ES2537412T3 - Derivados de pirrolopiridinil-pirimidin-2-il-amina - Google Patents

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Publication number

ES2537412T3

ES2537412T3 ES10778880.4T ES10778880T ES2537412T3 ES 2537412 T3 ES2537412 T3 ES 2537412T3 ES 10778880 T ES10778880 T ES 10778880T ES 2537412 T3 ES2537412 T3 ES 2537412T3

Authority

ES

Spain

Prior art keywords

pyridin

pyrimidin

pyrrolo

pyrazol

amino

Prior art date

2009-12-23

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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• HKBDDSSWUICVMT-UHFFFAOYSA-N n-pyrimidin-2-yl-1h-pyrrolo[3,2-b]pyridin-2-amine Chemical class C=1C2=NC=CC=C2NC=1NC1=NC=CC=N1 HKBDDSSWUICVMT-UHFFFAOYSA-N 0.000 title description 2
• -1 1-methyl-1H-pyrazol-4-yl Chemical group 0.000 claims abstract description 135
• 150000001875 compounds Chemical class 0.000 claims abstract description 110
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 50
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims abstract description 8
• IUHGQADXSZQXKJ-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(N)=NC=1C(O)(CC)C1=CC=NC=C1 IUHGQADXSZQXKJ-UHFFFAOYSA-N 0.000 claims abstract description 7
• CJPHUGKUQMKLIV-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-3-ylethanol Chemical compound C1=NN(C)C=C1C1=CN=C(NC=C2C=3N=C(N)N=C(C=3)C(C)(O)C=3C=NC=CC=3)C2=C1 CJPHUGKUQMKLIV-UHFFFAOYSA-N 0.000 claims abstract description 5
• ZDAGAIQHHKISRX-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-4-ylethanol Chemical compound C1=NN(C)C=C1C1=CN=C(NC=C2C=3N=C(N)N=C(C=3)C(C)(O)C=3C=CN=CC=3)C2=C1 ZDAGAIQHHKISRX-UHFFFAOYSA-N 0.000 claims abstract description 5
• JYPMXANABMTVJC-UHFFFAOYSA-N 4-[1-(3-fluoropyridin-4-yl)-1-(methoxymethoxy)propyl]-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound C=1C=NC=C(F)C=1C(OCOC)(CC)C(N=C(N)N=1)=CC=1C(C1=C2)=CNC1=NC=C2C=1C=NN(C)C=1 JYPMXANABMTVJC-UHFFFAOYSA-N 0.000 claims abstract description 5
• BANGIQBRTKJIAH-UHFFFAOYSA-N 1-[2-amino-6-[5-[1-(difluoromethyl)pyrazol-4-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-phenylethanol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(N=C2)C(F)F)=NC(N)=NC=1C(O)(C)C1=CC=CC=C1 BANGIQBRTKJIAH-UHFFFAOYSA-N 0.000 claims abstract description 4
• GOBVMZSMROBKHC-UHFFFAOYSA-N 1-[2-methoxy-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(OC)=NC=1C(O)(CC)C1=CC=NC=C1 GOBVMZSMROBKHC-UHFFFAOYSA-N 0.000 claims abstract description 4
• XNKVGIGAHJWCBZ-UHFFFAOYSA-N 4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-6-[1-(3-fluorophenyl)-1-(methoxymethoxy)ethyl]pyrimidin-2-amine Chemical compound N=1C(N)=NC(C=2C3=CC(Br)=CN=C3NC=2)=C(F)C=1C(C)(OCOC)C1=CC=CC(F)=C1 XNKVGIGAHJWCBZ-UHFFFAOYSA-N 0.000 claims abstract description 4
• OHYONXOTEZJZRZ-UHFFFAOYSA-N 4-[1-(methoxymethoxy)-1-phenylethyl]-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(N)=NC=1C(C)(OCOC)C1=CC=CC=C1 OHYONXOTEZJZRZ-UHFFFAOYSA-N 0.000 claims abstract description 4
• DXBBHJFQBVLQLG-UHFFFAOYSA-N 1-[2-amino-6-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]-1-phenylbutan-1-ol Chemical compound C=1C(C=2C3=CC(Br)=CN=C3NC=2)=NC(N)=NC=1C(O)(CCC)C1=CC=CC=C1 DXBBHJFQBVLQLG-UHFFFAOYSA-N 0.000 claims abstract description 3
• FSPGWWFGLUNJAD-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-[4-(hydroxymethyl)phenyl]ethanol Chemical compound C1=NN(C)C=C1C1=CN=C(NC=C2C=3N=C(N)N=C(C=3)C(C)(O)C=3C=CC(CO)=CC=3)C2=C1 FSPGWWFGLUNJAD-UHFFFAOYSA-N 0.000 claims abstract description 3
