ES2533873T3 - Derivados de 6-(pirrolopiridinil)-pirimidin-2-il-amina y su utilización para el tratamiento del cáncer y del SIDA - Google Patents
Derivados de 6-(pirrolopiridinil)-pirimidin-2-il-amina y su utilización para el tratamiento del cáncer y del SIDA Download PDFInfo
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- ES2533873T3 ES2533873T3 ES08758743.2T ES08758743T ES2533873T3 ES 2533873 T3 ES2533873 T3 ES 2533873T3 ES 08758743 T ES08758743 T ES 08758743T ES 2533873 T3 ES2533873 T3 ES 2533873T3
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- ES
- Spain
- Prior art keywords
- pyridin
- pyrrolo
- pyrimidin
- ylamine
- ethyl
- 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.)
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- REPODGYKGOPEIK-UHFFFAOYSA-N 4-(1h-pyrrolo[3,2-b]pyridin-2-yl)pyrimidin-2-amine Chemical class NC1=NC=CC(C=2NC3=CC=CN=C3C=2)=N1 REPODGYKGOPEIK-UHFFFAOYSA-N 0.000 title 1
- 208000030507 AIDS Diseases 0.000 title 1
- 206010028980 Neoplasm Diseases 0.000 title 1
- 201000011510 cancer Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000012453 solvate Substances 0.000 claims abstract description 4
- -1 1-methyl-1H-pyrazol-4-yl Chemical group 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- KIAMHLLSQXBNLG-UHFFFAOYSA-N 4-(methoxymethyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(COC)=CC(C=2C3=CC=CN=C3NC=2)=N1 KIAMHLLSQXBNLG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- GDXKHQSVGXORIU-UHFFFAOYSA-N 3-[2-amino-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]propan-1-ol Chemical compound NC1=NC(CCCO)=CC(C=2C3=CC=CN=C3NC=2)=N1 GDXKHQSVGXORIU-UHFFFAOYSA-N 0.000 claims description 3
- BTILBWWSMVZRAH-UHFFFAOYSA-N 4-(1-benzylpyrrolo[2,3-b]pyridin-3-yl)-6-butylpyrimidin-2-amine Chemical compound NC1=NC(CCCC)=CC(C=2C3=CC=CN=C3N(CC=3C=CC=CC=3)C=2)=N1 BTILBWWSMVZRAH-UHFFFAOYSA-N 0.000 claims description 3
- APHLCEJVKPFNDR-UHFFFAOYSA-N 4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)-6-ethylpyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(Br)=CN=C3NC=2)=N1 APHLCEJVKPFNDR-UHFFFAOYSA-N 0.000 claims description 3
- JORQZEAAPPHRPP-UHFFFAOYSA-N 4-[2-amino-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]butan-1-ol Chemical compound NC1=NC(CCCCO)=CC(C=2C3=CC=CN=C3NC=2)=N1 JORQZEAAPPHRPP-UHFFFAOYSA-N 0.000 claims description 3
- NCMSADKBSSLAPO-UHFFFAOYSA-N 4-methyl-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CN=C3NC=2)=N1 NCMSADKBSSLAPO-UHFFFAOYSA-N 0.000 claims description 3
- PZIICVZCJSWGHC-UHFFFAOYSA-N 2-[[2-amino-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]methyl]isoindole-1,3-dione Chemical compound C1=CC=C2C(C=3C=C(CN4C(C5=CC=CC=C5C4=O)=O)N=C(N=3)N)=CNC2=N1 PZIICVZCJSWGHC-UHFFFAOYSA-N 0.000 claims description 2
- QZPHNBQZDLFZBZ-UHFFFAOYSA-N 3-(2-amino-6-ethylpyrimidin-4-yl)-1h-pyrrolo[2,3-b]pyridine-5-carbonitrile Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C#N)=N1 QZPHNBQZDLFZBZ-UHFFFAOYSA-N 0.000 claims description 2
- HMMJUERUXFGFAU-UHFFFAOYSA-N 3-[2-amino-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]propanoic acid Chemical compound NC1=NC(CCC(O)=O)=CC(C=2C3=CC=CN=C3NC=2)=N1 HMMJUERUXFGFAU-UHFFFAOYSA-N 0.000 claims description 2
