CA2397961C - Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors - Google Patents

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Publication number

CA2397961C

CA2397961C CA002397961A CA2397961A CA2397961C CA 2397961 C CA2397961 C CA 2397961C CA 002397961 A CA002397961 A CA 002397961A CA 2397961 A CA2397961 A CA 2397961A CA 2397961 C CA2397961 C CA 2397961C

Authority

CA

Canada

Prior art keywords

pyrido

pyrimidin

urea

phenylamino

piperazin

Prior art date

2000-01-25

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.)

Expired - Fee Related

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• CIPO
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• QRRCMVPZJCHBLQ-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine-2,7-diamine Chemical compound C1=NC(N)=NC2=NC(N)=CC=C21 QRRCMVPZJCHBLQ-UHFFFAOYSA-N 0.000 title description 4
• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 145
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 57
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 52
• 150000002367 halogens Chemical group 0.000 claims abstract description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 34
• 239000001257 hydrogen Substances 0.000 claims abstract description 34
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 27
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 25
• 125000003118 aryl group Chemical group 0.000 claims abstract description 24
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 18
• 201000011510 cancer Diseases 0.000 claims abstract description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 230000002062 proliferating effect Effects 0.000 claims abstract description 10
• 230000001404 mediated effect Effects 0.000 claims abstract description 9
• 208000037803 restenosis Diseases 0.000 claims abstract description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
• 101150020251 NR13 gene Proteins 0.000 claims abstract 3
• 239000004202 carbamide Substances 0.000 claims description 80
• -1 nitro, carboxy Chemical group 0.000 claims description 73
• 229910052760 oxygen Inorganic materials 0.000 claims description 35
• 125000005842 heteroatom Chemical group 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 28
• 229910052717 sulfur Inorganic materials 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 21
• 238000002360 preparation method Methods 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
• 101150073031 cdk2 gene Proteins 0.000 claims description 15
• 102000004190 Enzymes Human genes 0.000 claims description 12
• 108090000790 Enzymes Proteins 0.000 claims description 12
• 230000002401 inhibitory effect Effects 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 10
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 10
• 125000002837 carbocyclic group Chemical group 0.000 claims description 10
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 8
• ZDQUGBAOJVAHFP-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(NC(=O)NC(C)(C)C)=N2)C2=N1 ZDQUGBAOJVAHFP-UHFFFAOYSA-N 0.000 claims description 7
• 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims description 7
• 230000004663 cell proliferation Effects 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 239000003102 growth factor Substances 0.000 claims description 6
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• XSDIGEOCQDHWOK-UHFFFAOYSA-N 1-[6-cyano-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound N=1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C=C(C#N)C=1NC(=O)NC1CCCCC1 XSDIGEOCQDHWOK-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 210000004509 vascular smooth muscle cell Anatomy 0.000 claims description 4
• LWWHQXYBJDKMHB-UHFFFAOYSA-N 1-(4-hydroxycyclohexyl)-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1CC(O)CCC1NC(=O)NC1=CC=C(C=NC(NC=2C=CC(=CC=2)N2CCNCC2)=N2)C2=N1 LWWHQXYBJDKMHB-UHFFFAOYSA-N 0.000 claims description 3
• VGFQMCUDJBVYIU-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)-3-chloroanilino]pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound C1CN(C(=O)C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C(C=CC(NC(=O)NC(C)(C)C)=N2)C2=N1 VGFQMCUDJBVYIU-UHFFFAOYSA-N 0.000 claims description 3
• BWORXTLBVMGUGI-UHFFFAOYSA-N 1-[6-bromo-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound N=1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(Br)C=1NC(=O)NC1CCCCC1 BWORXTLBVMGUGI-UHFFFAOYSA-N 0.000 claims description 3
