EA025222B1 - Соединения и композиции в качестве ингибиторов протеинкиназ - Google Patents
Соединения и композиции в качестве ингибиторов протеинкиназ Download PDFInfo
- Publication number
- EA025222B1 EA025222B1 EA201200373A EA201200373A EA025222B1 EA 025222 B1 EA025222 B1 EA 025222B1 EA 201200373 A EA201200373 A EA 201200373A EA 201200373 A EA201200373 A EA 201200373A EA 025222 B1 EA025222 B1 EA 025222B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- propan
- amino
- pyrimidin
- methyl ester
- carbamic acid
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 239000000203 mixture Substances 0.000 title claims 2
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- 239000003909 protein kinase inhibitor Substances 0.000 title 1
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- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 abstract description 4
- 230000002074 deregulated effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- KKVYYGGCHJGEFJ-UHFFFAOYSA-N 1-n-(4-chlorophenyl)-6-methyl-5-n-[3-(7h-purin-6-yl)pyridin-2-yl]isoquinoline-1,5-diamine Chemical compound N=1C=CC2=C(NC=3C(=CC=CN=3)C=3C=4N=CNC=4N=CN=3)C(C)=CC=C2C=1NC1=CC=C(Cl)C=C1 KKVYYGGCHJGEFJ-UHFFFAOYSA-N 0.000 abstract 1
- 101100381978 Mus musculus Braf gene Proteins 0.000 abstract 1
- 230000004913 activation Effects 0.000 abstract 1
- CMJCXYNUCSMDBY-ZDUSSCGKSA-N lgx818 Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=C(Cl)C=2)F)=N1 CMJCXYNUCSMDBY-ZDUSSCGKSA-N 0.000 abstract 1
- LCWPXLBWVNEYIW-LBPRGKRZSA-N methyl n-[(2s)-1-[[4-[1-propan-2-yl-3-[2,4,5-trifluoro-3-(methanesulfonamido)phenyl]pyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C(F)=C(F)C=2)F)=N1 LCWPXLBWVNEYIW-LBPRGKRZSA-N 0.000 abstract 1
- SJTRSVMDXLVDFY-ZDUSSCGKSA-N methyl n-[(2s)-1-[[4-[3-[2,4-difluoro-3-(methanesulfonamido)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C(F)=CC=2)F)=N1 SJTRSVMDXLVDFY-ZDUSSCGKSA-N 0.000 abstract 1
- GTVBBDKLBUVTKF-HNNXBMFYSA-N methyl n-[(2s)-1-[[4-[3-[2,4-difluoro-3-(propylsulfonylamino)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound CCCS(=O)(=O)NC1=C(F)C=CC(C=2C(=CN(N=2)C(C)C)C=2N=C(NC[C@H](C)NC(=O)OC)N=CC=2)=C1F GTVBBDKLBUVTKF-HNNXBMFYSA-N 0.000 abstract 1
- APHFVSFDSHEMLK-ZDUSSCGKSA-N methyl n-[(2s)-1-[[4-[3-[2,5-dichloro-3-(methanesulfonamido)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=C(Cl)C=2)Cl)=N1 APHFVSFDSHEMLK-ZDUSSCGKSA-N 0.000 abstract 1
- IDDGSCPILQDMST-ZDUSSCGKSA-N methyl n-[(2s)-1-[[4-[3-[2,5-difluoro-3-(methanesulfonamido)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=C(F)C=2)F)=N1 IDDGSCPILQDMST-ZDUSSCGKSA-N 0.000 abstract 1
- BEPGTMTXHVYWRS-HNNXBMFYSA-N methyl n-[(2s)-1-[[4-[3-[2,6-difluoro-3-(propylsulfonylamino)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C=2C(=CN(N=2)C(C)C)C=2N=C(NC[C@H](C)NC(=O)OC)N=CC=2)=C1F BEPGTMTXHVYWRS-HNNXBMFYSA-N 0.000 abstract 1
- FIMRNHGGRIJTEX-ZDUSSCGKSA-N methyl n-[(2s)-1-[[4-[3-[2-chloro-3-(ethylsulfonylamino)-4,5-difluorophenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound CCS(=O)(=O)NC1=C(F)C(F)=CC(C=2C(=CN(N=2)C(C)C)C=2N=C(NC[C@H](C)NC(=O)OC)N=CC=2)=C1Cl FIMRNHGGRIJTEX-ZDUSSCGKSA-N 0.000 abstract 1
- YIEWFBJIVDMNJO-HNNXBMFYSA-N methyl n-[(2s)-1-[[4-[3-[2-chloro-3-(methanesulfonamido)-5-methylphenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=C(C)C=2)Cl)=N1 YIEWFBJIVDMNJO-HNNXBMFYSA-N 0.000 abstract 1
- ZKZGAMDUVHYNPH-ZDUSSCGKSA-N methyl n-[(2s)-1-[[4-[3-[2-chloro-5-fluoro-3-(methanesulfonamido)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=C(F)C=2)Cl)=N1 ZKZGAMDUVHYNPH-ZDUSSCGKSA-N 0.000 abstract 1
- FOKYULGGOAAGRF-HNNXBMFYSA-N methyl n-[(2s)-1-[[4-[3-[2-fluoro-3-(methanesulfonamido)-5-methylphenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=C(C)C=2)F)=N1 FOKYULGGOAAGRF-HNNXBMFYSA-N 0.000 abstract 1
- FCSQNBKYSFKSHZ-AWEZNQCLSA-N methyl n-[(2s)-1-[[4-[3-[2-fluoro-3-(methanesulfonamido)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=CC=2)F)=N1 FCSQNBKYSFKSHZ-AWEZNQCLSA-N 0.000 abstract 1
