US2002161001A1PendingUtilityA1
Heterocyclic compounds, which are inhibitors of the enzyme DPP-IV
Priority: Jul 4, 2000Filed: Aug 22, 2001Published: Oct 31, 2002
Est. expiryJul 4, 2020(expired)· nominal 20-yr term from priority
C07D 473/08C07D 473/04A61P 43/00A61P 3/10A61P 3/04
44
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
The present invention relates to therapeutically active and selective inhibitors of the enzyme DPP-IV, pharmaceutical compositions comprising the compounds and the use of such compounds for and the manufacture of medicaments for treating diseases that are associated with proteins which are subject to inactivation by DPP-IV, such as type 2 diabetes and obesity, as well as methods for treating diseases that are associated with proteins which are subject to inactivation by DPP-IV, such as type 2 diabetes and obesity
Claims
exact text as granted — not AI-modified1 . A compound of formula I
wherein
n and m is one or two independently;
R 1 is C═O; C═S; C 1 -C 2 alkyl; C 2 alkenyl; C 2 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl; heteroaryl-C 1 -C 3 alkyl, wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl, or heteroaryl-C 1 -C 3 alkyl is optionally substituted with one or more R 4 independently;
R 2 is H; C 1 -C 7 alkyl; C 2 -C 7 alkenyl; C 2 -C 7 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl-C 1 -C 3 alkyl; heteroaryl; cyano; halogen; hydroxy, nitro; —SH; —SR 5 ; —SOR 5 ; —SO 2 R 5 ; carboxy; —CO 2 R 4 ; —CON(R 5 ) 2 ; C 1 -C 10 alkyloxy; C 2 -C 10 alkenyloxy; C 2 -C 10 alkynyloxy, aryloxy; heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl, heteroaryl-C 1 -C 3 alkyl, alkyloxy; alkenyloxy; alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R 11 independently;
R 3 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl-C 1 -C 3 alkyl; heteroaryl; C 1 -C 10 alkyl-O-C 1 -C 5 alkyl; carboxy; cyano; nitro; halogen; hydroxy; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl-C 1 -C 3 alkyl, heteroaryl, or alkyl-O-alkyl is optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system;
R 4 , R 11 , R 12 , and R 17 are independently C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl; cyano; halogen; hydroxy, nitro; trifluormethyl; N(R 13 ) 2 ; ═O; ═S; C 1 C 10 alkyloxy; C 2 -C 10 alkenyloxy; C 2 -C 10 alkynyloxy; aryloxy; heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, heteroaryl, alkyloxy; alkenyloxy; alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R 8 independently; two R 4 attached to the same carbon atom may form a spiroheterocyclic system, preferably hydantoine; thiohydantoine; oxazolidine-2,5-dione;
R 5 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 5 alkyl; heteroaryl; heteroaryl-C 1 -C 5 alkyl , wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl alkyl, heteroaryl, or heteroaryl alkyl is optionally substituted with one or more R 14 independently;
R 6 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R 15 independently;
R 7 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R 16 independently;
R 8 , R 14 , R 15 , and R 16 are independently H; nitro; —OCH 3 ; cyano; halogen; —OH; —SH; —SCH 3 ;
R 9 is H; halogen; C 1 -C 10 alkyl or aryl, wherein alkyl or aryl is optionally substituted with one or more R 17 independently
R 10 is H; halogen;
or, R 9 and R 10 may be connected to form a cyclopropyl ring;
R 13 is H; C 1 -C 10 alkyl or aryl;
or a salt thereof with a pharmaceutically acceptable acid or base;
with the exception of the following compounds:
1,3-dimethyl-7-(2-oxo-propyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
1,3,1′,3′,7′-pentamethyl-8-piperazin-1-yl-3,7,3′,7′-tetrahydro-7,8′-methanediyl-bis-purine-2,6-dione,
3,4,5-trimethoxy-benzoic acid 2-(1,3-dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydro-purin-7-yl)-ethyl ester,
7-[2-Hydroxy-3-(4-methoxy-phenoxy)-propyl]-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
7-[2-hydroxy-2-(4-nitro-phenyl)-ethyl]-3-methyl-8-piperazin-1-yl-3,7,8,9-tetrahydro-purine-2,6-dione,
7-Benzyl-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
7-(4-Chloro-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
7-(2-Chloro-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
7-Ethyl-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
3-Methyl-8-piperazin-1-yl-1,7-dipropyl-3,7-dihydro-purine-2,6-dione,
3-Methyl-7-(3-methyl-butyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
7-Butyl-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
3-Methyl-7-(3-phenyl-propyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
7-But-2-enyl-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
7-(3-Chloro-but-2-enyl)-3-methyl-8-piperazin- -yl-3,7-dihydro-purine-2,6-dione,
7-Heptyl-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
3-Methyl-7-(3-phenyl-ethyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
3-Methyl-7-(3-methyl-benzyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione,
3-Methyl-7-propyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione, and
3-Methyl-7-pentyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione.
