MXPA05006437A - Derivados de piridino[2,3-d]pirimidina como inhibidores selectivos de kdr y fgfr. - Google Patents
Derivados de piridino[2,3-d]pirimidina como inhibidores selectivos de kdr y fgfr.Info
- Publication number
- MXPA05006437A MXPA05006437A MXPA05006437A MXPA05006437A MXPA05006437A MX PA05006437 A MXPA05006437 A MX PA05006437A MX PA05006437 A MXPA05006437 A MX PA05006437A MX PA05006437 A MXPA05006437 A MX PA05006437A MX PA05006437 A MXPA05006437 A MX PA05006437A
- Authority
- MX
- Mexico
- Prior art keywords
- substituted
- lower alkyl
- phenyl
- pyrimidin
- propionic acid
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 12
- 150000003230 pyrimidines Chemical class 0.000 title description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 27
- 229910052786 argon Inorganic materials 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 210000000481 breast Anatomy 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 210000001072 colon Anatomy 0.000 claims abstract description 9
- 210000004072 lung Anatomy 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 172
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 69
- 125000000623 heterocyclic group Chemical group 0.000 claims description 68
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 150000002367 halogens Chemical class 0.000 claims description 63
- 125000005842 heteroatom Chemical group 0.000 claims description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- -1 2,6-dichloro-phenyl Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 101100173726 Arabidopsis thaliana OR23 gene Proteins 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 201000011510 cancer Diseases 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
- 208000026310 Breast neoplasm Diseases 0.000 claims description 10
- 208000029742 colonic neoplasm Diseases 0.000 claims description 10
- CJHTXCOXQJEHAV-UHFFFAOYSA-N methyl 3-(2,4-dianilinopyrimidin-5-yl)-2-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(=O)OC)CC(C(=N1)NC=2C=CC=CC=2)=CN=C1NC1=CC=CC=C1 CJHTXCOXQJEHAV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- BNSNEYFSBZJQHZ-UHFFFAOYSA-N methyl 3-(2,4-dichloropyrimidin-5-yl)-2-(3,5-dimethoxyphenyl)propanoate Chemical compound C=1C(OC)=CC(OC)=CC=1C(C(=O)OC)CC1=CN=C(Cl)N=C1Cl BNSNEYFSBZJQHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- JVJSOURCIHXXBR-UHFFFAOYSA-N ethyl 3-(2,4-dianilinopyrimidin-5-yl)-2-pyridin-4-ylpropanoate Chemical compound C=1C=NC=CC=1C(C(=O)OCC)CC(C(=N1)NC=2C=CC=CC=2)=CN=C1NC1=CC=CC=C1 JVJSOURCIHXXBR-UHFFFAOYSA-N 0.000 claims description 7
- LFECLVXEHCFTCS-UHFFFAOYSA-N ethyl 3-(2,4-dichloropyrimidin-5-yl)-2-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(C(=O)OCC)CC1=CN=C(Cl)N=C1Cl LFECLVXEHCFTCS-UHFFFAOYSA-N 0.000 claims description 7
- AKABDZICYIWPDV-UHFFFAOYSA-N methyl 3-[4-anilino-2-[(6-methoxypyridin-3-yl)amino]pyrimidin-5-yl]-2-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(=O)OC)CC(C(=N1)NC=2C=CC=CC=2)=CN=C1NC1=CC=C(OC)N=C1 AKABDZICYIWPDV-UHFFFAOYSA-N 0.000 claims description 7
- JRQIBVOYUXEJIW-UHFFFAOYSA-N 2-anilino-6-(2,5-dimethoxyphenyl)-8-phenyl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC=C(OC)C(C2C(N(C3=NC(NC=4C=CC=CC=4)=NC=C3C2)C=2C=CC=CC=2)=O)=C1 JRQIBVOYUXEJIW-UHFFFAOYSA-N 0.000 claims description 6
