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

Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors Download PDF

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Publication number: CA2397961C
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

Application number

CA002397961A

Other languages

English (en)

French (fr)

Other versions

CA2397961A1 (en

Inventor

Richard John Booth

Ellen Myra Dobrusin

Vara Prasad Venkata Nagendra Josyula

Dennis Joseph Mcnamara

Peter Laurence Toogood

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

Priority date (The priority date 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 date listed.)

2000-01-25

Filing date

2001-01-23

Publication date

2008-08-26

2001-01-23 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

2001-08-02 Publication of CA2397961A1 publication Critical patent/CA2397961A1/en

2008-08-26 Application granted granted Critical

2008-08-26 Publication of CA2397961C publication Critical patent/CA2397961C/en

2021-01-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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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
DOBMFOXEPFCIAG-UHFFFAOYSA-N 1-[6-fluoro-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-propan-2-ylurea Chemical compound N=1C=C2C(C)=C(F)C(NC(=O)NC(C)C)=NC2=NC=1NC(C=C1)=CC=C1N1CCNCC1 DOBMFOXEPFCIAG-UHFFFAOYSA-N 0.000 claims description 2
AZMZKPOBCUYDGP-UHFFFAOYSA-N 1-cyclohexyl-1-methyl-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C=1C=C2C=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC2=NC=1NC(=O)N(C)C1CCCCC1 AZMZKPOBCUYDGP-UHFFFAOYSA-N 0.000 claims description 2
QJYWMRUQLGHKGW-UHFFFAOYSA-N 1-cyclohexyl-3-[2-(pyridin-4-ylamino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C=1C=C2C=NC(NC=3C=CN=CC=3)=NC2=NC=1NC(=O)NC1CCCCC1 QJYWMRUQLGHKGW-UHFFFAOYSA-N 0.000 claims description 2
BMTGASBFAFZLBO-UHFFFAOYSA-N 1-cyclohexyl-3-[2-[4-(3,3-dimethylpiperazin-1-yl)anilino]-6-fluoropyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1CNC(C)(C)CN1C(C=C1)=CC=C1NC1=NC=C(C=C(F)C(NC(=O)NC2CCCCC2)=N2)C2=N1 BMTGASBFAFZLBO-UHFFFAOYSA-N 0.000 claims description 2
APSFLJGQCXHNKS-UHFFFAOYSA-N 1-cyclohexyl-3-[2-[4-(3,3-dimethylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1CNC(C)(C)CN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 APSFLJGQCXHNKS-UHFFFAOYSA-N 0.000 claims description 2
VFDPUSVWSHRPRA-UHFFFAOYSA-N 1-cyclohexyl-3-[2-[4-(piperazine-1-carbonyl)anilino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C=1C=C2C=NC(NC=3C=CC(=CC=3)C(=O)N3CCNCC3)=NC2=NC=1NC(=O)NC1CCCCC1 VFDPUSVWSHRPRA-UHFFFAOYSA-N 0.000 claims description 2
FCZSXTNTJURAMC-CALCHBBNSA-N 1-cyclohexyl-3-[2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]-6-fluoropyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=C(F)C(NC(=O)NC2CCCCC2)=N2)C2=N1 FCZSXTNTJURAMC-CALCHBBNSA-N 0.000 claims description 2
HPBHWBGOZLFWIG-HDICACEKSA-N 1-cyclohexyl-3-[2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 HPBHWBGOZLFWIG-HDICACEKSA-N 0.000 claims description 2
CKDGTPVNAKRPFN-UHFFFAOYSA-N 1-cyclohexyl-3-[5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]thiourea Chemical compound N=1C2=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=CC=1NC(=S)NC1CCCCC1 CKDGTPVNAKRPFN-UHFFFAOYSA-N 0.000 claims description 2
URTRAPGHHQONHL-UHFFFAOYSA-N 1-cyclohexyl-3-[5-methyl-2-(pyridin-4-ylamino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC=3C=CN=CC=3)=NC=C2C(C)=CC=1NC(=O)NC1CCCCC1 URTRAPGHHQONHL-UHFFFAOYSA-N 0.000 claims description 2
