JP2007523151A - ２−（ピリジン−３−イルアミノ）−ピリド［２，３−ｄ］ピリミジン−７−オン - Google Patents

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Publication number

JP2007523151A

JP2007523151A JP2006553697A JP2006553697A JP2007523151A JP 2007523151 A JP2007523151 A JP 2007523151A JP 2006553697 A JP2006553697 A JP 2006553697A JP 2006553697 A JP2006553697 A JP 2006553697A JP 2007523151 A JP2007523151 A JP 2007523151A

Authority

JP

Japan

Prior art keywords

pyrido

ylamino

pyridin

pyrimidin

piperazin

Prior art date

2004-02-18

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.)

Withdrawn

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• BXOSYWAUOOEKIH-UHFFFAOYSA-N 2-(pyridin-3-ylamino)-6h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C2=NC(=O)CC=C2C=NC=1NC1=CC=CN=C1 BXOSYWAUOOEKIH-UHFFFAOYSA-N 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 107
• -1 6-piperazin-1-yl-pyridin-3-ylamino Chemical group 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 52
• 238000000034 method Methods 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 29
• 206010028980 Neoplasm Diseases 0.000 claims description 27
• 125000000217 alkyl group Chemical group 0.000 claims description 27
• 201000011510 cancer Diseases 0.000 claims description 24
• 150000002431 hydrogen Chemical class 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 150000002148 esters Chemical class 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 150000001408 amides Chemical class 0.000 claims description 11
• 239000000651 prodrug Substances 0.000 claims description 11
• 229940002612 prodrug Drugs 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 9
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 9
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 210000000214 mouth Anatomy 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• 230000002159 abnormal effect Effects 0.000 claims description 7
• 230000004663 cell proliferation Effects 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 208000009956 adenocarcinoma Diseases 0.000 claims description 5
• 208000029742 colonic neoplasm Diseases 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 239000011593 sulfur Substances 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• RXUXPYCEJKWINO-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-5-methyl-2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(C=N1)=CC=C1N1CCOCC1 RXUXPYCEJKWINO-UHFFFAOYSA-N 0.000 claims description 4
• PSRAOXPOEYRNJN-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-5-methyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(C=N1)=CC=C1N1CCNCC1 PSRAOXPOEYRNJN-UHFFFAOYSA-N 0.000 claims description 4
• NXIFVKBQTCUXOE-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=NC(=CC=3)N3CCOCC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 NXIFVKBQTCUXOE-UHFFFAOYSA-N 0.000 claims description 4
• PYINCEJKNQPDTH-UHFFFAOYSA-N 8-cyclopentyl-2-[(6-methoxypyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCC3)C2=N1 PYINCEJKNQPDTH-UHFFFAOYSA-N 0.000 claims description 4
• HODVWRBGNQTDGL-UHFFFAOYSA-N 8-propan-2-yl-2-(pyridin-3-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C)C2=NC=1NC1=CC=CN=C1 HODVWRBGNQTDGL-UHFFFAOYSA-N 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
• 150000002825 nitriles Chemical class 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 230000035755 proliferation Effects 0.000 claims description 4
• 206010038038 rectal cancer Diseases 0.000 claims description 4
• 201000001275 rectum cancer Diseases 0.000 claims description 4
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 3
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
• WMEIBDGEPLSTOW-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=NC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 WMEIBDGEPLSTOW-UHFFFAOYSA-N 0.000 claims description 3
• 208000003200 Adenoma Diseases 0.000 claims description 3
• 206010001233 Adenoma benign Diseases 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 208000017604 Hodgkin disease Diseases 0.000 claims description 3
