JP2008094727A - レチノイドプロドラッグ化合物 - Google Patents
レチノイドプロドラッグ化合物 Download PDFInfo
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- 0 *c1ccc(C*c2c(*)c(*)c(*)c(*)c2*)cc1 Chemical compound *c1ccc(C*c2c(*)c(*)c(*)c(*)c2*)cc1 0.000 description 1
- IVDMAAALVGAJIM-UHFFFAOYSA-N CC(C)(CCC(C)(C)c1c2)c1ccc2C(Nc1ccc(CCC(O)=O)cc1)=O Chemical compound CC(C)(CCC(C)(C)c1c2)c1ccc2C(Nc1ccc(CCC(O)=O)cc1)=O IVDMAAALVGAJIM-UHFFFAOYSA-N 0.000 description 1
- SCQZLHALVQMRDV-UHFFFAOYSA-N CC(C)(CCC(C)(C)c1c2)c1ccc2C(Nc1ccc(CCC(OC)=O)cc1)=O Chemical compound CC(C)(CCC(C)(C)c1c2)c1ccc2C(Nc1ccc(CCC(OC)=O)cc1)=O SCQZLHALVQMRDV-UHFFFAOYSA-N 0.000 description 1
- JSQXJJLGTOMPIG-UHFFFAOYSA-N CC(C)(CCC(C)(C)c1c2)c1ccc2NC(c1ccc(CCC(O)=O)cc1)=O Chemical compound CC(C)(CCC(C)(C)c1c2)c1ccc2NC(c1ccc(CCC(O)=O)cc1)=O JSQXJJLGTOMPIG-UHFFFAOYSA-N 0.000 description 1
- GDIJOZPALJHMMA-UHFFFAOYSA-N CC(C)(CCC1(C)C)c(cc2)c1cc2NC(c1ccc(CCC(OC)=O)cc1)=O Chemical compound CC(C)(CCC1(C)C)c(cc2)c1cc2NC(c1ccc(CCC(OC)=O)cc1)=O GDIJOZPALJHMMA-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】 下記の一般式(I):
〔R1〜R5は水素原子、アルキル基、又はトリアルキルシリル基を示し、X は-NH-CO-、-CO-NH-、-N(COR6)-CO-、-CO-N(COR7)-(R6及びR7は低級アルコキシ基又はカルボキシ置換フェニル基を示す)などを示し;Zは-Y-CH(R12)-COOH又は-COOR13(Yは単結合、-CH2-、-CH(OH)-、-CO-、-CO-NH-、又は-CO-NH-CH2-CO-NH-を示し、R12は水素原子又は低級アルキル基を示し、R13は水素原子、-CH(R14)-COOH(R14は水素原子、低級アルキル基、又は水酸基を示す)、-[CH2CH2-O]n-CH2-CH2-OH、-CH2-O-[CH2CH2-O]m-CH2-OH、又は-[CH(CH3)-CO-O]p-CH(CH3)-COOH(n、m、又はpは1から100の整数を示す)を示す〕で表される化合物又はその塩、あるいはそのエステル。
【選択図】なし
Description
例1:2-[2-(2-ヒドロキシ)エトキシ]エチル 4-[(5,6,7,8-テトラヒドロ-5,5,8,8-テトラメチル-2-ナフチル)カルバモイル]ベンゾアート
無色微細針状晶、融点123.5-124.5℃ (ジクロロメタン−ヘキサン)
MS (m/z): 483 (M+, 15), 468 (21), 378 (4), 318 (13), 291 (7), 149 (15), 104 (16), 89 (9), 75 (8), 58 (8), 45 (100), 31 (14)
IR (KBr) cm-1: 1711, 1646
1H-NMR (CDCl3) δ: 1.28 (6H, s), 1.30 (6H, s), 1.69 (4H, s), 2.48 (1H, br s, OH), 3.58-3.64 (2H, m), 3.66-3.75 (6H, m), 3.84-3.89 (2H, m), 4.50-4.55 (2H, m), 7.31 (1H, d, J=8.5 Hz), 7.45 (1H, dd, J=8.5, 2.5 Hz), 7.55 (1H, d, J=2.5 Hz), 7.92 (2H, A 2B2, J=8 Hz), 7.94 (1H, br s, CONH), 8.15 (2H, A2 B 2, J=8 Hz).
