NO310110B1 - Pyrido(2,3-d)-pyrimidiner for inhibering av protein tyrosin- kinasebetinget cellul¶r formering, samt farmasöytisk preparatinneholdende en slik forbindelse - Google Patents

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Publication number

NO310110B1

NO310110B1 NO19975033A NO975033A NO310110B1 NO 310110 B1 NO310110 B1 NO 310110B1 NO 19975033 A NO19975033 A NO 19975033A NO 975033 A NO975033 A NO 975033A NO 310110 B1 NO310110 B1 NO 310110B1

Authority

NO

Norway

Prior art keywords

pyrido

pyrimidin

dichlorophenyl

methyl

ethyl

Prior art date

1995-05-03

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 132
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 title claims abstract description 15
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 title claims abstract description 15
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
• 230000004663 cell proliferation Effects 0.000 title abstract description 7
• 230000005764 inhibitory process Effects 0.000 title description 5
• 159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 title description 5
• 230000001419 dependent effect Effects 0.000 title 1
• 239000000203 mixture Substances 0.000 claims description 123
• -1 hydroxy, carboxy Chemical group 0.000 claims description 60
• 239000002253 acid Substances 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 125000004076 pyridyl group Chemical class 0.000 claims description 11
• GACTZGDNEYDRRN-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-ethyl-2-methylsulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(S(C)(=O)=O)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl GACTZGDNEYDRRN-UHFFFAOYSA-N 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• KIOLKAOBNXSWMM-UHFFFAOYSA-N 2-[2-amino-6-(2,6-dichlorophenyl)-7-oxopyrido[2,3-d]pyrimidin-8-yl]acetic acid Chemical compound O=C1N(CC(O)=O)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl KIOLKAOBNXSWMM-UHFFFAOYSA-N 0.000 claims description 3
• ANZYDUHZJJDQHA-UHFFFAOYSA-N 2-anilino-6-(3,5-dimethylphenyl)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3C=C(C)C=C(C)C=3)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 ANZYDUHZJJDQHA-UHFFFAOYSA-N 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical class 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 150000004702 methyl esters Chemical class 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• AQUXBIDNWAFZLO-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-(2-methylpropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC(C)C)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl AQUXBIDNWAFZLO-UHFFFAOYSA-N 0.000 claims description 2
• NRIXVSKQGIVOTD-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-(3-phenylpropyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCCC=2C=CC=CC=2)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl NRIXVSKQGIVOTD-UHFFFAOYSA-N 0.000 claims description 2
• XMTYXUJCIGTOHH-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-(pyridin-4-ylmethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC=2C=CN=CC=2)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl XMTYXUJCIGTOHH-UHFFFAOYSA-N 0.000 claims description 2
• ZQGDTAGYPZFLIF-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-[(4-methoxyphenyl)methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(C=2C(=CC=CC=2Cl)Cl)=CC2=CN=C(N)N=C21 ZQGDTAGYPZFLIF-UHFFFAOYSA-N 0.000 claims description 2