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 208000018501 Lymphatic disease Diseases 0.000 claims description 3
• 206010029260 Neuroblastoma Diseases 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 201000010208 Seminoma Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 3
• 229960001171 acetohydroxamic acid Drugs 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
• 201000007455 central nervous system cancer Diseases 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 208000003849 large cell carcinoma Diseases 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
• 201000007270 liver cancer Diseases 0.000 claims description 3
• 208000014018 liver neoplasm Diseases 0.000 claims description 3
• 208000018555 lymphatic system disease Diseases 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 210000002464 muscle smooth vascular Anatomy 0.000 claims description 3
• 230000002980 postoperative effect Effects 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 210000003491 skin Anatomy 0.000 claims description 3
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
• XRTACFOJSFSFIW-UHFFFAOYSA-N 2-[(6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-yl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3SC=CN=3)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCNCC1 XRTACFOJSFSFIW-UHFFFAOYSA-N 0.000 claims description 2
• GHYUVIGBANFJNG-UHFFFAOYSA-N 2-[[6-(3,5-dimethylpiperazin-1-yl)pyridin-3-yl]amino]-6-(hydroxymethyl)-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=C(CO)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CC(C)NC(C)C1 GHYUVIGBANFJNG-UHFFFAOYSA-N 0.000 claims description 2
• JZJNGDAXALEGQI-UHFFFAOYSA-N 2-[[6-(3,5-dimethylpiperazin-1-yl)pyridin-3-yl]amino]-6-(hydroxymethyl)-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(CO)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CC(C)NC(C)C1 JZJNGDAXALEGQI-UHFFFAOYSA-N 0.000 claims description 2
• ZKWJVCJSTZSQSL-UHFFFAOYSA-N 2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]-6-phenoxy-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(OC=3C=CC=CC=3)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCN(C)CC1 ZKWJVCJSTZSQSL-UHFFFAOYSA-N 0.000 claims description 2
• ICEMITYCGODOAD-UHFFFAOYSA-N 3-[6-fluoro-5-methyl-7-oxo-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-8-yl]propanoic acid Chemical compound N=1C=C2C(C)=C(F)C(=O)N(CCC(O)=O)C2=NC=1NC(C=N1)=CC=C1N1CCNCC1 ICEMITYCGODOAD-UHFFFAOYSA-N 0.000 claims description 2
• WXWVSYQRYRNFBY-UHFFFAOYSA-N 3-[6-fluoro-7-oxo-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-8-yl]propanoic acid Chemical compound N=1C=C2C=C(F)C(=O)N(CCC(=O)O)C2=NC=1NC(C=N1)=CC=C1N1CCNCC1 WXWVSYQRYRNFBY-UHFFFAOYSA-N 0.000 claims description 2
• MXCBDHVXPSUVIZ-UHFFFAOYSA-N 5-methyl-2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]-6-phenoxy-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=C(OC=3C=CC=CC=3)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCN(C)CC1 MXCBDHVXPSUVIZ-UHFFFAOYSA-N 0.000 claims description 2
• GYSUUFRNQZYUNG-UHFFFAOYSA-N 6-acetyl-2-[(5-chloro-6-piperazin-1-ylpyridin-3-yl)amino]-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=C(C(C)=O)C(=O)N(C(C)C)C2=NC=1NC(C=C1Cl)=CN=C1N1CCNCC1 GYSUUFRNQZYUNG-UHFFFAOYSA-N 0.000 claims description 2
• ACFOEHLOSQTBFN-UHFFFAOYSA-N 6-acetyl-2-[(5-chloro-6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C(C)=O)C(=O)N(C(C)C)C2=NC=1NC(C=C1Cl)=CN=C1N1CCNCC1 ACFOEHLOSQTBFN-UHFFFAOYSA-N 0.000 claims description 2
• DHUZXMJJCAHCPH-UHFFFAOYSA-N 6-acetyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C(C)=O)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCNCC1 DHUZXMJJCAHCPH-UHFFFAOYSA-N 0.000 claims description 2
• LKCSZNHDJJQUDO-UHFFFAOYSA-N 6-acetyl-5-methyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=C(C(C)=O)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCNCC1 LKCSZNHDJJQUDO-UHFFFAOYSA-N 0.000 claims description 2
• DJJBZVAMSAAMPS-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-2-[[6-(1,4-diazepan-1-yl)pyridin-3-yl]amino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(C=N1)=CC=C1N1CCCNCC1 DJJBZVAMSAAMPS-UHFFFAOYSA-N 0.000 claims description 2
