KR20000070751A - 세포 증식 억제제로서의 피리도[2,3-ｄ]피리미딘 및 4-아미노피리미딘 - Google Patents
세포 증식 억제제로서의 피리도[2,3-ｄ]피리미딘 및 4-아미노피리미딘 Download PDFInfo
- 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
- 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
- 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
- CYIQWPZMTPNAFQ-UHFFFAOYSA-N 2-(ethylamino)-8-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NCC)=NC=C2C=CC(=O)N1C1=CC=CC=C1 CYIQWPZMTPNAFQ-UHFFFAOYSA-N 0.000 claims description 2
- 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
- FLJCNJTYQITNIA-UHFFFAOYSA-N 2-[4-(2-morpholin-4-ylethoxy)anilino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1OCCN1CCOCC1 FLJCNJTYQITNIA-UHFFFAOYSA-N 0.000 claims description 2
- GKQSKZCNRVZXNQ-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2-phenylmethoxyethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CCOCC=3C=CC=CC=3)C2=N1 GKQSKZCNRVZXNQ-UHFFFAOYSA-N 0.000 claims description 2
- JKAYQOHHGOZXJH-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C=3C=CC=CC=3)C2=N1 JKAYQOHHGOZXJH-UHFFFAOYSA-N 0.000 claims description 2
- FZMILJWYZFDXTP-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 FZMILJWYZFDXTP-UHFFFAOYSA-N 0.000 claims description 2
- JKGXCSGVMHNLHY-UHFFFAOYSA-N 2-[4-(dimethylamino)anilino]-8-(3-phenylmethoxypropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC=C(C=CC(=O)N2CCCOCC=3C=CC=CC=3)C2=N1 JKGXCSGVMHNLHY-UHFFFAOYSA-N 0.000 claims description 2
- CGSGRPKQMNSXLU-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-8-[3-(oxan-2-yloxy)propyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2CCCOC3OCCCC3)C2=N1 CGSGRPKQMNSXLU-UHFFFAOYSA-N 0.000 claims description 2
- QIQYKWBRXRSSNC-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2CC)C2=N1 QIQYKWBRXRSSNC-UHFFFAOYSA-N 0.000 claims description 2
- QRLYOXMIPWTXIA-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2C(C)C)C2=N1 QRLYOXMIPWTXIA-UHFFFAOYSA-N 0.000 claims description 2
- SHFNDPYHFKYJEH-UHFFFAOYSA-N 2-amino-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound NC1=NC=C2C=CC(=O)N(C)C2=N1 SHFNDPYHFKYJEH-UHFFFAOYSA-N 0.000 claims description 2
- WSYNWKIFVKWJSA-UHFFFAOYSA-N 2-anilino-8-(2-methoxyethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOC)C2=NC=1NC1=CC=CC=C1 WSYNWKIFVKWJSA-UHFFFAOYSA-N 0.000 claims description 2
- KEQUTRUTNCWETK-UHFFFAOYSA-N 2-anilino-8-(2-methylpropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(C)C)C2=NC=1NC1=CC=CC=C1 KEQUTRUTNCWETK-UHFFFAOYSA-N 0.000 claims description 2
- UHMYQAWCVQUHIQ-UHFFFAOYSA-N 2-anilino-8-(3-phenoxypropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCCOC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 UHMYQAWCVQUHIQ-UHFFFAOYSA-N 0.000 claims description 2
- NXZUXHFIPIDFCD-UHFFFAOYSA-N 2-anilino-8-(3-phenylmethoxypropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCCOCC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 NXZUXHFIPIDFCD-UHFFFAOYSA-N 0.000 claims description 2
- QBBAIJFXDFLCKG-UHFFFAOYSA-N 2-anilino-8-(methoxymethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(COC)C2=NC=1NC1=CC=CC=C1 QBBAIJFXDFLCKG-UHFFFAOYSA-N 0.000 claims description 2
- MHZCBYNKWGSPEP-UHFFFAOYSA-N 2-anilino-8-benzylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 MHZCBYNKWGSPEP-UHFFFAOYSA-N 0.000 claims description 2
- JKLHWLBKGBOQKG-UHFFFAOYSA-N 2-anilino-8-butan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CC)C2=NC=1NC1=CC=CC=C1 JKLHWLBKGBOQKG-UHFFFAOYSA-N 0.000 claims description 2
- ZEHXSPZMRLUPSR-UHFFFAOYSA-N 2-anilino-8-butylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCCC)C2=NC=1NC1=CC=CC=C1 ZEHXSPZMRLUPSR-UHFFFAOYSA-N 0.000 claims description 2
- RTUNPZNLBHLEDM-UHFFFAOYSA-N 2-anilino-8-cycloheptylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 RTUNPZNLBHLEDM-UHFFFAOYSA-N 0.000 claims description 2
- ITVLJAYGNKIPTH-UHFFFAOYSA-N 2-anilino-8-cyclopropylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 ITVLJAYGNKIPTH-UHFFFAOYSA-N 0.000 claims description 2
- MULWPIYHXLTYII-UHFFFAOYSA-N 2-anilino-8-ethyl-6-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 MULWPIYHXLTYII-UHFFFAOYSA-N 0.000 claims description 2
- OFBWCQATNOQYNA-UHFFFAOYSA-N 2-anilino-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C)C2=NC=1NC1=CC=CC=C1 OFBWCQATNOQYNA-UHFFFAOYSA-N 0.000 claims description 2
- OXTHRQJHLPWQTD-UHFFFAOYSA-N 2-anilino-8-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 OXTHRQJHLPWQTD-UHFFFAOYSA-N 0.000 claims description 2
- JNPPLTSTJPYKOL-UHFFFAOYSA-N 2-anilino-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=CC=C1 JNPPLTSTJPYKOL-UHFFFAOYSA-N 0.000 claims description 2
- ZEJXJYCOUVOWGJ-UHFFFAOYSA-N 2-anilino-8-propylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCC)C2=NC=1NC1=CC=CC=C1 ZEJXJYCOUVOWGJ-UHFFFAOYSA-N 0.000 claims description 2
- XYNTUVYBWMEVMB-UHFFFAOYSA-N 2-methylsulfinyl-8-(2-phenylmethoxyethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1CCOCC1=CC=CC=C1 XYNTUVYBWMEVMB-UHFFFAOYSA-N 0.000 claims description 2
- SWYYEZWIFXEMQI-UHFFFAOYSA-N 2-methylsulfonyl-8-[3-(oxan-2-yloxy)propyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)(=O)C)=NC=C2C=CC(=O)N1CCCOC1CCCCO1 SWYYEZWIFXEMQI-UHFFFAOYSA-N 0.000 claims description 2
- BCUGWOJVEDGGSV-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4CCC(C4)C3)C2=N1 BCUGWOJVEDGGSV-UHFFFAOYSA-N 0.000 claims description 2
- FBXSNCGYVKXHOB-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-(4-phenylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CCC(C4)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1C1=CC=CC=C1 FBXSNCGYVKXHOB-UHFFFAOYSA-N 0.000 claims description 2
- GEOFPYCFSMWTOR-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-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)N2C3C4CCC(C4)C3)C2=N1 GEOFPYCFSMWTOR-UHFFFAOYSA-N 0.000 claims description 2
- RJSUJPRFFXGRHX-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-(trifluoromethylsulfanyl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(SC(F)(F)F)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4CCC(C4)C3)C2=N1 RJSUJPRFFXGRHX-UHFFFAOYSA-N 0.000 claims description 2
- XWFXTZJEPJPOIQ-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-[3-(3-hydroxypropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(CCCO)CCCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4CCC(C4)C3)C2=N1 XWFXTZJEPJPOIQ-UHFFFAOYSA-N 0.000 claims description 2
- JMIAADRNDQXFLO-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-[3-(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(C1)CCCC1CCCN1CCOCC1 JMIAADRNDQXFLO-UHFFFAOYSA-N 0.000 claims description 2
- GFGIEGFCJCUJDE-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-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)N2C3C4CCC(C4)C3)C2=N1 GFGIEGFCJCUJDE-UHFFFAOYSA-N 0.000 claims description 2
- AUKHIOSAPSJPSC-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-[3-(morpholin-4-ylmethyl)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(C1)CCCC1CN1CCOCC1 AUKHIOSAPSJPSC-UHFFFAOYSA-N 0.000 claims description 2
- BQFQHTAIMBUUGD-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-[4-(2-morpholin-4-ylethyl)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)CCC1CCN1CCOCC1 BQFQHTAIMBUUGD-UHFFFAOYSA-N 0.000 claims description 2
- PETCVZZPKYJZAU-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-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)N2C3C4CCC(C4)C3)C2=N1 PETCVZZPKYJZAU-UHFFFAOYSA-N 0.000 claims description 2
- XLYNELMBEAWPLE-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-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)N2C3C4CCC(C4)C3)C2=N1 XLYNELMBEAWPLE-UHFFFAOYSA-N 0.000 claims description 2
- XETUUHPJZYXUBY-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(SC)=NC=C2C=CC(=O)N1C1C(C2)CCC2C1 XETUUHPJZYXUBY-UHFFFAOYSA-N 0.000 claims description 2
- GXEHZEIVHVQOFI-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1C1C(C2)CCC2C1 GXEHZEIVHVQOFI-UHFFFAOYSA-N 0.000 claims description 2
- BAOFQYGZXFLQJL-UHFFFAOYSA-N 8-(cyclohexylmethyl)-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1CC1CCCCC1 BAOFQYGZXFLQJL-UHFFFAOYSA-N 0.000 claims description 2
- RVHDGMZLUMBUTO-UHFFFAOYSA-N 8-(oxolan-3-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3COCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 RVHDGMZLUMBUTO-UHFFFAOYSA-N 0.000 claims description 2
- OHAZQCPORIOWPF-UHFFFAOYSA-N 8-[2,2-dimethyl-3-(oxan-2-yloxy)propyl]-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(SC)=NC=C2C=CC(=O)N1CC(C)(C)COC1CCCCO1 OHAZQCPORIOWPF-UHFFFAOYSA-N 0.000 claims description 2
- BPCHFYRJWFWWTC-UHFFFAOYSA-N 8-[3-(oxan-2-yloxy)propyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCCOC3OCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 BPCHFYRJWFWWTC-UHFFFAOYSA-N 0.000 claims description 2
- VORACZSARJDQPL-UHFFFAOYSA-N 8-cycloheptyl-2-(3-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCCC3)C(=O)C=CC2=CN=C1NC(C=1)=CC=CC=1N1CCCCC1 VORACZSARJDQPL-UHFFFAOYSA-N 0.000 claims description 2
- SVDPYMUUCNTPSO-UHFFFAOYSA-N 8-cycloheptyl-2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCCC3)C2=N1 SVDPYMUUCNTPSO-UHFFFAOYSA-N 0.000 claims description 2
- UGFKFRBAWCZWGF-UHFFFAOYSA-N 8-cycloheptyl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 UGFKFRBAWCZWGF-UHFFFAOYSA-N 0.000 claims description 2
- GQSKTTPNRLSULS-UHFFFAOYSA-N 8-cycloheptyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(SC)=NC=C2C=CC(=O)N1C1CCCCCC1 GQSKTTPNRLSULS-UHFFFAOYSA-N 0.000 claims description 2
- QLOHCKZNTYPYGA-UHFFFAOYSA-N 8-cycloheptyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1C1CCCCCC1 QLOHCKZNTYPYGA-UHFFFAOYSA-N 0.000 claims description 2
- WKMJMDSBBMIPAY-UHFFFAOYSA-N 8-cyclohexyl-2-(2-piperidin-1-ylethylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NCCN1CCCCC1 WKMJMDSBBMIPAY-UHFFFAOYSA-N 0.000 claims description 2
- LFPMZGAREDDJMI-UHFFFAOYSA-N 8-cyclohexyl-2-(3-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=1)=CC=CC=1N1CCCCC1 LFPMZGAREDDJMI-UHFFFAOYSA-N 0.000 claims description 2
- MWDWQLRXDKQXBE-UHFFFAOYSA-N 8-cyclohexyl-2-(3-piperidin-1-ylpropylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NCCCN1CCCCC1 MWDWQLRXDKQXBE-UHFFFAOYSA-N 0.000 claims description 2
- XUBOSXKNLKMAQP-UHFFFAOYSA-N 8-cyclohexyl-2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 XUBOSXKNLKMAQP-UHFFFAOYSA-N 0.000 claims description 2
- DXDINYSNEVNZKU-UHFFFAOYSA-N 8-cyclohexyl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 DXDINYSNEVNZKU-UHFFFAOYSA-N 0.000 claims description 2
- KGWFRLAKNCTOLV-UHFFFAOYSA-N 8-cyclohexyl-2-(4-pyrrol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=C1 KGWFRLAKNCTOLV-UHFFFAOYSA-N 0.000 claims description 2
- IOSIDCRATLJCCR-UHFFFAOYSA-N 8-cyclohexyl-2-(4-pyrrolidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCC1 IOSIDCRATLJCCR-UHFFFAOYSA-N 0.000 claims description 2
- SFSHWGQPROTPJI-UHFFFAOYSA-N 8-cyclohexyl-2-(4-thiomorpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCSCC1 SFSHWGQPROTPJI-UHFFFAOYSA-N 0.000 claims description 2
- BFMAYWQMWYRCBV-UHFFFAOYSA-N 8-cyclohexyl-2-(cyclohexylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC1CCCCC1 BFMAYWQMWYRCBV-UHFFFAOYSA-N 0.000 claims description 2
- VKXFQYQSYVNPAT-UHFFFAOYSA-N 8-cyclohexyl-2-[(4-methoxyphenyl)methylamino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1CNC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 VKXFQYQSYVNPAT-UHFFFAOYSA-N 0.000 claims description 2
- UNXVNIREDYMNAN-UHFFFAOYSA-N 8-cyclohexyl-2-[4-(3,4-dihydro-1h-isoquinolin-2-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C=CC2=CN=C(NC=3C=CC(=CC=3)N3CC4=CC=CC=C4CC3)N=C2N1C1CCCCC1 UNXVNIREDYMNAN-UHFFFAOYSA-N 0.000 claims description 2
- KNBGMDSMIRJYHC-UHFFFAOYSA-N 8-cyclohexyl-2-[4-(3,5-dimethylpiperidin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CC(C)CN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 KNBGMDSMIRJYHC-UHFFFAOYSA-N 0.000 claims description 2
- KMMPKROFDZEGKS-UHFFFAOYSA-N 8-cyclohexyl-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)N2C3CCCCC3)C2=N1 KMMPKROFDZEGKS-UHFFFAOYSA-N 0.000 claims description 2
- MNMBOOPVISUASS-UHFFFAOYSA-N 8-cyclohexyl-2-[4-(dimethylamino)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 MNMBOOPVISUASS-UHFFFAOYSA-N 0.000 claims description 2
- SUHNCVSSYLYOLU-UHFFFAOYSA-N 8-cyclohexyl-2-[4-[2-(diethylamino)ethoxy]-3-methylanilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(C)C(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 SUHNCVSSYLYOLU-UHFFFAOYSA-N 0.000 claims description 2
- 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
- FHINTLXPUAAKTH-UHFFFAOYSA-N 8-ethyl-2-(4-hydroxy-3-methoxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(O)C(OC)=C1 FHINTLXPUAAKTH-UHFFFAOYSA-N 0.000 claims 1
- JVHNWOMNQMBCJH-UHFFFAOYSA-N 8-ethyl-2-(4-pyridin-3-yloxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1OC1=CC=CN=C1 JVHNWOMNQMBCJH-UHFFFAOYSA-N 0.000 claims 1
- BUPFZBKCFFMASH-UHFFFAOYSA-N 8-ethyl-2-(9h-fluoren-3-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC=C2C3=CC(NC=4N=C5N(C(C=CC5=CN=4)=O)CC)=CC=C3CC2=C1 BUPFZBKCFFMASH-UHFFFAOYSA-N 0.000 claims 1
- NMOCRVBIAVFQHU-UHFFFAOYSA-N 8-ethyl-2-[4-(4-methylpiperidine-1-carbonyl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1C(=O)N1CCC(C)CC1 NMOCRVBIAVFQHU-UHFFFAOYSA-N 0.000 claims 1
- KJTFMZWWZFPORY-UHFFFAOYSA-N n-[1-[4-[(8-ethyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]phenyl]-1,3-dihydroxypropan-2-yl]acetamide Chemical compound N=1C=C2C=CC(=O)N(CC)C2=NC=1NC1=CC=C(C(O)C(CO)NC(C)=O)C=C1 KJTFMZWWZFPORY-UHFFFAOYSA-N 0.000 claims 1
- 108091007914 CDKs Proteins 0.000 abstract description 11
- 108091000080 Phosphotransferase Proteins 0.000 abstract description 10
- 102000020233 phosphotransferase Human genes 0.000 abstract description 10
- 230000003389 potentiating effect Effects 0.000 abstract description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 150000008518 pyridopyrimidines Chemical class 0.000 abstract description 3
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 634
- 238000002844 melting Methods 0.000 description 242
- 230000008018 melting Effects 0.000 description 242
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 221
- 235000019439 ethyl acetate Nutrition 0.000 description 211
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 110
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 110
- 239000000243 solution Substances 0.000 description 107
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
- 230000002829 reductive effect Effects 0.000 description 84
- 239000007787 solid Substances 0.000 description 80
- 239000003480 eluent Substances 0.000 description 70
- 238000003818 flash chromatography Methods 0.000 description 70
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 239000011541 reaction mixture Substances 0.000 description 66
- 239000000203 mixture Substances 0.000 description 64
- 239000012044 organic layer Substances 0.000 description 56
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 55
- 235000019341 magnesium sulphate Nutrition 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 44
- 239000000725 suspension Substances 0.000 description 42
- 238000001914 filtration Methods 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000000047 product Substances 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 238000010992 reflux Methods 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000012267 brine Substances 0.000 description 27
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 27
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 25
- 229910000104 sodium hydride Inorganic materials 0.000 description 24
- 239000003921 oil Substances 0.000 description 22
- 150000001412 amines Chemical class 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 238000000746 purification Methods 0.000 description 16
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 238000003556 assay Methods 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 239000000395 magnesium oxide Substances 0.000 description 10
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000003826 tablet Substances 0.000 description 10
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
- 235000018102 proteins Nutrition 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- JWEMWYPUAVAOBO-UHFFFAOYSA-N 2-anilino-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2NC(=O)C=CC2=CN=C1NC1=CC=CC=C1 JWEMWYPUAVAOBO-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- SNNHLSHDDGJVDM-UHFFFAOYSA-N ethyl 4-chloro-2-methylsulfanylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SC)N=C1Cl SNNHLSHDDGJVDM-UHFFFAOYSA-N 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- FLVDHJYGUBRAHX-UHFFFAOYSA-N 2-anilino-4-(ethylamino)pyrimidine-5-carbaldehyde Chemical compound C1=C(C=O)C(NCC)=NC(NC=2C=CC=CC=2)=N1 FLVDHJYGUBRAHX-UHFFFAOYSA-N 0.000 description 5
- QLXQZMXJCYIIGS-UHFFFAOYSA-N C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1 Chemical compound C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O1CCCC1 QLXQZMXJCYIIGS-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 102000001332 SRC Human genes 0.000 description 5
- 108060006706 SRC Proteins 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 230000022131 cell cycle Effects 0.000 description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 5
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 4
- WGUCZWYLSKPURM-UHFFFAOYSA-N 4-(methylamino)-2-methylsulfanylpyrimidine-5-carbaldehyde Chemical compound CNC1=NC(SC)=NC=C1C=O WGUCZWYLSKPURM-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000013592 cell lysate Substances 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 125000005394 methallyl group Chemical group 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000035755 proliferation Effects 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 4
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 3
- KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 3
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 206010006187 Breast cancer Diseases 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- 102000016736 Cyclin Human genes 0.000 description 3
- 108050006400 Cyclin Proteins 0.000 description 3
- 102000001301 EGF receptor Human genes 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- AIGLEQLWQODLLF-UHFFFAOYSA-N [2-anilino-4-(ethylamino)pyrimidin-5-yl]methanol Chemical compound C1=C(CO)C(NCC)=NC(NC=2C=CC=CC=2)=N1 AIGLEQLWQODLLF-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical class CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004581 coalescence Methods 0.000 description 3
- 235000011180 diphosphates Nutrition 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 201000005202 lung cancer Diseases 0.000 description 3
- 208000020816 lung neoplasm Diseases 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 108091005981 phosphorylated proteins Proteins 0.000 description 3
- 230000036470 plasma concentration Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 3
- 229940048086 sodium pyrophosphate Drugs 0.000 description 3
- 239000007909 solid dosage form Substances 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 3
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- GIGZSBMZFYEGDE-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1(C)C(C2)CCC1(C)C2N(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1CCCCC1 GIGZSBMZFYEGDE-UHFFFAOYSA-N 0.000 description 2
- OYDOIWJQPNYODH-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1(C)C(C2)CCC1(C)C2N(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1C=CC=N1 OYDOIWJQPNYODH-UHFFFAOYSA-N 0.000 description 2
