Methods and Compositions Using Certain Phenolic Derivatives for the Treatment of Diabetes
First Claim
1. A method for the treatment or prophylaxis of diabetes, a pre-diabetes condition or a diabetes related disorder in a host, comprising administering a compound of formula (X-1), or a pharmaceutically acceptable salt, ester, pharmaceutically acceptable derivative, or prodrug thereof, is provided wherein X is S, Se, S(O) and S(O)2;
- Y is S, Se, S(O) and S(O)2;
A comprises one or more groups selected from optionally substituted C1-6 alkylene, optionally substituted C2-6 alkenylene; and
optionally substituted C3-10 cycloalkylene;
n is 0 or 1;
R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 may be the same or different and are independently selected from the group consisting of hydrogen, halogen, hydroxyl, thiol, —
NR11R12, nitro, cyano, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, optionally substituted aryl(C1-6 alkyl), optionally substituted (C1-6 alkyl)aryl, optionally substituted heteroaryl, optionally substituted C3-10 heterocycloalkyl, C(O)R11, OR12, CH2OR12, CH2NR13R14, C(O)OR12 and C(O)NR13R14;
R11 is selected from OH, C1-6 alkyl, and C1-6 alkenyl;
R12 is selected from the group consisting of hydrogen, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10-alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, —
C(O)(C1-6)alkyl-CO2R15, —
C(O)(C2-6)alkenyl-CO2R15, and —
C(O)NR13R14;
R13 and R14 may be the same or different and are individually selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 heterocycloalkyl, aryl, (C1-6)alkylaryl, and heteroaryl; and
R15 is H or C1-4 alkyl.
1 Assignment
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Accused Products
Abstract
This present invention provides methods and pharmaceutical compositions for the treatment or prophylaxis of diabetes and related disorders, comprising the administration of an effective amount of a compound including an optionally substituted phenyl ring linked to an aromatic or alkyl group by a spacer, wherein the spacer includes two groups selected from selenium, sulfur, S(O) and S(O)2 and may include an alkylene, alkenylene, cycloalkylene or arylene moiety between the selenium, sulfur, S(O) or S(O)2 groups, or a pharmaceutically acceptable salt or derivative thereof.
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Citations
21 Claims
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1. A method for the treatment or prophylaxis of diabetes, a pre-diabetes condition or a diabetes related disorder in a host, comprising administering a compound of formula (X-1), or a pharmaceutically acceptable salt, ester, pharmaceutically acceptable derivative, or prodrug thereof, is provided
wherein X is S, Se, S(O) and S(O)2; -
Y is S, Se, S(O) and S(O)2; A comprises one or more groups selected from optionally substituted C1-6 alkylene, optionally substituted C2-6 alkenylene; and
optionally substituted C3-10 cycloalkylene;n is 0 or 1; R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 may be the same or different and are independently selected from the group consisting of hydrogen, halogen, hydroxyl, thiol, —
NR11R12, nitro, cyano, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, optionally substituted aryl(C1-6 alkyl), optionally substituted (C1-6 alkyl)aryl, optionally substituted heteroaryl, optionally substituted C3-10 heterocycloalkyl, C(O)R11, OR12, CH2OR12, CH2NR13R14, C(O)OR12 and C(O)NR13R14;R11 is selected from OH, C1-6 alkyl, and C1-6 alkenyl; R12 is selected from the group consisting of hydrogen, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10-alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, —
C(O)(C1-6)alkyl-CO2R15, —
C(O)(C2-6)alkenyl-CO2R15, and —
C(O)NR13R14;R13 and R14 may be the same or different and are individually selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 heterocycloalkyl, aryl, (C1-6)alkylaryl, and heteroaryl; and R15 is H or C1-4 alkyl. - View Dependent Claims (2, 3, 4, 5, 6, 7, 17, 18, 19)
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8. A method for the treatment or prophylaxis of diabetes, a pre-diabetes condition or a diabetes related disorder in a host, comprising administering an effective amount of a compound of Formula (X-2), or a pharmaceutically acceptable salt, ester, pharmaceutically acceptable derivative, or prodrug thereof:
wherein X is selected from S, Se, S(O) and S(O)2; Y is selected from S, Se, S(O) and S(O)2; R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 may be the same or different and are independently selected from the group consisting of hydrogen, halogen, hydroxyl, thiol, —
NR11R12, nitro, cyano, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, optionally substituted aryl(C1-6 alkyl), optionally substituted (C1-6 alkyl)aryl, optionally substituted heteroaryl, optionally substituted C3-10 heterocycloalkyl, C(O)R11, OR12, CH2OR12, CH2NR13R14, C(O)OR12 and C(O)NR13R14;R11 is selected from OH, C1-6 alkyl, and C1-6 alkenyl; R12 is selected from the group consisting of hydrogen, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, —
C(O)(C1-6)alkyl-CO2R15, —
C(O)(C2-6)alkenyl-CO2R15 and —
C(O)NR13R14;R13 and R14 may be the same or different and are individually selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 heterocycloalkyl, aryl, (C1-6)alkylaryl, and heteroaryl; and R15 is H or C1-4 alkyl. - View Dependent Claims (9, 10, 11)
- 12. A method for the treatment or prophylaxis of diabetes, a pre-diabetes condition or a diabetes related disorder in a host, comprising administering an effective amount of a compound of the structure:
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16. A method of glycemic control in a host in need thereof is provided, including administering an effective amount of a compound of formula (X-1), or a pharmaceutically acceptable salt, ester, pharmaceutically acceptable derivative, or prodrug thereof, is provided
wherein X is S, Se, S(O) and S(O)2; -
Y is S, Se, S(O) and S(O)2; A comprises one or more groups selected from optionally substituted C1-6 alkylene, optionally substituted C2-6 alkenylene; and
optionally substituted C3-10 cycloalkylene;n is 0 or 1; R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 may be the same or different and are independently selected from the group consisting of hydrogen, halogen, hydroxyl, thiol, —
NR11R12, nitro, cyano, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, optionally substituted aryl(C1-6 alkyl), optionally substituted (C1-6 alkyl)aryl, optionally substituted heteroaryl, optionally substituted C3-10 heterocycloalkyl, C(O)R11, OR12, CH2OR12, CH2NR13R14, C(O)OR12 and C(O)NR13R14;R11 is selected from OH, C1-6 alkyl, and C1-6 alkenyl; R12 is selected from the group consisting of hydrogen, optionally substituted C1-10 alkyl, optionally substituted C2-10-alkenyl, optionally substituted C2-10-alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, —
C(O)(C1-6)alkyl-CO2R15, —
C(O)(C2-6)alkenyl-CO2R15, and —
C(O)NR13R14;R13 and R14 may be the same or different and are individually selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 heterocycloalkyl, aryl, (C1-6)alkylaryl, and heteroaryl; and R15 is H or C1-4 alkyl.
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20. A method of glycemic control in a host in need thereof is provided, including administering an effective amount of a compound of Formula (X-2), or a pharmaceutically acceptable salt, ester, pharmaceutically acceptable derivative, or prodrug thereof:
wherein X is selected from S, Se, S(O) and S(O)2; Y is selected from S, Se, S(O) and S(O)2; R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 may be the same or different and are independently selected from the group consisting of hydrogen, halogen, hydroxyl, thiol, —
NR11R12 nitro, cyano, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, optionally substituted aryl(C1-6 alkyl), optionally substituted (C1-6 alkyl)aryl, optionally substituted heteroaryl, optionally substituted C3-10 heterocycloalkyl, C(O)R11, OR12, CH2OR12, CH2NR13R14, C(O)OR12 and C(O)NR13R14;R11 is selected from OH, C1-6 alkyl, and C1-6 alkenyl; R12 is selected from the group consisting of hydrogen, optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted aryl, —
C(O)(C1-6)alkyl-CO2R15, —
C(O)(C2-6)alkenyl-CO2R15, and —
C(O)NR13R14;R13 and R14 may be the same or different and are individually selected from hydrogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 heterocycloalkyl, aryl, (C1-6)alkylaryl, and heteroaryl; and R15 is H or C1-4 alkyl.
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21. A method of glycemic control in a host in need thereof is provided, including administering an effective amount of a compound of a compound:
Specification