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 6
- REOYUZPGHQSTQM-UHFFFAOYSA-N ethyl 3-(2,4-dianilinopyrimidin-5-yl)-2-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(C(=O)OCC)CC(C(=N1)NC=2C=CC=CC=2)=CN=C1NC1=CC=CC=C1 REOYUZPGHQSTQM-UHFFFAOYSA-N 0.000 claims description 6
- SWSOUWONGSCLAO-UHFFFAOYSA-N ethyl 3-(2,4-dichloropyrimidin-5-yl)-2-(2,5-dimethoxyphenyl)propanoate Chemical compound C=1C(OC)=CC=C(OC)C=1C(C(=O)OCC)CC1=CN=C(Cl)N=C1Cl SWSOUWONGSCLAO-UHFFFAOYSA-N 0.000 claims description 6
- IWFGEGPRCZYRBC-UHFFFAOYSA-N ethyl 3-(2,4-dichloropyrimidin-5-yl)-2-pyridin-4-ylpropanoate Chemical compound C=1C=NC=CC=1C(C(=O)OCC)CC1=CN=C(Cl)N=C1Cl IWFGEGPRCZYRBC-UHFFFAOYSA-N 0.000 claims description 6
- TVFFUJKYOVNIPR-UHFFFAOYSA-N methyl 2-(2,6-dichlorophenyl)-3-(2,4-dichloropyrimidin-5-yl)propanoate Chemical compound ClC=1C=CC=C(Cl)C=1C(C(=O)OC)CC1=CN=C(Cl)N=C1Cl TVFFUJKYOVNIPR-UHFFFAOYSA-N 0.000 claims description 6
- XMWRLCCDUVRRBL-UHFFFAOYSA-N methyl 2-[3,5-bis(trifluoromethyl)phenyl]-3-(2,4-dianilinopyrimidin-5-yl)propanoate Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C(=O)OC)CC(C(=N1)NC=2C=CC=CC=2)=CN=C1NC1=CC=CC=C1 XMWRLCCDUVRRBL-UHFFFAOYSA-N 0.000 claims description 6
- KGZGUQYOCQLUTE-UHFFFAOYSA-N methyl 3-(4-anilino-2-chloropyrimidin-5-yl)-2-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(=O)OC)CC1=CN=C(Cl)N=C1NC1=CC=CC=C1 KGZGUQYOCQLUTE-UHFFFAOYSA-N 0.000 claims description 6
- PJBWKDKKFQGFBV-UHFFFAOYSA-N methyl 3-[2-anilino-4-(2-methylpropylamino)pyrimidin-5-yl]-2-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(=O)OC)CC(C(=N1)NCC(C)C)=CN=C1NC1=CC=CC=C1 PJBWKDKKFQGFBV-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 5
- HNJCPWULRKXSLE-UHFFFAOYSA-N 2-anilino-6-(4-methoxyphenyl)-8-(2-methylpropyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C1C(=O)N(CC(C)C)C2=NC(NC=3C=CC=CC=3)=NC=C2C1 HNJCPWULRKXSLE-UHFFFAOYSA-N 0.000 claims description 5
- APFYHLDWEOGXQM-UHFFFAOYSA-N 2-anilino-6-[3,5-bis(trifluoromethyl)phenyl]-8-phenyl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2C(N(C3=NC(NC=4C=CC=CC=4)=NC=C3C2)C=2C=CC=CC=2)=O)=C1 APFYHLDWEOGXQM-UHFFFAOYSA-N 0.000 claims description 5
- PJTGIOFFDNLJBZ-UHFFFAOYSA-N 2-anilino-8-phenyl-6-pyridin-4-yl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C=3C=CC=CC=3)C(=O)C(C=3C=CN=CC=3)CC2=CN=C1NC1=CC=CC=C1 PJTGIOFFDNLJBZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 201000005202 lung cancer Diseases 0.000 claims description 5
- 208000020816 lung neoplasm Diseases 0.000 claims description 5
- WAOGDYLJXXAFTE-UHFFFAOYSA-N methyl 3-(2-anilino-4-chloropyrimidin-5-yl)-2-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(=O)OC)CC(C(=N1)Cl)=CN=C1NC1=CC=CC=C1 WAOGDYLJXXAFTE-UHFFFAOYSA-N 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- KMZUGCAUUGYOML-UHFFFAOYSA-N methyl 3-(2,4-dianilinopyrimidin-5-yl)-2-(2,6-dichlorophenyl)propanoate Chemical compound ClC=1C=CC=C(Cl)C=1C(C(=O)OC)CC(C(=N1)NC=2C=CC=CC=2)=CN=C1NC1=CC=CC=C1 KMZUGCAUUGYOML-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- LDBUGKOPMCHTDP-UHFFFAOYSA-N 2-anilino-6,8-diphenyl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C=3C=CC=CC=3)C(=O)C(C=3C=CC=CC=3)CC2=CN=C1NC1=CC=CC=C1 LDBUGKOPMCHTDP-UHFFFAOYSA-N 0.000 claims description 3