- MKHGVMIXRPGHOO-UHFFFAOYSA-N 2-(benzenesulfonyl)-3-phenyloxaziridine Chemical compound C=1C=CC=CC=1S(=O)(=O)N1OC1C1=CC=CC=C1 MKHGVMIXRPGHOO-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- OGLKRGJCAQTSQP-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(1-naphthalen-2-ylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)N(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1CCN(C)CC1 OGLKRGJCAQTSQP-UHFFFAOYSA-N 0.000 description 2
- JOZLHPXQBRYZIO-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(1-phenylpropan-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(C)CC1=CC=CC=C1 JOZLHPXQBRYZIO-UHFFFAOYSA-N 0.000 description 2
- DTENHCCQQDNHKJ-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-[(4-methylsulfanylphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(SC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 DTENHCCQQDNHKJ-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- GJHSMEXUTGBCPQ-UHFFFAOYSA-N 2-anilino-8-(1-naphthalen-2-ylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)N(C(C=CC1=CN=2)=O)C1=NC=2NC1=CC=CC=C1 GJHSMEXUTGBCPQ-UHFFFAOYSA-N 0.000 description 2
- ACPLTHSENFFEFZ-UHFFFAOYSA-N 2-anilino-8-(1-phenylpropan-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C)CC1=CC=CC=C1 ACPLTHSENFFEFZ-UHFFFAOYSA-N 0.000 description 2
- INROJOXIIQTECZ-UHFFFAOYSA-N 2-anilino-8-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1(C)C(C2)CCC1(C)C2N(C(C=CC1=CN=2)=O)C1=NC=2NC1=CC=CC=C1 INROJOXIIQTECZ-UHFFFAOYSA-N 0.000 description 2
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 2
- BHIZVZJETFVJMJ-UHFFFAOYSA-N 2-hydroxypropyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)O BHIZVZJETFVJMJ-UHFFFAOYSA-N 0.000 description 2
- VTOQFOCYBTVOJZ-UHFFFAOYSA-N 3-bromopentane Chemical compound CCC(Br)CC VTOQFOCYBTVOJZ-UHFFFAOYSA-N 0.000 description 2
- XYIJRLBJDUKMMQ-UHFFFAOYSA-N 4-amino-2-anilinopyrimidine-5-carbaldehyde Chemical compound C1=C(C=O)C(N)=NC(NC=2C=CC=CC=2)=N1 XYIJRLBJDUKMMQ-UHFFFAOYSA-N 0.000 description 2
- XNDFBIJQHTVTSH-UHFFFAOYSA-N 8-(1-naphthalen-2-ylethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)N(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1CCCCC1 XNDFBIJQHTVTSH-UHFFFAOYSA-N 0.000 description 2
- OEXAHMVAPOVWKI-UHFFFAOYSA-N 8-(1-naphthalen-2-ylethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)N(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1C=CC=N1 OEXAHMVAPOVWKI-UHFFFAOYSA-N 0.000 description 2
- MGRGWTDDMZTMOA-UHFFFAOYSA-N 8-(1-phenylpropan-2-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C)CC1=CC=CC=C1 MGRGWTDDMZTMOA-UHFFFAOYSA-N 0.000 description 2
- PUNQGQMOJDJBNC-UHFFFAOYSA-N 8-(1-phenylpropan-2-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C)CC1=CC=CC=C1 PUNQGQMOJDJBNC-UHFFFAOYSA-N 0.000 description 2
- IVKSZDWJUMKXHC-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-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)N2C3C4CCC(C4)C3)C2=N1 IVKSZDWJUMKXHC-UHFFFAOYSA-N 0.000 description 2
- KBKMMHVXANSNHU-UHFFFAOYSA-N 8-(3-hydroxypropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.N=1C=C2C=CC(=O)N(CCCO)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 KBKMMHVXANSNHU-UHFFFAOYSA-N 0.000 description 2
- GKJQMYHWNKQWAN-UHFFFAOYSA-N 8-(oxan-4-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCOCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 GKJQMYHWNKQWAN-UHFFFAOYSA-N 0.000 description 2
- VRLRVCVCVQBKIV-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methylamino]-2-methylsulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1CNN1C(=O)C=CC2=CN=C(S(C)(=O)=O)N=C21 VRLRVCVCVQBKIV-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 101150053721 Cdk5 gene Proteins 0.000 description 2
- 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 description 2
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108060006698 EGF receptor Proteins 0.000 description 2
- 102000009024 Epidermal Growth Factor Human genes 0.000 description 2
- 101800003838 Epidermal growth factor Proteins 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 102000009465 Growth Factor Receptors Human genes 0.000 description 2
- 108010009202 Growth Factor Receptors Proteins 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699660 Mus musculus Species 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
- 102000001253 Protein Kinase Human genes 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 201000000582 Retinoblastoma Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920004890 Triton X-100 Polymers 0.000 description 2
- 239000013504 Triton X-100 Substances 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000012292 cell migration Effects 0.000 description 2
- 230000005754 cellular signaling Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000007933 dermal patch Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229940116977 epidermal growth factor Drugs 0.000 description 2
- 239000006167 equilibration buffer Substances 0.000 description 2
- JCTZRCYKNANLNQ-UHFFFAOYSA-N ethyl 2-anilino-4-(ethylamino)pyrimidine-5-carboxylate Chemical compound C1=C(C(=O)OCC)C(NCC)=NC(NC=2C=CC=CC=2)=N1 JCTZRCYKNANLNQ-UHFFFAOYSA-N 0.000 description 2
- BGPKUAJPRLFEIP-UHFFFAOYSA-N ethyl 4-(ethylamino)-2-methylsulfinylpyrimidine-5-carboxylate Chemical compound CCNC1=NC(S(C)=O)=NC=C1C(=O)OCC BGPKUAJPRLFEIP-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 239000012139 lysis buffer Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 201000001441 melanoma Diseases 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 210000002464 muscle smooth vascular Anatomy 0.000 description 2
- 238000011580 nude mouse model Methods 0.000 description 2
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003140 primary amides Chemical class 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 229940026235 propylene glycol monolaurate Drugs 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- FREJAOSUHFGDBW-UHFFFAOYSA-N pyrimidine-5-carbaldehyde Chemical compound O=CC1=CN=CN=C1 FREJAOSUHFGDBW-UHFFFAOYSA-N 0.000 description 2
- 229940048084 pyrophosphate Drugs 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003462 sulfoxides Chemical group 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 2
- 241000701447 unidentified baculovirus Species 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- PFDUBQQHEHJNQX-UHFFFAOYSA-N 1-(4-aminophenyl)-n,n-dimethylpiperidin-4-amine Chemical compound C1CC(N(C)C)CCN1C1=CC=C(N)C=C1 PFDUBQQHEHJNQX-UHFFFAOYSA-N 0.000 description 1
- GFPPPMAWVWTROZ-UHFFFAOYSA-N 1-(4-aminophenyl)piperidin-3-ol Chemical compound C1=CC(N)=CC=C1N1CC(O)CCC1 GFPPPMAWVWTROZ-UHFFFAOYSA-N 0.000 description 1
- BJXPIIDUCADEKU-UHFFFAOYSA-N 1-(4-aminophenyl)piperidin-4-ol Chemical compound C1=CC(N)=CC=C1N1CCC(O)CC1 BJXPIIDUCADEKU-UHFFFAOYSA-N 0.000 description 1
- GFDHQOUUEVQAPD-UHFFFAOYSA-N 1-(4-nitrophenyl)-4-piperidin-1-ylpiperidine Chemical group C1=CC([N+](=O)[O-])=CC=C1N1CCC(N2CCCCC2)CC1 GFDHQOUUEVQAPD-UHFFFAOYSA-N 0.000 description 1
- QZGBEKMQNFGXSX-UHFFFAOYSA-N 1-(4-nitrophenyl)piperidin-3-ol Chemical compound C1C(O)CCCN1C1=CC=C([N+]([O-])=O)C=C1 QZGBEKMQNFGXSX-UHFFFAOYSA-N 0.000 description 1
- RNPWPESLLCUROD-UHFFFAOYSA-N 1-(4-nitrophenyl)piperidin-4-ol Chemical compound C1CC(O)CCN1C1=CC=C([N+]([O-])=O)C=C1 RNPWPESLLCUROD-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
- XFBJBPQKWMSYER-UHFFFAOYSA-N 2-(2-anilino-7-oxopyrido[2,3-d]pyrimidin-8-yl)propanenitrile Chemical compound N=1C=C2C=CC(=O)N(C(C#N)C)C2=NC=1NC1=CC=CC=C1 XFBJBPQKWMSYER-UHFFFAOYSA-N 0.000 description 1
- KYPGQSBWOBULBP-UHFFFAOYSA-N 2-(3-bromo-2,2-dimethylpropoxy)oxane Chemical compound BrCC(C)(C)COC1CCCCO1 KYPGQSBWOBULBP-UHFFFAOYSA-N 0.000 description 1
- HBXHHKNBVUKMQK-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(2,2,2-trichloro-1-phenylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C(Cl)(Cl)Cl)C1=CC=CC=C1 HBXHHKNBVUKMQK-UHFFFAOYSA-N 0.000 description 1
- INKGTOPEMSFHDK-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(2,2,2-trifluoro-1-phenylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C(F)(F)F)C1=CC=CC=C1 INKGTOPEMSFHDK-UHFFFAOYSA-N 0.000 description 1
- LIQCTDHGAOKOEA-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C2(C)CCC1C(C)(C)C2N(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1CCCCC1 LIQCTDHGAOKOEA-UHFFFAOYSA-N 0.000 description 1
- DJXMRAXKUBKCNA-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(2-propan-2-ylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC(C)C1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 DJXMRAXKUBKCNA-UHFFFAOYSA-N 0.000 description 1
- YKACJAXJNDHFFY-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(2-thiophen-2-ylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCC=3SC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 YKACJAXJNDHFFY-UHFFFAOYSA-N 0.000 description 1
- YXRXZHYALSVTJU-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(3,3,5-trimethylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)(C)CC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 YXRXZHYALSVTJU-UHFFFAOYSA-N 0.000 description 1
- YQOQRKCYCZHYQN-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(4-propan-2-ylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 YQOQRKCYCZHYQN-UHFFFAOYSA-N 0.000 description 1
- IVKBKNVKNZIBNM-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(9h-xanthen-9-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4OC4=CC=CC=C43)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 IVKBKNVKNZIBNM-UHFFFAOYSA-N 0.000 description 1
- DNMNFQBPZPJPHV-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-(thiophen-2-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3SC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 DNMNFQBPZPJPHV-UHFFFAOYSA-N 0.000 description 1
- CETJMCHVHMEQFR-UHFFFAOYSA-N 2-(4-piperidin-1-ylanilino)-8-[2,2,2-trichloro-1-(4-fluorophenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(C(Cl)(Cl)Cl)N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 CETJMCHVHMEQFR-UHFFFAOYSA-N 0.000 description 1
- HRCUSNAYFLFIKN-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4CCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 HRCUSNAYFLFIKN-UHFFFAOYSA-N 0.000 description 1
- YYISLHFPZXMQGG-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(1,2,3,4-tetrahydronaphthalen-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4=CC=CC=C4CC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 YYISLHFPZXMQGG-UHFFFAOYSA-N 0.000 description 1
- AUOTUKNUVILJIE-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(2,2,2-trichloro-1-phenylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C(Cl)(Cl)Cl)C1=CC=CC=C1 AUOTUKNUVILJIE-UHFFFAOYSA-N 0.000 description 1
- GKAQUIRMRXGOLP-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(2,2,2-trifluoro-1-phenylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C(F)(F)F)C1=CC=CC=C1 GKAQUIRMRXGOLP-UHFFFAOYSA-N 0.000 description 1
- GXBPDXMCEZFVQB-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(2,2,2-trifluoroethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(F)(F)F)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 GXBPDXMCEZFVQB-UHFFFAOYSA-N 0.000 description 1
- OBSZMQBACDKSJD-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C2(C)CCC1C(C)(C)C2N(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1C=CC=N1 OBSZMQBACDKSJD-UHFFFAOYSA-N 0.000 description 1
- BDQWOLROBKUFGH-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(2-thiophen-2-ylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCC=3SC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 BDQWOLROBKUFGH-UHFFFAOYSA-N 0.000 description 1
- SQYMKXSHIVYSNZ-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(3,3,5-trimethylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)(C)CC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 SQYMKXSHIVYSNZ-UHFFFAOYSA-N 0.000 description 1
- YJIOHRJAVDOBJP-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(9h-xanthen-9-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4OC4=CC=CC=C43)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 YJIOHRJAVDOBJP-UHFFFAOYSA-N 0.000 description 1
- CTYLTWXEQMLOHW-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-(thiophen-2-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3SC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 CTYLTWXEQMLOHW-UHFFFAOYSA-N 0.000 description 1
- BIQCBHYBPBGYGO-UHFFFAOYSA-N 2-(4-pyrazol-1-ylanilino)-8-[2,2,2-trichloro-1-(4-fluorophenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(C(Cl)(Cl)Cl)N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 BIQCBHYBPBGYGO-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- UIHSNODUZXRNQG-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methylamino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=NC=C(C=CC(=O)N2C(C)C)C2=N1 UIHSNODUZXRNQG-UHFFFAOYSA-N 0.000 description 1
- NOWRFBYPZGTKLQ-UHFFFAOYSA-N 2-[1-(4-aminophenyl)piperidin-4-yl]ethanol Chemical compound C1=CC(N)=CC=C1N1CCC(CCO)CC1 NOWRFBYPZGTKLQ-UHFFFAOYSA-N 0.000 description 1
- MNRDSPBDDKOWKJ-UHFFFAOYSA-N 2-[1-(4-nitrophenyl)piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1C1=CC=C([N+]([O-])=O)C=C1 MNRDSPBDDKOWKJ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OPRITKBKJTVTJU-UHFFFAOYSA-N 2-[2-[4-(4-methylpiperazin-1-yl)anilino]-7-oxopyrido[2,3-d]pyrimidin-8-yl]propanenitrile Chemical compound N=1C=C2C=CC(=O)N(C(C#N)C)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 OPRITKBKJTVTJU-UHFFFAOYSA-N 0.000 description 1
- UAIKFYFXPAJQHE-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4=CC=CC=C4CCC3)C2=N1 UAIKFYFXPAJQHE-UHFFFAOYSA-N 0.000 description 1
- PBEIJOQEHUHHLY-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(1,2,3,4-tetrahydronaphthalen-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CC4=CC=CC=C4CC3)C2=N1 PBEIJOQEHUHHLY-UHFFFAOYSA-N 0.000 description 1
- ZGTAEYWTWAURDY-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(1-phenylheptyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(CCCCCC)C1=CC=CC=C1 ZGTAEYWTWAURDY-UHFFFAOYSA-N 0.000 description 1
- STYZVDSMBBGJRQ-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(1-phenylprop-2-ynyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C(C#C)C=3C=CC=CC=3)C2=N1 STYZVDSMBBGJRQ-UHFFFAOYSA-N 0.000 description 1
- XFTFBUSOKBIEJX-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(1-phenylpropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(CC)C1=CC=CC=C1 XFTFBUSOKBIEJX-UHFFFAOYSA-N 0.000 description 1
- KJSDLESBTACGCM-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2,2,2-trichloro-1-phenylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C(C=3C=CC=CC=3)C(Cl)(Cl)Cl)C2=N1 KJSDLESBTACGCM-UHFFFAOYSA-N 0.000 description 1
- NLIUODSJKVKLDN-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2,2,2-trifluoro-1-phenylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C(C=3C=CC=CC=3)C(F)(F)F)C2=N1 NLIUODSJKVKLDN-UHFFFAOYSA-N 0.000 description 1
- IFJUWGIWLWWBDW-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2,2,3,3,3-pentafluoropropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CC(F)(F)C(F)(F)F)C2=N1 IFJUWGIWLWWBDW-UHFFFAOYSA-N 0.000 description 1
- DCYFZPQREUSCMX-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2-naphthalen-2-ylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CCC=3C=C4C=CC=CC4=CC=3)C2=N1 DCYFZPQREUSCMX-UHFFFAOYSA-N 0.000 description 1
- QCTINNQIIRVHPN-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2-oxocyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3C(CCCC3)=O)C2=N1 QCTINNQIIRVHPN-UHFFFAOYSA-N 0.000 description 1
- QYMKGLIFACJELA-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2-phenoxyethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CCOC=3C=CC=CC=3)C2=N1 QYMKGLIFACJELA-UHFFFAOYSA-N 0.000 description 1
- CAVPUDHJXXPWLT-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2-phenyl-1,3-dioxan-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3COC(OC3)C=3C=CC=CC=3)C2=N1 CAVPUDHJXXPWLT-UHFFFAOYSA-N 0.000 description 1
- KVKSDTNOYFWTRS-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2-phenylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3C(CCCC3)C=3C=CC=CC=3)C2=N1 KVKSDTNOYFWTRS-UHFFFAOYSA-N 0.000 description 1
- LATOXIIXYITGHV-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(2-thiophen-2-ylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CCC=3SC=CC=3)C2=N1 LATOXIIXYITGHV-UHFFFAOYSA-N 0.000 description 1
- NSCNWIWUPDVQNM-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(3-phenylprop-2-ynyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CC#CC=3C=CC=CC=3)C2=N1 NSCNWIWUPDVQNM-UHFFFAOYSA-N 0.000 description 1
- PLBOSTWRIGMJOV-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(4-propan-2-ylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 PLBOSTWRIGMJOV-UHFFFAOYSA-N 0.000 description 1
- IWMTUXIZSRIALJ-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(9h-xanthen-9-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4=CC=CC=C4OC4=CC=CC=C43)C2=N1 IWMTUXIZSRIALJ-UHFFFAOYSA-N 0.000 description 1
- OXSWEDYLIGIQPD-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(oxan-4-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCOCC3)C2=N1 OXSWEDYLIGIQPD-UHFFFAOYSA-N 0.000 description 1
- IKLUDOBFQCNYTD-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(oxolan-2-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CC3OCCC3)C2=N1 IKLUDOBFQCNYTD-UHFFFAOYSA-N 0.000 description 1
- HLCJAPKJDOVKEV-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-(thiophen-2-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CC=3SC=CC=3)C2=N1 HLCJAPKJDOVKEV-UHFFFAOYSA-N 0.000 description 1
- GDSAXWVSFFXKKG-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-[(3-phenoxyphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2CC=3C=C(OC=4C=CC=CC=4)C=CC=3)C2=N1 GDSAXWVSFFXKKG-UHFFFAOYSA-N 0.000 description 1
- MFUJEHHTWMTWGR-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-[1-(4-phenylphenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(C)C(C=C1)=CC=C1C1=CC=CC=C1 MFUJEHHTWMTWGR-UHFFFAOYSA-N 0.000 description 1
- VNGONGVLKDJDKC-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-[phenyl-[2-(trifluoromethyl)phenyl]methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C(C=3C=CC=CC=3)C=3C(=CC=CC=3)C(F)(F)F)C2=N1 VNGONGVLKDJDKC-UHFFFAOYSA-N 0.000 description 1
- GBZBDRSTRQUIDT-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-oct-1-yn-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C#C)CCCCC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 GBZBDRSTRQUIDT-UHFFFAOYSA-N 0.000 description 1
- IUVQDNWEJOXHEC-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-octan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CCCCCC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 IUVQDNWEJOXHEC-UHFFFAOYSA-N 0.000 description 1
- VVQTUVMCJFKYNY-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-pent-1-yn-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C#C)CC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 VVQTUVMCJFKYNY-UHFFFAOYSA-N 0.000 description 1
- XZYJWDCKHAFYJP-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]-8-pent-4-yn-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(CC#C)C)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 XZYJWDCKHAFYJP-UHFFFAOYSA-N 0.000 description 1
- ADJQXTCGOAOSCV-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-8-(2-phenylmethoxyethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=CC(=O)N2CCOCC=3C=CC=CC=3)C2=N1 ADJQXTCGOAOSCV-UHFFFAOYSA-N 0.000 description 1
- GOUZHHGOPDXVRI-UHFFFAOYSA-N 2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 GOUZHHGOPDXVRI-UHFFFAOYSA-N 0.000 description 1