• OZWHBGBWHSOYHU-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-3-(dimethylamino)-1-phenylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(N)=NC=1C(O)(CCN(C)C)C1=CC=CC=C1 OZWHBGBWHSOYHU-UHFFFAOYSA-N 0.000 claims abstract description 3
• MUVMMJCSJJMOIA-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-3-(dimethylamino)-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(N)=NC=1C(O)(CCN(C)C)C1=CC=NC=C1 MUVMMJCSJJMOIA-UHFFFAOYSA-N 0.000 claims abstract description 3
• OZPMORMSDAIPDE-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylsulfonylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-phenylethanol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(N=C2)S(C)(=O)=O)=NC(N)=NC=1C(O)(C)C1=CC=CC=C1 OZPMORMSDAIPDE-UHFFFAOYSA-N 0.000 claims abstract description 3
• VVJBMXHAQQAQFQ-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-piperidin-4-ylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-phenylethanol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(N=C2)C2CCNCC2)=NC(N)=NC=1C(O)(C)C1=CC=CC=C1 VVJBMXHAQQAQFQ-UHFFFAOYSA-N 0.000 claims abstract description 3
• CAWCSBUXLNNHQY-UHFFFAOYSA-N 1-[2-amino-6-[5-[1-(2-fluoroethyl)pyrazol-4-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(CCF)N=C2)=NC(N)=NC=1C(O)(CC)C1=CC=NC=C1 CAWCSBUXLNNHQY-UHFFFAOYSA-N 0.000 claims abstract description 3
• NTAVFUAVCQKJRJ-UHFFFAOYSA-N 1-[2-amino-6-[5-[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(CCN3CCCC3)N=C2)=NC(N)=NC=1C(O)(CC)C1=CC=NC=C1 NTAVFUAVCQKJRJ-UHFFFAOYSA-N 0.000 claims abstract description 3
• TUEINUZPSISIRR-UHFFFAOYSA-N 1-[2-amino-6-[5-[4-(hydroxymethyl)phenyl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-(3-fluorophenyl)ethanol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C=2C=CC(CO)=CC=2)=NC(N)=NC=1C(O)(C)C1=CC=CC(F)=C1 TUEINUZPSISIRR-UHFFFAOYSA-N 0.000 claims abstract description 3
• IFMSEJRYUKJXCW-UHFFFAOYSA-N 1-[2-amino-6-[5-[4-(hydroxymethyl)phenyl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-(3-fluorophenyl)propan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C=2C=CC(CO)=CC=2)=NC(N)=NC=1C(O)(CC)C1=CC=CC(F)=C1 IFMSEJRYUKJXCW-UHFFFAOYSA-N 0.000 claims abstract description 3
• JERFJQNQUZBKSL-UHFFFAOYSA-N 1-[6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC=NC=1C(O)(CC)C1=CC=NC=C1 JERFJQNQUZBKSL-UHFFFAOYSA-N 0.000 claims abstract description 3
• SDRPVQQHWOFKJD-UHFFFAOYSA-N 2-[4-[3-[2-amino-6-(1-hydroxy-1-phenylethyl)pyrimidin-4-yl]-1h-pyrrolo[2,3-b]pyridin-5-yl]pyrazol-1-yl]-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1=C(C=2C=C3C(C=4N=C(N)N=C(C=4)C(C)(O)C=4C=CC=CC=4)=CNC3=NC=2)C=NN1C(C)C(=O)N1CCCC1 SDRPVQQHWOFKJD-UHFFFAOYSA-N 0.000 claims abstract description 3
• WTRYYRYBFBNAEA-LJAQVGFWSA-N 2-[4-[3-[2-amino-6-[(1s)-1-hydroxy-1-pyridin-4-ylpropyl]pyrimidin-4-yl]-1h-pyrrolo[2,3-b]pyridin-5-yl]pyrazol-1-yl]-1-piperidin-1-ylethanone Chemical compound C1([C@@](O)(CC)C=2N=C(N)N=C(C=2)C=2C3=CC(=CN=C3NC=2)C2=CN(CC(=O)N3CCCCC3)N=C2)=CC=NC=C1 WTRYYRYBFBNAEA-LJAQVGFWSA-N 0.000 claims abstract description 3
• HYSQENHLQHFXPA-UHFFFAOYSA-N 2-[4-[3-[2-amino-6-[1-(3-fluorophenyl)-1-hydroxyethyl]pyrimidin-4-yl]-1h-pyrrolo[2,3-b]pyridin-5-yl]phenyl]acetonitrile Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C=2C=CC(CC#N)=CC=2)=NC(N)=NC=1C(O)(C)C1=CC=CC(F)=C1 HYSQENHLQHFXPA-UHFFFAOYSA-N 0.000 claims abstract description 3
