NZ206853A - Pyridine-pyrimidinone derivatives and pharmaceutical compositions thereof - Google Patents
Pyridine-pyrimidinone derivatives and pharmaceutical compositions thereofInfo
- Publication number
- NZ206853A NZ206853A NZ206853A NZ20685384A NZ206853A NZ 206853 A NZ206853 A NZ 206853A NZ 206853 A NZ206853 A NZ 206853A NZ 20685384 A NZ20685384 A NZ 20685384A NZ 206853 A NZ206853 A NZ 206853A
- Authority
- NZ
- New Zealand
- Prior art keywords
- ylmethyl
- pyrimidin
- physiologically compatible
- methylpyrid
- piperidylmethyl
- 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
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 24
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229930192474 thiophene Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- RSPUWSPIQSQTRM-UHFFFAOYSA-N 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound O1C(CN(C)C)=CC=C1CSCCC(NC1=O)=NC=C1CC1=CC=CN=C1 RSPUWSPIQSQTRM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- XJJCZQKOFIDTCC-UHFFFAOYSA-N 2-[4-[3-(piperidin-1-ylmethyl)phenoxy]butyl]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound N=1C=C(CC=2C=NC=CC=2)C(=O)NC=1CCCCOC(C=1)=CC=CC=1CN1CCCCC1 XJJCZQKOFIDTCC-UHFFFAOYSA-N 0.000 claims description 2
- KAAUMLZWSTZJBG-UHFFFAOYSA-N 2-[4-[3-(piperidin-1-ylmethyl)phenoxy]butyl]-5-(pyridin-4-ylmethyl)-1h-pyrimidin-6-one Chemical compound N=1C=C(CC=2C=CN=CC=2)C(=O)NC=1CCCCOC(C=1)=CC=CC=1CN1CCCCC1 KAAUMLZWSTZJBG-UHFFFAOYSA-N 0.000 claims description 2
- BWGKHVNXSHZCHY-UHFFFAOYSA-N 2-[3-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]propyl]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound O1C(CN(C)C)=CC=C1CSCCCC(NC1=O)=NC=C1CC1=CC=CN=C1 BWGKHVNXSHZCHY-UHFFFAOYSA-N 0.000 claims 2
- VDORKCXBWVIVBA-UHFFFAOYSA-N 2-[4-[3-(piperidin-1-ylmethyl)phenoxy]butyl]-5-(pyridin-2-ylmethyl)-1h-pyrimidin-6-one Chemical compound N=1C=C(CC=2N=CC=CC=2)C(=O)NC=1CCCCOC(C=1)=CC=CC=1CN1CCCCC1 VDORKCXBWVIVBA-UHFFFAOYSA-N 0.000 claims 2
- QXAQWCMUPSZNHQ-UHFFFAOYSA-N 2-[4-[4-[(dimethylamino)methyl]phenoxy]butyl]-5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound C1=CC(CN(C)C)=CC=C1OCCCCC(NC1=O)=NC=C1CC1=CC=C(C)N=C1 QXAQWCMUPSZNHQ-UHFFFAOYSA-N 0.000 claims 2
- KZDLWOKRMAFFOL-UHFFFAOYSA-N 5-[(6-methylpyridin-3-yl)methyl]-2-[4-[4-(piperidin-1-ylmethyl)phenoxy]butyl]-1h-pyrimidin-6-one Chemical compound C1=NC(C)=CC=C1CC(C(N1)=O)=CN=C1CCCCOC(C=C1)=CC=C1CN1CCCCC1 KZDLWOKRMAFFOL-UHFFFAOYSA-N 0.000 claims 2
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 1
- NNJNSRSKINCGAR-UHFFFAOYSA-N 2-[3-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]propyl]-5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound O1C(CN(C)C)=CC=C1CSCCCC(NC1=O)=NC=C1CC1=CC=C(C)N=C1 NNJNSRSKINCGAR-UHFFFAOYSA-N 0.000 claims 1
- AVOLRPYGFKBIBZ-UHFFFAOYSA-N 2-[4-[3-[(dimethylamino)methyl]phenoxy]butyl]-5-[(6-methylpyridin-3-yl)methyl]-1h-pyrimidin-6-one Chemical compound CN(C)CC1=CC=CC(OCCCCC=2NC(=O)C(CC=3C=NC(C)=CC=3)=CN=2)=C1 AVOLRPYGFKBIBZ-UHFFFAOYSA-N 0.000 claims 1
- KVICOLRTAKRXEC-UHFFFAOYSA-N 2-[4-[4-(piperidin-1-ylmethyl)phenoxy]butyl]-5-(pyridin-3-ylmethyl)-1h-pyrimidin-6-one Chemical compound N=1C=C(CC=2C=NC=CC=2)C(=O)NC=1CCCCOC(C=C1)=CC=C1CN1CCCCC1 KVICOLRTAKRXEC-UHFFFAOYSA-N 0.000 claims 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims 1
- YOKPIRDXHAGKPZ-UHFFFAOYSA-N 5-[(6-methylpyridin-3-yl)methyl]-2-[3-[4-(piperidin-1-ylmethyl)phenoxy]propyl]-1h-pyrimidin-6-one Chemical compound C1=NC(C)=CC=C1CC(C(N1)=O)=CN=C1CCCOC(C=C1)=CC=C1CN1CCCCC1 YOKPIRDXHAGKPZ-UHFFFAOYSA-N 0.000 claims 1
