NO326410B1 - Glukopyranosyloksypyrazolderivater samt medikamentell anvendelse derav - Google Patents

Info

Publication number

NO326410B1

NO326410B1 NO20032909A NO20032909A NO326410B1 NO 326410 B1 NO326410 B1 NO 326410B1 NO 20032909 A NO20032909 A NO 20032909A NO 20032909 A NO20032909 A NO 20032909A NO 326410 B1 NO326410 B1 NO 326410B1

Authority

NO

Norway

Prior art keywords

group

methyl

glucopyranosyloxy

isopropyl

methylpyrazole

Prior art date

2000-12-28

Links

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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 230
• -1 4-isopropoxyphenyl Chemical group 0.000 claims description 228
• 125000000217 alkyl group Chemical group 0.000 claims description 55
• 125000002252 acyl group Chemical group 0.000 claims description 54
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 43
• 239000000203 mixture Substances 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 32
• 239000003112 inhibitor Substances 0.000 claims description 31
• 239000003814 drug Substances 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
• 229940079593 drug Drugs 0.000 claims description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 206010012601 diabetes mellitus Diseases 0.000 claims description 24
• 208000002249 Diabetes Complications Diseases 0.000 claims description 23
• 206010012655 Diabetic complications Diseases 0.000 claims description 23
• 101000716682 Homo sapiens Sodium/glucose cotransporter 2 Proteins 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 22
• 102000052543 human SLC5A2 Human genes 0.000 claims description 22
• 238000002360 preparation method Methods 0.000 claims description 20
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 19
• 201000010099 disease Diseases 0.000 claims description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 208000018914 glucose metabolism disease Diseases 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 208000008589 Obesity Diseases 0.000 claims description 14
• 235000020824 obesity Nutrition 0.000 claims description 14
• 201000001421 hyperglycemia Diseases 0.000 claims description 13
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 11
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 11
• 206010020772 Hypertension Diseases 0.000 claims description 11
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 11
• 201000008980 hyperinsulinism Diseases 0.000 claims description 11
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 10
• 201000001320 Atherosclerosis Diseases 0.000 claims description 9
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 206010030113 Oedema Diseases 0.000 claims description 7
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 6
• 206010019280 Heart failures Diseases 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 5
• 125000005042 acyloxymethyl group Chemical group 0.000 claims description 5
• 201000005569 Gout Diseases 0.000 claims description 4
• 201000001431 Hyperuricemia Diseases 0.000 claims description 4
• 238000009472 formulation Methods 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
• ZRCWPRKBUCTYIR-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]-5-methyl-3-propyl-1H-pyrazole Chemical compound CCCc1n[nH]c(C)c1Cc1ccc(OC)cc1 ZRCWPRKBUCTYIR-UHFFFAOYSA-N 0.000 claims 1
• FFQIEJXRBROSBT-VZWAGXQNSA-N [(2r,3s,4s,5r,6s)-6-[4-[(4-ethylphenyl)methyl]-5-methyl-1-propan-2-ylpyrazol-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl methyl carbonate Chemical compound C1=CC(CC)=CC=C1CC1=C(C)N(C(C)C)N=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(=O)OC)O1 FFQIEJXRBROSBT-VZWAGXQNSA-N 0.000 claims 1
• UAGOLMGFVKMQMQ-AREVGRJGSA-N ethyl [(2r,3s,4s,5r,6s)-6-[4-[(4-ethylphenyl)methyl]-5-methyl-1-propan-2-ylpyrazol-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl carbonate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)OCC)O[C@H]1OC1=NN(C(C)C)C(C)=C1CC1=CC=C(CC)C=C1 UAGOLMGFVKMQMQ-AREVGRJGSA-N 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 136
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 94
• 238000005160 1H NMR spectroscopy Methods 0.000 description 91
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
• 239000002904 solvent Substances 0.000 description 55
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
• 238000006243 chemical reaction Methods 0.000 description 47
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
• 239000000243 solution Substances 0.000 description 44
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 36
• 239000008103 glucose Substances 0.000 description 35
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 34
• 238000000034 method Methods 0.000 description 26
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
• 239000000556 agonist Substances 0.000 description 23
• 239000007858 starting material Substances 0.000 description 22
• 238000012360 testing method Methods 0.000 description 22
• 239000012442 inert solvent Substances 0.000 description 21
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
• 239000003480 eluent Substances 0.000 description 20
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 20
• 230000002829 reductive effect Effects 0.000 description 20
