl Polymer Sci 22: 1991

    Article  Google Scholar 

  2. Chasin M, Domb A, Ron E, Mathiowitz E, Langer R, Leong K, Laurencin C, Brem H, Grossman S (1990) In: Chasin M, Langer R (eds) Biodegradable polymers as drug delivery systems, Marcel Dekker, New York, p 43

    Google Scholar 

  3. Heller J, Sparer RV, Zentner GM (1990) In: Chasin M, Langer R (eds) Biodegradable polymers as drug delivery systems, Marcel Dekker, New York, p 121

    Google Scholar 

  4. Lappas LC, McKeehan WJ (1962) J Pharm Sci 51: 108

    PubMed  Google Scholar 

  5. Lappas LC, McKeehan WJ (1965) J Pharm Sci 54: 176

    PubMed  Google Scholar 

  6. Lappas LC, McKeehan WJ (1965) J Pharm Sci 56: 1257

    Google Scholar 

  7. Hopfenberg HB (1976) In: Paul DR, Harris FW (eds) Controlled release polymeric formulations, American Chemical Society, Washington DC, p 26

    Google Scholar 

  8. Cordes EH, Bull HG (1974) Chem Revs 74: 581

    Article  Google Scholar 

  9. Bronstead JN, Wynne-Jones WFK (1929) Trans Farad Soc 25: 59

    Article  Google Scholar 

  10. Choi NS, Heller J (1978) US Patent 4,079,038

    Google Scholar 

  11. Choi NS, Heller J (1978) US Patent 4,093,709

    Google Scholar 

  12. Choi NS, Heller J (1978) US Patent 4,131,648

    Google Scholar 

  13. Choi NS, Heller J (1979) US Patent 4,138,344

    Google Scholar 

  14. Choi NS, Heller J (1979) US Patent 4,180,646

    Google Scholar 

  15. DiVincenzo GD, Ziegler DA (1980) Toxicol Appl Pharmacol 52: 10

    Article  PubMed  Google Scholar 

  16. Roth RH, Giarman NJ (1966) Biochem Pharmacol 15: 1333

    Article  Google Scholar 

  17. Capozza RC, Sendelbeck SL, Balkenhol WJ In: Kostelnik RJ (ed) Polymeric delivery systems, Gordon and Breach, New York, p 59

    Google Scholar 

  18. Gabelnick HL (1983) In: Mishell Jr DR (ed) Long-acting contraception, Raven, New York, p 149

    Google Scholar 

  19. 10th Annual World Health Organization Report (1981) p 62

    Google Scholar 

  20. 11th Annual World Health Organization Report (1982) p 61

    Google Scholar 

  21. Vistness LM, Schmitt EE, Ksander GA, Rose EH, Balkenhol WJ, Coleman CL (1976) Surgery, 79: 690

    PubMed  Google Scholar 

  22. Scheeren JW, Aben RW (1974) Tetrahedron Letters 12: 1019

    Article  Google Scholar 

  23. Yasnitskii BG, Sarkisyants SA, Ivanyua EG (1946) Zhurnal Obshchei Khimii 34: 1940

    Google Scholar 

  24. Heller J, Penhale DWH, Helwing RF (1980) J Polymer Sci, Polymer Letters Ed, 18: 82

    Google Scholar 

  25. Heller J, Fritzinger BK, Penhale DWH, Ng SY, Helwing RF (1985) J Controlled Release 1: 225

    Article  Google Scholar 

  26. Heller J, Penhale DWH, Fritzinger BK, Rose JE, Helwing RF (1983) Contracept Deliv Syst 4: 43

    PubMed  Google Scholar 

  27. Heller J, Fritzinger BK, Penhale DWH, Ng SY, Helwing RF (1985) J Controlled Release 1: 233

    Article  Google Scholar 

  28. Heller, J, Ng SY, Penhale DWH, Fritizinger BK, Sanders LM, Burns RA, Gaynon MG, Bhosale SS (1987) J Controlled Release 6: 217

