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(12) Patent Application Publication (10) Pub. No.: US 2015/0259464 A1 Bezwada Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2015/0259464 A1 Bezwada Et Al US 20150259464A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0259464 A1 BeZWada et al. (43) Pub. Date: Sep. 17, 2015 (54) BIO-BASED MONOMERS AND POLYMERS C08G 7L/02 (2006.01) C08G 69/00 (2006.01) (71) Applicant: Bezwada Biomedical, LLC, C07C 225/22 (2006.01) Hillsborough, NJ (US) A69/70 (2006.01) (72) Inventors: Rao S. Bezwada, Hillsborough, NJ (52) U.S. Cl. (US); Neeti Srivastava, Hillsborough, CPC .......... C08G 18/7657 (2013.01); C07C 225/22 NJ (US) (2013.01); A61 K9/70 (2013.01); C08G 71/02 (21) Appl. No.: 14/645,522 (2013.01); C08G 69/00 (2013.01); C08G 73/02 (22) Filed1C Mara. 12,A 2015 (2013.01); C07C 2101/16 (2013.01) Related U.S. Application Data (57) ABSTRACT (60) Provisional application No. 61/951,617, filed on Mar. 12, 2014. Described are novel bio-based bioabsorbable/non-absorb Publication Classification able and biodegradable monomer compounds, bioabsorbable (51) Int. Cl. and biodegradable polymers therefrom, and methods of mak C08G 8/76 (2006.01) ing Such monomers and polymers, which are useful interalia C08G 73/02 (2006.01) as medical devices, implantable or otherwise. US 2015/0259464 A1 Sep. 17, 2015 BO-BASED MONOMERS AND POLYMERS able chemical versatility. While polyurethane polymers have certain useful properties, shaped articles based on these poly FIELD OF THE INVENTION mers are not typically absorbable or biodegradable and may therefore be unacceptable in circumstances that require 0001. The present invention relates to the discovery of a absorption or biodegradation. For example, certain biomedi new class of bio-based monomers and polymers. Using these cal applications, such as Surgical devices including but not bio-based monomers and their functionalized derivatives, limited to monofilament and multifilament Sutures, films, novel bio-based absorbable/biodegradable and non-absorb sheets, plates, clips, staples, pins, screws, stents, stent coat able polymers (or partially asborbable/biodegradable poly ings, and the like, generally require the use of a material that mers) can be prepared. is asborbable. Hence, the vast majority of research devoted to the development of biomedical polyurethanes has focused on BACKGROUND OF THE INVENTION long-term applications such as vascular grafts and pacemaker 0002 Bio-based and/or biodegradable polymers are lead insulators. increasingly being used in applications that currently rely on 0007. Despite progress in the general development of petroleum based feedstocks. These biobased and/or biode polyurethanes and similar polymers for use in biomedical gradable monomers and polymers have become increasingly applications, relatively little research have been directed to important for a variety of consumer products, durable goods developing absorbable polyurethanes for temporary, rather and biomedical applications including tissue engineering than longer-term implantation. See Fuller et al., U.S. Pat. No. scaffolds, Surgical adhesives, foams, medical device coatings 4,829,099: Beckmann et al., U.S. Patent Publication Nos. and drug delivery matrices, etc. They are also increasingly 2005/0013793, 2004/0170597, and 2007/0014755; Bruinet being used for disposable medical device applications. For al., PCT Publication No. WO95/26762; Woodhouse et al., example, isocyanate-based adhesive/sealant compositions U.S. Pat. No. 6,221.997: Cohn et al., U.S. Pat. No. 4,826,945, are described in U.S. Pat. Nos. 6,894,140; 5,173,301: 4,994, which generally discuss recent advances made in the field of 542; and, 4,740,534, the disclosures of which are incorpo absorbable polyurethanes. rated herein by reference in their entirety. 0008 Subsequent work by Bruin et al., PCT No. WO 0003 Polymers that are derived from monomers from 95/26762, describes the synthesis of crosslinked polyure renewable biobased sources are referred to as bio-based poly thane networks incorporating lactide or glycolide and e-ca mers. Polymers that breakdown into carbon dioxide, water prolactone joined by a lysine-based diisocyanate. Bruin dis and biomass from the action of naturally occurring microor closes that these polymers display good elastomeric ganism Such as bacteria, fungi etc over a period of time are properties and degrade within about 26 weeks in vitro and referred to as biodegradable polymers. A majority of the about 12 weeks in Vivo (Subcutaneous implantation in guinea biobased polymers are also biodegradable. Polymers that are pigs). Despite their disclosed desirable flexibility and degra designed to degrade under physiological conditions are dation characteristics, these highly crosslinked polymers are referred to as absorbable polymers. These polymers are not extensively used in Some biomedical applications because sometimes also referred to as, bioerodible, bioabsorbable, or in some cases they cannot be readily processed into Surgical hydrolyzable polymers. Synthetic absorbable polymers are articles, for example, using standard techniques such as solu generally classified into polyesters, polyorthoesters, polyan tion casting or melt processing, as is the case for the more hydrides, polyesteramides, and polyoxaesters. typical linear, segmented polyurethanes. 