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US 2010/0144758 A1Published application
Azaindole p2x3 and p2x2/3 modulators
OwnerMichael Patrick Dillon, Daisy Joe Du Bois +3inventors
InventorsMichael Patrick Dillon, Daisy Joe Du Bois, Yingjie Lai, Ronald Charles Hawley, Beihan Wang
Life of this patent
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Abstract
The application discloses compounds of the Formula I: or a pharmaceutically acceptable salt thereof, wherein, X, R1, R2 R3, R4, R5, R6, R7 and R8 are as defined herein. Also provided are methods of using the compounds for treating diseases associated with the P2X3 and/or a P2X2/3 receptor antagonist and methods of making the compounds.
Claims23
A compound of Formula I
- wherein:
- X is CX1aX1bCHX1cOX1d;
- X1a and X1b are independently H, lower alkyl, or lower hydroxy alkyl;
- X1b is H, lower alkyl, lower alkoxy, lower hydroxyalkyl, or hydroxy lower alkoxy;
- or X1b and X1c together form tetrahydrofuranyl;
- X1d is H, lower alkyl, or lower alkoxy;
- each of R1, R2, R3, and R4 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, amido, sulfonamido, or lower haloalkyl;
- and
- each of R5, R6, R7, and R8 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl;
- with the proviso that R1, R2, R3, and R4 are not all H.
7 more elements
A compound of Formula II
- wherein:
- X is CHX1aCHX1bCHX1cOX1d;
- X1a is H, lower alkyl, or lower hydroxy alkyl;
- X1b is H, H lower alkyl, lower alkoxy, lower hydroxyalkyl, or hydroxy lower alkoxy;
- X1c is H, lower alkyl, lower alkoxy, lower hydroxyalkyl, or hydroxy lower alkoxy;
- X1d is H, lower alkyl, lower alkoxy, lower haloalkyl, or lower hydroxyalkyl;
- or X1c and X1d together form tetrahydrofuranyl;
- each of R1, R2, and R3 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, amido, sulfonamido, or lower haloalkyl;
- and
- each of R4, R5, and R6 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl;
- with the proviso that each of R1, R2, and R3 are not H.
8 more elements
A compound of Formula III
- wherein:
- X is NX′ or CH(OH);
- X′ is H or lower alkyl;
- each of R1, R2, R3, and R4 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, lower thioalkyl, amido, sulfonamido, or lower haloalkyl;
- and
- each of R5, R6, R7, and R8 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl.
3 more elements
A compound of Formula IV
- wherein:
- X is CH2CH2CH2OX1;
- X1 is H, lower alkyl, lower haloalkyl, or lower hydroxy alkyl;
- each of R1, R2, and R3 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, amido, sulfonamido, or lower haloalkyl;
- and
- each of R4, R5, and R6 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl;
- with the proviso that when each of R1, R2, and R3 are H, X1 is not H, methyl, ethyl or isopropyl.
4 more elements
A compound of Formula V
- wherein:
- X is CH2CH2X1;
- X1 is heterocycloalkyl or heteroaryl, optionally substituted with one or more X1′;
- X1′ is lower alkyl or oxo;
- each of R1, R2, and R3 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, amido, sulfonamido, or lower haloalkyl;
- and
- each of R4, R5, and R6 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl;
- and
- with the proviso that when each of R1, R2, and R3 are H, X1 is not morpholine.
6 more elements
A compound of Formula VI
- wherein:
- X is CH2CH2CH2X1;
- X1 is heterocycloalkyl or heteroaryl, optionally substituted with one or more X1′;
- X1′ is lower alkyl or oxo;
- each of R1, R2, and R3 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, amido, sulfonamido, or lower haloalkyl;
- and
- each of R4, R5, and R6 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl;
- with the proviso that when each of R1, R2, and R3 are H, Xl is not morpholine, pyrrolidin-2-one, or imidazole.
5 more elements
A compound of Formula VII
- wherein:
- X is C(═O)X1;
- X1 is lower alkyl or lower alkoxy;
- each of R1, R2, and R3 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, amido, sulfonamido, or lower haloalkyl;
- and
- each of R4, R5, and R6 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl.
3 more elements
A compound of Formula VIII
- wherein:
- R1 is H, halogen, hydroxy, or R′;
- R′ is lower alkyl, phenyl, lower alkoxy, lower haloalkyl, lower hydroxyalkyl, lower alkenyl, lower alkynyl, phenyl lower alkynyl, lower alkoxy, cycloalkenyl, lower alkyl phenylalkyl, aryl, heteroaryl, or alkylheteroaryl, optionally substituted with one or more R″;
- R″ is lower alkyl, halogen, hydroxy, lower alkoxy, amino, lower haloalkyl, or lower hydroxyalkyl;
- and
- each of R2, R3, and R4 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl.
