2
`
`In the Specification
`
`Docket No. UF.572XC1
`
`Serial No. 12/664,172
`
`Please amend the paragraphs found on page 7, lines 31-32 continuing through page 8, line 4
`
`of the specification as follows:
`
`Figure 19 shows the chemical structure of a monomer for the preparation of a polymer ofthe
`
`invention, wherein the biologically active molecule is an antibiotic.
`
`Figure 20 shows the chemical structure of a monomer for the preparation ofa polymer of the
`
`invention, wherein the biologically active molecule is an analgesic.
`
`Figure 21 shows the chemical structure of a monomer for the preparation of a polymer ofthe
`
`invention, wherein the biologically active molecule is an antibacterial compound.
`
`Please amend the paragraphs found on page 34, lines 6—24 of the specification as follows:
`
`(S)=2—(undec~10»enyl)tridec~12—enyl 2—(4—isobutylphenyl)propanoate. The pure product
`
`(shown in Figure 8) was obtained ing/oyieldafter purification using flash chromatography using 14:1
`
`(hexanezethyl acetate) mobile phase. 1H NMR (300 MHZ, CDC13)I 5 .88 (d, 6H), 1.14—1.40 (m, b,
`
`32H), 1.47 (d, 3H), 1.54 (b, 1H), 1.83 (m, 1H), 2.03 (q, 4H), 2.42 (d, 2H), 3.67 (q, 1H), 3.94 (0, 2H),
`
`4.93 (m, 4H), 5.80 (m, 2H), 7.06 (d, 2H), 7.18 (d, 2H). 13C NMR (75 MHz,CDC13):5 18.44, 22.59,
`
`26.84, 26.87, 29.18, 29.38, 29.73, 29.79, 29.81, 30.14, 30.39, 31.34, 31.44, 34.03, 37.53, 45.28,
`
`45.52, 67.44,114.31,127.40,129.42,138.13,139.41,140.57,175.03. EI/HRMS [M +1]: calcd for
`
`C37H6202, 539.4823 g/mol; found, 539.4809 g/mol.
`
`(S)—2-(undec—10-enyl)tridec-12—enyl 2~(6—methoxynapthflalen—2—yl)propanoate. The pure
`
`product (shown in Figure 9) was obtained Weld—after purification using flash chromatography
`
`using 14:1 (hexanezethyl acetate) mobile phase. 1H NMR (300 MHz, CDCl3): 8 1.17-1.40 (br, 33H),
`
`1.57 (d, 3H), 2.02 (m, 4H), 3.83 (q, 1H), 3.89 (s, 3H), 3.97 (m, 2H), 4.94 (in, 4H), 5.80 (m, 2H),
`
`7.08-7.13 (m, 2H), 7.39 (m, 1H), 7.66 (m, 3H).
`
`13C NMR (75 MHz, CDC13)I 5 14.39, 18.45, 26.81,
`
`26.87, 29.15, 29.35, 29.68, 29.73, 29.77, 30.09, 31.38, 31.47, 34.02, 37.52, 45.82, 55.43, 60.55,
`
`67.62, 105.76, 114.30, 119.09, 126.12, 126.50, 127.21, 129.15, 129.43, 133.88, 136.04, 139.40,
`
`157.80, 174.92. El/HRMS [M +1]: calcd for C33H5803, 563.4459 g/mol; found, 563.4466 g/mol.
`
`J:\UF\572XC1\Amend\Amend.doc\ps
`
`
`
`In the Specification
`
`Docket No. UF.572XC1
`
`Serial No. 12/664,172
`
`Please amend the paragraphs found on page 7, lines 31-32 continuing through page 8, line 4
`
`of the specification as follows:
`
`Figure 19 shows the chemical structure of a monomer for the preparation of a polymer ofthe
`
`invention, wherein the biologically active molecule is an antibiotic.
`
`Figure 20 shows the chemical structure of a monomer for the preparation ofa polymer of the
`
`invention, wherein the biologically active molecule is an analgesic.
`
`Figure 21 shows the chemical structure of a monomer for the preparation of a polymer ofthe
`
`invention, wherein the biologically active molecule is an antibacterial compound.
