KR20000070751A - 세포 증식 억제제로서의 피리도[2,3-ｄ]피리미딘 및 4-아미노피리미딘 - Google Patents

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Publication number

KR20000070751A

KR20000070751A KR1019997007010A KR19997007010A KR20000070751A KR 20000070751 A KR20000070751 A KR 20000070751A KR 1019997007010 A KR1019997007010 A KR 1019997007010A KR 19997007010 A KR19997007010 A KR 19997007010A KR 20000070751 A KR20000070751 A KR 20000070751A

Authority

KR

South Korea

Prior art keywords

pyrido

pyrimidin

phenylamino

ethyl

piperidin

Prior art date

1997-02-05

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.)

Ceased

Links

• Espacenet
• Global Dossier
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• 230000004663 cell proliferation Effects 0.000 title claims description 11
• 239000003112 inhibitor Substances 0.000 title abstract description 14
• 150000005007 4-aminopyrimidines Chemical class 0.000 title abstract description 4
• 159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 134
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims abstract description 18
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims abstract description 18
• 201000010099 disease Diseases 0.000 claims abstract description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
• 201000011510 cancer Diseases 0.000 claims abstract description 14
• 239000001257 hydrogen Substances 0.000 claims abstract description 13
• 230000002062 proliferating effect Effects 0.000 claims abstract description 12
• 208000037803 restenosis Diseases 0.000 claims abstract description 11
• 230000001404 mediated effect Effects 0.000 claims abstract description 9
• 239000003085 diluting agent Substances 0.000 claims abstract description 8
• 239000003102 growth factor Substances 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
• 239000003937 drug carrier Substances 0.000 claims abstract description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 5
• -1 2-benzyloxy-ethyl Chemical group 0.000 claims description 139
• 238000000034 method Methods 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 24
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 101150073031 cdk2 gene Proteins 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 14
• 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims description 13
• FWFSAHWQTKFKBC-UHFFFAOYSA-N 8-ethyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound CS(=O)C1=NC=C2C=CC(=O)N(CC)C2=N1 FWFSAHWQTKFKBC-UHFFFAOYSA-N 0.000 claims description 12
• 230000002401 inhibitory effect Effects 0.000 claims description 12
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 11
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 11
• 150000002825 nitriles Chemical class 0.000 claims description 11
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 claims description 10
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 10
• 201000001320 Atherosclerosis Diseases 0.000 claims description 9
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 125000004001 thioalkyl group Chemical group 0.000 claims description 9
• FMZGVQNNAXAUCA-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CCC(C4)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 FMZGVQNNAXAUCA-UHFFFAOYSA-N 0.000 claims description 8