BAZVIVARXKYKOK-UHFFFAOYSA-N 1-cyclohexyl-3-[6-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N1=C2N=C(NC(=O)NC3CCCCC3)C(C)=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 BAZVIVARXKYKOK-UHFFFAOYSA-N 0.000 claims description 2
CZKTXARZWICZDX-IYBDPMFKSA-N 1-cyclopropyl-3-[2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]-6-methylpyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=C(C)C(NC(=O)NC2CC2)=N2)C2=N1 CZKTXARZWICZDX-IYBDPMFKSA-N 0.000 claims description 2
GYPKJZNZYWJVDQ-UHFFFAOYSA-N 1-ethyl-3-[5-methyl-2-(pyridin-4-ylamino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NCC)=CC(C)=C2C=NC=1NC1=CC=NC=C1 GYPKJZNZYWJVDQ-UHFFFAOYSA-N 0.000 claims description 2
TUWWKUILUSIXFY-UHFFFAOYSA-N 1-methyl-3-[5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NC)=CC(C)=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 TUWWKUILUSIXFY-UHFFFAOYSA-N 0.000 claims description 2
SXXFFZGOAOAHCL-UHFFFAOYSA-N 1-tert-butyl-3-[2-(3-chloro-4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NC(C)(C)C)=CC=C2C=NC=1NC(C=C1Cl)=CC=C1N1CCNCC1 SXXFFZGOAOAHCL-UHFFFAOYSA-N 0.000 claims description 2
WWNCOUBNBSYUIV-UHFFFAOYSA-N 1-tert-butyl-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(C)(C)C)C=CC3=CN=2)=C1 WWNCOUBNBSYUIV-UHFFFAOYSA-N 0.000 claims description 2
ZERHTVLLTUQOES-UHFFFAOYSA-N 1-tert-butyl-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NC(C)(C)C)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 ZERHTVLLTUQOES-UHFFFAOYSA-N 0.000 claims description 2
VNRUZNQJRRPDRR-UHFFFAOYSA-N 1-tert-butyl-3-[2-(pyridin-4-ylamino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NC(C)(C)C)=CC=C2C=NC=1NC1=CC=NC=C1 VNRUZNQJRRPDRR-UHFFFAOYSA-N 0.000 claims description 2
FZYSIWYOHGFZSV-GASCZTMLSA-N 1-tert-butyl-3-[2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]-6-fluoropyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=C(F)C(NC(=O)NC(C)(C)C)=N2)C2=N1 FZYSIWYOHGFZSV-GASCZTMLSA-N 0.000 claims description 2
JMQKXBRWLIMTIU-IYBDPMFKSA-N 1-tert-butyl-3-[2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NC(C)(C)C)=N2)C2=N1 JMQKXBRWLIMTIU-IYBDPMFKSA-N 0.000 claims description 2
BDWLNZXAMQPJNX-CALCHBBNSA-N 1-tert-butyl-3-[2-[4-[(3s,5r)-3,5-dimethylpiperazin-1-yl]anilino]-6-ethylpyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N1=C2N=C(NC(=O)NC(C)(C)C)C(CC)=CC2=CN=C1NC(C=C1)=CC=C1N1C[C@H](C)N[C@H](C)C1 BDWLNZXAMQPJNX-CALCHBBNSA-N 0.000 claims description 2
IWQRQXJFCBIGMI-CALCHBBNSA-N 1-tert-butyl-3-[2-[4-[(3s,5r)-3,5-dimethylpiperazin-1-yl]anilino]-6-methylpyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=C(C)C(NC(=O)NC(C)(C)C)=N2)C2=N1 IWQRQXJFCBIGMI-CALCHBBNSA-N 0.000 claims description 2
POORIYMKOPMKPY-GASCZTMLSA-N 1-tert-butyl-3-[6-chloro-2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=C(Cl)C(NC(=O)NC(C)(C)C)=N2)C2=N1 POORIYMKOPMKPY-GASCZTMLSA-N 0.000 claims description 2
FTPGODXQOCTHDX-UHFFFAOYSA-N 1-tert-butyl-3-[6-fluoro-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C=C2C=C(F)C(NC(=O)NC(C)(C)C)=NC2=NC=1NC(C=C1)=CC=C1N1CCNCC1 FTPGODXQOCTHDX-UHFFFAOYSA-N 0.000 claims description 2
NUGDGYPKZDEUTI-UHFFFAOYSA-N 3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-1,1-dipropylurea Chemical compound N=1C2=NC(NC(=O)N(CCC)CCC)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 NUGDGYPKZDEUTI-UHFFFAOYSA-N 0.000 claims description 2
