RU2318824C2 - Антагонисты рецептора аденозина a2b, фармацевтическая композиция на их основе и способ их получения - Google Patents

Info

Publication number

RU2318824C2

RU2318824C2 RU2004114210/04A RU2004114210A RU2318824C2 RU 2318824 C2 RU2318824 C2 RU 2318824C2 RU 2004114210/04 A RU2004114210/04 A RU 2004114210/04A RU 2004114210 A RU2004114210 A RU 2004114210A RU 2318824 C2 RU2318824 C2 RU 2318824C2

Authority

RU

Russia

Prior art keywords

dione

trihydropurin

formula

compound

phenyl

Prior art date

2001-11-09

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• 238000000034 method Methods 0.000 title claims abstract description 78
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
• 239000005557 antagonist Substances 0.000 title abstract description 8
• 102000007470 Adenosine A2B Receptor Human genes 0.000 title 1
• 108010085273 Adenosine A2B receptor Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 451
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims abstract description 58
• 239000002126 C01EB10 - Adenosine Substances 0.000 claims abstract description 29
• 229960005305 adenosine Drugs 0.000 claims abstract description 29
• 230000003042 antagnostic effect Effects 0.000 claims abstract 3
• 238000006243 chemical reaction Methods 0.000 claims description 102
• 229910052739 hydrogen Inorganic materials 0.000 claims description 84
• 239000001257 hydrogen Substances 0.000 claims description 83
• -1 3-trifluoromethylphenyl Chemical group 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 75
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
• 238000002360 preparation method Methods 0.000 claims description 42
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 38
• 150000002431 hydrogen Chemical class 0.000 claims description 36
• 229910052736 halogen Inorganic materials 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 125000002947 alkylene group Chemical group 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000005549 heteroarylene group Chemical group 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000000732 arylene group Chemical group 0.000 claims description 7
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
• 150000004866 oxadiazoles Chemical class 0.000 claims description 6
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 5
• JNJWKLSCJORTLT-UHFFFAOYSA-N 8-[4-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]phenyl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=C1)=CC=C1OCC(N=1)=NOC=1C1=CC=CC=C1OC JNJWKLSCJORTLT-UHFFFAOYSA-N 0.000 claims description 5
• LHMYROXNDKDUQN-UHFFFAOYSA-N 8-[4-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]phenyl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=C1)=CC=C1OCC(N=1)=NOC=1C1=CC=C(F)C=C1 LHMYROXNDKDUQN-UHFFFAOYSA-N 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 239000012458 free base Substances 0.000 claims description 5
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
• FJOWCRNUYDSBQY-UHFFFAOYSA-N 1,3-dipropyl-8-(1h-pyrazol-4-yl)-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C=1C=NNC=1 FJOWCRNUYDSBQY-UHFFFAOYSA-N 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• AHJHSANRNGKAFS-UHFFFAOYSA-N 8-[4-[[5-(3-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]phenyl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=C1)=CC=C1OCC(N=1)=NOC=1C1=CC=CC(OC)=C1 AHJHSANRNGKAFS-UHFFFAOYSA-N 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• VKTXMHRAIBKAOF-UHFFFAOYSA-N 1,3-dipropyl-8-[1-[2-[3-(trifluoromethyl)phenyl]ethyl]pyrazol-4-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(=C1)C=NN1CCC1=CC=CC(C(F)(F)F)=C1 VKTXMHRAIBKAOF-UHFFFAOYSA-N 0.000 claims description 3
• JBGRNTKBOQPADE-UHFFFAOYSA-N 1-butyl-8-[1-[(3-fluorophenyl)methyl]pyrazol-4-yl]-3,7-dihydropurine-2,6-dione Chemical compound N1C=2C(=O)N(CCCC)C(=O)NC=2N=C1C(=C1)C=NN1CC1=CC=CC(F)=C1 JBGRNTKBOQPADE-UHFFFAOYSA-N 0.000 claims description 3
• SEKFWEUZFWPIIW-UHFFFAOYSA-N 1-propyl-8-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrazol-4-yl]-3,7-dihydropurine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)NC=2N=C1C(=C1)C=NN1CC1=CC=CC(C(F)(F)F)=C1 SEKFWEUZFWPIIW-UHFFFAOYSA-N 0.000 claims description 3
• UDNGNWOKQLQPJV-UHFFFAOYSA-N 2-[4-[6-oxo-1-(2-oxopropyl)-3-propyl-2,7-dihydropurin-8-yl]-1H-pyrazol-5-yl]-2-phenylacetic acid Chemical group O=C(CN1CN(C=2N=C(NC=2C1=O)C=1C(=NNC=1)C(C(=O)O)C1=CC=CC=C1)CCC)C UDNGNWOKQLQPJV-UHFFFAOYSA-N 0.000 claims description 3