無色ガラス状物質
MS (m/z): 615 (M+, 5), 600 (2), 378 (3), 362 (3), 334 (3), 318 (3), 291 (4), 193 (3), 149 (4), 133 (4), 104 (7), 89 (21), 45 (100)
IR (CHCl3) cm-1: 1713, 1669
1H-NMR (CDCl3) δ: 1.28 (6H, s), 1.30 (6H, s), 1.69 (4H, s), 2.28 (1H, br s, OH), 3.55-3.74 (20H, m), 3.82-3.88 (2H, m), 4.47-4.53 (2H, m), 7.30 (1H, d, J=8.5 Hz), 7.46 (1H, dd, J=8.5, 2.5 Hz), 7.57 (1H, d, J=2.5 Hz), 7.94 (2H, A 2B2, J=8 Hz), 8.14 (2H, A2B2, J=8 Hz), 8.20 (1H, br s, CONH).
無色飴状物質
MS (m/z): 703 (corresponding to octaethylene derivative, 0.3), 672 (0.3), 615 (0.3), 351 (24), 336 (100), 149 (68), 121 (23), 104 (21), 65 (28), 45 (33)
IR (CHCl3) cm-1: 1713, 1668
1H-NMR (CDCl3) δ: 1.27 (6H, s), 1.28 (6H, s), 1.68 (4H, s), 3.00 (1H, br s, OH), 3.55-3.73 (ca. 45H, m), 3.81-3.87 (2H, m), 4.46-4.52 (2H, m), 7.28 (1H, d, J=8.5 Hz), 7.51 (1H, dd, J=8.5, 2 Hz), 7.62 (1H, d, J=2 Hz), 8.01 (2H, A 2B2, J=8 Hz), 8.10 (2H, A2 B 2, J=8 Hz), 8.74 (1H, br s, CONH).
無色飴状物
MS (m/z): 547 (M+, 18), 368 (4), 311 (5), 104 (6), 91 (100), 73 (11). IR (CHCl3) cm-1: 1721, 1671
1H-NMR (CDCl3) δ: 0.29 (18H, s), 1.65 (3H, d, J=7 Hz), 5.17 (1H, d, J=12.5 Hz), 5.23 (1H, d, J=12.5 Hz), 7.30-7.37 (5H, m), 7.46 (1H, t, J=0.5 Hz), 7.80 (2H, br s), 7.93 (2H, A 2B2, J=8.5 Hz), 8.13 (2H, A2 B 2, J=8.5 Hz), 8.13 (1H, br s, CONH).
無色鱗片状晶、融点198-200℃ (ジクロロメタン−ヘキサン)
MS (m/z): 457 (M+, 89), 370 (93), 221 (33), 176 (39), 149 (60), 129 (29), 104 (35), 75 (29), 73 (100)
IR (CHCl3) cm-1: 1720, 1709, 1644, 1626
1H-NMR (CDCl3) δ: 0.30 (18H, s), 1.72 (3H, d, J=7 Hz), 5.42 (1H, q, J=7 Hz), 7.46 (1H, br s), 7.77 (2H, br s), 7.80 (1H, br s, CONH), 7.97 (2H, A 2B2, J=8.5 Hz), 8.21 (2H, A2 B 2, J=8.5 Hz).
IR (neat) cm-1: 1747
1H-NMR (CDCl3) δ: 1.18 (9H, s), 1.35 (3H, d, J=7 Hz), 4.16 (1H, q, J=7 Hz), 5.13 (1H, d, J=12.5 Hz), 5.19 (1H, d, J=12.5 Hz), 7.29-7.42 (5H, m).
IR (neat) cm-1: 1747
1H-NMR (CDCl3) δ: 1.19 (9H, s), 1.35 (3H, d, J=7 Hz), 1.52 (3H, d, J=7 Hz), 4.18 (1H, q, J=7 Hz), 5.16 (2H, s), 5.19 (1H, q, J=7 Hz), 7.30-7.40 (5H, m).
