Adamantylglycine-based inhibitors of dipeptidyl peptidase IV and methods
First Claim
Patent Images
1. A compound of formula (I) wherein:
- n is 0, 1 or 2;
m is 0, 1 or 2;
the sum of n plus m is less then or equal to 2;
the dashed bonds forming a cyclopropyl ring when Y is CH;
X is hydrogen or CN;
Y is CH, CH2, CHF, CF2, O, S, SO, or SO2 A is adamantyl which can be optionally substituted with from zero to six substituents each independently selected from OR1, NR1R2, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, bicycloalkyl, bicycloalkylalkyl, alkylthioalkyl, arylalkylthioalkyl, cycloalkenyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl and cycloheteroalkylalkyl, all optionally substituted through available carbon atoms with 1, 2, 3, 4 or 5 groups selected from hydrogen, halo, alkyl, polyhaloalkyl, alkoxy, haloalkoxy, polyhaloalkoxy, alkoxycarbonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, polycycloalkyl, heteroarylamino, arylamino, cycloheteroalkyl, cycloheteroalkylalkyl, hydroxy, hydroxyalkyl, nitro, cyano, amino, substituted amino, alkylamino, dialkylamino, thiol, alkylthio, alkylcarbonyl, acyl, alkoxycarbonyl, aminocarbonyl, alkynylaminocarbonyl, alkylaminocarbonyl, alkenylaminocarbonyl, alkylcarbonyloxy, alkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, alkylaminocarbonylamino, alkoxycarbonylamino, alkylsulfonyl, aminosulfonyl, alkylsulfinyl, sulfonamido and sulfonyl;
R1 and R2 are each independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl;
including pharmaceutically acceptable salts thereof, and prodrug esters thereof, and all stereoisomers thereof, with the proviso that the compound of formula (I) is not selected from
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Abstract
Compounds are provided having the formula (I)
- wherein:
- n is 0, 1 or 2;
- m is 0, 1 or 2;
- the sum of n+m less then or equal to 2;
- the dashed bonds forming a cyclopropyl ring can only be present when Y is CH;
- X is H or CN;
- Y is CH, CH2, CHF, CF2, O, S, SO, or SO2; and
- A is adamantyl.
Further provided are methods of using such compounds for the treatment of diabetes and related diseases, and to pharmaceutical compositions containing such compounds.
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7 Claims
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1. A compound of formula (I)
wherein: -
n is 0, 1 or 2;
m is 0, 1 or 2;
the sum of n plus m is less then or equal to 2;
the dashed bonds forming a cyclopropyl ring when Y is CH;
X is hydrogen or CN;
Y is CH, CH2, CHF, CF2, O, S, SO, or SO2 A is adamantyl which can be optionally substituted with from zero to six substituents each independently selected from OR1, NR1R2, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, bicycloalkyl, bicycloalkylalkyl, alkylthioalkyl, arylalkylthioalkyl, cycloalkenyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl and cycloheteroalkylalkyl, all optionally substituted through available carbon atoms with 1, 2, 3, 4 or 5 groups selected from hydrogen, halo, alkyl, polyhaloalkyl, alkoxy, haloalkoxy, polyhaloalkoxy, alkoxycarbonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, polycycloalkyl, heteroarylamino, arylamino, cycloheteroalkyl, cycloheteroalkylalkyl, hydroxy, hydroxyalkyl, nitro, cyano, amino, substituted amino, alkylamino, dialkylamino, thiol, alkylthio, alkylcarbonyl, acyl, alkoxycarbonyl, aminocarbonyl, alkynylaminocarbonyl, alkylaminocarbonyl, alkenylaminocarbonyl, alkylcarbonyloxy, alkylcarbonylamino, arylcarbonylamino, alkylsulfonylamino, alkylaminocarbonylamino, alkoxycarbonylamino, alkylsulfonyl, aminosulfonyl, alkylsulfinyl, sulfonamido and sulfonyl;
R1 and R2 are each independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl;
including pharmaceutically acceptable salts thereof, and prodrug esters thereof, and all stereoisomers thereof, with the proviso that the compound of formula (I) is not selected from - View Dependent Claims (2, 3, 6, 7)
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4. A compound of the formula
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5. A compound of the formula
Specification