• FSZJGDMXEQVTPM-UHFFFAOYSA-N 3-butan-2-yl-1-methyl-8-(1h-pyrazol-4-yl)-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(C)C(=O)N(C(C)CC)C=2N=C1C=1C=NNC=1 FSZJGDMXEQVTPM-UHFFFAOYSA-N 0.000 claims description 3
• KOYXXLLNCXWUNF-UHFFFAOYSA-N 3-ethyl-1-propyl-8-[1-[[3-(trifluoromethyl)phenyl]methyl]pyrazol-4-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CC)C=2N=C1C(=C1)C=NN1CC1=CC=CC(C(F)(F)F)=C1 KOYXXLLNCXWUNF-UHFFFAOYSA-N 0.000 claims description 3
• VKONPLGZIZPWGJ-UHFFFAOYSA-N 4-[[4-(2,6-dioxo-1,3-dipropyl-7h-purin-8-yl)pyrazol-1-yl]methyl]benzoic acid Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(=C1)C=NN1CC1=CC=C(C(O)=O)C=C1 VKONPLGZIZPWGJ-UHFFFAOYSA-N 0.000 claims description 3
• KAYVCWBEIZTVCN-UHFFFAOYSA-N 8-(1-benzylpyrazol-4-yl)-1-propyl-3,7-dihydropurine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)NC=2N=C1C(=C1)C=NN1CC1=CC=CC=C1 KAYVCWBEIZTVCN-UHFFFAOYSA-N 0.000 claims description 3
• INMYJCHAOZGGBA-UHFFFAOYSA-N 8-[1-(2-phenylethyl)pyrazol-4-yl]-1-propyl-3,7-dihydropurine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)NC=2N=C1C(=C1)C=NN1CCC1=CC=CC=C1 INMYJCHAOZGGBA-UHFFFAOYSA-N 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
• IVDPFMFNQXHGNX-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=CC(F)=C1 IVDPFMFNQXHGNX-UHFFFAOYSA-N 0.000 claims 1
• 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 125000005490 tosylate group Chemical group 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
• 230000015572 biosynthetic process Effects 0.000 abstract description 10
• 238000003786 synthesis reaction Methods 0.000 abstract description 10
• 239000003814 drug Substances 0.000 abstract description 8
• 241000124008 Mammalia Species 0.000 abstract description 7
• 230000000694 effects Effects 0.000 abstract description 6
• 208000012902 Nervous system disease Diseases 0.000 abstract description 4
• 208000025966 Neurological disease Diseases 0.000 abstract description 4
• 208000024172 Cardiovascular disease Diseases 0.000 abstract description 3
• 230000001575 pathological effect Effects 0.000 abstract description 3
• 230000006907 apoptotic process Effects 0.000 abstract description 2
• 239000000126 substance Substances 0.000 abstract description 2
• 230000001079 digestive effect Effects 0.000 abstract 1
• 230000001900 immune effect Effects 0.000 abstract 1
• 230000007721 medicinal effect Effects 0.000 abstract 1
• 239000000203 mixture Substances 0.000 description 79
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
• 230000002829 reductive effect Effects 0.000 description 55
• 125000001072 heteroaryl group Chemical group 0.000 description 51
• 239000002904 solvent Substances 0.000 description 51
• 125000003118 aryl group Chemical group 0.000 description 48
• 125000001424 substituent group Chemical group 0.000 description 46
• 125000003277 amino group Chemical group 0.000 description 42
• 239000000243 solution Substances 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
• 239000000047 product Substances 0.000 description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• 239000004480 active ingredient Substances 0.000 description 27
• 150000002367 halogens Chemical group 0.000 description 25
• 102000005962 receptors Human genes 0.000 description 24
• 108020003175 receptors Proteins 0.000 description 24
• 125000000623 heterocyclic group Chemical group 0.000 description 23
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 22
• 125000004181 carboxyalkyl group Chemical group 0.000 description 22
• 125000004093 cyano group Chemical group *C#N 0.000 description 22
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• 229920002554 vinyl polymer Polymers 0.000 description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 21
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 21
• 235000019439 ethyl acetate Nutrition 0.000 description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• 125000003342 alkenyl group Chemical group 0.000 description 19
• 239000004615 ingredient Substances 0.000 description 19
• 239000007787 solid Substances 0.000 description 19
• 239000003826 tablet Substances 0.000 description 19
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
• 125000000392 cycloalkenyl group Chemical group 0.000 description 17