- QQICAOBAKZSTHL-UHFFFAOYSA-N 3-[3-(2-amino-6-ethylpyrimidin-4-yl)-1h-pyrrolo[2,3-b]pyridin-5-yl]benzonitrile Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=C(C=CC=2)C#N)=N1 QQICAOBAKZSTHL-UHFFFAOYSA-N 0.000 claims description 2
- YTDJUXAAFLWFNL-UHFFFAOYSA-N 3-amino-5-[3-(2-amino-6-ethylpyrimidin-4-yl)-1h-pyrrolo[2,3-b]pyridin-5-yl]benzoic acid Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=C(C=C(N)C=2)C(O)=O)=N1 YTDJUXAAFLWFNL-UHFFFAOYSA-N 0.000 claims description 2
- JVEMVAUGSDQMBQ-UHFFFAOYSA-N 4-(3-aminophenyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=CC=CC(C=2N=C(N)N=C(C=2)C=2C3=CC=CN=C3NC=2)=C1 JVEMVAUGSDQMBQ-UHFFFAOYSA-N 0.000 claims description 2
- QBVINLSVMJNOMO-UHFFFAOYSA-N 4-(3-aminopropyl)-6-[5-(furan-2-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CCCN)=CC(C=2C3=CC(=CN=C3NC=2)C=2OC=CC=2)=N1 QBVINLSVMJNOMO-UHFFFAOYSA-N 0.000 claims description 2
- PVWXGLBWASRHQT-UHFFFAOYSA-N 4-(3-morpholin-4-ylpropyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CN=C3NC=2)=NC(N)=NC=1CCCN1CCOCC1 PVWXGLBWASRHQT-UHFFFAOYSA-N 0.000 claims description 2
- FOWOJHPDXGIDCC-UHFFFAOYSA-N 4-(3-nitrophenyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound N=1C(N)=NC(C=2C3=CC=CN=C3NC=2)=CC=1C1=CC=CC([N+]([O-])=O)=C1 FOWOJHPDXGIDCC-UHFFFAOYSA-N 0.000 claims description 2
- LWOZLUBOHPWOHE-UHFFFAOYSA-N 4-(3-piperazin-1-ylpropyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CN=C3NC=2)=NC(N)=NC=1CCCN1CCNCC1 LWOZLUBOHPWOHE-UHFFFAOYSA-N 0.000 claims description 2
- SFPRWTKWKSLGHV-UHFFFAOYSA-N 4-(4-chloro-1h-pyrrolo[2,3-b]pyridin-3-yl)-6-ethylpyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=C(Cl)C=CN=C3NC=2)=N1 SFPRWTKWKSLGHV-UHFFFAOYSA-N 0.000 claims description 2
- FPFNPQZVYJGJCU-UHFFFAOYSA-N 4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)-6-phenylpyrimidin-2-amine Chemical compound N=1C(N)=NC(C=2C3=CC(Br)=CN=C3NC=2)=CC=1C1=CC=CC=C1 FPFNPQZVYJGJCU-UHFFFAOYSA-N 0.000 claims description 2
- OWZPQUMXIBNPMJ-UHFFFAOYSA-N 4-(methoxymethyl)-6-[1-[(4-methoxyphenyl)methyl]pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(COC)=CC(C=2C3=CC=CN=C3N(CC=3C=CC(OC)=CC=3)C=2)=N1 OWZPQUMXIBNPMJ-UHFFFAOYSA-N 0.000 claims description 2
- PVKSZZXCZVLJLL-UHFFFAOYSA-N 4-[2-amino-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]butanoic acid Chemical compound NC1=NC(CCCC(O)=O)=CC(C=2C3=CC=CN=C3NC=2)=N1 PVKSZZXCZVLJLL-UHFFFAOYSA-N 0.000 claims description 2
- BMMMEYORLTZXLC-UHFFFAOYSA-N 4-[3-(2-amino-6-ethylpyrimidin-4-yl)-1h-pyrrolo[2,3-b]pyridin-5-yl]benzamide Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=CC(=CC=2)C(N)=O)=N1 BMMMEYORLTZXLC-UHFFFAOYSA-N 0.000 claims description 2
- AKGXXJDSHBUCJM-UHFFFAOYSA-N 4-[3-(4-methylpiperazin-1-yl)propyl]-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1CCCC1=CC(C=2C3=CC=CN=C3NC=2)=NC(N)=N1 AKGXXJDSHBUCJM-UHFFFAOYSA-N 0.000 claims description 2
- VTDIKVARKKKDDD-UHFFFAOYSA-N 4-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]-6-ethylpyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C2=C(ON=C2C)C)=N1 VTDIKVARKKKDDD-UHFFFAOYSA-N 0.000 claims description 2