- WMRQLRVQUZGQAU-UHFFFAOYSA-N 2-anilino-6-(4-methoxyphenyl)-8-phenyl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C1C(=O)N(C=2C=CC=CC=2)C2=NC(NC=3C=CC=CC=3)=NC=C2C1 WMRQLRVQUZGQAU-UHFFFAOYSA-N 0.000 claims description 3
- RNVODJGHBTYOGP-UHFFFAOYSA-N methyl 3-[2-anilino-4-(cyclopropylmethylamino)pyrimidin-5-yl]-2-(4-methoxyphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1C(C(=O)OC)CC(C(=N1)NCC2CC2)=CN=C1NC1=CC=CC=C1 RNVODJGHBTYOGP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- SSDDMPJZNWJRCN-UHFFFAOYSA-N 2-anilino-6-(3,5-dimethoxyphenyl)-8-phenyl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=CC(OC)=CC(C2C(N(C3=NC(NC=4C=CC=CC=4)=NC=C3C2)C=2C=CC=CC=2)=O)=C1 SSDDMPJZNWJRCN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- DRSMPFSBTJWOFI-UHFFFAOYSA-N 6-(4-methoxyphenyl)-2-[(6-methoxypyridin-3-yl)amino]-8-phenyl-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1C1C(=O)N(C=2C=CC=CC=2)C2=NC(NC=3C=NC(OC)=CC=3)=NC=C2C1 DRSMPFSBTJWOFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- LZKFDEKKORWSNN-UHFFFAOYSA-N ethyl 3-(2,4-dianilinopyrimidin-5-yl)-2-(2-methoxyphenyl)propanoate Chemical compound C=1C=CC=C(OC)C=1C(C(=O)OCC)CC(C(=N1)NC=2C=CC=CC=2)=CN=C1NC1=CC=CC=C1 LZKFDEKKORWSNN-UHFFFAOYSA-N 0.000 claims description 2
- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical group BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 claims 1
- 101100160255 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YLR154C-H gene Proteins 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- COFYLUNQQJILFO-UHFFFAOYSA-N ethyl 3-(2,4-dianilinopyrimidin-5-yl)-2-(2,5-dimethoxyphenyl)propanoate Chemical compound C=1C(OC)=CC=C(OC)C=1C(C(=O)OCC)CC(C(=N1)NC=2C=CC=CC=2)=CN=C1NC1=CC=CC=C1 COFYLUNQQJILFO-UHFFFAOYSA-N 0.000 claims 1
- HDCXQTPVTAIPNZ-UHFFFAOYSA-N n-({[4-(aminosulfonyl)phenyl]amino}carbonyl)-4-methylbenzenesulfonamide Chemical group C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 HDCXQTPVTAIPNZ-UHFFFAOYSA-N 0.000 claims 1
- 108091008794 FGF receptors Proteins 0.000 abstract description 14
- 230000001028 anti-proliverative effect Effects 0.000 abstract description 5
- 208000037841 lung tumor Diseases 0.000 abstract description 4
- 208000023958 prostate neoplasm Diseases 0.000 abstract description 4
- 229940124639 Selective inhibitor Drugs 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
- 239000011541 reaction mixture Substances 0.000 description 93
- 239000000243 solution Substances 0.000 description 82
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 40
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
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- 235000019270 ammonium chloride Nutrition 0.000 description 23
- 239000012047 saturated solution Substances 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
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- UHPDMTRIBIJMNL-UHFFFAOYSA-N methyl 2-[3,5-bis(trifluoromethyl)phenyl]-3-(2,4-dichloropyrimidin-5-yl)propanoate Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C(=O)OC)CC1=CN=C(Cl)N=C1Cl UHPDMTRIBIJMNL-UHFFFAOYSA-N 0.000 description 7
- BBUHOXYFMXFEHO-UHFFFAOYSA-N methyl 3-(2,4-dichloropyrimidin-5-yl)-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(=O)OC)CC1=CN=C(Cl)N=C1Cl BBUHOXYFMXFEHO-UHFFFAOYSA-N 0.000 description 7
- 210000002966 serum Anatomy 0.000 description 7
