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(12) United States Patent (10) Patent No.: US 8,802,892 B2 Bezwada (45) Date of Patent: * Aug

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(12) United States Patent (10) Patent No.: US 8,802,892 B2 Bezwada (45) Date of Patent: * Aug USOO8802892B2 (12) United States Patent (10) Patent No.: US 8,802,892 B2 BeZWada (45) Date of Patent: * Aug. 12, 2014 (54) FUNCTIONALIZED PHENOLIC (52) U.S. Cl. COMPOUNDS AND POLYMERS CPC ................. C08G 69/44 (2013.01); A61L 27/18 THEREFROM (2013.01); C07D 3II/36 (2013.01); C07C 69/734 (2013.01); C07C 65/24 (2013.01); (71) Applicant: Bezwada Biomedical, LLC, C08G 69/40 (2013.01); A61L 31/04 (2013.01); Hillsborough, NJ (US) C07C 65/21 (2013.01); C07D493/04 (2013.01); A61L 31/10 (2013.01); A23L 1/3002 (72) Inventor: Rao S Bezwada, Hillsborough, NJ (US) (2013.01); A23L 1/30 (2013.01); C07D 31 1/16 (73) Assignee: Bezwada Biomedical, LLC, (2013.01); A61K 2800/522 (2013.01); C07C Hillsborough, NJ (US) 69/732 (2013.01); A61 K8/37 (2013.01); C08G 63/66 (2013.01); C07C2 17/84 (2013.01); (*) Notice: Subject to any disclaimer, the term of this C07C233/25 (2013.01); C07C 69/712 patent is extended or adjusted under 35 (2013.01); A23L I/058 (2013.01); C07C233/18 U.S.C. 154(b) by 0 days. (2013.01); C07C 69/92 (2013.01); C07D 3 II/I2 (2013.01); A61O 19/08 (2013.01); This patent is Subject to a terminal dis C07C 205/37 (2013.01); A61O 19/00 (2013.01) claimer. USPC ............... 562/405:562/490; 562/493: 560/8: Appl. No.: 13/654,068 560/67; 560/70; 560/75; 560/85 (21) (58) Field of Classification Search (22) Filed: Oct. 17, 2012 CPC ........ C07C 15/04; C07C 15/24: CO7C 15/18; C07C 15/58; C07C 43/257; CO7C 43/263; (65) Prior Publication Data C07C 43/267; CO7C 43/275 USPC .............. 560/8, 67, 70, 75, 85; 562/405, 490, US 2013/0281652 A1 Oct. 24, 2013 562/493 See application file for complete search history. Related U.S. Application Data (56) References Cited (63) Continuation of application No. 12/089,101, filed as U.S. PATENT DOCUMENTS application No. PCT/US2006/060002 on Oct. 16, 2006, now Pat. No. 8,318,973. 3,044.942 A 7/1962 Baptist 3,297.033 A 1/1967 Schmitt (60) Provisional application No. 60/728,823, filed on Oct. 21, 2005. (Continued) (51) Int. C. FOREIGN PATENT DOCUMENTS CD7C 63/04 (2006.01) WO 97.39.738 10, 1997 CD7C 63/06 (2006.01) WO 98.36013 8, 1998 CD7C 43/02 (2006.01) A6L27/8 (2006.01) (Continued) CO7D 3II/36 (2006.01) OTHER PUBLICATIONS C07C 69/734 (2006.01) CD7C 65/24 (2006.01) Gao et al. (J. Med. Chem. Published 2001, 3320-3328).* C08G 69/40 (2006.01) (Continued) A6IL 3L/04 (2006.01) CD7C 65/2 (2006.01) Primary Examiner — Richard Schnizer CO7D 49.3/04 (2006.01) Assistant Examiner — Alma Pipic A6IL 3 L/10 (2006.01) (74) Attorney, Agent, or Firm — Vance Intellectual Property, A2.3L I/30 (2006.01) PC CO7D 3II/6 (2006.01) C08G 69/44 (2006.01) (57) ABSTRACT C07C 69/732 (2006.01) A6 IK S/37 (2006.01) The present invention relates to compounds of formula I, C08G 63/66 (2006.01) which are functionalized phenolic compounds, and polymers C07C 21 7/84 (2006.01) formed from the same. C07C 233/25 (2006.01) C07C 