TWI772295B - 經醯胺-取代的吡啶基三唑衍生物及其用途 - Google Patents

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Publication number

TWI772295B

TWI772295B TW106114432A TW106114432A TWI772295B TW I772295 B TWI772295 B TW I772295B TW 106114432 A TW106114432 A TW 106114432A TW 106114432 A TW106114432 A TW 106114432A TW I772295 B TWI772295 B TW I772295B

Authority

TW

Taiwan

Prior art keywords

compounds

compound

general formula

methyl

acid

Prior art date

2016-05-03

Links

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• PRQUBDQDCAULSW-UHFFFAOYSA-N 2-(2h-triazol-4-yl)pyridine Chemical class N1N=NC(C=2N=CC=CC=2)=C1 PRQUBDQDCAULSW-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 323
• 238000000034 method Methods 0.000 claims abstract description 98
• 238000011282 treatment Methods 0.000 claims abstract description 52
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• 238000002360 preparation method Methods 0.000 claims abstract description 16
• 230000008569 process Effects 0.000 claims abstract description 11
• 230000006806 disease prevention Effects 0.000 claims abstract description 9
• -1 trifluoromethoxy, ethoxycarbonyl Chemical group 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 52
• 239000002904 solvent Substances 0.000 claims description 32
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 25
• 208000017169 kidney disease Diseases 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 239000005557 antagonist Substances 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 16
• 230000001154 acute effect Effects 0.000 claims description 15
• 229940079593 drug Drugs 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 14
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 14
• 150000004677 hydrates Chemical class 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 229940044551 receptor antagonist Drugs 0.000 claims description 11
• 239000002464 receptor antagonist Substances 0.000 claims description 11
• 208000005171 Dysmenorrhea Diseases 0.000 claims description 9
• 206010013935 Dysmenorrhoea Diseases 0.000 claims description 9
• 239000003472 antidiabetic agent Substances 0.000 claims description 9
• 208000020832 chronic kidney disease Diseases 0.000 claims description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 229940124597 therapeutic agent Drugs 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• 239000005541 ACE inhibitor Substances 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• 206010007558 Cardiac failure chronic Diseases 0.000 claims description 7
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 7
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• 208000003782 Raynaud disease Diseases 0.000 claims description 5
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• 229910021529 ammonia Inorganic materials 0.000 claims description 5
• 229940125708 antidiabetic agent Drugs 0.000 claims description 5
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
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• 208000024891 symptom Diseases 0.000 claims description 5
• QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 4
• 229940082615 organic nitrates used in cardiac disease Drugs 0.000 claims description 4
• 229910019142 PO4 Inorganic materials 0.000 claims description 3
• 229930003316 Vitamin D Natural products 0.000 claims description 3
• 239000011230 binding agent Substances 0.000 claims description 3
• 239000003018 immunosuppressive agent Substances 0.000 claims description 3
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
• 239000010452 phosphate Substances 0.000 claims description 3
• 235000019166 vitamin D Nutrition 0.000 claims description 3
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• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
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• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
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• 239000000047 product Substances 0.000 description 56
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 52
• KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 48
• 102000005962 receptors Human genes 0.000 description 47
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 42
• 210000004027 cell Anatomy 0.000 description 41
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 36
• 102000004136 Vasopressin Receptors Human genes 0.000 description 35
• 108090000643 Vasopressin Receptors Proteins 0.000 description 35
• 238000012360 testing method Methods 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
• 201000010099 disease Diseases 0.000 description 33
• 239000007787 solid Substances 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• 239000003112 inhibitor Substances 0.000 description 32
• GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 31
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• 238000005481 NMR spectroscopy Methods 0.000 description 30
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 30
• 239000012043 crude product Substances 0.000 description 29
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
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• 238000002953 preparative HPLC Methods 0.000 description 24
• 239000002585 base Substances 0.000 description 23
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 22
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• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
• 235000011114 ammonium hydroxide Nutrition 0.000 description 20
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
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