JP5797664B2 - 置換ピリド[2,3−d]ピリミジン−7(8H)−オン及びそれらの治療用の使用 - Google Patents
置換ピリド[2,3−d]ピリミジン−7(8H)−オン及びそれらの治療用の使用 Download PDFInfo
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- JP5797664B2 JP5797664B2 JP2012544865A JP2012544865A JP5797664B2 JP 5797664 B2 JP5797664 B2 JP 5797664B2 JP 2012544865 A JP2012544865 A JP 2012544865A JP 2012544865 A JP2012544865 A JP 2012544865A JP 5797664 B2 JP5797664 B2 JP 5797664B2
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- Prior art keywords
- pyrimidin
- alkyl
- compound
- ylamino
- methyl
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- 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.)
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- 230000001225 therapeutic effect Effects 0.000 title description 4
- WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical class N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 445
- -1 substituted Chemical class 0.000 claims description 211
- 150000003839 salts Chemical class 0.000 claims description 165
- 125000000217 alkyl group Chemical group 0.000 claims description 155
- 238000000034 method Methods 0.000 claims description 149
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 95
- 210000004027 cell Anatomy 0.000 claims description 94
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 84
- 206010028980 Neoplasm Diseases 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 74
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 69
- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 49
- 201000011510 cancer Diseases 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000002947 alkylene group Chemical group 0.000 claims description 39
- 230000002062 proliferating effect Effects 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 28
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
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- 208000035475 disorder Diseases 0.000 claims description 23
- ZEHBZHZMQSHZFI-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F ZEHBZHZMQSHZFI-UHFFFAOYSA-N 0.000 claims description 20
- ZCBIFHNDZBSCEP-UHFFFAOYSA-N 1H-indol-5-amine Chemical compound NC1=CC=C2NC=CC2=C1 ZCBIFHNDZBSCEP-UHFFFAOYSA-N 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 239000007800 oxidant agent Substances 0.000 claims description 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000005647 linker group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229940127121 immunoconjugate Drugs 0.000 claims description 12
- 230000001590 oxidative effect Effects 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 230000006907 apoptotic process Effects 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 9
- 208000032839 leukemia Diseases 0.000 claims description 9
- 150000003462 sulfoxides Chemical class 0.000 claims description 9
- 210000004698 lymphocyte Anatomy 0.000 claims description 8
- 208000030289 Lymphoproliferative disease Diseases 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 206010033128 Ovarian cancer Diseases 0.000 claims description 6
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
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- 230000001684 chronic effect Effects 0.000 claims description 6
- 230000001939 inductive effect Effects 0.000 claims description 6
- 201000010260 leiomyoma Diseases 0.000 claims description 6
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 5
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 5
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 5
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
- 201000010881 cervical cancer Diseases 0.000 claims description 5