JCVWHDFOLJVVDR-KDURUIRLSA-N 3-cyclohexyl-1-[2-[4-[(3s,5r)-3,5-dimethylpiperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]-1-methylurea Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C=CC(=N2)N(C)C(=O)NC3CCCCC3)C2=N1 JCVWHDFOLJVVDR-KDURUIRLSA-N 0.000 claims description 2
PJYOLZRAIFCFFW-UHFFFAOYSA-N 3-cyclohexyl-1-ethyl-1-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C=1C=C2C=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC2=NC=1N(CC)C(=O)NC1CCCCC1 PJYOLZRAIFCFFW-UHFFFAOYSA-N 0.000 claims description 2
MGXJQAGOYXZWPI-HDICACEKSA-N 3-tert-butyl-1-[2-[4-[(3s,5r)-3,5-dimethylpiperazin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-yl]-1-ethylurea Chemical compound N=1C2=NC(N(C(=O)NC(C)(C)C)CC)=CC=C2C=NC=1NC(C=C1)=CC=C1N1C[C@H](C)N[C@H](C)C1 MGXJQAGOYXZWPI-HDICACEKSA-N 0.000 claims description 2
FTZPYSIBTYNADH-UHFFFAOYSA-N 4-methyl-n-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]piperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC=C(C=NC(NC=2C=CC(=CC=2)N2CCNCC2)=N2)C2=N1 FTZPYSIBTYNADH-UHFFFAOYSA-N 0.000 claims description 2
KLZXPCSKGWZKIP-UHFFFAOYSA-N 7-(dimethylsulfamoylamino)-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidine Chemical compound N=1C2=NC(NS(=O)(=O)N(C)C)=CC(C)=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 KLZXPCSKGWZKIP-UHFFFAOYSA-N 0.000 claims description 2
KSAZXYMGNAWJOF-UHFFFAOYSA-N C(C)(C)(C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)N2CCNCC2)N1)C Chemical compound C(C)(C)(C)NC(=O)NC=1C(=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)N2CCNCC2)N1)C KSAZXYMGNAWJOF-UHFFFAOYSA-N 0.000 claims description 2
101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims description 2
UWNFURNTZNSVDJ-UHFFFAOYSA-N ethyl 7-(tert-butylcarbamoylamino)-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidine-6-carboxylate Chemical compound N1=C2N=C(NC(=O)NC(C)(C)C)C(C(=O)OCC)=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 UWNFURNTZNSVDJ-UHFFFAOYSA-N 0.000 claims description 2
208000003849 large cell carcinoma Diseases 0.000 claims description 2
210000004072 lung Anatomy 0.000 claims description 2
FRTLPVFIQJYINI-UHFFFAOYSA-N n-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]acetamide Chemical compound N=1C2=NC(NC(=O)C)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 FRTLPVFIQJYINI-UHFFFAOYSA-N 0.000 claims description 2
SVNXEKWFYUHVHU-UHFFFAOYSA-N n-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]morpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NC(N=C1N=2)=CC=C1C=NC=2NC(C=C1)=CC=C1N1CCNCC1 SVNXEKWFYUHVHU-UHFFFAOYSA-N 0.000 claims description 2
210000000496 pancreas Anatomy 0.000 claims description 2
QYODGURZVDETMS-UHFFFAOYSA-N tert-butyl 4-[4-[[7-(cyclohexylcarbamoylamino)pyrido[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NC2CCCCC2)=N2)C2=N1 QYODGURZVDETMS-UHFFFAOYSA-N 0.000 claims description 2
JLJIEMWRJUNUFJ-UHFFFAOYSA-N tert-butyl 4-[4-[[7-(tert-butylcarbamoylamino)pyrido[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazine-1-carboxylate Chemical compound N=1C2=NC(NC(=O)NC(C)(C)C)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 JLJIEMWRJUNUFJ-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
125000006824 (C1-C6) dialkyl amine group Chemical group 0.000 claims 6
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 4
125000004415 heterocyclylalkyl group Chemical group 0.000 claims 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
