RU2331644C2 - Пирролопиримидины, обладающие свойствами ингибитора катепсина к, и способ их получения (варианты) - Google Patents
Пирролопиримидины, обладающие свойствами ингибитора катепсина к, и способ их получения (варианты) Download PDFInfo
- Publication number
- RU2331644C2 RU2331644C2 RU2004109815/04A RU2004109815A RU2331644C2 RU 2331644 C2 RU2331644 C2 RU 2331644C2 RU 2004109815/04 A RU2004109815/04 A RU 2004109815/04A RU 2004109815 A RU2004109815 A RU 2004109815A RU 2331644 C2 RU2331644 C2 RU 2331644C2
- Authority
- RU
- Russia
- Prior art keywords
- carbonitrile
- pyrrolo
- ylmethyl
- dimethylpropyl
- pyrimidine
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 4
- 230000002401 inhibitory effect Effects 0.000 title abstract 3
- DLWYPIJIRAXSIR-UHFFFAOYSA-N pyrano[3,2-b]pyrrole-2-carboximidamide Chemical class N1=C(C=C2C1=CC=CO2)C(=N)N DLWYPIJIRAXSIR-UHFFFAOYSA-N 0.000 title 1
- -1 phenyl-W- Chemical group 0.000 claims abstract 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract 17
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 12
- 125000005843 halogen group Chemical group 0.000 claims abstract 8
- 150000002148 esters Chemical class 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 125000003277 amino group Chemical group 0.000 claims abstract 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 18
- IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical compound N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 2
- 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 2
- KPMKBEDNNBTQPE-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(2,4-dioxo-1-oxa-3,8-diazaspiro[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)OC21CCNCC2 KPMKBEDNNBTQPE-UHFFFAOYSA-N 0.000 claims 2
- SUKUDPDURLRHPV-UHFFFAOYSA-N 7-(2,2-dimethylpropyl)-6-[(3-methyl-2,4-dioxo-1-propyl-1,3,8-triazaspiro[4.5]decan-8-yl)methyl]pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CCCN1C(=O)N(C)C(=O)C11CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 SUKUDPDURLRHPV-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 2
- 229940091173 hydantoin Drugs 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 2
- CYJAWBVQRMVFEO-UHFFFAOYSA-N piperazine-2,6-dione Chemical compound O=C1CNCC(=O)N1 CYJAWBVQRMVFEO-UHFFFAOYSA-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
- QODVUAHOCJHECL-UHFFFAOYSA-N 1-oxa-3,8-diazaspiro[4.5]decane-8-carboxylic acid Chemical compound C1CN(CCC12CNCO2)C(=O)O QODVUAHOCJHECL-UHFFFAOYSA-N 0.000 claims 1
- UJHSNWSGTOEURH-UHFFFAOYSA-N 4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]piperazine-1-carboximidamide Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1CCN(C(N)=N)CC1 UJHSNWSGTOEURH-UHFFFAOYSA-N 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
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 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
- HBKGPEOCDSSCFL-UHFFFAOYSA-N 6-(piperidin-1-ylmethyl)-7h-pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical class N1C2=NC(C#N)=NC=C2C=C1CN1CCCCC1 HBKGPEOCDSSCFL-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
- SFVZSWHVHVJATN-UHFFFAOYSA-N 6-[(3-methyl-2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-yl)methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)C)C=1CN(CC1)CCC21NC(=O)N(C)C2=O SFVZSWHVHVJATN-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
- 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