- 201000005202 lung cancer Diseases 0.000 claims description 5
- 208000020816 lung neoplasm Diseases 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- LXHBYNYYXSUIGS-UHFFFAOYSA-N 2-(1h-indol-4-ylamino)-8-methyl-6-(4-methylphenyl)sulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=CC2=C1C=CN2 LXHBYNYYXSUIGS-UHFFFAOYSA-N 0.000 claims description 4
- VAKARYFWENOUDM-UHFFFAOYSA-N 2-(1h-indol-5-ylamino)-6-(4-methoxyphenyl)sulfonyl-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=C(NC=C2)C2=C1 VAKARYFWENOUDM-UHFFFAOYSA-N 0.000 claims description 4
- OBJHBFRLGFYXOG-UHFFFAOYSA-N 2-(1h-indol-5-ylamino)-8-methyl-6-(4-methylphenyl)sulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=C(NC=C2)C2=C1 OBJHBFRLGFYXOG-UHFFFAOYSA-N 0.000 claims description 4
- ZKOJYIDLWPSYGM-UHFFFAOYSA-N 2-(4-chloroanilino)-6-(4-chlorophenyl)sulfonyl-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(S(=O)(=O)C=3C=CC(Cl)=CC=3)C(=O)N(C)C2=NC=1NC1=CC=C(Cl)C=C1 ZKOJYIDLWPSYGM-UHFFFAOYSA-N 0.000 claims description 4
- ROPYKEHRRDHEDL-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-8-methyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(S(C)=O)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F ROPYKEHRRDHEDL-UHFFFAOYSA-N 0.000 claims description 4
- ITJHZDKREUXYAW-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 ITJHZDKREUXYAW-UHFFFAOYSA-N 0.000 claims description 4
- VCUUTCCRXTWNIO-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)sulfonyl-8-methyl-2-(1h-pyrrolo[2,3-b]pyridin-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=NC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 VCUUTCCRXTWNIO-UHFFFAOYSA-N 0.000 claims description 4
- VMFHEFCVRVXZNB-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(Cl)C=C1 VMFHEFCVRVXZNB-UHFFFAOYSA-N 0.000 claims description 4
- RKTRISFGTUOQPN-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-2-(4-methoxyanilino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=C(C(=O)N2C)S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=N1 RKTRISFGTUOQPN-UHFFFAOYSA-N 0.000 claims description 4
- AYQDSCILAZMDJN-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-methyl-2-(3-morpholin-4-ylpropylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(S(=O)(=O)C=3C=CC(Cl)=CC=3)C(=O)N(C)C2=NC=1NCCCN1CCOCC1 AYQDSCILAZMDJN-UHFFFAOYSA-N 0.000 claims description 4
- YRJPDCGJCBKORL-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-methyl-2-(quinolin-3-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CC=CC4=NC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(Cl)C=C1 YRJPDCGJCBKORL-UHFFFAOYSA-N 0.000 claims description 4
- WPVNZNZUEGUXOM-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-methyl-2-[2-(4-methylpiperazin-1-yl)ethylamino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1CCNC1=NC=C(C=C(C(=O)N2C)S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=N1 WPVNZNZUEGUXOM-UHFFFAOYSA-N 0.000 claims description 4
- TURFAYJSDRRABW-UHFFFAOYSA-N 6-(4-fluorophenyl)sulfonyl-2-(1h-indazol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=NNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1 TURFAYJSDRRABW-UHFFFAOYSA-N 0.000 claims description 4
- QVJAKNZSGPLMPU-UHFFFAOYSA-N 6-(4-fluorophenyl)sulfonyl-2-(1h-indol-6-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4NC=CC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1 QVJAKNZSGPLMPU-UHFFFAOYSA-N 0.000 claims description 4
- FCPZOGCMAQOPBZ-UHFFFAOYSA-N 6-(4-hydroxyphenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(O)C=C1 FCPZOGCMAQOPBZ-UHFFFAOYSA-N 0.000 claims description 4