102000018233 Fibroblast Growth Factor Human genes 0.000 claims 2
108050007372 Fibroblast Growth Factor Proteins 0.000 claims 2
102000010780 Platelet-Derived Growth Factor Human genes 0.000 claims 2
108010038512 Platelet-Derived Growth Factor Proteins 0.000 claims 2
229940126864 fibroblast growth factor Drugs 0.000 claims 2
SOMPXJVENKFJQG-UHFFFAOYSA-N 1-(2-aminoethyl)-3-[2-(4-fluoroanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NCCN)=CC=C2C=NC=1NC1=CC=C(F)C=C1 SOMPXJVENKFJQG-UHFFFAOYSA-N 0.000 claims 1
XMINZZZOTRYZGB-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NCCO)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 XMINZZZOTRYZGB-UHFFFAOYSA-N 0.000 claims 1
PAHKIBZRWFCOAM-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[2-(pyridin-4-ylamino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound N=1C2=NC(NC(=O)NCCO)=CC=C2C=NC=1NC1=CC=NC=C1 PAHKIBZRWFCOAM-UHFFFAOYSA-N 0.000 claims 1
YIGPZBASWQSHAE-IBGZPJMESA-N 1-[(2s)-1-hydroxy-4-methylpentan-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)CC(C)C)=CC=C2C=NC=1NC(C=C1)=CC=C1N1CCNCC1 YIGPZBASWQSHAE-IBGZPJMESA-N 0.000 claims 1
SNAZOIMRWKVMNQ-UHFFFAOYSA-N 1-[2-(3-chloro-4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-cyclohexylurea Chemical compound C=1C=C(N2CCNCC2)C(Cl)=CC=1NC(N=C1N=2)=NC=C1C=CC=2NC(=O)NC1CCCCC1 SNAZOIMRWKVMNQ-UHFFFAOYSA-N 0.000 claims 1
NYRIKOLUBUZKBZ-UHFFFAOYSA-N 1-[2-(3-chloro-4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-ethylurea Chemical compound N=1C2=NC(NC(=O)NCC)=CC=C2C=NC=1NC(C=C1Cl)=CC=C1N1CCNCC1 NYRIKOLUBUZKBZ-UHFFFAOYSA-N 0.000 claims 1
DWKOQXAXRXLTRO-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-yl]-3-(2-hydroxyethyl)urea Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(NC(=O)NCCO)=N2)C2=N1 DWKOQXAXRXLTRO-UHFFFAOYSA-N 0.000 claims 1
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ROWUHEGVMUYETM-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-6-fluoropyrido[2,3-d]pyrimidin-7-yl]-3-(2-hydroxyethyl)urea Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(F)C(NC(=O)NCCO)=N2)C2=N1 ROWUHEGVMUYETM-UHFFFAOYSA-N 0.000 claims 1
BRJVIFGBXXBAAR-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-6-fluoropyrido[2,3-d]pyrimidin-7-yl]-3-ethylurea Chemical compound N=1C=C2C=C(F)C(NC(=O)NCC)=NC2=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 BRJVIFGBXXBAAR-UHFFFAOYSA-N 0.000 claims 1
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FGEOIKBWVYUXSJ-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CC(NC(=O)NC(C)(C)C)=N2)C2=N1 FGEOIKBWVYUXSJ-UHFFFAOYSA-N 0.000 claims 1
IAAUSBXKBKRZHZ-UHFFFAOYSA-N 1-[6-fluoro-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-yl]-3-(2-hydroxyethyl)urea Chemical compound N=1C=C2C=C(F)C(NC(=O)NCCO)=NC2=NC=1NC(C=C1)=CC=C1N1CCNCC1 IAAUSBXKBKRZHZ-UHFFFAOYSA-N 0.000 claims 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 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
125000006000 trichloroethyl group Chemical group 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
231100000588 tumorigenic Toxicity 0.000 description 1
230000000381 tumorigenic effect Effects 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
208000010576 undifferentiated carcinoma Diseases 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
208000010570 urinary bladder carcinoma Diseases 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
229910000166 zirconium phosphate Inorganic materials 0.000 description 1

