HU192538B - Process for producing pyridine-pyrimidinone derivatives and pharmaceutical compositions containing them - Google Patents
Process for producing pyridine-pyrimidinone derivatives and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HU192538B HU192538B HU84652A HU65284A HU192538B HU 192538 B HU192538 B HU 192538B HU 84652 A HU84652 A HU 84652A HU 65284 A HU65284 A HU 65284A HU 192538 B HU192538 B HU 192538B
- Authority
- HU
- Hungary
- Prior art keywords
- ring
- formula
- pyridine
- methyl
- mmol
- Prior art date
Links
- WKONRVDUTQPZHA-UHFFFAOYSA-N pyridine;1h-pyrimidin-2-one Chemical class C1=CC=NC=C1.O=C1N=CC=CN1 WKONRVDUTQPZHA-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- -1 phenyleneoxy group Chemical group 0.000 claims description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 5
- 201000005917 gastric ulcer Diseases 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 208000007882 Gastritis Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 229930192474 thiophene Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000013078 crystal Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- RNSSBLFWCWUJGW-UHFFFAOYSA-N C(C)C(C(=O)O)(CC=1C=NC=CC1)C=O Chemical compound C(C)C(C(=O)O)(CC=1C=NC=CC1)C=O RNSSBLFWCWUJGW-UHFFFAOYSA-N 0.000 description 3
- XAXILKDBPQWQSY-UHFFFAOYSA-N CCC(CC1=CC=C(C)N=C1)(C=O)C(O)=O Chemical compound CCC(CC1=CC=C(C)N=C1)(C=O)C(O)=O XAXILKDBPQWQSY-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 3
- 229960001380 cimetidine Drugs 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 2
- HASSDDVOAGEEPH-UHFFFAOYSA-N CCC(CC1=CC=NC=C1)(C=O)C(O)=O Chemical compound CCC(CC1=CC=NC=C1)(C=O)C(O)=O HASSDDVOAGEEPH-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 210000004211 gastric acid Anatomy 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- LPXCHPSTROLSJX-UHFFFAOYSA-N pentanimidamide Chemical compound CCCCC(N)=N LPXCHPSTROLSJX-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PXGKFIPYAOCSAU-UHFFFAOYSA-N 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound O1C(CN(C)C)=CC=C1CSCCC(NC1=O)=NC=C1CC1=CC=C(C)N=C1 PXGKFIPYAOCSAU-UHFFFAOYSA-N 0.000 description 1
- PSJNWRRIPQIURU-UHFFFAOYSA-N 2-phenoxypentanamide Chemical compound CCCC(C(N)=O)OC1=CC=CC=C1 PSJNWRRIPQIURU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- FSRCZTXBDHUVLO-UHFFFAOYSA-N 5-[(6-methylpyridin-3-yl)methyl]-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1h-pyrimidin-6-one Chemical compound C1=NC(C)=CC=C1CC(C(N1)=O)=CN=C1CCCOC1=CC=CC(CN2CCCCC2)=C1 FSRCZTXBDHUVLO-UHFFFAOYSA-N 0.000 description 1
- DQSPPPLABNDYIS-UHFFFAOYSA-N 5-[3-(piperidin-1-ylmethyl)phenoxy]pentanimidamide Chemical compound NC(=N)CCCCOC1=CC=CC(CN2CCCCC2)=C1 DQSPPPLABNDYIS-UHFFFAOYSA-N 0.000 description 1
- FTYFZOHWJMBWKK-UHFFFAOYSA-N 5-[4-(piperidin-1-ylmethyl)phenoxy]pentanimidamide Chemical compound C1=CC(OCCCCC(=N)N)=CC=C1CN1CCCCC1 FTYFZOHWJMBWKK-UHFFFAOYSA-N 0.000 description 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- IMWMEIWYPWVABQ-UHFFFAOYSA-N 6-methylpyridine-3-carbaldehyde Chemical compound CC1=CC=C(C=O)C=N1 IMWMEIWYPWVABQ-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- PMRANSXXCHYFHM-UHFFFAOYSA-N N1=CC=C(C=C1)C=CC(=O)OCC.N1=CC=C(C=C1)CCC(=O)OCC Chemical compound N1=CC=C(C=C1)C=CC(=O)OCC.N1=CC=C(C=C1)CCC(=O)OCC PMRANSXXCHYFHM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- IIOWETJNAPDAGC-UHFFFAOYSA-N ethyl 2-formyl-3-(6-methylpyridin-3-yl)propanoate Chemical compound CCOC(=O)C(C=O)CC1=CC=C(C)N=C1 IIOWETJNAPDAGC-UHFFFAOYSA-N 0.000 description 1
