Back to results
US 2002/0161001 A1Published application
Heterocyclic compounds, which are inhibitors of the enzyme DPP-IV
OwnerAnders Bendtz Kanstrup, Lise Brown Christiansen +3inventors
InventorsAnders Bendtz Kanstrup, Lise Brown Christiansen, Jane Marie Lundbeck, Christian K. Sams, Marit Kristiansen
Life of this patent
Estimating the term…
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
Claims54
A compound of formula I
- 264
- wherein
- n and m is one or two independently;
- R1 is C═O;
- C═S;
- C1-C2 alkyl;
- C2 alkenyl;
- C2 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl;
- heteroaryl-C1-C3 alkyl, wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl, or heteroaryl-C1-C3 alkyl is optionally substituted with one or more R4 independently;
- R2 is H;
- C1-C7 alkyl;
- C2-C7 alkenyl;
- C2-C7 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl-C1-C3 alkyl;
- heteroaryl;
- cyano;
- halogen;
- hydroxy, nitro;
- —SH;
- —SR5;
- —SOR5;
- —SO2R5;
- carboxy;
- —CO2R4;
- —CON(R5)2;
- C1-C10 alkyloxy;
- C2-C10 alkenyloxy;
- C2-C10 alkynyloxy, aryloxy;
- heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, alkyloxy;
- alkenyloxy;
- alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R11 independently;
- R3 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl-C1-C3 alkyl;
- heteroaryl;
- C1-C10alkyl-O-C1-C5alkyl;
- carboxy;
- cyano;
- nitro;
- halogen;
- hydroxy;
- wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl-C1-C3 alkyl, heteroaryl, or alkyl-O-alkyl is optionally substituted with one or more R12 independently;
- two R3 attached to the same carbon atom may form a spiro system;
- R4, R11, R12, and R17 are independently C1-C10 alkyl;
- C2-C10alkenyl;
- C2-C10alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl;
- cyano;
- halogen;
- hydroxy, nitro;
- trifluormethyl;
- N(R13)2;
- ═O;
- ═S;
- C1C10 alkyloxy;
- C2-C10 alkenyloxy;
- C2-C10 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 R8 independently;
- two R4 attached to the same carbon atom may form a spiroheterocyclic system, preferably hydantoine;
- thiohydantoine;
- oxazolidine-2,5-dione;
- R5 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C5 alkyl;
- heteroaryl;
- heteroaryl-C1-C5 alkyl , wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl alkyl, heteroaryl, or heteroaryl alkyl is optionally substituted with one or more R14 independently;
- R6 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R15 independently;
- R7is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R16 independently;
- R8, R14, R15, and R16 are independently H;
- nitro;
- —OCH3;
- cyano;
- halogen;
- —OH;
- —SH;
- —SCH3;
- R9 is H;
- halogen;
- C1-C10 alkyl or aryl, wherein alkyl or aryl is optionally substituted with one or more R17 independently
- R10 is H;
- halogen;
- or, R9 and R10 may be connected to form a cyclopropyl ring;
- R13 is H;
- C1-C10 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.
143 more elements
A compound of formula I
- 265
- wherein
- n and m is one or two independently;
- with the proviso that if n is 2 then m is also 2;
- R1 is C═O;
- C═S;
- C1-C2 alkyl;
- C2 alkenyl;
- C2 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl;
- heteroaryl-C1-C3 alkyl, wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl, or heteroaryl-C1-C3 alkyl is optionally substituted with one or more R4 independently;
- R2 is H;
- C1-C7 alkyl;
- C2-C7 alkenyl;
- C2-C7 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl-C1-C3 alkyl;
- heteroaryl;
- cyano;
- halogen;
- hydroxy, nitro;
- —SH;
- —SR5;
- —SOR5;
- —SO2R5;
- carboxy;
- —CO2R4;
- —CON(R5)2;
- C1-C10 alkyloxy;
- C2-C10 alkenyloxy;
- C2-C10 alkynyloxy, aryloxy;
- heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, alkyloxy;
- alkenyloxy;
- alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R11 independently;
- R3 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl-C1-C3 alkyl;
- heteroaryl;
- C1-C10alkyl-O-C1-C5alkyl;
- carboxy;
- cyano;
- nitro;
- halogen;
- hydroxy;
- wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl-C1-C3 alkyl, heteroaryl, or alkyl-O-alkyl is optionally substituted with one or more R12 independently;
- two R3 attached to the same carbon atom may form a spiro system;
- R4, R11, R12, and R17 are independently C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl;
- cyano;
- halogen;
- hydroxy, nitro;
