TWI330183B - - Google Patents

Info

Publication number

TWI330183B

TWI330183B TW091124227A TW91124227A TWI330183B TW I330183 B TWI330183 B TW I330183B TW 091124227 A TW091124227 A TW 091124227A TW 91124227 A TW91124227 A TW 91124227A TW I330183 B TWI330183 B TW I330183B

Authority

TW

Taiwan

Prior art keywords

group

substituent

compound

substituted

amino

Prior art date

2001-10-22

Links

• Espacenet
• Global Dossier
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• 125000001424 substituent group Chemical group 0.000 claims abstract description 579
• 150000001875 compounds Chemical class 0.000 claims abstract description 226
• 150000003839 salts Chemical class 0.000 claims abstract description 95
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 81
• 239000012453 solvate Substances 0.000 claims abstract description 66
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 60
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 41
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 37
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 36
• 125000004429 atom Chemical group 0.000 claims abstract description 34
• 125000005843 halogen group Chemical group 0.000 claims abstract description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 24
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 22
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 18
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 15
• 230000003042 antagnostic effect Effects 0.000 claims abstract description 6
• 239000002904 solvent Substances 0.000 claims description 74
• 238000004519 manufacturing process Methods 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 63
• 125000003118 aryl group Chemical group 0.000 claims description 60
• OIRDTQYFTABQOQ-KQYNXXCUSA-N Adenosine Natural products 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 description 52
• 102000005962 receptors Human genes 0.000 claims description 46
• 108020003175 receptors Proteins 0.000 claims description 46
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 42
• 206010010774 Constipation Diseases 0.000 claims description 41
• 150000002576 ketones Chemical class 0.000 claims description 40
• 239000000203 mixture Substances 0.000 claims description 38
• 239000003795 chemical substances by application Substances 0.000 claims description 33
• 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 28
• 229960005305 adenosine Drugs 0.000 claims description 28
• 238000012360 testing method Methods 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 27
• 239000007789 gas Substances 0.000 claims description 26
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• 125000003277 amino group Chemical group 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• 238000011282 treatment Methods 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 239000010949 copper Substances 0.000 claims description 14
• 208000018737 Parkinson disease Diseases 0.000 claims description 13
• 230000001737 promoting effect Effects 0.000 claims description 12
• 230000013872 defecation Effects 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 7
• 102000007471 Adenosine A2A receptor Human genes 0.000 claims description 6
• 108010085277 Adenosine A2A receptor Proteins 0.000 claims description 6
• 102000007470 Adenosine A2B Receptor Human genes 0.000 claims description 6
• 108010085273 Adenosine A2B receptor Proteins 0.000 claims description 6
• 125000001931 aliphatic group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000005109 alkynylthio group Chemical group 0.000 claims description 6
• 208000003243 intestinal obstruction Diseases 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 229930024421 Adenine Natural products 0.000 claims description 5
• 206010010356 Congenital anomaly Diseases 0.000 claims description 5
• 229960000643 adenine Drugs 0.000 claims description 5
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 210000002216 heart Anatomy 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
• GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 4
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 229910052802 copper Inorganic materials 0.000 claims description 4
• 230000001079 digestive effect Effects 0.000 claims description 4
• 230000004064 dysfunction Effects 0.000 claims description 4
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 3
• 125000005577 anthracene group Chemical group 0.000 claims description 3
• 238000004090 dissolution Methods 0.000 claims description 3
• 230000002496 gastric effect Effects 0.000 claims description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
• 239000002689 soil Substances 0.000 claims description 3
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 238000001356 surgical procedure Methods 0.000 claims description 2
• 238000000338 in vitro Methods 0.000 claims 6
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 3
• QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims 2
• BZRIWDPKOVQWII-UHFFFAOYSA-N 1-methyl-1H-acridin-2-one Chemical compound CC1C(C=CC2=NC3=CC=CC=C3C=C12)=O BZRIWDPKOVQWII-UHFFFAOYSA-N 0.000 claims 1
• UWDHESVDMJZCAI-UHFFFAOYSA-N 2-pyridin-2-yl-4h-pyridin-3-one Chemical compound O=C1CC=CN=C1C1=CC=CC=N1 UWDHESVDMJZCAI-UHFFFAOYSA-N 0.000 claims 1
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• QONUMVWLFMVXOC-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methoxyethyl)pyridin-2-one Chemical compound C1=CC(=O)N(CCOC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 QONUMVWLFMVXOC-UHFFFAOYSA-N 0.000 claims 1
• JGNIOSOZBWBDNF-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-methylbutyl)pyridin-2-one Chemical compound C1=CC(=O)N(CC(C)CC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 JGNIOSOZBWBDNF-UHFFFAOYSA-N 0.000 claims 1
• HVWYNEQNUCTRPO-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-octylpyridin-2-one Chemical compound C1=CC(=O)N(CCCCCCCC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 HVWYNEQNUCTRPO-UHFFFAOYSA-N 0.000 claims 1
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 1
• 201000009030 Carcinoma Diseases 0.000 claims 1
• PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims 1
• 125000002228 disulfide group Chemical group 0.000 claims 1
• 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 claims 1
• UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 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