- WGNXFEGVPLZUGL-UHFFFAOYSA-N 5-[(6-methylpyridin-3-yl)methyl]-2-[4-[3-(piperidin-1-ylmethyl)phenoxy]butyl]-1h-pyrimidin-6-one Chemical compound C1=NC(C)=CC=C1CC(C(N1)=O)=CN=C1CCCCOC1=CC=CC(CN2CCCCC2)=C1 WGNXFEGVPLZUGL-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001409 amidines Chemical class 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003386 piperidinyl group Chemical group 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 239000013078 crystal Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 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 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000012074 organic phase Substances 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
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- MRZYOGWSDRWMQL-UHFFFAOYSA-N 3-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]propanimidamide Chemical compound CN(C)CC1=CC=C(CSCCC(N)=N)O1 MRZYOGWSDRWMQL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229960001380 cimetidine Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- SFPIPAREYAMJEW-UHFFFAOYSA-N ethyl 2-formyl-3-pyridin-3-ylpropanoate Chemical compound CCOC(=O)C(C=O)CC1=CC=CN=C1 SFPIPAREYAMJEW-UHFFFAOYSA-N 0.000 description 3
- JRWHVJVMPKISIG-UHFFFAOYSA-N ethyl 2-formyl-3-pyridin-4-ylpropanoate Chemical compound CCOC(=O)C(C=O)CC1=CC=NC=C1 JRWHVJVMPKISIG-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 210000004211 gastric acid Anatomy 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- CGOZYZJNAFZUEZ-NHFJDJAPSA-N n,n-diethyl-4-[(e)-[4-(naphthalen-1-ylmethyl)piperazin-1-yl]iminomethyl]aniline Chemical compound C1=CC(N(CC)CC)=CC=C1\C=N\N1CCN(CC=2C3=CC=CC=C3C=CC=2)CC1 CGOZYZJNAFZUEZ-NHFJDJAPSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IMWMEIWYPWVABQ-UHFFFAOYSA-N 6-methylpyridine-3-carbaldehyde Chemical compound CC1=CC=C(C=O)C=N1 IMWMEIWYPWVABQ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 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 2
- ZABMIGDVOIATQB-UHFFFAOYSA-N ethyl 3-(6-methylpyridin-3-yl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(C)N=C1 ZABMIGDVOIATQB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000028327 secretion Effects 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
- 238000003756 stirring Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
- JSCUMHBKBWOMER-UHFFFAOYSA-N 2-pentyl-5-[4-(5-pentylpyrimidin-2-yl)phenyl]pyrimidine Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C=2C=NC(CCCCC)=NC=2)C=C1 JSCUMHBKBWOMER-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
- LLJRXVHJOJRCSM-UHFFFAOYSA-N 3-pyridin-4-yl-1H-indole Chemical group C=1NC2=CC=CC=C2C=1C1=CC=NC=C1 LLJRXVHJOJRCSM-UHFFFAOYSA-N 0.000 description 1
- SNKDWZBREZOAKC-UHFFFAOYSA-N 4-[3-(piperidin-1-ylmethyl)phenoxy]butanimidamide Chemical compound NC(=N)CCCOC1=CC=CC(CN2CCCCC2)=C1 SNKDWZBREZOAKC-UHFFFAOYSA-N 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
- QVGXQQUMFXFZKS-UHFFFAOYSA-N 5-[3-[(dimethylamino)methyl]phenoxy]pentanimidamide Chemical compound CN(C)CC1=CC=CC(OCCCCC(N)=N)=C1 QVGXQQUMFXFZKS-UHFFFAOYSA-N 0.000 description 1
- -1 6-methyl-3-pyridyl Chemical group 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 102100021022 Gastrin Human genes 0.000 description 1
- 108010052343 Gastrins Proteins 0.000 description 1
- 208000007882 Gastritis Diseases 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
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-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
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000052 comparative effect 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000138 effect on histamine Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940079360 enema for constipation Drugs 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZDXRSMCFRIFFNK-UHFFFAOYSA-N ethyl 3-pyridin-4-ylpropanoate Chemical compound CCOC(=O)CCC1=CC=NC=C1 ZDXRSMCFRIFFNK-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 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