- IWTQBSNGCUQPTE-UHFFFAOYSA-N 6-(benzenesulfonyl)-2-(1h-indol-6-ylamino)-8-propylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCC)C2=NC(NC=3C=C4NC=CC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 IWTQBSNGCUQPTE-UHFFFAOYSA-N 0.000 claims description 4
- MLMHICKPMVFARV-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(C(=O)N2C3CCCC3)S(=O)(=O)C=3C=CC=CC=3)C2=N1 MLMHICKPMVFARV-UHFFFAOYSA-N 0.000 claims description 4
- DSJNKAYLBBXYCM-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-ethyl-2-(1h-indol-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 DSJNKAYLBBXYCM-UHFFFAOYSA-N 0.000 claims description 4
- QENLQBPFPCBNBA-UHFFFAOYSA-N 8-methyl-6-(4-methylphenyl)sulfonyl-2-(1h-pyrrolo[2,3-b]pyridin-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CN=C(NC=C2)C2=C1 QENLQBPFPCBNBA-UHFFFAOYSA-N 0.000 claims description 4
- XYSZRTHDXHPSRH-UHFFFAOYSA-N 8-methyl-6-(4-methylphenyl)sulfonyl-2-[(2-oxo-1,3-dihydroindol-5-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=C(NC(=O)C2)C2=C1 XYSZRTHDXHPSRH-UHFFFAOYSA-N 0.000 claims description 4
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- 208000000453 Skin Neoplasms Diseases 0.000 claims description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
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- 125000006693 (C2-C9) heterocyclyl group Chemical group 0.000 claims description 3
- FYAZYJJIJMWDKA-UHFFFAOYSA-N 2-(1h-indol-6-ylamino)-8-methyl-6-(4-methylphenyl)sulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=C(C=CN2)C2=C1 FYAZYJJIJMWDKA-UHFFFAOYSA-N 0.000 claims description 3
- NGLUHBKHRJWHBE-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-6-(4-chlorophenyl)sulfonyl-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C(=O)C)CCN1C1=NC=C(C=C(C(=O)N2C)S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=N1 NGLUHBKHRJWHBE-UHFFFAOYSA-N 0.000 claims description 3
- XHJRKLRJGMQTRR-UHFFFAOYSA-N 2-(4-methoxyanilino)-8-methyl-6-(4-methylphenyl)sulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=C(C(=O)N2C)S(=O)(=O)C=3C=CC(C)=CC=3)C2=N1 XHJRKLRJGMQTRR-UHFFFAOYSA-N 0.000 claims description 3
- LELLRLLLTNANMW-UHFFFAOYSA-N 4-[2-(1h-indol-5-ylamino)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]sulfonylbenzoic acid Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 LELLRLLLTNANMW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- GDRREQHJEAYYEO-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-2-(1h-indazol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=NNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F GDRREQHJEAYYEO-UHFFFAOYSA-N 0.000 claims description 3
- LEQVQBKEEKQFFF-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-8-methyl-2-[(2-oxo-1,3-dihydroindol-5-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4CC(=O)NC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F LEQVQBKEEKQFFF-UHFFFAOYSA-N 0.000 claims description 3
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| US28778409P | 2009-12-18 | 2009-12-18 | |
| US61/287,784 | 2009-12-18 | ||
| PCT/US2010/060930 WO2011075616A1 (en) | 2009-12-18 | 2010-12-17 | Substituted pyrido[2,3-d]pyrimidin-7(8h)-ones and therapeutic uses thereof |
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| JP2013514983A JP2013514983A (ja) | 2013-05-02 |
| JP2013514983A5 JP2013514983A5 (enExample) | 2013-12-26 |
| JP5797664B2 true JP5797664B2 (ja) | 2015-10-21 |
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| BR112013002375B1 (pt) | 2010-08-05 | 2020-05-12 | Temple University - Of The Commonwealth System Of Higher Education | Composto, processo de preparação do mesmo, composição farmacêutica, e, usos de um composto |