- QWEFADUJIDEPLK-UHFFFAOYSA-N 2-[7-oxo-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-8-yl]propanenitrile Chemical compound N=1C=C2C=CC(=O)N(C(C#N)C)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 QWEFADUJIDEPLK-UHFFFAOYSA-N 0.000 description 1
- HCMAPQRNGXHLMU-UHFFFAOYSA-N 2-[7-oxo-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-8-yl]propanenitrile Chemical compound N=1C=C2C=CC(=O)N(C(C#N)C)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 HCMAPQRNGXHLMU-UHFFFAOYSA-N 0.000 description 1
- MTNAKYDVPDVONX-UHFFFAOYSA-N 2-amino-8-cyclohexylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(N)=NC=C2C=CC(=O)N1C1CCCCC1 MTNAKYDVPDVONX-UHFFFAOYSA-N 0.000 description 1
- ZYFVLSKRUYEIDF-UHFFFAOYSA-N 2-amino-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound NC1=NC=C2C=CC(=O)N(C(C)C)C2=N1 ZYFVLSKRUYEIDF-UHFFFAOYSA-N 0.000 description 1
- BXSJPZGODRCPIX-UHFFFAOYSA-N 2-anilino-8-(1,1,1,3,3,3-hexafluoropropan-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C(F)(F)F)C(F)(F)F)C2=NC=1NC1=CC=CC=C1 BXSJPZGODRCPIX-UHFFFAOYSA-N 0.000 description 1
- RUMNPQFNDULVMQ-UHFFFAOYSA-N 2-anilino-8-(1,1-diphenylpropan-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 RUMNPQFNDULVMQ-UHFFFAOYSA-N 0.000 description 1
- YAZAHDLJYDHEKN-UHFFFAOYSA-N 2-anilino-8-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4CCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 YAZAHDLJYDHEKN-UHFFFAOYSA-N 0.000 description 1
- AMZKDMQPHKSJPK-UHFFFAOYSA-N 2-anilino-8-(1,2,3,4-tetrahydronaphthalen-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4=CC=CC=C4CC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 AMZKDMQPHKSJPK-UHFFFAOYSA-N 0.000 description 1
- HCDLELOCAJAWOA-UHFFFAOYSA-N 2-anilino-8-(1,2-dihydroacenaphthylen-1-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C=4C=CC=C5C=CC=C(C=45)C3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 HCDLELOCAJAWOA-UHFFFAOYSA-N 0.000 description 1
- MUIBSBLNCFQNAO-UHFFFAOYSA-N 2-anilino-8-(1,5-diphenoxypentan-3-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(CCOC=3C=CC=CC=3)CCOC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 MUIBSBLNCFQNAO-UHFFFAOYSA-N 0.000 description 1
- DIMGJPJRUZQPNV-UHFFFAOYSA-N 2-anilino-8-(1-cyclohexylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C)C1CCCCC1 DIMGJPJRUZQPNV-UHFFFAOYSA-N 0.000 description 1
- CUHGRKANGNOAOG-UHFFFAOYSA-N 2-anilino-8-(1-cyclohexylpropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(CC)C1CCCCC1 CUHGRKANGNOAOG-UHFFFAOYSA-N 0.000 description 1
- FLAJQQNHXNNNQP-UHFFFAOYSA-N 2-anilino-8-(1-methoxypropan-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)COC)C2=NC=1NC1=CC=CC=C1 FLAJQQNHXNNNQP-UHFFFAOYSA-N 0.000 description 1
- PYOWVCDRZARUTP-UHFFFAOYSA-N 2-anilino-8-(1-phenylheptyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(CCCCCC)C1=CC=CC=C1 PYOWVCDRZARUTP-UHFFFAOYSA-N 0.000 description 1
- CQWSTPKPURGNHE-UHFFFAOYSA-N 2-anilino-8-(1-phenylprop-2-ynyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C#C)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 CQWSTPKPURGNHE-UHFFFAOYSA-N 0.000 description 1
- LFJDQDFWXQTFMC-UHFFFAOYSA-N 2-anilino-8-(1-phenylpropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(CC)C1=CC=CC=C1 LFJDQDFWXQTFMC-UHFFFAOYSA-N 0.000 description 1
- YQSQZBTYSJOPGU-UHFFFAOYSA-N 2-anilino-8-(2,2,2-trichloro-1-phenylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C(Cl)(Cl)Cl)C1=CC=CC=C1 YQSQZBTYSJOPGU-UHFFFAOYSA-N 0.000 description 1
- HRBIHDXJWQPQLV-UHFFFAOYSA-N 2-anilino-8-(2,2,2-trifluoro-1-phenylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C(F)(F)F)C1=CC=CC=C1 HRBIHDXJWQPQLV-UHFFFAOYSA-N 0.000 description 1
- PKVBGCCNMVWBHV-UHFFFAOYSA-N 2-anilino-8-(2,2,2-trifluoroethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(F)(F)F)C2=NC=1NC1=CC=CC=C1 PKVBGCCNMVWBHV-UHFFFAOYSA-N 0.000 description 1
- MURSTUBIGZRLHI-UHFFFAOYSA-N 2-anilino-8-(2,2,3,3,3-pentafluoropropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(F)(F)C(F)(F)F)C2=NC=1NC1=CC=CC=C1 MURSTUBIGZRLHI-UHFFFAOYSA-N 0.000 description 1
- CTZRKJIESNMCNK-UHFFFAOYSA-N 2-anilino-8-(2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C2(C)CCC1C(C)(C)C2N(C(C=CC1=CN=2)=O)C1=NC=2NC1=CC=CC=C1 CTZRKJIESNMCNK-UHFFFAOYSA-N 0.000 description 1
- HXBJBMAZWBXCGS-UHFFFAOYSA-N 2-anilino-8-(2,3-dihydro-1h-inden-1-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4CC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 HXBJBMAZWBXCGS-UHFFFAOYSA-N 0.000 description 1
- GXAZQYAKMOBGGB-UHFFFAOYSA-N 2-anilino-8-(2,3-dihydro-1h-inden-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4=CC=CC=C4C3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 GXAZQYAKMOBGGB-UHFFFAOYSA-N 0.000 description 1
- ZZBMORKKHOWTCM-UHFFFAOYSA-N 2-anilino-8-(2,3-dimethylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1C(C)CCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 ZZBMORKKHOWTCM-UHFFFAOYSA-N 0.000 description 1
- ROADGSTZNDNXHY-UHFFFAOYSA-N 2-anilino-8-(2,5-dimethylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 ROADGSTZNDNXHY-UHFFFAOYSA-N 0.000 description 1
- RECALBWEYRUQDY-UHFFFAOYSA-N 2-anilino-8-(2,6-dimethylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1CCCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 RECALBWEYRUQDY-UHFFFAOYSA-N 0.000 description 1
- RZXPHEPKGUELBQ-UHFFFAOYSA-N 2-anilino-8-(2-butoxyethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCCCC)C2=NC=1NC1=CC=CC=C1 RZXPHEPKGUELBQ-UHFFFAOYSA-N 0.000 description 1
- YWESBEQDSQDRAX-UHFFFAOYSA-N 2-anilino-8-(2-cyclopropylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCC3CC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 YWESBEQDSQDRAX-UHFFFAOYSA-N 0.000 description 1
- ORVZGMRYPIALKB-UHFFFAOYSA-N 2-anilino-8-(2-ethoxyethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCC)C2=NC=1NC1=CC=CC=C1 ORVZGMRYPIALKB-UHFFFAOYSA-N 0.000 description 1
- CODPSUVKJCWVCB-UHFFFAOYSA-N 2-anilino-8-(2-ethylhexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(CC)CCCC)C2=NC=1NC1=CC=CC=C1 CODPSUVKJCWVCB-UHFFFAOYSA-N 0.000 description 1
- IXFZVBOVCAQWJR-UHFFFAOYSA-N 2-anilino-8-(2-methyl-3-oxobutyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(C)C(C)=O)C2=NC=1NC1=CC=CC=C1 IXFZVBOVCAQWJR-UHFFFAOYSA-N 0.000 description 1
- SJJMMFMILJSUEX-UHFFFAOYSA-N 2-anilino-8-(2-methyl-5-propan-2-ylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C(C)C)CCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 SJJMMFMILJSUEX-UHFFFAOYSA-N 0.000 description 1
- FBBNKDDQBWNPLR-UHFFFAOYSA-N 2-anilino-8-(2-methylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 FBBNKDDQBWNPLR-UHFFFAOYSA-N 0.000 description 1
- SCDVNYWJURYFQA-UHFFFAOYSA-N 2-anilino-8-(2-naphthalen-2-ylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCC=3C=C4C=CC=CC4=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 SCDVNYWJURYFQA-UHFFFAOYSA-N 0.000 description 1
- NNXLXQLXJXYKME-UHFFFAOYSA-N 2-anilino-8-(2-oxocyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 NNXLXQLXJXYKME-UHFFFAOYSA-N 0.000 description 1
- OGENZPWSNFXJKN-UHFFFAOYSA-N 2-anilino-8-(2-phenoxyethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCOC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 OGENZPWSNFXJKN-UHFFFAOYSA-N 0.000 description 1
- DTHITBDHEXBGNY-UHFFFAOYSA-N 2-anilino-8-(2-phenyl-1,3-dioxan-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3COC(OC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 DTHITBDHEXBGNY-UHFFFAOYSA-N 0.000 description 1
- GRPOEMQKWRBVKL-UHFFFAOYSA-N 2-anilino-8-(2-phenylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C(CCCC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 GRPOEMQKWRBVKL-UHFFFAOYSA-N 0.000 description 1
- RTWAXEJNMRDNFL-UHFFFAOYSA-N 2-anilino-8-(2-propan-2-ylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC(C)C1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 RTWAXEJNMRDNFL-UHFFFAOYSA-N 0.000 description 1
- IAELUJRXYQPMMS-UHFFFAOYSA-N 2-anilino-8-(2-thiophen-2-ylethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCC=3SC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 IAELUJRXYQPMMS-UHFFFAOYSA-N 0.000 description 1
- ZKMJEILOPXSAOV-UHFFFAOYSA-N 2-anilino-8-(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-2-methyloctan-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)(C)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F)C2=NC=1NC1=CC=CC=C1 ZKMJEILOPXSAOV-UHFFFAOYSA-N 0.000 description 1
- IYAQYAVQKFWPLI-UHFFFAOYSA-N 2-anilino-8-(3,3,5-trimethylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)(C)CC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 IYAQYAVQKFWPLI-UHFFFAOYSA-N 0.000 description 1
- VLVKAJATJLTPEQ-UHFFFAOYSA-N 2-anilino-8-(3,3-dimethylbutyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCC(C)(C)C)C2=NC=1NC1=CC=CC=C1 VLVKAJATJLTPEQ-UHFFFAOYSA-N 0.000 description 1
- AFQSPMLLHGTWKR-UHFFFAOYSA-N 2-anilino-8-(3,5-dimethylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 AFQSPMLLHGTWKR-UHFFFAOYSA-N 0.000 description 1
- YXIATNGGPSZPFU-UHFFFAOYSA-N 2-anilino-8-(3-bicyclo[2.2.1]heptanylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3C4CCC(C4)C3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 YXIATNGGPSZPFU-UHFFFAOYSA-N 0.000 description 1
- GMXQBWRXKRABIX-UHFFFAOYSA-N 2-anilino-8-(3-methoxypropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCCOC)C2=NC=1NC1=CC=CC=C1 GMXQBWRXKRABIX-UHFFFAOYSA-N 0.000 description 1
- WUZXQZWLOYVOQP-UHFFFAOYSA-N 2-anilino-8-(3-methylbut-2-enyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC=C(C)C)C2=NC=1NC1=CC=CC=C1 WUZXQZWLOYVOQP-UHFFFAOYSA-N 0.000 description 1
- BGHMFETVTSVCKS-UHFFFAOYSA-N 2-anilino-8-(3-methylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 BGHMFETVTSVCKS-UHFFFAOYSA-N 0.000 description 1
- LANYVYPDBGLCKP-UHFFFAOYSA-N 2-anilino-8-(3-phenylprop-2-ynyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC#CC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 LANYVYPDBGLCKP-UHFFFAOYSA-N 0.000 description 1
- LLPCQAPFINNEOA-UHFFFAOYSA-N 2-anilino-8-(4-butan-2-ylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)CC)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 LLPCQAPFINNEOA-UHFFFAOYSA-N 0.000 description 1
- RYOOZGAWQVBFOJ-UHFFFAOYSA-N 2-anilino-8-(4-cyclohexylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCC(CC3)C3CCCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 RYOOZGAWQVBFOJ-UHFFFAOYSA-N 0.000 description 1
- KCTVDSNQUFHOPD-UHFFFAOYSA-N 2-anilino-8-(4-methylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 KCTVDSNQUFHOPD-UHFFFAOYSA-N 0.000 description 1
- PEOKSUDVRQIXAW-UHFFFAOYSA-N 2-anilino-8-(4-propan-2-ylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 PEOKSUDVRQIXAW-UHFFFAOYSA-N 0.000 description 1
- NLCQCPRFFHBIAK-UHFFFAOYSA-N 2-anilino-8-(4-tert-butylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)(C)C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 NLCQCPRFFHBIAK-UHFFFAOYSA-N 0.000 description 1
- NZNHHPBDBAOEAU-UHFFFAOYSA-N 2-anilino-8-(5-bicyclo[2.2.1]hept-2-enyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CC(C=C4)C3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 NZNHHPBDBAOEAU-UHFFFAOYSA-N 0.000 description 1
- OWCAXBXPGFJFDN-UHFFFAOYSA-N 2-anilino-8-(5-methyl-2-propan-2-ylcyclohexyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC(C)C1CCC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 OWCAXBXPGFJFDN-UHFFFAOYSA-N 0.000 description 1
- REILAARGDXFKFX-UHFFFAOYSA-N 2-anilino-8-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4CCC4=CC=CC=C43)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 REILAARGDXFKFX-UHFFFAOYSA-N 0.000 description 1
- GYXNINNYBKSSBQ-UHFFFAOYSA-N 2-anilino-8-(9h-fluoren-9-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4C4=CC=CC=C43)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 GYXNINNYBKSSBQ-UHFFFAOYSA-N 0.000 description 1
- RXSXQVDEKAZAAO-UHFFFAOYSA-N 2-anilino-8-(9h-xanthen-9-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4OC4=CC=CC=C43)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 RXSXQVDEKAZAAO-UHFFFAOYSA-N 0.000 description 1
- OLCYNUGEPBWAOI-UHFFFAOYSA-N 2-anilino-8-(cyclohex-3-en-1-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3CC=CCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 OLCYNUGEPBWAOI-UHFFFAOYSA-N 0.000 description 1
- RDEDLDISKDABMY-UHFFFAOYSA-N 2-anilino-8-(dicyclohexylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C3CCCCC3)C3CCCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 RDEDLDISKDABMY-UHFFFAOYSA-N 0.000 description 1
- LWNPWUIYYLPWDG-UHFFFAOYSA-N 2-anilino-8-(furan-2-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3OC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 LWNPWUIYYLPWDG-UHFFFAOYSA-N 0.000 description 1
- CRTNLXGNXQMYAM-UHFFFAOYSA-N 2-anilino-8-(furan-3-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3=COC=C3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 CRTNLXGNXQMYAM-UHFFFAOYSA-N 0.000 description 1
- SLXGRTPNUQKKSJ-UHFFFAOYSA-N 2-anilino-8-(oxan-4-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCOCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 SLXGRTPNUQKKSJ-UHFFFAOYSA-N 0.000 description 1
- SSJQQYUICADLAD-UHFFFAOYSA-N 2-anilino-8-(oxolan-2-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3OCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 SSJQQYUICADLAD-UHFFFAOYSA-N 0.000 description 1
- HVRPVSCMQWYQGH-UHFFFAOYSA-N 2-anilino-8-(thiophen-2-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3SC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 HVRPVSCMQWYQGH-UHFFFAOYSA-N 0.000 description 1
- RTLDGHICQCXBSE-UHFFFAOYSA-N 2-anilino-8-[(2-methyl-3-bicyclo[2.2.1]heptanyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1C(C2)CCC2C1CN(C(C=CC1=CN=2)=O)C1=NC=2NC1=CC=CC=C1 RTLDGHICQCXBSE-UHFFFAOYSA-N 0.000 description 1
- GGYYNJLLXWAMHZ-UHFFFAOYSA-N 2-anilino-8-[(2-methylphenyl)-phenylmethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=CC=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC=CC=3)N=C21)=O)C1=CC=CC=C1 GGYYNJLLXWAMHZ-UHFFFAOYSA-N 0.000 description 1
- HNSULVLPBSSIQJ-UHFFFAOYSA-N 2-anilino-8-[(3,5-dimethoxyphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC(OC)=CC(CN2C(C=CC3=CN=C(NC=4C=CC=CC=4)N=C32)=O)=C1 HNSULVLPBSSIQJ-UHFFFAOYSA-N 0.000 description 1
- UXVIDCJQCKRDHO-UHFFFAOYSA-N 2-anilino-8-[(3-ethyloxetan-3-yl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1CC1(CC)COC1 UXVIDCJQCKRDHO-UHFFFAOYSA-N 0.000 description 1
- PBIIHLSQHBOXRU-UHFFFAOYSA-N 2-anilino-8-[(3-methylphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=CC=CC(CN2C(C=CC3=CN=C(NC=4C=CC=CC=4)N=C32)=O)=C1 PBIIHLSQHBOXRU-UHFFFAOYSA-N 0.000 description 1
- AJHZYHKMYXPTMM-UHFFFAOYSA-N 2-anilino-8-[(3-phenoxyphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3C=C(OC=4C=CC=CC=4)C=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 AJHZYHKMYXPTMM-UHFFFAOYSA-N 0.000 description 1
- JAWCPKZPHAWPBW-UHFFFAOYSA-N 2-anilino-8-[(4-chloro-2-nitrophenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 JAWCPKZPHAWPBW-UHFFFAOYSA-N 0.000 description 1
- MXCKUHJLZAWMQD-UHFFFAOYSA-N 2-anilino-8-[(4-ethylphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(CC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 MXCKUHJLZAWMQD-UHFFFAOYSA-N 0.000 description 1
- DTPXUDGWLXATJZ-UHFFFAOYSA-N 2-anilino-8-[(4-methoxyphenyl)-pyridin-2-ylmethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC=CC=3)N=C21)=O)C1=CC=CC=N1 DTPXUDGWLXATJZ-UHFFFAOYSA-N 0.000 description 1
- HGQOJVPJIALLKE-UHFFFAOYSA-N 2-anilino-8-[(4-methylphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 HGQOJVPJIALLKE-UHFFFAOYSA-N 0.000 description 1
- SSWKIGLEQTXWEF-UHFFFAOYSA-N 2-anilino-8-[(4-methylsulfanylphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(SC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 SSWKIGLEQTXWEF-UHFFFAOYSA-N 0.000 description 1
- WBAZQWRVGIRAIC-UHFFFAOYSA-N 2-anilino-8-[1-(2-bromophenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C)C1=CC=CC=C1Br WBAZQWRVGIRAIC-UHFFFAOYSA-N 0.000 description 1
- ZIELAVKHMQTIIQ-UHFFFAOYSA-N 2-anilino-8-[1-(3,4-dichlorophenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C)C1=CC=C(Cl)C(Cl)=C1 ZIELAVKHMQTIIQ-UHFFFAOYSA-N 0.000 description 1
- ACBOTNYZYHRWGV-UHFFFAOYSA-N 2-anilino-8-[1-(4-methoxyphenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C(C)N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 ACBOTNYZYHRWGV-UHFFFAOYSA-N 0.000 description 1
- AVAUQPABPFHXKI-UHFFFAOYSA-N 2-anilino-8-[1-(4-methylphenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C)C1=CC=C(C)C=C1 AVAUQPABPFHXKI-UHFFFAOYSA-N 0.000 description 1
- ULEVZKLIABARGN-UHFFFAOYSA-N 2-anilino-8-[1-(4-phenylphenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C=CC(=O)N1C(C)C(C=C1)=CC=C1C1=CC=CC=C1 ULEVZKLIABARGN-UHFFFAOYSA-N 0.000 description 1
- WOFFLFJKTHZHDS-UHFFFAOYSA-N 2-anilino-8-[2,2,2-trichloro-1-(4-fluorophenyl)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(C(Cl)(Cl)Cl)N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 WOFFLFJKTHZHDS-UHFFFAOYSA-N 0.000 description 1
- JXXTWCJFLKCJBD-UHFFFAOYSA-N 2-anilino-8-[2-(2-methoxyethoxy)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCCOC)C2=NC=1NC1=CC=CC=C1 JXXTWCJFLKCJBD-UHFFFAOYSA-N 0.000 description 1
- QPAFKKQMJDXRAW-UHFFFAOYSA-N 2-anilino-8-[2-(4-tert-butylphenoxy)ethyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C(C)(C)C)=CC=C1OCCN1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 QPAFKKQMJDXRAW-UHFFFAOYSA-N 0.000 description 1
- ZUPZPPNKDABWBO-UHFFFAOYSA-N 2-anilino-8-[4-(2-methylbutan-2-yl)cyclohexyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)(C)CC)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC=CC=3)N=C21 ZUPZPPNKDABWBO-UHFFFAOYSA-N 0.000 description 1
- NMLCMTVSZONHAJ-UHFFFAOYSA-N 2-anilino-8-[bis(4-fluorophenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC=CC=3)N=C21)=O)C1=CC=C(F)C=C1 NMLCMTVSZONHAJ-UHFFFAOYSA-N 0.000 description 1
- LUPYNJARDOYKCS-UHFFFAOYSA-N 2-anilino-8-[cyclohexyl(phenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C3CCCCC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 LUPYNJARDOYKCS-UHFFFAOYSA-N 0.000 description 1
- JIKDIRITOPHQBP-UHFFFAOYSA-N 2-anilino-8-[cyclopropyl-(4-fluorophenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC=CC=3)N=C21)=O)C1CC1 JIKDIRITOPHQBP-UHFFFAOYSA-N 0.000 description 1
- VXPBBUKDSHYSFU-UHFFFAOYSA-N 2-anilino-8-[phenyl-[2-(trifluoromethyl)phenyl]methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound FC(F)(F)C1=CC=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC=CC=3)N=C21)=O)C1=CC=CC=C1 VXPBBUKDSHYSFU-UHFFFAOYSA-N 0.000 description 1
- NAVFTSNHPBSYLO-UHFFFAOYSA-N 2-anilino-8-benzhydrylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 NAVFTSNHPBSYLO-UHFFFAOYSA-N 0.000 description 1
- BTPMDHBCRMZHGV-UHFFFAOYSA-N 2-anilino-8-cyclohex-2-en-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C=CCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 BTPMDHBCRMZHGV-UHFFFAOYSA-N 0.000 description 1
- OCQTXIZDOJIGPI-UHFFFAOYSA-N 2-anilino-8-cyclohex-3-en-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC=CCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 OCQTXIZDOJIGPI-UHFFFAOYSA-N 0.000 description 1
- STYZZHSWGXQUFR-UHFFFAOYSA-N 2-anilino-8-cyclooctylpyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCCCC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 STYZZHSWGXQUFR-UHFFFAOYSA-N 0.000 description 1
- FVALCJVWJJMQGL-UHFFFAOYSA-N 2-anilino-8-ethyl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC)C(=O)CCC2=CN=C1NC1=CC=CC=C1 FVALCJVWJJMQGL-UHFFFAOYSA-N 0.000 description 1
- PULYEYXWOCFDJE-UHFFFAOYSA-N 2-anilino-8-heptan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CCCCC)C2=NC=1NC1=CC=CC=C1 PULYEYXWOCFDJE-UHFFFAOYSA-N 0.000 description 1