2 . A compound of formula I
wherein
n and m is one or two independently;
with the proviso that if n is 2 then m is also 2;
R 1 is C═O; C═S; C 1 -C 2 alkyl; C 2 alkenyl; C 2 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl; heteroaryl-C 1 -C 3 alkyl, wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl, or heteroaryl-C 1 -C 3 alkyl is optionally substituted with one or more R 4 independently;
R 2 is H; C 1 -C 7 alkyl; C 2 -C 7 alkenyl; C 2 -C 7 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl-C 1 -C 3 alkyl; heteroaryl; cyano; halogen; hydroxy, nitro; —SH; —SR 5 ; —SOR 5 ; —SO 2 R 5 ; carboxy; —CO 2 R 4 ; —CON(R 5 ) 2 ; C 1 -C 10 alkyloxy; C 2 -C 10 alkenyloxy; C 2 -C 10 alkynyloxy, aryloxy; heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl, heteroaryl-C 1 -C 3 alkyl, alkyloxy; alkenyloxy; alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R 11 independently;
R 3 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl-C 1 -C 3 alkyl; heteroaryl; C 1 -C 10 alkyl-O-C 1 -C 5 alkyl; carboxy; cyano; nitro; halogen; hydroxy; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl-C 1 -C 3 alkyl, heteroaryl, or alkyl-O-alkyl is optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system;
R 4 , R 11 , R 12 , and R 17 are independently C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl; cyano; halogen; hydroxy, nitro; trifluormethyl; N(R 13 ) 2 ; ═O; ═S; C 1 -C 10 alkyloxy; C 2 -C 10 alkenyloxy; C 2 -C 10 alkynyloxy; aryloxy; heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, heteroaryl, alkyloxy; alkenyloxy; alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R 8 independently; two R 4 attached to the same carbon atom may form a spiroheterocyclic system, preferably hydantoine; thiohydantoine; oxazolidine-2,5-dione;
R 5 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 5 alkyl; heteroaryl; heteroaryl-C,-C 5 alkyl , wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl alkyl, heteroaryl, or heteroaryl alkyl is optionally substituted with one or more R 14 independently;
R 6 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R 15 independently;
R 7 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R 16 independently;
R 8 , R 14 , R 15 , and R 16 are independently H; nitro; —OCH 3 ; cyano; halogen; —OH; —SH; —SCH 3 ;
R 9 is H; halogen; C 1 -C 10 alkyl optionally substituted with one or more R 17 independently
R 10 is H; halogen;
or, R 9 and R 10 may be connected to form a cyclopropyl ring;
R 13 is H; C 1 -C 10 alkyl or aryl;
or a salt thereof with a pharmaceutically acceptable acid or base;
3 . A compound of formula I
wherein
n and m is one or two independently;
R 1 is C═O; C═S; C 1 -C 2 alkyl; C 2 alkenyl; C 2 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl; heteroaryl-C 1 -C 3 alkyl, wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl, or heteroaryl-C 1 -C 3 alkyl is optionally substituted with one or more R 4 independently;
R 2 is H; C 1 -C 7 alkyl; C 2 -C 7 alkenyl; C 2 -C 7 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl-C 1 -C 3 alkyl; heteroaryl; cyano; halogen; hydroxy, nitro; —SH; —SR 5 ; —SOR 5 ; —SO 2 R 5 ; carboxy; —CO 2 R 4 ; —CON(R 5 ) 2 ; C 1 -C 10 alkyloxy; C 2 -C 10 alkenyloxy; C 2 -C 10 alkynyloxy, aryloxy; heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl, heteroaryl-C 1 -C 3 alkyl, alkyloxy; alkenyloxy; alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R 11 independently;
