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US 2014/0350104 A1Published application
Methods and compositions for reducing body fat and adipocytes
AssigneeTopokine Therapeutics, Inc.
InventorsMurat V. Kalayoglu, Michael S. Singer
Life of this patent
Estimating the term…
Abstract
Provided are methods of reducing body fat in a subject, comprising locally (e.g., topically) administering one or more compounds of the Formula (I) and/or (V) or a pharmaceutically acceptable salt, hydrate, solvate, stereoisomer, polymorph, tautomer, isotopically enriched derivative, or prodrug thereof, wherein X is —OR1 —SR2 or —NR3R4, and R1, R2, R3, R4, R5, R6, R7, R7′, Z, Y, n, y, and x, are as defined herein.
Claims27
A method for reducing fat in a body of a subject in need thereof, the method comprising administering locally to the subject a compound of the Formula (I):
- or a pharmaceutically acceptable salt, hydrate, solvate, stereoisomer, polymorph, tautomer, isotopically enriched derivative, or prodrug thereof;
- wherein:
- X is selected from:
- —OR1, wherein R1 is selected from the group consisting of hydrogen, a hydroxyl protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
- —SR2, wherein R2 group consisting of hydrogen, a thiol protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
- —NR3R4, wherein R3 and R4 are independently selected from the group consisting of hydrogen, an amino protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, or R3 and R4 are joined to form an optionally substituted heterocyclyl ring.
3 more elements
A method for reducing fat in a body of a subject in need thereof, the method comprising administering locally to the subject a compound of the Formula (V):
- or a pharmaceutically acceptable salt, hydrate, solvate, stereoisomer, polymorph, tautomer, isotopically enriched derivative thereof, or prodrug thereof;
- wherein:
- X is:
- —OR1, wherein R1 is selected from the group consisting of hydrogen, a hydroxyl protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
- —SR2, wherein R2 group consisting of hydrogen, a thiol protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
- or
- —NR3R4, wherein R3 and R4 are independently selected from the group consisting of hydrogen, an amino protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, or R3 and R4 are joined to form an optionally substituted heterocyclyl ring;
- Z is ═O or represents two hydrogen atoms;
- one of R5 and R6 is ═O, —OH, or a —O(CO)R8 group and the other one is —OH or —O(CO)R8, or R5 is ═O and R6 is H, wherein R8 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms or —(CH2)mR9 wherein m is 0-10, and R9 is cycloalkyl having from three to seven carbon atoms, aryl having from six to ten carbon atoms, or heteroaryl having from four to ten carbon atoms and one to four heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur
- R7 is hydrogen, halogen, —OH or —O(CO)R10, wherein R10 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms or —(CH2)mR11 wherein m is 0-10, and R11 is cycloalkyl having from three to seven carbon atoms, aryl having from six to ten carbon atoms, or heteroaryl having from four to ten carbon atoms and one to four heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
- R7′ is hydrogen or halogen;
- Y is selected from the group consisting of alkyl, halo, nitro, amino, thiol, hydroxy, alkyloxy, alkylcarboxy and halosubstituted alkyl, wherein said alkyl radical comprises from one to six carbon atoms;
- y is 0 or 1, and x is 0 or 1, provided x and y are not both 1;
- and
- n is 0 or an integer of from 1 to 3, inclusive.
12 more elements
A pharmaceutical composition for reducing body fat, comprising a therapeutically effective amount of a compound of Formula (I):
- or a pharmaceutically acceptable salt, hydrate, solvate, stereoisomer, polymorph, tautomer, isotopically enriched derivative, or prodrug thereof;
- and optionally one or more pharmaceutically acceptable excipients;
- wherein:
- X is selected from:
- —OR1, wherein R1 is selected from the group consisting of hydrogen, a hydroxyl protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
- —SR2, wherein R2 group consisting of hydrogen, a thiol protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
- —NR3R4, wherein R3 and R4 are independently selected from the group consisting of hydrogen, an amino protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, or R3 and R4 are joined to form an optionally substituted heterocyclyl ring.
4 more elements
A pharmaceutical composition for reducing body fat, comprising a therapeutically effective amount of a compound of Formula (V):
- or a pharmaceutically acceptable salt, hydrate, solvate, stereoisomer, polymorph, tautomer, isotopically enriched derivative thereof, or prodrug thereof;
- wherein:
- X is:
- —OR1, wherein R1 is selected from the group consisting of hydrogen, a hydroxyl protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
- —SR2, wherein R2 group consisting of hydrogen, a thiol protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl;
- or
- —NR3R4, wherein R3 and R4 are independently selected from the group consisting of hydrogen, an amino protecting group, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, or R3 and R4 are joined to form an optionally substituted heterocyclyl ring;
- Z is ═O or represents two hydrogen atoms;
- one of R5 and R6 is ═O, —OH, or a —O(CO)R8 group and the other one is —OH or —O(CO)R8, or R5 is ═O and R6 is H, wherein R8 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms or —(CH2)mR9 wherein m is 0-10, and R9 is cycloalkyl having from three to seven carbon atoms, aryl having from six to ten carbon atoms, or heteroaryl having from four to ten carbon atoms and one to four heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur
- R7 is hydrogen, halogen, —OH or —O(CO)R10, wherein R10 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms or —(CH2)mR11 wherein m is 0-10, and R11 is cycloalkyl having from three to seven carbon atoms, aryl having from six to ten carbon atoms, or heteroaryl having from four to ten carbon atoms and one to four heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
- R7′ is hydrogen or halogen;
- Y is selected from the group consisting of alkyl, halo, nitro, amino, thiol, hydroxy, alkyloxy, alkylcarboxy and halosubstituted alkyl, wherein said alkyl radical comprises from one to six carbon atoms;
- y is 0 or 1, and x is 0 or 1, provided x and y are not both 1;
- and
- n is 0 or an integer of from 1 to 3, inclusive.
12 more elements
Dependencies are inferred from the claim text.