`
`Please amend the paragraphs found on page 34, lines 6—24 of the specification as follows:
`
`(S)=2—(undec~10»enyl)tridec~12—enyl 2—(4—isobutylphenyl)propanoate. The pure product
`
`(shown in Figure 8) was obtained ing/oyieldafter purification using flash chromatography using 14:1
`
`(hexanezethyl acetate) mobile phase. 1H NMR (300 MHZ, CDC13)I 5 .88 (d, 6H), 1.14—1.40 (m, b,
`
`32H), 1.47 (d, 3H), 1.54 (b, 1H), 1.83 (m, 1H), 2.03 (q, 4H), 2.42 (d, 2H), 3.67 (q, 1H), 3.94 (0, 2H),
`
`4.93 (m, 4H), 5.80 (m, 2H), 7.06 (d, 2H), 7.18 (d, 2H). 13C NMR (75 MHz,CDC13):5 18.44, 22.59,
`
`26.84, 26.87, 29.18, 29.38, 29.73, 29.79, 29.81, 30.14, 30.39, 31.34, 31.44, 34.03, 37.53, 45.28,
`
`45.52, 67.44,114.31,127.40,129.42,138.13,139.41,140.57,175.03. EI/HRMS [M +1]: calcd for
`
`C37H6202, 539.4823 g/mol; found, 539.4809 g/mol.
`
`(S)—2-(undec—10-enyl)tridec-12—enyl 2~(6—methoxynapthflalen—2—yl)propanoate. The pure
`
`product (shown in Figure 9) was obtained Weld—after purification using flash chromatography
`
`using 14:1 (hexanezethyl acetate) mobile phase. 1H NMR (300 MHz, CDCl3): 8 1.17-1.40 (br, 33H),
`
`1.57 (d, 3H), 2.02 (m, 4H), 3.83 (q, 1H), 3.89 (s, 3H), 3.97 (m, 2H), 4.94 (in, 4H), 5.80 (m, 2H),
`
`7.08-7.13 (m, 2H), 7.39 (m, 1H), 7.66 (m, 3H).
`
`13C NMR (75 MHz, CDC13)I 5 14.39, 18.45, 26.81,
`
`26.87, 29.15, 29.35, 29.68, 29.73, 29.77, 30.09, 31.38, 31.47, 34.02, 37.52, 45.82, 55.43, 60.55,
`
`67.62, 105.76, 114.30, 119.09, 126.12, 126.50, 127.21, 129.15, 129.43, 133.88, 136.04, 139.40,
`
`157.80, 174.92. El/HRMS [M +1]: calcd for C33H5803, 563.4459 g/mol; found, 563.4466 g/mol.
`
`J:\UF\572XC1\Amend\Amend.doc\ps
`
`
`
`Serial No. 12/664,172
`Please amend the paragraphs found on page 35, lines 5—32, continuing to page 36, lines
`1—3, of the specification as follows:
`
`3
`
`Docket No. UF.572XC1
`
`(S)—2—(2~(2-(2~hydroxyethoxy)eth0xy)ethoxy)ethyl 2-(4—isobutylphenyl)propanoate.
`
`The pure
`
`product (shown in Figure 10) was obtained l'rizi—Qérfyzielei—after purification using flash chromatography
`
`using 14:1 (hexanezethyl acetate) mobile phase. 1H NMR (300 MHZ, CDC13)Z 8 .90 (d, 6H), 1.49 (d,
`
`3H), 1.84 (m, 1H), 2.43 (d, 2H), 2.66 (s, 1H), 3.50—3.80 (m, br, 15H), 4.22 (m, 2H), 7.08 (d, 2H),
`
`7.20 (d, 2H). 13C NMR (75 MHZ, CDC13): 5 .14, 18.70, 22.53, 30.32, 45.14, 45.16, 61.86, 64.01,
`
`69.22, 70.49, 70.68, 70.69, 70.77, 72.65, 127.34, 129.42, 137.82, 140.62, 174.84. El/HRMS [M +1]:
`
`calcd for C21H3406, 383.2482 g/mol; found, 383.2481 g/mol.
`
`(S)—10—hydroxydecyl 2—(4—isobutylphenyl)propanoate. The pure product (shown in Figure 1 1)
`
`was obtained in~944yield4after purification using flash chromatography using 14:1 (hexane:ethyl
`
`acetate) mobile phase. 1H NMR (300 MHZ, CDC13): 5 .87 (d, 611), 120—1130 (br, 12H), 1.46 (d,
`
`3H), 1.54 (m, 4H), 1.82 (m, 2H), 2.02 (s, 1H), 2.42 (d, 2H), 3.60 (t, 2H), 3.65 (q, 1H), 4.03 (t, 2H),
`
`7.06 (d, 2H), 7.18 (d, 2H). 13C NMR (75 MHz, CDC13): 5 18.59, 22.52, 25.89, 28.66, 29.27, 29.54,
`
`29.62, 30.31, 32.91, 45.19, 45.36, 63.08, 64.90, 127.29,129.39, 138.05, 140.54, 174.99.