- SBUODCQTURHSIL-UHFFFAOYSA-N 6-[(4-cyclopentylpiperazin-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=1CN(CC1)CCN1C1CCCC1 SBUODCQTURHSIL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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
- AICUKZMRFRXNGM-UHFFFAOYSA-N 6-[[3-[(4-chlorophenyl)methyl]-2,5-dioxoimidazolidin-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=1CN(C1=O)C(=O)CN1CC1=CC=C(Cl)C=C1 AICUKZMRFRXNGM-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
- NPYGIHOGINWDBX-UHFFFAOYSA-N 6-[[4-(2,4-dimethoxyphenyl)piperazin-1-yl]methyl]-7-(2-methylpropyl)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)CC1 NPYGIHOGINWDBX-UHFFFAOYSA-N 0.000 claims 1
- GWVFEBQWHXBYCG-UHFFFAOYSA-N 6-[[4-(2,4-dimethoxyphenyl)piperazin-1-yl]methyl]-7-(3-methylbutyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound COC1=CC(OC)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CCC(C)C)CC1 GWVFEBQWHXBYCG-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
- RGGGAHLNFURXSX-UHFFFAOYSA-N 6-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound COC1=CC=CC(N2CCN(CC=3N(C4=NC(=NC=C4C=3)C#N)CC(C)C)CC2)=C1 RGGGAHLNFURXSX-UHFFFAOYSA-N 0.000 claims 1
- XITVNKOTMJNWEZ-UHFFFAOYSA-N 6-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-7-(3-methylbutyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound COC1=CC=CC(N2CCN(CC=3N(C4=NC(=NC=C4C=3)C#N)CCC(C)C)CC2)=C1 XITVNKOTMJNWEZ-UHFFFAOYSA-N 0.000 claims 1
- MCZPURMRESTIHS-UHFFFAOYSA-N 6-[[4-(4-ethoxyphenyl)piperazin-1-yl]methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(OCC)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)C)CC1 MCZPURMRESTIHS-UHFFFAOYSA-N 0.000 claims 1
- RKTONEIGIQFSLI-UHFFFAOYSA-N 6-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)C)CC1 RKTONEIGIQFSLI-UHFFFAOYSA-N 0.000 claims 1
- OTQQWRVDCCEGIJ-UHFFFAOYSA-N 6-[[4-(4-methoxyphenyl)piperazin-1-yl]methyl]-7-(3-methylbutyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CCC(C)C)CC1 OTQQWRVDCCEGIJ-UHFFFAOYSA-N 0.000 claims 1
- TUTGNZZGSMQOJJ-UHFFFAOYSA-N 6-[[4-(4-methoxyphenyl)piperidin-1-yl]methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)C)CC1 TUTGNZZGSMQOJJ-UHFFFAOYSA-N 0.000 claims 1
- VDPOMTIXABPMGQ-UHFFFAOYSA-N 6-[[4-(4-methoxyphenyl)piperidin-1-yl]methyl]-7-(3-methylbutyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CCC(C)C)CC1 VDPOMTIXABPMGQ-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
- YGNZAVIUOIGCJK-UHFFFAOYSA-N 6-[[4-[2-(diethylamino)ethyl]piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C1CN(CCN(CC)CC)CCN1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C YGNZAVIUOIGCJK-UHFFFAOYSA-N 0.000 claims 1
- AUNXAUMTLBKWDN-UHFFFAOYSA-N 6-[[4-[2-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperazin-1-yl]methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)C)C=1CN(CC1)CCN1C1=CC=CC=C1OCCN1CCN(C)CC1 AUNXAUMTLBKWDN-UHFFFAOYSA-N 0.000 claims 1
- PJLJEGDIMLLAAV-UHFFFAOYSA-N 6-[[4-[2-[2-(diethylamino)ethoxy]phenyl]piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CCN(CC)CCOC1=CC=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 PJLJEGDIMLLAAV-UHFFFAOYSA-N 0.000 claims 1
- KKDDDZBYEIUMHT-UHFFFAOYSA-N 6-[[4-[2-[2-(diethylamino)ethoxy]phenyl]piperidin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CCN(CC)CCOC1=CC=CC=C1C1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 KKDDDZBYEIUMHT-UHFFFAOYSA-N 0.000 claims 1