- RMHZWQZTKKHYCT-INIZCTEOSA-N methyl n-[(2s)-1-[[4-[3-[2-fluoro-3-(propylsulfonylamino)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound CCCS(=O)(=O)NC1=CC=CC(C=2C(=CN(N=2)C(C)C)C=2N=C(NC[C@H](C)NC(=O)OC)N=CC=2)=C1F RMHZWQZTKKHYCT-INIZCTEOSA-N 0.000 abstract 1
- JUTDCRUMEUQOPM-AWEZNQCLSA-N methyl n-[(2s)-1-[[4-[3-[3-(cyclopropylsulfonylamino)-2,5-difluorophenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(=O)(=O)C3CC3)C=C(F)C=2)F)=N1 JUTDCRUMEUQOPM-AWEZNQCLSA-N 0.000 abstract 1
- MFQUQRONWUFERA-HNNXBMFYSA-N methyl n-[(2s)-1-[[4-[3-[3-(methanesulfonamido)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C=C(NS(C)(=O)=O)C=CC=2)=N1 MFQUQRONWUFERA-HNNXBMFYSA-N 0.000 abstract 1
- OYJJSQKATCWOOM-ZDUSSCGKSA-N methyl n-[(2s)-1-[[4-[3-[3-chloro-2-(methanesulfonamido)pyridin-4-yl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)N=CC=2)Cl)=N1 OYJJSQKATCWOOM-ZDUSSCGKSA-N 0.000 abstract 1
- AZFXVYSHIJAZOU-AWEZNQCLSA-N methyl n-[(2s)-1-[[4-[3-[3-chloro-5-(methanesulfonamido)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C=C(NS(C)(=O)=O)C=C(Cl)C=2)=N1 AZFXVYSHIJAZOU-AWEZNQCLSA-N 0.000 abstract 1
- PCDHTILQESNIQQ-INIZCTEOSA-N methyl n-[(2s)-1-[[4-[3-[3-chloro-5-(propylsulfonylamino)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound CCCS(=O)(=O)NC1=CC(Cl)=CC(C=2C(=CN(N=2)C(C)C)C=2N=C(NC[C@H](C)NC(=O)OC)N=CC=2)=C1 PCDHTILQESNIQQ-INIZCTEOSA-N 0.000 abstract 1
- XVXYXUQCGWHPKG-LBPRGKRZSA-N methyl n-[(2s)-1-[[4-[3-[5-chloro-2-fluoro-3-(methanesulfonamido)phenyl]-1-ethylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound N=1N(CC)C=C(C=2N=C(NC[C@H](C)NC(=O)OC)N=CC=2)C=1C1=CC(Cl)=CC(NS(C)(=O)=O)=C1F XVXYXUQCGWHPKG-LBPRGKRZSA-N 0.000 abstract 1
- IFUNYGIIWVIYAY-HNNXBMFYSA-N methyl n-[(2s)-1-[[4-[3-[5-chloro-2-fluoro-3-(propylsulfonylamino)phenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound CCCS(=O)(=O)NC1=CC(Cl)=CC(C=2C(=CN(N=2)C(C)C)C=2N=C(NC[C@H](C)NC(=O)OC)N=CC=2)=C1F IFUNYGIIWVIYAY-HNNXBMFYSA-N 0.000 abstract 1
- GVJFWGLLYQAPCL-AWEZNQCLSA-N methyl n-[(2s)-1-[[4-[3-[5-chloro-3-(cyclopropylsulfonylamino)-2-fluorophenyl]-1-propan-2-ylpyrazol-4-yl]pyrimidin-2-yl]amino]propan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(=O)(=O)C3CC3)C=C(Cl)C=2)F)=N1 GVJFWGLLYQAPCL-AWEZNQCLSA-N 0.000 abstract 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 22
- 229940124530 sulfonamide Drugs 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- 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
-
- 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
- C07D401/14—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 three or more 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physiology (AREA)
- Nutrition Science (AREA)
- Hospice & Palliative Care (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Otolaryngology (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23807309P | 2009-08-28 | 2009-08-28 | |
| US31303910P | 2010-03-11 | 2010-03-11 | |
| PCT/US2010/046930 WO2011025927A1 (en) | 2009-08-28 | 2010-08-27 | Compounds and compositions as protein kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201200373A1 EA201200373A1 (ru) | 2012-09-28 |
| EA025222B1 true EA025222B1 (ru) | 2016-12-30 |
Family
ID=42782253
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201200373A EA025222B1 (ru) | 2009-08-28 | 2010-08-27 | Соединения и композиции в качестве ингибиторов протеинкиназ |
| EA201500175A EA201500175A1 (ru) | 2009-08-28 | 2010-08-27 | Соединения и композиции в качестве ингибиторов протеинкиназ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201500175A EA201500175A1 (ru) | 2009-08-28 | 2010-08-27 | Соединения и композиции в качестве ингибиторов протеинкиназ |
Country Status (49)
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| US8907270B2 (en) | 2010-06-30 | 2014-12-09 | Schlumberger Technology Corporation | Method and apparatus for gain regulation in a gamma detector |
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| US9408885B2 (en) | 2011-12-01 | 2016-08-09 | Vib Vzw | Combinations of therapeutic agents for treating melanoma |
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