• DLXHWWINPDPYPP-UHFFFAOYSA-N 8-methyl-2-methylsulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound CS(=O)(=O)C1=NC=C2C=CC(=O)N(C)C2=N1 DLXHWWINPDPYPP-UHFFFAOYSA-N 0.000 claims description 8
• 101150012716 CDK1 gene Proteins 0.000 claims description 8
• 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 claims description 8
• 108050007372 Fibroblast Growth Factor Proteins 0.000 claims description 8
• 102000018233 Fibroblast Growth Factor Human genes 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000004494 ethyl ester group Chemical group 0.000 claims description 8
• 229940126864 fibroblast growth factor Drugs 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 150000003573 thiols Chemical class 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical class [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 150000002829 nitrogen Chemical class 0.000 claims description 7
• 239000001301 oxygen Chemical class 0.000 claims description 7
• YNQZITZTUZLNRG-UHFFFAOYSA-N 2-methylsulfinyl-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)NC2=NC(S(=O)C)=NC=C21 YNQZITZTUZLNRG-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 239000011593 sulfur Chemical class 0.000 claims description 6
• 210000004509 vascular smooth muscle cell Anatomy 0.000 claims description 6
• QAWADIWIAIIMDV-UHFFFAOYSA-N 2-anilino-8-(3-bicyclo[2.2.1]heptanyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CCC(C4)C3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 QAWADIWIAIIMDV-UHFFFAOYSA-N 0.000 claims description 5
• BAXBOJGFJVRQAD-UHFFFAOYSA-N 8-ethyl-2-methylsulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound CS(=O)(=O)C1=NC=C2C=CC(=O)N(CC)C2=N1 BAXBOJGFJVRQAD-UHFFFAOYSA-N 0.000 claims description 5
• ZIYCPNXQTFZXCU-UHFFFAOYSA-N 8-ethyl-6-methyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound CS(=O)C1=NC=C2C=C(C)C(=O)N(CC)C2=N1 ZIYCPNXQTFZXCU-UHFFFAOYSA-N 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 101100273808 Xenopus laevis cdk1-b gene Proteins 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• WSZLNFZLFQJSAJ-UHFFFAOYSA-N 2-anilino-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=CC=C1 WSZLNFZLFQJSAJ-UHFFFAOYSA-N 0.000 claims description 4
• MFCJVWFYIKEHSF-UHFFFAOYSA-N 2-methylsulfinyl-8-pentan-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound CS(=O)C1=NC=C2C=CC(=O)N(C(CC)CC)C2=N1 MFCJVWFYIKEHSF-UHFFFAOYSA-N 0.000 claims description 4
• CHKVCVPRHCPVNS-UHFFFAOYSA-N 2-methylsulfinyl-8-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1C1=CC=CC=C1 CHKVCVPRHCPVNS-UHFFFAOYSA-N 0.000 claims description 4
• MQGJNOAVBYXXMD-UHFFFAOYSA-N 2-methylsulfinyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound CS(=O)C1=NC=C2C=CC(=O)N(C(C)C)C2=N1 MQGJNOAVBYXXMD-UHFFFAOYSA-N 0.000 claims description 4
• ARXXWWITFGIXMJ-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CCC(C4)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 ARXXWWITFGIXMJ-UHFFFAOYSA-N 0.000 claims description 4
• GNFJZGMIKIEYET-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CCC(C4)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 GNFJZGMIKIEYET-UHFFFAOYSA-N 0.000 claims description 4
• YBTUXCFDBLSBLC-UHFFFAOYSA-N 8-ethyl-2-(4-hydroxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(O)C=C1 YBTUXCFDBLSBLC-UHFFFAOYSA-N 0.000 claims description 4
