ES2247078T3 - Derivados 4-amino-5-ciano-2-anilino-pirimidinicos y su uso como inhibidores de quinasas del ciclo celular. - Google Patents
Derivados 4-amino-5-ciano-2-anilino-pirimidinicos y su uso como inhibidores de quinasas del ciclo celular.Info
- Publication number
- ES2247078T3 ES2247078T3 ES01914026T ES01914026T ES2247078T3 ES 2247078 T3 ES2247078 T3 ES 2247078T3 ES 01914026 T ES01914026 T ES 01914026T ES 01914026 T ES01914026 T ES 01914026T ES 2247078 T3 ES2247078 T3 ES 2247078T3
- Authority
- ES
- Spain
- Prior art keywords
- sulfamoyl
- alkyl
- formula
- amino
- compound
- Prior art date
- 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 - Lifetime
Links
- 230000022131 cell cycle Effects 0.000 title claims abstract description 13
- 239000003112 inhibitor Substances 0.000 title abstract description 19
- -1 nitro, cyano, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 claims abstract description 184
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 85
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 150000002148 esters Chemical class 0.000 claims abstract description 42
- 238000001727 in vivo Methods 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
- 230000004663 cell proliferation Effects 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 230000035755 proliferation Effects 0.000 claims description 5
- 206010051113 Arterial restenosis Diseases 0.000 claims description 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims description 4
- 208000020084 Bone disease Diseases 0.000 claims description 4
- 208000007766 Kaposi sarcoma Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 208000030533 eye disease Diseases 0.000 claims description 4
- 230000000893 fibroproliferative effect Effects 0.000 claims description 4
- 201000011066 hemangioma Diseases 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 3
- 208000030090 Acute Disease Diseases 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000038016 acute inflammation Diseases 0.000 claims description 3
- 230000006022 acute inflammation Effects 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
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- 208000037976 chronic inflammation Diseases 0.000 claims description 3
- 230000006020 chronic inflammation Effects 0.000 claims description 3
- 208000020832 chronic kidney disease Diseases 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- YHHJWBDAGVDXLS-UHFFFAOYSA-N 2-hydroxyethyl 2-[(4-amino-5-cyanopyrimidin-2-yl)amino]benzoate Chemical compound C1=C(C#N)C(N)=NC(NC=2C(=CC=CC=2)C(=O)OCCO)=N1 YHHJWBDAGVDXLS-UHFFFAOYSA-N 0.000 claims description 2
- MCHXHSNAJDIKOX-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-(2-methoxyethyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCOC)=CC=C1NC1=NC=C(C#N)C(N)=N1 MCHXHSNAJDIKOX-UHFFFAOYSA-N 0.000 claims description 2
- ZLMBLHDJLPEODA-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-(2-piperidin-1-ylethyl)benzenesulfonamide Chemical compound C1=C(C#N)C(N)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCCCC2)=N1 ZLMBLHDJLPEODA-UHFFFAOYSA-N 0.000 claims description 2
- PKRAFWFAAQOEMY-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-(3-methoxypropyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCCOC)=CC=C1NC1=NC=C(C#N)C(N)=N1 PKRAFWFAAQOEMY-UHFFFAOYSA-N 0.000 claims description 2
- BLDMSNNZSWYEKM-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-(oxolan-2-ylmethyl)benzenesulfonamide Chemical compound C1=C(C#N)C(N)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC2OCCC2)=N1 BLDMSNNZSWYEKM-UHFFFAOYSA-N 0.000 claims description 2
- TVUQCUYUYUUBIT-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-[(4-fluorophenyl)methyl]benzenesulfonamide Chemical compound C1=C(C#N)C(N)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCC=2C=CC(F)=CC=2)=N1 TVUQCUYUYUUBIT-UHFFFAOYSA-N 0.000 claims description 2
- MNLIPYXFRZPLIH-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-[2-(propan-2-ylamino)ethyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCNC(C)C)=CC=C1NC1=NC=C(C#N)C(N)=N1 MNLIPYXFRZPLIH-UHFFFAOYSA-N 0.000 claims description 2
- XXBZKQABFLVCBR-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-[3-(propan-2-ylamino)propyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCCNC(C)C)=CC=C1NC1=NC=C(C#N)C(N)=N1 XXBZKQABFLVCBR-UHFFFAOYSA-N 0.000 claims description 2
- IBOVTBANDDSIMT-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-cyclopropylbenzenesulfonamide Chemical compound C1=C(C#N)C(N)=NC(NC=2C=CC(=CC=2)S(=O)(=O)NC2CC2)=N1 IBOVTBANDDSIMT-UHFFFAOYSA-N 0.000 claims description 2
- FOMCMGVSAMDTAH-UHFFFAOYSA-N 4-[(4-amino-5-cyanopyrimidin-2-yl)amino]-n-propylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1NC1=NC=C(C#N)C(N)=N1 FOMCMGVSAMDTAH-UHFFFAOYSA-N 0.000 claims description 2