R 3 is C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 3 alkyl; heteroaryl-C 1 -C 3 alkyl; heteroaryl; C 1 -C 10 alkyl-O-C 1 -C 5 alkyl; carboxy; cyano; nitro; halogen; hydroxy; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C 1 -C 3 alkyl, heteroaryl-C 1 -C 3 alkyl, heteroaryl, or alkyl-O-alkyl is optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system;
R 4 , R 11 , R 12 , and R 17 are independently C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl; cyano; halogen; hydroxy, nitro; trifluormethyl; N(R 13 ) 2 ; ═O; ═S; C 1 -C 10 alkyloxy; C 2 -C 10 alkenyloxy; C 2 -C 10 alkynyloxy; aryloxy; heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, heteroaryl, alkyloxy; alkenyloxy; alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R 8 independently; two R 4 attached to the same carbon atom may form a spiroheterocyclic system, preferably hydantoine; thiohydantoine; oxazolidine-2,5-dione;
R 5 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; aryl-C 1 -C 5 alkyl; heteroaryl; heteroaryl-C 1 -C 5 alkyl , wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl alkyl, heteroaryl, or heteroaryl alkyl is optionally substituted with one or more R 14 independently;
R 6 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R 15 independently;
R 7 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R 16 independently;
R 8 , R 14 , R 15 , and R 16 are independently H; nitro; —OCH 3 ; cyano; halogen; —OH; —SH; —SCH 3 ;
R 9 is H; halogen; C 1 -C 10 alkyl optionally substituted with one or more R 17 independently
R 10 is H; halogen;
or, R 9 and R 10 may be connected to form a cyclopropyl ring;
R 13 is H; C 1 -C 10 alkyl or aryl;
or a salt thereof with a pharmaceutically acceptable acid or base;
4 . A compound according to any one of the claims 1 to 3 wherein R 1 is C═O; C 1 -C 2 alkyl; C 2 alkenyl; C 2 alkynyl ; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; or heteroaryl, wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R 4 independently.
5 . A compound according to claim 4 wherein R 1 is C═O; C 1 -C 2 alkyl; C 3 -C 7 cycloalkyl; aryl; or heteroaryl, wherein each alkyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more R 4 independently.
6 . A compound according to claim 5 wherein R 1 is C═O or aryl optionally substituted with one or more R 4 independently.
7 . A compound according to claim 6 wherein R 1 is aryl optionally substituted with one or more R 4 independently.
8 . A compound according to claim 7 wherein R 1 is aryl.
9 . A compound according to claim 8 wherein R 1 is phenyl.
10 . A compound according to any one of the claims 1 to 9 wherein R 2 is H; C 1 -C 7 alkyl; C 2 -C 7 alkenyl; C 2 -C 7 alkynyl; C 3 -C 7 cycloalkyl; C 3 -C 7 cycloheteroalkyl; aryl; heteroaryl; cyano; halogen; hydroxy, nitro; —SH; —SR 5 ; —SOR 5 ; —SO 2 R 5 ; —CO 2 R 4 ; C 1 -C 10 alkyloxy; C 2 -C 10 alkenyloxy; C 2 -C 10 alkynyloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, heteroaryl, alkyloxy, alkenyloxy, or alkynyloxy is optionally substituted with one or more R 11 independently.
11 . A compound according to claim 10 wherein R 2 is H; C 1 -C 7 alkyl; C 3 -C 7 cycloheteroalkyl; aryl; cyano; halogen; nitro; —SR 5 ; —SO 2 R 5 ; —CO 2 R 4 ; or C 1 -C 10 alkyloxy; wherein each alkyl, cycloheteroalkyl, aryl, or alkyloxy is optionally substituted with one or more R 11 independently.
