SK17532000A3 - Prípadne substituované 3,4-dihydrogenované pyrimidíny, ich použitie a farmaceutické formulácie na ich báze - Google Patents

Prípadne substituované 3,4-dihydrogenované pyrimidíny, ich použitie a farmaceutické formulácie na ich báze Download PDF

Info

Publication number: SK17532000A3
Authority: SK; Slovakia
Prior art keywords: pyrimidin; phenylamino; pyrimido; dihydro; methyl
Prior art date: 1998-05-26

Application number

SK1753-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Ellen Myra Dobrusin

James Marino Hamby

James Bernard Kramer

Mel Conrad Schroeder

Howard Daniel Hollis Showalter

Peter Laurence Toogood

Susanne A. Trumpp-Kallmeyer

Original Assignee

Warner-Lambert Company

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.)

1998-05-26

Filing date

1999-05-10

Publication date

2002-08-06

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26775058&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK17532000(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1999-05-10 Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company

2002-08-06 Publication of SK17532000A3 publication Critical patent/SK17532000A3/sk

Links

-1 Bicyclic pyrimidines Chemical class 0.000 title claims description 197
230000004663 cell proliferation Effects 0.000 title claims description 9
239000003112 inhibitor Substances 0.000 title abstract description 15
150000001875 compounds Chemical class 0.000 claims abstract description 210
125000000217 alkyl group Chemical group 0.000 claims abstract description 52
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 41
229910052717 sulfur Inorganic materials 0.000 claims abstract description 41
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 25
206010028980 Neoplasm Diseases 0.000 claims abstract description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
230000002062 proliferating effect Effects 0.000 claims abstract description 17
102000003903 Cyclin-dependent kinases Human genes 0.000 claims abstract description 16
108090000266 Cyclin-dependent kinases Proteins 0.000 claims abstract description 16
201000011510 cancer Diseases 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 14
230000033115 angiogenesis Effects 0.000 claims abstract description 12
230000001404 mediated effect Effects 0.000 claims abstract description 11
208000037803 restenosis Diseases 0.000 claims abstract description 11
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 9
239000003102 growth factor Substances 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 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
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 85
229910052757 nitrogen Inorganic materials 0.000 claims description 39
229910052760 oxygen Inorganic materials 0.000 claims description 39
125000001072 heteroaryl group Chemical group 0.000 claims description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 29
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 23
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 22
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 22
201000010099 disease Diseases 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
101150073031 cdk2 gene Proteins 0.000 claims description 18
150000002466 imines Chemical class 0.000 claims description 18
108050007372 Fibroblast Growth Factor Proteins 0.000 claims description 17
102000018233 Fibroblast Growth Factor Human genes 0.000 claims description 17
229940126864 fibroblast growth factor Drugs 0.000 claims description 17
125000000623 heterocyclic group Chemical group 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 16
230000002401 inhibitory effect Effects 0.000 claims description 16
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 16
125000004001 thioalkyl group Chemical group 0.000 claims description 16
