EA025496B1 - Ингибиторы тирозинкиназы - Google Patents

Info

Publication number

EA025496B1

EA025496B1 EA201391528A EA201391528A EA025496B1 EA 025496 B1 EA025496 B1 EA 025496B1 EA 201391528 A EA201391528 A EA 201391528A EA 201391528 A EA201391528 A EA 201391528A EA 025496 B1 EA025496 B1 EA 025496B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

pyrimidin

pyrazolo

carbonyl

methyl

Prior art date

2011-05-17

Links

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• 229940121358 tyrosine kinase inhibitor Drugs 0.000 title abstract description 9
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 224
• 150000003839 salts Chemical class 0.000 claims abstract description 67
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 54
• 201000010099 disease Diseases 0.000 claims abstract description 48
• 238000000034 method Methods 0.000 claims abstract description 37
• 239000003814 drug Substances 0.000 claims abstract description 33
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 21
• 201000011510 cancer Diseases 0.000 claims abstract description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 16
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 10
• 206010003246 arthritis Diseases 0.000 claims abstract description 8
• -1 alkyl fluorine Chemical compound 0.000 claims description 1496
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 292
• 125000000217 alkyl group Chemical group 0.000 claims description 174
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
• 239000001257 hydrogen Substances 0.000 claims description 75
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 239000000203 mixture Substances 0.000 claims description 73
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
• 125000004429 atom Chemical group 0.000 claims description 49
• 229910052736 halogen Inorganic materials 0.000 claims description 47
• 150000002367 halogens Chemical class 0.000 claims description 47
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 39
• 125000006376 (C3-C10) cycloalkyl group Chemical class 0.000 claims description 38
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 37
• 150000002431 hydrogen Chemical class 0.000 claims description 37
• 125000003545 alkoxy group Chemical group 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 125000005842 heteroatom Chemical group 0.000 claims description 34
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• 229920006395 saturated elastomer Polymers 0.000 claims description 29
• 125000001153 fluoro group Chemical group F* 0.000 claims description 28
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
• 125000004476 heterocycloamino group Chemical group 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 239000011737 fluorine Substances 0.000 claims description 23
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 229910052700 potassium Inorganic materials 0.000 claims description 23
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 19
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 125000002950 monocyclic group Chemical group 0.000 claims description 18
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
• 210000004027 cell Anatomy 0.000 claims description 15
• 238000006243 chemical reaction Methods 0.000 claims description 14
• 206010025323 Lymphomas Diseases 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 13
• 239000002246 antineoplastic agent Substances 0.000 claims description 13
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
• 201000004624 Dermatitis Diseases 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 12
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 201000003445 large cell neuroendocrine carcinoma Diseases 0.000 claims description 10
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 9
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
• 239000013256 coordination polymer Substances 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 7
• 125000001246 bromo group Chemical group Br* 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000002346 iodo group Chemical group I* 0.000 claims description 7
• 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 claims description 6
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 6
• 208000011691 Burkitt lymphomas Diseases 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 206010025135 lupus erythematosus Diseases 0.000 claims description 6
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 5
• 206010039710 Scleroderma Diseases 0.000 claims description 5
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 4
• 208000032568 B-cell prolymphocytic leukaemia Diseases 0.000 claims description 4
• 206010010741 Conjunctivitis Diseases 0.000 claims description 4
• 206010012442 Dermatitis contact Diseases 0.000 claims description 4
• 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 4
• 240000005926 Hamelia patens Species 0.000 claims description 4
• 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 206010052178 Lymphocytic lymphoma Diseases 0.000 claims description 4
• 206010036030 Polyarthritis Diseases 0.000 claims description 4
• 208000035416 Prolymphocytic B-Cell Leukemia Diseases 0.000 claims description 4
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
• 208000021386 Sjogren Syndrome Diseases 0.000 claims description 4
• 206010046851 Uveitis Diseases 0.000 claims description 4
• 208000010668 atopic eczema Diseases 0.000 claims description 4
• 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims description 4
• 230000001684 chronic effect Effects 0.000 claims description 4
• 206010009887 colitis Diseases 0.000 claims description 4