• SZVDFYUFUIAMSW-QFIPXVFZSA-N 4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)-6-[(1s)-1-(3-fluorophenyl)-1-(methoxymethoxy)propyl]pyrimidin-2-amine Chemical compound C1([C@@](OCOC)(CC)C=2N=C(N)N=C(C=2)C=2C3=CC(Br)=CN=C3NC=2)=CC=CC(F)=C1 SZVDFYUFUIAMSW-QFIPXVFZSA-N 0.000 claims abstract description 3
• DENCBJWMJKNFHH-UHFFFAOYSA-N 4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)-6-[1-(methoxymethoxy)-1-(2-methylphenyl)ethyl]pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC(Br)=CN=C3NC=2)=NC(N)=NC=1C(C)(OCOC)C1=CC=CC=C1C DENCBJWMJKNFHH-UHFFFAOYSA-N 0.000 claims abstract description 3
• YAOJGPWPLUWHEK-UHFFFAOYSA-N 4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)-6-[1-(methoxymethoxy)-1-phenylethyl]pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC(Br)=CN=C3NC=2)=NC(N)=NC=1C(C)(OCOC)C1=CC=CC=C1 YAOJGPWPLUWHEK-UHFFFAOYSA-N 0.000 claims abstract description 3
• AMYQMEDPTWOMTI-UHFFFAOYSA-N 4-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)-6-[1-(methoxymethoxy)-1-pyridin-4-ylpropyl]pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC(Br)=CN=C3NC=2)=NC(N)=NC=1C(OCOC)(CC)C1=CC=NC=C1 AMYQMEDPTWOMTI-UHFFFAOYSA-N 0.000 claims abstract description 3
• TUFGUQBKDYTLLN-UHFFFAOYSA-N 4-[1-(3-chloro-2-fluorophenyl)-1-(methoxymethoxy)ethyl]-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound C=1C=CC(Cl)=C(F)C=1C(C)(OCOC)C(N=C(N)N=1)=CC=1C(C1=C2)=CNC1=NC=C2C=1C=NN(C)C=1 TUFGUQBKDYTLLN-UHFFFAOYSA-N 0.000 claims abstract description 3
• FNPPNSVHLLLXAH-UHFFFAOYSA-N 4-[1-(methoxymethoxy)-1-pyridin-4-ylbutyl]-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(N)=NC=1C(OCOC)(CCC)C1=CC=NC=C1 FNPPNSVHLLLXAH-UHFFFAOYSA-N 0.000 claims abstract description 3
• DWLZKBRUXMDVBL-UHFFFAOYSA-N 1-[2-(methylamino)-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(NC)=NC=1C(O)(CC)C1=CC=NC=C1 DWLZKBRUXMDVBL-UHFFFAOYSA-N 0.000 claims abstract 4
• VBEDHERKIYUUPA-UHFFFAOYSA-N 1-[2-amino-6-[5-(1h-pyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CNN=C2)=NC(N)=NC=1C(O)(CC)C1=CC=NC=C1 VBEDHERKIYUUPA-UHFFFAOYSA-N 0.000 claims abstract 4
• RDKAKFPACSALMF-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-2-methyl-1-pyridin-4-ylpropan-1-ol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(N)=NC=1C(O)(C(C)C)C1=CC=NC=C1 RDKAKFPACSALMF-UHFFFAOYSA-N 0.000 claims abstract 2
• OOSMMRYVLKITFJ-UHFFFAOYSA-N 1-[2-amino-6-[5-[1-(thiophen-2-ylmethyl)pyrazol-4-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-phenylethanol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(CC=3SC=CC=3)N=C2)=NC(N)=NC=1C(O)(C)C1=CC=CC=C1 OOSMMRYVLKITFJ-UHFFFAOYSA-N 0.000 claims abstract 2
• UHMHKGFTCJPJHW-UHFFFAOYSA-N 2-[4-[3-[2-amino-6-[1-(methoxymethoxy)-1-(3-methylphenyl)ethyl]pyrimidin-4-yl]-1h-pyrrolo[2,3-b]pyridin-5-yl]pyrazol-1-yl]ethanol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(CCO)N=C2)=NC(N)=NC=1C(C)(OCOC)C1=CC=CC(C)=C1 UHMHKGFTCJPJHW-UHFFFAOYSA-N 0.000 claims abstract 2
• NPHOIBWXTKSGQE-UHFFFAOYSA-N 4-[1-(methoxymethoxy)-1-(2-methylphenyl)ethyl]-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound C=1C=CC=C(C)C=1C(C)(OCOC)C(N=C(N)N=1)=CC=1C(C1=C2)=CNC1=NC=C2C=1C=NN(C)C=1 NPHOIBWXTKSGQE-UHFFFAOYSA-N 0.000 claims abstract 2