69/712 (2006.01) A2.3L. I./058 (2006.01) Polymers formed from the functionalized phenolics are CD7C233/18 (2006.01) expected to have controllable degradation profiles, enabling C07C 69/92 (2006.01) them to release an active component over a desired time CO7D 3L/2 (2006.01) range. The polymers are also expected to be useful in a variety A61O 19/08 (2006.01) of medical applications. C07C 205/37 (2006.01) A61O 19/00 (2006.01) 13 Claims, No Drawings US 8,802,892 B2 Page 2 (56) References Cited 2005.0245736 A1 11/2005 Oreste 2006, OO13851 A1 1/2006 Giroux U.S. PATENT DOCUMENTS 2010.0113592 A1 5, 2010 Bezwada 3,371,069 2, 1968 Miyamae FOREIGN PATENT DOCUMENTS 3,531,561 9, 1970 Trehu 3,636,956 1, 1972 Schneider WO 99.12990 3, 1999 3,773.737 11, 1973 Goodman WO 99.29885 6, 1999 4,052.988 10, 1977 Doddi WO O1/41753 6, 2001 4,130,639 12, 1978 Shalaby WO O2/O9767 2, 2002 4,532,928 8, 1985 Bezwada WO O2/O9768 2, 2002 4,605,730 8, 1986 Shalaby WO WO 03/048226 A3 * 6, 2003 4,653,497 3, 1987 Bezwada WO 2004/008101 1, 2004 4,689,424 8, 1987 Shalaby WO 2006/052790 5, 2006 4,829,099 5, 1989 Fuller WO 2007/030464 3, 2007 4,886,870 12, 1989 D'Amore WO 2007/030538 3, 2007 4,938,949 7, 1990 Borch 5,082,925 1, 1992 Shalaby OTHER PUBLICATIONS 5,099,060 3, 1992 Kohn 5,264,540 11, 1993 Cooper Kaufmann et al. (Nature, vol. 203, p. 520, Published Aug. 1964).* 5,521,431 5, 1996 Tahara SciFinder Scholar Report on Kaufmann reference (2 pages, accessed 5,637,755 6, 1997 Nagumo on Oct. 13, 2013).* 5,759,830 6, 1998 Vacanti J. Org. Chem, 1959, 24, 523-526. 5,801,033 9, 1998 Hubbell Gutowska et al. J. Biomater Res., 29, 811-21 (1995). 5,834,274 11, 1998 Hubbell Hoffman, J. Controlled Release, 6, 297-305 (1987). 5,834,513 11, 1998 Ptchelintsev Mikos et al. Biomaterials, 14, 323-329 (1993). 5,843,743 12, 1998 Hubbell Helder et al., J. Biomed. Mater. Res., (24), 1005-1020 (1990). 5,895,150 4, 1999 Watabe Barrera et al., Macromolecules, (28), 425-432 (1995). 5,902,599 5, 1999 Anseth Langer, R., Science 249: 1527-33 (1990). 5,932,229 8, 1999 PtchelintSet Van Dijk-Wolthuis, W.N.W. et al., “Degradation and Release Behav 5,942,252 8, 1999 Tice ior of Dextran-Based Hydrogels.” Macromolecules, 30: 4639-45 5,951,997 9, 1999 Bezwada 6,468,519 10, 2002 Uhrich (1997). 6,689,350 2, 2004 Uhrich Van Dijk-Wolthuis, W.N.W. et al., “A new class of polymerizable 6,773,721 8, 2004 Wong dextrans with hydrolysable groups: hydroxyethyl methacrylated 6,861,068 3, 2005 dextran with and without oligolactate spacer.” Polymer 39(25); 6235 6,869,615 3, 2005 42 (1997). 6,887,974 5/2005 Kurisawa, et al., Macromol. Chem. Phys. 199,705-9 (1998). 6,890,561 5/2005 Heller, J. et al., “Controlled release of water-soluble macromolecules 7,671,168 3, 2010 BeZWada ............... 528,272 from bioerodible hydrogels.” Biomaterials 4; 262-6 (1983). 3, 2011 BeZwada .... 528,272 7,902,319 Brondsted, H. et al., “Hydrogels for site-specific oral drug delivery: 7,935,843 5, 2011 BeZwada .... ... 560/40 synthesis and characterization.” Biomaterials 12; 584-92 (1991). 8,309,754 11, 2012 BeZwada .... 560/37 Ulbrich, K. et al., “Novel biodegradable hydrogelsprepared using the 8,318,973 11, 2012 BeZwada .... 