NZ532373A - Pyrimidine compound and medicinal composition thereof - Google Patents

Info

Publication number

NZ532373A

NZ532373A NZ532373A NZ53237302A NZ532373A NZ 532373 A NZ532373 A NZ 532373A NZ 532373 A NZ532373 A NZ 532373A NZ 53237302 A NZ53237302 A NZ 53237302A NZ 532373 A NZ532373 A NZ 532373A

Authority

NZ

New Zealand

Prior art keywords

group

substituted

carbon atoms

furyl

amino

Prior art date

2001-10-22

Links

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• Global Dossier
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• -1 Pyrimidine compound Chemical class 0.000 title description 352
• 239000000203 mixture Substances 0.000 title description 24
• 150000001875 compounds Chemical class 0.000 claims abstract description 338
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 126
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 84
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 52
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 52
• 206010010774 Constipation Diseases 0.000 claims abstract description 44
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 16
• 108010085277 Adenosine A2A receptor Proteins 0.000 claims abstract description 12
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
• 208000011231 Crohn disease Diseases 0.000 claims abstract description 7
• 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 7
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims abstract description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 467
• 238000004519 manufacturing process Methods 0.000 claims description 107
• 239000003795 chemical substances by application Substances 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
• 125000005843 halogen group Chemical group 0.000 claims description 43
• 239000012453 solvate Substances 0.000 claims description 42
• 239000003814 drug Substances 0.000 claims description 39
• 238000012360 testing method Methods 0.000 claims description 39
• 125000001424 substituent group Chemical group 0.000 claims description 35
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000003277 amino group Chemical group 0.000 claims description 24
• 201000010099 disease Diseases 0.000 claims description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 102000009346 Adenosine receptors Human genes 0.000 claims description 22
• 108050000203 Adenosine receptors Proteins 0.000 claims description 22
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 14
• 125000004434 sulfur atom Chemical group 0.000 claims description 14
• 125000002252 acyl group Chemical group 0.000 claims description 13
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 12
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 11
• 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 11
• 229960003878 haloperidol Drugs 0.000 claims description 11
• 208000008384 ileus Diseases 0.000 claims description 11
• 108010041368 Adenosine A2 Receptors Proteins 0.000 claims description 10
• 102000007471 Adenosine A2A receptor Human genes 0.000 claims description 10
• 102000000506 Adenosine A2 Receptors Human genes 0.000 claims description 9
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
• 125000005108 alkenylthio group Chemical group 0.000 claims description 9
• 125000005109 alkynylthio group Chemical group 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 208000009132 Catalepsy Diseases 0.000 claims description 8
• 206010047853 Waxy flexibility Diseases 0.000 claims description 8
• 125000001931 aliphatic group Chemical group 0.000 claims description 8
• 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 8
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
• 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 208000002249 Diabetes Complications Diseases 0.000 claims description 6
• 206010012655 Diabetic complications Diseases 0.000 claims description 6
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 6
• 229940122355 Insulin sensitizer Drugs 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 6
• 208000001132 Osteoporosis Diseases 0.000 claims description 6
• 239000002220 antihypertensive agent Substances 0.000 claims description 6
• 125000005251 aryl acyl group Chemical group 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 239000002934 diuretic Substances 0.000 claims description 6
• 125000005253 heteroarylacyl group Chemical group 0.000 claims description 6
• 229940126904 hypoglycaemic agent Drugs 0.000 claims description 6
• 235000020824 obesity Nutrition 0.000 claims description 6
• 102000007470 Adenosine A2B Receptor Human genes 0.000 claims description 5
• 108010085273 Adenosine A2B receptor Proteins 0.000 claims description 5
• 229940123702 Adenosine A2a receptor antagonist Drugs 0.000 claims description 5
• 206010010356 Congenital anomaly Diseases 0.000 claims description 5
• 239000002467 adenosine A2a receptor antagonist Substances 0.000 claims description 5
• 230000004064 dysfunction Effects 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 229940121359 adenosine receptor antagonist Drugs 0.000 claims description 3
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 3
• 125000005495 pyridazyl group Chemical group 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 229940124049 Adenosine A2 receptor antagonist Drugs 0.000 claims description 2
• 229940123053 Adenosine A2b receptor antagonist Drugs 0.000 claims description 2
• 239000003449 adenosine A2 receptor antagonist Substances 0.000 claims description 2
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims 2
• 101150078577 Adora2b gene Proteins 0.000 abstract description 18
• 150000003230 pyrimidines Chemical class 0.000 abstract description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 7
• 229940044551 receptor antagonist Drugs 0.000 abstract description 7
• 239000002464 receptor antagonist Substances 0.000 abstract description 7
• 229910052760 oxygen Inorganic materials 0.000 abstract description 2
• 229910052736 halogen Inorganic materials 0.000 abstract 1
• 150000002367 halogens Chemical class 0.000 abstract 1
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 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 154