• XSPFGHCSQKYWFW-UHFFFAOYSA-N 4-[1-(methoxymethoxy)-1-(3-methylphenyl)ethyl]-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(C)N=C2)=NC(N)=NC=1C(C)(OCOC)C1=CC=CC(C)=C1 XSPFGHCSQKYWFW-UHFFFAOYSA-N 0.000 claims abstract 2
• 150000003839 salts Chemical class 0.000 claims description 61
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• 238000011282 treatment Methods 0.000 claims description 33
• 206010028980 Neoplasm Diseases 0.000 claims description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 19
• 239000012453 solvate Substances 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 8
• 230000001028 anti-proliverative effect Effects 0.000 claims description 8
• 206010006187 Breast cancer Diseases 0.000 claims description 6
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• 229940079593 drug Drugs 0.000 claims description 6
• 239000003112 inhibitor Substances 0.000 claims description 6
• ADBJUXXPUBJGRD-UHFFFAOYSA-N 1-[2-amino-6-[5-[1-(2-hydroxyethyl)pyrazol-4-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-phenylethanol Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(CCO)N=C2)=NC(N)=NC=1C(O)(C)C1=CC=CC=C1 ADBJUXXPUBJGRD-UHFFFAOYSA-N 0.000 claims description 5
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• CNGHQZMMCLQZIU-UHFFFAOYSA-N 1-[2-amino-6-[5-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]-1-(2-fluorophenyl)ethanol Chemical compound C1=NN(C)C=C1C1=CN=C(NC=C2C=3N=C(N)N=C(C=3)C(C)(O)C=3C(=CC=CC=3)F)C2=C1 CNGHQZMMCLQZIU-UHFFFAOYSA-N 0.000 claims description 4
• PDFPFXXMKZRMSP-UHFFFAOYSA-N 1-[6-[5-[1-(2-hydroxyethyl)pyrazol-4-yl]-1h-pyrrolo[2,3-b]pyridin-3-yl]-2-(methylamino)pyrimidin-4-yl]-1-phenylethanol Chemical compound N=1C(NC)=NC(C=2C3=CC(=CN=C3NC=2)C2=CN(CCO)N=C2)=CC=1C(C)(O)C1=CC=CC=C1 PDFPFXXMKZRMSP-UHFFFAOYSA-N 0.000 claims description 4
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• DPYDMDOJUSRLGO-UHFFFAOYSA-N 3-[4-[3-[2-amino-6-(1-hydroxy-1-phenylethyl)pyrimidin-4-yl]-1h-pyrrolo[2,3-b]pyridin-5-yl]pyrazol-1-yl]-1-morpholin-4-ylpropan-1-one Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(CCC(=O)N3CCOCC3)N=C2)=NC(N)=NC=1C(O)(C)C1=CC=CC=C1 DPYDMDOJUSRLGO-UHFFFAOYSA-N 0.000 claims description 3
• HOOVJEYSGVGETL-UHFFFAOYSA-N 3-[4-[3-[2-amino-6-[1-(methoxymethoxy)-1-phenylethyl]pyrimidin-4-yl]-1h-pyrrolo[2,3-b]pyridin-5-yl]pyrazol-1-yl]propanoic acid Chemical compound C=1C(C=2C3=CC(=CN=C3NC=2)C2=CN(CCC(O)=O)N=C2)=NC(N)=NC=1C(C)(OCOC)C1=CC=CC=C1 HOOVJEYSGVGETL-UHFFFAOYSA-N 0.000 claims description 3
• 102000005454 Dimethylallyltranstransferase Human genes 0.000 claims description 3
• 108010006731 Dimethylallyltranstransferase Proteins 0.000 claims description 3
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 3
• 239000002671 adjuvant Substances 0.000 claims description 3
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• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 3
• AKQZEFRALAUBFS-UHFFFAOYSA-N ilamine Natural products COC(C)C(O)(C(=O)OCC1=CCN2CCCC12)C(C)(C)O AKQZEFRALAUBFS-UHFFFAOYSA-N 0.000 claims description 3
• 210000000867 larynx Anatomy 0.000 claims description 3
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• 239000012268 protein inhibitor Substances 0.000 claims description 3
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• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 3
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