• QSPHULVLEFTDKP-UHFFFAOYSA-N 8-ethyl-6-methyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound CSC1=NC=C2C=C(C)C(=O)N(CC)C2=N1 QSPHULVLEFTDKP-UHFFFAOYSA-N 0.000 claims description 4
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• KUZUDTUXRJWJMM-UHFFFAOYSA-N ethyl 3-[2-anilino-4-(ethylamino)pyrimidin-5-yl]prop-2-enoate Chemical compound C1=C(C=CC(=O)OCC)C(NCC)=NC(NC=2C=CC=CC=2)=N1 KUZUDTUXRJWJMM-UHFFFAOYSA-N 0.000 claims description 4
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
• 150000002500 ions Chemical class 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• WZXPIQZXCGAEHP-UHFFFAOYSA-N 2-(benzylamino)-8-cyclohexylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NCC1=CC=CC=C1 WZXPIQZXCGAEHP-UHFFFAOYSA-N 0.000 claims description 3
• YTEPFDOOJDVJID-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-pentan-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(CC)CC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 YTEPFDOOJDVJID-UHFFFAOYSA-N 0.000 claims description 3
• LIGGMHKLMIAZKK-UHFFFAOYSA-N 2-[4-(diethylamino)anilino]-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(N(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2CC)C2=N1 LIGGMHKLMIAZKK-UHFFFAOYSA-N 0.000 claims description 3
• DCPZNPCJNAXVMT-UHFFFAOYSA-N 2-[4-(dimethylamino)anilino]-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(N(C)C)C=C1 DCPZNPCJNAXVMT-UHFFFAOYSA-N 0.000 claims description 3
• WNWKONPFGBOCGT-UHFFFAOYSA-N 2-anilino-8-(cyclohexylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3CCCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 WNWKONPFGBOCGT-UHFFFAOYSA-N 0.000 claims description 3
• ANTXSCKFCYQJLQ-UHFFFAOYSA-N 2-anilino-8-[(4-methoxyphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 ANTXSCKFCYQJLQ-UHFFFAOYSA-N 0.000 claims description 3
• PINSZDSDRFOWQZ-UHFFFAOYSA-N 2-anilino-8-cyclohexylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 PINSZDSDRFOWQZ-UHFFFAOYSA-N 0.000 claims description 3
• OZMNMGRHACMSBT-UHFFFAOYSA-N 2-anilino-8-cyclopentylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 OZMNMGRHACMSBT-UHFFFAOYSA-N 0.000 claims description 3
• UGXSQSZMHDLASV-UHFFFAOYSA-N 2-anilino-8-pentan-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(CC)CC)C2=NC=1NC1=CC=CC=C1 UGXSQSZMHDLASV-UHFFFAOYSA-N 0.000 claims description 3
• MQQAFYHCGPNHAI-UHFFFAOYSA-N 3-[2-anilino-4-(ethylamino)pyrimidin-5-yl]prop-2-enenitrile Chemical compound C1=C(C=CC#N)C(NCC)=NC(NC=2C=CC=CC=2)=N1 MQQAFYHCGPNHAI-UHFFFAOYSA-N 0.000 claims description 3
• BETPKCCUZWUHNW-UHFFFAOYSA-N 6-methyl-2-methylsulfanyl-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(C)C(=O)NC2=NC(SC)=NC=C21 BETPKCCUZWUHNW-UHFFFAOYSA-N 0.000 claims description 3
• DXIFQIGHXFZSGZ-UHFFFAOYSA-N 8-(2-hydroxycyclopentyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound OC1CCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 DXIFQIGHXFZSGZ-UHFFFAOYSA-N 0.000 claims description 3
• OZICFUQNKCVBMB-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-(2-hydroxy-3-morpholin-4-ylpropoxy)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C=C(NC=2N=C3N(C4C5CCC(C5)C4)C(=O)C=CC3=CN=2)C=CC=1OCC(O)CN1CCOCC1 OZICFUQNKCVBMB-UHFFFAOYSA-N 0.000 claims description 3
