MX2009002069A - Sintesis de 2-(piridin-2-ilamino)pirido[2,3-d]pirimidin-7-onas. - Google Patents
Sintesis de 2-(piridin-2-ilamino)pirido[2,3-d]pirimidin-7-onas.Info
- Publication number
- MX2009002069A MX2009002069A MX2009002069A MX2009002069A MX2009002069A MX 2009002069 A MX2009002069 A MX 2009002069A MX 2009002069 A MX2009002069 A MX 2009002069A MX 2009002069 A MX2009002069 A MX 2009002069A MX 2009002069 A MX2009002069 A MX 2009002069A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- formula
- palladium
- bis
- alkyl
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title description 6
- 238000003786 synthesis reaction Methods 0.000 title description 5
- DDZFNEVGSZKHPR-UHFFFAOYSA-N 2-(pyridin-2-ylamino)-6h-pyrido[2,3-d]pyrimidin-7-one Chemical class N=1C2=NC(=O)CC=C2C=NC=1NC1=CC=CC=N1 DDZFNEVGSZKHPR-UHFFFAOYSA-N 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims description 142
- -1 phosphine compound Chemical class 0.000 claims description 89
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 27
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 17
- 229910052723 transition metal Inorganic materials 0.000 claims description 17
- 150000003624 transition metals Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 16
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 14
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims description 10
- 229940125904 compound 1 Drugs 0.000 claims description 10
- 230000026030 halogenation Effects 0.000 claims description 10
- 238000005658 halogenation reaction Methods 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- WXNOJTUTEXAZLD-UHFFFAOYSA-L benzonitrile;dichloropalladium Chemical compound Cl[Pd]Cl.N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WXNOJTUTEXAZLD-UHFFFAOYSA-L 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical group [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 7
- HPEWFYSUPRQTJQ-UHFFFAOYSA-N [CH-]1C=CC=C1.[CH-]1C=CC=C1.C1=CC=C[C-]1P(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=C[C-]1P(C1=CC=CC=C1)C1=CC=CC=C1.Cl.Cl.[Fe+2].[Fe+2] Chemical compound [CH-]1C=CC=C1.[CH-]1C=CC=C1.C1=CC=C[C-]1P(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=C[C-]1P(C1=CC=CC=C1)C1=CC=CC=C1.Cl.Cl.[Fe+2].[Fe+2] HPEWFYSUPRQTJQ-UHFFFAOYSA-N 0.000 claims description 7
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 claims description 7
- 229940045996 isethionic acid Drugs 0.000 claims description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- 239000001632 sodium acetate Substances 0.000 claims description 7
- 235000017281 sodium acetate Nutrition 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 235000011056 potassium acetate Nutrition 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 235000011054 acetic acid Nutrition 0.000 claims description 5
- 230000002140 halogenating effect Effects 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 5
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 5
- 150000002941 palladium compounds Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- QVQGTNFYPJQJNM-UHFFFAOYSA-N dicyclohexylmethanamine Chemical compound C1CCCCC1C(N)C1CCCCC1 QVQGTNFYPJQJNM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000007822 coupling agent Substances 0.000 claims description 3
- KFGVRWGDTLZAAO-UHFFFAOYSA-N cyclopenta-1,3-diene dicyclohexyl(cyclopenta-1,3-dien-1-yl)phosphane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.C1CCC(CC1)P(C1CCCCC1)c1ccc[cH-]1 KFGVRWGDTLZAAO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000003457 sulfones Chemical group 0.000 claims description 3
- 150000003462 sulfoxides Chemical group 0.000 claims description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 2
- AGCOMFFHXJMNLN-UHFFFAOYSA-N dichloromethane;dihydrochloride Chemical compound Cl.Cl.ClCCl AGCOMFFHXJMNLN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims 3
- UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 claims 2
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 43
- 230000002062 proliferating effect Effects 0.000 abstract description 8
- 239000002585 base Substances 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- VICSJCCJGPGBMW-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1.CC(C)(C)OC(=O)N1CCNCC1 VICSJCCJGPGBMW-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
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- 229940124597 therapeutic agent Drugs 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
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| US84305106P | 2006-09-08 | 2006-09-08 | |
| US94210407P | 2007-06-05 | 2007-06-05 | |
| PCT/IB2007/002524 WO2008032157A2 (en) | 2006-09-08 | 2007-08-27 | Synthesis of 2-(pyridin-2-ylamino)-pyrido[2,3-d]pyrimidin-7-ones |