- OAHPBQMQMWLROW-UHFFFAOYSA-N 4-[5-(6-aminopyridin-3-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]-6-ethylpyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=NC(N)=CC=2)=N1 OAHPBQMQMWLROW-UHFFFAOYSA-N 0.000 claims description 2
- QJMYNQJDSDDTCX-UHFFFAOYSA-N 4-[5-[6-(dimethylamino)pyridin-3-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]-6-ethylpyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=NC(=CC=2)N(C)C)=N1 QJMYNQJDSDDTCX-UHFFFAOYSA-N 0.000 claims description 2
- UVEAOKWJPIHOQT-UHFFFAOYSA-N 4-ethyl-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC=CN=C3NC=2)=N1 UVEAOKWJPIHOQT-UHFFFAOYSA-N 0.000 claims description 2
- XNLWNRNZJJUBAO-UHFFFAOYSA-N 4-ethyl-6-(2-methyl-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC=CN=C3NC=2C)=N1 XNLWNRNZJJUBAO-UHFFFAOYSA-N 0.000 claims description 2
- FBDUTCALCWFWBD-UHFFFAOYSA-N 4-ethyl-6-(5-phenyl-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=CC=CC=2)=N1 FBDUTCALCWFWBD-UHFFFAOYSA-N 0.000 claims description 2
- QDMKNNFWIFASRH-UHFFFAOYSA-N 4-ethyl-6-(5-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=NC=CC=2)=N1 QDMKNNFWIFASRH-UHFFFAOYSA-N 0.000 claims description 2
- XXEDJRFAGXDPJH-UHFFFAOYSA-N 4-ethyl-6-(5-pyridin-4-yl-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=CN=CC=2)=N1 XXEDJRFAGXDPJH-UHFFFAOYSA-N 0.000 claims description 2
- YYBPZWIFCIMNCY-UHFFFAOYSA-N 4-ethyl-6-[5-(1,3,5-trimethylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C2=C(N(C)N=C2C)C)=N1 YYBPZWIFCIMNCY-UHFFFAOYSA-N 0.000 claims description 2
- HNXOSEYAHXEERE-UHFFFAOYSA-N 4-ethyl-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=N1 HNXOSEYAHXEERE-UHFFFAOYSA-N 0.000 claims description 2
- PVSBZGKHXQOJSS-UHFFFAOYSA-N 4-ethyl-6-[5-(1-propan-2-ylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C2=CN(N=C2)C(C)C)=N1 PVSBZGKHXQOJSS-UHFFFAOYSA-N 0.000 claims description 2
- IVPOFDCEHKLJIL-UHFFFAOYSA-N 4-ethyl-6-[5-(1h-pyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C2=CNN=C2)=N1 IVPOFDCEHKLJIL-UHFFFAOYSA-N 0.000 claims description 2
- ALKWULYFERWLTF-UHFFFAOYSA-N 4-ethyl-6-[5-(1h-pyrazol-5-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2NN=CC=2)=N1 ALKWULYFERWLTF-UHFFFAOYSA-N 0.000 claims description 2
- RHKPHYBFBLSRJS-UHFFFAOYSA-N 4-ethyl-6-[5-(6-fluoro-4-methylpyridin-3-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C(=CC(F)=NC=2)C)=N1 RHKPHYBFBLSRJS-UHFFFAOYSA-N 0.000 claims description 2
- FUJVXFVFHBMKTN-UHFFFAOYSA-N 4-ethyl-6-[5-(furan-2-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2OC=CC=2)=N1 FUJVXFVFHBMKTN-UHFFFAOYSA-N 0.000 claims description 2
- UCPCTKLUCPTSCC-UHFFFAOYSA-N 4-ethyl-6-[5-[1-(2-methylpropyl)pyrazol-4-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C2=CN(CC(C)C)N=C2)=N1 UCPCTKLUCPTSCC-UHFFFAOYSA-N 0.000 claims description 2
- AGSGFXNFFGVSSJ-UHFFFAOYSA-N 5-[3-(2-amino-6-ethylpyrimidin-4-yl)-1h-pyrrolo[2,3-b]pyridin-5-yl]-n-methylpyridine-2-carboxamide Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C=2C=NC(=CC=2)C(=O)NC)=N1 AGSGFXNFFGVSSJ-UHFFFAOYSA-N 0.000 claims description 2
- XFRBWLNDIKXZAP-UHFFFAOYSA-N [2-amino-6-(1-benzylpyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]methanol Chemical compound NC1=NC(CO)=CC(C=2C3=CC=CN=C3N(CC=3C=CC=CC=3)C=2)=N1 XFRBWLNDIKXZAP-UHFFFAOYSA-N 0.000 claims description 2