• 238000010992 reflux Methods 0.000 description 20
• 229940002612 prodrug Drugs 0.000 description 19
• 239000000651 prodrug Substances 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 17
• 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 17
• 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 17
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
• 230000035484 reaction time Effects 0.000 description 17
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• 239000000872 buffer Substances 0.000 description 15
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
• 230000002401 inhibitory effect Effects 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
• 230000008569 process Effects 0.000 description 15
• 238000004440 column chromatography Methods 0.000 description 14
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 13
• 239000008280 blood Substances 0.000 description 13
• 210000004369 blood Anatomy 0.000 description 13
• 239000012046 mixed solvent Substances 0.000 description 13
• BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 12
• 101150041968 CDC13 gene Proteins 0.000 description 12
• 206010022489 Insulin Resistance Diseases 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 230000009102 absorption Effects 0.000 description 12
• 238000010521 absorption reaction Methods 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• ZNJLQCPPAZECMW-UHFFFAOYSA-N (4-propan-2-yloxyphenyl)methanol Chemical compound CC(C)OC1=CC=C(CO)C=C1 ZNJLQCPPAZECMW-UHFFFAOYSA-N 0.000 description 10
• 229940123208 Biguanide Drugs 0.000 description 10
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• 102000004877 Insulin Human genes 0.000 description 10
• 108090001061 Insulin Proteins 0.000 description 10
• 241000700159 Rattus Species 0.000 description 10
• 229940125396 insulin Drugs 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 9
• 230000003914 insulin secretion Effects 0.000 description 9
• 210000002700 urine Anatomy 0.000 description 9
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 8
• 108020004414 DNA Proteins 0.000 description 8
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 8
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 8
• 230000002440 hepatic effect Effects 0.000 description 8
• PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• 230000002485 urinary effect Effects 0.000 description 8
• 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 7
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
• 102100040918 Pro-glucagon Human genes 0.000 description 7
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 7
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
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• 238000001914 filtration Methods 0.000 description 7
• 210000003734 kidney Anatomy 0.000 description 7
• 238000005259 measurement Methods 0.000 description 7
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 7
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 7
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 7
• PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 6
• CYAKWEQUWJAHLW-UHFFFAOYSA-N 1-(chloromethyl)-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(CCl)C=C1 CYAKWEQUWJAHLW-UHFFFAOYSA-N 0.000 description 6
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 6
• 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 229940122904 Glucagon receptor antagonist Drugs 0.000 description 6
• 229940121931 Gluconeogenesis inhibitor Drugs 0.000 description 6
• 102000003638 Glucose-6-Phosphatase Human genes 0.000 description 6
• 108010086800 Glucose-6-Phosphatase Proteins 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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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 6
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
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• 239000002830 appetite depressant Substances 0.000 description 6
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• 238000002414 normal-phase solid-phase extraction Methods 0.000 description 6
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• JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 6
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• 125000001424 substituent group Chemical group 0.000 description 6
• 238000005406 washing Methods 0.000 description 6
• ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 description 5
• SXKBTDJJEQQEGE-UHFFFAOYSA-N 3-(3,5-dibromo-4-hydroxy-benzoyl)-2-ethyl-benzofuran-6-sulfonic acid [4-(thiazol-2-ylsulfamoyl)-phenyl]-amide Chemical compound CCC=1OC2=CC(S(=O)(=O)NC=3C=CC(=CC=3)S(=O)(=O)NC=3SC=CN=3)=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 SXKBTDJJEQQEGE-UHFFFAOYSA-N 0.000 description 5
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 5
• 239000005541 ACE inhibitor Substances 0.000 description 5
• 108010005094 Advanced Glycation End Products Proteins 0.000 description 5
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• WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 5
• 229940122907 Phosphatase inhibitor Drugs 0.000 description 5
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