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US 2002/0160946 A1Published application
Compounds having antifungal activity
AssigneeSankyo Company, Limited
InventorsTatsuya Yano, Masatoshi Inukai, Toshio Takatsu, Isshin Tanaka
Life of this patent
Estimating the term…
Abstract
A compound of the following chemical structure (I) which exhibits antifungal activity and is useful in treating and preventing fungal infectious diseases: 1
Claims32
a compound of the following chemical structure (I), or a pharmaceutically acceptable salt thereof:
- 5
A compound having the following physicochemical properties, or a pharmaceutically acceptable salt thereof:
- 1) Property:
- Basic liposoluble powder
- 2) Molecular formula:
- C55H98N8O14
- 3) Molecular weight:
- 1094 (FAB-MS method)
- 4) High resolution FAB-MS [M+H]+
- calculated for C55H99N8O14 1095.7281 found 1095.7365
- 5) Ultra violet absorption spectrum:
- End absorption
- 6) Infra red absorption spectrum (KBr pellet, cm−1):
- 3434, 3335, 2962, 2937, 2875, 2806, 1750, 1684, 1641, 1509, 1469, 1412, 1371, 1314, 1294, 1271, 1204, 1156, 1128, 1074,1020
- 7) Optical rotation:
- [α]D25−120° (c 1.0, methanol)
- 8) 1H NMR spectrum (in CDCl3, 500 MHz, δ (ppm), internal standard:
- tetramethylsilane):
- 0.78(3H), 0.79(3H), 0.80(3H), 0.82(3H), 0.87(3H), 0.88(1H), 0.92(3H), 0.93(3H), 0.94(3H), 0.96(3H), 0.97(3H), 0.98(3H), 1.01(3H), 1.02(3H), 1.03(3H),1.06(3H), 1.21(1H), 1.41(3H), 1.41(1H), 1.48(1H), 1.48(1H), 1.49(1H), 1.52(3H), 1.55(1H), 1.65(1H), 1.66(1H), 1.70(2H), 1.73(1H), 1.81(1H), 1.87(1H), 2.28(1H), 2.31(1H), 2.37(1H), 2.48(3H), 2.89(3H), 2.94(3H), 2.96(1H), 3.29(3H), 3.56(1H), 4.06(1H), 4.14(1H), 4.77(1H), 4.78(1H), 4.84(1H), 4.91(1H), 4.96(1H), 5.21(1H), 5.25(1H), 5.53(1H), 6.39(1H), 7.83(1H), 7.94(1H), 8.28(1H),
- 9) 13C NMR spectrum (in CDCl3, 500 MHz, δ (ppm), internal standard:
- tetramethylsilane):
- 10.9(q), 11.9(q), 15.0(q), 15.1(q), 16.0(q), 16.6(q), 17.4(q), 18.3(q), 18.6(q), 18.7(q), 19.1(q), 21.0(q), 21.4(q), 22.1(q), 23.1(q), 23.51(q), 23.54(q), 24.2(t), 24.6(d), 24.8(d), 25.4(d), 25.5(t), 27.7(d), 29.5(q), 29.8(d), 30.2(q), 36.1(q), 36.5(t), 37.7(t), 38.3(d), 38.4(d), 39.7(t), 40.9(q), 46.2(d), 51.8(d), 53.1(d), 54.7(d), 55.1(d), 63.9(d), 64.7(d), 68.1(d), 70.1(d), 73.4(d), 74.3(d), 77.1(d), 169.03(s), 169.04(s), 169.6(s), 169.8(s), 169.9(s), 170.3(s), 172.0(s), 173.4(s) 173.8(s), 174.0(s)
- 10) High performance liquid chromatography:
- Column:
- Shodex Asahipak C8P 50 4E (diameter 4.6 mm×length 250 mm (product of Showa Denko K.K.)
- Mobile phase:
- Acetonitrile:10 mM aqueous ammonium hydrogencarbonate solution=13:7
- Flow rate:
- 0.7 ml/minute
- Wave length of detection:
- λ 210 nm
- Retention time:
- 10.20 minutes
- 11) Solubility:
- soluble in dimethylsulfoxide, methanol, and chloroform
- 12) Amino acid analysis:
- Threonine, alanine and isoleucine were detected from the hydrolysate
32 more elements
A compound of the following chemical structure (II):
- 6
A compound having the following physicochemical properties:
- 1) Property:
- Neutral liposoluble powder
- 2) Molecular formula:
- C57H100N8O15
- 3) Molecular weight:
- 1136 (FAB-MS method)
- 4) High resolution FAB-MS [M+H]+
- calculated for C57H101N8O15 1137.7387 found 1137.7410
- 5) Ultra violet absorption spectrum:
- End absorption
- 6) Infra red absorption spectrum (KBr pellet, cm−1):
- 3433, 3333, 2963, 2937, 2875, 1751, 1686, 1642, 1516, 1469, 1409, 1388, 1372, 1311, 1292, 1272, 1201, 1156, 1128, 1074,1017
- 7) Optical rotation:
- [α]D25 −131° (c 1.0, methanol)
- 8) 1H NMR spectrum (in CDCl3, 500 MHz, δ (ppm), internal standard:
- tetramethylsilane):
- 0.78(3H), 0.79(3H), 0.80(3H), 0.83(3H), 0.87(1H), 0.87(3H), 0.90(3H), 0.92(3H), 0.93(3H), 0.95(3H), 0.95(3H), 0.98(3H), 0.98(3H), 1.01(3H), 1.01(3H), 1.03(1H), 1.05(3H), 1.28(3H), 1.37(1H), 1.40(1H), 1.46(1H), 1.47(1H), 1.49(1H), 1.51(3H), 1.64(1H), 1.65(1H), 1.66(1H), 1.86(1H), 1.72(1H), 1.78(1H), 2.12(3H), 2.13(1H), 2.26(1H), 2.31(1H), 2.37(1H), 2.88(3H), 2.93(3H), 2.97(3H), 3.28(3H), 3.56(1H), 4.03(1H), 4.15(1H), 4.73(1H), 4.78(1H), 4.82(1H), 4.83(1H), 4.91(1H), 4.97(1H), 5.15(1H), 5.28(1H), 5.50(1H), 6.37( 1H) 6.87(1H), 7.86(1H), 8.29(1H).