• BESHJJOBGJYHKG-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-[3-(diethylamino)-2-hydroxypropoxy]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCC(O)CN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4CCC(C4)C3)C2=N1 BESHJJOBGJYHKG-UHFFFAOYSA-N 0.000 claims description 3
• RDRSBBHJJGTEJA-UHFFFAOYSA-N 8-(cyclohexylmethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 RDRSBBHJJGTEJA-UHFFFAOYSA-N 0.000 claims description 3
• HKODLWYAIQGFEZ-UHFFFAOYSA-N 8-cyclohexyl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 HKODLWYAIQGFEZ-UHFFFAOYSA-N 0.000 claims description 3
• WILYEZRGOZWPED-UHFFFAOYSA-N 8-cyclohexyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 WILYEZRGOZWPED-UHFFFAOYSA-N 0.000 claims description 3
• UDTZHILTPAKHBR-UHFFFAOYSA-N 8-cyclopentyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1C1CCCC1 UDTZHILTPAKHBR-UHFFFAOYSA-N 0.000 claims description 3
• GFBSBOHKIQIAPS-UHFFFAOYSA-N 8-ethyl-2-(2-methoxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=CC=C1OC GFBSBOHKIQIAPS-UHFFFAOYSA-N 0.000 claims description 3
• DUOMVERUSWZGIM-UHFFFAOYSA-N 8-ethyl-2-(3-fluoroanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=CC(F)=C1 DUOMVERUSWZGIM-UHFFFAOYSA-N 0.000 claims description 3
• KMUPOOOPAVCTHA-UHFFFAOYSA-N 8-ethyl-2-(4-methoxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(OC)C=C1 KMUPOOOPAVCTHA-UHFFFAOYSA-N 0.000 claims description 3
• FDUVGIYRBPSEDU-UHFFFAOYSA-N 8-ethyl-2-(4-pyrrol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=C1 FDUVGIYRBPSEDU-UHFFFAOYSA-N 0.000 claims description 3
• BMKRSRGITJQCJD-UHFFFAOYSA-N 8-ethyl-2-(pyridin-4-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=NC=C1 BMKRSRGITJQCJD-UHFFFAOYSA-N 0.000 claims description 3
• 206010057469 Vascular stenosis Diseases 0.000 claims description 3
• RXWVQRYZQDBJFA-UHFFFAOYSA-N ethyl 3-(4-amino-2-anilinopyrimidin-5-yl)prop-2-enoate Chemical compound N1=C(N)C(C=CC(=O)OCC)=CN=C1NC1=CC=CC=C1 RXWVQRYZQDBJFA-UHFFFAOYSA-N 0.000 claims description 3
• UZNANWFQLSFUJD-UHFFFAOYSA-N ethyl 3-[2-anilino-4-(ethylamino)pyrimidin-5-yl]but-2-enoate Chemical compound C1=C(C(C)=CC(=O)OCC)C(NCC)=NC(NC=2C=CC=CC=2)=N1 UZNANWFQLSFUJD-UHFFFAOYSA-N 0.000 claims description 3
• QRLNPWIJUJYPRT-UHFFFAOYSA-N ethyl 3-[2-anilino-4-(ethylamino)pyrimidin-5-yl]propanoate Chemical compound C1=C(CCC(=O)OCC)C(NCC)=NC(NC=2C=CC=CC=2)=N1 QRLNPWIJUJYPRT-UHFFFAOYSA-N 0.000 claims description 3
• 230000002980 postoperative effect Effects 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• POKJWRWSUPBDAU-UHFFFAOYSA-N 2-(4-hydroxyanilino)-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C)C2=NC=1NC1=CC=C(O)C=C1 POKJWRWSUPBDAU-UHFFFAOYSA-N 0.000 claims description 2
• GZTMYPPFXKCNDD-UHFFFAOYSA-N 2-(4-methoxyanilino)-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=CC(=O)N2C(C)C)C2=N1 GZTMYPPFXKCNDD-UHFFFAOYSA-N 0.000 claims description 2
• VGAGEGAWKUXMMZ-UHFFFAOYSA-N 2-(benzylamino)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NCC1=CC=CC=C1 VGAGEGAWKUXMMZ-UHFFFAOYSA-N 0.000 claims description 2
• VHYCWKUSTZPDNI-UHFFFAOYSA-N 2-(benzylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C)C2=NC=1NCC1=CC=CC=C1 VHYCWKUSTZPDNI-UHFFFAOYSA-N 0.000 claims description 2