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 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
- OFCIVGGOSSVGBR-UHFFFAOYSA-N methyl 4-[3-(piperidin-1-ylmethyl)phenoxy]butanimidate Chemical compound COC(=N)CCCOC1=CC=CC(CN2CCCCC2)=C1 OFCIVGGOSSVGBR-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum 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
- 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
- 210000005245 right atrium Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 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 |
|---|---|
| NZ206853A true NZ206853A (en) | 1986-03-14 |
Family
ID=6191499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ206853A NZ206853A (en) | 1983-02-22 | 1984-01-17 | Pyridine-pyrimidinone derivatives and pharmaceutical compositions thereof |
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 |
|---|---|
| HU192538B (en) | 1987-06-29 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU593278B2 (en) | Pharmaceutically active 2-thiomethyl-substituted-1,4- dihydropyridines | |
| EP0040696B1 (en) | Aminothiadiazoles as gastric secretion inhibitors | |
| US4279911A (en) | Amine derivatives and pharmaceutical compositions containing them | |
| EP0161841B1 (en) | 2-(n-substituteguanidino)-4-hetero-arylthiazole antiulcer agents | |
| PL113082B1 (en) | Method of guanidine derivatives preparation | |
| HU180945B (en) | Process for preparing pyrimidones | |
| HU207945B (en) | Process for producing neuropeptide-y-antagonisticpharmaceutical compositions containing imidazolyl-alkyl-guanidine derivative | |
| DE3782621T2 (de) | Imidazol-derivate, verfahren zu ihrer herstellung, pharmazeutische zubereitungen, welche diese enthalten, verwendung dieser zur herstellung therapeutisch wirksamer arzneimittel und zwischenprodukte, welche beim herstellungsverfahren entstehen. | |
| KR930011491B1 (ko) | 이미다졸릴 알킬 구아니딘 유도체의 제조방법 | |
| AU702609B2 (en) | Pyridylthio compounds for controlling helicobacter bacteria | |
| EP0262448A1 (de) | Imidazolylguanidinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| JPS62252780A (ja) | 新規なインデノチアゾ−ル誘導体及びその製造法 | |
| EP0010893B1 (en) | Antisecretory branched-chain heterocyclic guanidine derivatives, processes for their manufacture, intermediates, and pharmaceutical compositions containing said derivatives | |
| GB2063874A (en) | Triazole derivatives processes for the preparation thereof and pharmaceutical compositions containing them | |
| US4497810A (en) | Thiatriazine dioxides as gastric anti-secretory agents | |
| US4866066A (en) | Thiomethylpyridine derivatives and their use for eliciting a bronchosecretolytic or mucolytic response | |
| EP0039989B1 (en) | Pyrimidone derivatives, processes for their preparation and pharmaceutical compositions containing them | |
| US4379154A (en) | Thiocarboxamide derivatives and their use as pharmaceuticals | |
| NZ206853A (en) | Pyridine-pyrimidinone derivatives and pharmaceutical compositions thereof | |
| US4808589A (en) | Pyrimidone derivatives | |
| CA1260938A (en) | Pyrimidine-thioalkyl pyridine derivatives, a process for their production and medicaments containing these compounds | |
| EP0074229B1 (en) | Triazole gastric anti-secretory agents | |
| EP0132914A2 (en) | Imidazolinone derivatives as histamine H2-antagonists | |
| JPS58118585A (ja) | 抗潰瘍薬 | |
| US4738960A (en) | 1,3,4-Thiadiazole derivatives and pharmaceutical preparations useful as inhibitors for histamine-H2 receptors |