Classifications

- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Dermatology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Enzymes And Modification Thereof (AREA)

CA002397961A 2000-01-25 2001-01-23 Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors Expired - Fee Related CA2397961C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US17826100P	2000-01-25	2000-01-25
US60/178,261		2000-01-25
PCT/IB2001/000069 WO2001055147A1 (en)	2000-01-25	2001-01-23	PYRIDO[2,3-d]PYRIMIDINE-2,7-DIAMINE KINASE INHIBITORS

Publications (2)

Publication Number	Publication Date
CA2397961A1 CA2397961A1 (en)	2001-08-02
CA2397961C true CA2397961C (en)	2008-08-26

Family

ID=22651853

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002397961A Expired - Fee Related CA2397961C (en)	2000-01-25	2001-01-23	Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors

Country Status (34)

Country	Link
EP (1)	EP1254137A1 (is)
JP (1)	JP4047010B2 (is)
KR (1)	KR20020065939A (is)
CN (1)	CN1395578A (is)
AP (1)	AP2002002586A0 (is)
AR (1)	AR030044A1 (is)
AU (1)	AU2542501A (is)
BG (1)	BG106850A (is)
BR (1)	BR0107751A (is)
CA (1)	CA2397961C (is)
CO (1)	CO5261549A1 (is)
CR (1)	CR6706A (is)
CZ (1)	CZ20022475A3 (is)
DZ (1)	DZ3266A1 (is)
EA (1)	EA200200643A1 (is)
EE (1)	EE200200405A (is)
GT (1)	GT200100016A (is)
HN (1)	HN2001000013A (is)
HU (1)	HUP0204141A3 (is)
IL (1)	IL150545A0 (is)
IS (1)	IS6443A (is)
MA (1)	MA26868A1 (is)
MX (1)	MXPA02007221A (is)
NO (1)	NO20023527L (is)
OA (1)	OA12161A (is)
PA (1)	PA8510701A1 (is)
PE (1)	PE20011066A1 (is)
PL (1)	PL356802A1 (is)
SK (1)	SK10632002A3 (is)
SV (1)	SV2002000294A (is)
TN (1)	TNSN01014A1 (is)
WO (1)	WO2001055147A1 (is)
YU (1)	YU50402A (is)
ZA (1)	ZA200205879B (is)

