Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds
First Claim
1. An isolated compound, its pharmaceutically acceptable salt or pro-drug ester, having the structure:
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wherein;
R1, R2, R5, R7,and R8 are each separately selected from the group consisting of a hydrogen atom, a halogen atom, and saturated C1-C24 alkyl, unsaturated C1-C24 alkenyl, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, nitro, substituted nitro, phenyl, and substituted phenyl groups, R3, R4, and R6 are each separately selected from the group consisting of a hydrogen atom, a halogen atom, and saturated C1-C12 alkyl, unsaturated C1-C12 alkenyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, nitro, and substituted nitro groups, X1 and X2 are separately selected from the group consisting of an oxygen atom, and a sulfur atom, and the dashed bond represents a bond selected from the group consisting of a carbon-carbon single bond and a carbon-carbon double bond.
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Accused Products
Abstract
A compound, its pharmaceutically acceptable salts, and/or its pro-drug esters, in isolated form, and methods for isolating, for formulating, and for administering the compound, salt, and/or pro-drug ester as an antitumor agent, wherein the compound, salt, or pro-drug ester has the following structure:
wherein:
R1, R2, R5, R7,and R8 are each separately selected from the group consisting of a hydrogen atom, a halogen atom, and saturated C1-C24 alkyl, unsaturated C1-C24 alkenyl, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, nitro, substituted nitro, phenyl, and substituted phenyl groups,
R3, R4, and R6 are each separately selected from the group consisting of a hydrogen atom, a halogen atom, and saturated C1-C12 alkyl, unsaturated C1-C12 alkenyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, nitro, and substituted nitro groups,
X1 and X2 are separately selected from the group consisting of an oxygen atom, and a sulfur atom, and
the dashed bond represents a bond selected from the group consisting of a carbon-carbon single bond and a carbon-carbon double bond. Most preferably, R3 and R4 are hydrogen, and each are involved in hydrogen bonds, and/or the dashed bond is a double bond, such that the chemical backbone of the compound substantially retains a substantially planar conformation.
81 Citations
25 Claims
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1. An isolated compound, its pharmaceutically acceptable salt or pro-drug ester, having the structure:
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wherein; R1, R2, R5, R7,and R8 are each separately selected from the group consisting of a hydrogen atom, a halogen atom, and saturated C1-C24 alkyl, unsaturated C1-C24 alkenyl, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, nitro, substituted nitro, phenyl, and substituted phenyl groups, R3, R4, and R6 are each separately selected from the group consisting of a hydrogen atom, a halogen atom, and saturated C1-C12 alkyl, unsaturated C1-C12 alkenyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, nitro, and substituted nitro groups, X1 and X2 are separately selected from the group consisting of an oxygen atom, and a sulfur atom, and the dashed bond represents a bond selected from the group consisting of a carbon-carbon single bond and a carbon-carbon double bond. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13)
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14. Phenylahistin, its pharmaceutically acceptable salt or pro-drug ester, in isolated form.
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15. (−
- )-Phenylahistin, its pharmaceutically acceptable salt or pro-drug ester, in isolated form.
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16. A method of treating breast cancer in a vertebrate comprising:
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administering to the vertebrate an effective tumor-growth-inhibiting amount of a compound, its pharmaceutically acceptable salt or pro-drug ester, having the following structure;
wherein;
R1, R2, R5, R7,and R8 are each separately selected from the group consisting of a hydrogen atom, a halogen atom, and saturated C1-C24 alkyl, unsaturated C1-C24 alkenyl, cycloalkyl, cycloalkenyl, alkoxy, cycloalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, nitro, substituted nitro, phenyl, and substituted phenyl groups, R3, R4, and R6 are each separately selected from the group consisting of a hydrogen atom, a halogen atom, and saturated C1-C12 alkyl, unsaturated C1-C12 alkenyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, amino, substituted amino, nitro, and substituted nitro groups, X1 and X2 are separately selected from the group consisting of an oxygen atom, and a sulfur atom, and the dashed bond represents a bond selected from the group consisting of a carbon-carbon single bond and a carbon-carbon double bond. - View Dependent Claims (17, 18, 19, 20, 21, 22, 23, 24, 25)
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Specification
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- Resources
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Current AssigneeBeyondSpring Pharmaceuticals, Inc.
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Original AssigneeNereus Pharmaceuticals, Inc.
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InventorsKawashima, Hiroshi, Ohmizo, Kazunori, Fukumoto, Kenji, Sekiya, Hirokatsu, Asari, Tohru, Kanoh, Kaneo, Kohno, Shinkichi, Harada, Takeo
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Primary Examiner(s)Shah, Mukund J.
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Assistant Examiner(s)Balasubramanian, Venkataraman
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Application NumberUS09/440,316Time in Patent Office858 DaysField of Search514/254.05, 544/366US Class Current514/254.05CPC Class CodesA61K 31/496 Non-condensed piperazines c...A61P 35/00 Antineoplastic agentsC07D 403/06 linked by a carbon chain co...