- GYPIIKRWDBCVAQ-UHFFFAOYSA-N 2-anilino-8-hex-2-ynylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC#CCCC)C2=NC=1NC1=CC=CC=C1 GYPIIKRWDBCVAQ-UHFFFAOYSA-N 0.000 description 1
- YUKRSPZACXUMPF-UHFFFAOYSA-N 2-anilino-8-hex-3-yn-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C#CCC)C2=NC=1NC1=CC=CC=C1 YUKRSPZACXUMPF-UHFFFAOYSA-N 0.000 description 1
- KIXSJMAPRARGFT-UHFFFAOYSA-N 2-anilino-8-oct-1-yn-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C#C)CCCCC)C2=NC=1NC1=CC=CC=C1 KIXSJMAPRARGFT-UHFFFAOYSA-N 0.000 description 1
- CZCSDSREBYXOPG-UHFFFAOYSA-N 2-anilino-8-octan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CCCCCC)C2=NC=1NC1=CC=CC=C1 CZCSDSREBYXOPG-UHFFFAOYSA-N 0.000 description 1
- CONGGLMJQYXIBQ-UHFFFAOYSA-N 2-anilino-8-pent-1-yn-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C#C)CC)C2=NC=1NC1=CC=CC=C1 CONGGLMJQYXIBQ-UHFFFAOYSA-N 0.000 description 1
- YAHVKOQVKFWEOD-UHFFFAOYSA-N 2-anilino-8-pent-4-yn-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(CC#C)C)C2=NC=1NC1=CC=CC=C1 YAHVKOQVKFWEOD-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- WPUAPGRZGJOIBX-UHFFFAOYSA-N 2-methylsulfanyl-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)NC2=NC(SC)=NC=C21 WPUAPGRZGJOIBX-UHFFFAOYSA-N 0.000 description 1
- QFDMHXJBCKAKSG-UHFFFAOYSA-N 2-methylsulfonyl-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)NC2=NC(S(=O)(=O)C)=NC=C21 QFDMHXJBCKAKSG-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- RHMVAEDRHIPTGQ-UHFFFAOYSA-N 3-[1-(4-aminophenyl)piperidin-4-yl]propan-1-ol Chemical compound C1=CC(N)=CC=C1N1CCC(CCCO)CC1 RHMVAEDRHIPTGQ-UHFFFAOYSA-N 0.000 description 1
- VFJPEUZSPYZZPZ-UHFFFAOYSA-N 3-[1-(4-nitrophenyl)piperidin-4-yl]propan-1-ol Chemical compound C1CC(CCCO)CCN1C1=CC=C([N+]([O-])=O)C=C1 VFJPEUZSPYZZPZ-UHFFFAOYSA-N 0.000 description 1
- IARJTGLQURXMGQ-UHFFFAOYSA-N 3-[2-anilino-4-(ethylamino)pyrimidin-5-yl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(NCC)=NC(NC=2C=CC=CC=2)=N1 IARJTGLQURXMGQ-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NIDWUZTTXGJFNN-UHFFFAOYSA-N 3-bromopropoxybenzene Chemical compound BrCCCOC1=CC=CC=C1 NIDWUZTTXGJFNN-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- RCYMPYMITUEHOJ-UHFFFAOYSA-N 3-fluoro-2-methoxyaniline Chemical compound COC1=C(N)C=CC=C1F RCYMPYMITUEHOJ-UHFFFAOYSA-N 0.000 description 1
- LJWAPDSCYTZUJU-UHFFFAOYSA-N 3-fluoro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1F LJWAPDSCYTZUJU-UHFFFAOYSA-N 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
- MOZNZNKHRXRLLF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1 MOZNZNKHRXRLLF-UHFFFAOYSA-N 0.000 description 1
- UCAYCVGZQREMAR-UHFFFAOYSA-N 4-(cyclohexylamino)-2-methylsulfanylpyrimidine-5-carbaldehyde Chemical compound CSC1=NC=C(C=O)C(NC2CCCCC2)=N1 UCAYCVGZQREMAR-UHFFFAOYSA-N 0.000 description 1
- TWIGATDHHWUGHA-UHFFFAOYSA-N 4-(cyclopropylamino)-2-methylsulfanylpyrimidine-5-carbaldehyde Chemical compound CSC1=NC=C(C=O)C(NC2CC2)=N1 TWIGATDHHWUGHA-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- LFJGGGIWERIGNX-UHFFFAOYSA-N 4-[2-(diethylamino)ethoxy]aniline Chemical compound CCN(CC)CCOC1=CC=C(N)C=C1 LFJGGGIWERIGNX-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
- RKWMXFMTFOSKMW-UHFFFAOYSA-N 4-amino-2-anilinopyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(N)=NC(NC=2C=CC=CC=2)=N1 RKWMXFMTFOSKMW-UHFFFAOYSA-N 0.000 description 1
- WZJMGOSOGRMBPE-UHFFFAOYSA-N 4-amino-8-cyclohexyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=2N(C3CCCCC3)C(=O)C=CC=2C(N)=NC=1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 WZJMGOSOGRMBPE-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- ZVTSZDQXSJLQFW-UHFFFAOYSA-N 5-amino-8-cyclohexyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCN4CCOCC4)CC3)=NC=C2C(N)=CC(=O)N1C1CCCCC1 ZVTSZDQXSJLQFW-UHFFFAOYSA-N 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- HVCRFDROMWBRIK-UHFFFAOYSA-N 6-amino-8-cyclohexyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C(N)=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 HVCRFDROMWBRIK-UHFFFAOYSA-N 0.000 description 1
- FRDSIPZPAKNSFG-UHFFFAOYSA-N 8-(1,1,1,3,3,3-hexafluoropropan-2-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C(F)(F)F)C(F)(F)F)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 FRDSIPZPAKNSFG-UHFFFAOYSA-N 0.000 description 1
- DHBOWGIBEWRWHO-UHFFFAOYSA-N 8-(1,1,1,3,3,3-hexafluoropropan-2-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C(F)(F)F)C(F)(F)F)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 DHBOWGIBEWRWHO-UHFFFAOYSA-N 0.000 description 1
- CLYLULNPNSXMSZ-UHFFFAOYSA-N 8-(1,1,1,3,3,3-hexafluoropropan-2-yl)-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)N2C(C(F)(F)F)C(F)(F)F)C2=N1 CLYLULNPNSXMSZ-UHFFFAOYSA-N 0.000 description 1
- QDISXKAYRMCAST-UHFFFAOYSA-N 8-(1,1-diphenylpropan-2-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 QDISXKAYRMCAST-UHFFFAOYSA-N 0.000 description 1
- ZJNVFMAWBQDWTK-UHFFFAOYSA-N 8-(1,1-diphenylpropan-2-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 ZJNVFMAWBQDWTK-UHFFFAOYSA-N 0.000 description 1
- MQFIMDKNGBYMGK-UHFFFAOYSA-N 8-(1,1-diphenylpropan-2-yl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 MQFIMDKNGBYMGK-UHFFFAOYSA-N 0.000 description 1
- GXWMMMWGEPUUJK-UHFFFAOYSA-N 8-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4CCCCC4CC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 GXWMMMWGEPUUJK-UHFFFAOYSA-N 0.000 description 1
- ACKMNQRWBHZVRI-UHFFFAOYSA-N 8-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4CCCCC4CC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 ACKMNQRWBHZVRI-UHFFFAOYSA-N 0.000 description 1
- GNGATOMHMYDPIE-UHFFFAOYSA-N 8-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-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)N2C3CC4CCCCC4CC3)C2=N1 GNGATOMHMYDPIE-UHFFFAOYSA-N 0.000 description 1
- VIONUPVCYQMQRJ-UHFFFAOYSA-N 8-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)-2-anilinopyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4CCCCC4CC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 VIONUPVCYQMQRJ-UHFFFAOYSA-N 0.000 description 1
- GAMMJQVDJURENG-UHFFFAOYSA-N 8-(1,2-dihydroacenaphthylen-1-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C=4C=CC=C5C=CC=C(C=45)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 GAMMJQVDJURENG-UHFFFAOYSA-N 0.000 description 1
- GRHPQWXRVDQNOD-UHFFFAOYSA-N 8-(1,2-dihydroacenaphthylen-1-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C=4C=CC=C5C=CC=C(C=45)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 GRHPQWXRVDQNOD-UHFFFAOYSA-N 0.000 description 1
- MVILWIVBWCZDML-UHFFFAOYSA-N 8-(1,2-dihydroacenaphthylen-1-yl)-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)N2C3C=4C=CC=C5C=CC=C(C=45)C3)C2=N1 MVILWIVBWCZDML-UHFFFAOYSA-N 0.000 description 1
- ZRXSRNUXIFJRSK-UHFFFAOYSA-N 8-(1,3-benzodioxol-5-ylmethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3C=C4OCOC4=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 ZRXSRNUXIFJRSK-UHFFFAOYSA-N 0.000 description 1
- DKBWPYMOPRSTAM-UHFFFAOYSA-N 8-(1,3-benzodioxol-5-ylmethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3C=C4OCOC4=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 DKBWPYMOPRSTAM-UHFFFAOYSA-N 0.000 description 1
- AIMSFVRFVWKUIH-UHFFFAOYSA-N 8-(1,3-diphenylpropyl)-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)N2C(CCC=3C=CC=CC=3)C=3C=CC=CC=3)C2=N1 AIMSFVRFVWKUIH-UHFFFAOYSA-N 0.000 description 1
- UVPSQVXJRUYADS-UHFFFAOYSA-N 8-(1,5-diphenoxypentan-3-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(CCOC=3C=CC=CC=3)CCOC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 UVPSQVXJRUYADS-UHFFFAOYSA-N 0.000 description 1
- XUESZXFDIZAHFV-UHFFFAOYSA-N 8-(1,5-diphenoxypentan-3-yl)-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)N2C(CCOC=3C=CC=CC=3)CCOC=3C=CC=CC=3)C2=N1 XUESZXFDIZAHFV-UHFFFAOYSA-N 0.000 description 1
- OLMMHCKHTIONRZ-UHFFFAOYSA-N 8-(1-cyclohexylethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C)C1CCCCC1 OLMMHCKHTIONRZ-UHFFFAOYSA-N 0.000 description 1
- AYNHJEOEYJFMJC-UHFFFAOYSA-N 8-(1-cyclohexylethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C)C1CCCCC1 AYNHJEOEYJFMJC-UHFFFAOYSA-N 0.000 description 1
- RNKDTEQEPDISSP-UHFFFAOYSA-N 8-(1-cyclohexylethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(C)C1CCCCC1 RNKDTEQEPDISSP-UHFFFAOYSA-N 0.000 description 1
- PDVHXBGYYJXGLI-UHFFFAOYSA-N 8-(1-cyclohexylpropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(CC)C1CCCCC1 PDVHXBGYYJXGLI-UHFFFAOYSA-N 0.000 description 1
- HJWRMFIPFOZNIK-UHFFFAOYSA-N 8-(1-cyclohexylpropyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(CC)C1CCCCC1 HJWRMFIPFOZNIK-UHFFFAOYSA-N 0.000 description 1
- YPYZVZFXOKVZRV-UHFFFAOYSA-N 8-(1-cyclohexylpropyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(CC)C1CCCCC1 YPYZVZFXOKVZRV-UHFFFAOYSA-N 0.000 description 1
- IXJBBYGRVYNNAB-UHFFFAOYSA-N 8-(1-methoxypropan-2-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)COC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 IXJBBYGRVYNNAB-UHFFFAOYSA-N 0.000 description 1
- QZMNQAFVSZPATD-UHFFFAOYSA-N 8-(1-methoxypropan-2-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)COC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 QZMNQAFVSZPATD-UHFFFAOYSA-N 0.000 description 1
- YYHVPCFOUCDKRL-UHFFFAOYSA-N 8-(1-methoxypropan-2-yl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)COC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 YYHVPCFOUCDKRL-UHFFFAOYSA-N 0.000 description 1
- VYFZQAUSVPFRSP-UHFFFAOYSA-N 8-(1-phenylheptyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(CCCCCC)C1=CC=CC=C1 VYFZQAUSVPFRSP-UHFFFAOYSA-N 0.000 description 1
- WAYOLCJJECDDJG-UHFFFAOYSA-N 8-(1-phenylheptyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(CCCCCC)C1=CC=CC=C1 WAYOLCJJECDDJG-UHFFFAOYSA-N 0.000 description 1
- OAYDLGMGFWEASU-UHFFFAOYSA-N 8-(1-phenylprop-2-ynyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C#C)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 OAYDLGMGFWEASU-UHFFFAOYSA-N 0.000 description 1
- JHLONDDTEFHLRX-UHFFFAOYSA-N 8-(1-phenylprop-2-ynyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C#C)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 JHLONDDTEFHLRX-UHFFFAOYSA-N 0.000 description 1
- WZGRYAYPTMNRQZ-UHFFFAOYSA-N 8-(1-phenylpropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(CC)C1=CC=CC=C1 WZGRYAYPTMNRQZ-UHFFFAOYSA-N 0.000 description 1
- SISDWJJUXYZYMY-UHFFFAOYSA-N 8-(1-phenylpropyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(CC)C1=CC=CC=C1 SISDWJJUXYZYMY-UHFFFAOYSA-N 0.000 description 1
- SSZQCWJJHDFHJQ-UHFFFAOYSA-N 8-(2,2,3,3,3-pentafluoropropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(F)(F)C(F)(F)F)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 SSZQCWJJHDFHJQ-UHFFFAOYSA-N 0.000 description 1
- OSCYMZPOYPRDGC-UHFFFAOYSA-N 8-(2,2,3,3,3-pentafluoropropyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(F)(F)C(F)(F)F)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 OSCYMZPOYPRDGC-UHFFFAOYSA-N 0.000 description 1
- YAKYUBQVHNNJTJ-UHFFFAOYSA-N 8-(2,3,3a,4,5,6,7,7a-octahydro-1h-inden-5-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4CCCC4CC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 YAKYUBQVHNNJTJ-UHFFFAOYSA-N 0.000 description 1
- IZLKRBUQVTZMKP-UHFFFAOYSA-N 8-(2,3,3a,4,5,6,7,7a-octahydro-1h-inden-5-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4CCCC4CC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 IZLKRBUQVTZMKP-UHFFFAOYSA-N 0.000 description 1
- JHMNBSGNAWIBFB-UHFFFAOYSA-N 8-(2,3,3a,4,5,6,7,7a-octahydro-1h-inden-5-yl)-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)N2C3CC4CCCC4CC3)C2=N1 JHMNBSGNAWIBFB-UHFFFAOYSA-N 0.000 description 1
- IXLWLGPZBSBJNE-UHFFFAOYSA-N 8-(2,3,3a,4,5,6,7,7a-octahydro-1h-inden-5-yl)-2-anilinopyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4CCCC4CC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 IXLWLGPZBSBJNE-UHFFFAOYSA-N 0.000 description 1
- FQWQAZRSOUBNIU-UHFFFAOYSA-N 8-(2,3-dihydro-1h-inden-1-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4CC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 FQWQAZRSOUBNIU-UHFFFAOYSA-N 0.000 description 1
- AKIWYPJPANQLNC-UHFFFAOYSA-N 8-(2,3-dihydro-1h-inden-1-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4CC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 AKIWYPJPANQLNC-UHFFFAOYSA-N 0.000 description 1
- GDGFQJUSBFLNGT-UHFFFAOYSA-N 8-(2,3-dihydro-1h-inden-1-yl)-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)N2C3C4=CC=CC=C4CC3)C2=N1 GDGFQJUSBFLNGT-UHFFFAOYSA-N 0.000 description 1
- FXVHUZRFZKDABT-UHFFFAOYSA-N 8-(2,3-dihydro-1h-inden-2-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4=CC=CC=C4C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 FXVHUZRFZKDABT-UHFFFAOYSA-N 0.000 description 1
- CSZUGECXFRUYCG-UHFFFAOYSA-N 8-(2,3-dihydro-1h-inden-2-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC4=CC=CC=C4C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 CSZUGECXFRUYCG-UHFFFAOYSA-N 0.000 description 1
- YMJYELIKFCOZGQ-UHFFFAOYSA-N 8-(2,3-dihydro-1h-inden-2-yl)-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)N2C3CC4=CC=CC=C4C3)C2=N1 YMJYELIKFCOZGQ-UHFFFAOYSA-N 0.000 description 1
- OOVOLGXKLVZGSH-UHFFFAOYSA-N 8-(2,3-dimethylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1C(C)CCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 OOVOLGXKLVZGSH-UHFFFAOYSA-N 0.000 description 1
- PCECIRVHKSJANR-UHFFFAOYSA-N 8-(2,3-dimethylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1C(C)CCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 PCECIRVHKSJANR-UHFFFAOYSA-N 0.000 description 1
- JTULOOYIYGTPAA-UHFFFAOYSA-N 8-(2,3-dimethylcyclohexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1C(C)CCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 JTULOOYIYGTPAA-UHFFFAOYSA-N 0.000 description 1
- BZZRGSJDHSYFRM-UHFFFAOYSA-N 8-(2,5-dimethylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 BZZRGSJDHSYFRM-UHFFFAOYSA-N 0.000 description 1
- NTYKZZUSGFHGFO-UHFFFAOYSA-N 8-(2,5-dimethylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 NTYKZZUSGFHGFO-UHFFFAOYSA-N 0.000 description 1
- HYLPXQXBRUWOAZ-UHFFFAOYSA-N 8-(2,5-dimethylcyclohexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 HYLPXQXBRUWOAZ-UHFFFAOYSA-N 0.000 description 1
- VMIBQNNCTFWNHC-UHFFFAOYSA-N 8-(2,6-dimethylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1CCCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 VMIBQNNCTFWNHC-UHFFFAOYSA-N 0.000 description 1
- AGINJMSSPGPMDH-UHFFFAOYSA-N 8-(2,6-dimethylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1CCCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 AGINJMSSPGPMDH-UHFFFAOYSA-N 0.000 description 1
- VURUAZBJYKGJNV-UHFFFAOYSA-N 8-(2,6-dimethylcyclohexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1CCCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 VURUAZBJYKGJNV-UHFFFAOYSA-N 0.000 description 1
- MPQJGMJRGUBVOF-UHFFFAOYSA-N 8-(2-adamantyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CC5CC(C4)CC3C5)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 MPQJGMJRGUBVOF-UHFFFAOYSA-N 0.000 description 1
- GVRCADQFGFVTQT-UHFFFAOYSA-N 8-(2-adamantyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CC5CC(C4)CC3C5)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 GVRCADQFGFVTQT-UHFFFAOYSA-N 0.000 description 1
- AXOLIIDOZRUMEB-UHFFFAOYSA-N 8-(2-adamantyl)-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)N2C3C4CC5CC(C4)CC3C5)C2=N1 AXOLIIDOZRUMEB-UHFFFAOYSA-N 0.000 description 1
- DNZOWQPRTWYYGJ-UHFFFAOYSA-N 8-(2-adamantyl)-2-anilinopyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CC5CC(C4)CC3C5)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 DNZOWQPRTWYYGJ-UHFFFAOYSA-N 0.000 description 1
- ZSYNOQZOIGUCPN-UHFFFAOYSA-N 8-(2-butoxyethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCCCC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 ZSYNOQZOIGUCPN-UHFFFAOYSA-N 0.000 description 1
- FGBKOCSOZJMKQD-UHFFFAOYSA-N 8-(2-butoxyethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCCCC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 FGBKOCSOZJMKQD-UHFFFAOYSA-N 0.000 description 1
- HGNJVFJYZVLFJK-UHFFFAOYSA-N 8-(2-butoxyethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCCCC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 HGNJVFJYZVLFJK-UHFFFAOYSA-N 0.000 description 1
- RXKKXPYMEWTWMX-UHFFFAOYSA-N 8-(2-cyclopropylethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCC3CC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 RXKKXPYMEWTWMX-UHFFFAOYSA-N 0.000 description 1
- PUTYWTVOVLEQTN-UHFFFAOYSA-N 8-(2-cyclopropylethyl)-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)N2CCC3CC3)C2=N1 PUTYWTVOVLEQTN-UHFFFAOYSA-N 0.000 description 1
- IGVJERUOAUTNGJ-UHFFFAOYSA-N 8-(2-ethoxyethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 IGVJERUOAUTNGJ-UHFFFAOYSA-N 0.000 description 1
- HCIZWWPHLDFWGN-UHFFFAOYSA-N 8-(2-ethoxyethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 HCIZWWPHLDFWGN-UHFFFAOYSA-N 0.000 description 1
- OJAMKOCOTZETGF-UHFFFAOYSA-N 8-(2-ethoxyethyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 OJAMKOCOTZETGF-UHFFFAOYSA-N 0.000 description 1
- BQBGLAGWANFKLG-UHFFFAOYSA-N 8-(2-ethylhexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(CC)CCCC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 BQBGLAGWANFKLG-UHFFFAOYSA-N 0.000 description 1
- AZGZWQWJUKAYFM-UHFFFAOYSA-N 8-(2-ethylhexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(CC)CCCC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 AZGZWQWJUKAYFM-UHFFFAOYSA-N 0.000 description 1
- CIEZKVJQAOTTIM-UHFFFAOYSA-N 8-(2-ethylhexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(CC)CCCC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 CIEZKVJQAOTTIM-UHFFFAOYSA-N 0.000 description 1
- CKQCLDWOKXSJEU-UHFFFAOYSA-N 8-(2-methyl-3-oxobutyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(C)C(C)=O)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 CKQCLDWOKXSJEU-UHFFFAOYSA-N 0.000 description 1
- HMOPZAWYKCYORQ-UHFFFAOYSA-N 8-(2-methyl-3-oxobutyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(C)C(C)=O)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 HMOPZAWYKCYORQ-UHFFFAOYSA-N 0.000 description 1
- XKGWHAZRTYMYOP-UHFFFAOYSA-N 8-(2-methyl-3-oxobutyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC(C)C(C)=O)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 XKGWHAZRTYMYOP-UHFFFAOYSA-N 0.000 description 1
- IVUPOTALVYYUOW-UHFFFAOYSA-N 8-(2-methyl-5-propan-2-ylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C(C)C)CCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 IVUPOTALVYYUOW-UHFFFAOYSA-N 0.000 description 1
- IFQPHZUFECWFGY-UHFFFAOYSA-N 8-(2-methyl-5-propan-2-ylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C(C)C)CCC(C)C1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 IFQPHZUFECWFGY-UHFFFAOYSA-N 0.000 description 1
- ZVRPFFOHEGJBKM-UHFFFAOYSA-N 8-(2-methylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 ZVRPFFOHEGJBKM-UHFFFAOYSA-N 0.000 description 1
- COLDOMWNPWDZBV-UHFFFAOYSA-N 8-(2-methylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 COLDOMWNPWDZBV-UHFFFAOYSA-N 0.000 description 1
- LFSZDGYSRXJMPY-UHFFFAOYSA-N 8-(2-methylcyclohexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 LFSZDGYSRXJMPY-UHFFFAOYSA-N 0.000 description 1
- LEDXDJTWZQQWBE-UHFFFAOYSA-N 8-(2-naphthalen-2-ylethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCC=3C=C4C=CC=CC4=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 LEDXDJTWZQQWBE-UHFFFAOYSA-N 0.000 description 1
- ZOCOPZSWSPVRHX-UHFFFAOYSA-N 8-(2-naphthalen-2-ylethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCC=3C=C4C=CC=CC4=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 ZOCOPZSWSPVRHX-UHFFFAOYSA-N 0.000 description 1
