JP2005502683A5 - - Google Patents
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- Publication number
- JP2005502683A5 JP2005502683A5 JP2003524991A JP2003524991A JP2005502683A5 JP 2005502683 A5 JP2005502683 A5 JP 2005502683A5 JP 2003524991 A JP2003524991 A JP 2003524991A JP 2003524991 A JP2003524991 A JP 2003524991A JP 2005502683 A5 JP2005502683 A5 JP 2005502683A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- propyl
- dimethyl
- pyrimidine
- carbonitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 64
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 23
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 22
- 125000003282 alkyl amino group Chemical group 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- -1 and R4 is H Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000003435 aroyl group Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- YFLJDICREHFXTF-UHFFFAOYSA-N 4-[4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]anilino]-4-oxobutanoic acid Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CC1=CC=C(NC(=O)CCC(O)=O)C=C1 YFLJDICREHFXTF-UHFFFAOYSA-N 0.000 claims 2
- XCLCHALZLMRKMQ-UHFFFAOYSA-N 6-[(6-chloropyrimidin-4-yl)oxymethyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1COC1=CC(Cl)=NC=N1 XCLCHALZLMRKMQ-UHFFFAOYSA-N 0.000 claims 2
- VDTQYMVZZNQBPA-UHFFFAOYSA-N 6-[[(4-chloropyrimidin-2-yl)amino]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CNC1=NC=CC(Cl)=N1 VDTQYMVZZNQBPA-UHFFFAOYSA-N 0.000 claims 2
- OPSCDEKVNNNUFM-UHFFFAOYSA-N 6-[[4-[4-[2-(dimethylamino)ethoxy]phenyl]piperidin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(OCCN(C)C)=CC=C1C1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 OPSCDEKVNNNUFM-UHFFFAOYSA-N 0.000 claims 2
- NRXQFHRFWPCKKP-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(4-hydroxyiminopiperidin-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1CCC(=NO)CC1 NRXQFHRFWPCKKP-UHFFFAOYSA-N 0.000 claims 2
- PTRYEFUPJUDRSE-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(6-methoxypyridazin-3-yl)oxymethyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound N1=NC(OC)=CC=C1OCC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C PTRYEFUPJUDRSE-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- INSORAMQJUDMGZ-UHFFFAOYSA-N 1-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]-n-phenylpiperidine-4-carboxamide Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN(CC1)CCC1C(=O)NC1=CC=CC=C1 INSORAMQJUDMGZ-UHFFFAOYSA-N 0.000 claims 1
- ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 claims 1
- QOWVDOOBMUSMBK-UHFFFAOYSA-N 4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]-3,5-dioxopiperazine-1-carboxylic acid Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1C(=O)CN(C(O)=O)CC1=O QOWVDOOBMUSMBK-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- DLMFQJCZDMYOLX-UHFFFAOYSA-N 6-(cyclohexylsulfonylmethyl)-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1(CCCCC1)S(=O)(=O)CC1=CC2=C(N=C(N=C2)C#N)N1CC(C)(C)C DLMFQJCZDMYOLX-UHFFFAOYSA-N 0.000 claims 1
- SRRUNBQCDUMELK-UHFFFAOYSA-N 6-(cyclopentylsulfonylmethyl)-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CS(=O)(=O)C1CCCC1 SRRUNBQCDUMELK-UHFFFAOYSA-N 0.000 claims 1
- VGUCQUBMYXWLEJ-UHFFFAOYSA-N 6-[(3-amino-1,2,4-triazol-1-yl)methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1C=NC(N)=N1 VGUCQUBMYXWLEJ-UHFFFAOYSA-N 0.000 claims 1
- ONNNJLDEPAZHLQ-UHFFFAOYSA-N 6-[(4-aminophenyl)methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CC1=CC=C(N)C=C1 ONNNJLDEPAZHLQ-UHFFFAOYSA-N 0.000 claims 1
- ZJUNFFKKIRGUPL-UHFFFAOYSA-N 6-[(4-aminopiperidin-1-yl)methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1CCC(N)CC1 ZJUNFFKKIRGUPL-UHFFFAOYSA-N 0.000 claims 1
- KAZZFKVDMBTPLY-UHFFFAOYSA-N 6-[(4-butanoylpiperazin-1-yl)methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1CN(C(=O)CCC)CCN1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C KAZZFKVDMBTPLY-UHFFFAOYSA-N 0.000 claims 1
