HRP980060A2

HRP980060A2 - Pyrido/2,3-d/pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation

Pyrido/2,3-d/pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation

Info

Publication number: HRP980060A2
Authority: HR; Croatia
Prior art keywords: pyrimidin; pyrido; phenylamino; ethyl; piperidin
Prior art date: 1997-02-05

Application number

HR60/069,743A

Other languages

English (en)

Croatian (hr)

Inventor

Mark R Barvian

Original Assignee

Mark R. Barvian

Priority date

1997-02-05

Filing date

1998-02-05

Publication date

1999-06-30

1998-02-05 Application filed by Mark R. Barvian filed Critical Mark R. Barvian

1999-06-30 Publication of HRP980060A2 publication Critical patent/HRP980060A2/hr

Links

239000003112 inhibitor Substances 0.000 title abstract description 10
150000005007 4-aminopyrimidines Chemical class 0.000 title abstract description 4
230000004663 cell proliferation Effects 0.000 title description 3
150000003230 pyrimidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 129
125000000217 alkyl group Chemical group 0.000 claims abstract description 42
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 24
229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
206010028980 Neoplasm Diseases 0.000 claims abstract description 19
208000037265 diseases, disorders, signs and symptoms 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
108091000080 Phosphotransferase Proteins 0.000 claims abstract description 13
201000011510 cancer Diseases 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
102000020233 phosphotransferase Human genes 0.000 claims abstract description 13
230000001404 mediated effect Effects 0.000 claims abstract description 10
230000002062 proliferating effect Effects 0.000 claims abstract description 10
208000037803 restenosis Diseases 0.000 claims abstract description 10
239000003102 growth factor Substances 0.000 claims abstract description 8
150000002431 hydrogen Chemical class 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
239000003085 diluting agent Substances 0.000 claims abstract description 6
239000003937 drug carrier Substances 0.000 claims abstract description 6
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
-1 8-ethyl-3-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one Chemical compound 0.000 claims description 131
239000000203 mixture Substances 0.000 claims description 63
238000000034 method Methods 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 25
229910052757 nitrogen Inorganic materials 0.000 claims description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 11
150000002825 nitriles Chemical class 0.000 claims description 11
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
238000009472 formulation Methods 0.000 claims description 10
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
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 9
201000001320 Atherosclerosis Diseases 0.000 claims description 9
101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims description 9
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 9
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 9
101150073031 cdk2 gene Proteins 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
230000002401 inhibitory effect Effects 0.000 claims description 9
230000035755 proliferation Effects 0.000 claims description 9
125000000547 substituted alkyl group Chemical group 0.000 claims description 9
108050007372 Fibroblast Growth Factor Proteins 0.000 claims description 8
102000018233 Fibroblast Growth Factor Human genes 0.000 claims description 8
101100295741 Gallus gallus COR4 gene Proteins 0.000 claims description 8
108010038512 Platelet-Derived Growth Factor Proteins 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229940126864 fibroblast growth factor Drugs 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
150000003573 thiols Chemical class 0.000 claims description 8
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 7
102000010780 Platelet-Derived Growth Factor Human genes 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
210000002464 muscle smooth vascular Anatomy 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical class [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000004494 ethyl ester group Chemical group 0.000 claims description 6
239000001301 oxygen Chemical class 0.000 claims description 6
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 5
101150012716 CDK1 gene Proteins 0.000 claims description 5
101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
230000005764 inhibitory process Effects 0.000 claims description 5
150000002829 nitrogen Chemical class 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000004001 thioalkyl group Chemical group 0.000 claims description 5
239000008096 xylene Substances 0.000 claims description 5
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
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 4
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 4
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 4
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 4
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 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
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 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
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 3
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 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
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 3
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 3
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 3
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 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
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 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
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 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
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
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 3
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 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
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 3
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 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
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 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
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
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 3
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 3
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 3
102000016736 Cyclin Human genes 0.000 claims description 3
108050006400 Cyclin Proteins 0.000 claims description 3
101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 3
102000001253 Protein Kinase Human genes 0.000 claims description 3
239000005864 Sulphur Chemical class 0.000 claims description 3
101100273808 Xenopus laevis cdk1-b gene Proteins 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
230000002980 postoperative effect Effects 0.000 claims description 3
108060006633 protein kinase Proteins 0.000 claims description 3
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
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 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
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
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 description 2
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 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
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 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
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
WCVKOGFMMGNKBV-UHFFFAOYSA-N 2-anilino-8-(oxiran-2-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CC3OC3)C(=O)C=CC2=CN=C1NC1=CC=CC=C1 WCVKOGFMMGNKBV-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
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
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
239000011593 sulfur Chemical class 0.000 claims description 2
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