- VSIVKFILRCFMSI-UHFFFAOYSA-N [2-amino-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]methanol Chemical compound NC1=NC(CO)=CC(C=2C3=CC=CN=C3NC=2)=N1 VSIVKFILRCFMSI-UHFFFAOYSA-N 0.000 claims description 2
- AKQZEFRALAUBFS-UHFFFAOYSA-N ilamine Natural products COC(C)C(O)(C(=O)OCC1=CCN2CCCC12)C(C)(C)O AKQZEFRALAUBFS-UHFFFAOYSA-N 0.000 claims 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- RWUWQCURRPGOMN-UHFFFAOYSA-N 4-(3-pyrrolidin-1-ylpropyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CN=C3NC=2)=NC(N)=NC=1CCCN1CCCC1 RWUWQCURRPGOMN-UHFFFAOYSA-N 0.000 claims 1
- HLXNKYDHBJLBDL-UHFFFAOYSA-N 4-(4-propylcyclohexyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1CC(CCC)CCC1C1=CC(C=2C3=CC=CN=C3NC=2)=NC(N)=N1 HLXNKYDHBJLBDL-UHFFFAOYSA-N 0.000 claims 1
- SHUSZGLKSCNYGH-UHFFFAOYSA-N 4-(4-propylphenyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1=CC(CCC)=CC=C1C1=CC(C=2C3=CC=CN=C3NC=2)=NC(N)=N1 SHUSZGLKSCNYGH-UHFFFAOYSA-N 0.000 claims 1
- QGLYUVUPCHPMII-UHFFFAOYSA-N 4-(aminomethyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(CN)=CC(C=2C3=CC=CN=C3NC=2)=N1 QGLYUVUPCHPMII-UHFFFAOYSA-N 0.000 claims 1
- FEKSFDCTRWZXJB-UHFFFAOYSA-N 4-(piperidin-4-ylmethyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CN=C3NC=2)=NC(N)=NC=1CC1CCNCC1 FEKSFDCTRWZXJB-UHFFFAOYSA-N 0.000 claims 1
- HVMCMFDCPBNMCE-UHFFFAOYSA-N 4-[(1-methylpiperidin-4-yl)methyl]-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCC1CC1=CC(C=2C3=CC=CN=C3NC=2)=NC(N)=N1 HVMCMFDCPBNMCE-UHFFFAOYSA-N 0.000 claims 1
- CPVLUPMZXGERKO-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(CN(C)C)=CC(C=2C3=CC=CN=C3NC=2)=N1 CPVLUPMZXGERKO-UHFFFAOYSA-N 0.000 claims 1
- IPAWFNRWGZPHID-UHFFFAOYSA-N 4-ethyl-6-[5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC(=CN=C3NC=2)C2=CN(N=C2)C2CCN(C)CC2)=N1 IPAWFNRWGZPHID-UHFFFAOYSA-N 0.000 claims 1
- YFEPOPGVIXMOQY-UHFFFAOYSA-N 4-pentyl-6-(1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC(CCCCC)=CC(C=2C3=CC=CN=C3NC=2)=N1 YFEPOPGVIXMOQY-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 230000001351 cycling effect Effects 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- 229910000510 noble metal Inorganic materials 0.000 description 1
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- 210000001672 ovary Anatomy 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- YNWXYUIDHAWPLF-UHFFFAOYSA-N tert-butyl 3-iodopyrrolo[2,3-b]pyridine-1-carboxylate Chemical compound C1=CN=C2N(C(=O)OC(C)(C)C)C=C(I)C2=C1 YNWXYUIDHAWPLF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007028515 | 2007-06-21 | ||
| DE102007028515A DE102007028515A1 (de) | 2007-06-21 | 2007-06-21 | 6-(Pyrrolopyridinyl)-pyrimidinyl-2-amin-derivate |
| PCT/EP2008/004151 WO2008155000A1 (de) | 2007-06-21 | 2008-05-23 | 6-(pyrrolopyridinyl)- pyrimidin-2-yl-amin-derivate und ihre verwendung zur behandlung von krebs und aids |
Publications (1)
| Publication Number | Publication Date |
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| ES2533873T3 true ES2533873T3 (es) | 2015-04-15 |
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| CN (1) | CN101679425B (cg-RX-API-DMAC7.html) |