- VOABHOCZYOLWHL-UHFFFAOYSA-N 6-[(4-butylsulfonyl-2,6-dioxopiperazin-1-yl)methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound O=C1CN(S(=O)(=O)CCCC)CC(=O)N1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C VOABHOCZYOLWHL-UHFFFAOYSA-N 0.000 claims 1
- ORWXGUZMNRLSLG-UHFFFAOYSA-N 6-[(4-chloro-n-methylanilino)methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN(C)C1=CC=C(Cl)C=C1 ORWXGUZMNRLSLG-UHFFFAOYSA-N 0.000 claims 1
- KRXIONWULNSNIA-UHFFFAOYSA-N 6-[(6-chloropyridin-3-yl)oxymethyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1COC1=CC=C(Cl)N=C1 KRXIONWULNSNIA-UHFFFAOYSA-N 0.000 claims 1
- YTTDBGZSXXZUKX-JOCHJYFZSA-N 6-[[(4r)-3-[(4-chlorophenyl)methyl]-2,5-dioxo-4-propan-2-ylimidazolidin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound N1([C@@H](C(N(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)C1=O)=O)C(C)C)CC1=CC=C(Cl)C=C1 YTTDBGZSXXZUKX-JOCHJYFZSA-N 0.000 claims 1
- BPKVCHZUIJHACN-UHFFFAOYSA-N 6-[[2-(difluoromethyl)pyridin-4-yl]oxymethyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1COC1=CC=NC(C(F)F)=C1 BPKVCHZUIJHACN-UHFFFAOYSA-N 0.000 claims 1
- SPUYFKBFURBLKE-UHFFFAOYSA-N 6-[[4-(2,4-dimethoxyphenyl)piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound COC1=CC(OC)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 SPUYFKBFURBLKE-UHFFFAOYSA-N 0.000 claims 1
- CDZBRYFIHGHOAJ-UHFFFAOYSA-N 6-[[4-(2,4-dimethoxyphenyl)piperidin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound COC1=CC(OC)=CC=C1C1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 CDZBRYFIHGHOAJ-UHFFFAOYSA-N 0.000 claims 1
- OAINXYLTHFSMMN-UHFFFAOYSA-N 6-[[4-(2,6-dimethylphenyl)piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CC1=CC=CC(C)=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 OAINXYLTHFSMMN-UHFFFAOYSA-N 0.000 claims 1
- RIQOIGVIZNQWRT-UHFFFAOYSA-N 6-[[4-(3,4-dimethylphenyl)piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=C(C)C(C)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 RIQOIGVIZNQWRT-UHFFFAOYSA-N 0.000 claims 1
- IQFKMQAIOBWBLW-UHFFFAOYSA-N 6-[[4-(4-acetylphenyl)piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 IQFKMQAIOBWBLW-UHFFFAOYSA-N 0.000 claims 1
- UMAXMYCILWJYLE-UHFFFAOYSA-N 6-[[4-(bromomethyl)phenyl]methyl]-7-cyclohexylpyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(CBr)=CC=C1CC1=CC2=CN=C(C#N)N=C2N1C1CCCCC1 UMAXMYCILWJYLE-UHFFFAOYSA-N 0.000 claims 1
- GGAYIGWLHXTANP-UHFFFAOYSA-N 6-benzyl-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)C)C=1CC1=CC=CC=C1 GGAYIGWLHXTANP-UHFFFAOYSA-N 0.000 claims 1
- TWEMVYLZNFEDGK-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-(imidazol-1-ylmethyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1C=CN=C1 TWEMVYLZNFEDGK-UHFFFAOYSA-N 0.000 claims 1
- PUYWQTHRUDZMLC-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-(naphthalen-2-ylmethyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C2N(CC(C)(C)C)C(CC=3C=C4C=CC=CC4=CC=3)=CC2=C1 PUYWQTHRUDZMLC-UHFFFAOYSA-N 0.000 claims 1
- XQWHIIQIVZJEMR-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-(piperazin-1-ylmethyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1CCNCC1 XQWHIIQIVZJEMR-UHFFFAOYSA-N 0.000 claims 1
- MCTBEZRRBWETKQ-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-(pyridin-4-yloxymethyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1COC1=CC=NC=C1 MCTBEZRRBWETKQ-UHFFFAOYSA-N 0.000 claims 1
- HCQDVZWAHCAVAN-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-(tetrazol-1-ylmethyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1C=NN=N1 HCQDVZWAHCAVAN-UHFFFAOYSA-N 0.000 claims 1
- ZTEFVMVRGUSBOS-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-(tetrazol-2-ylmethyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1N=CN=N1 ZTEFVMVRGUSBOS-UHFFFAOYSA-N 0.000 claims 1
- NXBKLPMOMROGPT-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1CCS(=O)(=O)CC1 NXBKLPMOMROGPT-UHFFFAOYSA-N 0.000 claims 1
- HMHIKIJXNFXOLP-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(1,3-dioxoisoindol-2-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound N1=C(C#N)N=C2N(CC(C)(C)C)C(CN3C(C4=CC=CC=C4C3=O)=O)=CC2=C1 HMHIKIJXNFXOLP-UHFFFAOYSA-N 0.000 claims 1