• FFKSWMUEQOUGQI-UHFFFAOYSA-N 2-(butylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)N(C)C2=NC(NCCCC)=NC=C21 FFKSWMUEQOUGQI-UHFFFAOYSA-N 0.000 claims description 2
• ZYRWBFDCUJXOGH-UHFFFAOYSA-N 2-(cyclohexylamino)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1CCCCC1 ZYRWBFDCUJXOGH-UHFFFAOYSA-N 0.000 claims description 2
• DCIHPOIFFJRFKS-UHFFFAOYSA-N 2-(ethylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)N(C)C2=NC(NCC)=NC=C21 DCIHPOIFFJRFKS-UHFFFAOYSA-N 0.000 claims description 2
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• QUHNSFFOKVRSKA-UHFFFAOYSA-N 2-(tert-butylamino)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound CC(C)(C)NC1=NC=C2C=CC(=O)N(CC)C2=N1 QUHNSFFOKVRSKA-UHFFFAOYSA-N 0.000 claims description 2
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• VJIYHBKZMXXTAX-UHFFFAOYSA-N 8-cyclohexyl-2-[4-[2-(diethylamino)ethoxy]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 VJIYHBKZMXXTAX-UHFFFAOYSA-N 0.000 claims description 2
• BRBDHJXRMYPVRR-UHFFFAOYSA-N 8-cyclohexyl-2-[4-[4-(2-hydroxyethyl)-3,5-dimethylpiperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)N(CCO)C(C)CN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 BRBDHJXRMYPVRR-UHFFFAOYSA-N 0.000 claims description 2
• IDOGGIONPJFSSN-UHFFFAOYSA-N 8-cyclohexyl-2-[4-[4-(2-hydroxyethyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(CCO)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 IDOGGIONPJFSSN-UHFFFAOYSA-N 0.000 claims description 2
• QDZSOGUVHXUCBB-UHFFFAOYSA-N 8-cyclohexyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(SC)=NC=C2C=CC(=O)N1C1CCCCC1 QDZSOGUVHXUCBB-UHFFFAOYSA-N 0.000 claims description 2
• LEBREACNBDDHEA-UHFFFAOYSA-N 8-cyclohexyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1C1CCCCC1 LEBREACNBDDHEA-UHFFFAOYSA-N 0.000 claims description 2
• DMZCHFDIDDQVBJ-UHFFFAOYSA-N 8-cyclopentyl-2-(3-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C=CC2=CN=C1NC(C=1)=CC=CC=1N1CCCCC1 DMZCHFDIDDQVBJ-UHFFFAOYSA-N 0.000 claims description 2
• CRHANWDVZFVLRM-UHFFFAOYSA-N 8-cyclopentyl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 CRHANWDVZFVLRM-UHFFFAOYSA-N 0.000 claims description 2
• VHADHMSNFMANQQ-UHFFFAOYSA-N 8-cyclopentyl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 VHADHMSNFMANQQ-UHFFFAOYSA-N 0.000 claims description 2
• WYLARAIZFZOWSV-UHFFFAOYSA-N 8-cyclopentyl-2-(4-pyrrol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=C1 WYLARAIZFZOWSV-UHFFFAOYSA-N 0.000 claims description 2
• VWMWCXNMNMKIHD-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(3-hydroxypiperidin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(O)CCCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCC3)C2=N1 VWMWCXNMNMKIHD-UHFFFAOYSA-N 0.000 claims description 2
• RDMCVRMSSBDOPT-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(4-hydroxypiperidin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCC3)C2=N1 RDMCVRMSSBDOPT-UHFFFAOYSA-N 0.000 claims description 2
• FUBDWXAVMGEMPP-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCC3)C2=N1 FUBDWXAVMGEMPP-UHFFFAOYSA-N 0.000 claims description 2
• YYZJJQLIOBCYAE-UHFFFAOYSA-N 8-cyclopentyl-2-[4-[2-(diethylamino)ethoxy]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCC3)C2=N1 YYZJJQLIOBCYAE-UHFFFAOYSA-N 0.000 claims description 2