IR (neat) cm-1: 1748, 1670
1H-NMR (CDCl3) δ: 1.21 (9H, s), 1.39 (3H, d, J=7 Hz), 1.517 (3H, d, J=7 Hz), 1.520 (3H, d, J=7 Hz), 1.57 (3H, d, J=7 Hz), 4.20 (1H, q, J=7 Hz), 5.10-5.23 (5H, m), 7.28-7.40 (5H, m).
MS (m/z): 763 (M+, 12), 512 (2), 440 (2), 368 (17), 176 (9), 104 (9), 91 (100), 73 (15), 56 (11)
IR (CHCl3) cm-1: 1748, 1672
1H-NMR (CDCl3) δ: 0.29 (18H, s), 1.50 (3H, d, J=7.5 Hz), 1.51 (3H, d, J=7 Hz), 1.59 (3H, d, J=7.5 Hz), 1.72 (3H, d, J=7 Hz), 5.08-5.24 (5H, m), 5.37 (1H, q, J=7 Hz), 7.28-7.39 (5H, m), 7.45 (1H, dif t, J=1 Hz), 7.80 (2H, br s), 7.92 (2H, A 2B2, J=8.5 Hz), 8.12 (2H, A2 B 2, J=8.5 Hz), 8.22 (1H, br s, CONH).
MS (m/z): 673 (M+, 69), 601 (42), 370 (79), 368 (71), 296 (45), 176 (88), 149 (62), 104 (65), 73 (100), 55 (58), 45 (49)
IR (KBr) cm-1: 1753, 1726, 1652
1H-NMR (CDCl3) δ: 0.31 (18H, s), 1.56 (3H, d, J=7 Hz), 1.57 (3H, d, J=7.5 Hz), 1.62 (3H, d, J=7 Hz), 1.73 (3H, d, J=7.5 Hz), 5.12-5.28 (3H, m), 5.40 (1H, q, J=7 Hz), 7.46 (1H, br s), 7.76 (2H, br s), 7.87 (1H, br s, CONH), 7.95 (2H, A 2B2, J=8 Hz), 8.19 (2H, A2 B 2, J=8 Hz).
14: 無色微細針状晶、融点131-132℃ (ジクロロメタン−ヘキサン)。
MS (m/z): 437 (M+, 17), 422 (10), 350 (7), 229 (10), 214 (72), 163 (100), 135 (19), 103 (13), 43 (11), 29 (16)
IR (KBr) cm-1: 1736, 1722, 1687
1H-NMR (CDCl3) δ: 1.04 (3H, t, J=7 Hz), 1.23 (6H, s), 1.28 (6H, s), 1.68 (4H, s), 3.94 (3H, s), 4.12 (2H, q, J=7 Hz), 6.98 (1H, dd, J=8, 2.5 Hz), 7.09 (1H, d, J=2.5 Hz), 7.33 (1H, d, J=8 Hz), 7.72 (2H, A 2B2, J=8 Hz), 8.08 (2H, A2 B 2, J=8 Hz).
16: 無色プリズム晶、融点125-126℃ (ジクロロメタン−ヘキサン)
MS (m/z): 451 (M+, 1), 406 (1), 215 (100), 172 (4), 157 (5), 43 (4)
IR (KBr) cm-1: 1737, 1708, 1688
1H-NMR (CDCl3) δ: 1.02 (3H, t, J=7 Hz), 1.25 (6H, s), 1.28 (6H, s), 1.38 (3H, t, J=7 Hz), 1.68 (4H, s), 4.13 (2H, q, J=7 Hz), 4.37 (2H, q, J=7 Hz), 7.31 (2H, A 2B2, J=8 Hz), 7.35 (1H, d, J=8 Hz), 7.49 (1H, dd, J=8, 2 Hz), 7.67 (1H, d, J=2 Hz), 8.08 (2H, A2 B 2, J=8 Hz).
