JP5735526B2 - 三環式ピラゾールアミン誘導体 - Google Patents

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Publication number

JP5735526B2

JP5735526B2 JP2012538350A JP2012538350A JP5735526B2 JP 5735526 B2 JP5735526 B2 JP 5735526B2 JP 2012538350 A JP2012538350 A JP 2012538350A JP 2012538350 A JP2012538350 A JP 2012538350A JP 5735526 B2 JP5735526 B2 JP 5735526B2

Authority

JP

Japan

Prior art keywords

het

formula

nhso

pyrazole

compound

Prior art date

2009-11-13

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 491
• 238000000034 method Methods 0.000 claims description 222
• -1 U includes X 5 Chemical group 0.000 claims description 96
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 90
• 239000000203 mixture Substances 0.000 claims description 68
• 125000004432 carbon atom Chemical group C* 0.000 claims description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 49
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims description 48
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims description 48
• 238000006243 chemical reaction Methods 0.000 claims description 44
• 108091007960 PI3Ks Proteins 0.000 claims description 42
• 229910052727 yttrium Inorganic materials 0.000 claims description 39
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
• 150000003906 phosphoinositides Chemical class 0.000 claims description 28
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 27
• 239000004480 active ingredient Substances 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• 229920006395 saturated elastomer Polymers 0.000 claims description 24
• 239000003814 drug Substances 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 239000012453 solvate Substances 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 125000002619 bicyclic group Chemical group 0.000 claims description 15
• 229910052770 Uranium Inorganic materials 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 14
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• 229910052717 sulfur Inorganic materials 0.000 claims description 12
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• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 9
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• 239000003795 chemical substances by application Substances 0.000 claims description 7
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• 125000004429 atom Chemical group 0.000 claims description 4
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• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
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• 208000035475 disorder Diseases 0.000 claims description 4
• 208000026278 immune system disease Diseases 0.000 claims description 4
• 206010001935 American trypanosomiasis Diseases 0.000 claims description 3
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
• 208000024699 Chagas disease Diseases 0.000 claims description 3
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
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• 208000015023 Graves' disease Diseases 0.000 claims description 3
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• 208000010159 IgA glomerulonephritis Diseases 0.000 claims description 3
• 206010021263 IgA nephropathy Diseases 0.000 claims description 3
• 208000005615 Interstitial Cystitis Diseases 0.000 claims description 3
• 208000011200 Kawasaki disease Diseases 0.000 claims description 3
• 208000000185 Localized scleroderma Diseases 0.000 claims description 3
• 208000003250 Mixed connective tissue disease Diseases 0.000 claims description 3
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• 206010072148 Stiff-Person syndrome Diseases 0.000 claims description 3
• 241000223109 Trypanosoma cruzi Species 0.000 claims description 3
• 206010047115 Vasculitis Diseases 0.000 claims description 3
• 206010000269 abscess Diseases 0.000 claims description 3
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• 201000003631 narcolepsy Diseases 0.000 claims description 3
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• 201000000980 schizophrenia Diseases 0.000 claims description 3
• 210000000106 sweat gland Anatomy 0.000 claims description 3
• 206010043207 temporal arteritis Diseases 0.000 claims description 3
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• 206010072359 Neuromyotonia Diseases 0.000 claims description 2
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• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
• 208000006454 hepatitis Diseases 0.000 claims description 2
• 231100000283 hepatitis Toxicity 0.000 claims description 2
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
• 229940127557 pharmaceutical product Drugs 0.000 claims description 2
• 125000004122 cyclic group Chemical group 0.000 claims 1
• 239000000543 intermediate Substances 0.000 description 204
• 238000005481 NMR spectroscopy Methods 0.000 description 200
• 238000004949 mass spectrometry Methods 0.000 description 199
• 238000000132 electrospray ionisation Methods 0.000 description 194
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 180
• 238000004128 high performance liquid chromatography Methods 0.000 description 174
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 139
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 118
• 239000011541 reaction mixture Substances 0.000 description 105
• 239000007787 solid Substances 0.000 description 89
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 85
• 239000000243 solution Substances 0.000 description 81
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
• 239000002904 solvent Substances 0.000 description 77
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 76
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
• 235000019439 ethyl acetate Nutrition 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 58
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 52
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
• 239000012044 organic layer Substances 0.000 description 43
• 235000002639 sodium chloride Nutrition 0.000 description 42
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 42
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 41
• WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical group CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 39
• 230000002829 reductive effect Effects 0.000 description 39
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 37
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
• KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 33
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• 239000011734 sodium Substances 0.000 description 30
• 239000012299 nitrogen atmosphere Substances 0.000 description 29
• 239000002253 acid Substances 0.000 description 26
• 239000012267 brine Substances 0.000 description 25
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000002585 base Substances 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 21
• 238000004440 column chromatography Methods 0.000 description 19
• 150000002148 esters Chemical class 0.000 description 19
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• 229960000583 acetic acid Drugs 0.000 description 17
• CVQSWZMJOGOPAV-UHFFFAOYSA-N 2,3-dihydrothiochromen-4-one Chemical compound C1=CC=C2C(=O)CCSC2=C1 CVQSWZMJOGOPAV-UHFFFAOYSA-N 0.000 description 16
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
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• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 8
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