NO329692B1 - Forbindelser som er A2B-adenosinreseptorantagonister, fremgangsmate for fremstilling av slike, farmasoytisk preparat omfattende forbindelsene og anvendelse av forbindelsene - Google Patents

Info

Publication number

NO329692B1

NO329692B1 NO20042378A NO20042378A NO329692B1 NO 329692 B1 NO329692 B1 NO 329692B1 NO 20042378 A NO20042378 A NO 20042378A NO 20042378 A NO20042378 A NO 20042378A NO 329692 B1 NO329692 B1 NO 329692B1

Authority

NO

Norway

Prior art keywords

dione

formula

trihydropurine

compound

phenyl

Prior art date

2001-11-09

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 435
• 238000000034 method Methods 0.000 claims abstract description 74
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 208000006673 asthma Diseases 0.000 claims abstract description 13
• 229940121359 adenosine receptor antagonist Drugs 0.000 claims abstract description 10
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims abstract description 10
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 6
• 230000033115 angiogenesis Effects 0.000 claims abstract description 5
• 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 5
• 238000006243 chemical reaction Methods 0.000 claims description 88
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 239000001257 hydrogen Substances 0.000 claims description 74
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
• -1 3-trifluoromethylphenyl Chemical group 0.000 claims description 64
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 51
• 150000002431 hydrogen Chemical class 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
• 229910052736 halogen Inorganic materials 0.000 claims description 35
• 150000002367 halogens Chemical class 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 101150078577 Adora2b gene Proteins 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 13
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 12
• 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 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
• 239000012458 free base Substances 0.000 claims description 7
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 206010012735 Diarrhoea Diseases 0.000 claims description 5
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 150000004866 oxadiazoles Chemical class 0.000 claims description 5
• 125000001715 oxadiazolyl group Chemical group 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
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 230000008569 process Effects 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
• QSEYHOMIGYEFFY-UHFFFAOYSA-N 1-butyl-8-[1-[[5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl]pyrazol-4-yl]-3,7-dihydropurine-2,6-dione Chemical compound N1C=2C(=O)N(CCCC)C(=O)NC=2N=C1C(=C1)C=NN1CC(N=1)=NOC=1C1=CC=C(Cl)C=C1 QSEYHOMIGYEFFY-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 compound 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
• 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
• HWHLLTUJISZFDN-UHFFFAOYSA-N 8-[1-[[5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl]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=NN1CC(N=1)=NOC=1C1=CC=C(Cl)C=C1 HWHLLTUJISZFDN-UHFFFAOYSA-N 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 208000018737 Parkinson disease Diseases 0.000 claims description 2
• 206010039966 Senile dementia Diseases 0.000 claims description 2
• 150000001721 carbon Chemical group 0.000 claims 4
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
• 125000004191 (C1-C6) alkoxy group Chemical group 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
• 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 1
• 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 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
• 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims 1
• 125000003226 pyrazolyl group Chemical group 0.000 claims 1
• 125000005490 tosylate group Chemical class 0.000 claims 1
• 208000035475 disorder Diseases 0.000 abstract description 4
• 208000025966 Neurological disease Diseases 0.000 abstract description 3
• 208000024172 Cardiovascular disease Diseases 0.000 abstract description 2
• 230000002757 inflammatory effect Effects 0.000 abstract 1
• 238000002360 preparation method Methods 0.000 description 139
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• 239000000203 mixture Substances 0.000 description 66
• 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 53
• 239000002904 solvent Substances 0.000 description 51
• 125000003118 aryl group Chemical group 0.000 description 48
• 125000001424 substituent group Chemical group 0.000 description 45
• 239000000243 solution Substances 0.000 description 41
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
• 239000000047 product Substances 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• 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 description 26
• 125000003545 alkoxy group Chemical group 0.000 description 25
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 25
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 24
• 125000004181 carboxyalkyl group Chemical group 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
• 235000019439 ethyl acetate Nutrition 0.000 description 21
• 125000004432 carbon atom Chemical group C* 0.000 description 20
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• 125000003342 alkenyl group Chemical group 0.000 description 19
• 125000000623 heterocyclic group Chemical group 0.000 description 19
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 239000004480 active ingredient Substances 0.000 description 17
• 125000000753 cycloalkyl group Chemical group 0.000 description 17
• 239000007787 solid Substances 0.000 description 17
• 125000000304 alkynyl group Chemical group 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• 239000003826 tablet Substances 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 125000000392 cycloalkenyl group Chemical group 0.000 description 15
• 239000002585 base Substances 0.000 description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
• 239000002126 C01EB10 - Adenosine Substances 0.000 description 13
• 229960005305 adenosine Drugs 0.000 description 13
• 150000001412 amines Chemical class 0.000 description 13
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
• FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• 125000004414 alkyl thio group Chemical group 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
• 239000012442 inert solvent Substances 0.000 description 10
• 239000004615 ingredient Substances 0.000 description 10
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound 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
• 229930194542 Keto Natural products 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
• 125000004104 aryloxy group Chemical group 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 238000004587 chromatography analysis Methods 0.000 description 9
• 230000000694 effects Effects 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
• 229910052757 nitrogen Inorganic materials 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
• 125000000547 substituted alkyl group Chemical group 0.000 description 9
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
• 150000003573 thiols Chemical class 0.000 description 9
• 230000007306 turnover Effects 0.000 description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
• 125000000033 alkoxyamino group Chemical group 0.000 description 8
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 8
• 125000006598 aminocarbonylamino 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
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 229910052794 bromium Inorganic materials 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 125000005368 heteroarylthio group Chemical group 0.000 description 8
• 125000004470 heterocyclooxy group Chemical group 0.000 description 8
• 125000004468 heterocyclylthio group Chemical group 0.000 description 8
• 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 8
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 239000005711 Benzoic acid Substances 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 210000003630 histaminocyte Anatomy 0.000 description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• 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
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
• 239000007864 aqueous solution Substances 0.000 description 6
• 238000003556 assay Methods 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
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 239000002798 polar solvent Substances 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 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
• 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 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
• WDVYWEYJVBNHLX-UHFFFAOYSA-N 6-amino-1-benzyl-5-nitrosopyrimidine-2,4-dione Chemical compound NC1=C(N=O)C(=O)NC(=O)N1CC1=CC=CC=C1 WDVYWEYJVBNHLX-UHFFFAOYSA-N 0.000 description 5
• QMKJOZVQZBJSEC-UHFFFAOYSA-N 6-amino-1-benzylpyrimidine-2,4-dione Chemical compound NC1=CC(=O)NC(=O)N1CC1=CC=CC=C1 QMKJOZVQZBJSEC-UHFFFAOYSA-N 0.000 description 5
• XBMQWAVBSYNIQO-UHFFFAOYSA-N 6-amino-3-butyl-1h-pyrimidine-2,4-dione Chemical compound CCCCN1C(=O)C=C(N)NC1=O XBMQWAVBSYNIQO-UHFFFAOYSA-N 0.000 description 5
• AFXRGDZUPUNBCX-UHFFFAOYSA-N 6-amino-3-butyl-5-nitroso-1h-pyrimidine-2,4-dione Chemical compound CCCCN1C(=O)NC(N)=C(N=O)C1=O AFXRGDZUPUNBCX-UHFFFAOYSA-N 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
• 239000007983 Tris buffer Substances 0.000 description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 5
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 5
• 235000011130 ammonium sulphate Nutrition 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 230000004071 biological effect Effects 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 150000002430 hydrocarbons Chemical group 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 239000006187 pill Substances 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
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