- HPONNJVVWKWGIG-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(2,4-dioxo-8-pyrimidin-2-yl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN(C1=O)C(=O)NC1(CC1)CCN1C1=NC=CC=N1 HPONNJVVWKWGIG-UHFFFAOYSA-N 0.000 claims 1
- DCRDJUKEEDFMJM-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(2,6-dioxo-4-phenylsulfanylpiperazin-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN(C(C1)=O)C(=O)CN1SC1=CC=CC=C1 DCRDJUKEEDFMJM-UHFFFAOYSA-N 0.000 claims 1
- DRETZBXCDQMKEU-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(2,6-dioxopiperazin-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1C(=O)CNCC1=O DRETZBXCDQMKEU-UHFFFAOYSA-N 0.000 claims 1
- GRDGOWSHAKRGKL-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(3-methyl-1,4-dioxophthalazin-2-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound O=C1C2=CC=CC=C2C(=O)N(C)N1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C GRDGOWSHAKRGKL-UHFFFAOYSA-N 0.000 claims 1
- ZYMLDSPQZKWMIL-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(3-nitro-1,2,4-triazol-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1C=NC([N+]([O-])=O)=N1 ZYMLDSPQZKWMIL-UHFFFAOYSA-N 0.000 claims 1
- OSDDWOIIKLKPAK-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(4-methoxyphenyl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C OSDDWOIIKLKPAK-UHFFFAOYSA-N 0.000 claims 1
- SYHBEDCSCPDPHK-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(4-oxopiperidin-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1CCC(=O)CC1 SYHBEDCSCPDPHK-UHFFFAOYSA-N 0.000 claims 1
- JJEKJRFGVLIFFV-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(4-phenylpiperidin-1-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN(CC1)CCC1C1=CC=CC=C1 JJEKJRFGVLIFFV-UHFFFAOYSA-N 0.000 claims 1
- FRYZBJZFCPOOIO-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(4-pyrrol-1-ylphenyl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CC(C=C1)=CC=C1N1C=CC=C1 FRYZBJZFCPOOIO-UHFFFAOYSA-N 0.000 claims 1
- UWHQBQUZWAPNLT-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(6-morpholin-4-ylpyrimidin-4-yl)oxymethyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1COC(N=CN=1)=CC=1N1CCOCC1 UWHQBQUZWAPNLT-UHFFFAOYSA-N 0.000 claims 1
- BJQDLCMDHPWKCD-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[[4-(2-ethoxyethyl)piperazin-1-yl]methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1CN(CCOCC)CCN1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C BJQDLCMDHPWKCD-UHFFFAOYSA-N 0.000 claims 1
- CWAWHGMQUOVUNP-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[[4-(2-fluoro-4-methylphenyl)piperazin-1-yl]methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound FC1=CC(C)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 CWAWHGMQUOVUNP-UHFFFAOYSA-N 0.000 claims 1
- OADYPSSPKCRBET-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1CN(CCOC)CCN1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C OADYPSSPKCRBET-UHFFFAOYSA-N 0.000 claims 1
- QJPDRXSQBQNRMV-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound COC1=CC=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 QJPDRXSQBQNRMV-UHFFFAOYSA-N 0.000 claims 1
- YAXHAOVRQMQDBH-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[[4-(2-methyl-4-nitrophenyl)piperazin-1-yl]methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 YAXHAOVRQMQDBH-UHFFFAOYSA-N 0.000 claims 1
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| US7326715B2 (en) | 2005-09-23 | 2008-02-05 | N.V. Organon | 4-Phenyl-6-substituted-pyrimidine-2-carbonitrile derivatives |
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| WO2007058322A1 (ja) | 2005-11-18 | 2007-05-24 | Ono Pharmaceutical Co., Ltd. | 塩基性基を含有する化合物およびその用途 |
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| US8618122B2 (en) | 2006-05-16 | 2013-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having acidic group which may be protected, and use thereof |
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| EP2448938B9 (en) | 2009-06-29 | 2015-06-10 | Incyte Corporation | Pyrimidinones as pi3k inhibitors |
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