- CUWLXPUFUKFPNO-UHFFFAOYSA-N 6-[[4-[2-[2-(dimethylamino)ethoxy]phenyl]piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CN(C)CCOC1=CC=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 CUWLXPUFUKFPNO-UHFFFAOYSA-N 0.000 claims 1
- MDBLWYRQEOBOFR-UHFFFAOYSA-N 6-[[4-[2-[2-(dimethylamino)ethoxy]phenyl]piperidin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CN(C)CCOC1=CC=CC=C1C1CCN(CC=2N(C3=NC(=NC=C3C=2)C#N)CC(C)(C)C)CC1 MDBLWYRQEOBOFR-UHFFFAOYSA-N 0.000 claims 1
- HOLAMNFRWUTIPH-UHFFFAOYSA-N 6-[[4-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperazin-1-yl]methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)C)C=1CN(CC1)CCN1C(C=1)=CC=CC=1OCCN1CCN(C)CC1 HOLAMNFRWUTIPH-UHFFFAOYSA-N 0.000 claims 1
- GIGXDLIAJGQRAQ-UHFFFAOYSA-N 6-[[4-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]piperidin-1-yl]methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)C)C=1CN(CC1)CCC1C(C=1)=CC=CC=1OCCN1CCN(C)CC1 GIGXDLIAJGQRAQ-UHFFFAOYSA-N 0.000 claims 1
- MGWKIPBTTZJWJI-UHFFFAOYSA-N 6-[[4-[3-[2-(diethylamino)ethoxy]phenyl]piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CCN(CC)CCOC1=CC=CC(N2CCN(CC=3N(C4=NC(=NC=C4C=3)C#N)CC(C)(C)C)CC2)=C1 MGWKIPBTTZJWJI-UHFFFAOYSA-N 0.000 claims 1
- KRLPSXPOXOZOMU-UHFFFAOYSA-N 6-[[4-[3-[2-(diethylamino)ethoxy]phenyl]piperazin-1-yl]methyl]-7-(2-methylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CCN(CC)CCOC1=CC=CC(N2CCN(CC=3N(C4=NC(=NC=C4C=3)C#N)CC(C)C)CC2)=C1 KRLPSXPOXOZOMU-UHFFFAOYSA-N 0.000 claims 1
- BDZIJGQWILVAPD-UHFFFAOYSA-N 6-[[4-[3-[2-(diethylamino)ethoxy]phenyl]piperidin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CCN(CC)CCOC1=CC=CC(C2CCN(CC=3N(C4=NC(=NC=C4C=3)C#N)CC(C)(C)C)CC2)=C1 BDZIJGQWILVAPD-UHFFFAOYSA-N 0.000 claims 1
- QGLNKPHHNOYCMH-UHFFFAOYSA-N 6-[[4-[3-[2-(dimethylamino)ethoxy]phenyl]piperazin-1-yl]methyl]-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidine-2-carbonitrile Chemical compound CN(C)CCOC1=CC=CC(N2CCN(CC=3N(C4=NC(=NC=C4C=3)C#N)CC(C)(C)C)CC2)=C1 QGLNKPHHNOYCMH-UHFFFAOYSA-N 0.000 claims 1
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- SCRJVXYRZHOVEV-UHFFFAOYSA-N 9-(2,2-dimethylpropyl)-8-[[4-(4-ethoxyphenyl)piperazin-1-yl]methyl]purine-2-carbonitrile Chemical compound C1=CC(OCC)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3N=2)C#N)CC(C)(C)C)CC1 SCRJVXYRZHOVEV-UHFFFAOYSA-N 0.000 claims 1
- FENVMIMLNJLCLD-UHFFFAOYSA-N 9-(2,2-dimethylpropyl)-8-[[4-(4-methoxyphenyl)piperidin-1-yl]methyl]purine-2-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1CCN(CC=2N(C3=NC(=NC=C3N=2)C#N)CC(C)(C)C)CC1 FENVMIMLNJLCLD-UHFFFAOYSA-N 0.000 claims 1
- AKFTYCRADKOBGI-UHFFFAOYSA-N 9-(2,2-dimethylpropyl)-8-[[4-[4-(2-hydroxyethoxy)phenyl]piperazin-1-yl]methyl]purine-2-carbonitrile Chemical compound N=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN(CC1)CCN1C1=CC=C(OCCO)C=C1 AKFTYCRADKOBGI-UHFFFAOYSA-N 0.000 claims 1
- KPZUIZAZQYTZID-UHFFFAOYSA-N 9-(2,2-dimethylpropyl)-8-methylpurine-2-carbonitrile Chemical compound N1=C(C#N)N=C2N(CC(C)(C)C)C(C)=NC2=C1 KPZUIZAZQYTZID-UHFFFAOYSA-N 0.000 claims 1
- RSOFPRSWMWSROG-UHFFFAOYSA-N 9-(cyclohexylmethyl)-8-[[4-(2,4-dimethoxyphenyl)piperazin-1-yl]methyl]purine-2-carbonitrile Chemical compound COC1=CC(OC)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3N=2)C#N)CC2CCCCC2)CC1 RSOFPRSWMWSROG-UHFFFAOYSA-N 0.000 claims 1