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| CA (1) | CA2691223C (cg-RX-API-DMAC7.html) |
| DE (1) | DE102007028515A1 (cg-RX-API-DMAC7.html) |
| EA (1) | EA016160B1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2533873T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL202828A0 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2009013341A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008155000A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA201000432B (cg-RX-API-DMAC7.html) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2683398A1 (en) * | 2007-04-10 | 2008-10-16 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| DE102008031517A1 (de) * | 2008-07-03 | 2010-01-07 | Merck Patent Gmbh | Pyrrolopyridinyl-pyrimidin-2-yl-amin-derivate |
| DE102009019962A1 (de) * | 2009-05-05 | 2010-11-11 | Merck Patent Gmbh | 3-([1,2,3]Triazol-4-yl)-pyrrolo[2,3-b]pyridinderivate |
| DE102009060174A1 (de) | 2009-12-23 | 2011-06-30 | Merck Patent GmbH, 64293 | Pyrrolopyridinyl-pyrimidin-2-yl-amin-derivate |
| DE102009060175A1 (de) | 2009-12-23 | 2011-06-30 | Merck Patent GmbH, 64293 | Pyrrolo[2,3-d] pyrazin-7-yl-pyrimidin-Verbindungen |
| DE102010050558A1 (de) * | 2010-11-05 | 2012-05-10 | Merck Patent Gmbh | 1H-Pyrrolo[2,3-b]pyridinderivate |
| DE102010053347A1 (de) | 2010-12-03 | 2012-06-06 | Merck Patent Gmbh | 3-Hetaryl-substituierte Pyrrolo[2,3-b] pyridin-derivative als PDK1-Inhibitoren |
| DE102011009961A1 (de) | 2011-02-01 | 2012-08-02 | Merck Patent Gmbh | 7-Azaindolderivate |
| EP3255049A1 (en) | 2012-06-29 | 2017-12-13 | Pfizer Inc | Novel 4-(substituted-amino)-7h-pyrrolo[2,3-d]pyrimidines as lrrk2 inhibitors |
| WO2014111496A1 (en) * | 2013-01-18 | 2014-07-24 | F. Hoffmann-La Roche Ag | 3-substituted pyrazoles and use as dlk inhibitors |
| RU2680100C9 (ru) * | 2013-03-15 | 2019-04-18 | Плексксикон Инк. | Гетероциклические соединения и их применения |
| US20140303121A1 (en) | 2013-03-15 | 2014-10-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| JP6487921B2 (ja) | 2013-12-17 | 2019-03-20 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規の３，４−二置換−１Ｈ−ピロロ［２，３−ｂ］ピリジンおよび４，５−二置換−７Ｈ−ピロロ［２，３−ｃ］ピリダジン |
| KR102161364B1 (ko) | 2015-09-14 | 2020-09-29 | 화이자 인코포레이티드 | LRRK2 억제제로서 이미다조[4,5-c]퀴놀린 및 이미다조[4,5-c][1,5]나프티리딘 유도체 |
| WO2017161004A1 (en) * | 2016-03-15 | 2017-09-21 | University Of South Florida | PKCδ INHIBITOR FORMULATIONS AND USES THEREOF CROSS-REFERENCE TO RELATED APPLICATIONS |
| RU2738646C2 (ru) | 2016-04-01 | 2020-12-15 | РЕКЬЮРИУМ АйПи ХОЛДИНГС, ЛЛС | Модуляторы эстрогеновых рецепторов |
| JP7675519B2 (ja) | 2017-10-13 | 2025-05-13 | オプナ バイオ ソシエテ アノニム | キナーゼを調節するための化合物の固体形態 |
| AU2020271836B2 (en) * | 2019-04-09 | 2025-11-13 | Opna Bio SA | Condensed azines for EP300 or CBP modulation and indications therefor |
| KR20220044528A (ko) | 2019-08-06 | 2022-04-08 | 리커리엄 아이피 홀딩스, 엘엘씨 | 돌연변이체를 치료하기 위한 에스트로겐 수용체 조절제 |
| CN118772140A (zh) * | 2023-04-07 | 2024-10-15 | 四川大学 | 一类化合物及其在治疗hDHODH介导的疾病中的用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5747469A (en) | 1991-03-06 | 1998-05-05 | Board Of Regents, The University Of Texas System | Methods and compositions comprising DNA damaging agents and p53 |