12 . A compound according to claim 11 wherein R 2 is H; C 1 -C 7 alkyl; C 3 -C 7 cycloheteroalkyl; aryl; cyano; halogen; —CO 2 R 4 ; or C 1 -C 10 alkyloxy; wherein each alkyl, cycloheteroalkyl, aryl, or alkyloxy is optionally substituted with one or more R 11 independently.
13 . A compound according to claim 12 wherein R 2 is H; C 1 -C 7 alkyl; cyano; halogen; or C 1 -C 10 alkyloxy; wherein each alkyl or alkyloxy is optionally substituted with one or more R 11 independently.
14 . A compound according to claim 13 wherein R 2 is H; cyano or halogen.
15 . A compound according to claim 14 wherein R 2 is H.
16 . a compound according to any one of the claims 1 , 2 and 4 to 15 wherein R 3 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; aryl; C 1 -C 10 alkyl-O-C 1 -C 5 alkyl; cyano; nitro; halogen; hydroxy; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or alkyl-O-alkyl is optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system.
17 . A compound according to claim 16 wherein R 3 is H; C 1 -C 10 alkyl; C 1 -C 10 alkyl-O-C 1 -C 5 alkyl; hydroxy; wherein alkyl, or alkyl-O-alkyl is optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system.
18 . A compound according to claim 17 wherein R 3 is H or C 1 -C 10 alkyl optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system.
19 . A compound according to claim 18 wherein R 3 is H or C 1 -C 10 alkyl.
20 . A compound according to claim 19 wherein R 3 is methyl, ethyl, or isopropyl.
21 . A compound according to claim 19 wherein R 3 is H.
22 . A compound according to claim 3 wherein R 3 is C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; aryl; C 1 -C 10 alkyl-O-C 1 -C 5 alkyl; cyano; nitro; halogen; hydroxy; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or alkyl-O-alkyl is optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system.
23 . A compound according to claim 22 wherein R 3 is C 1 -C 10 alkyl; C 1 -C 10 alkyl-O-C 1 -C 5 alkyl; hydroxy; wherein alkyl, or alkyl-O-alkyl is optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system.
24 . A compound according to claim 23 wherein R 3 is C 1 -C 10 alkyl optionally substituted with one or more R 12 independently; two R 3 attached to the same carbon atom may form a spiro system.
25 . A compound according to claim 24 wherein R 3 is C 1 -C 10 alkyl.
26 . A compound according to claim 30 wherein R 3 is methyl, ethyl, or isopropyl
27 . A compound according to any one of the claims 1 to 26 wherein R 4 is C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; aryl; heteroaryl; cyano; halogen; hydroxy, nitro; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more R 8 independently.
28 . A compound according to claim 27 wherein R 4 is C 1 -C 10 alkyl; C 2 -C 10 alkenyl; or C 2 -C 10 alkynyl; wherein each alkyl, alkenyl, or alkynyl is optionally substituted with one or more R 8 independently.
29 . A compound according to claim 28 wherein R 4 is C 1 -C 10 alkyl optionally substituted with one or more R 8 independently.
30 . A compound according to claim 29 wherein R 4 is C 1 -C 10 alkyl.
31 . A compound according to claim 30 wherein R 4 is methyl.
32 . A compound according to any one of the claims 1 to 31 wherein R 5 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; aryl; heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more R 14 independently.
33 . A compound according to claim 32 wherein R 5 is C 1 -C 10 alkyl or aryl; wherein each alkyl or aryl is optionally substituted with one or more R 14 independently.
34 . A compound according to any one of the claims 1 to 33 wherein R 6 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; C 3 -C 7 cycloalkyl; or aryl; wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, or aryl is optionally substituted with one or more R 15 independently.
35 . A compound according to claim 34 wherein R 6 is H; C 1 -C 10 alkyl; or C 2 -C 10 alkenyl; wherein each each alkyl or alkenyl is optionally substituted with one or more R 15 independently.
36 . A compound according to claim 35 wherein R 6 is H or C 1 -C 10 alkyl optionally substituted with one or more R 15 independently.
37 . A compound according to claim 36 wherein R 6 is H.
38 . A compound according to claim 36 wherein R 6 is C 1 -C 10 alkyl optionally substituted with one or more R 15 independently.
39 . A compound according to claim 38 wherein R 6 is C 1 -C 10 alkyl.