• 208000010247 contact dermatitis Diseases 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 201000003444 follicular lymphoma Diseases 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 206010028417 myasthenia gravis Diseases 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims description 3
• 208000023611 Burkitt leukaemia Diseases 0.000 claims description 3
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
• 239000005977 Ethylene Substances 0.000 claims description 3
• 208000017604 Hodgkin disease Diseases 0.000 claims description 3
• 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims description 3
• 206010065857 Primary Effusion Lymphoma Diseases 0.000 claims description 3
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 3
• 230000001093 anti-cancer Effects 0.000 claims description 3
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
• 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims description 3
• 239000012458 free base Substances 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 210000001541 thymus gland Anatomy 0.000 claims description 3
• GCTNTYCHYKCHEK-UHFFFAOYSA-N 4,4-dimethylpent-2-enenitrile Chemical compound CC(C)(C)C=CC#N GCTNTYCHYKCHEK-UHFFFAOYSA-N 0.000 claims description 2
• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical group C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
• RSNYYVBQGUMEKL-UHFFFAOYSA-N C(#N)C(C(=O)N)=CC(C)(C)C Chemical compound C(#N)C(C(=O)N)=CC(C)(C)C RSNYYVBQGUMEKL-UHFFFAOYSA-N 0.000 claims 3
• LTVSRKUELVZIGG-UHFFFAOYSA-N C(#N)C(C(=O)N)=CC(C)(C)N(C)C Chemical compound C(#N)C(C(=O)N)=CC(C)(C)N(C)C LTVSRKUELVZIGG-UHFFFAOYSA-N 0.000 claims 3
• SSRYCUAIDZWRAT-UHFFFAOYSA-N 2-cyano-3-cyclopropylprop-2-enamide Chemical compound NC(=O)C(C#N)=CC1CC1 SSRYCUAIDZWRAT-UHFFFAOYSA-N 0.000 claims 2
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims 2
• 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 2
• 208000002193 Pain Diseases 0.000 claims 2
• 230000003902 lesion Effects 0.000 claims 2
• 230000001185 psoriatic effect Effects 0.000 claims 2
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract description 8
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract description 8
• 230000005764 inhibitory process Effects 0.000 abstract description 4
• 230000008569 process Effects 0.000 abstract description 4
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 abstract 1
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 abstract 1
• 102100029981 Receptor tyrosine-protein kinase erbB-4 Human genes 0.000 abstract 1
• 101710100963 Receptor tyrosine-protein kinase erbB-4 Proteins 0.000 abstract 1
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 abstract 1
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 abstract 1
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 249
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 179
• 239000000243 solution Substances 0.000 description 143
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 140
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
• 239000007787 solid Substances 0.000 description 63
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
• 239000000741 silica gel Substances 0.000 description 50
• 229910002027 silica gel Inorganic materials 0.000 description 50
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 37
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
• BTCJGYMVVGSTDN-UHFFFAOYSA-N Spongistatin 7 Natural products C1C(=O)C(C)C(C2C)OCC2=CC(O2)CC(C)(O)CC2(O2)CC(O)CC2CC(=O)OC(C(C(CC(=C)CC(O)C=CC=C)O2)O)C(C)C2C(O)C(O2)(O)CC(O)C(C)C2CCCC=CC(O2)CC(O)CC22CC(OC)CC1O2 BTCJGYMVVGSTDN-UHFFFAOYSA-N 0.000 description 36
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 32
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
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• MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 26
• 239000012044 organic layer Substances 0.000 description 26
• 238000003756 stirring Methods 0.000 description 24
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 23
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• 229940079593 drug Drugs 0.000 description 21
• 125000003118 aryl group Chemical group 0.000 description 20
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• 125000001072 heteroaryl group Chemical group 0.000 description 17
• 150000002500 ions Chemical class 0.000 description 17
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 16
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 15
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• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 14
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• 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 description 14
• 239000004215 Carbon black (E152) Substances 0.000 description 12
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• 125000002947 alkylene group Chemical group 0.000 description 12
• JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 12
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• 125000003710 aryl alkyl group Chemical group 0.000 description 11
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 11
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• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 10
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• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
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• WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 description 6
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
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• 230000002401 inhibitory effect Effects 0.000 description 6
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