3 more elements
A compound of Formula IX
- wherein:
- each of R1, R2, and R3 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, amido, sulfonamido, or lower haloalkyl;
- and
- each of R4, R5, and R6 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl;
- and
- R7 is lower alkyl, lower alkoxy, or lower hydroxyalkyl.
3 more elements
A compound of Formula X
- wherein:
- X is CHX1aCHX1bOX1c;
- X1a and X1b are each independently H, lower alkyl, hydroxy, lower alkoxy, or lower hydroxy alkyl;
- X1c is H, lower alkyl, lower hydroxyalkyl, or lower alkoxy;
- each of R1, R2, R3, and R4 is independently H, halogen, lower alkyl, hydroxy, lower alkoxy, amido, sulfonamido, or lower haloalkyl;
- and
- each of R5, R6, R7, and R8 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl;
- with the proviso that when each of R1, R2, R3, and R4 are H and X1c is H, than either X1a is methyl, isopropyl, or lower hydroxyalkyl;
- and
- with the further proviso that when each of R1, R2, R3, and R4 are H and X1c is methyl, then either R5 or R7 is fluoro, lower alkoxy, or tert-butyl;
- or both R5 and R7 are not H;
- or R6 is lower haloalkyl or heterocycloalkyl;
- or R7 is methyl and R6 is halogen or lower alkoxy;
- or R8 is fluoro;
- or X1a is lower alkoxy or lower hydroxyalkyl.
12 more elements
A compound of Formula XI
- wherein:
- each of Rl, R2, R3, R4, and R5 is independently H, halogen, lower alkyl, lower alkenyl, hydroxy, amino, lower hydroxyalkyl, lower alkoxy, lower thioalkyl, amido, sulfonamido, lower alkyl sulfonyl, lower haloalkyl, lower haloalkoxy, cyano, or —C(═O)R′;
- R′ is heterocycloalkyl, lower alkyl, lower alkoxy, hydroxy;
- and
- each of R6, R7, R8, R9, and R10 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl.
2 more elements
A compound of Formula XII
- wherein:
- R1 is H, halogen, hydroxy, or R′;
- R′ is lower alkyl, phenyl, lower alkoxy, lower haloalkyl, lower hydroxyalkyl, lower alkenyl, lower alkynyl, phenyl lower alkynyl, lower alkoxy, cycloalkenyl, lower alkyl phenylalkyl, aryl, heteroaryl, or alkylheteroaryl, optionally substituted with one or more R″;
- R″ is lower alkyl, halogen, hydroxy, lower alkoxy, amino, lower haloalkyl, or lower hydroxyalkyl;
- and
- each of R2, R3, R4 R5, R6, and R7 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl.
3 more elements
A compound of Formula XIII
- wherein:
- R1 is H, halogen, hydroxy, or R′;
- R′ is lower alkyl, phenyl, lower alkoxy, lower haloalkyl, lower hydroxyalkyl, lower alkenyl, lower alkynyl, phenyl lower alkynyl, lower alkoxy, cycloalkenyl, lower alkyl phenylalkyl, aryl, heteroaryl, or alkylheteroaryl, optionally substituted with one or more R″;
- R″ is lower alkyl, halogen, hydroxy, lower alkoxy, amino, lower haloalkyl, or lower hydroxyalkyl;
- and
- each of R2, R3, R4 R5, R6, and R7 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl.
3 more elements
A compound of Formula XIV
- wherein:
- X is CH or N;
- R1 is H, halogen, hydroxy, or R′;
- R′ is lower alkyl, phenyl, lower alkoxy, lower haloalkyl, lower hydroxyalkyl, lower alkenyl, lower alkynyl, phenyl lower alkynyl, lower alkoxy, cycloalkenyl, lower alkyl phenylalkyl, aryl, heteroaryl, or alkylheteroaryl, optionally substituted with one or more R″;
- R″ is lower alkyl, halogen, hydroxy, lower alkoxy, amino, lower haloalkyl, or lower hydroxyalkyl;
- and
- each of R2, R3, R4 R5, R6, and R7 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl.
