ZA200601963B - 2,4 Di (hetero)-arylamino-pyrimidine derivatives as ZAP-70 and/or Syk inhibitors - Google Patents
2,4 Di (hetero)-arylamino-pyrimidine derivatives as ZAP-70 and/or Syk inhibitors Download PDFInfo
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- ZA200601963B ZA200601963B ZA200601963A ZA200601963A ZA200601963B ZA 200601963 B ZA200601963 B ZA 200601963B ZA 200601963 A ZA200601963 A ZA 200601963A ZA 200601963 A ZA200601963 A ZA 200601963A ZA 200601963 B ZA200601963 B ZA 200601963B
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- 125000005842 heteroatom Chemical group 0.000 title claims description 19
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
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- -1 C-Cyalkaxy Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
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- UBFZMLJERNWJCZ-UHFFFAOYSA-N 2-amino-6-(dimethylamino)benzenesulfonamide Chemical compound CN(C)C1=CC=CC(N)=C1S(N)(=O)=O UBFZMLJERNWJCZ-UHFFFAOYSA-N 0.000 description 3
- XEFRNCLPPFDWAC-UHFFFAOYSA-N 3,4,5-trimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1OC XEFRNCLPPFDWAC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- JZTKJPOXZXAMIJ-UHFFFAOYSA-N 2-(dimethylamino)-6-[[2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C(=C(N(C)C)C=CC=3)S(N)(=O)=O)C=CN=2)=C1 JZTKJPOXZXAMIJ-UHFFFAOYSA-N 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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- 125000001246 bromo group Chemical group Br* 0.000 description 2
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- 238000000605 extraction Methods 0.000 description 2
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- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
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- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
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- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- BZKOZYWGZKRTIB-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-amine Chemical compound O1CCOC2=CC(N)=CC=C21 BZKOZYWGZKRTIB-UHFFFAOYSA-N 0.000 description 1
- LEWZOBYWGWKNCK-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-amine Chemical compound NC1=CC=C2CCCC2=C1 LEWZOBYWGWKNCK-UHFFFAOYSA-N 0.000 description 1
- YDMLBSFKMTXIDJ-UHFFFAOYSA-N 2-[[2-(3,4-dimethoxyanilino)pyrimidin-4-yl]amino]-6-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=CC(NC=2C(=C(OC(F)(F)F)C=CC=2)S(N)(=O)=O)=N1 YDMLBSFKMTXIDJ-UHFFFAOYSA-N 0.000 description 1
- ZPYYPVIZCAFIBS-UHFFFAOYSA-N 2-[[2-(3,4-dimethoxyanilino)pyrimidin-4-yl]amino]-6-prop-2-enoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=CC(NC=2C(=C(OCC=C)C=CC=2)S(N)(=O)=O)=N1 ZPYYPVIZCAFIBS-UHFFFAOYSA-N 0.000 description 1
- GWYOWFXEAHLULA-UHFFFAOYSA-N 2-amino-6-(trifluoromethoxy)benzenesulfonamide Chemical compound NC1=CC=CC(OC(F)(F)F)=C1S(N)(=O)=O GWYOWFXEAHLULA-UHFFFAOYSA-N 0.000 description 1
- ACUFLNWNUQBRFN-UHFFFAOYSA-N 2-chloro-6-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=C(Cl)C=CC=C1[N+]([O-])=O ACUFLNWNUQBRFN-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- HFCFJYRLBAANKN-UHFFFAOYSA-N 2-methyl-3-nitroaniline Chemical compound CC1=C(N)C=CC=C1[N+]([O-])=O HFCFJYRLBAANKN-UHFFFAOYSA-N 0.000 description 1
