EA019156B1 - Производные оксима в качестве ингибиторов hsp90 - Google Patents

Info

Publication number

EA019156B1

EA019156B1 EA201070912A EA201070912A EA019156B1 EA 019156 B1 EA019156 B1 EA 019156B1 EA 201070912 A EA201070912 A EA 201070912A EA 201070912 A EA201070912 A EA 201070912A EA 019156 B1 EA019156 B1 EA 019156B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

amino

compound

phenyl

fluoro

Prior art date

2008-02-01

Links

• Espacenet
• Global Dossier
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• 239000003481 heat shock protein 90 inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 341
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
• 239000001257 hydrogen Substances 0.000 claims abstract description 36
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 21
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• -1 4-fluoro-2- (6-methoxypyridin-2-yl) phenyl Chemical group 0.000 claims description 376
• 239000000203 mixture Substances 0.000 claims description 170
• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims description 90
• 150000002923 oximes Chemical class 0.000 claims description 75
• 206010028980 Neoplasm Diseases 0.000 claims description 71
• 150000003839 salts Chemical class 0.000 claims description 54
• 238000011282 treatment Methods 0.000 claims description 37
• 201000011510 cancer Diseases 0.000 claims description 33
• 239000003814 drug Substances 0.000 claims description 25
• 230000005764 inhibitory process Effects 0.000 claims description 10
• 206010061218 Inflammation Diseases 0.000 claims description 9
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 9
• 230000004054 inflammatory process Effects 0.000 claims description 9
• 206010003246 arthritis Diseases 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• NTNPLXUDFWURMK-UHFFFAOYSA-N OCCCCON=C1C=NC=NC1 Chemical compound OCCCCON=C1C=NC=NC1 NTNPLXUDFWURMK-UHFFFAOYSA-N 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 229940124531 pharmaceutical excipient Drugs 0.000 claims description 4
• 206010052779 Transplant rejections Diseases 0.000 claims description 3
• 238000000034 method Methods 0.000 abstract description 143
• 101710113864 Heat shock protein 90 Proteins 0.000 abstract description 95
• 230000002401 inhibitory effect Effects 0.000 abstract description 14
• 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 abstract 1
• 239000011541 reaction mixture Substances 0.000 description 163
• 238000001819 mass spectrum Methods 0.000 description 125
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
• 239000000243 solution Substances 0.000 description 101
• 238000005481 NMR spectroscopy Methods 0.000 description 100
• 239000007787 solid Substances 0.000 description 97
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
• 238000006243 chemical reaction Methods 0.000 description 75
• 239000003921 oil Substances 0.000 description 73
• 235000019198 oils Nutrition 0.000 description 71
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• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 59
• 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 58
• 235000002639 sodium chloride Nutrition 0.000 description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 55
• 238000005160 1H NMR spectroscopy Methods 0.000 description 52
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• 238000002347 injection Methods 0.000 description 21
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• 239000000126 substance Substances 0.000 description 21
• SUJRGEXVDOJLIR-GZZLJNBRSA-N (5e)-7-[4-fluoro-2-(2-fluoropyridin-3-yl)phenyl]-4-methyl-5-phenoxyimino-7,8-dihydro-6h-quinazolin-2-amine Chemical compound C1=2C(C)=NC(N)=NC=2CC(C=2C(=CC(F)=CC=2)C=2C(=NC=CC=2)F)C\C1=N/OC1=CC=CC=C1 SUJRGEXVDOJLIR-GZZLJNBRSA-N 0.000 description 20
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
• 239000002552 dosage form Substances 0.000 description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• 239000002585 base Substances 0.000 description 17
• 239000000843 powder Substances 0.000 description 17
• JDEUUKYNTHHAQH-UHFFFAOYSA-N 2,2-dimethylbutanamide Chemical compound CCC(C)(C)C(N)=O JDEUUKYNTHHAQH-UHFFFAOYSA-N 0.000 description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
• 230000033115 angiogenesis Effects 0.000 description 15
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
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