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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
CN1847229B (zh)	2000-10-23	2011-05-04	史密丝克莱恩比彻姆公司	2，4，8-三取代-8H-吡啶并[2，3-d]嘧啶-7-酮化合物
PE20030008A1 (es) *	2001-06-19	2003-01-22	Bristol Myers Squibb Co	Inhibidores duales de pde 7 y pde 4
EP1499320B1 (en)	2002-04-19	2007-08-22	Smithkline Beecham Corporation	Novel compounds
US7504410B2 (en) *	2002-11-28	2009-03-17	Schering Aktiengesellschaft	Chk-, Pdk- and Akt-inhibitory pyrimidines, their production and use as pharmaceutical agents
US7157455B2 (en) *	2003-02-10	2007-01-02	Hoffmann-La Roche Inc.	4-Aminopyrimidine-5-one derivatives
TW200502236A (en) *	2003-03-28	2005-01-16	Hoffmann La Roche	Novel pyrido[2,3-d]pyrimidin-7-carboxylic acid derivatives, their manufacture and use as pharmaceutical agents
FR2873118B1 (fr)	2004-07-15	2007-11-23	Sanofi Synthelabo	Derives de pyrido-pyrimidine, leur application en therapeutique
EP1794160A1 (en) *	2004-09-21	2007-06-13	F.Hoffmann-La Roche Ag	6-(2-alkyl-phenyl) - pyrido[2,3-d] pyrimidines useful as proteine kinase inhibitors
EP1868612A4 (en)	2005-03-25	2010-03-24	Glaxo Group Ltd	NOVEL CONNECTIONS
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
UY29440A1 (es)	2005-03-25	2006-10-02	Glaxo Group Ltd	Nuevos compuestos
CN101495475A (zh)	2005-03-25	2009-07-29	葛兰素集团有限公司	制备吡啶并[2,3-d]嘧啶-7-酮和3,4-二氢嘧啶并[4,5-d]嘧啶-2(1H)-酮衍生物的方法
FR2887882B1 (fr)	2005-07-01	2007-09-07	Sanofi Aventis Sa	Derives de pyrido[2,3-d] pyrimidine, leur preparation, leur application en therapeutique
CN101243081A (zh) *	2005-07-21	2008-08-13	霍夫曼-拉罗奇有限公司	作为PTP1B抑制剂的吡啶并[2,3-d]嘧啶-2,4-二胺化合物
BRPI0614804A2 (pt) *	2005-08-09	2011-04-12	Irm Llc	compostos e composições como inibidores de proteìna cinase
FR2896246B1 (fr)	2006-01-13	2008-08-15	Sanofi Aventis Sa	Derives de pyrido-pyrimidone, leur preparation, leur application en therapeutique.
EP1914234A1 (en)	2006-10-16	2008-04-23	GPC Biotech Inc.	Pyrido[2,3-d]pyrimidines and their use as kinase inhibitors
JO2985B1 (ar)	2006-12-20	2016-09-05	Takeda Pharmaceuticals Co	مثبطات كينازmapk/erk
FR2910813B1 (fr) *	2006-12-28	2009-02-06	Sanofi Aventis Sa	Nouvelle utilisation therapeutique pour le traitement des leucemies
EP2112150B1 (en)	2008-04-22	2013-10-16	Forma Therapeutics, Inc.	Improved raf inhibitors
EP2352732B1 (en) *	2008-12-01	2013-02-20	Merck Patent GmbH	2,5-DIAMINO-SUBSTITUTED PYRIDO[4, 3-d]PYRIMIDINES AS AUTOTAXIN INHIBITORS AGAINST CANCER
GB201104267D0 (en)	2011-03-14	2011-04-27	Cancer Rec Tech Ltd	Pyrrolopyridineamino derivatives
GB201216018D0 (en)	2012-09-07	2012-10-24	Cancer Rec Tech Ltd	Pharmacologically active compounds
GB201216017D0 (en)	2012-09-07	2012-10-24	Cancer Rec Tech Ltd	Inhibitor compounds
ES2817448T3 (es)	2013-03-14	2021-04-07	Icahn School Med Mount Sinai	Compuestos de pirimidina como inhibidores de quinasas
GB201403536D0 (en)	2014-02-28	2014-04-16	Cancer Rec Tech Ltd	Inhibitor compounds
KR101671404B1 (ko) *	2014-09-02	2016-11-02	한국원자력의학원	항암 효과, 방사선 병용치료 효과 및 당뇨병 치료 효과를 갖는 피리미딘 유도체 및 이의 의학적 용도
CN107286180B (zh) *	2016-04-11	2019-07-02	上海勋和医药科技有限公司	杂代吡啶并嘧啶酮衍生物作为cdk抑制剂及其应用
GB201709840D0 (en)	2017-06-20	2017-08-02	Inst Of Cancer Research: Royal Cancer Hospital	Methods and medical uses