- UYHSQVMHSFXUOA-UHFFFAOYSA-N 2-methylthiouracil Chemical compound CSC1=NC=CC(O)=N1 UYHSQVMHSFXUOA-UHFFFAOYSA-N 0.000 description 1
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- UMYMICJAEFKYND-UHFFFAOYSA-N 5,6-dichloro-5-nitrocyclohexa-1,3-diene Chemical compound ClC1C=CC=CC1([N+](=O)[O-])Cl UMYMICJAEFKYND-UHFFFAOYSA-N 0.000 description 1
- MPVSHKRXVYRFHY-UHFFFAOYSA-N 5-[[2-(3,4,5-trimethoxyanilino)pyrimidin-4-yl]amino]-2,3-dihydro-1h-indene-4-sulfonamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(NC=3C(=C4CCCC4=CC=3)S(N)(=O)=O)C=CN=2)=C1 MPVSHKRXVYRFHY-UHFFFAOYSA-N 0.000 description 1
- AAPNMNWWBLOWLI-UHFFFAOYSA-N 5-amino-2,3-dihydro-1H-indene-4-sulfonamide Chemical compound NC1=C(C=2CCCC2C=C1)S(=O)(=O)N.NC1=C(C=2CCCC2C=C1)S(=O)(=O)N AAPNMNWWBLOWLI-UHFFFAOYSA-N 0.000 description 1
- JMCYMXIDMSCABY-UHFFFAOYSA-N 5-amino-2,3-dihydro-1h-indene-4-sulfonamide Chemical compound NC1=CC=C2CCCC2=C1S(N)(=O)=O JMCYMXIDMSCABY-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910006074 SO2NH2 Inorganic materials 0.000 description 1
- 101100391171 Schizosaccharomyces pombe (strain 972 / ATCC 24843) for3 gene Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- ACXOYRULDUFYJB-UHFFFAOYSA-N [N].O1CCOC2=CC(N)=CC=C21 Chemical compound [N].O1CCOC2=CC(N)=CC=C21 ACXOYRULDUFYJB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HLNPDVKKRBWQAA-UHFFFAOYSA-M amino(trimethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)N HLNPDVKKRBWQAA-UHFFFAOYSA-M 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ZVYXEXAXXWINEH-UHFFFAOYSA-N n,n-diethyl-2-hydroxybenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1O ZVYXEXAXXWINEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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| ATE451104T1 (de) | 2002-07-29 | 2009-12-15 | Rigel Pharmaceuticals Inc | Verfahren zur behandlung oder pruvention von autoimmunkrankheiten mit 2,4-pyrimidindiamin- verbindungen |
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| PL1656372T3 (pl) | 2003-07-30 | 2013-08-30 | Rigel Pharmaceuticals Inc | Związki 2,4-pirymidynodiaminy do stosowania w leczeniu lub zapobieganiu chorobom autoimmunologicznym |
| CA2533320A1 (fr) * | 2003-08-15 | 2006-02-24 | Novartis Ag | 2, 4-pyrimidine diamines utiles dans le cadre du traitement de maladies neoplasiques, de troubles inflammatoires et de troubles du systeme immunitaire |
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| BRPI0606318B8 (pt) | 2005-01-19 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, composição, e, uso de um composto |
| EP1856075A1 (fr) * | 2005-01-25 | 2007-11-21 | Epix Delaware, Inc. | Composes d'arylamine substitues et leur utilisation comme modulateurs de 5-ht6 |
| WO2006129100A1 (fr) * | 2005-06-03 | 2006-12-07 | Glaxo Group Limited | Nouveaux composes |
| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| WO2006133426A2 (fr) | 2005-06-08 | 2006-12-14 | Rigel Pharmaceuticals, Inc. | Compositions et procedes d'inhibition de la voie jak |
| GB0517329D0 (en) * | 2005-08-25 | 2005-10-05 | Merck Sharp & Dohme | Stimulation of neurogenesis |
