JP4462930B2 - ピリミジン化合物及びその医薬組成物 - Google Patents
ピリミジン化合物及びその医薬組成物 Download PDFInfo
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- JP4462930B2 JP4462930B2 JP2003538155A JP2003538155A JP4462930B2 JP 4462930 B2 JP4462930 B2 JP 4462930B2 JP 2003538155 A JP2003538155 A JP 2003538155A JP 2003538155 A JP2003538155 A JP 2003538155A JP 4462930 B2 JP4462930 B2 JP 4462930B2
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- substituent
- furyl
- optionally substituted
- amino
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- -1 Pyrimidine compound Chemical class 0.000 title abstract description 420
- 125000001424 substituent group Chemical group 0.000 claims abstract description 470
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 162
- 150000003839 salts Chemical class 0.000 claims abstract description 69
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 60
- 239000012453 solvate Substances 0.000 claims abstract description 57
- 125000005843 halogen group Chemical group 0.000 claims abstract description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 32
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 26
- 125000002252 acyl group Chemical group 0.000 claims abstract description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 11
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 8
- 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 description 104
- 238000004519 manufacturing process Methods 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 58
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 55
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 52
- 229960005305 adenosine Drugs 0.000 claims description 52
- 206010010774 Constipation Diseases 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 20
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 229940044551 receptor antagonist Drugs 0.000 claims description 16
- 239000002464 receptor antagonist Substances 0.000 claims description 16
- 229940124597 therapeutic agent Drugs 0.000 claims description 16
- 208000018737 Parkinson disease Diseases 0.000 claims description 14
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 13
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 12
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 12
- 230000013872 defecation Effects 0.000 claims description 11
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 11
- 230000003449 preventive effect Effects 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000005108 alkenylthio group Chemical group 0.000 claims description 10
- 125000005109 alkynylthio group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 9
- 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000005251 aryl acyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000005253 heteroarylacyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 206010021333 Ileus paralytic Diseases 0.000 claims description 6
- 201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 claims description 6
- 201000007620 paralytic ileus Diseases 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 206010010356 Congenital anomaly Diseases 0.000 claims description 5
- 230000007160 gastrointestinal dysfunction Effects 0.000 claims description 5
- 230000000968 intestinal effect Effects 0.000 claims description 5
- 208000003243 intestinal obstruction Diseases 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 4
- 210000003736 gastrointestinal content Anatomy 0.000 claims description 4
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- WJNNXYLGOHCGCH-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-fluoroethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCF)C=1 WJNNXYLGOHCGCH-UHFFFAOYSA-N 0.000 claims description 3
- KLQQNDZPIWTDSO-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CN=C(N)N=C1C1=CC=CO1 KLQQNDZPIWTDSO-UHFFFAOYSA-N 0.000 claims description 3
- 229940121359 adenosine receptor antagonist Drugs 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- LXMGWNGPIIDYEZ-UHFFFAOYSA-N 5-(2-amino-4-phenylpyrimidin-5-yl)-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CN=C(N)N=C1C1=CC=CC=C1 LXMGWNGPIIDYEZ-UHFFFAOYSA-N 0.000 claims description 2
- KXDNYLRDVSRARZ-UHFFFAOYSA-N 5-(2-amino-4-thiophen-2-ylpyrimidin-5-yl)-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CN=C(N)N=C1C1=CC=CS1 KXDNYLRDVSRARZ-UHFFFAOYSA-N 0.000 claims description 2
- LWPWANLSNUFFAH-UHFFFAOYSA-N 5-[2,4-diamino-6-(3-fluorophenyl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=C(N)N=C(N)N=C1C1=CC=CC(F)=C1 LWPWANLSNUFFAH-UHFFFAOYSA-N 0.000 claims description 2
- CTYOLHLKCVSGEG-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=C(C=2OC=CC=2)N=C(N)N=C1C1=CC=CO1 CTYOLHLKCVSGEG-UHFFFAOYSA-N 0.000 claims description 2
- GIIUUEOCDDLBQZ-UHFFFAOYSA-N 5-[2-amino-4-(3-fluorophenyl)pyrimidin-5-yl]-1-methylpyridin-2-one Chemical compound C1=CC(=O)N(C)C=C1C1=CN=C(N)N=C1C1=CC=CC(F)=C1 GIIUUEOCDDLBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- RWOLMPQKNXRXFP-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-ethylpyridin-2-one Chemical compound C1=CC(=O)N(CC)C=C1C1=CN=C(N)N=C1C1=CC=CO1 RWOLMPQKNXRXFP-UHFFFAOYSA-N 0.000 claims description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000005412 pyrazyl group Chemical group 0.000 claims description 2
- 125000005495 pyridazyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229940124382 agent for constipation Drugs 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 85
- 125000003342 alkenyl group Chemical group 0.000 abstract description 56
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 40
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 37
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 29
- 108050000203 Adenosine receptors Proteins 0.000 abstract description 19
- 102000009346 Adenosine receptors Human genes 0.000 abstract description 19