4 more elements
A compound of Formula XV
- wherein:
- X and Y are independently selected from H, halogen, hydroxy, and X′;
- X′ is lower alkyl, phenyl, lower alkoxy, lower haloalkyl, lower hydroxyalkyl, lower alkenyl, lower alkynyl, phenyl lower alkynyl, lower alkoxy, cycloalkenyl, lower alkyl phenylalkyl, aryl, heteroaryl, or alkylheteroaryl, optionally substituted with one or more X″;
- X″ is lower alkyl, halogen, hydroxy, lower alkoxy, amino, lower haloalkyl, or lower hydroxyalkyl;
- R3 is halogen;
- each of R1, R2, R4, and R5 is independently H, halogen, lower alkyl, lower alkenyl, hydroxy, amino, lower hydroxyalkyl, lower alkoxy, lower thioalkyl, amido, sulfonamido, lower alkyl sulfonyl, lower haloalkyl, lower haloalkoxy, cyano, or —C(═O)R′;
- R′ is heterocycloalkyl, lower alkyl, lower alkoxy, hydroxy;
- R7 is F, Br, I, hydroxy, or R7;
- R7′ is lower alkyl, lower alkoxy, lower haloalkyl, hydroxy, lower hydroxyalkyl, lower alkenyl, lower alkynyl, phenyl lower alkynyl, lower alkoxy, cycloalkenyl, lower alkyl phenylalkyl, aryl, heteroaryl, or alkylheteroaryl, optionally substituted with one or more R7″;
- R7″ is lower alkyl, halogen, hydroxy, lower alkoxy, amino, lower haloalkyl, or lower hydroxyalkyl;
- and
- each of R6, R8, R9, and R10 is independently H, halogen, lower alkyl, lower alkoxy, heterocycloalkyl, or lower haloalkyl.
9 more elements
A compound selected from the group consisting of:
- (5,7-Diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(2-morpholin-4-yl-ethyl)-amine;
- (2-Morpholin-4-yl-ethyl)-(5-phenyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine;
- 5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine;
- 5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine;
- 5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidine;
- Cyclopentyl-[5-(4-fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- tert-Butyl-[5-(4-fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- 2-[5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-2-methyl-propan-1-ol;
- 5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol;
- 5-(4-Fluoro-phenyl)-4-(2-methoxy-ethoxy)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidine;
- [5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (R)-2-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-propan-1-ol;
- 2-[5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-2-methyl-propane-1,3-diol;
- 2-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-propane-1,3-diol;
- (2-Methoxy-ethyl)-(7-m-tolyl-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine;
- N-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methoxy-acetamide;
- [5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- [7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-1-methoxymethyl- ethyl)-amine;
- 2-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-3-methyl-butan-1-ol;
- N-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-propionamide;
- (S)-2-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-3-methyl-butan-1-ol;
- 2-[5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-2-methyl-propan-1-ol;
- (5-Pent-1-ynyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- (5-Ethynyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- (5-Pentyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- [5-(4-Fluoro-3-methyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (R)-2-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-3-methyl-butan-1-ol;
- [5-(4-Isopropoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (5,7-Di-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(2-methoxy-ethyl)-amine;
- (2-Methoxy-ethyl)-[5-(4-methoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- (S)-2-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-propan-1-ol;
- 4-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenol;
- [5-(2-Chloro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Methoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [7-(3-Ethoxy-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- 2-[5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-2-hydroxymethyl-propane-1,3-diol;
- 4-[7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-cyclo hexanol;
- 2-[5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-2-methyl-propan-1-ol;
- 2-[5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-2-methyl-propane-1,3-diol;
- compound with trifluoro-acetic acid;
- [5-(3,5-Difluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (2-Methoxy-ethyl)-(7-m-tolyl-5-o-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine;
- (2-Methoxy-ethyl)-[7-(3-methoxy-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- (Tetrahydro-pyran-4-yl)-(7-m-tolyl-5-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine;
- [5-(3-Isopropoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(4-Chloro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- [5-(3,4-Dimethyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Fluoro -5-methyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(1H-Pyrrol-2-yl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4yl)-amine;
- [7-(3-tert-Butyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- (5-Methyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- [7-(3-Fluoro-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- [5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(1-methyl-piperidin-4-yl)-amine;
- [5-(4-Chloro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- [5-(2,4-Difluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- N-{4-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenyl}-acetamide;
- [5-(3-Methoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (5-Pyridin-3-yl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- [7-(3,5-Dichloro-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- [7-(4-Chloro-3-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- [5-(3-Chloro-5-fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl-amine;
- [5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperidin-4-yl-amine;
- N-{4-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenyl}-methanesulfonamide;
- (2-Methoxy-ethyl)-[5-phenyl-7-(4-trifluoromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- [5-(4-Chloro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (Tetrahydro-pyran-4-yl)-[7-m-tolyl-5-(4-trifluoromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- (2-Methoxy-ethyl)-[7-(4-methoxy-3-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- [5-(4-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- (Tetrahydro-pyran-4-yl)-(7-m-tolyl-5-o-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine;
- 4-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzamide;
- [7-(4-Fluoro-3-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- 2-Chloro-N,N-dimethyl-4-[4-(tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzamide;
- 7-(3-Chloro-phenyl)-4-(4-methyl-piperazin-1-yl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine;
