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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- A61P11/00—Drugs for disorders of the respiratory system
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- 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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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Rheumatology (AREA)
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- Transplantation (AREA)
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- Hematology (AREA)
- Pulmonology (AREA)
- 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)
Applications Claiming Priority (2)
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|---|---|---|---|
| GBGB0121033.5A GB0121033D0 (en) | 2001-08-30 | 2001-08-30 | Organic compounds |
| GB0121033.5 | 2001-08-30 |
Publications (2)
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|---|---|
| RU2004109815A RU2004109815A (ru) | 2005-10-20 |
| RU2331644C2 true RU2331644C2 (ru) | 2008-08-20 |
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| RU2004109815/04A RU2331644C2 (ru) | 2001-08-30 | 2002-08-29 | Пирролопиримидины, обладающие свойствами ингибитора катепсина к, и способ их получения (варианты) |
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| IL (3) | IL160367A0 (https=) |
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| PE20050068A1 (es) * | 2003-02-06 | 2005-03-11 | Novartis Ag | 2-cianopirrolopirimidinas como inhibidores de la catepsina s |
| GB0304640D0 (en) * | 2003-02-28 | 2003-04-02 | Novartis Ag | Organic compounds |
| WO2004092169A1 (ja) * | 2003-04-18 | 2004-10-28 | Ono Pharmaceutical Co., Ltd. | スピロピペリジン化合物およびその医薬用途 |
| US20070037835A1 (en) * | 2003-04-28 | 2007-02-15 | Pamposh Ganju | Pharmaceutical composition comprising a cathepsin s inhibitor and an opioid |
| EP1797883A3 (en) * | 2003-04-28 | 2007-08-01 | Novartis AG | Pharmaceutical composition comprising a cathepsin S inhibitor and an opioid |
| CA2523085A1 (en) * | 2003-04-30 | 2004-11-18 | Fmc Corporation | Insecticidal (dihalopropenyl) phenylalkyl substituted dihydrobenzofuran and dihydrobenzopyran derivatives |
| WO2005011703A1 (en) * | 2003-08-04 | 2005-02-10 | Akzo Nobel N.V. | 2-cyano-1,3,5-triazine-4,6-diamine derivatives |
| WO2005023810A1 (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 |
| JPWO2005085210A1 (ja) * | 2004-03-10 | 2008-01-17 | 小野薬品工業株式会社 | ニトリル化合物およびその化合物を有効成分として含有する医薬組成物 |
| 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 |
| EP1790639B1 (en) | 2004-08-27 | 2014-03-26 | Ono Pharmaceutical Co., Ltd. | Spirocyclic compounds and their use as cxcr4-antagonists |
| 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 |
| EA013816B1 (ru) | 2005-09-01 | 2010-08-30 | Арес Трейдинг С.А. | Лечение неврита зрительного нерва |
| 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 |
| 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 |
| CA2630492C (en) * | 2005-12-05 | 2015-04-14 | Incyte Corporation | Spiro-lactam compounds |
| US7687515B2 (en) | 2006-01-17 | 2010-03-30 | N.V. Organon | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| WO2007132846A1 (ja) | 2006-05-16 | 2007-11-22 | Ono Pharmaceutical Co., Ltd. | 保護されていてもよい酸性基を含有する化合物およびその用途 |
| 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. |
| 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 |
| US8026236B2 (en) | 2009-01-16 | 2011-09-27 | N.V. Organon | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| KR101763656B1 (ko) | 2009-06-29 | 2017-08-01 | 인사이트 홀딩스 코포레이션 | Ｐｉ3ｋ 저해물질로서의 피리미디논 |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| AU2010339444A1 (en) | 2009-12-30 | 2012-07-19 | Arqule, Inc. | Substituted pyrrolo-aminopyrimidine compounds |
| WO2011086125A1 (en) | 2010-01-15 | 2011-07-21 | N.V. Organon | 1H-[1,2,3]TRIAZOLO[4,5-c]PYRIDINE-4-CARBONITRILE DERIVATIVES |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| US8609672B2 (en) | 2010-08-27 | 2013-12-17 | University Of The Pacific | Piperazinylpyrimidine analogues as protein kinase inhibitors |
| EP3517630B1 (en) | 2010-10-06 | 2022-01-19 | Institució Catalana de Recerca i Estudis Avançats | Method for the diagnosis, prognosis and treatment of breast cancer metastasis |
| EP3660016A1 (en) | 2010-12-20 | 2020-06-03 | Incyte Holdings Corporation | N-(1-(substituted-phenyl)ethyl)-9h-purin-6-amines as pi3k inhibitors |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
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