150000003573 thiols Chemical class 0.000 claims description 15
101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 14
108010038512 Platelet-Derived Growth Factor Proteins 0.000 claims description 13
102000010780 Platelet-Derived Growth Factor Human genes 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical class [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 13
239000001301 oxygen Chemical class 0.000 claims description 13
125000000547 substituted alkyl group Chemical group 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 10
101150012716 CDK1 gene Proteins 0.000 claims description 10
101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 claims description 10
108091000080 Phosphotransferase Proteins 0.000 claims description 10
102000020233 phosphotransferase Human genes 0.000 claims description 10
LPUCHTNHUHOTRY-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)ethanamine Chemical compound C1CC2C(C(N)C)CC1C2 LPUCHTNHUHOTRY-UHFFFAOYSA-N 0.000 claims description 9
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
239000004202 carbamide Substances 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
150000002829 nitrogen Chemical class 0.000 claims description 8
108090000623 proteins and genes Proteins 0.000 claims description 8
239000011593 sulfur Chemical class 0.000 claims description 8
201000004681 Psoriasis Diseases 0.000 claims description 7
101100273808 Xenopus laevis cdk1-b gene Proteins 0.000 claims description 7
125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical class ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 7
150000002825 nitriles Chemical class 0.000 claims description 7
150000002923 oximes Chemical class 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 7
206010012689 Diabetic retinopathy Diseases 0.000 claims description 6
210000002464 muscle smooth vascular Anatomy 0.000 claims description 6
230000035755 proliferation Effects 0.000 claims description 6
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 claims description 5
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims description 5
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims description 5
229910052786 argon Inorganic materials 0.000 claims description 5
102000037979 non-receptor tyrosine kinases Human genes 0.000 claims description 5
108091008046 non-receptor tyrosine kinases Proteins 0.000 claims description 5
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
150000003857 carboxamides Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000001998 leucyl group Chemical group 0.000 claims description 4
WFBDWTZOYPUBQZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]formamide Chemical compound CN(C)CCCNC=O WFBDWTZOYPUBQZ-UHFFFAOYSA-N 0.000 claims description 4
OOJYJQIMJKZUSJ-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-7-[4-(4-methylpiperazin-1-yl)anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NC(=O)N2C3C4CCC(C4)C3)C2=N1 OOJYJQIMJKZUSJ-UHFFFAOYSA-N 0.000 claims description 3
NIZHMCZGWWIWKG-UHFFFAOYSA-N 7-[4-[2-(diethylamino)ethoxy]anilino]-3-(3,5-dimethoxyphenyl)-1-ethyl-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(CN(C(=O)N2CC)C=3C=C(OC)C=C(OC)C=3)C2=N1 NIZHMCZGWWIWKG-UHFFFAOYSA-N 0.000 claims description 3
CKEBVRPXMIKWIP-UHFFFAOYSA-N 8-methyl-2-(4-pyrazol-1-ylanilino)-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound N1=C2N(C)C(=O)NCC2=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 CKEBVRPXMIKWIP-UHFFFAOYSA-N 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
REAXZCOCRIIZGW-UHFFFAOYSA-N 1-(3,5-dimethylheptyl)-7-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(CCC(C)CC(C)CC)C2=CC=1NC(C=C1)=CC=C1N1CCN(C)CC1 REAXZCOCRIIZGW-UHFFFAOYSA-N 0.000 claims description 2