• NHFOJLXSGIRMHT-UHFFFAOYSA-N 8-cyclopentyl-2-[4-[2-(hydroxymethyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound OCC1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCC3)C2=N1 NHFOJLXSGIRMHT-UHFFFAOYSA-N 0.000 claims description 2
• GADHEEGKFLBSNG-UHFFFAOYSA-N 8-cyclopentyl-2-[4-[4-(2-hydroxyethyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(CCO)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCC3)C2=N1 GADHEEGKFLBSNG-UHFFFAOYSA-N 0.000 claims description 2
• XMFLYAAMACXUHD-UHFFFAOYSA-N 8-cyclopentyl-2-[4-[4-(3-hydroxypropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(CCCO)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCC3)C2=N1 XMFLYAAMACXUHD-UHFFFAOYSA-N 0.000 claims description 2
• REDXWYHSSILFOH-UHFFFAOYSA-N 8-cyclopropyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CC3)C2=N1 REDXWYHSSILFOH-UHFFFAOYSA-N 0.000 claims description 2
• ZIFXRDYNARAMOB-UHFFFAOYSA-N 8-cyclopropyl-2-[4-[2-(diethylamino)ethoxy]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2C3CC3)C2=N1 ZIFXRDYNARAMOB-UHFFFAOYSA-N 0.000 claims description 2
• VVCSVLSWGRTAJV-UHFFFAOYSA-N 8-cyclopropyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(SC)=NC=C2C=CC(=O)N1C1CC1 VVCSVLSWGRTAJV-UHFFFAOYSA-N 0.000 claims description 2
• YYFZSNXQDUUXQC-UHFFFAOYSA-N 8-cyclopropyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1C1CC1 YYFZSNXQDUUXQC-UHFFFAOYSA-N 0.000 claims description 2
• ANNBTYAXGUXJAV-UHFFFAOYSA-N 8-ethyl-2-(2-phenylmethoxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=CC=C1OCC1=CC=CC=C1 ANNBTYAXGUXJAV-UHFFFAOYSA-N 0.000 claims description 2
• NONLSGITGWURTI-UHFFFAOYSA-N 8-ethyl-2-(3-fluoro-2-methoxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=CC(F)=C1OC NONLSGITGWURTI-UHFFFAOYSA-N 0.000 claims description 2
• IKVTYYLJFREDBA-UHFFFAOYSA-N 8-ethyl-2-(3-fluoro-4-methoxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(OC)C(F)=C1 IKVTYYLJFREDBA-UHFFFAOYSA-N 0.000 claims description 2
• DXMBSYMFSSVIKY-UHFFFAOYSA-N 8-ethyl-2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(F)C=C1 DXMBSYMFSSVIKY-UHFFFAOYSA-N 0.000 claims description 2
• PXTOVJWQCDYWEC-UHFFFAOYSA-N 8-ethyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N1CCOCC1 PXTOVJWQCDYWEC-UHFFFAOYSA-N 0.000 claims description 2
• FPSHLCLHIBFSNA-UHFFFAOYSA-N 8-ethyl-2-(4-phenylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1C1=CC=CC=C1 FPSHLCLHIBFSNA-UHFFFAOYSA-N 0.000 claims description 2
• PZIGHMJLTJTNDH-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)N(CC)C2=NC(NCC)=NC=C21 PZIGHMJLTJTNDH-UHFFFAOYSA-N 0.000 claims description 2
• VEFZKTGTIAMKDL-UHFFFAOYSA-N 8-ethyl-2-(propan-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC(C)NC1=NC=C2C=CC(=O)N(CC)C2=N1 VEFZKTGTIAMKDL-UHFFFAOYSA-N 0.000 claims description 2
• IIFSTQQBGVASBN-UHFFFAOYSA-N 8-ethyl-2-[3-(1,1,2,2-tetrafluoroethoxy)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=CC(OC(F)(F)C(F)F)=C1 IIFSTQQBGVASBN-UHFFFAOYSA-N 0.000 claims description 2
• MQTLLTKZDOQNDH-UHFFFAOYSA-N 8-ethyl-2-[4-(2-methoxyethoxy)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(OCCOC)C=C1 MQTLLTKZDOQNDH-UHFFFAOYSA-N 0.000 claims description 2
• BUNLBUQVVVGGJD-UHFFFAOYSA-N 8-ethyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 BUNLBUQVVVGGJD-UHFFFAOYSA-N 0.000 claims description 2