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SK281724B6 (sk) *	1994-11-14	2001-07-10	Warner-Lambert Company	6-arylpyrido[2,3-d]pyrimidíny, ich použitie a farmaceutické prostriedky na ich báze
IL115256A0 (en) *	1994-11-14	1995-12-31	Warner Lambert Co	6-Aryl pyrido (2,3-d) pyrimidines and naphthyridines and their use
US5620981A (en) *	1995-05-03	1997-04-15	Warner-Lambert Company	Pyrido [2,3-D]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation
KR20010043829A (ko) *	1998-05-26	2001-05-25	로즈 암스트롱, 크리스틴 에이. 트러트웨인	세포 증식 억제제로서의 비시클릭 피리미딘 및 비시클릭3,4-디히드로피리미딘

2001
- 2001-01-23 PE PE2001000072A patent/PE20011066A1/es not_active Application Discontinuation
- 2001-01-23 PA PA20018510701A patent/PA8510701A1/es unknown
- 2001-01-23 DZ DZ013266A patent/DZ3266A1/fr active
- 2001-01-23 AR ARP010100285A patent/AR030044A1/es not_active Application Discontinuation
- 2001-01-23 HU HU0204141A patent/HUP0204141A3/hu unknown
- 2001-01-23 EA EA200200643A patent/EA200200643A1/ru unknown
- 2001-01-23 YU YU50402A patent/YU50402A/sh unknown
- 2001-01-23 EP EP01900591A patent/EP1254137A1/en not_active Withdrawn
- 2001-01-23 JP JP2001561006A patent/JP4047010B2/ja not_active Expired - Fee Related
- 2001-01-23 AU AU25425/01A patent/AU2542501A/en not_active Abandoned
- 2001-01-23 WO PCT/IB2001/000069 patent/WO2001055147A1/en not_active Ceased
- 2001-01-23 EE EEP200200405A patent/EE200200405A/xx unknown
- 2001-01-23 CA CA002397961A patent/CA2397961C/en not_active Expired - Fee Related
- 2001-01-23 PL PL01356802A patent/PL356802A1/xx not_active Application Discontinuation
- 2001-01-23 CZ CZ20022475A patent/CZ20022475A3/cs unknown
- 2001-01-23 IL IL15054501A patent/IL150545A0/xx unknown
- 2001-01-23 AP APAP/P/2002/002586A patent/AP2002002586A0/en unknown
- 2001-01-23 GT GT200100016A patent/GT200100016A/es unknown
- 2001-01-23 MX MXPA02007221A patent/MXPA02007221A/es not_active Application Discontinuation
- 2001-01-23 SK SK1063-2002A patent/SK10632002A3/sk not_active Application Discontinuation
- 2001-01-23 KR KR1020027009516A patent/KR20020065939A/ko not_active Ceased
- 2001-01-23 BR BR0107751-1A patent/BR0107751A/pt not_active IP Right Cessation
- 2001-01-23 OA OA1200200213A patent/OA12161A/en unknown
- 2001-01-23 CN CN01804048A patent/CN1395578A/zh active Pending
- 2001-01-24 HN HN2001000013A patent/HN2001000013A/es unknown
- 2001-01-24 SV SV2001000294A patent/SV2002000294A/es not_active Application Discontinuation
- 2001-01-24 TN TNTNSN01014A patent/TNSN01014A1/fr unknown
- 2001-01-24 CO CO01005268A patent/CO5261549A1/es not_active Application Discontinuation
2002
- 2002-06-20 BG BG106850A patent/BG106850A/bg unknown
- 2002-06-25 IS IS6443A patent/IS6443A/is unknown
- 2002-07-17 CR CR6706A patent/CR6706A/es not_active Application Discontinuation
- 2002-07-22 MA MA26736A patent/MA26868A1/fr unknown
- 2002-07-23 ZA ZA200205879A patent/ZA200205879B/en unknown
- 2002-07-24 NO NO20023527A patent/NO20023527L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EA200200643A1 (ru)	2002-12-26
OA12161A (en)	2006-05-08
PE20011066A1 (es)	2001-10-22
AP2002002586A0 (en)	2002-09-30
ZA200205879B (en)	2003-09-29
WO2001055147A1 (en)	2001-08-02
SV2002000294A (es)	2002-07-16
EP1254137A1 (en)	2002-11-06
YU50402A (sh)	2005-11-28
IS6443A (is)	2002-06-25
BG106850A (bg)	2003-02-28
GT200100016A (es)	2001-10-19
IL150545A0 (en)	2003-02-12
PL356802A1 (en)	2004-07-12
CN1395578A (zh)	2003-02-05
NO20023527L (no)	2002-09-10
CA2397961A1 (en)	2001-08-02
CO5261549A1 (es)	2003-03-31
EE200200405A (et)	2003-12-15
MA26868A1 (fr)	2004-12-20
AU2542501A (en)	2001-08-07
DZ3266A1 (fr)	2001-08-02
AR030044A1 (es)	2003-08-13
JP2003523357A (ja)	2003-08-05
CR6706A (es)	2005-04-04
HN2001000013A (es)	2001-06-18
PA8510701A1 (es)	2002-12-11
NO20023527D0 (no)	2002-07-24
HUP0204141A2 (hu)	2003-04-28
JP4047010B2 (ja)	2008-02-13
HUP0204141A3 (en)	2005-03-29
SK10632002A3 (sk)	2003-06-03
KR20020065939A (ko)	2002-08-14
CZ20022475A3 (cs)	2003-03-12
BR0107751A (pt)	2002-11-12
TNSN01014A1 (fr)	2005-11-10
MXPA02007221A (es)	2002-11-29