- 9) 13C NMR spectrum (in CDCl3, 500 MHz, δ (ppm), internal standard:
- tetramethylsilane):
- 10.5(q), 10.9(q), 14.9(q), 15.1(q), 15.6(q), 16.6(q), 16.7(q), 18.3(q), 18.6(q), 18.7(q) 19.0(q), 20.8(q), 21.4(q), 22.0(q), 22.1(q), 23.1(q), 23.6(q), 23.6(q), 24.1(t), 24.6(t), 24.7(d), 24.8(d), 25.4(d), 27.7(d), 29.5(q), 29.8(d), 30.2(q), 31.6(d), 31.8(q), 36.1(t), 37.6(t), 38.4(d), 39.6(t), 40.9(q), 46.1(d), 51.8(d), 53.1(d), 54.7(d), 54.7(d), 61.2(d), 63.9(d), 64.6(d), 68.1(d), 73.1(d), 74.3(d), 77.0(d), 168.9(s), 168.9(s), 169.1(s), 169.9(s), 169.9(s), 170.3(s), 170.6(s), 171.7(s), 172.0(s), 173.3(s), 173.8(s)
- 10) High performance liquid chromatography:
- Column:
- Shodex Asahipak C8P 50 4E (diameter 4.6 mm×length 250 mm (product of Showa Denko K.K.)
- Mobile phase:
- Acetonitrile:10 mM aqueous ammonium hydrogencarbonate solution=13:7
- Flow rate:
- 0.7 ml/minute
- Wave length of detection:
- λ 210 nm
- Retention time:
- 9.05 minutes
- 11) Solubility:
- Soluble in dimethylsulfoxide, methanol, and chloroform
- 12)Amino acid analysis:
- Threonine, alanine and isoleucine were detected from the hydrolysate.
32 more elements
Phoma sp. SANK 13899 (FERM BP-6851) strain.
A compound having the following physicochemical properties or a salt thereof:
- 1) property:
- basic and liposoluble powder
- 2) ultra violet absorption spectrum:
- end absorption
- 3) 1H-NMR (in CDCl3, 500 MHz, δ ppm, internal standard:
- tetramethylsilane):
- 0.78(3H), 0.79(3H), 0.80(3H), 0.82(3H), 0.87(3H), 0.88(1H), 0.92(3H), 0.93(3H), 0.94(3H), 0.96(3H), 0.97(3H), 0.98(3H), 1.01(3H), 1.02(3H), 1.03(3H), 1.06(3H), 1.21(1H), 1.41(3H), 1.41(1H), 1.48(1H), 1.48(1H), 1.49(1H), 1.52(3H), 1.55(1H), 1.65(1H), 1.66(1H), 1.70(2H), 1.73(1H), 1.81(1H), 1.87(1H),2.28(1H), 2.31(1H), 2.37(1H), 2.48(3H), 2.89(3H), 2.94(3H), 2.96(1H), 3.29(3H), 3.56(1H), 4.06(1H), 4.14(1H), 4.77(1H), 4.78(1H), 4.84(1H), 4.91(1H), 4.96(1H), 5.21(1H), 5.25(1H), 5.53(1H), 6.39(1H), 7.83(1H), 7.94(1H), 8.28(1H)
- 4) 13C NMR spectrum (in CDCl3, 500 MHz, δ ppm, internal standard:
- tetramethylsilane):
- 10.9(q), 11.9(q), 15.0(q), 15.1(q), 16.0(q), 16.6(q), 17.4(q), 18.3(q), 18.6(q), 18.7(q), 19.1(q), 21.0(q), 21.4(q), 22.1(q), 23.1(q), 23.51(q), 23.54(q), 24.2(t), 24.6(d), 24.8(d), 25.4(d), 25.5(t), 27.7(d), 29.5(q), 29.8(d), 30.2(q), 36.1(q), 36.5(t), 37.7(t), 38.3(d), 38.4(d), 39.7(t), 40.9(q), 46.2(d), 51.8(d), 53.1(d), 54.7(d), 55.1(d), 63.9(d), 64.7(d), 68.1(d), 70.1(d), 73.4(d), 74.3(d), 77.1(d), 169.03(s), 169.04(s), 169.6(s), 169.8(s), 169.9(s), 170.3(s), 172.0(s), 173.4(s), 173.8(s), 174.0(s)
- 5) high performance liquid chromatography:
- column:
- Shodex Asahipak C8P 50 4E (diameter 4.6 mm×length 250 mm (product of Showa Denko K.K.)
- mobile phase:
- acetonitrile:10 mM aqueous ammonium hydrogencarbonate solution=13:7
- flow rate:
- 0.7 ml/minute
- detection wave length of:
- λ 210 nm
- retention time:
- 10.20 minute
- 6) solubility:
- soluble in dimethylsulfoxide, methanol, and chloroform
- 7) amino acid analysis:
- hydrolysis products are threonine, alanine and isoleucine
22 more elements
Dependencies are inferred from the claim text.