18: 無色針状晶、融点118.5-119.5℃ (ジクロロメタン−ヘキサン)
MS (m/z): 393 (M+, 15), 249 (4), 215 (100), 172 (5), 157 (10), 91 (6), 43 (9)
IR (KBr) cm-1: 1731, 1638
1H-NMR (CDCl3) δ: 1.29 (6H, s), 1.30 (6H, s), 1.70 (4H, s), 2.61 (2H, t, J=8 Hz), 2.92 (2H, t, J=8 Hz), 3.66 (3H, s), 7.17 (2H, A 2B2, J=8.5 Hz), 7.36 (1H, d, J=8 Hz), 7.55 (1H, dd, J=8, 2 Hz), 7.56 (2H, A2 B 2, J=8.5 Hz), 7.86 (1H, d, J=2 Hz), 7.99 (1H, br s, CONH).
無色プリズム晶、融点172.5-174℃ (ジクロロメタン−ヘキサン)
MS (m/z): 379 (M+, 15), 215 (100), 157 (12), 131 (5), 128 (6), 91 (5), 43 (12)
IR (KBr) cm-1: 1704, 1638
1H-NMR (CDCl3) δ: 1.30 (6H, s), 1.32 (6H, s), 1.71 (4H, s), 2.68 (2H, t, J=8 Hz), 2.96 (2H, t, J=8 Hz), 7.22 (2H, A 2B2, J=8.5 Hz), 7.39 (1H, d, J=8 Hz), 7.54 (1H, dd, J=8, 2 Hz), 7.57 (2H, A2 B 2, J=8.5 Hz), 7.75 (1H, br s, CONH), 7.85 (1H, d, J=2 Hz).
21: 無色プリズム晶、融点135-136℃ (ジクロロメタン−ヘキサン)
MS (m/z): 393 (M+, 35), 378 (100), 362 (5), 191 (76), 131 (35), 103 (18), 91 (10), 59 (7), 43 (10)
IR (KBr) cm-1: 1707, 1659
1H-NMR (CDCl3) δ: 1.28 (6H, s), 1.30 (6H, s), 1.69 (4H, s), 2.67 (2H, t, J=7.5 Hz), 3.02 (2H, t, J=7.5 Hz), 3.68 (3H, s), 7.30 (1H, d, J=8.5 Hz), 7.32 (2H, A 2B2, J=8 Hz), 7.41 (1H, dd, J=8.5, 2.5 Hz), 7.53 (1H, d, J=2.5 Hz), 7.69 (1H, br s, CONH), 7.80 (2H, A2 B 2, J=8 Hz).
無色針状晶、融点229-230℃ (メタノール−ジクロロメタン)
MS (m/z): 379 (M+, 33), 364 (100), 177 (92), 131 (14), 107 (22), 103 (20), 77 (16)
IR (KBr) cm-1: 1711, 1616
1H-NMR (CDCl3) δ: 1.28 (6H, s), 1.30 (6H, s), 1.69 (4H, s), 2.72 (2H, t, J=7.5 Hz), 3.04 (2H, t, J=7.5 Hz), 7.30 (1H, d, J=8.5 Hz), 7.33 (2H, A 2B2, J=8.5 Hz), 7.41 (1H, dd, J=8.5, 2 Hz), 7.53 (1H, d, J=2 Hz), 7.73 (1H, br s, CONH), 7.80 (2H, A2 B 2, J=8.5 Hz).
23: 無色飴状物質
MS (m/z): 436 (M+, 58), 421 (84), 334 (17), 318 (100), 234 (26), 174 (23), 104 (62), 76 (25), 43 (34)
IR (CHCl3) cm-1: 1733, 1657
1H-NMR (CDCl3) δ: 1.27 (12H, s), 1.50 (3H, d, J=7 Hz), 1.68 (4H, s), 3.75 (3H, s), 4.74 (1H, dq, J=7.5, 7 Hz), 7.22 (1H, br d, J=7.5 Hz, NH), 7.27 (1H, d, J=8.5 Hz), 7.51 (1H, dd, J=8.5, 2 Hz), 7.65 (2H, A 2B2, J=8.5 Hz), ca. 7.64-7.67 (1H, m), 7.73 (2H, A2 B 2, J=8.5 Hz), 8.69 (1H, br s, CONH).
