DE3726381A1 - Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE3726381A1 DE3726381A1 DE19873726381 DE3726381A DE3726381A1 DE 3726381 A1 DE3726381 A1 DE 3726381A1 DE 19873726381 DE19873726381 DE 19873726381 DE 3726381 A DE3726381 A DE 3726381A DE 3726381 A1 DE3726381 A1 DE 3726381A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- grouping
- hydrogen atom
- linear
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 11
- 229940126601 medicinal product Drugs 0.000 title claims 2
- KMSRVXJGTIRNNK-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen carbonate Chemical compound NC(N)=N.OC(O)=O KMSRVXJGTIRNNK-UHFFFAOYSA-N 0.000 title 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 103
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 86
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 53
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- -1 Guanidine carboxylic acid esters Chemical class 0.000 claims description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 22
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000002357 guanidines Chemical class 0.000 claims 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- 229910052801 chlorine Inorganic materials 0.000 description 25
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- 229910052731 fluorine Inorganic materials 0.000 description 20
- 239000011737 fluorine Substances 0.000 description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- IHDFTEVCMVTMSP-UHFFFAOYSA-N 3-(1h-imidazol-5-yl)propan-1-amine Chemical compound NCCCC1=CN=CN1 IHDFTEVCMVTMSP-UHFFFAOYSA-N 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- IHJAPZIGBLPUHC-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-pyridin-2-ylpropan-1-amine Chemical compound C=1C=CC=NC=1C(CCN)C1=CC=C(F)C=C1 IHJAPZIGBLPUHC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000011097 chromatography purification Methods 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
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000009090 positive inotropic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 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
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- HQRKLKDDESBBQC-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-(4-pyridin-2-ylbutyl)azanium;iodide Chemical compound [I-].CSC(N)=[NH+]CCCCC1=CC=CC=N1 HQRKLKDDESBBQC-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- YJVVBGVOKJWNLR-UHFFFAOYSA-N benzyl n-[n-[3-(4-fluorophenyl)-3-pyridin-2-ylpropyl]-n'-[3-(1h-imidazol-5-yl)propyl]carbamimidoyl]carbamate Chemical compound C1=CC(F)=CC=C1C(C=1N=CC=CC=1)CCN=C(NC(=O)OCC=1C=CC=CC=1)NCCCC1=CNC=N1 YJVVBGVOKJWNLR-UHFFFAOYSA-N 0.000 description 2
- PIQSXZSIGNOCFD-UHFFFAOYSA-N butyl n-[n-[3-(4-fluorophenyl)-3-pyridin-2-ylpropyl]-n'-[3-(1h-imidazol-5-yl)propyl]carbamimidoyl]carbamate Chemical compound C=1C=C(F)C=CC=1C(C=1N=CC=CC=1)CCN=C(NC(=O)OCCCC)NCCCC1=CNC=N1 PIQSXZSIGNOCFD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- SMRZJVKAEQQSTJ-UHFFFAOYSA-N ethyl n-[n'-[3-(1h-imidazol-5-yl)propyl]-n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidoyl]carbamate Chemical compound N1=CNC(C)=C1CSCCN=C(NC(=O)OCC)NCCCC1=CNC=N1 SMRZJVKAEQQSTJ-UHFFFAOYSA-N 0.000 description 2
- WGWHNWWLPRQZLP-UHFFFAOYSA-N ethyl n-[n'-[3-(1h-imidazol-5-yl)propyl]-n-[4-(pyridin-2-ylamino)butyl]carbamimidoyl]carbamate Chemical compound C=1C=CC=NC=1NCCCCN=C(NC(=O)OCC)NCCCC1=CNC=N1 WGWHNWWLPRQZLP-UHFFFAOYSA-N 0.000 description 2
- FCHLOVOYNAFDOV-UHFFFAOYSA-N ethyl n-[n-[3-(4-fluorophenyl)-3-pyridin-2-ylpropyl]-n'-[3-(1h-imidazol-5-yl)propyl]carbamimidoyl]carbamate Chemical compound C=1C=C(F)C=CC=1C(C=1N=CC=CC=1)CCN=C(NC(=O)OCC)NCCCC1=CNC=N1 FCHLOVOYNAFDOV-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000000004 hemodynamic effect Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- MURRAGMMNAYLNA-UHFFFAOYSA-N impromidine Chemical compound N1C=NC(CSCCNC(N)=NCCCC=2NC=NC=2)=C1C MURRAGMMNAYLNA-UHFFFAOYSA-N 0.000 description 2