40 . A compound according to claim 39 wherein R 6 is methyl.
41 . A compound according to any one of the claims 1 to 40 wherein R 7 is H; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; or C 2 -C 10 alkynyl, wherein each each alkyl, alkenyl, or alkynyl is optionally substituted with one or more R 16 independently.
42 . A compound according to claim 41 wherein R 7 is C 1 -C 10 alkyl optionally substituted with one or more R 16 independently.
43 . A compound according to claim 42 wherein R 7 is C 1 -C 10 alkyl.
44 . A compound according to any one of the claims 1 to 43 wherein R 8 is —OCH 3 .
45 . A compound according to any one of the claims 1 to 44 wherein R 9 is aryl.
46 . A compound according to any one of the claims 1 to 45 wherein R 11 is C 1 -C 10 alkyl; aryl; cyano; halogen; wherein each alkyl or aryl is optionally substituted with one or more R 8 independently.
47 . A compound according to claim 46 wherein R 11 is halogen.
48 . A compound according to any one of the claims 1 to 47 wherein R 12 is C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 2 -C 10 alkynyl; aryl; heteroaryl; cyano; halogen; hydroxy, nitro; wherein each alkyl, alkenyl, alkynyl, aryl, heteroaryl is optionally substituted with one or more R 8 independently.
49 . A compound according to claim 48 wherein R 12 is aryl; heteroaryl; or hydroxy; wherein each aryl and heteroaryl is optionally substituted with one or more R 8 independently.
50 . A compound according to claim 49 wherein R 12 is phenyl, pyridyl, or pyrrolidinyl.
51 . A compound according to claim 49 wherein R 12 is hydroxy.
52 . A compound according to any one of the claims 1 to 51 wherein R 14 is halogen.
53 . A compound that fulfils all of the following three criteria:
1. Contains the structural element of Formula III wherein
n and m is one or two independently;
2. has a molecular weight of 500 daltons or less; 3. has a DPP-IV inhibition constant Ki of 500 nM or less
54 . A compound according to any one of the preceding claims selected from the following:
7-Benzyl-8-(6-hydroxymethyl-[1,4]diazepan-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione. 7-Benzyl-8-(6-hydroxy-[1,4]diazepan-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 7-Benzyl-8-(3-hydroxymethyl-[1,4]diazepan-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 7-Benzyl-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 1,3-Dimethyl-7-(4-methylbenzyl)-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 3-(1,3-Dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydropurin-7-ylmethyl) benzonitrile 2-(1,3-Dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydropurin-7-ylmethyl) benzonitrile 1,3-Dimethyl-7-(1-phenylethyl)-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 7-(2-Iodobenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 1,3-Dimethyl-8-piperazin-1-yl-7-(2-trifluoromethylbenzyl)-3,7-dihydropurine-2,6-dione 1,3-Dimethyl-7-naphthalen-1-ylmethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 1,3-Dimethyl-7-naphthalen-2-ylmethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 7-(3-Bromobenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 7-Benzyl-8-(3-isopropylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 1,3-Dimethyl-7-(2-oxo-2-pyrrolidin-1-yl-ethyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 2-(8-[1,4]Diazepan-1-yl-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl)-benzonitrile 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 7-(2-Difluoromethoxy-benzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 7-(2,3-Dimethoxy-benzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 1,3-Dimethyl-8-piperazin-1-yl-7-(2-trifluoromethoxy-benzyl)-3,7-dihydro-purine-2,6-dione 1,3-Dimethyl-8-piperazin-1-yl-7-(2-trifluoromethylsulfanyl-benzyl)-3,7-dihydro-purine-2,6-dione 4-(1,3-Dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydro-purin-7-yl)-butyronitrile R)-7-Benzyl-8-(3-isopropylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione S)-7-Benzyl-8-(3-isopropylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 7-Benzyl-8-(6,9-diazaspiro[4.5]dec-9-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 7-Benzyl-8-(piperazin-3-spiro-3′-bicyclo[2,2,1]heptane-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-methoxy-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1,3-dimethyl-7-naphthalen-1-ylmethyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-fluoro-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1,3-dimethyl-7-(2-methyl-benzyl)-3,7-dihydro-purine-2,6-dione 7-(2-Chloro-benzyl)-8-[1,4]diazepan-1-yl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 7-(2-Bromo-benzyl)-8-[1,4]diazepan-1-yl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1,3-dimethyl-7-(2-trifluoromethyl-benzyl)-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1,3-dimethyl-7-(2-nitro-benzyl)-3,7-dihydro-purine-2,6-dione 3-Benzyl-8-piperazin-1-yl-7-(2-trifluoromethyl-benzyl)-3,7-dihydro-purine-2,6-dione 3,7-Dibenzyl-1-(2-hydroxy-ethyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 3-Benzyl-7-phenethyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 3,7-Dibenzyl-8-[1,4]diazepan-1-yl-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-3,7-dihydro-purine-2,6-dione 3,7-Dibenzyl-8-[1,4]diazepan-1-yl-1-propyl-3,7-dihydro-purine-2,6-dione 3,7-Dibenzyl-8-[1,4]diazepan-1-yl-1-(2-hydroxy-ethyl)-3,7-dihydro-purine-2,6-dione 2-(3,7-Dibenzyl-8-[1,4]diazepan-1-yl-2,6-dioxo-2,3,6,7-tetrahydro-purin-1-yl)-N,N-diethyl-acetamide 1,3,7-Tribenzyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 1,3,7-Tribenzyl-8-[1,4]diazepan-1-yl-3,7-dihydro-purine-2,6-dione (S)-7-Benzyl-8-(3-benzyloxymethylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 3,7-Dibenzyl-8-piperazin-1-yl-1-propyl-3,7-dihydro-purine-2,6-dione 3,7-Dibenzyl-8-[1,4]diazepan-1-yl-1-propyl-3,7-dihydro-purine-2,6-dione 3,7-Dibenzyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 3,7-Dibenzyl-8-[1,4]diazepan-1-yl-3,7-dihydro-purine-2,6-dione 2-(3-Benzyl-2,6-dioxo-8-piperazin-1-yl-1-propyl-1,2,3,6-tetrahydro-purin-7-ylmethyl)-benzonitrile 2-(3-Benzyl-8-[1,4]diazepan-1-yl-2,6-dioxo-1-propyl-1,2,3,6-tetrahydro-purin-7-ylmethyl)-benzonitrile 2-(3-Benzyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydro-purin-7-ylmethyl)-benzonitrile 2-(3-Benzyl-8-[1,4]diazepan-1-yl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl)-benzonitrile 3-Benzyl-7-(2-iodo-benzyl)-8-piperazin-1-yl-1-propyl-3,7-dihydro-purine-2,6-dione 3-Benzyl-8-[1,4]diazepan-1-yl-7-(2-iodo-benzyl)-1-propyl-3,7-dihydro-purine-2,6-dione 3-Benzyl-7-(2-iodo-benzyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 3-Benzyl-8-[1,4]diazepan-1-yl-7-(2-iodo-benzyl)-3,7-dihydro-purine-2,6-dione 7-Benzyl-3-methyl-8-piperazin-1-yl-1-propyl-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-1-propyl-3,7-dihydro-purine-2,6-dione 7-Benzyl-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-3,7-dihydro-purine-2,6-dione 2-(3-Methyl-2,6-dioxo-8-piperazin-1-yl-1-propyl-1,2,3,6-tetrahydro-purin-7-ylmethyl)-benzonitrile 2-(8-[1,4]Diazepan-1-yl-3-methyl-2,6-dioxo-1-propyl-1,2,3,6-tetrahydro-purin-7-ylmethyl)-benzonitrile 2-(8-[1,4]Diazepan-1-yl-3-methyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl)-benzonitrile 7-(2-Iodo-benzyl)-3-methyl-8-piperazin-1-yl-1-propyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-3-methyl-1-propyl-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 3-Benzyl-8-[1,4]diazepan-1-yl-(3-hydroxy-propyl)-7-(2-iodo-benzyl)-3,7-dihydro-purine-2,6-dione 3-Benzyl-8-[1,4]diazepan-1-yl-1-(2-ethoxy-ethyl)-7-(2-iodo-benzyl)-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-1-(3-phenyl-allyl)-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-1-(2-oxo-2-phenyl-ethyl)-3,7-dihydro-purine-2,6-dione 2-(7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-purin-1-ylmethyl)-benzonitrile (7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-purin-1-yl)-acetonitrile 