| US7528143B2 (en) * | 2005-11-01 | 2009-05-05 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| US8133900B2 (en) | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| US8604042B2 (en) | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| WO2007120339A1 (fr) * | 2005-12-19 | 2007-10-25 | Genentech, Inc. | Inhibiteurs de pyrimidine kinase |
| WO2007085540A1 (fr) * | 2006-01-27 | 2007-08-02 | Glaxo Group Limited | Derives 1h-indaz0l-4-yl-2,4-pyrimidinediamine |
| WO2007089768A2 (fr) * | 2006-01-30 | 2007-08-09 | Exelixis, Inc. | 4-aryl-2-amino-pyrimidines ou 4-aryl-2-aminoalkyl-pyrimidines utilisées comme modulateurs de la jak-2 et leurs procédés d'utilisation |
| SI1984357T1 (sl) | 2006-02-17 | 2014-02-28 | Rigel Pharmaceuticals, Inc. | Spojine 2,4-pirimidindiamina za zdravljenje ali preventivo avtoimunih bolezni |
| ES2622493T3 (es) | 2006-02-24 | 2017-07-06 | Rigel Pharmaceuticals, Inc. | Composiciones y métodos para la inhibición de la ruta de JAK |
| US8168383B2 (en) | 2006-04-14 | 2012-05-01 | Cell Signaling Technology, Inc. | Gene defects and mutant ALK kinase in human solid tumors |
| ES2637592T3 (es) | 2006-04-14 | 2017-10-13 | Cell Signaling Technology, Inc. | Defectos de genes y quinasa ALK mutante en tumores sólidos humanos |
| EP2222647B1 (fr) | 2006-10-23 | 2015-08-05 | Cephalon, Inc. | Dérives bicycliques fusionnes de 2,4-diaminopyrimidine utilises comme inhibiteurs de alk et c-met |
| SI2091918T1 (sl) | 2006-12-08 | 2015-01-30 | Irm Llc | Spojine in sestavki kot inhibitorji protein-kinaze |
| CN101563327A (zh) * | 2006-12-19 | 2009-10-21 | 健泰科生物技术公司 | 嘧啶类激酶抑制剂 |
| PE20081636A1 (es) | 2007-01-26 | 2009-01-10 | Smithkline Beecham Corp | Inhibidores de antranilamida para aurora quinasa |
| TW200840581A (en) * | 2007-02-28 | 2008-10-16 | Astrazeneca Ab | Novel pyrimidine derivatives |
| PL2154967T3 (pl) * | 2007-04-16 | 2014-08-29 | Hutchison Medipharma Entpr Ltd | Pochodne pirymidyny |
| TWI389893B (zh) * | 2007-07-06 | 2013-03-21 | Astellas Pharma Inc | 二（芳胺基）芳基化合物 |
| KR101174201B1 (ko) | 2007-08-28 | 2012-08-16 | 아이알엠 엘엘씨 | 키나제 억제제로서의 2-비페닐아미노-4-아미노피리미딘 유도체 |
| SI2252300T1 (sl) | 2008-02-22 | 2017-04-26 | Rigel Pharmaceuticals, Inc. | Uporaba 2,4-pirimidindiaminov za zdravljenje ateroskleroze |
| CA2717529A1 (fr) * | 2008-03-11 | 2009-09-17 | Cellzome Limited | Sulfonamides en tant qu'inhibiteurs de zap-70 |
| WO2009127642A2 (fr) * | 2008-04-15 | 2009-10-22 | Cellzome Limited | Utilisation d’inhibiteurs de lrrk2 pour maladies neurodégénératives |
| NZ589315A (en) | 2008-04-16 | 2012-11-30 | Portola Pharm Inc | 2,6-diamino-pyrimidin-5-yl-carboxamides as Spleen tryosine kinase (syk) or Janus kinase (JAK) inhibitors |
| US8138339B2 (en) | 2008-04-16 | 2012-03-20 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| US7829574B2 (en) | 2008-05-09 | 2010-11-09 | Hutchison Medipharma Enterprises Limited | Substituted quinazoline compounds and their use in treating angiogenesis-related diseases |
| HUE035029T2 (en) | 2008-05-21 | 2018-03-28 | Ariad Pharma Inc | Kinase inhibitor phosphorus derivatives |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
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