| US8895587B2 (en) * | 2011-05-18 | 2014-11-25 | Syngenta Participations Ag | Insecticidal compounds based on arylthioacetamide derivatives |
| EP3733184B1 (en) | 2013-03-14 | 2023-08-30 | Icahn School of Medicine at Mount Sinai | Pyrimidine compounds for use in the treatment of cancer |
| AU2015296322B2 (en) | 2014-07-26 | 2019-09-19 | Sunshine Lake Pharma Co., Ltd. | 2-amino-pyrido[2,3-d]pyrimidin-7(8h)-one derivatives as CDK inhibitors and uses thereof |
| CN111032655B (zh) * | 2017-08-31 | 2022-09-02 | 达纳-法伯癌症研究所股份有限公司 | Egfr和/或her2抑制剂和使用方法 |
| CN119215170B (zh) * | 2024-09-30 | 2025-05-06 | 中国医学科学院医学实验动物研究所 | Plk2作为抗免疫缺陷病毒感染治疗药物的新靶点及其应用 |
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| US5620981A (en) | 1995-05-03 | 1997-04-15 | Warner-Lambert Company | Pyrido [2,3-D]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation |
| US6498163B1 (en) | 1997-02-05 | 2002-12-24 | Warner-Lambert Company | Pyrido[2,3-D]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation |
| PL357634A1 (en) | 2000-01-27 | 2004-07-26 | Warner-Lambert Company | Pyridopyrimidinone derivatives for treatment of neurodegenerative disease |
| CN1438890A (zh) | 2000-02-25 | 2003-08-27 | 弗·哈夫曼-拉罗切有限公司 | 腺苷受体调制剂 |
| SK12472002A3 (sk) | 2000-03-06 | 2003-04-01 | Warner-Lambert Company | 5-Alkylpyrido[2,3-d]pyrimidínové inhibítory tyrosínových kináz |
| AU2002256615B2 (en) * | 2001-02-12 | 2007-09-13 | F. Hoffmann-La Roche Ag | 6-substituted pyrido-pyrimidines |
| JP4291696B2 (ja) * | 2002-01-22 | 2009-07-08 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 2−(ピリジン−2−イルアミノ)−ピリド[2,3−d]ピリミジン−7−オン |
| DE602004005238T2 (de) * | 2003-11-13 | 2007-11-08 | F. Hoffmann-La Roche Ag | Hydroxyalkylsubstituierte pyrido-7-pyrimidin-7-one |
| CA2555724A1 (en) | 2004-02-18 | 2005-09-09 | Warner-Lambert Company Llc | 2-(pyridin-3-ylamino)-pyrido[2,3-d]pyrimidin-7-ones |
| WO2005105097A2 (en) | 2004-04-28 | 2005-11-10 | Gpc Biotech Ag | Pyridopyrimidines for treating inflammatory and other diseases |
| CA2575804A1 (en) * | 2004-08-26 | 2006-03-02 | Boehringer Ingelheim International Gmbh | Pteridinones used as plk (polo like kinase) inhibitors |
| US20060142312A1 (en) | 2004-12-23 | 2006-06-29 | Pfizer Inc | C6-aryl and heteroaryl substituted pyrido[2,3-D] pyrimidin-7-ones |
| GB0428475D0 (en) | 2004-12-30 | 2005-02-02 | 4 Aza Bioscience Nv | Pyrido(3,2-D)pyrimidine derivatives and pharmaceutical compositions useful as medicines for the treatment of autoimmune disorders |
| JP5480503B2 (ja) | 2005-10-07 | 2014-04-23 | エクセリクシス, インク. | PI3Kαのピリドピリミジノン型阻害剤 |
| US20090191193A1 (en) * | 2006-08-02 | 2009-07-30 | Temple University-Of The Commonwealth System Of Higher Education | Aryl Vinyl Sulfides, Sulfones, Sulfoxides and Sulfonamides, Derivatives Thereof and Therapeutic Uses Thereof |
| EP2084159A1 (en) | 2006-10-16 | 2009-08-05 | GPC Biotech Inc. | Pyrido ý2, 3-d¨pyrimidines and their use as kinase inhibitors |
| WO2008150260A1 (en) | 2007-06-06 | 2008-12-11 | Gpc Biotech, Inc. | 8-oxy-2-aminopyrido (2, 3-d) pyrimidin-7-one derivatives as kinase inhibitors and anticancer agents |
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| IL220448A0 (en) | 2012-08-30 |
| US20120269831A1 (en) | 2012-10-25 |
| KR20120125256A (ko) | 2012-11-14 |
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| CA2784749C (en) | 2017-12-12 |
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| EP2512250A1 (en) | 2012-10-24 |
| US8889696B2 (en) | 2014-11-18 |
| IL220448A (en) | 2015-04-30 |
| WO2011075616A1 (en) | 2011-06-23 |
| JP2013514983A (ja) | 2013-05-02 |
| KR101754664B1 (ko) | 2017-07-06 |
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