• 238000006243 chemical reaction Methods 0.000 description 124
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 108
• 239000002904 solvent Substances 0.000 description 99
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 83
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 82
• 238000005160 1H NMR spectroscopy Methods 0.000 description 72
• 238000005481 NMR spectroscopy Methods 0.000 description 59
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• 239000002585 base Substances 0.000 description 55
• 239000007858 starting material Substances 0.000 description 55
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
• 239000000243 solution Substances 0.000 description 48
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
• 239000007787 solid Substances 0.000 description 40
• 229940093499 ethyl acetate Drugs 0.000 description 39
• 235000019439 ethyl acetate Nutrition 0.000 description 39
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 37
• 239000011541 reaction mixture Substances 0.000 description 36
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
• 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 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• 229910052783 alkali metal Inorganic materials 0.000 description 29
• 238000001914 filtration Methods 0.000 description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 26
• 102000005962 receptors Human genes 0.000 description 26
• 108020003175 receptors Proteins 0.000 description 26
• 238000003756 stirring Methods 0.000 description 25
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 150000002357 guanidines Chemical class 0.000 description 21
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
• 239000003153 chemical reaction reagent Substances 0.000 description 19
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• 238000001816 cooling Methods 0.000 description 17
• 238000000034 method Methods 0.000 description 17
• 229920006395 saturated elastomer Polymers 0.000 description 17
• 101150041968 CDC13 gene Proteins 0.000 description 16
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
• 235000019270 ammonium chloride Nutrition 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• 239000002126 C01EB10 - Adenosine Substances 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 229960005305 adenosine Drugs 0.000 description 15
• 230000027455 binding Effects 0.000 description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• 239000012298 atmosphere Substances 0.000 description 14
• 229910001873 dinitrogen Inorganic materials 0.000 description 14
• 239000000706 filtrate Substances 0.000 description 14
• 239000012046 mixed solvent Substances 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 239000002994 raw material Substances 0.000 description 14
• 150000001298 alcohols Chemical class 0.000 description 13
• 150000002170 ethers Chemical class 0.000 description 13
• 125000003373 pyrazinyl group Chemical group 0.000 description 13
• 125000002098 pyridazinyl group Chemical group 0.000 description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• 239000013078 crystal Substances 0.000 description 12
• 230000001590 oxidative effect Effects 0.000 description 12
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 12
• 230000005764 inhibitory process Effects 0.000 description 11
• 239000007800 oxidant agent Substances 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• PZNCKJDSGSPNMQ-UHFFFAOYSA-N 2-(2-fluoropyridin-4-yl)-1-(furan-2-yl)ethanone Chemical compound C1=NC(F)=CC(CC(=O)C=2OC=CC=2)=C1 PZNCKJDSGSPNMQ-UHFFFAOYSA-N 0.000 description 10
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 10
• 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 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 239000012267 brine Substances 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 239000011734 sodium Substances 0.000 description 10
• 229910052708 sodium Inorganic materials 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• RRLMPLDPCKRASL-UHFFFAOYSA-N 3-(dimethylamino)prop-2-enal Chemical class CN(C)C=CC=O RRLMPLDPCKRASL-UHFFFAOYSA-N 0.000 description 9
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 9
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
• 238000010438 heat treatment Methods 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 210000003141 lower extremity Anatomy 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• 229910000029 sodium carbonate Inorganic materials 0.000 description 9
• 239000012312 sodium hydride Substances 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• 210000001364 upper extremity Anatomy 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 8
• 150000008041 alkali metal carbonates Chemical class 0.000 description 8
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
• HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 8
• 239000000825 pharmaceutical preparation Substances 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 101150051188 Adora2a gene Proteins 0.000 description 7
• 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
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
• 230000009471 action Effects 0.000 description 7
• 150000001340 alkali metals Chemical class 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
• 125000006319 alkynyl amino group Chemical group 0.000 description 6
• 230000008485 antagonism Effects 0.000 description 6
• 238000009833 condensation Methods 0.000 description 6
• NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 6
• 238000002474 experimental method Methods 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 125000000842 isoxazolyl group Chemical group 0.000 description 6
• 125000002560 nitrile group Chemical group 0.000 description 6
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 6
• 125000000168 pyrrolyl group Chemical group 0.000 description 6
• 238000010898 silica gel chromatography Methods 0.000 description 6
• 239000011593 sulfur Substances 0.000 description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
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