VRKQHBMOSLPUBQ-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-7-[4-(4-hydroxypiperidin-1-yl)anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NC(=O)N2C3C4CCC(C4)C3)C2=N1 VRKQHBMOSLPUBQ-UHFFFAOYSA-N 0.000 claims description 2
CXCVAMWLZIFURV-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-7-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(C3C4CCC(C4)C3)C(=O)N=CC2=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1CCCN1CCOCC1 CXCVAMWLZIFURV-UHFFFAOYSA-N 0.000 claims description 2
ZZADPTLVHZAONE-UHFFFAOYSA-N 1-(3-hydroxypropyl)-7-[4-(4-methylpiperazin-1-yl)anilino]-3,4-dihydropyrido[4,3-d]pyrimidin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(N=C1)=CC2=C1CNC(=O)N2CCCO ZZADPTLVHZAONE-UHFFFAOYSA-N 0.000 claims description 2
WALFZDZPONVUIH-UHFFFAOYSA-N 1-(3-hydroxypropyl)-7-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC(N=C1)=CC2=C1C=NC(=O)N2CCCO WALFZDZPONVUIH-UHFFFAOYSA-N 0.000 claims description 2
JMNNHVDOWHBZGS-UHFFFAOYSA-N 1-[3-(2-chloro-3,5-dimethoxyphenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-4h-pyrimido[4,5-d]pyrimidin-2-yl]-3-ethylurea Chemical compound N=1C=C2CN(C=3C(=C(OC)C=C(OC)C=3)Cl)C(NC(=O)NCC)=NC2=NC=1NC1=CC=C(OCCN(CC)CC)C=C1 JMNNHVDOWHBZGS-UHFFFAOYSA-N 0.000 claims description 2
QUAQRTRBWXHSIP-UHFFFAOYSA-N 1-[7-(4-fluoroanilino)pyrimido[4,5-d]pyrimidin-2-yl]-3-methylurea Chemical compound N=1C2=NC(NC(=O)NC)=NC=C2C=NC=1NC1=CC=C(F)C=C1 QUAQRTRBWXHSIP-UHFFFAOYSA-N 0.000 claims description 2
DYJKMKVDTNJHMT-UHFFFAOYSA-N 1-cyclopentyl-3-(2,6-dichloro-3,5-dimethoxyphenyl)-7-(pyridin-4-ylamino)-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound COC1=CC(OC)=C(Cl)C(N2C(N(C3CCCC3)C3=NC(NC=4C=CN=CC=4)=NC=C3C2)=O)=C1Cl DYJKMKVDTNJHMT-UHFFFAOYSA-N 0.000 claims description 2
HSHLNEJOCHYTQO-UHFFFAOYSA-N 1-cyclopentyl-7-(4-piperazin-1-ylanilino)pyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(C3CCCC3)C(=O)N=CC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 HSHLNEJOCHYTQO-UHFFFAOYSA-N 0.000 claims description 2
MXEAYMDSLOTGOA-UHFFFAOYSA-N 1-hexa-2,4-dienyl-7-[4-(4-methylpiperazin-1-yl)anilino]pyrido[4,3-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(CC=CC=CC)C2=CC=1NC(C=C1)=CC=C1N1CCN(C)CC1 MXEAYMDSLOTGOA-UHFFFAOYSA-N 0.000 claims description 2
WGFUGBMZQCPOMB-UHFFFAOYSA-N 1-methyl-7-(4-pyrazol-1-ylanilino)pyrimido[4,5-d]pyrimidin-2-one Chemical compound N=1C=C2C=NC(=O)N(C)C2=NC=1NC(C=C1)=CC=C1N1C=CC=N1 WGFUGBMZQCPOMB-UHFFFAOYSA-N 0.000 claims description 2
KAHIEOWPOWHUDI-UHFFFAOYSA-N 1-methyl-7-[4-(4-methylpiperazin-1-yl)anilino]pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=NC(=O)N2C)C2=N1 KAHIEOWPOWHUDI-UHFFFAOYSA-N 0.000 claims description 2
CCECTNAHAIMUMV-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-6-(3,5-dimethoxyphenyl)-5,8-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C(CN(C(=O)N2)C=3C=C(OC)C=C(OC)C=3)C2=N1 CCECTNAHAIMUMV-UHFFFAOYSA-N 0.000 claims description 2
DKTBRRPWLIMTOU-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-8-propan-2-ylpyrimido[4,5-d]pyrimidine-5,7-dione Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC=C2C(=O)NC(=O)N(C(C)C)C2=N1 DKTBRRPWLIMTOU-UHFFFAOYSA-N 0.000 claims description 2
PMNMAKDXTTUSPU-UHFFFAOYSA-N 2-[4-[4-(2-amino-4-methylpentanoyl)piperazin-1-yl]anilino]-8-cyclopentyl-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound C1CN(C(=O)C(N)CC(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(CNC(=O)N2C3CCCC3)C2=N1 PMNMAKDXTTUSPU-UHFFFAOYSA-N 0.000 claims description 2
ATDKYWXVGAOUSY-UHFFFAOYSA-N 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(CC)C(=O)N(C=3C(=C(OC)C=C(OC)C=3Cl)Cl)CC2=CN=C1NC1=CC=NC=C1 ATDKYWXVGAOUSY-UHFFFAOYSA-N 0.000 claims description 2
MLDWCFFWBYYCHV-UHFFFAOYSA-N 3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(CC)C(=O)N(C=3C(=C(OC)C=C(OC)C=3Cl)Cl)CC2=CN=C1NC1=CC=NC=C1 MLDWCFFWBYYCHV-UHFFFAOYSA-N 0.000 claims description 2