• SZHNTQBSCCDDTP-UHFFFAOYSA-N 6-acetyl-8-cyclopentyl-2-[[6-(1,4-diazepan-1-yl)pyridin-3-yl]amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=CC2=CN=C1NC(C=N1)=CC=C1N1CCCNCC1 SZHNTQBSCCDDTP-UHFFFAOYSA-N 0.000 claims description 2
• IZWKSYQYHZKCBL-UHFFFAOYSA-N 6-anilino-8-(2-cyclopropylethyl)-2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C2=CN=C(NC=3C=NC(=CC=3)N3CCOCC3)N=C2N(CCC2CC2)C(=O)C=1NC1=CC=CC=C1 IZWKSYQYHZKCBL-UHFFFAOYSA-N 0.000 claims description 2
• ZXJGRNNMEMXMHV-UHFFFAOYSA-N 6-anilino-8-(2-cyclopropylethyl)-5-methyl-2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCC2CC2)C2=NC(NC=3C=NC(=CC=3)N3CCOCC3)=NC=C2C(C)=C1NC1=CC=CC=C1 ZXJGRNNMEMXMHV-UHFFFAOYSA-N 0.000 claims description 2
• LXZCYWJQYXBEQL-UHFFFAOYSA-N 6-benzyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(CC=3C=CC=CC=3)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCNCC1 LXZCYWJQYXBEQL-UHFFFAOYSA-N 0.000 claims description 2
• PCPLYCKSHDHXPE-UHFFFAOYSA-N 6-benzyl-2-[[6-(2-methoxyethoxy)pyridin-3-yl]amino]-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=NC(OCCOC)=CC=C1NC1=NC=C(C(C)=C(CC=2C=CC=CC=2)C(=O)N2C(C)C)C2=N1 PCPLYCKSHDHXPE-UHFFFAOYSA-N 0.000 claims description 2
• ZZCWERBNMNIVBT-UHFFFAOYSA-N 6-benzyl-2-[[6-(2-methoxyethoxy)pyridin-3-yl]amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=NC(OCCOC)=CC=C1NC1=NC=C(C=C(CC=2C=CC=CC=2)C(=O)N2C(C)C)C2=N1 ZZCWERBNMNIVBT-UHFFFAOYSA-N 0.000 claims description 2
• COAONMXILAOQEL-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(Br)=CC2=CN=C1NC(C=N1)=CC=C1N1CCNCC1 COAONMXILAOQEL-UHFFFAOYSA-N 0.000 claims description 2
• RZGWHKQRFXPQCW-UHFFFAOYSA-N 6-chloro-5-methyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=C(Cl)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCNCC1 RZGWHKQRFXPQCW-UHFFFAOYSA-N 0.000 claims description 2
• SYYKFFAMJNLHPZ-UHFFFAOYSA-N 6-ethyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C)C)C(=O)C(CC)=CC2=CN=C1NC(C=N1)=CC=C1N1CCNCC1 SYYKFFAMJNLHPZ-UHFFFAOYSA-N 0.000 claims description 2
• OUIYDOZEILYEER-UHFFFAOYSA-N 6-ethyl-8-(2-methoxyethyl)-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCOC)C(=O)C(CC)=CC2=CN=C1NC(C=N1)=CC=C1N1CCNCC1 OUIYDOZEILYEER-UHFFFAOYSA-N 0.000 claims description 2
• YITJUFUSEPCUJX-UHFFFAOYSA-N 6-ethyl-8-(2-methoxyethyl)-5-methyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCOC)C(=O)C(CC)=C(C)C2=CN=C1NC(C=N1)=CC=C1N1CCNCC1 YITJUFUSEPCUJX-UHFFFAOYSA-N 0.000 claims description 2
• WMOJNXOQMYZLIB-UHFFFAOYSA-N 6-ethynyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C#C)C(=O)N(C(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCNCC1 WMOJNXOQMYZLIB-UHFFFAOYSA-N 0.000 claims description 2
• JWYCJOFYBBZCCR-UHFFFAOYSA-N 8-[2-(dimethylamino)ethyl]-6-ethynyl-5-methyl-2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=C(C#C)C(=O)N(CCN(C)C)C2=NC=1NC(C=N1)=CC=C1N1CCOCC1 JWYCJOFYBBZCCR-UHFFFAOYSA-N 0.000 claims description 2
• KBLKSMPPZYUQAB-UHFFFAOYSA-N 8-benzyl-6-ethenyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3C=CC=CC=3)C(=O)C(C=C)=CC2=CN=C1NC(C=N1)=CC=C1N1CCNCC1 KBLKSMPPZYUQAB-UHFFFAOYSA-N 0.000 claims description 2
• INSFBQSSSGSXHU-UHFFFAOYSA-N 8-benzyl-6-ethenyl-5-methyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=NC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(C=C)C(=O)N1CC1=CC=CC=C1 INSFBQSSSGSXHU-UHFFFAOYSA-N 0.000 claims description 2
• UUHHKLZMMAJVJK-UHFFFAOYSA-N 8-cyclopentyl-6-ethyl-5-methyl-2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(CC)=C(C)C2=CN=C1NC(C=N1)=CC=C1N1CCNCC1 UUHHKLZMMAJVJK-UHFFFAOYSA-N 0.000 claims description 2
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• JOLGSHXGVFCISU-UHFFFAOYSA-N ethyl 7-oxo-2-[(6-piperazin-1-ylpyridin-3-yl)amino]-8-propan-2-ylpyrido[2,3-d]pyrimidine-6-carboxylate Chemical compound N1=C2N(C(C)C)C(=O)C(C(=O)OCC)=CC2=CN=C1NC(C=N1)=CC=C1N1CCNCC1 JOLGSHXGVFCISU-UHFFFAOYSA-N 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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