• UXBCLFZSEPAATK-UHFFFAOYSA-N 1-[6-chloro-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound N=1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(Cl)C=1NC(=O)NC1CCCCC1 UXBCLFZSEPAATK-UHFFFAOYSA-N 0.000 claims description 3
• BVMSORLIMAKEEG-UHFFFAOYSA-N 1-cyclohexyl-3-[2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1=CC(F)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 BVMSORLIMAKEEG-UHFFFAOYSA-N 0.000 claims description 3
• HSXKXMHAELFQJA-UHFFFAOYSA-N 1-cyclohexyl-3-[2-(4-sulfamoylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 HSXKXMHAELFQJA-UHFFFAOYSA-N 0.000 claims description 3
• ZMWBWZXAOFKNCZ-UHFFFAOYSA-N 1-cyclohexyl-3-[6-fluoro-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(F)C=1NC(=O)NC1CCCCC1 ZMWBWZXAOFKNCZ-UHFFFAOYSA-N 0.000 claims description 3
• MEPIXWYYOTZYNT-UHFFFAOYSA-N 1-ethyl-3-[5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NCC)=CC(C)=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 MEPIXWYYOTZYNT-UHFFFAOYSA-N 0.000 claims description 3
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 101150012716 CDK1 gene Proteins 0.000 claims description 3
• PGQSLDLNYLTRIQ-UHFFFAOYSA-N [5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C=C2C(C)=CC(NC(N)=O)=NC2=NC=1NC(C=C1)=CC=C1N1CCNCC1 PGQSLDLNYLTRIQ-UHFFFAOYSA-N 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• IZPRSDVSVWVZOM-UHFFFAOYSA-N 1,1-bis(2-hydroxyethyl)-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)N(CCO)CCO)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 IZPRSDVSVWVZOM-UHFFFAOYSA-N 0.000 claims description 2
• MRBJJIIFXAMERI-UHFFFAOYSA-N 1-(2-anilinopyrido[2,3-d]pyrimidin-7-yl)-3-tert-butylurea Chemical compound N=1C2=NC(NC(=O)NC(C)(C)C)=CC=C2C=NC=1NC1=CC=CC=C1 MRBJJIIFXAMERI-UHFFFAOYSA-N 0.000 claims description 2
• XFILUMCRLWWGHF-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C=C2C(C)=CC(NC(=O)NCCO)=NC2=NC=1NC(C=C1)=CC=C1N1CCNCC1 XFILUMCRLWWGHF-UHFFFAOYSA-N 0.000 claims description 2
• OJAWTIFCYCKDIF-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[5-methyl-2-(pyridin-4-ylamino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C=C2C(C)=CC(NC(=O)NCCO)=NC2=NC=1NC1=CC=NC=C1 OJAWTIFCYCKDIF-UHFFFAOYSA-N 0.000 claims description 2
• YACCIEHTQKOSOZ-UHFFFAOYSA-N 1-(3-hydroxypropyl)-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NCCCO)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 YACCIEHTQKOSOZ-UHFFFAOYSA-N 0.000 claims description 2
• QPUDAOMKURLGLK-UHFFFAOYSA-N 1-(4-aminocyclohexyl)-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1CC(N)CCC1NC(=O)NC1=CC=C(C=NC(NC=2C=CC(=CC=2)N2CCNCC2)=N2)C2=N1 QPUDAOMKURLGLK-UHFFFAOYSA-N 0.000 claims description 2
• OHOPJOZAUWXPDP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[2-(4-fluoro-3-methylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1=C(F)C(C)=CC(NC=2N=C3N=C(NC(=O)NC=4C=CC(Cl)=CC=4)C=CC3=CN=2)=C1 OHOPJOZAUWXPDP-UHFFFAOYSA-N 0.000 claims description 2
• YFNIERFVGYMMPV-IBGZPJMESA-N 1-[(2r)-1-hydroxy-3-methylbutan-2-yl]-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)N[C@@H](CO)C(C)C)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 YFNIERFVGYMMPV-IBGZPJMESA-N 0.000 claims description 2
• JYSYXVGVSGEKJX-UHFFFAOYSA-N 1-[2-(3-chloro-4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-(2-hydroxyethyl)urea Chemical compound N=1C2=NC(NC(=O)NCCO)=CC=C2C=NC=1NC(C=C1Cl)=CC=C1N1CCNCC1 JYSYXVGVSGEKJX-UHFFFAOYSA-N 0.000 claims description 2
• OAZKKGFIMGBLNP-UHFFFAOYSA-N 1-[2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-(2-hydroxyethyl)urea Chemical compound N=1C2=NC(NC(=O)NCCO)=CC=C2C=NC=1NC1=CC=C(F)C=C1 OAZKKGFIMGBLNP-UHFFFAOYSA-N 0.000 claims description 2
• IWNKWJVEAVWLNF-UHFFFAOYSA-N 1-[2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-(3-morpholin-4-ylpropyl)urea Chemical compound C1=CC(F)=CC=C1NC1=NC=C(C=CC(NC(=O)NCCCN2CCOCC2)=N2)C2=N1 IWNKWJVEAVWLNF-UHFFFAOYSA-N 0.000 claims description 2
• KEDVKYIYPFUXJF-UHFFFAOYSA-N 1-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-propan-2-ylurea Chemical compound N=1C2=NC(NC(=O)NC(C)C)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 KEDVKYIYPFUXJF-UHFFFAOYSA-N 0.000 claims description 2
• CSHJWZUPBIECMW-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NCCN(C)C)=CC=C2C=NC=1NC1=CC=C(F)C=C1 CSHJWZUPBIECMW-UHFFFAOYSA-N 0.000 claims description 2