- LDUBPDVZZWQLTC-UHFFFAOYSA-N 8-(2-oxocyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 LDUBPDVZZWQLTC-UHFFFAOYSA-N 0.000 description 1
- HTQDHRAVLYXSHN-UHFFFAOYSA-N 8-(2-oxocyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 HTQDHRAVLYXSHN-UHFFFAOYSA-N 0.000 description 1
- DACYXRRNAYUGAD-UHFFFAOYSA-N 8-(2-phenoxyethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCOC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 DACYXRRNAYUGAD-UHFFFAOYSA-N 0.000 description 1
- RTHQEQOJVPSIKT-UHFFFAOYSA-N 8-(2-phenoxyethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCOC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 RTHQEQOJVPSIKT-UHFFFAOYSA-N 0.000 description 1
- YZTPUPHYAXZBHW-UHFFFAOYSA-N 8-(2-phenyl-1,3-dioxan-5-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3COC(OC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 YZTPUPHYAXZBHW-UHFFFAOYSA-N 0.000 description 1
- YHONVLLSQUCJAB-UHFFFAOYSA-N 8-(2-phenyl-1,3-dioxan-5-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3COC(OC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 YHONVLLSQUCJAB-UHFFFAOYSA-N 0.000 description 1
- XUVYYAYKVFFWTM-UHFFFAOYSA-N 8-(2-phenylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C(CCCC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 XUVYYAYKVFFWTM-UHFFFAOYSA-N 0.000 description 1
- XEYQWUOXLWVIFR-UHFFFAOYSA-N 8-(2-phenylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C(CCCC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 XEYQWUOXLWVIFR-UHFFFAOYSA-N 0.000 description 1
- ARWINMXYGFGEHH-UHFFFAOYSA-N 8-(2-propan-2-ylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC(C)C1CCCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 ARWINMXYGFGEHH-UHFFFAOYSA-N 0.000 description 1
- NSSDGPWHYKHZRP-UHFFFAOYSA-N 8-(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-2-methyloctan-2-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)(C)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 NSSDGPWHYKHZRP-UHFFFAOYSA-N 0.000 description 1
- FTYZHADMCRRXMV-UHFFFAOYSA-N 8-(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-2-methyloctan-2-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)(C)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 FTYZHADMCRRXMV-UHFFFAOYSA-N 0.000 description 1
- JCFZCXHESHWXPC-UHFFFAOYSA-N 8-(3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-2-methyloctan-2-yl)-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)N2C(C)(C)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F)C2=N1 JCFZCXHESHWXPC-UHFFFAOYSA-N 0.000 description 1
- AGSLLELYOAXSIH-UHFFFAOYSA-N 8-(3,3-dimethylbutyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCC(C)(C)C)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 AGSLLELYOAXSIH-UHFFFAOYSA-N 0.000 description 1
- FMXZPYWIYQLLLB-UHFFFAOYSA-N 8-(3,3-dimethylbutyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCC(C)(C)C)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 FMXZPYWIYQLLLB-UHFFFAOYSA-N 0.000 description 1
- SJRCYEAIKCJCCY-UHFFFAOYSA-N 8-(3,3-dimethylbutyl)-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)N2CCC(C)(C)C)C2=N1 SJRCYEAIKCJCCY-UHFFFAOYSA-N 0.000 description 1
- IVGNCRPCZSWTHY-UHFFFAOYSA-N 8-(3,5-dimethylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 IVGNCRPCZSWTHY-UHFFFAOYSA-N 0.000 description 1
- IWDVLWKJFQBHMC-UHFFFAOYSA-N 8-(3,5-dimethylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 IWDVLWKJFQBHMC-UHFFFAOYSA-N 0.000 description 1
- PMZVTBOHARMJRE-UHFFFAOYSA-N 8-(3,5-dimethylcyclohexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 PMZVTBOHARMJRE-UHFFFAOYSA-N 0.000 description 1
- JDZFLBRHCZITEI-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-(3,4-difluoroanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(F)C(F)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4CCC(C4)C3)C2=N1 JDZFLBRHCZITEI-UHFFFAOYSA-N 0.000 description 1
- ITTWCBFWEUEKCC-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-2-[4-(1,1,2,2-tetrafluoroethoxy)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC(F)(F)C(F)F)=CC=C1NC1=NC=C(C=CC(=O)N2C3C4CCC(C4)C3)C2=N1 ITTWCBFWEUEKCC-UHFFFAOYSA-N 0.000 description 1
- YHYAOMISKKOOKT-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanyl)-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)N2C3C4CCC(C4)C3)C2=N1 YHYAOMISKKOOKT-UHFFFAOYSA-N 0.000 description 1
- BRVDPKZZGVKAOP-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanylmethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3C4CCC(C4)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 BRVDPKZZGVKAOP-UHFFFAOYSA-N 0.000 description 1
- LNXBLSPMAMMWGT-UHFFFAOYSA-N 8-(3-bicyclo[2.2.1]heptanylmethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3C4CCC(C4)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 LNXBLSPMAMMWGT-UHFFFAOYSA-N 0.000 description 1
- NGEFDZDNLQGAEW-UHFFFAOYSA-N 8-(3-methoxypropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCCOC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 NGEFDZDNLQGAEW-UHFFFAOYSA-N 0.000 description 1
- MQTMRYNJUUOYMS-UHFFFAOYSA-N 8-(3-methoxypropyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCCOC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 MQTMRYNJUUOYMS-UHFFFAOYSA-N 0.000 description 1
- KUSFWWGHWLEFAU-UHFFFAOYSA-N 8-(3-methoxypropyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCCOC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 KUSFWWGHWLEFAU-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- WQLZIMMSPKTJFE-UHFFFAOYSA-N 8-(3-methylbut-2-enyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC=C(C)C)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 WQLZIMMSPKTJFE-UHFFFAOYSA-N 0.000 description 1
- GBUXZMVGZUZONW-UHFFFAOYSA-N 8-(3-methylbut-2-enyl)-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)N2CC=C(C)C)C2=N1 GBUXZMVGZUZONW-UHFFFAOYSA-N 0.000 description 1
- QWYJVVBXVWZSMK-UHFFFAOYSA-N 8-(3-methylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 QWYJVVBXVWZSMK-UHFFFAOYSA-N 0.000 description 1
- QWEKOHKDNAFNLG-UHFFFAOYSA-N 8-(3-methylcyclohexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CCCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 QWEKOHKDNAFNLG-UHFFFAOYSA-N 0.000 description 1
- OXESOFRNMMYLIE-UHFFFAOYSA-N 8-(3-phenylprop-2-ynyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC#CC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 OXESOFRNMMYLIE-UHFFFAOYSA-N 0.000 description 1
- GBUMLOVUUPIRMX-UHFFFAOYSA-N 8-(3-phenylprop-2-ynyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC#CC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 GBUMLOVUUPIRMX-UHFFFAOYSA-N 0.000 description 1
- YSZXDQZBDTUFLS-UHFFFAOYSA-N 8-(4-butan-2-ylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)CC)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 YSZXDQZBDTUFLS-UHFFFAOYSA-N 0.000 description 1
- AKPITXSBVKIPIS-UHFFFAOYSA-N 8-(4-butan-2-ylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)CC)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 AKPITXSBVKIPIS-UHFFFAOYSA-N 0.000 description 1
- OCUUGQKYXQFCFG-UHFFFAOYSA-N 8-(4-butan-2-ylcyclohexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)CC)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 OCUUGQKYXQFCFG-UHFFFAOYSA-N 0.000 description 1
- CXCZBLZWXBGUID-UHFFFAOYSA-N 8-(4-cyclohexylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCC(CC3)C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 CXCZBLZWXBGUID-UHFFFAOYSA-N 0.000 description 1
- WGIAJJDHPIOJOF-UHFFFAOYSA-N 8-(4-cyclohexylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCC(CC3)C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 WGIAJJDHPIOJOF-UHFFFAOYSA-N 0.000 description 1
- JHIRADMPYKOFHH-UHFFFAOYSA-N 8-(4-cyclohexylcyclohexyl)-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)N2C3CCC(CC3)C3CCCCC3)C2=N1 JHIRADMPYKOFHH-UHFFFAOYSA-N 0.000 description 1
- OVTCIMQKMDTVSZ-UHFFFAOYSA-N 8-(4-methylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 OVTCIMQKMDTVSZ-UHFFFAOYSA-N 0.000 description 1
- RKFUWCBMTFQEMI-UHFFFAOYSA-N 8-(4-methylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 RKFUWCBMTFQEMI-UHFFFAOYSA-N 0.000 description 1
- IBZDMVUWHXHCPS-UHFFFAOYSA-N 8-(4-methylcyclohexyl)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 IBZDMVUWHXHCPS-UHFFFAOYSA-N 0.000 description 1
- KNFHWCKHUFIFGL-UHFFFAOYSA-N 8-(4-propan-2-ylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 KNFHWCKHUFIFGL-UHFFFAOYSA-N 0.000 description 1
- RAIFXGVBLGQKEM-UHFFFAOYSA-N 8-(4-tert-butylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)(C)C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 RAIFXGVBLGQKEM-UHFFFAOYSA-N 0.000 description 1
- ZFUWMYTXNRPTES-UHFFFAOYSA-N 8-(4-tert-butylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)(C)C)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 ZFUWMYTXNRPTES-UHFFFAOYSA-N 0.000 description 1
- QUNSIRPKDWVFGH-UHFFFAOYSA-N 8-(4-tert-butylcyclohexyl)-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)N2C3CCC(CC3)C(C)(C)C)C2=N1 QUNSIRPKDWVFGH-UHFFFAOYSA-N 0.000 description 1
- INLLJJXPUDAZSH-UHFFFAOYSA-N 8-(5-bicyclo[2.2.1]hept-2-enyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CC(C=C4)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 INLLJJXPUDAZSH-UHFFFAOYSA-N 0.000 description 1
- XIBYZPPTUCXCMY-UHFFFAOYSA-N 8-(5-bicyclo[2.2.1]hept-2-enyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4CC(C=C4)C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 XIBYZPPTUCXCMY-UHFFFAOYSA-N 0.000 description 1
- UMNOZTLYQXCSPD-UHFFFAOYSA-N 8-(5-bicyclo[2.2.1]hept-2-enyl)-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)N2C3C4CC(C=C4)C3)C2=N1 UMNOZTLYQXCSPD-UHFFFAOYSA-N 0.000 description 1
- GRPFZQQDEKSDGR-UHFFFAOYSA-N 8-(5-methyl-2-propan-2-ylcyclohexyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC(C)C1CCC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 GRPFZQQDEKSDGR-UHFFFAOYSA-N 0.000 description 1
- YYNYYEIQWRRXNR-UHFFFAOYSA-N 8-(5-methyl-2-propan-2-ylcyclohexyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC(C)C1CCC(C)CC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 YYNYYEIQWRRXNR-UHFFFAOYSA-N 0.000 description 1
- GYOATJWUAJKWOL-UHFFFAOYSA-N 8-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4CCC4=CC=CC=C43)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 GYOATJWUAJKWOL-UHFFFAOYSA-N 0.000 description 1
- XTQQKFFJWVGIDH-UHFFFAOYSA-N 8-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4CCC4=CC=CC=C43)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 XTQQKFFJWVGIDH-UHFFFAOYSA-N 0.000 description 1
- AYVPXUUKKITCOV-UHFFFAOYSA-N 8-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-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)N2C3C4=CC=CC=C4CCC4=CC=CC=C43)C2=N1 AYVPXUUKKITCOV-UHFFFAOYSA-N 0.000 description 1
- LEQXSLUWMKGZMG-UHFFFAOYSA-N 8-(9h-fluoren-9-yl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4C4=CC=CC=C43)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 LEQXSLUWMKGZMG-UHFFFAOYSA-N 0.000 description 1
- MZNZAWDRUWRUJO-UHFFFAOYSA-N 8-(9h-fluoren-9-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C4=CC=CC=C4C4=CC=CC=C43)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 MZNZAWDRUWRUJO-UHFFFAOYSA-N 0.000 description 1
- TUPQDVWLJIZDCW-UHFFFAOYSA-N 8-(9h-fluoren-9-yl)-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)N2C3C4=CC=CC=C4C4=CC=CC=C43)C2=N1 TUPQDVWLJIZDCW-UHFFFAOYSA-N 0.000 description 1
- XPTBMKFPJSFIJE-UHFFFAOYSA-N 8-(cyclohex-3-en-1-ylmethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3CC=CCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 XPTBMKFPJSFIJE-UHFFFAOYSA-N 0.000 description 1
- AGJXJOGDNJOLBF-UHFFFAOYSA-N 8-(cyclohex-3-en-1-ylmethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3CC=CCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 AGJXJOGDNJOLBF-UHFFFAOYSA-N 0.000 description 1
- LMPDCSDXKPERQO-UHFFFAOYSA-N 8-(cyclohex-3-en-1-ylmethyl)-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)N2CC3CC=CCC3)C2=N1 LMPDCSDXKPERQO-UHFFFAOYSA-N 0.000 description 1
- TYKSBSXDPOCVBN-UHFFFAOYSA-N 8-(cyclohexylmethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 TYKSBSXDPOCVBN-UHFFFAOYSA-N 0.000 description 1
- AYZXHQWCZJBUNI-UHFFFAOYSA-N 8-(cyclohexylmethyl)-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)N2CC3CCCCC3)C2=N1 AYZXHQWCZJBUNI-UHFFFAOYSA-N 0.000 description 1
- FEJBJGXFPKZKOT-UHFFFAOYSA-N 8-(dicyclohexylmethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C3CCCCC3)C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 FEJBJGXFPKZKOT-UHFFFAOYSA-N 0.000 description 1
- FAIGXIPDHWGYHQ-UHFFFAOYSA-N 8-(dicyclohexylmethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C3CCCCC3)C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 FAIGXIPDHWGYHQ-UHFFFAOYSA-N 0.000 description 1
- FGUSWTXPMKRNCA-UHFFFAOYSA-N 8-(dicyclohexylmethyl)-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)N2C(C3CCCCC3)C3CCCCC3)C2=N1 FGUSWTXPMKRNCA-UHFFFAOYSA-N 0.000 description 1
- RZKNUMOAGIUCSX-UHFFFAOYSA-N 8-(furan-2-ylmethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3OC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 RZKNUMOAGIUCSX-UHFFFAOYSA-N 0.000 description 1
- KBWKSSMTWABNNH-UHFFFAOYSA-N 8-(furan-2-ylmethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3OC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 KBWKSSMTWABNNH-UHFFFAOYSA-N 0.000 description 1
- UASPBEHFGLMJSB-UHFFFAOYSA-N 8-(furan-2-ylmethyl)-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)N2CC=3OC=CC=3)C2=N1 UASPBEHFGLMJSB-UHFFFAOYSA-N 0.000 description 1
- OCQROIHIYCJBAN-UHFFFAOYSA-N 8-(furan-3-ylmethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3=COC=C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 OCQROIHIYCJBAN-UHFFFAOYSA-N 0.000 description 1
- CGRMYLWRLCIGIZ-UHFFFAOYSA-N 8-(furan-3-ylmethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3=COC=C3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 CGRMYLWRLCIGIZ-UHFFFAOYSA-N 0.000 description 1
- QNNKSGDDKWCKDV-UHFFFAOYSA-N 8-(furan-3-ylmethyl)-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)N2CC3=COC=C3)C2=N1 QNNKSGDDKWCKDV-UHFFFAOYSA-N 0.000 description 1
- RSJKWGPLQPFVDA-UHFFFAOYSA-N 8-(oxan-4-yl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCOCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 RSJKWGPLQPFVDA-UHFFFAOYSA-N 0.000 description 1
- IJFOTXYRIFTUAC-UHFFFAOYSA-N 8-(oxolan-2-ylmethyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3OCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 IJFOTXYRIFTUAC-UHFFFAOYSA-N 0.000 description 1
- KTZRHVBOPAEJJJ-UHFFFAOYSA-N 8-(oxolan-2-ylmethyl)-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3OCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 KTZRHVBOPAEJJJ-UHFFFAOYSA-N 0.000 description 1
- HXZSGQYWAFJCRA-UHFFFAOYSA-N 8-[(2-methyl-3-bicyclo[2.2.1]heptanyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1C(C2)CCC2C1CN(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1CCCCC1 HXZSGQYWAFJCRA-UHFFFAOYSA-N 0.000 description 1
- AEKZKJHTQKUHPP-UHFFFAOYSA-N 8-[(2-methyl-3-bicyclo[2.2.1]heptanyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1C(C2)CCC2C1CN(C(C=CC1=CN=2)=O)C1=NC=2NC(C=C1)=CC=C1N1CCN(C)CC1 AEKZKJHTQKUHPP-UHFFFAOYSA-N 0.000 description 1
- CUFKGDUTUYLVIY-UHFFFAOYSA-N 8-[(2-methylphenyl)-phenylmethyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=CC=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21)=O)C1=CC=CC=C1 CUFKGDUTUYLVIY-UHFFFAOYSA-N 0.000 description 1
- ZLWRLJBOQFBDCS-UHFFFAOYSA-N 8-[(2-methylphenyl)-phenylmethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=CC=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21)=O)C1=CC=CC=C1 ZLWRLJBOQFBDCS-UHFFFAOYSA-N 0.000 description 1
- GPEFUOQRFOXDID-UHFFFAOYSA-N 8-[(2-methylphenyl)-phenylmethyl]-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)N2C(C=3C=CC=CC=3)C=3C(=CC=CC=3)C)C2=N1 GPEFUOQRFOXDID-UHFFFAOYSA-N 0.000 description 1
- WRUUYLJFUYEVQX-UHFFFAOYSA-N 8-[(3,5-dimethoxyphenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC(OC)=CC(CN2C(C=CC3=CN=C(NC=4C=CC(=CC=4)N4CCCCC4)N=C32)=O)=C1 WRUUYLJFUYEVQX-UHFFFAOYSA-N 0.000 description 1
- JWLZSCCACRRWBM-UHFFFAOYSA-N 8-[(3,5-dimethoxyphenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC(OC)=CC(CN2C(C=CC3=CN=C(NC=4C=CC(=CC=4)N4N=CC=C4)N=C32)=O)=C1 JWLZSCCACRRWBM-UHFFFAOYSA-N 0.000 description 1
- LFGXFHNCXQLHDZ-UHFFFAOYSA-N 8-[(3,5-dimethoxyphenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC(OC)=CC(CN2C(C=CC3=CN=C(NC=4C=CC(=CC=4)N4CCN(C)CC4)N=C32)=O)=C1 LFGXFHNCXQLHDZ-UHFFFAOYSA-N 0.000 description 1
- ZMSIICZPHPXMTF-UHFFFAOYSA-N 8-[(3-ethyloxetan-3-yl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1CC1(CC)COC1 ZMSIICZPHPXMTF-UHFFFAOYSA-N 0.000 description 1
- NFXJXKYPUMYSOY-UHFFFAOYSA-N 8-[(3-ethyloxetan-3-yl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1CC1(CC)COC1 NFXJXKYPUMYSOY-UHFFFAOYSA-N 0.000 description 1
- DDZOYTQOMDDAGR-UHFFFAOYSA-N 8-[(3-methylphenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=CC=CC(CN2C(C=CC3=CN=C(NC=4C=CC(=CC=4)N4CCCCC4)N=C32)=O)=C1 DDZOYTQOMDDAGR-UHFFFAOYSA-N 0.000 description 1
- NZFXIRIRKGVOSB-UHFFFAOYSA-N 8-[(3-methylphenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=CC=CC(CN2C(C=CC3=CN=C(NC=4C=CC(=CC=4)N4N=CC=C4)N=C32)=O)=C1 NZFXIRIRKGVOSB-UHFFFAOYSA-N 0.000 description 1
- IVUWQSAWZJPAJR-UHFFFAOYSA-N 8-[(3-methylphenyl)methyl]-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)N2CC=3C=C(C)C=CC=3)C2=N1 IVUWQSAWZJPAJR-UHFFFAOYSA-N 0.000 description 1
- MNPNMJOGKSBKLP-UHFFFAOYSA-N 8-[(3-phenoxyphenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC=3C=C(OC=4C=CC=CC=4)C=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 MNPNMJOGKSBKLP-UHFFFAOYSA-N 0.000 description 1
- SRWQUKLZZORHLW-UHFFFAOYSA-N 8-[(4-chloro-2-nitrophenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 SRWQUKLZZORHLW-UHFFFAOYSA-N 0.000 description 1
- GATIUBZLXKYHLK-UHFFFAOYSA-N 8-[(4-chloro-2-nitrophenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 GATIUBZLXKYHLK-UHFFFAOYSA-N 0.000 description 1
- QIIIDNTWTLZUJH-UHFFFAOYSA-N 8-[(4-chloro-2-nitrophenyl)methyl]-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)N2CC=3C(=CC(Cl)=CC=3)[N+]([O-])=O)C2=N1 QIIIDNTWTLZUJH-UHFFFAOYSA-N 0.000 description 1
- BPRPQFROLRCGHU-UHFFFAOYSA-N 8-[(4-ethylphenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(CC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 BPRPQFROLRCGHU-UHFFFAOYSA-N 0.000 description 1
- ASTHUTGVPDKQEN-UHFFFAOYSA-N 8-[(4-ethylphenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(CC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 ASTHUTGVPDKQEN-UHFFFAOYSA-N 0.000 description 1
- OOCKUWXGDOYEKH-UHFFFAOYSA-N 8-[(4-ethylphenyl)methyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(CC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 OOCKUWXGDOYEKH-UHFFFAOYSA-N 0.000 description 1
- HPHMCPHIBBYHKP-UHFFFAOYSA-N 8-[(4-methoxyphenyl)-pyridin-2-ylmethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21)=O)C1=CC=CC=N1 HPHMCPHIBBYHKP-UHFFFAOYSA-N 0.000 description 1
- ZUKLFBZWUYTGMO-UHFFFAOYSA-N 8-[(4-methoxyphenyl)-pyridin-2-ylmethyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21)=O)C1=CC=CC=N1 ZUKLFBZWUYTGMO-UHFFFAOYSA-N 0.000 description 1
- JRAJORAHSBQCOT-UHFFFAOYSA-N 8-[(4-methylphenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 JRAJORAHSBQCOT-UHFFFAOYSA-N 0.000 description 1
- CDSKMEYAQWRSJP-UHFFFAOYSA-N 8-[(4-methylphenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 CDSKMEYAQWRSJP-UHFFFAOYSA-N 0.000 description 1
- MIZFPLLXGZZUOI-UHFFFAOYSA-N 8-[(4-methylphenyl)methyl]-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)N2CC=3C=CC(C)=CC=3)C2=N1 MIZFPLLXGZZUOI-UHFFFAOYSA-N 0.000 description 1