無色プリズム晶、融点197-198℃ (ジクロロメタン−酢酸エチル)
MS (m/z): 422 (M+, 57), 407 (89), 318 (100), 220 (34), 174 (30), 104 (73), 76 (36), 43 (45)
IR (KBr) cm-1: 1720, 1660, 1624
1H-NMR (DMSO-d6) δ: 1.23 (6H, s), 1.24 (6H, s), 1.41 (3H, d, J=7 Hz), 1.64 (4H, s), 4.43 (1H, dq, J=7, 7 Hz), 7.28 (1H, d, J=8.5 Hz), 7.57 (1H, dd, J=8.5, 2 Hz), 7.67 (1H, d, J=2 Hz), 7.99 (2H, A 2B2, J=8.5 Hz), 8.04 (2H, A2 B 2, J=8.5 Hz), 8.81 (1H, d, J=7 Hz, NH), 10.19 (1H, br s, CONH).
25: 無色針状晶、融点240-242℃ (メタノール−ジクロロメタン)
MS (m/z): 479 (M+, 92), 464 (48), 375 (56), 334 (30), 318 (100), 291 (26), 160 (67), 104 (89), 88 (42)
IR (KBr) cm-1: 1745, 1655, 1637
1H-NMR (DMSO-d6) δ: 1.23 (6H, s), 1.24 (6H, s), 1.64 (4H, s), 3.62 (3H, s), 3.87 (2H, d, J=6 Hz), 3.94 (2H, d, J=6 Hz), 7.28 (1H, d, J=8.5 Hz), 7.57 (1H, dd, J=8.5, 2 Hz), 7.67 (1H, d, J=2 Hz), 8.00 (2H, A 2B2, J=9 Hz), 8.04 (2H, A2 B 2, J=9 Hz), 8.38 (1H, t, J=6 Hz, NH), 8.95 (1H, t, J=6 Hz, NH), 10.19 (1H, br s, CONH).
無色プリズム晶、融点228-229℃ (メタノール−酢酸エチル)
MS (m/z): 465 (M+, 15), 432 (18), 408 (47), 393 (83), 375 (83), 347 (34), 336 (63), 318 (90), 206 (44), 160 (100), 149 (49), 104 (100), 76 (51), 43 (47)
IR (KBr) cm-1: 1715, 1664, 1634
1H-NMR (DMSO-d6) δ: 1.23 (6H, s), 1.24 (6H, s), 1.64 (4H, s), 3.76 (2H, d, J=6 Hz), 3.94 (2H, d, J=6 Hz), 7.28 (1H, d, J=8.5 Hz), 7.57 (1H, dd, J=8.5, 2 Hz), 7.67 (1H, d, J=2 Hz), 8.00 (2H, A 2B2, J=8.5 Hz), 8.04 (2H, A2 B 2, J=8.5 Hz), 8.23 (1H, t, J=6 Hz, NH), 8.93 (1H, t, J=6 Hz, NH), 10.19 (1H, br s, CONH).
MS (m/z): 527 (M+, 13), 512 (4), 163 (100), 135 (14), 103 (10), 77 (5)
IR (KBr) cm-1: 1720, 1696, 1668
1H-NMR (CDCl3) δ: 1.05 (6H, s), 1.23 (6H, s), 1.61 (4H, s), 3.92 (6H, s), 6.91 (1H, d, J=2 Hz), 6.96 (1H, dd, J=8.5, 2 Hz), 7.29 (1H, d, J=8.5 Hz), 7.75 (4H, A 2B2, J=8 Hz), 8.01 (4H, A2 B 2, J=8 Hz).