| GB9904387D0 (en) | 1999-02-25 | 1999-04-21 | Pharmacia & Upjohn Spa | Antitumour synergistic composition |
| US6265434B1 (en) | 1999-04-06 | 2001-07-24 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| PL2332940T3 (pl) * | 2004-03-30 | 2013-03-29 | Vertex Pharma | Azaindole użyteczne jako inhibitory JAK i innych kinaz białkowych |
| US20080153869A1 (en) * | 2004-06-14 | 2008-06-26 | Bressi Jerome C | Kinase Inhibitors |
| WO2006015123A1 (en) * | 2004-07-27 | 2006-02-09 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| EP1828180A4 (en) * | 2004-12-08 | 2010-09-15 | Glaxosmithkline Llc | 1H-pyrrolo [2,3-BETA] PYRIDINE |
| CN101218241B (zh) * | 2005-05-16 | 2011-02-16 | Irm责任有限公司 | 用作蛋白激酶抑制剂的吡咯并吡啶衍生物 |
| DE102006012617A1 (de) * | 2006-03-20 | 2007-09-27 | Merck Patent Gmbh | 4-(Pyrrolopyridinyl)-pyrimidinyl-2-amin-derivate |
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2007
- 2007-06-21 DE DE102007028515A patent/DE102007028515A1/de not_active Withdrawn
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2008
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- 2008-05-23 EA EA201000004A patent/EA016160B1/ru not_active IP Right Cessation
- 2008-05-23 EP EP08758743.2A patent/EP2155745B1/de not_active Not-in-force
- 2008-05-23 ES ES08758743.2T patent/ES2533873T3/es active Active
- 2008-05-23 CN CN2008800197101A patent/CN101679425B/zh not_active Expired - Fee Related
- 2008-05-23 AU AU2008266584A patent/AU2008266584B2/en not_active Ceased
- 2008-05-23 US US12/664,791 patent/US8546390B2/en not_active Expired - Fee Related
- 2008-05-23 BR BRPI0812944-4A2A patent/BRPI0812944A2/pt not_active IP Right Cessation
- 2008-05-23 WO PCT/EP2008/004151 patent/WO2008155000A1/de not_active Ceased
- 2008-05-23 KR KR1020107001385A patent/KR20100040862A/ko not_active Withdrawn
- 2008-05-23 CA CA2691223A patent/CA2691223C/en not_active Expired - Fee Related
- 2008-05-23 MX MX2009013341A patent/MX2009013341A/es not_active Application Discontinuation
- 2008-06-20 AR ARP080102634A patent/AR067081A1/es unknown
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2009
- 2009-12-17 IL IL202828A patent/IL202828A0/en unknown
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2010
- 2010-01-20 ZA ZA201000432A patent/ZA201000432B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008266584B2 (en) | 2013-04-04 |
| CA2691223A1 (en) | 2008-12-24 |
| CN101679425B (zh) | 2013-11-06 |
| CA2691223C (en) | 2015-12-01 |
| EP2155745A1 (de) | 2010-02-24 |
| WO2008155000A1 (de) | 2008-12-24 |
| MX2009013341A (es) | 2010-01-18 |
| BRPI0812944A2 (pt) | 2014-12-16 |
| JP5411849B2 (ja) | 2014-02-12 |
| US20110082140A1 (en) | 2011-04-07 |
| EP2155745B1 (de) | 2015-01-28 |
| EA201000004A1 (ru) | 2010-06-30 |
| EA016160B1 (ru) | 2012-02-28 |
| ZA201000432B (en) | 2010-10-27 |
| DE102007028515A1 (de) | 2008-12-24 |
| AU2008266584A1 (en) | 2008-12-24 |
| CN101679425A (zh) | 2010-03-24 |
| US8546390B2 (en) | 2013-10-01 |
| KR20100040862A (ko) | 2010-04-21 |
| JP2010530376A (ja) | 2010-09-09 |
| AR067081A1 (es) | 2009-09-30 |
| IL202828A0 (en) | 2010-06-30 |
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