3-Methyl-7-(2-methyl-thiazol-4-ylmethyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-3-methyl-7-(2-methyl-thiazol-4-ylmethyl)-3,7-dihydro-purine-2,6-dione 3-Methyl-7-(2-oxo-2-phenyl-ethyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-3-methyl-7-(2-oxo-2-phenyl-ethyl)-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-3-methyl-7-phenethyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(3-hydroxy-propyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 1-(3-Hydroxy-propyl)-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(2-ethoxy-ethyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 1-(2-Ethoxy-ethyl)-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-3-methyl-1-(2-phenoxy-ethyl)-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-1-[2-(2-methoxy-ethoxy)-ethyl]-3-methyl-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-1-[2-(2-methoxy-ethoxy)-ethyl]-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(3,5-dimethoxy-benzyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-1-(3-methoxy-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 7-Biphenyl-2-ylmethyl-8-[1,4]diazepan-1-yl-3-methyl-3,7-dihydro-purine-2,6-dione 7-(2-Bromo-benzyl)-8-[1,4]diazepan-1-yl-3-methyl-3,7-dihydro-purine-2,6-dione 7-(2-Chloro-benzyl)-8-[1,4]diazepan-1-yl-3-methyl-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-(3,5-dimethyl-piperazin-1-yl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 7-(4-Methoxybenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione (1,3-Dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydropurin-7-yl)-phenylacetic acid methyl ester 7-(5-Chloro-2-nitrobenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 4-(1,3-Dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydropurin-7-ylmethyl) benzonitrile 7-(4-Methanesulfonylbenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 7-(2-Fluoro-6-nitrobenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 7-(4-Benzyloxybenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 7-(2,4-Dichlorobenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 1,3-Dimethyl-8-piperazin-1-yl-7-(4-trifluoromethylbenzyl)-3,7-dihydropurine-2,6-dione 7-Biphenyl-4-ylmethyl-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 3-(1,3-Dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydropurin-7-ylmethyl) benzoic acid methyl ester 4-(1,3-Dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydropurin-7-ylmethyl) benzoic acid methyl ester 7-Biphenyl-2-ylmethyl-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 7-(4-tert-Butylbenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 1,3-Dimethyl-8-piperazin-1-yl-7-(4-trifluoromethoxybenzyl)-3,7-dihydropurine-2,6-dione 7-(3,4-Dichlorobenzyl)-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydropurine-2,6-dione 1,3-Dimethyl-8-piperazin-1-yl-7-(4-[1,2,3]thiadiazol-4-ylbenzyl)-3,7-dihydropurine-2,6-dione 4-(1,3-Dimethyl-2,6-dioxo-8-piperazin-1-yl-1,2,3,6-tetrahydropurin-7-ylmethyl)-3-methoxybenzoic acid methyl ester 7-Cyclohexylmethyl-1,3-dimethyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 8-(6-Benzyl-[1,4]diazepan-1-yl)-7-(2-iodo-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione (S)-7-Benzyl-8-(3-hydroxymethylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 8-[1,4]Diazepan-1-yl-1,3-dimethyl-7-(2-oxo-2-pyrrolidin-1-yl-ethyl)-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-1,3-dimethyl-8-(6-pyridin-2-ylmethyl-[1,4]diazepan-1-yl)-3,7-dihydro-purine-2,6-dione 7-(2-Bromo-benzyl)-1,3-dimethyl-8-(6-pyridin-2-ylmethyl-[1,4]diazepan-1-yl)-3,7-dihydro-purine-2,6-dione (S) 7-Benzyl-8-(3-benzyl-piperazin-1-yl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 7-Benzyl-1,3-dimethyl-8-(3-phenethyl-piperazin-1-yl)-3,7-dihydro-purine-2,6-dione (R)-7-Benzyl-8-(3-benzylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione 7-Benzyl-8-(3-(2-hydroxy-benzyl)-piperazin-1-yl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-(3-(2-methoxy-benzyl)-piperazin-1-yl)1,3-dimethyl-3,7-dihydro-purine-2,6-dione (R) 7-Benzyl-8-(3-(4-methoxy-benzyl)-piperazin-1-yl)1,3-dimethyl-3,7-dihydro-purine-2,6-dione (R)-7-Benzyl-8-(3-(4-hydroxy-benzyl)-piperazin-1-yl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione (R)-7-Benzyl-1,3-dimethyl-8-(3-(4-nitro-benzyl)-piperazin-1-yl)-3,7-dihydro-purine-2,6-dione (R)-7-Benzyl-8-(3-(4-fluoro-benzyl)-piperazin-1-yl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione (R)-4-(4-(7-Benzyl-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-piperazin-2-ylmethyl)-benzonitrile (R)-6-(8-(3-Benzyl-piperazin-1-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl)-nicotinonitrile (R)-7-Benzyl-1,3-dimethyl-8-(3-thiazol-4-ylmethyl-piperazin-1-yl)-3,7-dihydro-purine-2,6-dione (R)-2-[1,3-Dimethyl-2,6-dioxo-8-(3-thiophen-2-ylmethyl-piperazin-1-yl)-1,2,3,6-tetrahydro-purin-7-ylmethyl]-benzonitrile 7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-1-(tetrahydro-furan-2-ylmethyl)-3,7-dihydro-purine-2,6-dione 7-Benzyl-1-(2-cyclohexyl-ethyl)-8-[1,4]diazepan-1-yl-3-methyl-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-1-(5-methyl-hexyl)-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-3-methyl-1-(3-methyl-butyl)-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-1-(2-ethoxy-ethyl)-3-methyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-3-methyl-1-(tetrahydro-furan-2-ylmethyl)-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-3-methyl-8-piperazin-1-yl-1-(tetrahydro-furan-2-ylmethyl)-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-3-methyl-1-(tetrahydro-pyran-2-ylmethyl)-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-3-methyl-8-piperazin-1-yl-1-(tetrahydro-pyran-2-ylmethyl)-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-3-methyl-1-(2-phenoxy-ethyl)-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-1-(2-methoxy-ethyl)-3-methyl-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-1-(2-methoxy-ethyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 1-(2-Benzyloxy-ethyl)-8-[1,4]diazepan-1-yl-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 1-(2-Benzyloxy-ethyl)-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 1-(3,5-Dimethoxy-benzyl)-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-1-(3-methoxy-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-3-methyl-1-(3-trifluoromethoxy-benzyl)-3,7-dihydro-purine-2,6-dione 7-(2-Iodo-benzyl)-3-methyl-8-piperazin-1-yl-1-(3-trifluoromethoxy-benzyl)-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(2-hydroxy-propyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(2,2-diethoxy-ethyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(2,2-dimethoxy-ethyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(2-[1,3]dioxolan-2-yl-ethyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 1-(2-[1,3]Dioxolan-2-yl-ethyl)-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 1-[1,3]Dioxolan-2-ylmethyl-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(2-[1,3]dioxan-2-yl-ethyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 1-(2-[1,3]Dioxan-2-yl-ethyl)-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(2,3-dihydroxy-propyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 1-(2,3-Dihydroxy-propyl)-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(3-hydroxy-2-methyl-propyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 1-(3-Hydroxy-2-methyl-propyl)-7-(2-iodo-benzyl)-3-methyl-8-piperazin-1-yl-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-7-(2-iodo-benzyl)-3-methyl-1-[3-(tetrahydro-pyran-2-yloxy)-propyl]-3,7-dihydro-purine-2,6-dione 8-[1,4]Diazepan-1-yl-1-(2-fluoro-ethyl)-7-(2-iodo-benzyl)-3-methyl-3,7-dihydro-purine-2,6-dione 7-Benzyl-8-[1,4]diazepan-1-yl-1-(3-hydroxy-propyl)-3-methyl-3,7-dihydro-purine-2,6-dione 7-Biphenyl-2-ylmethyl-8-[1,4]diazepan-1-yl-3-methyl-3,7-dihydro-purine-2,6-dioneJoin the waitlist — get patent alerts
Track US2002161001A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.