- trifluormethyl;
- N(R13)2;
- ═O;
- ═S;
- C1-C10 alkyloxy;
- C2-C10 alkenyloxy;
- C2-C10 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 R8 independently;
- two R4 attached to the same carbon atom may form a spiroheterocyclic system, preferably hydantoine;
- thiohydantoine;
- oxazolidine-2,5-dione;
- R5 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C5 alkyl;
- heteroaryl;
- heteroaryl-C,-C5 alkyl , wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl alkyl, heteroaryl, or heteroaryl alkyl is optionally substituted with one or more R14 independently;
- R6 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R15 independently;
- R7 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R16 independently;
- R8, R14, R15, and R16 are independently H;
- nitro;
- —OCH3;
- cyano;
- halogen;
- —OH;
- —SH;
- —SCH3;
- R9 is H;
- halogen;
- C1-C10 alkyl optionally substituted with one or more R17 independently
- R10 is H;
- halogen;
- or, R9 and R10 may be connected to form a cyclopropyl ring;
- R13 is H;
- C1-C10 alkyl or aryl;
- or a salt thereof with a pharmaceutically acceptable acid or base;
123 more elements
A compound of formula I
- 266
- wherein
- n and m is one or two independently;
- R1 is C═O;
- C═S;
- C1-C2 alkyl;
- C2 alkenyl;
- C2 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl;
- heteroaryl-C1-C3 alkyl, wherein each alkyl, alkenyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl, or heteroaryl-C1-C3 alkyl is optionally substituted with one or more R4 independently;
- R2 is H;
- C1-C7 alkyl;
- C2-C7 alkenyl;
- C2-C7 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl-C1-C3 alkyl;
- heteroaryl;
- cyano;
- halogen;
- hydroxy, nitro;
- —SH;
- —SR5;
- —SOR5;
- —SO2R5;
- carboxy;
- —CO2R4;
- —CON(R5)2;
- C1-C10 alkyloxy;
- C2-C10 alkenyloxy;
- C2-C10 alkynyloxy, aryloxy;
- heteroaryloxy, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, alkyloxy;
- alkenyloxy;
- alkynyloxy, aryloxy, or heteroaryloxy is optionally substituted with one or more R11 independently;
- R3 is C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C3 alkyl;
- heteroaryl-C1-C3 alkyl;
- heteroaryl;
- C1-C10alkyl-O-C1-C5alkyl;
- carboxy;
- cyano;
- nitro;
- halogen;
- hydroxy;
- wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl-C1-C3 alkyl, heteroaryl-C1-C3 alkyl, heteroaryl, or alkyl-O-alkyl is optionally substituted with one or more R12 independently;
- two R3 attached to the same carbon atom may form a spiro system;
- R4, R11, R12, and R17 are independently C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl;
- cyano;
- halogen;
- hydroxy, nitro;
- trifluormethyl;
- N(R13)2;
- ═O;
- ═S;
- C1-C10 alkyloxy;
- C2-C10 alkenyloxy;
- C2-C10 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 R8 independently;
- two R4 attached to the same carbon atom may form a spiroheterocyclic system, preferably hydantoine;
- thiohydantoine;
- oxazolidine-2,5-dione;
- R5 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- aryl-C1-C5 alkyl;
- heteroaryl;
- heteroaryl-C1-C5 alkyl , wherein each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, aryl alkyl, heteroaryl, or heteroaryl alkyl is optionally substituted with one or more R14 independently;
- R6 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R15 independently;
- R7 is H;
- C1-C10 alkyl;
- C2-C10 alkenyl;
- C2-C10 alkynyl;
- C3-C7 cycloalkyl;
- C3-C7 cycloheteroalkyl;
- aryl;
- heteroaryl, wherein each each alkyl, alkenyl, alkynyl, cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl is optionally substituted with one or more R16 independently;
- R8, R14, R15, and R16 are independently H;
- nitro;
- —OCH3;
- cyano;
- halogen;
- —OH;
- —SH;
- —SCH3;
- R9 is H;
- halogen;
- C1-C10 alkyl optionally substituted with one or more R17 independently
- R10 is H;
- halogen;
- or, R9 and R10 may be connected to form a cyclopropyl ring;
- R13 is H;
- C1-C10 alkyl or aryl;
- or a salt thereof with a pharmaceutically acceptable acid or base;
121 more elements
A compound according to claim 30 wherein R3 is methyl, ethyl, or isopropyl
A compound that fulfils all of the following three criteria:
- 1. Contains the structural element of Formula III
- 267
- 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
3 more elements
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-dione
162 more elements
Dependencies are inferred from the claim text.