562/405 divinylic crosslinking agent N.O-dimethacryloylhydroxylamine 1. 8.436,201 5, 2013 BeZWada ............... 560, 18O 2002fO169275 11, 2002 Matsuda Synthesis and characterization of rates of gel degradation and rate of 2003/O158598 8, 2003 Ashton release of model drugs, in vitro and in vivo.” J. Control. Release 24: 2003/0216307 11, 2003 Kohn 181-90 (1993). 2003/0232091 12, 2003 Shefer Trenor, “Synthesis and characterization of tailored photoactive mac 2004/0096476 5, 2004 Uhrich romolecules.” Apr. 16, 2004. Abstract p. 1, 5-7. 2004/01 17007 6, 2004 Whitbourne Vlasenko et al., Pharmaceutical Chemistry Journal 1993,27(9), 648 2005, 004.8121 3, 2005 East 51. 2005/OO74493 4, 2005 Mehta Canceill et al., Helvetica Chimica Acta 1982, 65 (Fasc. 6, Nr. 185), 2005/OO953OO 5/2005 Wynn 1894-97. 2005, 0112171 5/2005 Tang Vermerris et al., Phenolic Compound Biochemistry, 2008, p. 1. 2005/O152958 7/2005 Cordes 2005/0238689 10, 2005 Carpenter * cited by examiner US 8,802,892 B2 1. 2 FUNCTIONALIZED PHENOLIC DETAILED DESCRIPTION OF THE PRESENT COMPOUNDS AND POLYMERS INVENTION THEREFROM The present invention provides novel functionalized phe FIELD OF THE INVENTION 5 nolic compounds and absorbable polymers derived from them. The present invention is designed to extend the useful The present invention relates to the discovery of function ness of phenolic compounds while retaining their inherent alized phenolic compounds and polymers derived therefrom, biological properties. The phenolic compounds are function which can have controllable degradation profiles. alized with safe and biocompatible molecules (e.g., glycolic 10 acid, lactic acid, caprolactone, and dioxanone). The novel BACKGROUND OF THE INVENTION functionalized phenolic compounds of the present invention are expected to have controllable hydrolysis profiles, improved bioavailability, improved efficacy, and enhanced There are a vast number of known phenolic compounds or functionality. phenolics (e.g., flavonoids) with a variety of known beneficial 15 Some of the functionalized phenolic compounds of the uses. Phenolic and polyphenolic compounds are found present invention can be monomers from which polymers can widely in nature: in cereals, legumes, nuts, oilseeds, plant be made that are useful for medical applications. For oils, fruits, vegetables, tea, coffee, cocoa, beer, wine, herbal example, a phenolic compound can be functionalized to form products, such as Echinacea, ginseng, gingko biloba, St. functionalized monomers that can then be polymerized to John's wort, Valerian, hawthorne, ginger, licorice, milk form absorbable polymers (e.g., polyesters, polyamides, thistle, goldenseal, devil's claw, black cohosh, saw palmetto, polyester amides, polyurethanes, and polyanhydrides). It can and kavakava, for example. These substances are essential for be advantageous for the monomers that are to be polymerized growth and reproduction of plants and serve as antifeedants to have at least two active sites (e.g., 2 or 3) for polymeriza and antipathogens, among other purposes.
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