- OKQTTZHXMRKPBQ-UHFFFAOYSA-N 9-(cyclohexylmethyl)-8-[[4-[4-(2-hydroxyethoxy)phenyl]piperazin-1-yl]methyl]purine-2-carbonitrile Chemical compound C1=CC(OCCO)=CC=C1N1CCN(CC=2N(C3=NC(=NC=C3N=2)C#N)CC2CCCCC2)CC1 OKQTTZHXMRKPBQ-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- CBUNWEQRCRGRNA-UHFFFAOYSA-N n-[4-[4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN(CC1)CCN1C1=CC=C(NS(C)(=O)=O)C=C1 CBUNWEQRCRGRNA-UHFFFAOYSA-N 0.000 claims 1
- JNZXOXWZMCNYJB-UHFFFAOYSA-N n-[4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]phenyl]-n-methylmethanesulfonamide Chemical compound C1=CC(N(C)S(C)(=O)=O)=CC=C1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C JNZXOXWZMCNYJB-UHFFFAOYSA-N 0.000 claims 1
- YYHLNGKLSXDOSN-UHFFFAOYSA-N n-[4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C YYHLNGKLSXDOSN-UHFFFAOYSA-N 0.000 claims 1
- SZSUNQBSXSFPDF-UHFFFAOYSA-N n-[4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1CC1=CC2=CN=C(C#N)N=C2N1CC(C)(C)C SZSUNQBSXSFPDF-UHFFFAOYSA-N 0.000 claims 1
- WFNRSIKLRUTKMJ-UHFFFAOYSA-N n-[4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]phenyl]methanesulfonamide Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CC1=CC=C(NS(C)(=O)=O)C=C1 WFNRSIKLRUTKMJ-UHFFFAOYSA-N 0.000 claims 1
- WAKCWSQTCYLGMT-UHFFFAOYSA-N n-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]-4-fluorobenzamide Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CNC(=O)C1=CC=C(F)C=C1 WAKCWSQTCYLGMT-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- NWSNCNVCDPBGAR-UHFFFAOYSA-N tert-butyl 4-[[2-cyano-7-(2,2-dimethylpropyl)pyrrolo[2,3-d]pyrimidin-6-yl]methyl]-3,5-dioxopiperazine-1-carboxylate Chemical compound C=1C2=CN=C(C#N)N=C2N(CC(C)(C)C)C=1CN1C(=O)CN(C(=O)OC(C)(C)C)CC1=O NWSNCNVCDPBGAR-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 2
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 208000001132 Osteoporosis Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 201000008482 osteoarthritis Diseases 0.000 abstract 1
- 150000004944 pyrrolopyrimidines Chemical class 0.000 abstract 1
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 0 CCc([n]1C)cc2c1nc(C)nc2* Chemical compound CCc([n]1C)cc2c1nc(C)nc2* 0.000 description 1
- DPGGUVHTOSWCAM-UHFFFAOYSA-N Cc1nc([n](C)c(CO)c2)c2cn1 Chemical compound Cc1nc([n](C)c(CO)c2)c2cn1 DPGGUVHTOSWCAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
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- Health & Medical Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| RU2004109815A RU2004109815A (ru) | 2005-10-20 |
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| EP1619193A4 (en) * | 2003-04-18 | 2010-08-11 | Ono Pharmaceutical Co | SPIROPIPERIDINE COMPOUND AND MEDICINAL USE THEREOF |
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| EP1797883A3 (en) * | 2003-04-28 | 2007-08-01 | Novartis AG | Pharmaceutical composition comprising a cathepsin S inhibitor and an opioid |
| ATE434612T1 (de) * | 2003-04-30 | 2009-07-15 | Bayer Cropscience Ag | Insektizide (dihalopropenyl)phenylalkyl substituierte dihydrobenzofuran- und dihydrobenzopyran-derivate |
| WO2005011703A1 (en) * | 2003-08-04 | 2005-02-10 | Akzo Nobel N.V. | 2-cyano-1,3,5-triazine-4,6-diamine derivatives |
| CA2579609A1 (en) | 2003-09-10 | 2005-03-17 | Virochem Pharma Inc. | Spirohydantoin compounds and methods for the modulation of chemokine receptor activity |
| WO2005080356A1 (en) | 2004-02-18 | 2005-09-01 | Astrazeneca Ab | Tetrazole compounds and their use as metabotropic glutamate receptor antagonits |
| EP1724264A1 (en) * | 2004-03-10 | 2006-11-22 | Ono Pharmaceutical Co., Ltd. | Nitriles and medicinal compositions containing the same as the active ingredient |