• -1 pyrimidine compound Chemical class 0.000 abstract description 320
• 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 133
• 102000009346 Adenosine receptors Human genes 0.000 abstract description 15
• 108050000203 Adenosine receptors Proteins 0.000 abstract description 15
• 101150078577 Adora2b gene Proteins 0.000 abstract description 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract description 5
• 125000002252 acyl group Chemical group 0.000 abstract 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 196
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 145
• 238000006243 chemical reaction Methods 0.000 description 135
• 239000002585 base Substances 0.000 description 122
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
• 230000015572 biosynthetic process Effects 0.000 description 63
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 62
• 238000003786 synthesis reaction Methods 0.000 description 62
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• 235000019439 ethyl acetate Nutrition 0.000 description 58
• 239000007858 starting material Substances 0.000 description 58
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 46
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
• 239000002253 acid Substances 0.000 description 42
• 239000000243 solution Substances 0.000 description 40
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
• 150000001412 amines Chemical class 0.000 description 31
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000007864 aqueous solution Substances 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 23
• 239000003153 chemical reaction reagent Substances 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• 101150041968 CDC13 gene Proteins 0.000 description 19
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
• 229910052783 alkali metal Inorganic materials 0.000 description 19
• 230000027455 binding Effects 0.000 description 19
• 239000011541 reaction mixture Substances 0.000 description 19
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 18
• 201000010099 disease Diseases 0.000 description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 17
• 239000007787 solid Substances 0.000 description 17
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
• 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 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 229940079593 drug Drugs 0.000 description 15
• 150000002429 hydrazines Chemical class 0.000 description 15
• 239000001257 hydrogen Substances 0.000 description 15
• 229910052739 hydrogen Inorganic materials 0.000 description 15
• 125000000714 pyrimidinyl group Chemical group 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• 229910052708 sodium Inorganic materials 0.000 description 15
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 14
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 14
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
• 239000013078 crystal Substances 0.000 description 13
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 13
• 239000012046 mixed solvent Substances 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• 230000001225 therapeutic effect Effects 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• MWKFXSUHUHTGQN-UHFFFAOYSA-N n-decyl alcohol Natural products CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
• 229940044551 receptor antagonist Drugs 0.000 description 11
• 239000002464 receptor antagonist Substances 0.000 description 11
• 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• 150000001454 anthracenes Chemical class 0.000 description 10
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
• 229910052751 metal Inorganic materials 0.000 description 10
• 239000002184 metal Substances 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• 150000003230 pyrimidines Chemical class 0.000 description 10
• 239000002994 raw material Substances 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 150000002431 hydrogen Chemical class 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 229920000609 methyl cellulose Polymers 0.000 description 9
• 235000010981 methylcellulose Nutrition 0.000 description 9
• 239000001923 methylcellulose Substances 0.000 description 9
• 239000007800 oxidant agent Substances 0.000 description 9
• 230000000069 prophylactic effect Effects 0.000 description 9
• ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 9
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 9
• 239000012312 sodium hydride Substances 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• 238000006467 substitution reaction Methods 0.000 description 9
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 9
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 8
• 241000220317 Rosa Species 0.000 description 8
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 8
• 150000008041 alkali metal carbonates Chemical class 0.000 description 8
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 8
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 8
• 235000011130 ammonium sulphate Nutrition 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 150000002430 hydrocarbons Chemical class 0.000 description 8
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 8
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
• 210000003141 lower extremity Anatomy 0.000 description 8
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
• 239000012299 nitrogen atmosphere Substances 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
• JADDQZYHOWSFJD-FLNNQWSLSA-N N-ethyl-5'-carboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 JADDQZYHOWSFJD-FLNNQWSLSA-N 0.000 description 7
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 7
• 235000019270 ammonium chloride Nutrition 0.000 description 7
• 239000012267 brine Substances 0.000 description 7
• 150000001721 carbon Chemical group 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 206010012601 diabetes mellitus Diseases 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 229960005181 morphine Drugs 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 230000003449 preventive effect Effects 0.000 description 7
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 7
• 229910000029 sodium carbonate Inorganic materials 0.000 description 7
• 229940124597 therapeutic agent Drugs 0.000 description 7
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