- SVRYQPGGSDVRRB-UHFFFAOYSA-N 8-[(4-methylsulfanylphenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(SC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 SVRYQPGGSDVRRB-UHFFFAOYSA-N 0.000 description 1
- MIXPIFVFAMJFQQ-UHFFFAOYSA-N 8-[(4-methylsulfanylphenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(SC)=CC=C1CN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 MIXPIFVFAMJFQQ-UHFFFAOYSA-N 0.000 description 1
- KWOCHSBAUFQGLH-UHFFFAOYSA-N 8-[1-(2-bromophenyl)ethyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C)C1=CC=CC=C1Br KWOCHSBAUFQGLH-UHFFFAOYSA-N 0.000 description 1
- IBRIJHMILLKFFC-UHFFFAOYSA-N 8-[1-(2-bromophenyl)ethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C)C1=CC=CC=C1Br IBRIJHMILLKFFC-UHFFFAOYSA-N 0.000 description 1
- GVRMIFDZWIVEPW-UHFFFAOYSA-N 8-[1-(2-bromophenyl)ethyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(C)C1=CC=CC=C1Br GVRMIFDZWIVEPW-UHFFFAOYSA-N 0.000 description 1
- LBGWUAQZSPATNA-UHFFFAOYSA-N 8-[1-(3,4-dichlorophenyl)ethyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C)C1=CC=C(Cl)C(Cl)=C1 LBGWUAQZSPATNA-UHFFFAOYSA-N 0.000 description 1
- ITRZWTCXLZWWLI-UHFFFAOYSA-N 8-[1-(3,4-dichlorophenyl)ethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C)C1=CC=C(Cl)C(Cl)=C1 ITRZWTCXLZWWLI-UHFFFAOYSA-N 0.000 description 1
- UOMWFCYNSXBRRU-UHFFFAOYSA-N 8-[1-(3,4-dichlorophenyl)ethyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(C)C1=CC=C(Cl)C(Cl)=C1 UOMWFCYNSXBRRU-UHFFFAOYSA-N 0.000 description 1
- JQQDAKOCAZIORP-UHFFFAOYSA-N 8-[1-(4-methoxyphenyl)ethyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C(C)N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 JQQDAKOCAZIORP-UHFFFAOYSA-N 0.000 description 1
- IHOPAZRVGQYQQE-UHFFFAOYSA-N 8-[1-(4-methoxyphenyl)ethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C(C)N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 IHOPAZRVGQYQQE-UHFFFAOYSA-N 0.000 description 1
- BYMGXSHSYCWXPL-UHFFFAOYSA-N 8-[1-(4-methoxyphenyl)ethyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C(C)N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 BYMGXSHSYCWXPL-UHFFFAOYSA-N 0.000 description 1
- UMVNTMKQTJUMDE-UHFFFAOYSA-N 8-[1-(4-methylphenyl)ethyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C)C1=CC=C(C)C=C1 UMVNTMKQTJUMDE-UHFFFAOYSA-N 0.000 description 1
- LWZSKPKUDAFXGG-UHFFFAOYSA-N 8-[1-(4-methylphenyl)ethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C)C1=CC=C(C)C=C1 LWZSKPKUDAFXGG-UHFFFAOYSA-N 0.000 description 1
- RGQGXEAMWZOPIR-UHFFFAOYSA-N 8-[1-(4-methylphenyl)ethyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=NC=C2C=CC(=O)N1C(C)C1=CC=C(C)C=C1 RGQGXEAMWZOPIR-UHFFFAOYSA-N 0.000 description 1
- VSQABOFDQHBVNQ-UHFFFAOYSA-N 8-[1-(4-phenylphenyl)ethyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C=CC(=O)N1C(C)C(C=C1)=CC=C1C1=CC=CC=C1 VSQABOFDQHBVNQ-UHFFFAOYSA-N 0.000 description 1
- BVBONUSBYKMOPH-UHFFFAOYSA-N 8-[1-(4-phenylphenyl)ethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3N=CC=C3)=NC=C2C=CC(=O)N1C(C)C(C=C1)=CC=C1C1=CC=CC=C1 BVBONUSBYKMOPH-UHFFFAOYSA-N 0.000 description 1
- ZRCLOFOWXJWQQY-UHFFFAOYSA-N 8-[2-(2-methoxyethoxy)ethyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCCOC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 ZRCLOFOWXJWQQY-UHFFFAOYSA-N 0.000 description 1
- SOKIKIDJCMBJBL-UHFFFAOYSA-N 8-[2-(2-methoxyethoxy)ethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCCOC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 SOKIKIDJCMBJBL-UHFFFAOYSA-N 0.000 description 1
- CNPYTAYJSKAPLX-UHFFFAOYSA-N 8-[2-(2-methoxyethoxy)ethyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CCOCCOC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 CNPYTAYJSKAPLX-UHFFFAOYSA-N 0.000 description 1
- JKPYQWUZDHMVFA-UHFFFAOYSA-N 8-[2-(4-tert-butylphenoxy)ethyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C(C)(C)C)=CC=C1OCCN1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 JKPYQWUZDHMVFA-UHFFFAOYSA-N 0.000 description 1
- ASXLRUZYVJLAOS-UHFFFAOYSA-N 8-[2-(4-tert-butylphenoxy)ethyl]-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)N2CCOC=3C=CC(=CC=3)C(C)(C)C)C2=N1 ASXLRUZYVJLAOS-UHFFFAOYSA-N 0.000 description 1
- OFMZGBVEBJBMCL-UHFFFAOYSA-N 8-[2-[tert-butyl(dimethyl)silyl]oxycyclopentyl]-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(SC)=NC=C2C=CC(=O)N1C1CCCC1O[Si](C)(C)C(C)(C)C OFMZGBVEBJBMCL-UHFFFAOYSA-N 0.000 description 1
- HGTBEQTUWBISCD-UHFFFAOYSA-N 8-[2-[tert-butyl(dimethyl)silyl]oxycyclopentyl]-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=CC(=O)N1C1CCCC1O[Si](C)(C)C(C)(C)C HGTBEQTUWBISCD-UHFFFAOYSA-N 0.000 description 1
- IHFKMOQPZJNALK-UHFFFAOYSA-N 8-[4-(2-methylbutan-2-yl)cyclohexyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)(C)CC)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21 IHFKMOQPZJNALK-UHFFFAOYSA-N 0.000 description 1
- ATKBVIFJWHNLAK-UHFFFAOYSA-N 8-[4-(2-methylbutan-2-yl)cyclohexyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)(C)CC)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21 ATKBVIFJWHNLAK-UHFFFAOYSA-N 0.000 description 1
- FVSOHUNCTHRBEW-UHFFFAOYSA-N 8-[4-(2-methylbutan-2-yl)cyclohexyl]-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CC(C(C)(C)CC)CCC1N1C(=O)C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=C21 FVSOHUNCTHRBEW-UHFFFAOYSA-N 0.000 description 1
- DASRMIKJLWLNIA-UHFFFAOYSA-N 8-[bis(4-fluorophenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21)=O)C1=CC=C(F)C=C1 DASRMIKJLWLNIA-UHFFFAOYSA-N 0.000 description 1
- FHUWSZOZYFYYOU-UHFFFAOYSA-N 8-[bis(4-fluorophenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21)=O)C1=CC=C(F)C=C1 FHUWSZOZYFYYOU-UHFFFAOYSA-N 0.000 description 1
- VUOAWASKQSJHLA-UHFFFAOYSA-N 8-[bis(4-fluorophenyl)methyl]-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)N2C(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)C2=N1 VUOAWASKQSJHLA-UHFFFAOYSA-N 0.000 description 1
- SPKQNZCCXWETSR-UHFFFAOYSA-N 8-[cyclohexyl(phenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C3CCCCC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 SPKQNZCCXWETSR-UHFFFAOYSA-N 0.000 description 1
- QQAWJVPAGCOCOX-UHFFFAOYSA-N 8-[cyclohexyl(phenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C3CCCCC3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 QQAWJVPAGCOCOX-UHFFFAOYSA-N 0.000 description 1
- BRLHEXQAGWUKLV-UHFFFAOYSA-N 8-[cyclohexyl(phenyl)methyl]-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)N2C(C3CCCCC3)C=3C=CC=CC=3)C2=N1 BRLHEXQAGWUKLV-UHFFFAOYSA-N 0.000 description 1
- INMVJZRNLRKWFO-UHFFFAOYSA-N 8-[cyclopropyl-(4-fluorophenyl)methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21)=O)C1CC1 INMVJZRNLRKWFO-UHFFFAOYSA-N 0.000 description 1
- UZXAJBJYGNRGSC-UHFFFAOYSA-N 8-[cyclopropyl-(4-fluorophenyl)methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(F)=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21)=O)C1CC1 UZXAJBJYGNRGSC-UHFFFAOYSA-N 0.000 description 1
- UNPBZGAOVOOOCC-UHFFFAOYSA-N 8-[cyclopropyl-(4-fluorophenyl)methyl]-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)N2C(C3CC3)C=3C=CC(F)=CC=3)C2=N1 UNPBZGAOVOOOCC-UHFFFAOYSA-N 0.000 description 1
- KPPMQXSTMWANKK-UHFFFAOYSA-N 8-[phenyl-[2-(trifluoromethyl)phenyl]methyl]-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound FC(F)(F)C1=CC=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3CCCCC3)N=C21)=O)C1=CC=CC=C1 KPPMQXSTMWANKK-UHFFFAOYSA-N 0.000 description 1
- CEGQUQFAFGRZGX-UHFFFAOYSA-N 8-[phenyl-[2-(trifluoromethyl)phenyl]methyl]-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound FC(F)(F)C1=CC=CC=C1C(N1C(C=CC2=CN=C(NC=3C=CC(=CC=3)N3N=CC=C3)N=C21)=O)C1=CC=CC=C1 CEGQUQFAFGRZGX-UHFFFAOYSA-N 0.000 description 1
- FQCRWDPYJJAAAI-UHFFFAOYSA-N 8-benzhydryl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 FQCRWDPYJJAAAI-UHFFFAOYSA-N 0.000 description 1
- NLXSSJIKZKHIHI-UHFFFAOYSA-N 8-benzhydryl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 NLXSSJIKZKHIHI-UHFFFAOYSA-N 0.000 description 1
- CUGJVILMQZQQCI-UHFFFAOYSA-N 8-benzhydryl-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)N2C(C=3C=CC=CC=3)C=3C=CC=CC=3)C2=N1 CUGJVILMQZQQCI-UHFFFAOYSA-N 0.000 description 1
- DBTHBJSMNKGKFI-UHFFFAOYSA-N 8-cyclohex-2-en-1-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C=CCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 DBTHBJSMNKGKFI-UHFFFAOYSA-N 0.000 description 1
- AMWQTYSDIWVUDR-UHFFFAOYSA-N 8-cyclohex-2-en-1-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3C=CCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 AMWQTYSDIWVUDR-UHFFFAOYSA-N 0.000 description 1
- DJFDXDYEHOGRRU-UHFFFAOYSA-N 8-cyclohex-2-en-1-yl-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)N2C3C=CCCC3)C2=N1 DJFDXDYEHOGRRU-UHFFFAOYSA-N 0.000 description 1
- VUOQYEFJYXGGIG-UHFFFAOYSA-N 8-cyclohex-3-en-1-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC=CCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 VUOQYEFJYXGGIG-UHFFFAOYSA-N 0.000 description 1
- CMRMWEQIQWUERP-UHFFFAOYSA-N 8-cyclohex-3-en-1-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CC=CCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 CMRMWEQIQWUERP-UHFFFAOYSA-N 0.000 description 1
- KDHYFZLPDJGOBN-UHFFFAOYSA-N 8-cyclohex-3-en-1-yl-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)N2C3CC=CCC3)C2=N1 KDHYFZLPDJGOBN-UHFFFAOYSA-N 0.000 description 1
- XLFNLCSKBUBVOE-UHFFFAOYSA-N 8-cyclohexyl-2-[4-(2-hydroxy-3-morpholin-4-ylpropoxy)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1COCCN1CC(O)COC(C=C1)=CC=C1NC(N=C12)=NC=C1C=CC(=O)N2C1CCCCC1 XLFNLCSKBUBVOE-UHFFFAOYSA-N 0.000 description 1
- KAXHMVLUMRRBAC-UHFFFAOYSA-N 8-cyclohexyl-2-[4-(3-methylpiperidin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1C(C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=O)N2C3CCCCC3)C2=N1 KAXHMVLUMRRBAC-UHFFFAOYSA-N 0.000 description 1
- JNYFHXCMSDBYAJ-UHFFFAOYSA-N 8-cyclohexyl-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)N2C3CCCCC3)C2=N1 JNYFHXCMSDBYAJ-UHFFFAOYSA-N 0.000 description 1
- RVEJGQCVSWQVRQ-UHFFFAOYSA-N 8-cyclohexyl-2-[4-[4-(2-morpholin-4-ylethyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1CCN1CCOCC1 RVEJGQCVSWQVRQ-UHFFFAOYSA-N 0.000 description 1
- RNSOFODMMJBEMP-UHFFFAOYSA-N 8-cyclohexyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]-1h-pyrido[2,3-d]pyrimidine-4,7-dione Chemical compound N=1C=2N(C3CCCCC3)C(=O)C=CC=2C(O)=NC=1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 RNSOFODMMJBEMP-UHFFFAOYSA-N 0.000 description 1
- VVHFOKVLTBFUCB-UHFFFAOYSA-N 8-cyclohexyl-6-fluoro-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C(F)=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 VVHFOKVLTBFUCB-UHFFFAOYSA-N 0.000 description 1
- GLKZNVQSZSWPOF-UHFFFAOYSA-N 8-cyclohexyl-6-methyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCC3)C(=O)C(C)=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 GLKZNVQSZSWPOF-UHFFFAOYSA-N 0.000 description 1
- ZHDSJOSZUSXHFQ-UHFFFAOYSA-N 8-cyclooctyl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 ZHDSJOSZUSXHFQ-UHFFFAOYSA-N 0.000 description 1
- IYSIDXAAGVMNIN-UHFFFAOYSA-N 8-cyclooctyl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCCCCC3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 IYSIDXAAGVMNIN-UHFFFAOYSA-N 0.000 description 1
- YGLCLJUDARCTIT-UHFFFAOYSA-N 8-cyclooctyl-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)N2C3CCCCCCC3)C2=N1 YGLCLJUDARCTIT-UHFFFAOYSA-N 0.000 description 1
- LPBDLZXZIHUGNN-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(2-hydroxy-3-morpholin-4-ylpropoxy)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1COCCN1CC(O)COC(C=C1)=CC=C1NC(N=C12)=NC=C1C=CC(=O)N2C1CCCC1 LPBDLZXZIHUGNN-UHFFFAOYSA-N 0.000 description 1
- SACFXVBFTZCIRB-UHFFFAOYSA-N 8-cyclopentyl-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)N2C3CCCC3)C2=N1 SACFXVBFTZCIRB-UHFFFAOYSA-N 0.000 description 1
- ZUJPLLVHANIGQH-UHFFFAOYSA-N 8-heptan-2-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CCCCC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 ZUJPLLVHANIGQH-UHFFFAOYSA-N 0.000 description 1
- YJRNPORAPFXOHS-UHFFFAOYSA-N 8-heptan-2-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CCCCC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 YJRNPORAPFXOHS-UHFFFAOYSA-N 0.000 description 1
- FPMSWQAQEXTXBT-UHFFFAOYSA-N 8-heptan-2-yl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CCCCC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 FPMSWQAQEXTXBT-UHFFFAOYSA-N 0.000 description 1
- ZSHOIVPJZGXVMR-UHFFFAOYSA-N 8-hex-2-ynyl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC#CCCC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 ZSHOIVPJZGXVMR-UHFFFAOYSA-N 0.000 description 1
- DJWFDZGZZRHSKF-UHFFFAOYSA-N 8-hex-2-ynyl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC#CCCC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 DJWFDZGZZRHSKF-UHFFFAOYSA-N 0.000 description 1
- KSVIWWCIHJHHOV-UHFFFAOYSA-N 8-hex-2-ynyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(CC#CCCC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 KSVIWWCIHJHHOV-UHFFFAOYSA-N 0.000 description 1
- QRLKRTUJMXUDPI-UHFFFAOYSA-N 8-hex-3-yn-2-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C#CCC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 QRLKRTUJMXUDPI-UHFFFAOYSA-N 0.000 description 1
- YFRAQSKWXWOEKS-UHFFFAOYSA-N 8-hex-3-yn-2-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C#CCC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 YFRAQSKWXWOEKS-UHFFFAOYSA-N 0.000 description 1
- OBXXIIWXWIOUTG-UHFFFAOYSA-N 8-hex-3-yn-2-yl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)C#CCC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 OBXXIIWXWIOUTG-UHFFFAOYSA-N 0.000 description 1
- PVHMFYWHLBCCEC-UHFFFAOYSA-N 8-oct-1-yn-3-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C#C)CCCCC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 PVHMFYWHLBCCEC-UHFFFAOYSA-N 0.000 description 1
- QXJNMZSHRNZTMA-UHFFFAOYSA-N 8-oct-1-yn-3-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C#C)CCCCC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 QXJNMZSHRNZTMA-UHFFFAOYSA-N 0.000 description 1
- WFAYMJIYKQQJJD-UHFFFAOYSA-N 8-octan-2-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CCCCCC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 WFAYMJIYKQQJJD-UHFFFAOYSA-N 0.000 description 1
- OJXUZKOPNBRREL-UHFFFAOYSA-N 8-octan-2-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C)CCCCCC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 OJXUZKOPNBRREL-UHFFFAOYSA-N 0.000 description 1
- FPPMSGGOOTVDTM-UHFFFAOYSA-N 8-pent-1-yn-3-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C#C)CC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 FPPMSGGOOTVDTM-UHFFFAOYSA-N 0.000 description 1
- WHNLABPJMMWPEL-UHFFFAOYSA-N 8-pent-1-yn-3-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(C#C)CC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 WHNLABPJMMWPEL-UHFFFAOYSA-N 0.000 description 1
- WGRUVAAHHYJPRS-UHFFFAOYSA-N 8-pent-4-yn-2-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(CC#C)C)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 WGRUVAAHHYJPRS-UHFFFAOYSA-N 0.000 description 1
- IQGWXISLTQVPMW-UHFFFAOYSA-N 8-pent-4-yn-2-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(CC#C)C)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 IQGWXISLTQVPMW-UHFFFAOYSA-N 0.000 description 1
- XFMVZZFPEFOZCF-UHFFFAOYSA-N 8-pentan-3-yl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(CC)CC)C2=NC=1NC(C=C1)=CC=C1N1CCCCC1 XFMVZZFPEFOZCF-UHFFFAOYSA-N 0.000 description 1
- OAMVJPNWMKIITB-UHFFFAOYSA-N 8-pentan-3-yl-2-(4-pyrazol-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=CC(=O)N(C(CC)CC)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 OAMVJPNWMKIITB-UHFFFAOYSA-N 0.000 description 1
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 108010039627 Aprotinin Proteins 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000201370 Autographa californica nucleopolyhedrovirus Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- QCHWLKJNBBDCHD-UHFFFAOYSA-N C1(=CC=CC=C1)CCC(C1=CC=CC=C1)N1C(C=CC2=C1N=C(N=C2)NC2=CC=C(C=C2)N2CCCCC2)=O Chemical compound C1(=CC=CC=C1)CCC(C1=CC=CC=C1)N1C(C=CC2=C1N=C(N=C2)NC2=CC=C(C=C2)N2CCCCC2)=O QCHWLKJNBBDCHD-UHFFFAOYSA-N 0.000 description 1
- VFFACOCQIRUMOM-UHFFFAOYSA-N C1(=CC=CC=C1)CCC(C1=CC=CC=C1)N1C(C=CC2=C1N=C(N=C2)NC2=CC=C(C=C2)N2N=CC=C2)=O Chemical compound C1(=CC=CC=C1)CCC(C1=CC=CC=C1)N1C(C=CC2=C1N=C(N=C2)NC2=CC=C(C=C2)N2N=CC=C2)=O VFFACOCQIRUMOM-UHFFFAOYSA-N 0.000 description 1
- ANDDSFXMNRAYAH-UHFFFAOYSA-N C1(=CC=CC=C1)CCC(C1=CC=CC=C1)N1C(C=CC2=C1N=C(N=C2)NC2=CC=CC=C2)=O Chemical compound C1(=CC=CC=C1)CCC(C1=CC=CC=C1)N1C(C=CC2=C1N=C(N=C2)NC2=CC=CC=C2)=O ANDDSFXMNRAYAH-UHFFFAOYSA-N 0.000 description 1
- FHVRJSDSLSDDSY-UHFFFAOYSA-N C1(CC1)CCN1C(C=CC2=C1N=C(N=C2)NC2=CC=C(C=C2)N2CCCCC2)=O Chemical compound C1(CC1)CCN1C(C=CC2=C1N=C(N=C2)NC2=CC=C(C=C2)N2CCCCC2)=O FHVRJSDSLSDDSY-UHFFFAOYSA-N 0.000 description 1
- HJZMNYRSBIOYGD-UHFFFAOYSA-N C1C(C)NC(C)CN1C(C=C1)=CC=C1NC1=NC(C2C3CCC(C3)C2)=C(C=CC(=O)N2)C2=N1 Chemical compound C1C(C)NC(C)CN1C(C=C1)=CC=C1NC1=NC(C2C3CCC(C3)C2)=C(C=CC(=O)N2)C2=N1 HJZMNYRSBIOYGD-UHFFFAOYSA-N 0.000 description 1
- HJXWJCIYILDKSV-UHFFFAOYSA-N C1C(O)CCCN1C(C=C1)=CC=C1NC1=NC(C2C3CCC(C3)C2)=C(C=CC(=O)N2)C2=N1 Chemical compound C1C(O)CCCN1C(C=C1)=CC=C1NC1=NC(C2C3CCC(C3)C2)=C(C=CC(=O)N2)C2=N1 HJXWJCIYILDKSV-UHFFFAOYSA-N 0.000 description 1
- GWXHFFWSFJIKKQ-UHFFFAOYSA-N CC(=CCN1C(C=CC2=C1N=C(N=C2)NC2=CC=C(C=C2)N2CCCCC2)=O)C Chemical compound CC(=CCN1C(C=CC2=C1N=C(N=C2)NC2=CC=C(C=C2)N2CCCCC2)=O)C GWXHFFWSFJIKKQ-UHFFFAOYSA-N 0.000 description 1
- JSPKKKMXAHRTEP-UHFFFAOYSA-N CCC(C)N1CC=CC2=CN=C(N=C21)NC3=CC=CC=C3 Chemical compound CCC(C)N1CC=CC2=CN=C(N=C21)NC3=CC=CC=C3 JSPKKKMXAHRTEP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 102000002554 Cyclin A Human genes 0.000 description 1
- 108010068192 Cyclin A Proteins 0.000 description 1
- 102000002427 Cyclin B Human genes 0.000 description 1
- 108010068150 Cyclin B Proteins 0.000 description 1
- 102000003910 Cyclin D Human genes 0.000 description 1
- 108090000259 Cyclin D Proteins 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 102000016621 Focal Adhesion Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108010067715 Focal Adhesion Protein-Tyrosine Kinases Proteins 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- YSWHPLCDIMUKFE-QWRGUYRKSA-N Glu-Tyr Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 YSWHPLCDIMUKFE-QWRGUYRKSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101000846416 Homo sapiens Fibroblast growth factor 1 Proteins 0.000 description 1
- 101000851176 Homo sapiens Pro-epidermal growth factor Proteins 0.000 description 1
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102100023408 KH domain-containing, RNA-binding, signal transduction-associated protein 1 Human genes 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 229930194542 Keto Chemical group 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FUVVBXZYLZJGPW-UHFFFAOYSA-N O(C1=CC=CC=C1)C=1C=C(CN2C(C=CC3=C2N=C(N=C3)NC3=CC=C(C=C3)N3CCCCC3)=O)C=CC1 Chemical compound O(C1=CC=CC=C1)C=1C=C(CN2C(C=CC3=C2N=C(N=C3)NC3=CC=C(C=C3)N3CCCCC3)=O)C=CC1 FUVVBXZYLZJGPW-UHFFFAOYSA-N 0.000 description 1
- PBRNTAVCXMSMDI-UHFFFAOYSA-N O1COC2=C1C=CC(=C2)CN2C(C=CC1=C2N=C(N=C1)NC1=CC=CC=C1)=O Chemical compound O1COC2=C1C=CC(=C2)CN2C(C=CC1=C2N=C(N=C1)NC1=CC=CC=C1)=O PBRNTAVCXMSMDI-UHFFFAOYSA-N 0.000 description 1