• GQDVHGJYRQHKDS-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-[3-(dimethylamino)propyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCCN(C)C)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl GQDVHGJYRQHKDS-UHFFFAOYSA-N 0.000 claims description 2
• RARNNEKMSBLJMX-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl RARNNEKMSBLJMX-UHFFFAOYSA-N 0.000 claims description 2
• URPMELUGCLZPCA-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-propylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCC)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl URPMELUGCLZPCA-UHFFFAOYSA-N 0.000 claims description 2
• HRIBYPMDWNLUHY-UHFFFAOYSA-N 2-amino-8-[(3-bromophenyl)methyl]-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC=2C=C(Br)C=CC=2)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl HRIBYPMDWNLUHY-UHFFFAOYSA-N 0.000 claims description 2
• PEKQQOAQBPEQDZ-UHFFFAOYSA-N 2-amino-8-benzyl-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC=2C=CC=CC=2)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl PEKQQOAQBPEQDZ-UHFFFAOYSA-N 0.000 claims description 2
• ILHLRWXGPLAJKK-UHFFFAOYSA-N 2-anilino-6-(2-bromo-6-chlorophenyl)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3C(=CC=CC=3Cl)Br)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 ILHLRWXGPLAJKK-UHFFFAOYSA-N 0.000 claims description 2
• CVZGVJVVPUMWDD-UHFFFAOYSA-N 2-anilino-8-ethyl-6-naphthalen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3C=C4C=CC=CC4=CC=3)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 CVZGVJVVPUMWDD-UHFFFAOYSA-N 0.000 claims description 2
• HSEYKDNBMMUBTH-UHFFFAOYSA-N 2-anilino-8-ethyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3C=CC=CC=3)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 HSEYKDNBMMUBTH-UHFFFAOYSA-N 0.000 claims description 2
• RBURTLAMOSHNGX-UHFFFAOYSA-N 3-[[6-(2,6-dichlorophenyl)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]benzoic acid Chemical compound N=1C=C2C=C(C=3C(=CC=CC=3Cl)Cl)C(=O)N(C)C2=NC=1NC1=CC=CC(C(O)=O)=C1 RBURTLAMOSHNGX-UHFFFAOYSA-N 0.000 claims description 2
• BLSJVNBQZLDNRJ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[2-(diethylamino)ethoxy]-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(OCCN(CC)CC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl BLSJVNBQZLDNRJ-UHFFFAOYSA-N 0.000 claims description 2
• OBHFIWYKTXHXKN-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-8-ethyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-imine Chemical compound N=C1N(CC)C2=NC(SC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl OBHFIWYKTXHXKN-UHFFFAOYSA-N 0.000 claims description 2
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
• NXHGGDQABDGSFK-UHFFFAOYSA-N ethyl 4-[4-[[6-(2,6-dichlorophenyl)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]phenyl]butanoate Chemical compound C1=CC(CCCC(=O)OCC)=CC=C1NC1=NC=C(C=C(C=2C(=CC=CC=2Cl)Cl)C(=O)N2C)C2=N1 NXHGGDQABDGSFK-UHFFFAOYSA-N 0.000 claims description 2
• KNIFQDAVGJMBRW-UHFFFAOYSA-N methyl 2-[2-amino-6-(2,6-dichlorophenyl)-7-oxopyrido[2,3-d]pyrimidin-8-yl]acetate Chemical compound O=C1N(CC(=O)OC)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl KNIFQDAVGJMBRW-UHFFFAOYSA-N 0.000 claims description 2
• NUSXVSHQHATUGJ-UHFFFAOYSA-N methyl 2-[4-[[6-(2,6-dichlorophenyl)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1NC1=NC=C(C=C(C=2C(=CC=CC=2Cl)Cl)C(=O)N2C)C2=N1 NUSXVSHQHATUGJ-UHFFFAOYSA-N 0.000 claims description 2