0004 Absorbable polymers are increasingly used in a 0009 Cohn et al., EP295055 describes a series of elasto wide range of biomedical applications including tissue engi meric polyester-polyether-polyurethane block copolymers neering scaffolds, stents, stent coatings, foams, highly porous intended for use as Surgical articles. However, these polymers foams, reticulated foams, and adhesion prevention barriers. may be relatively stiff and may have low tensile strength, This increased utilization is, in part, a function of the transient which may preclude their use as elastomeric biomaterials. nature of these polymers when used as biomedical implants Beckmann et al., U.S. Patent Publication No. 2005/0013793 or drug carriers. Medical devices made from absorbable poly describes polyurethane-based biodegradable adhesives from mers can mitigate the inevitable and usually negative physi multi-isocyanate functional molecules and multifunctional ologic responses (e.g., fibrous encapsulation), which limit precursor molecules with terminal groups selected from long-term device success. Hence, an array of asborbable hydroxyl and amino groups. Woodhouse et al. describes polymers have been developed and studied in various bio absorbable polyurethanes derived from amino acids. How medical applications. While significant research and devel ever, all these absorbable polyurethanes may suffer from one opment activity has been carried out on bioasborbable poly or more of the following drawbacks: (a) the very slow rate of mers, such polymers may suffer from performance formation of polyurethane that may be attributed to the low deficiencies which are typically not fully recognized until reactivity of the polyisocyanates and (b) the lack of tunable new applications are identified and in-use testing has been physical and/or mechanical properties and/or controllable carried out. hydrolytic degradation profiles for biodegradable polyisocy 0005 Of the synthetic asborbable polymers, polyesters anates or absorbable polyurethanes derived therefrom. find numerous applications in medical, Surgical and con 0010 Despite advancements in the art of producing poly trolled delivery applications and are the key components of a meric materials and methods for making polymers Suitable majority of bioasborbable medical devices, ranging from for use in drug delivery, tissue adhesives, adhesion prevention Sutures, staples, orthopedic screws and implantable Surgical barrier, foams, highly porous foams, reticulated foams, bone devices to tissue engineering scaffolds. wax formulations, stents, Stent coatings, scaffolds, films, 0006. In addition to polyesters, segmented polyurethane molded devices, and similar Surgical articles, presently avail elastomers have also enjoyed wide use as biomaterials gen able polymers generally lack adequate performance proper erally due to their excellent mechanical properties and desir ties desirable in Surgical articles, for example, those related to US 2015/0259464 A1 Sep. 17, 2015 bioabsorption, flex fatigue life, strength in use, flexibility, 0018. In an embodiment, the present invention provides a and/or durability. Thus, there continues to be a need for new novel class of bio-based monomers and materials derived devices and polymers having tunable physical and/or biologi therefrom (e.g., polymers, pre-polymers, polyols, and/or oli cal properties, so that medical devices and Surgical articles gomers). The bio-based materials may be biodegradable, having a variety of end uses can be prepared. absorbable, and/or non-absorbable. The bio-based monomers 0011. With more uses being envisioned for polymers and are derived from starting compounds that includebutane diol. an increased demand for absorbable polymers with new and Succinic acid, L-lactic acid, amino acids such as L-lysine, improved properties targeted to address performance defi castor oil-based monomers (e.g., ricinoleic acid, 12-hydroxy ciencies, there still is a need for bio-based monomers and Stearic acid, and sebacic acid), and Soybean oil-based mono polymers with beneficial properties. CS. 0019. In an embodiment, the present invention provides a SUMMARY OF THE INVENTION novel class of polymers formed by polymerizing a bio-based 0012. In an embodiment, the present invention provides a monomer with an appropriate additional monomer (e.g., a novel class of bio-based
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