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 239000002775 capsule Substances 0.000 description 6
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- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
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| US43496902P | 2002-12-20 | 2002-12-20 | |
| US51361503P | 2003-10-23 | 2003-10-23 | |
| PCT/EP2003/014067 WO2004056822A1 (en) | 2002-12-20 | 2003-12-11 | Pyridino `2, 3-d! pyrimidine derivatives as selective kdr and fgfr inhibitors |
Publications (1)
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|---|---|
| MXPA05006437A true MXPA05006437A (es) | 2005-08-19 |
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| MXPA05006437A MXPA05006437A (es) | 2002-12-20 | 2003-12-11 | Derivados de piridino[2,3-d]pirimidina como inhibidores selectivos de kdr y fgfr. |
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| EP (1) | EP1581531B1 (enExample) |
| JP (1) | JP2006511563A (enExample) |
| KR (1) | KR100763298B1 (enExample) |
| AR (1) | AR042532A1 (enExample) |
| AT (1) | ATE387445T1 (enExample) |
| AU (1) | AU2003294830B2 (enExample) |
| BR (1) | BR0317480A (enExample) |
| CA (1) | CA2508951A1 (enExample) |
| DE (1) | DE60319430T2 (enExample) |
| ES (1) | ES2300639T3 (enExample) |
| MX (1) | MXPA05006437A (enExample) |
| PL (1) | PL377661A1 (enExample) |
| RU (1) | RU2345077C2 (enExample) |
| WO (1) | WO2004056822A1 (enExample) |
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| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| IL166241A0 (en) * | 2002-07-29 | 2006-01-15 | Rigel Pharmaceuticals Inc | Method of treating or preventing autoimmune diseases with 2,4-pyrimidinedinediamine compounds |
| RS53109B (sr) | 2003-07-30 | 2014-06-30 | Rigel Pharmaceuticals Inc. | Jedinjenja 2,4 pirimidindiamina za upotrebu u tretmanu ili prevenciji autoimunih bolesti |
| ES2292130T3 (es) * | 2004-05-04 | 2008-03-01 | Warner-Lambert Company Llc | Pirido(2,3-d)pirimidin-7-onas pirrolil-sustituidas y derivados de las mismas como agentes terapeuticos. |
| ES2380550T3 (es) * | 2004-11-24 | 2012-05-16 | Rigel Pharmaceuticals, Inc. | Compuestos de espiro-2,4-pirimidindiamina y sus usos |
| CA2604551A1 (en) * | 2005-05-03 | 2007-03-08 | Rigel Pharmaceuticals, Inc. | Jak kinase inhibitors and their uses |
| WO2007136465A2 (en) * | 2006-05-15 | 2007-11-29 | Irm Llc | Compositions and methods for fgf receptor kinases inhibitors |
| ATE514695T1 (de) * | 2006-09-15 | 2011-07-15 | Pfizer Prod Inc | Pyrido(2,3-d)pyrimidinonverbindungen und ihre verwendung als pi3-inhibitoren |
| GB201007286D0 (en) | 2010-04-30 | 2010-06-16 | Astex Therapeutics Ltd | New compounds |
| GB201020179D0 (en) | 2010-11-29 | 2011-01-12 | Astex Therapeutics Ltd | New compounds |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
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| TJ342B (en) * | 1994-11-14 | 2002-10-06 | Warner Lambert Co | Derivatives of 6-aryl pyrido Ä2,3-dÜ pyrimidines and naphthyridines pharmaceutical composition possess inhibiting effect of cellular proliferation pr ovoking protein tyrosine kinase and method of inhibiting cellular proliferation |
| IL117923A (en) | 1995-05-03 | 2000-06-01 | Warner Lambert Co | Anti-cancer pharmaceutical compositions containing polysubstituted pyrido¬2,3-d¾pyrimidine derivatives and certain such novel compounds |