• 239000011541 reaction mixture Substances 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• 239000002585 base Substances 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• 150000001412 amines Chemical class 0.000 description 13
• FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 13
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
• 125000000547 substituted alkyl group Chemical group 0.000 description 13
• 125000004104 aryloxy group Chemical group 0.000 description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
• 238000001914 filtration Methods 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 239000007864 aqueous solution Substances 0.000 description 10
• 208000006673 asthma Diseases 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 239000012442 inert solvent Substances 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 125000002252 acyl group Chemical group 0.000 description 9
• 125000004442 acylamino group Chemical group 0.000 description 9
• 125000004423 acyloxy group Chemical group 0.000 description 9
• 125000005110 aryl thio group Chemical group 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 description 9
• 125000000468 ketone group Chemical group 0.000 description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
• 229910052760 oxygen Inorganic materials 0.000 description 9
• 239000001301 oxygen Substances 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 230000004044 response Effects 0.000 description 9
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 8
• 125000004414 alkyl thio group Chemical group 0.000 description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 8
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
• 238000010586 diagram Methods 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 150000003573 thiols Chemical group 0.000 description 8
• 239000005711 Benzoic acid Substances 0.000 description 7
• 125000000033 alkoxyamino group Chemical group 0.000 description 7
• 125000006598 aminocarbonylamino group Chemical group 0.000 description 7
• 235000010233 benzoic acid Nutrition 0.000 description 7
• 125000001246 bromo group Chemical group Br* 0.000 description 7
• 125000001309 chloro group Chemical group Cl* 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 210000003630 histaminocyte Anatomy 0.000 description 7
• 125000002346 iodo group Chemical group I* 0.000 description 7
• 239000010410 layer Substances 0.000 description 7
• 125000005017 substituted alkenyl group Chemical group 0.000 description 7
• KGDOHXYALMXHLF-UHFFFAOYSA-N 1-benzylpyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=CC=C1 KGDOHXYALMXHLF-UHFFFAOYSA-N 0.000 description 6
• GZLZRPNUDBIQBM-UHFFFAOYSA-N 6-amino-1-methylpyrimidine-2,4-dione Chemical compound CN1C(N)=CC(=O)NC1=O GZLZRPNUDBIQBM-UHFFFAOYSA-N 0.000 description 6
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 6
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• 229920002472 Starch Polymers 0.000 description 6
• 230000027455 binding Effects 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 150000004820 halides Chemical class 0.000 description 6
• 125000005368 heteroarylthio group Chemical group 0.000 description 6
• 125000004468 heterocyclylthio group Chemical group 0.000 description 6
• 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 6
• 235000019359 magnesium stearate Nutrition 0.000 description 6
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 6
• 239000008108 microcrystalline cellulose Substances 0.000 description 6
• 229940016286 microcrystalline cellulose Drugs 0.000 description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
• 239000002798 polar solvent Substances 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• 235000019698 starch Nutrition 0.000 description 6
• 125000003107 substituted aryl group Chemical group 0.000 description 6
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
• CADWRZPSQGRYRW-UHFFFAOYSA-N 5,6-diamino-1-benzylpyrimidine-2,4-dione Chemical compound NC1=C(N)C(=O)NC(=O)N1CC1=CC=CC=C1 CADWRZPSQGRYRW-UHFFFAOYSA-N 0.000 description 5
• USWCRMBFRFQYQI-UHFFFAOYSA-N 5,6-diamino-3-butyl-1h-pyrimidine-2,4-dione Chemical compound CCCCN1C(=O)NC(N)=C(N)C1=O USWCRMBFRFQYQI-UHFFFAOYSA-N 0.000 description 5
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