| ES2251292B1 (es) * | 2004-04-20 | 2007-07-01 | Inke, S.A. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo y de sus intermedios de sintesis. |
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| TW200614993A (en) | 2004-06-11 | 2006-05-16 | Akzo Nobel Nv | 4-phenyl-pyrimidine-2-carbonitrile derivatives |
| US7951816B2 (en) | 2004-08-27 | 2011-05-31 | Ono Pharmaceutical Co., Ltd. | Compound containing basic group and use thereof |
| KR100651849B1 (ko) * | 2005-02-01 | 2006-12-01 | 엘지전자 주식회사 | 세탁기 |
| RU2424234C2 (ru) * | 2005-08-05 | 2011-07-20 | Ибриженикс Са | Новые ингибиторы цистеиновых протеаз и их терапевтическое применение |
| EP1933860A2 (en) | 2005-09-01 | 2008-06-25 | Ares Trading S.A. | Treatment of optic neuritis |
| TW200745055A (en) * | 2005-09-23 | 2007-12-16 | Organon Nv | 4-Phenyl-6-substituted-pyrimidine-2-carbonitrile derivatives |
| US7326715B2 (en) | 2005-09-23 | 2008-02-05 | N.V. Organon | 4-Phenyl-6-substituted-pyrimidine-2-carbonitrile derivatives |
| TW200732314A (en) * | 2005-10-26 | 2007-09-01 | Smithkline Beecham Corp | Substituted thiazoles and their use |
| PT1961744E (pt) | 2005-11-18 | 2013-05-15 | Ono Pharmaceutical Co | Composto que contém um grupo básico e sua utilização |
| EA200870019A1 (ru) * | 2005-12-05 | 2008-12-30 | Инсайт Корпорейшн | Лактамовые соединения и способы их применения |
| US7687515B2 (en) | 2006-01-17 | 2010-03-30 | N.V. Organon | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| US8618122B2 (en) | 2006-05-16 | 2013-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having acidic group which may be protected, and use thereof |
| 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 |
| TW200911803A (en) * | 2007-07-16 | 2009-03-16 | Organon Nv | 6-phenyl-1H-imidazo [4,5-c] pyridine-4-carbonitrile derivatives |
| 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. |
| WO2009155475A1 (en) | 2008-06-20 | 2009-12-23 | Novartis Ag | Paediatric compositions for treating1 multiple sclerosis |
| TW201035094A (en) | 2009-01-16 | 2010-10-01 | Organon Nv | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| US8026236B2 (en) | 2009-01-16 | 2011-09-27 | N.V. Organon | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| EP2448938B9 (en) | 2009-06-29 | 2015-06-10 | Incyte Corporation | Pyrimidinones as pi3k inhibitors |
| WO2011075643A1 (en) | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted heteroaryl fused derivatives as pi3k inhibitors |
| KR20120124428A (ko) | 2009-12-30 | 2012-11-13 | 아르퀼 인코포레이티드 | 치환된 피롤로-아미노피리미딘 화합물 |
| EP2523954B1 (en) | 2010-01-15 | 2014-04-16 | Merck Sharp & Dohme B.V. | 1h-[1,2,3]triazolo[4,5-c]pyridine-4- carbonitrile derivatives as cathepsin s inhibitors |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| US9062055B2 (en) | 2010-06-21 | 2015-06-23 | Incyte Corporation | Fused pyrrole derivatives as PI3K inhibitors |
| WO2012027495A1 (en) | 2010-08-27 | 2012-03-01 | University Of The Pacific | Piperazinylpyrimidine analogues as protein kinase inhibitors |
| ES2562274T3 (es) | 2010-10-06 | 2016-03-03 | Fundació Institut De Recerca Biomèdica (Irb Barcelona) | Procedimiento para el diagnóstico, pronóstico y tratamiento de metástasis de cáncer de mama |
| JP5961187B2 (ja) | 2010-12-20 | 2016-08-02 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉ３ｋ阻害剤としてのｎ−（１−（置換フェニル）エチル）−９ｈ−プリン−６−アミン |
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