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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| EA013816B1 (ru) | 2005-09-01 | 2010-08-30 | Арес Трейдинг С.А. | Лечение неврита зрительного нерва |
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| TW200732314A (en) * | 2005-10-26 | 2007-09-01 | Smithkline Beecham Corp | Substituted thiazoles and their use |
| 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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| JP2010503656A (ja) | 2006-09-13 | 2010-02-04 | アストラゼネカ アクチボラグ | スピロ−オキサゾリジノン化合物と代謝共役型グルタミン酸受容体ポテンシエーターとしてのその使用 |
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| US7932251B2 (en) | 2007-07-16 | 2011-04-26 | N.V. Organon | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| BRPI0818448A2 (pt) | 2007-10-19 | 2015-05-12 | Astrazeneca Ab | Composto, composição farmacêutica, uso de um composto, e, métodos para o tratamento ou prevenção de um distúrbio madiano pelo receptor mglur5. |
| JP2011525189A (ja) | 2008-06-20 | 2011-09-15 | ノバルティス アーゲー | 多発性硬化症を治療するための小児科の組成物 |
| TW201035094A (en) | 2009-01-16 | 2010-10-01 | Organon Nv | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
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