Claims (6)
- 下記の一般式(I):
- XとZがこれらが結合するベンゼン環上においてパラ位である請求項1に記載の化合物又はその塩、あるいはそのエステル。
- R1、R4、及びR5が水素原子であり、R2及びR3が互いに結合してそれらが結合するベンゼン環とともに5,5,8,8-テトラメチル-5,6,7,8- テトラヒドロナフタレン環を形成する請求項1に記載の化合物又はその塩、あるいはそのエステル。
- R1、R3、及びR5が水素原子であり、R2及びR4がトリメチルシリル基である請求項1に記載の化合物又はその塩、あるいはそのエステル。
- X が-N(COR6)-CO-又は-CO-N(COR7)-(R6又はR7はメトキシ基又はエトキシ基である)であり、Zが-COOR13(R13は水素原子である)である請求項1に記載の化合物又はその塩、あるいはそのエステル。
- Xが-NH-CO-(該アミド基の炭素原子はZが置換するベンゼン環に結合する)であり、Zが-Y-CH(R12)-COOH(Yは-CH2-、-CH(OH)-、又は-CO-である)又は-COOR13である請求項1に記載の化合物又はその塩、あるいはそのエステル。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US7855300B2 (en) | 2007-10-11 | 2010-12-21 | Taiho Pharmaceutical Co., Ltd. | Bis(trimethylsilyl)phenyl compound or salt thereof, and use thereof |
CN102329246A (zh) * | 2011-07-04 | 2012-01-25 | 潍坊博创国际生物医药研究院 | 多靶点型他米巴罗汀衍生物、其制备方法和用途 |
WO2013005753A1 (ja) * | 2011-07-05 | 2013-01-10 | 公益財団法人乙卯研究所 | 重水素化フェニルプロピオン酸誘導体 |
CN103664680A (zh) * | 2012-09-26 | 2014-03-26 | 山东鲁北药业有限公司 | 一种他米巴罗汀合成的新工艺 |
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JPH11507960A (ja) * | 1997-02-10 | 1999-07-13 | センタ インタナショナル ドゥ リシェルシェ デルマトロジーク ガルデルマ(セ イ エール デ ガルデルマ) | 二環式芳香族化合物、これらを含有する組成物及びその使用 |
JP2000500499A (ja) * | 1995-11-22 | 2000-01-18 | ビジョン・ファーマシューティカルズ・リミテッド・パートナーシップ | レチノイド様生物学的活性を有する、テトラヒドロナフタレン、クロマン、チオクロマンおよび1,2,3,4―テトラヒドロキノリンカルボン酸のアリールまたはヘテロアリールアミド |
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JP2000500499A (ja) * | 1995-11-22 | 2000-01-18 | ビジョン・ファーマシューティカルズ・リミテッド・パートナーシップ | レチノイド様生物学的活性を有する、テトラヒドロナフタレン、クロマン、チオクロマンおよび1,2,3,4―テトラヒドロキノリンカルボン酸のアリールまたはヘテロアリールアミド |
JPH11507960A (ja) * | 1997-02-10 | 1999-07-13 | センタ インタナショナル ドゥ リシェルシェ デルマトロジーク ガルデルマ(セ イ エール デ ガルデルマ) | 二環式芳香族化合物、これらを含有する組成物及びその使用 |
WO1999024415A1 (fr) * | 1997-11-12 | 1999-05-20 | Institute Of Medicinal Molecular Design, Inc. | Agonistes du recepteur du retinoide |
WO2005056516A1 (en) * | 2003-12-08 | 2005-06-23 | Galderma Research & Development, S.N.C. | Biphenyl derivatives useful as ligands that activate the rar receptors, process for preparing them and use thereof in human medicine and in cosmetics |
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US7855300B2 (en) | 2007-10-11 | 2010-12-21 | Taiho Pharmaceutical Co., Ltd. | Bis(trimethylsilyl)phenyl compound or salt thereof, and use thereof |
CN102329246A (zh) * | 2011-07-04 | 2012-01-25 | 潍坊博创国际生物医药研究院 | 多靶点型他米巴罗汀衍生物、其制备方法和用途 |
CN102329246B (zh) * | 2011-07-04 | 2013-11-20 | 潍坊博创国际生物医药研究院 | 多靶点型他米巴罗汀衍生物、其制备方法和用途 |
WO2013005753A1 (ja) * | 2011-07-05 | 2013-01-10 | 公益財団法人乙卯研究所 | 重水素化フェニルプロピオン酸誘導体 |
JP5193400B2 (ja) * | 2011-07-05 | 2013-05-08 | 公益財団法人乙卯研究所 | 重水素化フェニルプロピオン酸誘導体 |
CN103664680A (zh) * | 2012-09-26 | 2014-03-26 | 山东鲁北药业有限公司 | 一种他米巴罗汀合成的新工艺 |
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