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.
Preview
Unable to display preview. Download preview PDF.
5 References
Heller J, Baker RW, Gale RM, Rodin JO (1978) J Appl Polymer Sci 22: 1991
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
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
Lappas LC, McKeehan WJ (1962) J Pharm Sci 51: 108
Lappas LC, McKeehan WJ (1965) J Pharm Sci 54: 176
Lappas LC, McKeehan WJ (1965) J Pharm Sci 56: 1257
Hopfenberg HB (1976) In: Paul DR, Harris FW (eds) Controlled release polymeric formulations, American Chemical Society, Washington DC, p 26
Cordes EH, Bull HG (1974) Chem Revs 74: 581
Bronstead JN, Wynne-Jones WFK (1929) Trans Farad Soc 25: 59
Choi NS, Heller J (1978) US Patent 4,079,038
Choi NS, Heller J (1978) US Patent 4,093,709
Choi NS, Heller J (1978) US Patent 4,131,648
Choi NS, Heller J (1979) US Patent 4,138,344
Choi NS, Heller J (1979) US Patent 4,180,646
DiVincenzo GD, Ziegler DA (1980) Toxicol Appl Pharmacol 52: 10
Roth RH, Giarman NJ (1966) Biochem Pharmacol 15: 1333
Capozza RC, Sendelbeck SL, Balkenhol WJ In: Kostelnik RJ (ed) Polymeric delivery systems, Gordon and Breach, New York, p 59
Gabelnick HL (1983) In: Mishell Jr DR (ed) Long-acting contraception, Raven, New York, p 149
10th Annual World Health Organization Report (1981) p 62
11th Annual World Health Organization Report (1982) p 61
Vistness LM, Schmitt EE, Ksander GA, Rose EH, Balkenhol WJ, Coleman CL (1976) Surgery, 79: 690
Scheeren JW, Aben RW (1974) Tetrahedron Letters 12: 1019
Yasnitskii BG, Sarkisyants SA, Ivanyua EG (1946) Zhurnal Obshchei Khimii 34: 1940
Heller J, Penhale DWH, Helwing RF (1980) J Polymer Sci, Polymer Letters Ed, 18: 82
Heller J, Fritzinger BK, Penhale DWH, Ng SY, Helwing RF (1985) J Controlled Release 1: 225
Heller J, Penhale DWH, Fritzinger BK, Rose JE, Helwing RF (1983) Contracept Deliv Syst 4: 43
Heller J, Fritzinger BK, Penhale DWH, Ng SY, Helwing RF (1985) J Controlled Release 1: 233
Heller, J, Ng SY, Penhale DWH, Fritizinger BK, Sanders LM, Burns RA, Gaynon MG, Bhosale SS (1987) J Controlled Release 6: 217
Heller J (1985) J Controlled Release 2: 167
Nguyen TH, Himmelstein KJ, Higuchi T (1985) Int J Pharmaceutics 25: 1
Shih C, Himmelstein KJ (1984) Biomaterials 5: 237
Sparer RV, Shih C, Ringeisen CD, Himmelstein KJ (1984) J Controlled Release 1: 23
Thombre AG, Himmelstein KJ (1985) AIChE J 35: 759
Joshi A, Himmelstein KJ (1991) J Controlled Release 15: 95
Dott D, Roskos KV, Ng SY, Heller J, Duncan R (work in progress)
Heller J, Penhale DWH, Fritzinger BK, Ng SY (1987) J Controlled Release 5: 173
Unger RH (1982) Diabetes 31: 479
Heller J, Chang AC, Rodd G, Grodsky GM (1990) J Controlled Release 13: 295
Franson NM, Heller J (unpublished results)
Soloway MS (1977) Cancer Res 37: 2918
Gressel MG, Parrish RK, Folberg R (1984) Ophthalmology 91: 378
Maa YF, Heller J (1990) J Controlled Release 13: 11
Heller J, Maa YF, Wuthrich P, Ng SY, Duncan R (1991) J Controlled Release 16: 3
Martin WR, Jasinski DR, Mansky PA (1973) Arch Gen Psychiatry 28: 784
Chiang CN, Hollister LE, Kishimoto A, Barnett G (1984) Clin Pharmacol Ther 36: 704
Maa YF, Heller J (1990) J Controlled Release 14: 21
Heller J, Penhale DWH, Helwing RF, Fritzinger BK (1981) Polymer Eng and Sci 21: 727
Heller J (1986) In: Chielini E, Giusti P, Migliaresi C, Nicolais L (eds) Polymers in medicine II, Plenum, New York, p 357
Heller J, Ng SY, Fritzinger BK, Roskos KV (1990) Biomaterials 11: 235
Wuthrich P, Ng SY, Firitzinger BK, Roskos KV, Heller J (1992) J Controlled Release 21: 191
Heller J, Maa YF, Wuthrich P, Ng SY, Duncan R (1991) J Controlled Release 16: 3
Chiang Y, Kresge AJ, Salomaa P, Young CI (1974) J Am Chem Soc 96: 4494
Shepp DH, Dandliker PS, deMiranda P, Burnette TC, Cederberg DM, Kirk LE, Meyers JD (1985) Ann Intern Med 103: 368
Wuthrich P, Gaynon MG, Heller J (Unpublished results)
Wuthrich P, Heller J (Unpublished results)
Ng SY, Heller J (Unpublished results)
Shugar D (1950) Biochim Biophys Acta 8: 302
Heller J, Ng SY, Fritzinger BK (1992) Macromolecules 25: 3362
Bunton CA, DeWolfe RH (1965) J Org Chem 30: 1371
Author information
Authors and Affiliations
Editor information
Rights and permissions
Copyright information
© 1993 Springer-Verlag
About this paper
Cite this paper
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
Download citation
DOI: https://doi.org/10.1007/BFb0027551
Received:
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-56148-4
Online ISBN: 978-3-540-47478-4
eBook Packages: Springer Book Archive