- 229950005073 impromidine Drugs 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- YEKKHQKICZDRAO-UHFFFAOYSA-N methyl n-[n-[3-(1h-imidazol-5-yl)propyl]-n'-[3-(n-pyridin-2-ylanilino)propyl]carbamimidoyl]carbamate Chemical compound C=1C=CC=CC=1N(C=1N=CC=CC=1)CCCN=C(NC(=O)OC)NCCCC1=CNC=N1 YEKKHQKICZDRAO-UHFFFAOYSA-N 0.000 description 2
- OYEIMFKDCFEOOW-UHFFFAOYSA-N methyl n-[n-[3-(4-fluorophenyl)-3-pyridin-2-ylpropyl]-n'-[3-(1h-imidazol-5-yl)propyl]carbamimidoyl]carbamate Chemical compound C=1C=C(F)C=CC=1C(C=1N=CC=CC=1)CCN=C(NC(=O)OC)NCCCC1=CNC=N1 OYEIMFKDCFEOOW-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- ZJBRVRANNHWTBD-UHFFFAOYSA-N phenyl n-[n-[3-(4-fluorophenyl)-3-pyridin-2-ylpropyl]-n'-[3-(1h-imidazol-5-yl)propyl]carbamimidoyl]carbamate Chemical compound C1=CC(F)=CC=C1C(C=1N=CC=CC=1)CCN=C(NC(=O)OC=1C=CC=CC=1)NCCCC1=CNC=N1 ZJBRVRANNHWTBD-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-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
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 101150046432 Tril gene Proteins 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- WWNKNMUEIPPBIU-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-[2-[(4-chlorophenyl)methyl-pyridin-2-ylamino]ethyl]azanium iodide Chemical compound [I-].C=1C=CC=NC=1N(CC[NH+]=C(N)SC)CC1=CC=C(Cl)C=C1 WWNKNMUEIPPBIU-UHFFFAOYSA-N 0.000 description 1
- DGLSUFNMSSVIDH-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-[3-(n-pyridin-2-ylanilino)propyl]azanium;iodide Chemical compound [I-].C=1C=CC=NC=1N(CCC[NH+]=C(N)SC)C1=CC=CC=C1 DGLSUFNMSSVIDH-UHFFFAOYSA-N 0.000 description 1
- VGFOTUWZKBZFNV-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-[4-(pyridin-2-ylamino)butyl]azanium;iodide Chemical compound [I-].CSC(N)=[NH+]CCCCNC1=CC=CC=N1 VGFOTUWZKBZFNV-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 210000001765 aortic valve Anatomy 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000009977 dual effect 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
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- KYXQKKTUIQMUMS-UHFFFAOYSA-N ethyl n-[n'-[3-(1h-imidazol-5-yl)propyl]-n-(4-pyridin-2-ylbutyl)carbamimidoyl]carbamate Chemical compound C=1C=CC=NC=1CCCCN=C(NC(=O)OCC)NCCCC1=CNC=N1 KYXQKKTUIQMUMS-UHFFFAOYSA-N 0.000 description 1
- JJLXJHIOPNXBHN-UHFFFAOYSA-N ethyl n-[n-[2-[(4-chlorophenyl)methyl-pyridin-2-ylamino]ethyl]-n'-[3-(1h-imidazol-5-yl)propyl]carbamimidoyl]carbamate Chemical compound C=1C=C(Cl)C=CC=1CN(C=1N=CC=CC=1)CCN=C(NC(=O)OCC)NCCCC1=CNC=N1 JJLXJHIOPNXBHN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- OPGQGYQPVOWUOO-UHFFFAOYSA-N methyl n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NCCSCC=1N=CNC=1C OPGQGYQPVOWUOO-UHFFFAOYSA-N 0.000 description 1
- DPTRIXAWYKXUCX-UHFFFAOYSA-N methyl n-[n'-[3-(1h-imidazol-5-yl)propyl]-n-(4-pyridin-2-ylbutyl)carbamimidoyl]carbamate Chemical compound C=1C=CC=NC=1CCCCN=C(NC(=O)OC)NCCCC1=CNC=N1 DPTRIXAWYKXUCX-UHFFFAOYSA-N 0.000 description 1
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
- 229960002237 metoprolol Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base 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
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873726381 DE3726381A1 (de) | 1987-08-07 | 1987-08-07 | Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE8888102371T DE3877454D1 (de) | 1987-08-07 | 1988-02-18 | Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
| ES88102371T ES2053595T3 (es) | 1987-08-07 | 1988-02-18 | Ester de acido de carbonato de guanidina, procedimiento para su produccion y remedios contenidos en esta union. |
| AT88102371T ATE84531T1 (de) | 1987-08-07 | 1988-02-18 | Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