• SRPLXACXDNOTML-UHFFFAOYSA-N 8-ethyl-6-methyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C)C(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 SRPLXACXDNOTML-UHFFFAOYSA-N 0.000 claims description 2
• ZSWFNWHZWAZHAZ-UHFFFAOYSA-N 8-methyl-2-(2-pyridin-2-ylethylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C)C2=NC=1NCCC1=CC=CC=N1 ZSWFNWHZWAZHAZ-UHFFFAOYSA-N 0.000 claims description 2
• BJITXHXIUDICHG-UHFFFAOYSA-N 8-methyl-2-(propan-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)N(C)C2=NC(NC(C)C)=NC=C21 BJITXHXIUDICHG-UHFFFAOYSA-N 0.000 claims description 2
• MNSISNKKBAWEKI-UHFFFAOYSA-N CCOC(=O)C=Cc1cnc(SC)nc1NC1CCN(CC1)C(=O)OCC Chemical compound CCOC(=O)C=Cc1cnc(SC)nc1NC1CCN(CC1)C(=O)OCC MNSISNKKBAWEKI-UHFFFAOYSA-N 0.000 claims description 2
• MSDHSYRDIUNQBH-UHFFFAOYSA-N ethyl 3-[4-(cyclohexylamino)-2-methylsulfanylpyrimidin-5-yl]prop-2-enoate Chemical compound CCOC(=O)C=CC1=CN=C(SC)N=C1NC1CCCCC1 MSDHSYRDIUNQBH-UHFFFAOYSA-N 0.000 claims description 2
• YIQXWTAVJPSUKJ-UHFFFAOYSA-N ethyl 3-[4-(cyclopropylamino)-2-methylsulfanylpyrimidin-5-yl]prop-2-enoate Chemical compound CCOC(=O)C=CC1=CN=C(SC)N=C1NC1CC1 YIQXWTAVJPSUKJ-UHFFFAOYSA-N 0.000 claims description 2
• JTOUZZGATLMRIK-UHFFFAOYSA-N ethyl 4-(2-methylsulfinyl-7-oxopyrido[2,3-d]pyrimidin-8-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1C(=O)C=CC2=CN=C(S(C)=O)N=C21 JTOUZZGATLMRIK-UHFFFAOYSA-N 0.000 claims description 2
• VLXMQIWGAQUDQA-UHFFFAOYSA-N methyl 2-(2-anilino-7-oxopyrido[2,3-d]pyrimidin-8-yl)acetate Chemical compound N=1C=C2C=CC(=O)N(CC(=O)OC)C2=NC=1NC1=CC=CC=C1 VLXMQIWGAQUDQA-UHFFFAOYSA-N 0.000 claims description 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
• YUJYTRXVUHGEGP-UHFFFAOYSA-N 8-(3-hydroxypropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCCO)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 YUJYTRXVUHGEGP-UHFFFAOYSA-N 0.000 claims 2
• YHTJUZNIOKOAMP-UHFFFAOYSA-N 2-(2,3-dihydro-1h-indol-6-ylamino)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C2CCNC2=CC(NC=2N=C3N(C(C=CC3=CN=2)=O)CC)=C1 YHTJUZNIOKOAMP-UHFFFAOYSA-N 0.000 claims 1
• SVJNWILXZCNIRZ-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(OC)C(OC)=C1 SVJNWILXZCNIRZ-UHFFFAOYSA-N 0.000 claims 1
• LVRJGFFEEFKTKE-UHFFFAOYSA-N 2-[(2,3-diphenylquinoxalin-6-yl)amino]-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC(C=C1N=C2C=3C=CC=CC=3)=CC=C1N=C2C1=CC=CC=C1 LVRJGFFEEFKTKE-UHFFFAOYSA-N 0.000 claims 1
• SNJHMWULDFCDMV-UHFFFAOYSA-N 2-[3-(1h-benzimidazol-2-yl)anilino]-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC=C2NC(C=3C=CC=C(C=3)NC=3N=C4N(C(C=CC4=CN=3)=O)CC)=NC2=C1 SNJHMWULDFCDMV-UHFFFAOYSA-N 0.000 claims 1
• KGXSRVAIZHYXAN-UHFFFAOYSA-N 2-[4-(1h-benzimidazol-2-yl)anilino]-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC=C2NC(C3=CC=C(C=C3)NC=3N=C4N(C(C=CC4=CN=3)=O)CC)=NC2=C1 KGXSRVAIZHYXAN-UHFFFAOYSA-N 0.000 claims 1
• KHMOGXJVRYQASK-UHFFFAOYSA-N 2-[4-(2,3-dihydroxypropoxy)anilino]-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(OCC(O)CO)C=C1 KHMOGXJVRYQASK-UHFFFAOYSA-N 0.000 claims 1
• HRZBOOIXUDRYDZ-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(3-phenylmethoxypropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CCCOCC=3C=CC=CC=3)C2=N1 HRZBOOIXUDRYDZ-UHFFFAOYSA-N 0.000 claims 1