| WO1998024432A2 (en) | 1996-12-05 | 1998-06-11 | Sugen, Inc. | Use of indolinone compounds as modulators of protein kinases |
| DE69839338T2 (de) | 1997-02-05 | 2008-07-10 | Warner-Lambert Company Llc | Pyrido (2,3-d) pyrimidine und 4-amino-pyrimidine als inhibitoren der zellulären proliferation |
| CZ20011394A3 (cs) | 1998-10-23 | 2001-12-12 | F. Hoffmann-La Roche Ag | Derivát bicyklických, dusík obsahujících heterocyklických sloučenin, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje |
| CA2367867A1 (en) | 1999-03-16 | 2000-09-21 | Shell Internationale Research Maatschappij B.V. | Process for the purification of propylene oxide |
| AR030053A1 (es) | 2000-03-02 | 2003-08-13 | Smithkline Beecham Corp | 1h-pirimido [4,5-d] pirimidin-2-onas y sales, composiciones farmaceuticas, uso para la fabricacion de un medicamento y procedimiento para producirlas |
| AU2001277032A1 (en) | 2000-08-04 | 2002-02-18 | Warner Lambert Company | 2-(4-pyridyl)amino-6-dialkoxyphenyl-pyrido(2,3-d)pyrimidin-7 ones |
| JP2004505974A (ja) | 2000-08-04 | 2004-02-26 | 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、カンパニー | ２−（４−ピリジル）アミノ−６−ジアルキルオキシフェニルピリド〔２，３−ｄ〕ピリミジン−７−オン類の製造方法 |
| EP1315726A1 (en) | 2000-08-31 | 2003-06-04 | F. Hoffmann-La Roche Ag | 7- oxo pyridopyrimidines as inhibitors of cellular proliferation |
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2003
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- 2003-12-11 DE DE60319430T patent/DE60319430T2/de not_active Expired - Lifetime
- 2003-12-11 EP EP03785789A patent/EP1581531B1/en not_active Expired - Lifetime
- 2003-12-11 RU RU2005122901/04A patent/RU2345077C2/ru not_active IP Right Cessation
- 2003-12-11 BR BR0317480-8A patent/BR0317480A/pt not_active IP Right Cessation
- 2003-12-11 CA CA002508951A patent/CA2508951A1/en not_active Abandoned
- 2003-12-11 AT AT03785789T patent/ATE387445T1/de not_active IP Right Cessation
- 2003-12-11 AU AU2003294830A patent/AU2003294830B2/en not_active Expired - Fee Related
- 2003-12-11 PL PL377661A patent/PL377661A1/pl not_active Application Discontinuation
- 2003-12-11 MX MXPA05006437A patent/MXPA05006437A/es active IP Right Grant
- 2003-12-11 ES ES03785789T patent/ES2300639T3/es not_active Expired - Lifetime
- 2003-12-11 WO PCT/EP2003/014067 patent/WO2004056822A1/en not_active Ceased
- 2003-12-11 JP JP2004561276A patent/JP2006511563A/ja active Pending
- 2003-12-11 KR KR1020057011681A patent/KR100763298B1/ko not_active Expired - Fee Related
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| WO2004056822A1 (en) | 2004-07-08 |
| ATE387445T1 (de) | 2008-03-15 |
| KR100763298B1 (ko) | 2007-10-04 |
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| RU2005122901A (ru) | 2006-02-27 |
| EP1581531B1 (en) | 2008-02-27 |
| AR042532A1 (es) | 2005-06-22 |
| DE60319430D1 (de) | 2008-04-10 |
| CA2508951A1 (en) | 2004-07-08 |
| BR0317480A (pt) | 2005-11-16 |
| DE60319430T2 (de) | 2009-02-26 |
| JP2006511563A (ja) | 2006-04-06 |
| AU2003294830A1 (en) | 2004-07-14 |
| RU2345077C2 (ru) | 2009-01-27 |
| EP1581531A1 (en) | 2005-10-05 |
| AU2003294830B2 (en) | 2009-06-11 |
| US20040122029A1 (en) | 2004-06-24 |
| US7098332B2 (en) | 2006-08-29 |
| PL377661A1 (pl) | 2006-02-06 |
| ES2300639T3 (es) | 2008-06-16 |
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