RKNCRQYWAJEDJW-UHFFFAOYSA-N 3-(2,6-dichloro-3,5-dimethoxyphenyl)-7-[4-(diethylamino)butylamino]-1-ethyl-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound O=C1N(CC)C2=NC(NCCCCN(CC)CC)=NC=C2CN1C1=C(Cl)C(OC)=CC(OC)=C1Cl RKNCRQYWAJEDJW-UHFFFAOYSA-N 0.000 claims description 2
NNXCBTRERGAZEA-UHFFFAOYSA-N 3-(2,6-dichloro-3-hydroxyphenyl)-7-[3-(hydroxymethyl)anilino]-1-methyl-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(C)C(=O)N(C=3C(=C(O)C=CC=3Cl)Cl)CC2=CN=C1NC1=CC=CC(CO)=C1 NNXCBTRERGAZEA-UHFFFAOYSA-N 0.000 claims description 2
ZMJAWSDJCUMJJN-UHFFFAOYSA-N 3-(2,6-dichloro-3-hydroxyphenyl)-7-[4-[2-(ethylamino)ethoxy]anilino]-1-methyl-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC=C(CN(C(=O)N2C)C=3C(=C(O)C=CC=3Cl)Cl)C2=N1 ZMJAWSDJCUMJJN-UHFFFAOYSA-N 0.000 claims description 2
HXMLDEDAODDCMA-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-7-[3-(hydroxymethyl)anilino]-1-methyl-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(C)C(=O)N(C=3C(=CC=CC=3Cl)Cl)CC2=CN=C1NC1=CC=CC(CO)=C1 HXMLDEDAODDCMA-UHFFFAOYSA-N 0.000 claims description 2
YZTNFDSBXMLNPR-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-7-[4-[2-(ethylamino)ethoxy]anilino]-1-methyl-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC=C(CN(C(=O)N2C)C=3C(=CC=CC=3Cl)Cl)C2=N1 YZTNFDSBXMLNPR-UHFFFAOYSA-N 0.000 claims description 2
QCXFHIZGBBCJGW-UHFFFAOYSA-N 3-(2-chloro-3,5-dimethoxyphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(CC)C(=O)N(C=3C(=C(OC)C=C(OC)C=3)Cl)CC2=CN=C1NC1=CC=NC=C1 QCXFHIZGBBCJGW-UHFFFAOYSA-N 0.000 claims description 2
HPSGUKXETOSKQL-UHFFFAOYSA-N 3-(2-chloro-3,5-dimethoxyphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(CC)C(=O)N(C=3C(=C(OC)C=C(OC)C=3)Cl)CC2=CN=C1NC1=CC=NC=C1 HPSGUKXETOSKQL-UHFFFAOYSA-N 0.000 claims description 2
ILEBETNCQGVQSD-UHFFFAOYSA-N 3-(3,5-dimethoxy-2,6-dimethylphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(CC)C(=O)N(C=3C(=C(OC)C=C(OC)C=3C)C)CC2=CN=C1NC1=CC=NC=C1 ILEBETNCQGVQSD-UHFFFAOYSA-N 0.000 claims description 2
HMCMLNXKVZNMIG-UHFFFAOYSA-N 3-(3,5-dimethoxy-2,6-dimethylphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(CC)C(=O)N(C=3C(=C(OC)C=C(OC)C=3C)C)CC2=CN=C1NC1=CC=NC=C1 HMCMLNXKVZNMIG-UHFFFAOYSA-N 0.000 claims description 2
HITQWFZPALJPSM-UHFFFAOYSA-N 3-(3,5-dimethoxy-2-methylphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(CC)C(=O)N(C=3C(=C(OC)C=C(OC)C=3)C)CC2=CN=C1NC1=CC=NC=C1 HITQWFZPALJPSM-UHFFFAOYSA-N 0.000 claims description 2
OHVWWJZFAXWHHP-UHFFFAOYSA-N 3-(3,5-dimethoxy-2-methylphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrimido[4,5-d]pyrimidin-2-one Chemical compound N1=C2N(CC)C(=O)N(C=3C(=C(OC)C=C(OC)C=3)C)CC2=CN=C1NC1=CC=NC=C1 OHVWWJZFAXWHHP-UHFFFAOYSA-N 0.000 claims description 2
DDHHWHJBJCYDFY-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-1-ethyl-7-(pyridin-4-ylamino)-4h-pyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C2N(CC)C(=O)N(C=3C=C(OC)C=C(OC)C=3)CC2=CN=C1NC1=CC=NC=C1 DDHHWHJBJCYDFY-UHFFFAOYSA-N 0.000 claims description 2
SASAJJQXTORYMM-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-1-ethyl-7-(pyridin-4-ylamino)pyrimido[4,5-d]pyrimidine-2,4-dione Chemical compound N=1C=C2C(=O)N(C=3C=C(OC)C=C(OC)C=3)C(=O)N(CC)C2=NC=1NC1=CC=NC=C1 SASAJJQXTORYMM-UHFFFAOYSA-N 0.000 claims description 2
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BKHNPXOUNMTMCY-UHFFFAOYSA-N 3-[[3-(2,6-dichlorophenyl)-1-methyl-2-oxo-4h-pyrimido[4,5-d]pyrimidin-7-yl]amino]benzoic acid Chemical compound N1=C2N(C)C(=O)N(C=3C(=CC=CC=3Cl)Cl)CC2=CN=C1NC1=CC=CC(C(O)=O)=C1 BKHNPXOUNMTMCY-UHFFFAOYSA-N 0.000 claims description 2
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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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Ophthalmology & Optometry (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