• FYDHIIMQQARSLH-UHFFFAOYSA-N n-[6-(2,6-dichlorophenyl)-7-imino-8-methylpyrido[2,3-d]pyrimidin-2-yl]-n',n'-diethylpropane-1,3-diamine Chemical compound N=C1N(C)C2=NC(NCCCN(CC)CC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl FYDHIIMQQARSLH-UHFFFAOYSA-N 0.000 claims description 2
• AGZYPNVWEUGADC-UHFFFAOYSA-N n-[6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-ylidene]acetamide Chemical compound CC(=O)N=C1N(C)C2=NC(SC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl AGZYPNVWEUGADC-UHFFFAOYSA-N 0.000 claims description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical group O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 3
• GWLRNLPJEBRBCZ-UHFFFAOYSA-N 6-[[6-(2,6-dichlorophenyl)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]hexanoic acid Chemical compound O=C1N(C)C2=NC(NCCCCCC(O)=O)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl GWLRNLPJEBRBCZ-UHFFFAOYSA-N 0.000 claims 2
• 239000013543 active substance Substances 0.000 claims 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
• BGDZDAYKHROKLL-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylamino)-6-(2,6-dichlorophenyl)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4OCOC4=CC=3)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl BGDZDAYKHROKLL-UHFFFAOYSA-N 0.000 claims 1
• QOSLUZXSYUGPOU-UHFFFAOYSA-N 2-(butylamino)-6-(2,6-dichlorophenyl)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NCCCC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl QOSLUZXSYUGPOU-UHFFFAOYSA-N 0.000 claims 1
• AMKNQROTNAOJQE-UHFFFAOYSA-N 2-[4-[[6-(2,6-dichlorophenyl)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]phenyl]acetic acid Chemical compound N=1C=C2C=C(C=3C(=CC=CC=3Cl)Cl)C(=O)N(C)C2=NC=1NC1=CC=C(CC(O)=O)C=C1 AMKNQROTNAOJQE-UHFFFAOYSA-N 0.000 claims 1
• WJUIUBDNROOVQI-UHFFFAOYSA-N 2-amino-6-(2,6-dichlorophenyl)-8-methylpyrido[2,3-d]pyrimidine-7-thione Chemical compound S=C1N(C)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl WJUIUBDNROOVQI-UHFFFAOYSA-N 0.000 claims 1
• ZRNVMCXGAZFVMN-UHFFFAOYSA-N 2-amino-8-butyl-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCCC)C2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl ZRNVMCXGAZFVMN-UHFFFAOYSA-N 0.000 claims 1
• APNFLKHAUOZQEF-UHFFFAOYSA-N 2-amino-8-methyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C1=CC=CC=C1 APNFLKHAUOZQEF-UHFFFAOYSA-N 0.000 claims 1
• XZBKAAPFQAVYSN-UHFFFAOYSA-N 2-anilino-6-(2,6-dichlorophenyl)-8-ethylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3C(=CC=CC=3Cl)Cl)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 XZBKAAPFQAVYSN-UHFFFAOYSA-N 0.000 claims 1
• AHLVFUBXCLYYOB-UHFFFAOYSA-N 2-anilino-8-ethyl-6-pyridin-4-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3C=CN=CC=3)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 AHLVFUBXCLYYOB-UHFFFAOYSA-N 0.000 claims 1
• PHQNMSXJZFHWIT-UHFFFAOYSA-N 2-anilino-8-ethyl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3SC=CC=3)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 PHQNMSXJZFHWIT-UHFFFAOYSA-N 0.000 claims 1
• CBIJGNHFFWAGLZ-UHFFFAOYSA-N 4-[4-[[6-(2,6-dichlorophenyl)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]phenyl]butanoic acid Chemical compound N=1C=C2C=C(C=3C(=CC=CC=3Cl)Cl)C(=O)N(C)C2=NC=1NC1=CC=C(CCCC(O)=O)C=C1 CBIJGNHFFWAGLZ-UHFFFAOYSA-N 0.000 claims 1
• BLRBESAVRFJPCA-UHFFFAOYSA-N 4-[[6-(2,6-dichlorophenyl)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]benzoic acid Chemical compound N=1C=C2C=C(C=3C(=CC=CC=3Cl)Cl)C(=O)N(C)C2=NC=1NC1=CC=C(C(O)=O)C=C1 BLRBESAVRFJPCA-UHFFFAOYSA-N 0.000 claims 1