- GSNMXUBZXPYQQE-UHFFFAOYSA-N 4-amino-2-(2,4-dimethylanilino)pyrimidine-5-carbonitrile Chemical compound CC1=CC(C)=CC=C1NC1=NC=C(C#N)C(N)=N1 GSNMXUBZXPYQQE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- QCSKBYGDMGDAGR-UHFFFAOYSA-N methyl 2-[(4-amino-5-cyanopyrimidin-2-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC1=NC=C(C#N)C(N)=N1 QCSKBYGDMGDAGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 230000001012 protector Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 abstract description 18
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- 125000000304 alkynyl group Chemical group 0.000 abstract 2
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- 210000004027 cell Anatomy 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
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- 125000002252 acyl group Chemical group 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Neurology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0007371 | 2000-03-28 | ||
| GBGB0007371.8A GB0007371D0 (en) | 2000-03-28 | 2000-03-28 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2247078T3 true ES2247078T3 (es) | 2006-03-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01914026T Expired - Lifetime ES2247078T3 (es) | 2000-03-28 | 2001-03-23 | Derivados 4-amino-5-ciano-2-anilino-pirimidinicos y su uso como inhibidores de quinasas del ciclo celular. |
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| EP (1) | EP1268445B1 (enExample) |
| JP (1) | JP2003528861A (enExample) |
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| AT (1) | ATE303366T1 (enExample) |
| AU (2) | AU3941401A (enExample) |
| BR (1) | BR0109577A (enExample) |
| CA (1) | CA2399864A1 (enExample) |
| DE (1) | DE60113080T2 (enExample) |
| DK (1) | DK1268445T3 (enExample) |
| ES (1) | ES2247078T3 (enExample) |
| GB (1) | GB0007371D0 (enExample) |
| IL (2) | IL151392A0 (enExample) |
| MX (1) | MXPA02009255A (enExample) |
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| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
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| GB0113041D0 (en) | 2001-05-30 | 2001-07-18 | Astrazeneca Ab | Chemical compounds |
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| EP1438053B1 (de) | 2001-10-17 | 2008-09-10 | Boehringer Ingelheim Pharma GmbH & Co.KG | Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung |
| WO2003062246A1 (en) * | 2002-01-22 | 2003-07-31 | Warner-Lambert Company Llc | 2-thia-1,6,8-triaza-naphtalene-2,2-dioxides as cdk inhibitors |
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| US7442697B2 (en) | 2002-03-09 | 2008-10-28 | Astrazeneca Ab | 4-imidazolyl substituted pyrimidine derivatives with CDK inhibitory activity |
| GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| EA200500721A1 (ru) * | 2002-11-28 | 2005-12-29 | Шеринг Акциенгезельшафт | Пиримидины, ингибирующие chk, pdk и акт, их получение и применение в качестве лекарственных средств |
| GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| WO2005058341A2 (en) * | 2003-12-11 | 2005-06-30 | Theravance, Inc. | Compositions for use in the treatment of mutant receptor tyrosine kinase driven cellular proliferative diseases |
| TW200528101A (en) | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
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| AU2006274733B2 (en) * | 2005-07-30 | 2010-09-16 | Astrazeneca Ab | Imidazolyl-pyrimidine compounds for use in the treatment of proliferative disorders |
| BRPI0616722A2 (pt) | 2005-09-30 | 2012-12-25 | Astrazeneca Ab | composto ou um sal farmaceuticamente aceitÁvel ou um Éster hidrolisÁvel in vivo do mesmo, processo para preparar o mesmo, composiÇço farmacÊutica, uso de um composto ou um sal farmaceuticamente aceitÁvel ou um Éster hidrolisÁvel in vivo do mesmo, e, mÉtodos para produzir um efeito anti-proliferaÇço celular e um efeito inibidor cdk2, para tratar cÂncer, e para tratar doenÇas |
| US7713987B2 (en) | 2005-12-06 | 2010-05-11 | Rigel Pharmaceuticals, Inc. | Pyrimidine-2,4-diamines and their uses |
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| TW200811169A (en) * | 2006-05-26 | 2008-03-01 | Astrazeneca Ab | Chemical compounds |
| BRPI0821209A2 (pt) | 2007-12-19 | 2019-09-24 | Amgen Inc | composto, composição farmacêutica, métodos de tratar câncer, para reduzir o tamanho de tumor, para tratar distúrbios, e para reduzir metástase em um tumor. |
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| AU2001239414B2 (en) | 2004-09-02 |
| BR0109577A (pt) | 2003-01-28 |
| ZA200206957B (en) | 2003-12-01 |
| EP1268445B1 (en) | 2005-08-31 |
| NO324228B1 (no) | 2007-09-10 |
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| MXPA02009255A (es) | 2003-03-12 |
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| ATE303366T1 (de) | 2005-09-15 |
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