Publication	Publication Date	Title
CA2397961C (en)	2008-08-26	Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors
US7053070B2 (en)	2006-05-30	Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors
CA2329703C (en)	2005-12-20	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
ES2274526T3 (es)	2007-05-16	Pirido(2,3-d)pirimidinas para inhibir la proliferacion celular mediada por tirosinaquinasa.
KR100421156B1 (ko)	2004-04-27	단백질티로신키나제매개세포증식을억제하기위한피리도[2,3-d]피리미딘
ES2301194T3 (es)	2008-06-16	Pirido 2,3-d pirimidinas y 4-aminopirimidinas como inhibidores de la proliferacion celular.
US20040242600A1 (en)	2004-12-02	4-amino-6-phenyl-pyrrolo[2,3-d]pyrimidine derivatives
US20090312321A1 (en)	2009-12-17	Compositions and methods for fgf receptor kinases inhibitors
US20040044012A1 (en)	2004-03-04	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
CZ2002846A3 (cs)	2003-02-12	Pteridinony, jako inhibitory kinasy
NZ520962A (en)	2003-09-26	5-alkylpyrido[2,3-d]pyrimidines cyclin-dependent tyrosine kinase inhibitors
JP2008519790A (ja)	2008-06-12	キナーゼ阻害剤としての１，４−置換ピラゾロピリミジン
JP6109880B2 (ja)	2017-04-05	三環式アザインドール
CN114380822B (zh)	2023-02-17	β-咔波啉母核的CDKs抑制剂及其制备方法和抗肿瘤的应用
NZ264133A (en)	1996-05-28	2-[pyrrolidino, piperidino and hexamethyleneimino] substituted pyrimido pyrimidine derivatives and pharmaceutical compositions
US7323469B2 (en)	2008-01-29	7H-pyrrolo[2,3-d]pyrimidine derivatives
OA11554A (en)	2004-06-03	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation.
MXPA00010738A (en)	2001-09-07	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
ZA200006536B (en)	2002-02-11	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation.

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Date	Code	Title	Description
2002-07-22	EEER	Examination request
2010-01-25	MKLA	Lapsed