- HCRBXQFHJMCTLF-UHFFFAOYSA-N ethyl 2-methylbutyrate Chemical compound CCOC(=O)C(C)CC HCRBXQFHJMCTLF-UHFFFAOYSA-N 0.000 description 1
- UPQKGGCHMZDTBL-UHFFFAOYSA-N ethyl 3-(6-methylpyridin-3-yl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(C)N=C1 UPQKGGCHMZDTBL-UHFFFAOYSA-N 0.000 description 1
- ABZPCWYIRGIXJP-UHFFFAOYSA-N ethyl 3-pyridin-4-ylprop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=NC=C1 ABZPCWYIRGIXJP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 239000003453 histamine agonist Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
- 229960002329 methacholine Drugs 0.000 description 1
- CMCRGQRFVJZHBR-UHFFFAOYSA-N methyl 3-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]propanimidate Chemical compound COC(=N)CCSCC1=CC=C(CN(C)C)O1 CMCRGQRFVJZHBR-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3306102A DE3306102C1 (de) | 1983-02-22 | 1983-02-22 | Pyridin-Pyrimidinon-Derivate,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU192538B true HU192538B (en) | 1987-06-29 |
Family
ID=6191499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU84652A HU192538B (en) | 1983-02-22 | 1984-02-20 | Process for producing pyridine-pyrimidinone derivatives and pharmaceutical compositions containing them |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4559344A (en, 2012) |
| EP (1) | EP0119510B1 (en, 2012) |
| JP (1) | JPS59163385A (en, 2012) |
| KR (1) | KR840007595A (en, 2012) |
| AT (1) | ATE26713T1 (en, 2012) |
| AU (1) | AU562495B2 (en, 2012) |
| DE (2) | DE3306102C1 (en, 2012) |
| DK (1) | DK42784A (en, 2012) |
| ES (1) | ES8407293A1 (en, 2012) |
| GR (1) | GR79815B (en, 2012) |
| HU (1) | HU192538B (en, 2012) |
| IE (1) | IE840386L (en, 2012) |
| IL (1) | IL70594A (en, 2012) |
| NZ (1) | NZ206853A (en, 2012) |
| PT (1) | PT78004B (en, 2012) |
| YU (1) | YU254283A (en, 2012) |
| ZA (1) | ZA839589B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8411954D0 (en) * | 1984-05-10 | 1984-06-13 | Glaxo Group Ltd | Cephalosporin antibiotics |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
| US4521418A (en) * | 1979-02-21 | 1985-06-04 | Smith Kline & French Laboratories Limited | Guanidinothiazolyl derivatives |
| CA1211111A (en) * | 1982-02-15 | 1986-09-09 | Isao Yanagisawa | Process for preparing novel pyrimidone compounds |
| US4808589A (en) * | 1982-02-20 | 1989-02-28 | Smith Kline & French Laboratories Limited | Pyrimidone derivatives |
-
1983
- 1983-02-22 DE DE3306102A patent/DE3306102C1/de not_active Expired
- 1983-12-20 YU YU02542/83A patent/YU254283A/xx unknown
- 1983-12-21 AU AU22723/83A patent/AU562495B2/en not_active Ceased
- 1983-12-27 ZA ZA839589A patent/ZA839589B/xx unknown
-
1984
- 1984-01-01 IL IL70594A patent/IL70594A/xx unknown
- 1984-01-10 GR GR73465A patent/GR79815B/el unknown
- 1984-01-17 NZ NZ206853A patent/NZ206853A/en unknown
- 1984-01-21 KR KR1019840000268A patent/KR840007595A/ko not_active Withdrawn
- 1984-01-25 PT PT78004A patent/PT78004B/pt unknown
- 1984-01-26 US US06/574,077 patent/US4559344A/en not_active Expired - Fee Related
- 1984-01-31 DK DK42784A patent/DK42784A/da not_active Application Discontinuation