• XNJIKCCLIKXVKC-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NCCN(C)C)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 XNJIKCCLIKXVKC-UHFFFAOYSA-N 0.000 claims description 2
• ZOUYYHCVTKXASL-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)-3-chloroanilino]pyrido[2,3-d]pyrimidin-7-yl]-3-(2-hydroxyethyl)urea Chemical compound C1CN(C(=O)C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C(C=CC(NC(=O)NCCO)=N2)C2=N1 ZOUYYHCVTKXASL-UHFFFAOYSA-N 0.000 claims description 2
• HIDCSIGTHYPMDE-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)-3-chloroanilino]pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound C1CN(C(=O)C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 HIDCSIGTHYPMDE-UHFFFAOYSA-N 0.000 claims description 2
• VPZMIWQERRSJMV-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)-3-chloroanilino]pyrido[2,3-d]pyrimidin-7-yl]-3-ethylurea Chemical compound N=1C2=NC(NC(=O)NCC)=CC=C2C=NC=1NC(C=C1Cl)=CC=C1N1CCN(C(C)=O)CC1 VPZMIWQERRSJMV-UHFFFAOYSA-N 0.000 claims description 2
• NSELCHMQELGYCQ-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 NSELCHMQELGYCQ-UHFFFAOYSA-N 0.000 claims description 2
• UUJKLLDOWWAPFC-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-6-fluoropyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(F)C(NC(=O)NC2CCCCC2)=N2)C2=N1 UUJKLLDOWWAPFC-UHFFFAOYSA-N 0.000 claims description 2
• FZPOQOBRNOTAOD-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-yl]-3-(3-morpholin-4-ylpropyl)urea Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NCCCN2CCOCC2)=N2)C2=N1 FZPOQOBRNOTAOD-UHFFFAOYSA-N 0.000 claims description 2
• QSYGBWVAZZCIDX-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 QSYGBWVAZZCIDX-UHFFFAOYSA-N 0.000 claims description 2
• SFPLIUUSRNIYCV-CALCHBBNSA-N 1-[2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]-6-methylpyrido[2,3-d]pyrimidin-7-yl]-3-propan-2-ylurea Chemical compound N=1C=C2C=C(C)C(NC(=O)NC(C)C)=NC2=NC=1NC(C=C1)=CC=C1N1C[C@H](C)N[C@H](C)C1 SFPLIUUSRNIYCV-CALCHBBNSA-N 0.000 claims description 2
• GFUIAAHVXBLQBC-UHFFFAOYSA-N 1-[2-[4-[4-(2-amino-3-methylbutanoyl)piperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound C1CN(C(=O)C(N)C(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 GFUIAAHVXBLQBC-UHFFFAOYSA-N 0.000 claims description 2
• YWQNBCXNLXJJFZ-UHFFFAOYSA-N 1-[2-[4-[4-(2-amino-4-methylpentanoyl)piperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound C1CN(C(=O)C(N)CC(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 YWQNBCXNLXJJFZ-UHFFFAOYSA-N 0.000 claims description 2
• MQLDVUKGKUIAAL-UHFFFAOYSA-N 1-[5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-propan-2-ylurea Chemical compound N=1C2=NC(NC(=O)NC(C)C)=CC(C)=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 MQLDVUKGKUIAAL-UHFFFAOYSA-N 0.000 claims description 2
• UMAMFRHLUAOOPB-UHFFFAOYSA-N 1-[5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-propylurea Chemical compound N=1C2=NC(NC(=O)NCCC)=CC(C)=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 UMAMFRHLUAOOPB-UHFFFAOYSA-N 0.000 claims description 2
• MGJUUZSZYQUWRL-UHFFFAOYSA-N 1-[6-bromo-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound N1=C2N=C(NC(=O)NC3CCCCC3)C(Br)=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 MGJUUZSZYQUWRL-UHFFFAOYSA-N 0.000 claims description 2
• GUIPAUCBZRMQRW-UHFFFAOYSA-N 1-[6-bromo-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-methylurea Chemical compound N=1C=C2C=C(Br)C(NC(=O)NC)=NC2=NC=1NC(C=C1)=CC=C1N1CCNCC1 GUIPAUCBZRMQRW-UHFFFAOYSA-N 0.000 claims description 2
• VOOIEJLKMWHBIU-UHFFFAOYSA-N 1-[6-bromo-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound N=1C=C2C=C(Br)C(NC(=O)NC(C)(C)C)=NC2=NC=1NC(C=C1)=CC=C1N1CCNCC1 VOOIEJLKMWHBIU-UHFFFAOYSA-N 0.000 claims description 2
• CCJOQHQBAKQENC-CALCHBBNSA-N 1-[6-bromo-2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=C(Br)C(NC(=O)NC2CCCCC2)=N2)C2=N1 CCJOQHQBAKQENC-CALCHBBNSA-N 0.000 claims description 2
• PHULBAMDTWXUMM-GASCZTMLSA-N 1-[6-bromo-2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=C(Br)C(NC(=O)NC(C)(C)C)=N2)C2=N1 PHULBAMDTWXUMM-GASCZTMLSA-N 0.000 claims description 2
• ITGHYDKCLQIJEO-UHFFFAOYSA-N 1-[6-chloro-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound N1=C2N=C(NC(=O)NC3CCCCC3)C(Cl)=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 ITGHYDKCLQIJEO-UHFFFAOYSA-N 0.000 claims description 2
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