| EP88102371A EP0302164B1 (de) | 1987-08-07 | 1988-02-18 | Guanidincarbonsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| ZA881271A ZA881271B (en) | 1987-08-07 | 1988-02-24 | Guanidine carboxylic acid esters,processes for their preparation and pharmaceutical preparations containing these compounds |
| IL85542A IL85542A0 (en) | 1987-08-07 | 1988-02-24 | Guanidine carboxylic acid esters,processes for their preparation and pharmaceutical preparations containing these compounds |
| AU12320/88A AU599752B2 (en) | 1987-08-07 | 1988-02-26 | Guanidine carboxylic acid esters, processes for their preparation and pharmaceutical preparations containing these compounds |
| NZ223684A NZ223684A (en) | 1987-08-07 | 1988-02-29 | Guanidine carboxylic acid esters and pharmaceutical compositions |
| CA000560361A CA1304086C (en) | 1987-08-07 | 1988-03-02 | Guanidine carboxylic acid esters, processes for their preparation and pharmaceutical preparations containing these compounds |
| AR88310486A AR243873A1 (es) | 1987-08-07 | 1988-04-05 | Procedimiento de preparacion de derivados de guanidina. |
| PT87184A PT87184B (pt) | 1987-08-07 | 1988-04-07 | Processo para a preparacao de derivados de guanidina e de composicoes farmaceuticas que os contem |
| DK194388A DK194388A (da) | 1987-08-07 | 1988-04-08 | Guanidincarboxylsyreestere, fremgangsmaade til fremstilling heraf samt laegemidler indeholdende disse forbindelser |
| HU881444A HUT49604A (en) | 1987-08-07 | 1988-04-08 | Process for producing guanidinecarboxylic acid esters and pharmaceutical compositions comprising same |
| HU881777A HU201053B (en) | 1987-08-07 | 1988-04-08 | Process for production of guanidin carbonic acid esthers and medical compositions containing them |
| IE105088A IE63297B1 (en) | 1987-08-07 | 1988-04-08 | Guanidine carboxylic acid esters,processes for their preparation and pharmaceutical preparations containing these compounds |
| JP63088017A JPS6442470A (en) | 1987-08-07 | 1988-04-08 | Guanidinecarboxylic acid esters, manufacture and medicinal composition |
| KR1019880004088A KR890003737A (ko) | 1987-08-07 | 1988-04-11 | 구아니딘 카르복실산 에스테르와 그 제법 및 이를 함유하는 약학적 제제 |
| US07/180,135 US4948802A (en) | 1987-08-07 | 1988-04-11 | Guanidine carboxylic acid esters and pharmaceutical preparations containing these compounds |
| GR930400045T GR3006790T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-08-07 | 1993-01-14 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873726381 DE3726381A1 (de) | 1987-08-07 | 1987-08-07 | Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3726381A1 true DE3726381A1 (de) | 1989-02-16 |
Family
ID=6333331
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873726381 Withdrawn DE3726381A1 (de) | 1987-08-07 | 1987-08-07 | Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE8888102371T Expired - Fee Related DE3877454D1 (de) | 1987-08-07 | 1988-02-18 | Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8888102371T Expired - Fee Related DE3877454D1 (de) | 1987-08-07 | 1988-02-18 | Guanidincarbonsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
Country Status (18)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0437645A1 (de) * | 1990-01-15 | 1991-07-24 | HEUMANN PHARMA GMBH & CO | Imidazolylpropylguanidinderivat, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3631334A1 (de) * | 1986-09-15 | 1988-03-17 | Heumann Pharma Gmbh & Co | Neue imidazolylguanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| USRE37303E1 (en) * | 1992-01-10 | 2001-07-31 | Institut National Del La Sante Et De La Recherche Medicale | Imidazole compounds and their therapeutic applications |
| FR2686084B1 (fr) * | 1992-01-10 | 1995-12-22 | Bioprojet Soc Civ | Nouveaux derives de l'imidazole, leur preparation et leurs applications therapeutiques. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968216A (en) * | 1969-10-29 | 1976-07-06 | Smith Kline & French Laboratories Limited | Method of inhibiting histamine activity with guanidine compounds |