`
`(S)—2—(2—(2—(2—hydroxyethoxy)ethoxy)ethoxy)ethy1 2—(6-methoxynaphthalen—2—y1)propanoate.
`
`The pure product (shown in Figure 12) was obtained infiO/o—yield—after purification using flash
`
`chromatography using 14: 1 (hexanezethyl acetate) mobile phase. 1H NMR (3 00 MHZ, CDC13): 6 1.57
`
`(d, 3H), 2.67 (s,br, 1H), 3.48-3.88 (1n, br, 14H), 3.88 (q, 1H), 3.89 (s, 3H), 4.23 (t, 2H), 7.11 (d,1H),
`
`7.15 (d, 1H), 7.40 (d, 1H), 7.43 (d, 1H), 7.67 (s, 1H), 7.71 (s, 1H) 13C NMR (75 MHZ, CDC13): 8
`
`.12, 18.64, 45.45, 55.40, 61.81, 64.08, 69.14, 70.40, 70.56, 70.60, 70.66, 72.59, 105.67, 119.07,
`
`126.10, 126.40, 127.22, 129.03, 129.38, 133.80,135.75,157.74, 174.73. El/HRMS [M +1]: calcd
`
`for (322113007, 407.2064 g/mol; found, 407.2044 g/mol.
`
`(S)-10-hydroxydecyl2—(6-methoxynaphthalen-2—yl)pr0pan0ate. The pure product (shown in
`
`Figure 13) was obtained iné’4—yie1d—afier purification using flash chromatography using 14:1
`
`(hexanezethyl acetate) mobile phase. 1H NMR (300 MHZ, CDC13)I 8 1.12-1.30 (br, 12H), 1.42 (s,
`
`1H), 1.52 (m, 4H), 1.55 (d, 3H), 3.61 (t, 2H), 3.82 (q, 1H), 3.89 (s, 3H), 4.04 (t, 2H), 7.1 (s, 1H),
`
`7.13 (d, 1H), 7.38 (d, 1H), 7.65 (s, 1H), 7.66 (s, 1H), 7.69 (s, 1H) 13C NMR (75 MHZ, CDC13): 6
`
`18.70, 25.91, 25.98, 28.75, 29.33, 29.57, 29.64, 33.01, 45.76, 55.52, 63.27, 65.08,105.84, 119.11,
`
`J:\UF\572XC l\Amend\Amend.doc\ps
`
`
`
`126.12, 126.50, 127.27, 129.16, 129.48, 133.88, 136.09.
`
`4
`
`Docket No. UF.572XC1
`
`Serial No. 12/664,172
`
`Please amend the paragraphs found on page 36, lines 18-32, continuing to page 37, lines
`1-22, of the specification as follows:
`
`(S)—14-(4-isobuty1phcny1)—13—oxo-3,6,9,12—tetroxapentadecyl 2-(undec-10-eny1)tridec—12—
`
`enoate. The pure product (shown in Figure 14) was obtained in—Qleyieldafter purification using flash
`
`chromatography using 14: 1 (hexanezethyl acetate) mobile phase. 1H NMR (300 MHZ, CDC13): 8 .87
`
`(d, 6H), 1.20—1.60 (br, m, 34H), 1.82 (m, 1H), 1.98 (q, 4H), 2.31 (br, 1H), 2.41 (d, 2H), 3.50—3.75
`
`(br, m, 1311), 4.19 (m, 4H), 4.91 (m, 4H), 5.78 (m, 2H), 7.05 (d, 2H), 7.17 (d, 2H). 13C NMR (75
`
`MHZ, CDC13): 5 18.75, 22.57, 27.58, 29.12, 29.31, 29.65, 29.73, 29.75, 30.34, 32.59, 33.98, 45.22,
`
`45.81, 63.22, 64.03, 69.27, 69.48, 70.73, 70.76, 70.83, 114.29, 127.37, 129.45, 137.87, 139.37,
`
`140.65, 174.82, 176.65. EI/HRMS [M +1]: calcd for C45H76O7, 729.5664 g/mol; found, 729.5689
`
`g/mol.