- RLQZNRLPONQUNZ-UHFFFAOYSA-N OCC1CCCCN1C(C=C1)=CC=C1NC1=NC(C2C3CCC(C3)C2)=C(C=CC(=O)N2)C2=N1 Chemical compound OCC1CCCCN1C(C=C1)=CC=C1NC1=NC(C2C3CCC(C3)C2)=C(C=CC(=O)N2)C2=N1 RLQZNRLPONQUNZ-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 101150093908 PDGFRB gene Proteins 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100027384 Proto-oncogene tyrosine-protein kinase Src Human genes 0.000 description 1
- 101710122944 Proto-oncogene tyrosine-protein kinase Src Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 102100031167 Tyrosine-protein kinase CSK Human genes 0.000 description 1
- 101710086605 Tyrosine-protein kinase CSK Proteins 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- HPFVBGJFAYZEBE-XNBTXCQYSA-N [(8r,9s,10r,13s,14s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CCC(=O)C=C3CC2)C)CC[C@@]11C)CC1OC(=O)CCC1CCCC1 HPFVBGJFAYZEBE-XNBTXCQYSA-N 0.000 description 1
- VVLRASGCTQMFFU-UHFFFAOYSA-N [1-(4-aminophenyl)piperidin-2-yl]methanol Chemical compound C1=CC(N)=CC=C1N1C(CO)CCCC1 VVLRASGCTQMFFU-UHFFFAOYSA-N 0.000 description 1
- ZPGVLDQXMSGLHG-UHFFFAOYSA-N [1-(4-aminophenyl)piperidin-3-yl]methanol Chemical compound C1=CC(N)=CC=C1N1CC(CO)CCC1 ZPGVLDQXMSGLHG-UHFFFAOYSA-N 0.000 description 1
- GZZVJDVYXKXPNH-UHFFFAOYSA-N [1-(4-nitrophenyl)piperidin-2-yl]methanol Chemical compound OCC1CCCCN1C1=CC=C([N+]([O-])=O)C=C1 GZZVJDVYXKXPNH-UHFFFAOYSA-N 0.000 description 1
- GHESWKCVPRIYLS-UHFFFAOYSA-N [1-(4-nitrophenyl)piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1C1=CC=C([N+]([O-])=O)C=C1 GHESWKCVPRIYLS-UHFFFAOYSA-N 0.000 description 1
- AVBGZCPLSCOJBV-UHFFFAOYSA-N [4-(3-bicyclo[2.2.1]heptanylamino)-2-methylsulfanylpyrimidin-5-yl]methanol Chemical compound CSC1=NC=C(CO)C(NC2C3CCC(C3)C2)=N1 AVBGZCPLSCOJBV-UHFFFAOYSA-N 0.000 description 1
- DVCFSGVOYRHECI-UHFFFAOYSA-N [4-(cycloheptylamino)-2-methylsulfanylpyrimidin-5-yl]methanol Chemical compound CSC1=NC=C(CO)C(NC2CCCCCC2)=N1 DVCFSGVOYRHECI-UHFFFAOYSA-N 0.000 description 1
- JWKZOJHMOOCSRM-UHFFFAOYSA-N [4-(cyclohexylamino)-2-methylsulfanylpyrimidin-5-yl]methanol Chemical compound CSC1=NC=C(CO)C(NC2CCCCC2)=N1 JWKZOJHMOOCSRM-UHFFFAOYSA-N 0.000 description 1
- CKAUBDFSCOMSLH-UHFFFAOYSA-N [4-(cyclopropylamino)-2-methylsulfanylpyrimidin-5-yl]methanol Chemical compound CSC1=NC=C(CO)C(NC2CC2)=N1 CKAUBDFSCOMSLH-UHFFFAOYSA-N 0.000 description 1
- KMVHQNQPRBWOHB-UHFFFAOYSA-N [PH5].C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 Chemical compound [PH5].C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 KMVHQNQPRBWOHB-UHFFFAOYSA-N 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical class O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002788 anti-peptide Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229960004405 aprotinin Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
- 239000013000 chemical inhibitor Substances 0.000 description 1
- 239000007958 cherry flavor Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- SIHZWGODIRRSRA-ONEGZZNKSA-N erbstatin Chemical compound OC1=CC=C(O)C(\C=C\NC=O)=C1 SIHZWGODIRRSRA-ONEGZZNKSA-N 0.000 description 1
- 201000004101 esophageal cancer Diseases 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MANFWSKJPOXKJZ-UHFFFAOYSA-N ethyl 2,4-diaminopyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(N)N=C1N MANFWSKJPOXKJZ-UHFFFAOYSA-N 0.000 description 1
- FRFWTLSXMAKEHH-UHFFFAOYSA-N ethyl 3-[4-[[2-[tert-butyl(dimethyl)silyl]oxycyclopentyl]amino]-2-methylsulfanylpyrimidin-5-yl]prop-2-enoate Chemical compound CCOC(=O)C=CC1=CN=C(SC)N=C1NC1C(O[Si](C)(C)C(C)(C)C)CCC1 FRFWTLSXMAKEHH-UHFFFAOYSA-N 0.000 description 1
- JTBBVVXVGZXGRB-UHFFFAOYSA-N ethyl 4-(cycloheptylamino)-2-methylsulfanylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SC)N=C1NC1CCCCCC1 JTBBVVXVGZXGRB-UHFFFAOYSA-N 0.000 description 1
- VCBPLIQPECNECO-UHFFFAOYSA-N ethyl 4-(cyclohexylamino)-2-methylsulfanylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SC)N=C1NC1CCCCC1 VCBPLIQPECNECO-UHFFFAOYSA-N 0.000 description 1
- VOLYYVCUCYOUDG-UHFFFAOYSA-N ethyl 4-(cyclopropylamino)-2-methylsulfanylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SC)N=C1NC1CC1 VOLYYVCUCYOUDG-UHFFFAOYSA-N 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 102000006495 integrins Human genes 0.000 description 1
- 108010044426 integrins Proteins 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000000021 kinase assay Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- PVSJXEDBEXYLML-UHFFFAOYSA-N methyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate Chemical compound COC(=O)CP(=O)(OCC(F)(F)F)OCC(F)(F)F PVSJXEDBEXYLML-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 150000007522 mineralic acids Chemical group 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- OCTNQAZYWLBDEB-UHFFFAOYSA-N n,n-dimethyl-1-(4-nitrophenyl)piperidin-4-amine Chemical compound C1CC(N(C)C)CCN1C1=CC=C([N+]([O-])=O)C=C1 OCTNQAZYWLBDEB-UHFFFAOYSA-N 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- QWLISCJHYITNQF-UHFFFAOYSA-N n-methoxy-1-phenylmethanamine Chemical compound CONCC1=CC=CC=C1 QWLISCJHYITNQF-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- GVUGOAYIVIDWIO-UFWWTJHBSA-N nepidermin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CS)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C(C)C)C(C)C)C1=CC=C(O)C=C1 GVUGOAYIVIDWIO-UFWWTJHBSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 1
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- ONRZYLHPWDWPAV-UHFFFAOYSA-N o-ethyl 4-amino-2-methylpyrimidine-5-carbothioate Chemical compound CCOC(=S)C1=CN=C(C)N=C1N ONRZYLHPWDWPAV-UHFFFAOYSA-N 0.000 description 1
- QXAHJILNWYDAIV-UHFFFAOYSA-N o-ethyl 4-chloro-2-methylpyrimidine-5-carbothioate Chemical compound CCOC(=S)C1=CN=C(C)N=C1Cl QXAHJILNWYDAIV-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- GTVPOLSIJWJJNY-UHFFFAOYSA-N olomoucine Chemical compound N1=C(NCCO)N=C2N(C)C=NC2=C1NCC1=CC=CC=C1 GTVPOLSIJWJJNY-UHFFFAOYSA-N 0.000 description 1
- 231100000590 oncogenic Toxicity 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 229950000964 pepstatin Drugs 0.000 description 1
- 108010091212 pepstatin Proteins 0.000 description 1
- FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical compound [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 229920000131 polyvinylidene Polymers 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000034932 regulation of DNA biosynthetic process Effects 0.000 description 1
- 230000034394 regulation of mitosis Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- SIJPRSOYWPBTMO-UHFFFAOYSA-N tert-butyl 1-(4-aminophenyl)pyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCCN1C1=CC=C(N)C=C1 SIJPRSOYWPBTMO-UHFFFAOYSA-N 0.000 description 1
- POQDXNJMCJKFKV-UHFFFAOYSA-N tert-butyl 1-(4-nitrophenyl)pyrrolidine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCCN1C1=CC=C([N+]([O-])=O)C=C1 POQDXNJMCJKFKV-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 231100000588 tumorigenic Toxicity 0.000 description 1
- 230000000381 tumorigenic effect Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 201000011531 vascular cancer Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3722097P | 1997-02-05 | 1997-02-05 | |
| US60/037,220 | 1997-02-05 | ||
| US6974397P | 1997-12-16 | 1997-12-16 | |
| US60/069,743 | 1997-12-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000070751A true KR20000070751A (ko) | 2000-11-25 |
Family
ID=26713919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019997007010A Ceased KR20000070751A (ko) | 1997-02-05 | 1998-01-26 | 세포 증식 억제제로서의 피리도[2,3-ｄ]피리미딘 및 4-아미노피리미딘 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0964864B1 (https=) |
| JP (1) | JP2001509805A (https=) |
| KR (1) | KR20000070751A (https=) |
| AT (1) | ATE391719T1 (https=) |
| AU (1) | AU749750B2 (https=) |
| BR (1) | BR9807305A (https=) |
| CA (1) | CA2271157A1 (https=) |
| DE (1) | DE69839338T2 (https=) |
| ES (1) | ES2301194T3 (https=) |
| HR (1) | HRP980060A2 (https=) |
| WO (1) | WO1998033798A2 (https=) |
Families Citing this family (249)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6811779B2 (en) | 1994-02-10 | 2004-11-02 | Imclone Systems Incorporated | Methods for reducing tumor growth with VEGF receptor antibody combined with radiation and chemotherapy |
| PL342447A1 (en) | 1997-10-27 | 2001-06-04 | Agouron Pharma | Substituted 4-amino thiazol-2-yl compounds as inhibitors of cyclin-dependent kinases |
| EP1801112A1 (en) * | 1998-05-26 | 2007-06-27 | Warner-Lambert Company LLC | Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation |
| TR200003429T2 (tr) * | 1998-05-26 | 2001-07-23 | Warner-Lambert Company | Hücresel çoğalma inhibitörleri olarak bisiklik pirimidinler ve bisiklik 3,4-dihidropirimidinler. |
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| SK286640B6 (sk) | 1998-06-19 | 2009-03-05 | Pfizer Products Inc. | Pyrol [2,3-d] pyrimidínová zlúčenina, jej použitie na výrobu liečiva, farmaceutická kompozícia s jej obsahom, použitie jej kombinácie s ďalšími činidlami a súpravy s jej obsahom na výrobu liečiva |
| ATE342892T1 (de) | 1998-08-29 | 2006-11-15 | Astrazeneca Ab | Pyrimidine verbindungen |
| US6632820B1 (en) | 1998-08-29 | 2003-10-14 | Astrazeneca Ab | Pyrimidine compounds |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| US6399633B1 (en) | 1999-02-01 | 2002-06-04 | Aventis Pharmaceuticals Inc. | Use of 4-H-1-benzopryan-4-one derivatives as inhibitors of smooth muscle cell proliferation |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| GB9907658D0 (en) | 1999-04-06 | 1999-05-26 | Zeneca Ltd | Chemical compounds |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| EP1235815A1 (en) * | 1999-11-22 | 2002-09-04 | Warner-Lambert Company | Quinazolines and their use for inhibiting cyclin-dependent kinase enzymes |
| US6982260B1 (en) | 1999-11-22 | 2006-01-03 | Warner-Lambert Company | Quinazolines and their use for inhibiting cyclin-dependent kinase enzymes |
| DE60037345T2 (de) | 1999-12-10 | 2008-11-13 | Pfizer Products Inc., Groton | Pyrrolo(2,3-d)pyrimidin-Verbindungen |
| YU54202A (sh) | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| HN2001000008A (es) | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| JP2003523358A (ja) * | 2000-01-27 | 2003-08-05 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 神経変性疾患の治療のためのピリドピリミジノン誘導体 |
| GB0004886D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004888D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| US7235551B2 (en) | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
| AP2002002643A0 (en) * | 2000-03-06 | 2002-12-31 | Warner Lambert Co | 5-alkylpyrido[2,3-d]pyrimidines tyrosine kinase inhibitors |
| GB0007371D0 (en) * | 2000-03-28 | 2000-05-17 | Astrazeneca Uk Ltd | Chemical compounds |
| MXPA02010222A (es) | 2000-04-18 | 2003-05-23 | Agouron Pharma | Pirazoles para inhibir proteina cinasa. |
| KR100423899B1 (ko) * | 2000-05-10 | 2004-03-24 | 주식회사 엘지생명과학 | 세포 증식 억제제로 유용한 1,1-디옥소이소티아졸리딘을갖는 인다졸 |
| ATE423120T1 (de) | 2000-06-26 | 2009-03-15 | Pfizer Prod Inc | Pyrroloä2,3-düpyrimidin verbindungen als immunosuppressive wirkstoffe |
| GB0016877D0 (en) | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
| WO2002012250A2 (en) | 2000-08-09 | 2002-02-14 | Agouron Pharmaceuticals, Inc. | Pyrazole-thiazole compounds, pharmaceutical compositions containing them, and methods of their use for inhibiting cyclin-dependent kinases |
| DE60110802T2 (de) | 2000-08-18 | 2005-10-06 | Agouron Pharmaceuticals, Inc., San Diego | Heterozyklische-hydroximino-fluorene und ihre verwendung zur inhibierung von proteinkinasen |
| GB0021726D0 (en) | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| CN100525768C (zh) | 2000-10-23 | 2009-08-12 | 史密丝克莱恩比彻姆公司 | 新化合物 |
| US6756374B2 (en) | 2001-01-22 | 2004-06-29 | Hoffmann-La Roche Inc. | Diaminothiazoles having antiproliferative activity |
| DE60206363T2 (de) | 2001-02-12 | 2006-07-06 | F. Hoffmann-La Roche Ag | 6-substituierte pyridopyrimidine |
| GB0103926D0 (en) * | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| JP4166991B2 (ja) * | 2001-02-26 | 2008-10-15 | 田辺三菱製薬株式会社 | ピリドピリミジンまたはナフチリジン誘導体 |
| BR0209774A (pt) | 2001-05-29 | 2004-06-01 | Schering Ag | Pirimidinas inibidoras de cdk, sua preparação e aplicação como medicamento |
| GB0113041D0 (en) | 2001-05-30 | 2001-07-18 | Astrazeneca Ab | Chemical compounds |
| US7301023B2 (en) | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| MXPA04005939A (es) | 2002-01-22 | 2005-01-25 | Warner Lambert Co | 2-(piridin-2-ilamino)-pirido[2,3-d]pirimidin-7-onas. |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| GB0205693D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| GB0205688D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| US7442697B2 (en) | 2002-03-09 | 2008-10-28 | Astrazeneca Ab | 4-imidazolyl substituted pyrimidine derivatives with CDK inhibitory activity |
| KR20040103972A (ko) | 2002-04-19 | 2004-12-09 | 스미스클라인 비참 코포레이션 | 신규 화합물 |
| AU2003251661A1 (en) | 2002-08-06 | 2004-02-25 | F. Hoffmann-La Roche Ag | 6-alkoxy-pyrido-pyrimidines as p-38 map kinase inhibitors |
| EP1557418B1 (en) * | 2002-10-29 | 2012-04-04 | Msd K.K. | Quinoxaline derivatives |
| WO2004043367A2 (en) | 2002-11-06 | 2004-05-27 | Bristol-Myers Squibb Company | Fused heterocyclic compounds and use thereof |
| NZ539901A (en) | 2002-11-26 | 2007-09-28 | Pfizer Prod Inc | Method of treatment of transplant rejection |
| JP2006508997A (ja) * | 2002-11-28 | 2006-03-16 | シエーリング アクチエンゲゼルシャフト | Ｃｈｋ−、Ｐｄｋ−およびＡｋｔ−阻害性ピリミジン、それらの製造および薬剤としての使用 |
| US7098332B2 (en) * | 2002-12-20 | 2006-08-29 | Hoffmann-La Roche Inc. | 5,8-Dihydro-6H-pyrido[2,3-d]pyrimidin-7-ones |
| CN100420687C (zh) * | 2002-12-20 | 2008-09-24 | 霍夫曼-拉罗奇有限公司 | 作为选择性kdr和fgfr抑制剂的吡啶并[2,3-d]嘧啶衍生物 |
| MXPA05007503A (es) * | 2003-01-17 | 2005-09-21 | Warner Lambert Co | Heterociclicos 2-aminopiridina sustituidos como inhibidores de proliferacion celular. |
| US7157455B2 (en) * | 2003-02-10 | 2007-01-02 | Hoffmann-La Roche Inc. | 4-Aminopyrimidine-5-one derivatives |
| MXPA05011710A (es) | 2003-05-05 | 2006-01-23 | Hoffmann La Roche | Derivados de pirimidina con actividad de crf. |
| GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| WO2005001053A2 (en) | 2003-06-09 | 2005-01-06 | Samuel Waksal | Method of inhibiting receptor tyrosine kinases with an extracellular antagonist and an intracellular antagonist |
| RU2356901C2 (ru) * | 2003-07-30 | 2009-05-27 | Райджел Фармасьютикалз, Инк. | Соединения 2, 4-пиримидиндиамина, обладающие воздействием при аутоиммунных расстройствах |
| WO2005012294A1 (en) | 2003-07-30 | 2005-02-10 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| RU2348632C2 (ru) | 2003-11-13 | 2009-03-10 | Ф.Хоффманн-Ля Рош Аг | Гидроксиалкилзамещенные пиридо-7-пиримидин-7-оны |
| TW200528101A (en) | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
| CN1918158B (zh) * | 2004-02-14 | 2011-03-02 | Irm责任有限公司 | 作为蛋白激酶抑制剂的化合物和组合物 |
| CA2560305C (en) | 2004-03-19 | 2016-07-05 | Imclone Systems Incorporated | Human anti-epidermal growth factor receptor antibody |
| US7211576B2 (en) | 2004-04-20 | 2007-05-01 | Hoffmann-La Roche Inc. | Diaminothiazoles |
| US7767687B2 (en) * | 2004-12-13 | 2010-08-03 | Biogen Idec Ma Inc. | Pyrido pyrimidinones, dihydro pyrimido pyrimidinones and pteridinones useful as RAF kinase inhibitors |
| MX2007008781A (es) | 2005-01-21 | 2007-09-11 | Astex Therapeutics Ltd | Compuestos farmaceuticos. |
| PE20061193A1 (es) | 2005-03-25 | 2006-12-02 | Glaxo Group Ltd | DERIVADOS DE 3,4-DIHIDROPIRIMIDO[4,5-d]PIRIMIDIN-2-[1H]-0NA COMO INHIBIDORES DE QUINASA p38 |
| US7423042B2 (en) | 2005-03-25 | 2008-09-09 | Glaxo Group Limited | Compounds |
| US20080096905A1 (en) | 2005-03-25 | 2008-04-24 | Glaxo Group Limited | Process For Preparing Pyrido[2,3-D]Pyrimidin-7-One And 3,4-Dihydropyrimido{4,5-D}Pyrimidin-2(1H)-One Derivatives |
| MY145343A (en) | 2005-03-25 | 2012-01-31 | Glaxo Group Ltd | Novel compounds |
| CA2612449A1 (en) | 2005-06-17 | 2006-12-28 | Imclone Systems Incorporated | Receptor antagonists for treatment of metastatic bone cancer |
| JP2009505658A (ja) | 2005-08-24 | 2009-02-12 | ブリストル−マイヤーズ スクイブ カンパニー | 上皮増殖因子受容体モデュレーターに対する感受性を決定するためのバイオマーカーおよび方法 |
| WO2007036791A1 (en) * | 2005-09-28 | 2007-04-05 | Ranbaxy Laboratories Limited | Pyrido-pyridimidine derivatives useful as antiinflammatory agents |
| AR056556A1 (es) | 2005-09-30 | 2007-10-10 | Astrazeneca Ab | Imidazo(1,2-a)piridina con actividad antiproliferacion celular |
| CN102746298A (zh) * | 2005-10-07 | 2012-10-24 | 埃克塞里艾克西斯公司 | PI3Kα的吡啶并嘧啶酮抑制剂 |
| EA016945B1 (ru) | 2005-10-07 | 2012-08-30 | Экселиксис, Инк. | ПИРИДОПИРИМИДИНОНОВЫЕ ИНГИБИТОРЫ PI3Kα |
| CN101528231A (zh) * | 2006-08-16 | 2009-09-09 | 埃克塞利希斯股份有限公司 | 在癌症的治疗中使用pi3k和mek调控剂 |
| PT2074122E (pt) | 2006-09-15 | 2011-08-24 | Pfizer Prod Inc | Compostos de pirido(2,3-d)-pirimidinona e sua utilização como inibidores de pi3 |
| EP2073807A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| EP1914234A1 (en) | 2006-10-16 | 2008-04-23 | GPC Biotech Inc. | Pyrido[2,3-d]pyrimidines and their use as kinase inhibitors |
| WO2008150260A1 (en) * | 2007-06-06 | 2008-12-11 | Gpc Biotech, Inc. | 8-oxy-2-aminopyrido (2, 3-d) pyrimidin-7-one derivatives as kinase inhibitors and anticancer agents |
| CA2683784A1 (en) * | 2007-04-11 | 2008-10-23 | Exelixis, Inc. | Pyrido[2,3-d]pyrimidin-7-one compounds as inhibitors of pi3k-alpha for the treatment of cancer |
| EP2100894A1 (en) * | 2008-03-12 | 2009-09-16 | 4Sc Ag | Pyridopyrimidines used as Plk1 (polo-like kinase) inhibitors |
| EP2112150B1 (en) | 2008-04-22 | 2013-10-16 | Forma Therapeutics, Inc. | Improved raf inhibitors |
| CA2719868A1 (en) * | 2008-04-29 | 2009-11-05 | F. Hoffmann-La Roche Ag | Pyrimidinyl pyridone inhibitors of jnk. |
| ES2439009T3 (es) * | 2008-08-20 | 2014-01-21 | Merck Sharp & Dohme Corp. | Derivados de piridina y pirimidina sustituidos con etenilo y su uso en el tratamiento de infecciones virales |
| KR101335843B1 (ko) | 2008-08-20 | 2013-12-02 | 조에티스 엘엘씨 | 피롤로[2,3-ｄ]피리미딘 화합물 |
| AR073524A1 (es) | 2008-09-30 | 2010-11-10 | Exelixis Inc | Piridopirimidinonas inhibidores de pi3k a y m tor |
| CA2734037A1 (en) * | 2008-10-22 | 2010-04-29 | F. Hoffmann-La Roche Ag | Pyrimidinyl pyridone inhibitors of jnk |
| WO2010099139A2 (en) | 2009-02-25 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Combination anti-cancer therapy |
| JP2012519170A (ja) | 2009-02-26 | 2012-08-23 | オーエスアイ・ファーマシューティカルズ，エルエルシー | 生体内の腫瘍細胞のｅｍｔステータスをモニターするためのｉｎｓｉｔｕ法 |
| WO2010099364A2 (en) | 2009-02-27 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| WO2010099138A2 (en) | 2009-02-27 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| WO2010099363A1 (en) | 2009-02-27 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| EP2408479A1 (en) | 2009-03-18 | 2012-01-25 | OSI Pharmaceuticals, LLC | Combination cancer therapy comprising administration of an egfr inhibitor and an igf-1r inhibitor |
| JP2012526850A (ja) | 2009-05-13 | 2012-11-01 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | サイクリン依存性キナーゼ阻害剤及びその用法 |
| EP2494070A2 (en) | 2009-10-30 | 2012-09-05 | Bristol-Myers Squibb Company | Methods for treating cancer in patients having igf-1r inhibitor resistance |
| CA2780875A1 (en) | 2009-11-13 | 2011-05-19 | Pangaea Biotech, S.L. | Molecular biomarkers for predicting response to tyrosine kinase inhibitors in lung cancer |
| UY33221A (es) | 2010-02-09 | 2011-09-30 | Univ California | MÉTODOS PARA TRATAR CÁNCER USANDO INHIBIDORES DE PI3K Y mTOR EN COMBINACIÓN CON INHIBIDORES DE AUTOFAGIA |
| EP2580214A4 (en) | 2010-06-09 | 2013-12-04 | Afraxis Holdings Inc | 8- (SULFONYLARYL) PYRIDO [2,3-D] PYRIMIDIN-7 (8H) -ONES FOR THE TREATMENT OF CNS DISORDERS |
| EP2580213A4 (en) * | 2010-06-09 | 2013-12-25 | Afraxis Holdings Inc | 8- (HETEROARYLMETHYL) PYRIDO [2,3-D] PYRIMIDIN-7 (8H) -ONES FOR THE TREATMENT OF CNS DISORDERS |