SK1753-2000A 1998-05-26 1999-05-10 Prípadne substituované 3,4-dihydrogenované pyrimidíny, ich použitie a farmaceutické formulácie na ich báze SK17532000A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US8670898P	1998-05-26	1998-05-26
US12615899P	1999-03-25	1999-03-25
PCT/US1999/010187 WO1999061444A2 (en)	1998-05-26	1999-05-10	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation

Publications (1)

Publication Number	Publication Date
SK17532000A3 true SK17532000A3 (sk)	2002-08-06

Family

ID=26775058

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1753-2000A SK17532000A3 (sk)	1998-05-26	1999-05-10	Prípadne substituované 3,4-dihydrogenované pyrimidíny, ich použitie a farmaceutické formulácie na ich báze

Country Status (28)

Country	Link
US (1)	US7501425B1 (et)
EP (1)	EP1080092B1 (et)
JP (1)	JP2002516327A (et)
KR (1)	KR20010043829A (et)
CN (1)	CN1138778C (et)
AP (1)	AP2000001964A0 (et)
AT (1)	ATE402177T1 (et)
AU (1)	AU763839B2 (et)
BG (1)	BG104960A (et)
BR (1)	BR9911590A (et)
CA (1)	CA2329703C (et)
DE (1)	DE69939168D1 (et)
EA (1)	EA003640B1 (et)
EE (1)	EE200000706A (et)
ES (1)	ES2310039T3 (et)
GE (1)	GEP20033093B (et)
HR (1)	HRP20000799A2 (et)
HU (1)	HUP0102514A3 (et)
ID (1)	ID27589A (et)
IL (1)	IL139599A0 (et)
IS (1)	IS5687A (et)
NO (1)	NO20005928L (et)
NZ (1)	NZ508268A (et)
PL (1)	PL344248A1 (et)
SK (1)	SK17532000A3 (et)
TR (1)	TR200003429T2 (et)
WO (1)	WO1999061444A2 (et)
YU (1)	YU73300A (et)