`
`(S)-10—(2—(4-isobutylphenyl)propanoyloxy)decy1 2-(undec-10—eny1)tridec-12—enoate. The
`
`pure product (shown in Figure 15) was obtained Weld—after purification using flash
`
`chromatography using 14:1 (hexane:ethy1 acetate) mobile phase. 1H NMR (300 MHZ, CDC13)Z 5 .87
`
`(d, 6H), 1.20—1.65 (br, m, 51H), 1.82 (m, 1H), 2.01 (q, 4H), 2.28 (m, 1H), 2.42 (d, 2H), 3.65 (q, 1H),
`
`4.04 (q, 4H), 4.92 (m, 4H), 5.78 (m, 2H), 7.06 (d, 2H), 7.18 (d, 2H). 13’C NMR (75 MHZ, CDC13): 8
`
`18.66, 22.57, 25.97, 26.18, 27.67, 28.75, 28.94, 29.14, 29.33, 29.36, 29.43, 29.67, 29.72, 29.76,
`
`30.37, 32.75, 34.00, 45.25, 45.41, 46.05, 64.29, 64.91, 114.30, 127.34, 129.44, 138.12, 139.38,
`
`140.58, 174.96, 176.82. El/HRMS [M +1]: calcd for C47H3004, 709.6129 g/mol; found, 709.6111
`
`g/mol.
`
`(S)—14~(6-methoxynaphthalen-2-y1)—1 3 ~oxo—3,6,9,12-tetroxapentadecyl
`
`2-(undec—10-
`
`eny1)tridec-12—enoate. The pure product (shown in Figure 16) was obtained in——%4yielel—after
`
`purification using flash chromatography using 14:1 (hexanezethyl acetate) mobile phase. 1H NMR
`
`(300 MHZ, CDC13): 6 1.20-1.45 (br, m, 32H), 1.55 (d, 3H), 2.00 (q, 4H), 2.32 (m, 1H), 3.45—3.65 (in,
`
`br, 12H), 4.20 (q, 1H), 4.21 (s, 3H), 4.22 (m, 4H), 4.92 (m, 4H), 5.76 (m, 2H), 7.05-7.15 (m, 2H),
`
`7.38 (d, 1H), 7.67 (d, 3H). 13C NMR (75 MHZ, CDC13): 5 18.70, 27.55, 29.09, 29.28, 29.62, 29.69,
`
`29.72, 32.56, 33.95, 45.50, 45.78, 55.43, 63.19, 64.09, 69.20, 69.42, 70.65, 70.69, 70.71, 105.74,
`
`114.27, 119.10,126.13,126.41,127.25,129.08,129.41,133.85, 135.78,139.33,157.81,174.70,
`
`.1 :\UF\572XC 1\Amend\Aincnd.dOC\ps
`
`
`
`5
`
`Docket No. UF.572XC1
`
`Serial No. 12/664,172
`176.61. EI/HRMS [M +1]: calcd for C46H7203, 753.5300 g/mol; found, 753.5305 g/mol.
`
`(S)— 1 0—(2~(6-methoxynaphthalen-2—y1)propanoyioxy)decyl 2-(undec— 10~enyl)tridec- 1 2-enoate.
`
`The pure product (shown in Figure 17) was obtained in—%~yiei€1~after purification using flash
`
`chromatography using 14:1 (hexanezethyl acetate) mobile phase. 1H NMR (300 MHz, CDC13): 5
`
`1.15-1.65 (br, m, 50H), 1.99 (q, 4H), 2.29 (m, 1H), 3.82 (q, 1H), 3.89 (s, 3H), 4.04 (t, 4H), 4.94 (m,
`
`4H), 5.79 (m, 2H), 7.05—7.15 (m, 2H), 7.39 (d, 1H), 7.66 (d, 3H)
`
`13C NMR (75 MHZ, CDC13): 5
`
`18.69, 25.98, 26.14, 27.66, 28.74, 28.92, 29.13, 29.32, 29.40, 29.60, 29.66, 29.71, 29.75, 32.74,
`
`33.99, 45.72, 46.04, 55.45, 64.29, 65.03, 105.78, 114.29, 119.10, 126.09, 126.45, 127.24, 129.14,
`
`129.44, 133.86, 136.05, 139.38, 157.81, 174.87, 176.83._EI/HRMS [M +1]: calcd for C4gH7605,
`
`733.5766 g/mol; found, 733.5768 g/inol.
`
`J:\UF\572XC l\/\mend\Amend.doc\ps
`
`
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