Publications (1)
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| MX2009002069A true MX2009002069A (es) | 2009-03-06 |
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| MX2009002069A MX2009002069A (es) | 2006-09-08 | 2007-08-27 | Sintesis de 2-(piridin-2-ilamino)pirido[2,3-d]pirimidin-7-onas. |
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| 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. |
| US8389533B2 (en) * | 2008-04-07 | 2013-03-05 | Amgen Inc. | Gem-disubstituted and spirocyclic amino pyridines/pyrimidines as cell cycle inhibitors |
| US9294421B2 (en) * | 2009-03-23 | 2016-03-22 | Google Inc. | System and method for merging edits for a conversation in a hosted conversation system |
| PH12012501361A1 (en) | 2009-12-31 | 2012-10-22 | Centro Nac De Investigaciones Oncologicas Cnio | Tricyclic compounds for use as kinase inhibitors |
| WO2012098387A1 (en) | 2011-01-18 | 2012-07-26 | Centro Nacional De Investigaciones Oncológicas (Cnio) | 6, 7-ring-fused triazolo [4, 3 - b] pyridazine derivatives as pim inhibitors |
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| US20240398832A1 (en) | 2021-12-10 | 2024-12-05 | Eli Lilly And Company | Cdk4 and 6 inhibitor in combination with fulvestrant for the treatment of hormone receptor-positive, human epidermal growth factor receptor 2-negative advanced or metastatic breast cancer in patients previously treated with a cdk4 and 6 inhibitor |
| WO2023111810A1 (en) | 2021-12-14 | 2023-06-22 | Pfizer Inc. | Combination therapies and uses for treating cancer |
| WO2023114264A1 (en) | 2021-12-15 | 2023-06-22 | Eli Lilly And Company | Combination for treatment of high-risk metastatic hormone-sensitive prostate cancer |
| EP4561571A1 (en) | 2022-07-29 | 2025-06-04 | Pfizer Inc. | Dosing regimens comprising a kat6 inhibitor for the treatment of cancer |
| EP4580631A1 (en) | 2022-08-31 | 2025-07-09 | Arvinas Operations, Inc. | Dosage regimens of estrogen receptor degraders |
| EP4611739A1 (en) | 2022-11-02 | 2025-09-10 | Petra Pharma Corporation | Allosteric chromenone inhibitors of phosphoinositide 3-kinase (pi3k) for the treatment of disease |
| CN116283969B (zh) * | 2023-02-24 | 2024-11-19 | 杭州新曦科技有限公司 | 用于制备帕博西尼及其相关中间体的方法 |
| CN120981721A (zh) | 2023-03-30 | 2025-11-18 | 辉瑞大药厂 | Kat6a作为用kat6a抑制剂治疗的预测性生物标志物和相关治疗方法 |
| WO2024201340A1 (en) | 2023-03-30 | 2024-10-03 | Pfizer Inc. | Kat6a as a predictive biomarker for treatment of breast cancer with a cdk4 inhibitor and an antiestrogen and methods of treatment thereof |
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| CN118834207A (zh) * | 2024-06-26 | 2024-10-25 | 安徽大学 | 一种2-氯-8-环戊基-5-甲基-8h-吡啶并[2,3-d]嘧啶基-7-酮的合成方法 |
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| CN101001857B (zh) * | 2002-01-22 | 2011-06-22 | 沃尼尔·朗伯有限责任公司 | 2-(吡啶-2-基氨基)-吡啶并[2,3-d]嘧啶-7-酮 |
| DK1648889T3 (da) * | 2003-07-11 | 2009-01-05 | Warner Lambert Co | Isethionatsalt af en selektiv CDK4-inhibitor |
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- 2007-08-27 BR BRPI0716880-2A2A patent/BRPI0716880A2/pt not_active IP Right Cessation
- 2007-08-27 CN CNA2007800334161A patent/CN101511829A/zh active Pending
- 2007-08-27 RU RU2009108006/04A patent/RU2009108006A/ru not_active Application Discontinuation
- 2007-08-27 AU AU2007297286A patent/AU2007297286A1/en not_active Abandoned
- 2007-08-27 CA CA002662768A patent/CA2662768A1/en not_active Abandoned
- 2007-08-27 WO PCT/IB2007/002524 patent/WO2008032157A2/en not_active Ceased
- 2007-08-27 MX MX2009002069A patent/MX2009002069A/es not_active Application Discontinuation
- 2007-08-27 KR KR1020097007146A patent/KR20090052385A/ko not_active Ceased
- 2007-09-06 AR ARP070103937A patent/AR062680A1/es not_active Application Discontinuation
- 2007-09-07 TW TW096133457A patent/TW200821309A/zh unknown
- 2007-09-07 JP JP2007232730A patent/JP2008094834A/ja not_active Withdrawn
- 2007-09-10 US US11/852,873 patent/US7781583B2/en not_active Expired - Fee Related
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- 2009-02-25 IL IL197242A patent/IL197242A0/en unknown
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| US7781583B2 (en) | 2010-08-24 |
| US20080125588A1 (en) | 2008-05-29 |
| AU2007297286A1 (en) | 2008-03-20 |
| EP2069344A2 (en) | 2009-06-17 |
| CN101511829A (zh) | 2009-08-19 |
| RU2009108006A (ru) | 2010-10-20 |
| CA2662768A1 (en) | 2008-03-20 |
| ZA200901270B (en) | 2010-05-26 |
| BRPI0716880A2 (pt) | 2013-10-15 |
| WO2008032157A3 (en) | 2008-10-23 |
| IL197242A0 (en) | 2009-12-24 |
| TW200821309A (en) | 2008-05-16 |
| AR062680A1 (es) | 2008-11-26 |
| JP2008094834A (ja) | 2008-04-24 |
| WO2008032157A2 (en) | 2008-03-20 |
| KR20090052385A (ko) | 2009-05-25 |
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