- [5-(3,4-Dimethyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- 2-[4-(5-Phenyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-ethanol;
- N-{3-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenyl}-acetamide;
- [5-(2-Methylsulfanyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(4-Methoxy-3-trifluoromethyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (Tetrahydro-pyran-4-yl)-[7-m-tolyl-5-(4-trifluoromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- [7-(3,4-Dimethoxy-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- (2-Methoxy-ethyl)-[7-(4-morpholin-4-yl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- [5-(2-Chloro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- 2-{4-[7-(3-Chloro-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-piperazin-1-yl}-ethanol;
- [7-(2-Fluoro-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- [7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-1-methoxymethyl-ethyl)-amine;
- [7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-1-methoxymethyl-ethyl)-amine;
- [7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-pyridin-3-yl-ethyl)-amine;
- [7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-pyridin-2-yl-ethyl)-amine;
- 2-Chloro-4-[4-(tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzamide
- [7-(3-Chloro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-imidazol-1-yl-ethyl)-amine;
- [7-(3-Fluoro-4-methyl-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(2-methoxy-ethyl)-amine;
- 4-(4-Methyl-piperazin-1-yl)-5-phenyl-7-p-tolyl-7H-pyrrolo[2,3-d]pyrimidine;
- {2-Chloro-4-[4-(tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenyl}-pyrrolidin-1-yl-methanone;
- {2-Chloro-4-[4-(tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenyl}-morpholin-4-yl-methanone;
- 2-Fluoro-4-[4-(tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzoic acid methyl ester;
- [5-(5-Chloro-2-methyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(2,3-Difluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Ethoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(4-Methylsulfanyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(2-Ethoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3,5-Dimethyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(4-Fluoro-3-trifluoromethyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Fluoro-4-methoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Fluoro-5-isopropoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Ethoxy-5-fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Methylsulfanyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (Tetrahydro-pyran-4-yl)-[7-m-tolyl-5-(3-trifluoromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- (Tetrahydro-pyran-4-yl)-[7-m-tolyl-5-(3-trifluoromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- [5-(4-tert-Butyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(2-Ethyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(2-Ethyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4yl)-amine;
- [5-(2-Fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(2-Methoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(4-Ethyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- 3-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzonitrile;
- [5-(4-Ethoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Chloro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3,4-Dimethoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Isopropyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(4-Isopropyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (5,7-Di-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine
- [5-(4-Methoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(2-Isopropoxy-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (5-Ethyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- (Tetrahydro-pyran-4-yl)-[7-m-tolyl-5-(2-p-tolyl- ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- (5-Butyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- (Tetrahydro-pyran-4-yl)-[7-m-tolyl-5-(3,4,5-trimethoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine
- [5-(4-Methanesulfonyl-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- 1-{4-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenyl}-ethanone;
- 1-{2-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenyl}-ethanone;
- 4-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzoic acid ethyl ester;
- (Tetrahydro-pyran-4-yl)-(5-thiophen-2-yl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine;
- N-{3-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenyl}-methanesulfonamide;
- (5-Quinolin-8-yl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- N-Methyl-4-[4-(tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzenesulfonamide;
- [5-(3-Amino-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- N,N-Diethyl-2-[4-(tetrahydro-pyran-4-ylamino)-7-m-tolyl-7 H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzamide;
- [5-((E)-Pent-1-enyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(1H-Pyrrol-3-yl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(1-Methyl-1H-pyrrol-2-yl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (Tetrahydro-pyran-4-yl)-[7-m-tolyl-5-(2-vinyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine;
- N-tert-Butyl-3-[4-(tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzenesulfonamide;
- (5-Cyclopent-1-enyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- (5-Cyclohex-1-enyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- 3-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-benzenesulfonamide;
- [5-(4-Dimethylamino-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3-Chloro-4-fluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (Tetrahydro-pyran-4-yl)-(5-thiophen-3-yl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine;
- 1-{5-[4-(Tetrahydro-pyran-4-ylamino)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-thiophen-2-yl}-ethanone;
- [5-(4-Methyl-thiophen-2-yl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(3,4-Difluoro-phenyl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (5-Phenyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- (5-Phenyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-[2-(tetrahydro-pyran-4-yl)-ethyl]-amine;
- (5-Phenyl-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-ylmethyl)-amine;
- (5,7-Diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine;
- (5,7-Diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(tetrahydro-pyran-4-ylmethyl)-amine;
- [5-(1-Methyl-1H-pyrazol-4-yl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(1H-Pyrazol-3-yl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- [5-(1H-Pyrazol-4-yl)-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(tetrahydro-pyran-4-yl)-amine;
- (S)-2-[5-(2-Methyl-propenyl)-7-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-propan-1-ol;
- and
- (S)-2-(5-Isobutyl-7-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-propan-1-ol.
161 more elements
Dependencies are inferred from the claim text.