Families Citing this family (110)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20010043829A (ko)	1998-05-26	2001-05-25	로즈 암스트롱, 크리스틴 에이. 트러트웨인	세포 증식 억제제로서의 비시클릭 피리미딘 및 비시클릭3,4-디히드로피리미딘
EP1123295B1 (en) *	1998-10-23	2004-09-29	F. Hoffmann-La Roche Ag	Bicyclic nitrogen heterocycles
AU776250B2 (en)	1999-10-21	2004-09-02	F. Hoffmann-La Roche Ag	Heteroalkylamino-substituted bicyclic nitrogen heterocycles as inhibitors of P38 protein kinase
HUP0203477A3 (en) *	1999-10-21	2004-12-28	Hoffmann La Roche	Alkylamino substituted bicyclic nitrogen heterocycles as inhibitors of p38 protein kinase, pharmaceutical compositions containing them and their preparations
EA005585B1 (ru)	2000-01-24	2005-04-28	Уорнер-Ламберт Компани	3-аминохиназолин-2,4-дионовые антибактериальные агенты
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1999
- 1999-05-10 KR KR1020007013279A patent/KR20010043829A/ko not_active Ceased
- 1999-05-10 CA CA002329703A patent/CA2329703C/en not_active Expired - Fee Related
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- 1999-05-10 EA EA200001171A patent/EA003640B1/ru not_active IP Right Cessation
- 1999-05-10 BR BR9911590-5A patent/BR9911590A/pt not_active Application Discontinuation
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- 1999-05-10 AP APAP/P/2000/001964A patent/AP2000001964A0/en unknown
2000
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Publication number	Publication date
CA2329703A1 (en)	1999-12-02
DE69939168D1 (de)	2008-09-04
KR20010043829A (ko)	2001-05-25
AP2000001964A0 (en)	2000-12-31
JP2002516327A (ja)	2002-06-04
BR9911590A (pt)	2001-02-13
TR200003429T2 (tr)	2001-07-23
EP1080092A2 (en)	2001-03-07
EE200000706A (et)	2002-06-17
CA2329703C (en)	2005-12-20
GEP20033093B (en)	2003-10-27
HUP0102514A3 (en)	2002-03-28
NZ508268A (en)	2004-02-27
CN1138778C (zh)	2004-02-18
WO1999061444A3 (en)	2000-02-03
HRP20000799A2 (en)	2001-06-30
HUP0102514A2 (hu)	2001-11-28
ES2310039T3 (es)	2008-12-16
ID27589A (id)	2001-04-12
EA003640B1 (ru)	2003-08-28
BG104960A (en)	2001-10-31
IS5687A (is)	2000-10-27
EA200001171A1 (ru)	2001-06-25
AU4073499A (en)	1999-12-13
PL344248A1 (en)	2001-10-22
HK1039483A1 (en)	2002-04-26
CN1302301A (zh)	2001-07-04
NO20005928D0 (no)	2000-11-23
YU73300A (sh)	2003-08-29
IL139599A0 (en)	2002-02-10
US7501425B1 (en)	2009-03-10
EP1080092B1 (en)	2008-07-23
AU763839B2 (en)	2003-07-31
ATE402177T1 (de)	2008-08-15
WO1999061444A2 (en)	1999-12-02
NO20005928L (no)	2000-11-23

Publication	Publication Date	Title
CA2329703C (en)	2005-12-20	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
US20040044012A1 (en)	2004-03-04	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
EP0964864B1 (en)	2008-04-09	Pyrido 2,3-d pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation
US5945422A (en)	1999-08-31	N-oxides of amino containing pyrido 2,3-D! pyrimidines
US5733913A (en)	1998-03-31	6-Aryl pyrido 2,3-d! pyrimidines and naphthyridines for inhibiting protein tyrosine kinase mediated cellular proliferation
AU777468B2 (en)	2004-10-21	Pteridinones as kinase inhibitors
EP0790997B1 (en)	2000-03-22	6-ARYL PYRIDO[2,3-d]PYRIMIDINES AND NAPHTHYRIDINES FOR INHIBITING PROTEIN TYROSINE KINASE MEDIATED CELLULAR PROLIFERATION
KR19990008252A (ko)	1999-01-25	단백질 티로신 키나제 매개된 세포 증식을 억제하기 위한 피리도[2,3-ｄ]피리미딘
MXPA02007221A (es)	2002-11-29	Inhibidores de pirido [2,3-d)pirimidin-2,7-diamina cinasa.
JP3541829B2 (ja)	2004-07-14	ピリドトリアジンおよびピリドピリダジン
EP1801112A1 (en)	2007-06-27	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
CZ20004246A3 (cs)	2001-04-11	Bicyklické pyrimidiny a bicyklické 3,4- dihydropyrimidiny jako inhibitory buněčné proliferace
MXPA00010738A (en)	2001-09-07	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
OA11554A (en)	2004-06-03	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation.
KR100559261B1 (ko)	2006-03-15	2Ｈ-피리도[4,5-ｅ][1,2,4]트리아진-3-일리덴-시안아마이드의 유도체 및 그의 제조방법
ZA200006536B (en)	2002-02-11	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation.
EP1806348A2 (en)	2007-07-11	Pyrido (2,3-D)Pyrimidines as inhibitors of cellular proliferation
CA2199964A1 (en)	1996-05-23	6-aryl pyrido[2,3-d]pyrimidines and naphthyridines for inhibiting protein tyrosine kinase mediated cellular proliferation