    Article  Google Scholar 

  29. Heller J (1985) J Controlled Release 2: 167

    Article  Google Scholar 

  30. Nguyen TH, Himmelstein KJ, Higuchi T (1985) Int J Pharmaceutics 25: 1

    Article  Google Scholar 

  31. Shih C, Himmelstein KJ (1984) Biomaterials 5: 237

    Article  PubMed  Google Scholar 

  32. Sparer RV, Shih C, Ringeisen CD, Himmelstein KJ (1984) J Controlled Release 1: 23

    Article  Google Scholar 

  33. Thombre AG, Himmelstein KJ (1985) AIChE J 35: 759

    Article  Google Scholar 

  34. Joshi A, Himmelstein KJ (1991) J Controlled Release 15: 95

    Article  Google Scholar 

  35. Dott D, Roskos KV, Ng SY, Heller J, Duncan R (work in progress)

    Google Scholar 

  36. Heller J, Penhale DWH, Fritzinger BK, Ng SY (1987) J Controlled Release 5: 173

    Article  Google Scholar 

  37. Unger RH (1982) Diabetes 31: 479

    PubMed  Google Scholar 

  38. Heller J, Chang AC, Rodd G, Grodsky GM (1990) J Controlled Release 13: 295

    Article  Google Scholar 

  39. Franson NM, Heller J (unpublished results)

    Google Scholar 

  40. Soloway MS (1977) Cancer Res 37: 2918

    PubMed  Google Scholar 

  41. Gressel MG, Parrish RK, Folberg R (1984) Ophthalmology 91: 378

    PubMed  Google Scholar 

  42. Maa YF, Heller J (1990) J Controlled Release 13: 11

    Article  Google Scholar 

  43. Heller J, Maa YF, Wuthrich P, Ng SY, Duncan R (1991) J Controlled Release 16: 3

    Article  Google Scholar 

  44. Martin WR, Jasinski DR, Mansky PA (1973) Arch Gen Psychiatry 28: 784

    PubMed  Google Scholar 

  45. Chiang CN, Hollister LE, Kishimoto A, Barnett G (1984) Clin Pharmacol Ther 36: 704

    PubMed  Google Scholar 

  46. Maa YF, Heller J (1990) J Controlled Release 14: 21

    Article  Google Scholar 

  47. Heller J, Penhale DWH, Helwing RF, Fritzinger BK (1981) Polymer Eng and Sci 21: 727

    Article  Google Scholar 

  48. Heller J (1986) In: Chielini E, Giusti P, Migliaresi C, Nicolais L (eds) Polymers in medicine II, Plenum, New York, p 357

    Google Scholar 

  49. Heller J, Ng SY, Fritzinger BK, Roskos KV (1990) Biomaterials 11: 235

    Article  PubMed  Google Scholar 

  50. Wuthrich P, Ng SY, Firitzinger BK, Roskos KV, Heller J (1992) J Controlled Release 21: 191

    Article  Google Scholar 

  51. Heller J, Maa YF, Wuthrich P, Ng SY, Duncan R (1991) J Controlled Release 16: 3

    Article  Google Scholar 

  52. Chiang Y, Kresge AJ, Salomaa P, Young CI (1974) J Am Chem Soc 96: 4494

    Article  Google Scholar 

  53. Shepp DH, Dandliker PS, deMiranda P, Burnette TC, Cederberg DM, Kirk LE, Meyers JD (1985) Ann Intern Med 103: 368

    PubMed  Google Scholar 

  54. Wuthrich P, Gaynon MG, Heller J (Unpublished results)

    Google Scholar 

  55. Wuthrich P, Heller J (Unpublished results)

    Google Scholar 

  56. Ng SY, Heller J (Unpublished results)

    Google Scholar 

  57. Shugar D (1950) Biochim Biophys Acta 8: 302

    Article  Google Scholar 

  58. Heller J, Ng SY, Fritzinger BK (1992) Macromolecules 25: 3362

    Article  Google Scholar 

  59. Bunton CA, DeWolfe RH (1965) J Org Chem 30: 1371

    Google Scholar 

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Robert S. Langer Nicholas A. Peppas

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© 1993 Springer-Verlag

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Heller, J. (1993). Poly (ortho esters). In: Langer, R.S., Peppas, N.A. (eds) Biopolymers I. Advances in Polymer Science, vol 107. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0027551

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  • DOI: https://doi.org/10.1007/BFb0027551

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-56148-4

  • Online ISBN: 978-3-540-47478-4

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