EA039006B1 - Ингибиторы тирозинкиназы - Google Patents

Info

Publication number

EA039006B1

EA039006B1 EA201792529A EA201792529A EA039006B1 EA 039006 B1 EA039006 B1 EA 039006B1 EA 201792529 A EA201792529 A EA 201792529A EA 201792529 A EA201792529 A EA 201792529A EA 039006 B1 EA039006 B1 EA 039006B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

pharmaceutically acceptable

compound

acid

pyridin

Prior art date

2015-06-03

Links

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• Global Dossier
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• 229940121358 tyrosine kinase inhibitor Drugs 0.000 title abstract description 3
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 225
• 238000000034 method Methods 0.000 claims abstract description 44
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 241000124008 Mammalia Species 0.000 claims abstract description 10
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
• -1 piperidinyl carbon Chemical compound 0.000 claims description 302
• 150000003839 salts Chemical class 0.000 claims description 73
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 229920006395 saturated elastomer Polymers 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 239000011737 fluorine Chemical group 0.000 claims description 11
• 229910052731 fluorine Chemical group 0.000 claims description 11
• 125000006413 ring segment Chemical group 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 125000004476 heterocycloamino group Chemical group 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 150000001721 carbon Chemical group 0.000 claims description 7
• FPGGLMIYNLQOID-UHFFFAOYSA-N 3h-pyridin-2-one Chemical compound O=C1CC=CC=N1 FPGGLMIYNLQOID-UHFFFAOYSA-N 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
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• 229920001223 polyethylene glycol Polymers 0.000 description 19
• 238000003786 synthesis reaction Methods 0.000 description 19
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• 239000013543 active substance Substances 0.000 description 18
• 235000019439 ethyl acetate Nutrition 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• 239000003826 tablet Substances 0.000 description 18
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
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• 102000020233 phosphotransferase Human genes 0.000 description 17
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• 239000002904 solvent Substances 0.000 description 17
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• 239000002775 capsule Substances 0.000 description 16
• 150000001735 carboxylic acids Chemical class 0.000 description 16
• 125000000623 heterocyclic group Chemical group 0.000 description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
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• 238000006243 chemical reaction Methods 0.000 description 15
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
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