- 125000004434 sulfur atom Chemical group 0.000 abstract description 16
- 125000004429 atom Chemical group 0.000 abstract description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 12
- 125000000304 alkynyl group Chemical group 0.000 abstract description 11
- 230000003042 antagnostic effect Effects 0.000 abstract description 5
- 101150078577 Adora2b gene Proteins 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 139
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 109
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 91
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
- 230000015572 biosynthetic process Effects 0.000 description 78
- 238000003786 synthesis reaction Methods 0.000 description 78
- 239000002904 solvent Substances 0.000 description 70
- 239000000243 solution Substances 0.000 description 64
- 102000005962 receptors Human genes 0.000 description 63
- 108020003175 receptors Proteins 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 239000007858 starting material Substances 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000002585 base Substances 0.000 description 44
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 42
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 41
- 239000007787 solid Substances 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- 229910052739 hydrogen Inorganic materials 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 238000012360 testing method Methods 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- 238000001914 filtration Methods 0.000 description 31
- 229910052783 alkali metal Inorganic materials 0.000 description 29
- 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
- 229920006395 saturated elastomer Polymers 0.000 description 26
- 230000027455 binding Effects 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000003153 chemical reaction reagent Substances 0.000 description 22
- 150000002357 guanidines Chemical class 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 20
- 235000019270 ammonium chloride Nutrition 0.000 description 20
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
- 238000011282 treatment Methods 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
- 150000002926 oxygen Chemical class 0.000 description 17
- 201000010099 disease Diseases 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 16
- 150000003230 pyrimidines Chemical class 0.000 description 16
- 239000002994 raw material Substances 0.000 description 16
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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
- 125000003373 pyrazinyl group Chemical group 0.000 description 14
- 125000002098 pyridazinyl group Chemical group 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000725 suspension Substances 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
- 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 description 12
- 150000002829 nitrogen Chemical group 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 230000001225 therapeutic effect Effects 0.000 description 11
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 10
- 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- 239000007800 oxidant agent Substances 0.000 description 10
- 230000008569 process Effects 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 class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 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
- 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
- 0 *c(c(*)nc(*)n1)c1[Al]* Chemical compound *c(c(*)nc(*)n1)c1[Al]* 0.000 description 8
- RRLMPLDPCKRASL-UHFFFAOYSA-N 3-(dimethylamino)prop-2-enal Chemical class CN(C)C=CC=O RRLMPLDPCKRASL-UHFFFAOYSA-N 0.000 description 8
- 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 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- 150000001298 alcohols Chemical class 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
- 229910052799 carbon Inorganic materials 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 8
- ACFHETZZSOOPTG-UHFFFAOYSA-N 5-[2-amino-4,6-bis(furan-2-yl)pyrimidin-5-yl]-1h-pyridin-2-one Chemical compound C1=CC(=O)NC=C1C=1C(C=2OC=CC=2)=NC(N)=NC=1C1=CC=CO1 ACFHETZZSOOPTG-UHFFFAOYSA-N 0.000 description 7
- 208000009132 Catalepsy Diseases 0.000 description 7
- 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 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
- 206010047853 Waxy flexibility Diseases 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 229920000609 methyl cellulose Polymers 0.000 description 7
- 235000010981 methylcellulose Nutrition 0.000 description 7
- 239000001923 methylcellulose Substances 0.000 description 7
- 125000000168 pyrrolyl group Chemical group 0.000 description 7
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Classifications
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Obesity (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
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- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001324018 | 2001-10-22 | ||
| JP2001324018 | 2001-10-22 | ||
| PCT/JP2002/010952 WO2003035639A1 (en) | 2001-10-22 | 2002-10-22 | Pyrimidine compound and medicinal composition thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO2003035639A1 JPWO2003035639A1 (ja) | 2005-02-10 |
| JP4462930B2 true JP4462930B2 (ja) | 2010-05-12 |
Family
ID=19140824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003538155A Expired - Fee Related JP4462930B2 (ja) | 2001-10-22 | 2002-10-22 | ピリミジン化合物及びその医薬組成物 |
Country Status (24)
| Country | Link |
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| US (2) | US7396836B2 (OSRAM) |
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| TW (1) | TWI330183B (OSRAM) |
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