NO327581B1 - Pyrimidinforbindelse, farmasoytisk preparat omfattende denne, og anvendelser av forbindelsen. - Google Patents

Info

Publication number

NO327581B1

NO327581B1 NO20041580A NO20041580A NO327581B1 NO 327581 B1 NO327581 B1 NO 327581B1 NO 20041580 A NO20041580 A NO 20041580A NO 20041580 A NO20041580 A NO 20041580A NO 327581 B1 NO327581 B1 NO 327581B1

Authority

NO

Norway

Prior art keywords

group

furyl

compound

pyrimidinyl

dihydro

Prior art date

2001-10-22

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 301
• -1 Pyrimidine compound Chemical class 0.000 title description 91
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims description 62
• 239000003795 chemical substances by application Substances 0.000 claims description 52
• 239000012453 solvate Substances 0.000 claims description 47
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
• 206010010774 Constipation Diseases 0.000 claims description 43
• 238000004519 manufacturing process Methods 0.000 claims description 43
• 125000005843 halogen group Chemical group 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 20
• 125000001544 thienyl group Chemical group 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 208000018737 Parkinson disease Diseases 0.000 claims description 15
• 125000002541 furyl group Chemical group 0.000 claims description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 14
• 230000002265 prevention Effects 0.000 claims description 13
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 12
• 208000008384 ileus Diseases 0.000 claims description 11
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 8
• 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 7
• 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 6
• 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 6
• 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 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 208000011231 Crohn disease Diseases 0.000 claims description 6
• 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
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 6
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 6
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 6
• 208000001132 Osteoporosis Diseases 0.000 claims description 6
• 230000001430 anti-depressive effect Effects 0.000 claims description 6
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• 208000006673 asthma Diseases 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 239000002934 diuretic Substances 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 229940126904 hypoglycaemic agent Drugs 0.000 claims description 6
• 235000020824 obesity Nutrition 0.000 claims description 6
• 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 5
• 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 5
• 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
• 230000004064 dysfunction Effects 0.000 claims description 5
• 230000006872 improvement Effects 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 102000004877 Insulin Human genes 0.000 claims description 4
• 108090001061 Insulin Proteins 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 229940125396 insulin Drugs 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl 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 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
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 125000002560 nitrile group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 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
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 231100000489 sensitizer Toxicity 0.000 claims description 2
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 164
• 238000006243 chemical reaction Methods 0.000 description 124
• 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 108
• 239000002904 solvent Substances 0.000 description 99
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 85
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 83
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
• 239000007858 starting material Substances 0.000 description 57
• 239000002585 base Substances 0.000 description 54
• 239000000243 solution Substances 0.000 description 50
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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 42
• 239000007787 solid Substances 0.000 description 40
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 37
• 239000011541 reaction mixture Substances 0.000 description 37
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
• 239000000203 mixture Substances 0.000 description 35
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
• 238000012360 testing method Methods 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• 229910052783 alkali metal Inorganic materials 0.000 description 29
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 28
• 238000001914 filtration Methods 0.000 description 28
• 150000002357 guanidines Chemical class 0.000 description 28
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 26
• 125000004432 carbon atom Chemical group C* 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 238000003756 stirring Methods 0.000 description 24
• 102000005962 receptors Human genes 0.000 description 23
• 108020003175 receptors Proteins 0.000 description 23
• 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 22
• 238000002360 preparation method Methods 0.000 description 22
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 102000009346 Adenosine receptors Human genes 0.000 description 20
• 108050000203 Adenosine receptors Proteins 0.000 description 20
• 239000003153 chemical reaction reagent Substances 0.000 description 20
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 20
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
• 238000000034 method Methods 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
• 229920006395 saturated elastomer Polymers 0.000 description 18
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• 238000001816 cooling Methods 0.000 description 17
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• 150000003230 pyrimidines Chemical class 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
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• 230000027455 binding Effects 0.000 description 13
• 150000002170 ethers Chemical class 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
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
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