- 1984-02-02 ES ES529415A patent/ES8407293A1/es not_active Expired
- 1984-02-20 JP JP59031340A patent/JPS59163385A/ja active Pending
- 1984-02-20 IE IE840386A patent/IE840386L/xx unknown
- 1984-02-20 HU HU84652A patent/HU192538B/hu unknown
- 1984-02-22 AT AT84101863T patent/ATE26713T1/de not_active IP Right Cessation
- 1984-02-22 EP EP84101863A patent/EP0119510B1/de not_active Expired
- 1984-02-22 DE DE8484101863T patent/DE3463270D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES529415A0 (es) | 1984-10-01 |
| KR840007595A (ko) | 1984-12-08 |
| IL70594A0 (en) | 1984-04-30 |
| AU2272383A (en) | 1984-08-30 |
| US4559344A (en) | 1985-12-17 |
| YU254283A (en) | 1986-06-30 |
| PT78004B (de) | 1986-04-10 |
| EP0119510B1 (de) | 1987-04-22 |
| ES8407293A1 (es) | 1984-10-01 |
| IE840386L (en) | 1984-08-22 |
| DE3463270D1 (en) | 1987-05-27 |
| IL70594A (en) | 1988-06-30 |
| EP0119510A1 (de) | 1984-09-26 |
| DE3306102C1 (de) | 1984-08-02 |
| ZA839589B (en) | 1984-09-26 |
| PT78004A (de) | 1984-02-01 |
| DK42784A (da) | 1984-08-23 |
| JPS59163385A (ja) | 1984-09-14 |
| ATE26713T1 (de) | 1987-05-15 |
| GR79815B (en, 2012) | 1984-10-31 |
| DK42784D0 (da) | 1984-01-31 |
| AU562495B2 (en) | 1987-06-11 |
| NZ206853A (en) | 1986-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR910002583B1 (ko) | 피페라진 유도체 또는 이의 염, 이의 제조방법 및 활성 성분으로서 이를 함유하는 약제학적 조성물 | |
| KR100303737B1 (ko) | 피페라진유도체 | |
| SK14562001A3 (sk) | Substituované azoly, spôsob ich prípravy, farmaceutická kompozícia s ich obsahom a ich použitie | |
| US4735956A (en) | Certain 1,4-dihydro-2,6-di-lower hydrocarbyl-4-heterocyclic-3,5-pyridine dicarboxylates which are useful as calcium channel blockers | |
| JPS6056143B2 (ja) | アミジン誘導体ならびにその製造法 | |
| KR100632188B1 (ko) | 신규한피페라진및피페리딘화합물 | |
| KR960010346B1 (ko) | 4(3h)-퀴나졸리논 유도체, 이의 제조방법 및 약제학적 조성물 | |
| KR900006742B1 (ko) | N-[(2-옥소피롤리딘-1-일)아세틸]피페라진 유도체 및 노인성 치매용 약제 | |
| HU196786B (en) | Process for production of new indol-derivatives and medical compositions containing them | |
| WO2002022588A1 (fr) | Nouveau derive de pyrimidine et nouveau derive de pyridine | |
| JP2707936B2 (ja) | β−オキソ−β−ベンゼンプロパンチオアミド誘導体 | |
| KR960010345B1 (ko) | 4－티오퀴나졸린 유도체, 이의 제조방법 및 약제학적 조성물 | |
| EP0080154B1 (de) | N-Substituierte 2-Pyridylindole, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung | |
| US5847123A (en) | Imide derivatives for inhibiting the production of interleukin-1β and the production of tumor necrosis factor α | |
| GB2063874A (en) | Triazole derivatives processes for the preparation thereof and pharmaceutical compositions containing them | |
| KR100248643B1 (ko) | 아릴 및 헤테로아릴 알콕시나프탈렌 유도체 | |
| HU192538B (en) | Process for producing pyridine-pyrimidinone derivatives and pharmaceutical compositions containing them | |
| DE69227207T2 (de) | 1-Piperazinyl-2-butene und 2-butyne, Zwischenverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| EP0129051B1 (de) | Substituierte Indole | |
| KR840001775B1 (ko) | 헤테로 사이클릭 유도체의 제조방법 | |
| EP0257616A2 (en) | Dihydropyridine derivates and pharmaceutical composition thereof | |
| US5045550A (en) | Substituted tetrahydropyridines as central nervous system agents | |
| US4886819A (en) | Dihydropyridine derivatives and pharmaceutical composition thereof | |
| JPH0377191B2 (en, 2012) | ||
| EP0378358B1 (en) | Anti-inflammmatory 1-heteroaryl-3-acyl-2-oxindoles |