• GOWKLVGETIDUTE-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(2-hydroxyethylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NCCO)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl GOWKLVGETIDUTE-UHFFFAOYSA-N 0.000 claims 1
• FCUQJIQLHXSQHY-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(2-methoxyanilino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC=CC=C1NC1=NC=C(C=C(C=2C(=CC=CC=2Cl)Cl)C(=O)N2C)C2=N1 FCUQJIQLHXSQHY-UHFFFAOYSA-N 0.000 claims 1
• RYCIKEDAOOTILW-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(3,5-dimethoxyanilino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC(OC)=CC(NC=2N=C3N(C)C(=O)C(C=4C(=CC=CC=4Cl)Cl)=CC3=CN=2)=C1 RYCIKEDAOOTILW-UHFFFAOYSA-N 0.000 claims 1
• YLOVBNCIDYKIDW-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(3-hydroxyanilino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(C=3C(=CC=CC=3Cl)Cl)C(=O)N(C)C2=NC=1NC1=CC=CC(O)=C1 YLOVBNCIDYKIDW-UHFFFAOYSA-N 0.000 claims 1
• IDCFPJHKTOPZHU-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(3-methoxyanilino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC=CC(NC=2N=C3N(C)C(=O)C(C=4C(=CC=CC=4Cl)Cl)=CC3=CN=2)=C1 IDCFPJHKTOPZHU-UHFFFAOYSA-N 0.000 claims 1
• PBDZUUYDHCFPJM-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(4-methoxy-3-methylanilino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(C)C(OC)=CC=C1NC1=NC=C(C=C(C=2C(=CC=CC=2Cl)Cl)C(=O)N2C)C2=N1 PBDZUUYDHCFPJM-UHFFFAOYSA-N 0.000 claims 1
• ZDVPZVBAWYNOOH-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(4-methoxyanilino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=C(C=2C(=CC=CC=2Cl)Cl)C(=O)N2C)C2=N1 ZDVPZVBAWYNOOH-UHFFFAOYSA-N 0.000 claims 1
• JBLZRKIIUFHPCO-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(dimethylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(N(C)C)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl JBLZRKIIUFHPCO-UHFFFAOYSA-N 0.000 claims 1
• FNBJMQJWFBTPGJ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-(ethylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NCC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl FNBJMQJWFBTPGJ-UHFFFAOYSA-N 0.000 claims 1
• NBPINIBREWXSRV-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[(6-methoxypyridin-3-yl)amino]-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=NC(OC)=CC=C1NC1=NC=C(C=C(C=2C(=CC=CC=2Cl)Cl)C(=O)N2C)C2=N1 NBPINIBREWXSRV-UHFFFAOYSA-N 0.000 claims 1
• KKCRFZPDHMZGRA-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[2-(3,4-dimethoxyphenyl)ethylamino]-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=NC=C(C=C(C=2C(=CC=CC=2Cl)Cl)C(=O)N2C)C2=N1 KKCRFZPDHMZGRA-UHFFFAOYSA-N 0.000 claims 1
• MZECPFJWRHJKQC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N=C3N(C)C(=O)C(C=4C(=CC=CC=4Cl)Cl)=CC3=CN=2)CC1 MZECPFJWRHJKQC-UHFFFAOYSA-N 0.000 claims 1
• IFPPYSWJNWHOLQ-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-[4-[2-(diethylamino)ethoxy]anilino]-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(C=C(C=2C(=CC=CC=2Cl)Cl)C(=O)N2C)C2=N1 IFPPYSWJNWHOLQ-UHFFFAOYSA-N 0.000 claims 1
• ZIQFYVPVJZEOFS-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-{[3-(hydroxymethyl)phenyl]amino}-8-methylpyrido[2,3-d]pyrimidin-7(8h)-one Chemical compound N=1C=C2C=C(C=3C(=CC=CC=3Cl)Cl)C(=O)N(C)C2=NC=1NC1=CC=CC(CO)=C1 ZIQFYVPVJZEOFS-UHFFFAOYSA-N 0.000 claims 1
• VZGPSGJALDBJQT-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-7-imino-8-methyl-1H-pyrido[2,3-d]pyrimidin-2-one Chemical compound Cn1c2nc(O)ncc2cc(-c2c(Cl)cccc2Cl)c1=N VZGPSGJALDBJQT-UHFFFAOYSA-N 0.000 claims 1
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