EA018163B1 - Имидазопиридазинкарбонитрилы, используемые в качестве ингибиторов киназы - Google Patents

Info

Publication number

EA018163B1

EA018163B1 EA201100580A EA201100580A EA018163B1 EA 018163 B1 EA018163 B1 EA 018163B1 EA 201100580 A EA201100580 A EA 201100580A EA 201100580 A EA201100580 A EA 201100580A EA 018163 B1 EA018163 B1 EA 018163B1

Authority

EA

Eurasian Patent Office

Prior art keywords

substituted

alkyl

cases

substituents

independently selected

Prior art date

2008-10-09

Links

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• 229940043355 kinase inhibitor Drugs 0.000 title description 5
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 246
• 150000003839 salts Chemical class 0.000 claims abstract description 37
• -1 substituted 0-5 K e Chemical group 0.000 claims description 240
• 125000000217 alkyl group Chemical group 0.000 claims description 213
• 125000001424 substituent group Chemical group 0.000 claims description 204
• 229910052739 hydrogen Inorganic materials 0.000 claims description 172
• 125000000623 heterocyclic group Chemical group 0.000 claims description 103
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
• 229910052799 carbon Inorganic materials 0.000 claims description 90
• 238000000034 method Methods 0.000 claims description 70
• 229910052757 nitrogen Inorganic materials 0.000 claims description 57
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
• 125000004432 carbon atom Chemical group C* 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 31
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
• 206010028980 Neoplasm Diseases 0.000 claims description 21
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 20
• 229910052700 potassium Inorganic materials 0.000 claims description 20
• 229910052794 bromium Inorganic materials 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 125000002950 monocyclic group Chemical group 0.000 claims description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• 201000010099 disease Diseases 0.000 claims description 13
• 125000002619 bicyclic group Chemical group 0.000 claims description 12
• 201000011510 cancer Diseases 0.000 claims description 11
• 229910052698 phosphorus Inorganic materials 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
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• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
• 230000033115 angiogenesis Effects 0.000 claims description 2
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
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• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
• 125000006168 tricyclic group Chemical group 0.000 claims description 2
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
• 206010001167 Adenocarcinoma of colon Diseases 0.000 claims 1
• 208000036832 Adenocarcinoma of ovary Diseases 0.000 claims 1
• 235000009470 Theobroma cacao Nutrition 0.000 claims 1
• 201000008274 breast adenocarcinoma Diseases 0.000 claims 1
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• 102000001253 Protein Kinase Human genes 0.000 abstract description 20
• 108060006633 protein kinase Proteins 0.000 abstract description 20
• 230000000694 effects Effects 0.000 abstract description 12
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• 150000005233 imidazopyridazines Chemical class 0.000 abstract description 5
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 608
• 239000000243 solution Substances 0.000 description 276
• 239000000543 intermediate Substances 0.000 description 267
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 200
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 198
• 238000004128 high performance liquid chromatography Methods 0.000 description 145
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 134
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• 239000000203 mixture Substances 0.000 description 118
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• 238000002360 preparation method Methods 0.000 description 87
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• 229910001868 water Inorganic materials 0.000 description 76
• PJESVVYWPFAJCS-UHFFFAOYSA-N pyridazine-3-carbonitrile Chemical compound N#CC1=CC=CN=N1 PJESVVYWPFAJCS-UHFFFAOYSA-N 0.000 description 72
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 68
• 239000000725 suspension Substances 0.000 description 59
• 239000002904 solvent Substances 0.000 description 55
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
• 238000001514 detection method Methods 0.000 description 42
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• 239000000706 filtrate Substances 0.000 description 39
• 229940002612 prodrug Drugs 0.000 description 36
• 239000000651 prodrug Substances 0.000 description 36
• 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 description 36
• YLXWTAXPOOYRSL-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1=CC=NN2C(C#N)=CN=C21 YLXWTAXPOOYRSL-UHFFFAOYSA-N 0.000 description 35
• 238000001914 filtration Methods 0.000 description 34
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 30
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 24
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 239000007795 chemical reaction product Substances 0.000 description 24
• 239000000741 silica gel Substances 0.000 description 24
• 229910002027 silica gel Inorganic materials 0.000 description 24
• 239000012453 solvate Substances 0.000 description 24
• 238000003818 flash chromatography Methods 0.000 description 23
• 239000012298 atmosphere Substances 0.000 description 22
• 238000010828 elution Methods 0.000 description 22
• 239000003814 drug Substances 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 20
• 239000003112 inhibitor Substances 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
• 239000007864 aqueous solution Substances 0.000 description 19
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 19
• 239000012267 brine Substances 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 17
• 239000003054 catalyst Substances 0.000 description 17
• 235000019198 oils Nutrition 0.000 description 17
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
• 241001660687 Xantho Species 0.000 description 16
• 229910052786 argon Inorganic materials 0.000 description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• 235000011007 phosphoric acid Nutrition 0.000 description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 15
• 229910000024 caesium carbonate Inorganic materials 0.000 description 15
• 239000012044 organic layer Substances 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 14
• 229940079593 drug Drugs 0.000 description 14
• 229910052745 lead Inorganic materials 0.000 description 14
• 238000004007 reversed phase HPLC Methods 0.000 description 14
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 13
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
• 239000003153 chemical reaction reagent Substances 0.000 description 13
• 239000013256 coordination polymer Substances 0.000 description 13
• 150000004677 hydrates Chemical class 0.000 description 13
• 239000010410 layer Substances 0.000 description 13
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• 125000004076 pyridyl group Chemical group 0.000 description 13
• 108010054404 Adenylyl-sulfate kinase Proteins 0.000 description 12
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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• 102100027662 Sphingosine kinase 2 Human genes 0.000 description 11
• 229910052796 boron Inorganic materials 0.000 description 11
• 238000002955 isolation Methods 0.000 description 11
• 125000000842 isoxazolyl group Chemical group 0.000 description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
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• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
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• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 7
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• 239000000047 product Substances 0.000 description 7
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• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 7
• 238000000926 separation method Methods 0.000 description 7
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
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• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• 108091000080 Phosphotransferase Proteins 0.000 description 6
• 125000004429 atom Chemical group 0.000 description 6
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 6
• 230000004663 cell proliferation Effects 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 6
• 125000001624 naphthyl group Chemical group 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
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• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 6
• STADGSMPDAECAH-UHFFFAOYSA-N 4-(2-fluoro-5-nitrophenyl)-1,2,4-triazole Chemical compound [O-][N+](=O)C1=CC=C(F)C(N2C=NN=C2)=C1 STADGSMPDAECAH-UHFFFAOYSA-N 0.000 description 5
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• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
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• 125000001113 thiadiazolyl group Chemical group 0.000 description 5
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