| BE758146A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
| GB1305547A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-10-29 | 1973-02-07 | ||
| DE2630847A1 (de) * | 1976-07-09 | 1978-01-19 | Bayer Ag | Methoxycarbonyl-phenyl-guanidine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3512084A1 (de) * | 1985-04-02 | 1986-10-09 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Guanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3528214A1 (de) * | 1985-08-06 | 1987-02-12 | Heumann Ludwig & Co Gmbh | Arylalkylguanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0199845B1 (de) * | 1985-04-02 | 1990-08-01 | HEUMANN PHARMA GMBH & CO | Imidazolylalkylguanidinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE3528215A1 (de) * | 1985-08-06 | 1987-02-12 | Heumann Ludwig & Co Gmbh | Heteroarylalkylguanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3631334A1 (de) * | 1986-09-15 | 1988-03-17 | Heumann Pharma Gmbh & Co | Neue imidazolylguanidinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1987
- 1987-08-07 DE DE19873726381 patent/DE3726381A1/de not_active Withdrawn
-
1988
- 1988-02-18 EP EP88102371A patent/EP0302164B1/de not_active Expired - Lifetime
- 1988-02-18 DE DE8888102371T patent/DE3877454D1/de not_active Expired - Fee Related
- 1988-02-18 ES ES88102371T patent/ES2053595T3/es not_active Expired - Lifetime
- 1988-02-18 AT AT88102371T patent/ATE84531T1/de not_active IP Right Cessation
- 1988-02-24 IL IL85542A patent/IL85542A0/xx not_active IP Right Cessation
- 1988-02-24 ZA ZA881271A patent/ZA881271B/xx unknown
- 1988-02-26 AU AU12320/88A patent/AU599752B2/en not_active Ceased
- 1988-02-29 NZ NZ223684A patent/NZ223684A/xx unknown
- 1988-03-02 CA CA000560361A patent/CA1304086C/en not_active Expired - Lifetime
- 1988-04-05 AR AR88310486A patent/AR243873A1/es active
- 1988-04-07 PT PT87184A patent/PT87184B/pt not_active IP Right Cessation
- 1988-04-08 HU HU881777A patent/HU201053B/hu not_active IP Right Cessation
- 1988-04-08 HU HU881444A patent/HUT49604A/hu unknown
- 1988-04-08 JP JP63088017A patent/JPS6442470A/ja active Pending
- 1988-04-08 DK DK194388A patent/DK194388A/da not_active Application Discontinuation
- 1988-04-08 IE IE105088A patent/IE63297B1/en not_active IP Right Cessation
- 1988-04-11 KR KR1019880004088A patent/KR890003737A/ko not_active Ceased
- 1988-04-11 US US07/180,135 patent/US4948802A/en not_active Expired - Fee Related
-
1993
- 1993-01-14 GR GR930400045T patent/GR3006790T3/el unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0437645A1 (de) * | 1990-01-15 | 1991-07-24 | HEUMANN PHARMA GMBH & CO | Imidazolylpropylguanidinderivat, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel |
| AU624757B2 (en) * | 1990-01-15 | 1992-06-18 | Heumann Pharma Gmbh & Co. | Imidazilyl propyl guanidine derivative, a process for its preparation and a pharmaceutical composition containing this compound |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0302164A1 (de) | 1989-02-08 |
| JPS6442470A (en) | 1989-02-14 |
| DK194388A (da) | 1989-02-08 |
| EP0302164B1 (de) | 1993-01-13 |
| AU599752B2 (en) | 1990-07-26 |
| NZ223684A (en) | 1989-11-28 |
| HUT49604A (en) | 1989-10-30 |
| KR890003737A (ko) | 1989-04-17 |
| IE881050L (en) | 1989-02-07 |
| ES2053595T3 (es) | 1994-08-01 |
| GR3006790T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-06-30 |
| HU201053B (en) | 1990-09-28 |
| PT87184A (pt) | 1989-06-30 |
| AR243873A1 (es) | 1993-09-30 |
| US4948802A (en) | 1990-08-14 |
| CA1304086C (en) | 1992-06-23 |
| ATE84531T1 (de) | 1993-01-15 |
| PT87184B (pt) | 1995-03-01 |
| DE3877454D1 (de) | 1993-02-25 |
| DK194388D0 (da) | 1988-04-08 |
| ZA881271B (en) | 1988-08-22 |
| IL85542A0 (en) | 1988-08-31 |
| AU1232088A (en) | 1989-02-09 |
| IE63297B1 (en) | 1995-04-05 |
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