• NPVBCNNKDMRCSF-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-8-(3-phenylmethoxypropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2CCCOCC=3C=CC=CC=3)C2=N1 NPVBCNNKDMRCSF-UHFFFAOYSA-N 0.000 claims 1
• UNNXSBACNGVTRW-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethylamino]anilino]-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(NCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2CC)C2=N1 UNNXSBACNGVTRW-UHFFFAOYSA-N 0.000 claims 1
• GSJSCQNLBVBVPG-UHFFFAOYSA-N 3-[(8-ethyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]-n,n-dimethylbenzamide Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=CC(C(=O)N(C)C)=C1 GSJSCQNLBVBVPG-UHFFFAOYSA-N 0.000 claims 1
• ODOWJBZJSVDJGL-UHFFFAOYSA-N 3-n'-[4-[2-[4-[(8-ethyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]phenoxy]ethoxy]phenyl]propanediimidamide Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1OCCOC1=CC=C(NC(=N)CC(N)=N)C=C1 ODOWJBZJSVDJGL-UHFFFAOYSA-N 0.000 claims 1
• BHZVVYMLGXBOFG-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[3-(1,1,2,2-tetrafluoroethoxy)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound FC(F)C(F)(F)OC1=CC=CC(NC=2N=C3N(C4C5CCC(C5)C4)C(=O)C=CC3=CN=2)=C1 BHZVVYMLGXBOFG-UHFFFAOYSA-N 0.000 claims 1
• DHOSGLXAUZKCBJ-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-[2-(diethylamino)ethoxy]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4CCC(C4)C3)C2=N1 DHOSGLXAUZKCBJ-UHFFFAOYSA-N 0.000 claims 1
• PUURRQSCNPWFKC-UHFFFAOYSA-N 8-(3-hydroxypropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one;dihydrochloride Chemical compound Cl.Cl.N=1C=C2C=CC(=O)N(CCCO)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 PUURRQSCNPWFKC-UHFFFAOYSA-N 0.000 claims 1
• RQUBDOBSPYGIAS-UHFFFAOYSA-N 8-(3-phenylmethoxypropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCCOCC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 RQUBDOBSPYGIAS-UHFFFAOYSA-N 0.000 claims 1
• DIFKCOBOSFUEIW-UHFFFAOYSA-N 8-cycloheptyl-2-[4-[2-(diethylamino)ethoxy]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCCC3)C2=N1 DIFKCOBOSFUEIW-UHFFFAOYSA-N 0.000 claims 1
• WERMOQTXESCLAB-UHFFFAOYSA-N 8-cyclohexyl-2-[4-(3,5-dimethylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)NC(C)CN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 WERMOQTXESCLAB-UHFFFAOYSA-N 0.000 claims 1
• ZJMZEJRLZIPMQD-UHFFFAOYSA-N 8-cyclohexyl-2-[4-(4-methylpiperidin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 ZJMZEJRLZIPMQD-UHFFFAOYSA-N 0.000 claims 1
• CHWSJBTZEFFJKG-UHFFFAOYSA-N 8-cyclohexyl-2-[4-[3-(hydroxymethyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(CO)CCCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 CHWSJBTZEFFJKG-UHFFFAOYSA-N 0.000 claims 1
• XSZNRJAHWBJGJL-UHFFFAOYSA-N 8-cyclohexyl-2-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CCCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 XSZNRJAHWBJGJL-UHFFFAOYSA-N 0.000 claims 1
• FGNUGGYSFOYPHJ-UHFFFAOYSA-N 8-ethyl-2-(1h-indazol-6-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C2C=NNC2=CC(NC=2N=C3N(C(C=CC3=CN=2)=O)CC)=C1 FGNUGGYSFOYPHJ-UHFFFAOYSA-N 0.000 claims 1
• AGARYQWTQSNGDZ-UHFFFAOYSA-N 8-ethyl-2-(1h-indol-6-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C2C=CNC2=CC(NC=2N=C3N(C(C=CC3=CN=2)=O)CC)=C1 AGARYQWTQSNGDZ-UHFFFAOYSA-N 0.000 claims 1
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