PL215572B1 - Zwiazek pirymidynowy lub jego sól, kompozycja farmaceutyczna, zawierajace taki zwiazek, jej zastosowanie jako srodka do leczenia lub zapobiegania chorobom oraz zastosowanie zwiazku do wytwarzania srodka - Google Patents

Info

Publication number

PL215572B1

PL215572B1 PL370274A PL37027402A PL215572B1 PL 215572 B1 PL215572 B1 PL 215572B1 PL 370274 A PL370274 A PL 370274A PL 37027402 A PL37027402 A PL 37027402A PL 215572 B1 PL215572 B1 PL 215572B1

Authority

PL

Poland

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 claims abstract description 98
• 239000000203 mixture Substances 0.000 title claims description 74
• 150000001875 compounds Chemical class 0.000 claims abstract description 291
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 244
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 73
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
• 150000003839 salts Chemical class 0.000 claims abstract description 47
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 43
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 38
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 38
• 125000005843 halogen group Chemical group 0.000 claims abstract description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 71
• 238000004519 manufacturing process Methods 0.000 claims description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 33
• 208000018737 Parkinson disease Diseases 0.000 claims description 15
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 208000011231 Crohn disease Diseases 0.000 claims description 8
• 208000002249 Diabetes Complications Diseases 0.000 claims description 8
• 206010012655 Diabetic complications Diseases 0.000 claims description 8
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 8
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 8
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 8
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
• 208000008589 Obesity Diseases 0.000 claims description 8
• 208000001132 Osteoporosis Diseases 0.000 claims description 8
• 239000000935 antidepressant agent Substances 0.000 claims description 8
• 229940005513 antidepressants Drugs 0.000 claims description 8
• 239000003472 antidiabetic agent Substances 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 230000013872 defecation Effects 0.000 claims description 8
• 239000002934 diuretic Substances 0.000 claims description 8
• 229940126904 hypoglycaemic agent Drugs 0.000 claims description 8
• 235000020824 obesity Nutrition 0.000 claims description 8
• 230000001430 anti-depressive effect Effects 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 206010021333 Ileus paralytic Diseases 0.000 claims description 6
• 201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 201000007620 paralytic ileus Diseases 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 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 5
• 206010010356 Congenital anomaly Diseases 0.000 claims description 5
• 229940122355 Insulin sensitizer Drugs 0.000 claims description 5
• 230000001882 diuretic effect Effects 0.000 claims description 5
• 230000007160 gastrointestinal dysfunction Effects 0.000 claims description 5
• 208000003243 intestinal obstruction Diseases 0.000 claims description 5
• 206010010774 Constipation Diseases 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 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 3
• 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 3
• 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 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
• 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 3
• INNCIQWLGZENAG-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-(2-pyrrol-1-ylethyl)pyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=C1)C=CC(=O)N1CCN1C=CC=C1 INNCIQWLGZENAG-UHFFFAOYSA-N 0.000 claims description 3
• LFOIYKKLYCWEDX-UHFFFAOYSA-N 5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-1-benzylpyridin-2-one Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C(=C1)C=CC(=O)N1CC1=CC=CC=C1 LFOIYKKLYCWEDX-UHFFFAOYSA-N 0.000 claims description 3
• 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 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
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 239000002220 antihypertensive agent Substances 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 230000002496 gastric effect Effects 0.000 claims description 3
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 3
• 125000005412 pyrazyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• LDTQCLGREAWLQH-UHFFFAOYSA-N 3-[5-[2-amino-4-(furan-2-yl)pyrimidin-5-yl]-2-oxopyridin-1-yl]propanenitrile Chemical compound C=1C=COC=1C1=NC(N)=NC=C1C=1C=CC(=O)N(CCC#N)C=1 LDTQCLGREAWLQH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
• 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
• 239000004480 active ingredient Substances 0.000 claims description 2
• 238000001356 surgical procedure Methods 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 24
• 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 22
• 102000009346 Adenosine receptors Human genes 0.000 abstract description 19
• 108050000203 Adenosine receptors Proteins 0.000 abstract description 19
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 19
• 101150078577 Adora2b gene Proteins 0.000 abstract description 17
• 229910052717 sulfur Inorganic materials 0.000 abstract description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 13
• 125000004093 cyano group Chemical group *C#N 0.000 abstract description 12
• 125000004430 oxygen atom Chemical group O* 0.000 abstract description 12
• 125000004434 sulfur atom Chemical group 0.000 abstract description 10
• 125000002252 acyl group Chemical group 0.000 abstract description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 6
• 239000012453 solvate Substances 0.000 abstract description 2
• 230000003042 antagnostic effect Effects 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 214
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
• 238000006243 chemical reaction Methods 0.000 description 111
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 100
• 239000002904 solvent Substances 0.000 description 96
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 80
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
• 239000000243 solution Substances 0.000 description 57
• 239000007858 starting material Substances 0.000 description 57
• 239000002585 base Substances 0.000 description 54
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
• 238000012360 testing method Methods 0.000 description 38
• 239000011541 reaction mixture Substances 0.000 description 35
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
• 239000007787 solid Substances 0.000 description 34
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 229910052783 alkali metal Inorganic materials 0.000 description 29
• 150000002357 guanidines Chemical class 0.000 description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
• 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 25
• 238000002360 preparation method Methods 0.000 description 24
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 23
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 150000002430 hydrocarbons Chemical group 0.000 description 21
• 235000019270 ammonium chloride Nutrition 0.000 description 20
• 239000003153 chemical reaction reagent Substances 0.000 description 20
• 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 20
• 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
• 125000003118 aryl group Chemical group 0.000 description 18
• 238000000034 method Methods 0.000 description 18
• 239000000725 suspension Substances 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
• 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 16
• 230000027455 binding Effects 0.000 description 16
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 14
• 229910052736 halogen Inorganic materials 0.000 description 14
• 150000002367 halogens Chemical class 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
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• 108010085277 Adenosine A2A receptor Proteins 0.000 description 13
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• 230000005764 inhibitory process Effects 0.000 description 13
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• 238000003756 stirring Methods 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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• 239000002253 acid Substances 0.000 description 12
• 150000001298 alcohols Chemical class 0.000 description 12
• 239000013078 crystal Substances 0.000 description 12
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
• 102000005962 receptors Human genes 0.000 description 12
• 108020003175 receptors Proteins 0.000 description 12
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 11
• 102000007471 Adenosine A2A receptor Human genes 0.000 description 11
• 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 11
• 239000007800 oxidant agent Substances 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 150000001340 alkali metals Chemical class 0.000 description 10
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• 125000004122 cyclic group Chemical group 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
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• 229960003878 haloperidol Drugs 0.000 description 10
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• RRLMPLDPCKRASL-UHFFFAOYSA-N 3-(dimethylamino)prop-2-enal Chemical class CN(C)C=CC=O RRLMPLDPCKRASL-UHFFFAOYSA-N 0.000 description 9
• 101150051188 Adora2a gene Proteins 0.000 description 9
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
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• 239000003054 catalyst Substances 0.000 description 9
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• 210000001364 upper extremity Anatomy 0.000 description 9
• 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 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 8
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• 208000009132 Catalepsy Diseases 0.000 description 8
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• 206010047853 Waxy flexibility Diseases 0.000 description 8
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• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 8
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• 239000004215 Carbon black (E152) Substances 0.000 description 7
• 230000008485 antagonism Effects 0.000 description 7
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• 239000003814 drug Substances 0.000 description 7
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• 229920000609 methyl cellulose Polymers 0.000 description 7
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• 239000012299 nitrogen atmosphere Substances 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 7
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