| WO2011156786A2 (en) * | 2010-06-10 | 2011-12-15 | Afraxis, Inc. | 6-(ethynyl)pyrido[2,3-d]pyrimidin-7(8h)-ones for the treatment of cns disorders |
| US20130252967A1 (en) * | 2010-06-10 | 2013-09-26 | Afraxis, Inc. | 8-(sulfonylbenzyl)pyrido[2,3-d]pyrimidin-7(8h)-ones for the treatment of cns disorders |
| WO2011156775A2 (en) * | 2010-06-10 | 2011-12-15 | Afraxis, Inc. | 8-(2'-heterocycyl)pyrido[2.3-d]pyrimidin-7(8h)-ones for the treatment of cns disorders |
| WO2011159726A2 (en) | 2010-06-14 | 2011-12-22 | The Scripps Research Institute | Reprogramming of cells to a new fate |
| US8691830B2 (en) | 2010-10-25 | 2014-04-08 | G1 Therapeutics, Inc. | CDK inhibitors |
| WO2012068381A2 (en) | 2010-11-17 | 2012-05-24 | The University Of North Carolina At Chapel Hill | Protection of renal tissues from schema through inhibition of the proliferative kisses cdk4 and cdk6 |
| EP2468883A1 (en) | 2010-12-22 | 2012-06-27 | Pangaea Biotech S.L. | Molecular biomarkers for predicting response to tyrosine kinase inhibitors in lung cancer |
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| US9134297B2 (en) | 2011-01-11 | 2015-09-15 | Icahn School Of Medicine At Mount Sinai | Method and compositions for treating cancer and related methods |
| EP2492688A1 (en) | 2011-02-23 | 2012-08-29 | Pangaea Biotech, S.A. | Molecular biomarkers for predicting response to antitumor treatment in lung cancer |
| WO2012129145A1 (en) | 2011-03-18 | 2012-09-27 | OSI Pharmaceuticals, LLC | Nscle combination therapy |
| US9139534B2 (en) * | 2011-04-22 | 2015-09-22 | Signal Pharmaceuticals, Llc | Substituted diaminocarboxamide and diaminocarbonitrile pyrimidines, compositions thereof, and methods of treatment therewith |
| WO2012149014A1 (en) | 2011-04-25 | 2012-11-01 | OSI Pharmaceuticals, LLC | Use of emt gene signatures in cancer drug discovery, diagnostics, and treatment |
| GB201106870D0 (en) | 2011-04-26 | 2011-06-01 | Univ Belfast | Marker |
| EP2751285B2 (en) | 2011-08-31 | 2020-04-01 | Genentech, Inc. | Method for sensitivity testing of a tumour for a egfr kinase inhibitor |
| EP2761025A1 (en) | 2011-09-30 | 2014-08-06 | Genentech, Inc. | Diagnostic methylation markers of epithelial or mesenchymal phenotype and response to egfr kinase inhibitor in tumours or tumour cells |
| EP2766497A1 (en) | 2011-10-13 | 2014-08-20 | Bristol-Myers Squibb Company | Methods for selecting and treating cancer in patients with igf-1r/ir inhibitors |
| WO2013113762A1 (en) | 2012-01-31 | 2013-08-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and kits for predicting the risk of having a cutaneous melanoma in a subject |
| CA2868966C (en) | 2012-03-29 | 2021-01-26 | Francis Xavier Tavares | Lactam kinase inhibitors |
| WO2013152252A1 (en) | 2012-04-06 | 2013-10-10 | OSI Pharmaceuticals, LLC | Combination anti-cancer therapy |
| RS58514B1 (sr) | 2012-06-13 | 2019-04-30 | Incyte Holdings Corp | Supstituisana triciklična jedinjenja kao inhibitori fgfr |
| WO2013190089A1 (en) | 2012-06-21 | 2013-12-27 | Pangaea Biotech, S.L. | Molecular biomarkers for predicting outcome in lung cancer |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| US9815847B2 (en) | 2013-03-14 | 2017-11-14 | Icahn School Of Medicine At Mount Sinai | Pyrimidine compounds as kinase inhibitors |
| ME03557B (me) | 2013-03-15 | 2020-07-20 | G1 Therapeutics Inc | Privremena zaštiтa normalnih ćelija током hemoterapije |
| CN105307657B (zh) * | 2013-03-15 | 2020-07-10 | 西建卡尔有限责任公司 | 杂芳基化合物和其用途 |
| US9321786B2 (en) | 2013-03-15 | 2016-04-26 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| EP3943087A1 (en) | 2013-03-15 | 2022-01-26 | Celgene CAR LLC | Heteroaryl compounds and uses thereof |
| CA2906157C (en) | 2013-03-15 | 2022-05-17 | G1 Therapeutics, Inc. | Highly active anti-neoplastic and anti-proliferative agents |
| EP2976085A1 (en) | 2013-03-21 | 2016-01-27 | INSERM - Institut National de la Santé et de la Recherche Médicale | Method and pharmaceutical composition for use in the treatment of chronic liver diseases associated with a low hepcidin expression |
| PH12015502383B1 (en) | 2013-04-19 | 2023-02-03 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| WO2015156674A2 (en) | 2014-04-10 | 2015-10-15 | Stichting Het Nederlands Kanker Instituut | Method for treating cancer |
| WO2015161288A1 (en) | 2014-04-17 | 2015-10-22 | G1 Therapeutics, Inc. | Tricyclic lactams for use as anti-neoplastic and anti-proliferative agents |
| ES2864079T3 (es) | 2014-05-30 | 2021-10-13 | Pfizer | Derivados de carbonitrilo como moduladores selectivos del receptor de andrógenos |
| WO2016040848A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Treatment of rb-negative tumors using topoisomerase inhibitors in combination with cyclin dependent kinase 4/6 inhibitors |
| EP3191098A4 (en) | 2014-09-12 | 2018-04-25 | G1 Therapeutics, Inc. | Combinations and dosing regimes to treat rb-positive tumors |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| WO2016105503A1 (en) | 2014-12-24 | 2016-06-30 | Genentech, Inc. | Therapeutic, diagnostic and prognostic methods for cancer of the bladder |
| TWI712601B (zh) | 2015-02-20 | 2020-12-11 | 美商英塞特公司 | 作為fgfr抑制劑之雙環雜環 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| HK1251655A1 (zh) | 2015-04-20 | 2019-02-01 | Tolero Pharmaceuticals, Inc. | 通过线粒体分析预测对阿伏西地的应答 |
| KR102608921B1 (ko) | 2015-05-18 | 2023-12-01 | 스미토모 파마 온콜로지, 인크. | 생체 이용률이 증가된 알보시딥 프로드러그 |
| JP7083497B2 (ja) | 2015-08-03 | 2022-06-13 | スミトモ ファーマ オンコロジー， インコーポレイテッド | がんの処置のための併用療法 |
| PT3497103T (pt) | 2016-08-15 | 2021-06-17 | Pfizer | Inibidores de piridopirimidinona cdk2/4/6 |
| WO2018078143A1 (en) | 2016-10-28 | 2018-05-03 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Means and methods for determining efficacy of anti-egfr inhibitors in colorectal cancer (crc) therapy |
| WO2018094275A1 (en) | 2016-11-18 | 2018-05-24 | Tolero Pharmaceuticals, Inc. | Alvocidib prodrugs and their use as protein kinase inhibitors |
| CN110366550A (zh) | 2016-12-22 | 2019-10-22 | 美国安进公司 | 作为用于治疗肺癌、胰腺癌或结直肠癌的KRAS G12C抑制剂的苯并异噻唑、异噻唑并[3,4-b]吡啶、喹唑啉、酞嗪、吡啶并[2,3-d]哒嗪和吡啶并[2,3-d]嘧啶衍生物 |
| MX2019008158A (es) | 2017-01-06 | 2019-12-09 | G1 Therapeutics Inc | Terapia de combinacion para el tratamiento del cancer. |
| AU2018273356B2 (en) | 2017-05-22 | 2021-09-16 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| WO2019006393A1 (en) | 2017-06-29 | 2019-01-03 | G1 Therapeutics, Inc. | Morphic forms of git38 and methods of manufacture thereof |
| AU2018329920B2 (en) | 2017-09-08 | 2022-12-01 | Amgen Inc. | Inhibitors of KRAS G12C and methods of using the same |
| JP7196160B2 (ja) | 2017-09-12 | 2022-12-26 | スミトモ ファーマ オンコロジー， インコーポレイテッド | Ｍｃｌ－１阻害剤アルボシジブを用いた、ｂｃｌ－２阻害剤に対して非感受性である癌の治療レジメン |
| HRP20241288T1 (hr) | 2018-05-04 | 2024-12-06 | Incyte Corporation | Čvrsti oblici fgfr inhibitora i postupci za njihovu proizvodnju |
| AU2019262579B2 (en) | 2018-05-04 | 2024-09-12 | Incyte Corporation | Salts of an FGFR inhibitor |
| EP3788053B1 (en) | 2018-05-04 | 2024-07-10 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
| CA3098574A1 (en) | 2018-05-04 | 2019-11-07 | Amgen Inc. | Kras g12c inhibitors and methods of using the same |
| MA52564A (fr) | 2018-05-10 | 2021-03-17 | Amgen Inc | Inhibiteurs de kras g12c pour le traitement du cancer |
| ES2929406T3 (es) * | 2018-05-21 | 2022-11-29 | Nerviano Medical Sciences Srl | Compuestos de piridonas heterocondensadas y su uso como inhibidores de IDH |
| US11096939B2 (en) | 2018-06-01 | 2021-08-24 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
| MX2020012204A (es) | 2018-06-11 | 2021-03-31 | Amgen Inc | Inhibidores de kras g12c para tratar el cáncer. |
| US11285156B2 (en) | 2018-06-12 | 2022-03-29 | Amgen Inc. | Substituted piperazines as KRAS G12C inhibitors |
| AU2019325685B2 (en) | 2018-08-24 | 2025-07-24 | Pharmacosmos Holding A/S | Improved synthesis of 1,4-diazaspiro(5.5)undecan-3-one |
| CN113194954A (zh) | 2018-10-04 | 2021-07-30 | 国家医疗保健研究所 | 用于治疗角皮病的egfr抑制剂 |
| JP7516029B2 (ja) | 2018-11-16 | 2024-07-16 | アムジエン・インコーポレーテツド | Ｋｒａｓ ｇ１２ｃ阻害剤化合物の重要な中間体の改良合成法 |
| JP7377679B2 (ja) | 2018-11-19 | 2023-11-10 | アムジエン・インコーポレーテツド | がん治療のためのｋｒａｓｇ１２ｃ阻害剤及び１種以上の薬学的に活性な追加の薬剤を含む併用療法 |
| AU2019384118B2 (en) | 2018-11-19 | 2025-06-12 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
| US11034710B2 (en) | 2018-12-04 | 2021-06-15 | Sumitomo Dainippon Pharma Oncology, Inc. | CDK9 inhibitors and polymorphs thereof for use as agents for treatment of cancer |
| AU2019401495B2 (en) | 2018-12-20 | 2025-06-26 | Amgen Inc. | Heteroaryl amides useful as KIF18A inhibitors |
| JP7686559B2 (ja) | 2018-12-20 | 2025-06-02 | アムジエン・インコーポレーテツド | Ｋｉｆ１８ａ阻害剤 |
| JP2022513967A (ja) | 2018-12-20 | 2022-02-09 | アムジエン・インコーポレーテツド | Ｋｉｆ１８ａ阻害剤として有用なヘテロアリールアミド |
| MA54543A (fr) | 2018-12-20 | 2022-03-30 | Amgen Inc | Inhibiteurs de kif18a |
| NL2022471B1 (en) | 2019-01-29 | 2020-08-18 | Vationpharma B V | Solid state forms of oclacitinib |
| MX2021010323A (es) | 2019-03-01 | 2021-12-10 | Revolution Medicines Inc | Compuestos bicíclicos de heterociclilo y usos de este. |
| MX2021010319A (es) | 2019-03-01 | 2021-12-10 | Revolution Medicines Inc | Compuestos biciclicos de heteroarilo y usos de estos. |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| WO2020191326A1 (en) | 2019-03-20 | 2020-09-24 | Sumitomo Dainippon Pharma Oncology, Inc. | Treatment of acute myeloid leukemia (aml) with venetoclax failure |
| EP3738593A1 (en) | 2019-05-14 | 2020-11-18 | Amgen, Inc | Dosing of kras inhibitor for treatment of cancers |
| WO2020236947A1 (en) | 2019-05-21 | 2020-11-26 | Amgen Inc. | Solid state forms |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| EP4007752B1 (en) | 2019-08-02 | 2025-09-24 | Amgen Inc. | Kif18a inhibitors |
| EP4007638A1 (en) | 2019-08-02 | 2022-06-08 | Amgen Inc. | Pyridine derivatives as kif18a inhibitors |
| EP4007753B1 (en) | 2019-08-02 | 2025-09-24 | Amgen Inc. | Kif18a inhibitors |
| EP4007756B1 (en) | 2019-08-02 | 2025-12-24 | Amgen Inc. | Kif18a inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CA3157361A1 (en) | 2019-10-14 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| EP4048671B1 (en) | 2019-10-24 | 2026-03-18 | Amgen Inc. | Pyridopyrimidine derivatives useful as kras g12c and kras g12d inhibitors in the treatment of cancer |
| TW202132316A (zh) | 2019-11-04 | 2021-09-01 | 美商銳新醫藥公司 | Ｒａｓ抑制劑 |
| AU2020377925A1 (en) | 2019-11-04 | 2022-05-05 | Revolution Medicines, Inc. | Ras inhibitors |
| IL322454A (en) | 2019-11-04 | 2025-09-01 | Revolution Medicines Inc | ras inhibitors |
| CN115038700B (zh) | 2019-11-08 | 2025-07-25 | 内尔维亚诺医疗科学公司 | 偕二取代的杂环化合物及其作为idh抑制剂的用途 |
| CA3156359A1 (en) | 2019-11-08 | 2021-05-14 | Adrian Liam Gill | Bicyclic heteroaryl compounds and uses thereof |
| JP2023501528A (ja) | 2019-11-14 | 2023-01-18 | アムジエン・インコーポレーテツド | Ｋｒａｓ ｇ１２ｃ阻害剤化合物の改善された合成 |
| JP7837865B2 (ja) | 2019-11-14 | 2026-03-31 | アムジエン・インコーポレーテツド | Ｋｒａｓ ｇ１２ｃ阻害剤化合物の改良合成法 |
| US11697648B2 (en) | 2019-11-26 | 2023-07-11 | Theravance Biopharma R&D Ip, Llc | Fused pyrimidine pyridinone compounds as JAK inhibitors |
| EP4065231A1 (en) | 2019-11-27 | 2022-10-05 | Revolution Medicines, Inc. | Covalent ras inhibitors and uses thereof |
| JP7832891B2 (ja) | 2019-12-04 | 2026-03-18 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤の誘導体 |
| CA3163875A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| WO2021142026A1 (en) | 2020-01-07 | 2021-07-15 | Revolution Medicines, Inc. | Shp2 inhibitor dosing and methods of treating cancer |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| CN113801139A (zh) * | 2020-06-12 | 2021-12-17 | 华东理工大学 | 作为rsk抑制剂的嘧啶并恶嗪衍生物及其应用 |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| IL299131A (en) | 2020-06-18 | 2023-02-01 | Revolution Medicines Inc | Methods for delaying, preventing and treating acquired resistance to RAS inhibitors |
| US20250195521A1 (en) | 2020-09-03 | 2025-06-19 | Revolution Medicines, Inc. | Use of sos1 inhibitors to treat malignancies with shp2 mutations |
| CA3194067A1 (en) | 2020-09-15 | 2022-03-24 | Revolution Medicines, Inc. | Ras inhibitors |
| JP7849366B2 (ja) | 2020-12-22 | 2026-04-21 | キル・レガー・セラピューティクス・インコーポレーテッド | Ｓｏｓ１阻害剤およびその使用 |
| WO2022177302A1 (ko) * | 2021-02-17 | 2022-08-25 | 보령제약 주식회사 | Dna-pk 억제 활성을 갖는 피리미딘-융합 고리 화합물 및 이의 용도 |
| WO2022221170A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| TW202309052A (zh) | 2021-05-05 | 2023-03-01 | 美商銳新醫藥公司 | Ｒａｓ抑制劑 |
| KR20240017811A (ko) | 2021-05-05 | 2024-02-08 | 레볼루션 메디슨즈, 인크. | 암의 치료를 위한 ras 억제제 |
| JP2024516450A (ja) | 2021-05-05 | 2024-04-15 | レボリューション メディシンズ インコーポレイテッド | 共有結合性ｒａｓ阻害剤及びその使用 |
| US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| CN119212994A (zh) | 2021-12-17 | 2024-12-27 | 建新公司 | 作为shp2抑制剂的吡唑并吡嗪化合物 |
| EP4227307A1 (en) | 2022-02-11 | 2023-08-16 | Genzyme Corporation | Pyrazolopyrazine compounds as shp2 inhibitors |
| KR20240156373A (ko) | 2022-03-07 | 2024-10-29 | 암젠 인크 | 4-메틸-2-프로판-2-일-피리딘-3-카르보니트릴의 제조 방법 |
| JP2025510572A (ja) | 2022-03-08 | 2025-04-15 | レボリューション メディシンズ インコーポレイテッド | 免疫不応性肺癌を治療するための方法 |
| WO2023240263A1 (en) | 2022-06-10 | 2023-12-14 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
| AU2023358792A1 (en) | 2022-10-14 | 2025-04-17 | Black Diamond Therapeutics, Inc. | Methods of treating cancers using isoquinoline or 6-aza-quinoline derivatives |
| AU2024241633A1 (en) | 2023-03-30 | 2025-11-06 | Revolution Medicines, Inc. | Compositions for inducing ras gtp hydrolysis and uses thereof |
| AR132338A1 (es) | 2023-04-07 | 2025-06-18 | Revolution Medicines Inc | Inhibidores de ras |
| CR20250420A (es) | 2023-04-07 | 2025-11-20 | Revolution Medicines Inc | Inhibidores macrocíclicos de ras |
| CN121100123A (zh) | 2023-04-14 | 2025-12-09 | 锐新医药公司 | Ras抑制剂的结晶形式 |
| CN121464140A (zh) | 2023-04-14 | 2026-02-03 | 锐新医药公司 | Ras抑制剂的结晶形式、含有其的组合物及其使用方法 |
| TW202508595A (zh) | 2023-05-04 | 2025-03-01 | 美商銳新醫藥公司 | 用於ｒａｓ相關疾病或病症之組合療法 |
| US20250049810A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| AU2024360465A1 (en) | 2023-10-12 | 2026-04-09 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
| TW202542151A (zh) | 2023-12-22 | 2025-11-01 | 美商銳格醫藥有限公司 | Ｓｏｓ１抑制劑及其用途 |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| TW202547461A (zh) | 2024-05-17 | 2025-12-16 | 美商銳新醫藥公司 | Ｒａｓ抑制劑 |
| WO2025255438A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2025265060A1 (en) | 2024-06-21 | 2025-12-26 | Revolution Medicines, Inc. | Therapeutic compositions and methods for managing treatment-related effects |
| WO2026006747A1 (en) | 2024-06-28 | 2026-01-02 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026015801A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015825A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Use of ras inhibitor for treating pancreatic cancer |
| WO2026015796A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015790A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026050446A1 (en) | 2024-08-29 | 2026-03-05 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026072904A2 (en) | 2024-09-26 | 2026-04-02 | Revolution Medicines, Inc. | Compositions and methods for treating lung cancer |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL60307A (en) * | 1979-06-14 | 1984-02-29 | Wellcome Found | 2,4-diamino-6-(dimethoxybenzyl)-5-methylpyrido-(2,3-d)pyrimidines,their preparation and pharmaceutical compositions containing them |
| EP0278686A1 (en) * | 1987-02-07 | 1988-08-17 | The Wellcome Foundation Limited | Pyridopyrimidines methods for their preparation and pharmaceutical formulations thereof |
| SG64322A1 (en) * | 1991-05-10 | 1999-04-27 | Rhone Poulenc Rorer Int | Bis mono and bicyclic aryl and heteroaryl compounds which inhibit egf and/or pdgf receptor tyrosine kinase |
| US5426110A (en) * | 1993-10-06 | 1995-06-20 | Eli Lilly And Company | Pyrimidinyl-glutamic acid derivatives |
| GB9325217D0 (en) * | 1993-12-09 | 1994-02-09 | Zeneca Ltd | Pyrimidine derivatives |
| PL181893B1 (pl) * | 1994-11-14 | 2001-10-31 | Warner Lambert Co | Zwiazki bedace pochodnymi pirymidyny i naftyrydyny oraz preparat farmaceutyczny zawierajacy je PL PL PL |
| IL117923A (en) * | 1995-05-03 | 2000-06-01 | Warner Lambert Co | Anti-cancer pharmaceutical compositions containing polysubstituted pyrido¬2,3-d¾pyrimidine derivatives and certain such novel compounds |
| JP2001511764A (ja) * | 1996-04-12 | 2001-08-14 | 住友製薬株式会社 | ピペリジニルピリミジン誘導体 |
-
1998
- 1998-01-26 WO PCT/US1998/001343 patent/WO1998033798A2/en not_active Ceased
- 1998-01-26 BR BR9807305-2A patent/BR9807305A/pt not_active Application Discontinuation
- 1998-01-26 JP JP53297198A patent/JP2001509805A/ja not_active Ceased
- 1998-01-26 AU AU66480/98A patent/AU749750B2/en not_active Ceased
- 1998-01-26 EP EP98908442A patent/EP0964864B1/en not_active Expired - Lifetime
- 1998-01-26 AT AT98908442T patent/ATE391719T1/de not_active IP Right Cessation
- 1998-01-26 DE DE69839338T patent/DE69839338T2/de not_active Expired - Fee Related
- 1998-01-26 KR KR1019997007010A patent/KR20000070751A/ko not_active Ceased
- 1998-01-26 ES ES98908442T patent/ES2301194T3/es not_active Expired - Lifetime
- 1998-01-26 CA CA002271157A patent/CA2271157A1/en not_active Abandoned
- 1998-02-05 HR HR60/069,743A patent/HRP980060A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR9807305A (pt) | 2000-05-02 |
| CA2271157A1 (en) | 1998-08-06 |
| ES2301194T3 (es) | 2008-06-16 |
| DE69839338T2 (de) | 2008-07-10 |
| DE69839338D1 (de) | 2008-05-21 |
| EP0964864A2 (en) | 1999-12-22 |
| WO1998033798A3 (en) | 1998-11-05 |
| ATE391719T1 (de) | 2008-04-15 |
| JP2001509805A (ja) | 2001-07-24 |
| EP0964864B1 (en) | 2008-04-09 |
| AU6648098A (en) | 1998-08-25 |
| HRP980060A2 (en) | 1999-06-30 |
| AU749750B2 (en) | 2002-07-04 |
| WO1998033798A2 (en) | 1998-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6498163B1 (en) | Pyrido[2,3-D]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation | |
| KR20000070751A (ko) | 세포 증식 억제제로서의 피리도[2,3-ｄ]피리미딘 및 4-아미노피리미딘 | |
| US20040224958A1 (en) | Pyridopyrimidinone derivatives for treatment of neurodegenerative disease | |
| AU763839B2 (en) | Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation | |
| KR100663773B1 (ko) | 피리미딘 화합물 | |
| US20070049600A1 (en) | Pteridinones as kinase inhibitors | |
| US20040044012A1 (en) | Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation | |
| SK281724B6 (sk) | 6-arylpyrido[2,3-d]pyrimidíny, ich použitie a farmaceutické prostriedky na ich báze | |
| SK141097A3 (en) | Pyrido[2,3-d]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation | |
| CA3147422A1 (en) | Inhibitors of cyclin-dependent kinases | |
| EP1195378B1 (en) | Pyridotriazines and pyridopyridazines | |
| EP1806348A2 (en) | Pyrido (2,3-D)Pyrimidines as inhibitors of cellular proliferation | |
| MXPA99004584A (en) | Pyrido [2,3-d]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation | |
| EP1801112A1 (en) | Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation | |
| MXPA00010738A (en) | Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation | |
| OA11554A (en) | Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation. | |
| CZ20004246A3 (cs) | Bicyklické pyrimidiny a bicyklické 3,4- dihydropyrimidiny jako inhibitory buněčné proliferace |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 19990804 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20030125 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20050120 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20050531 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20050120 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |