DD232696A5 - Neue amidinderivate 2-substituierter 4-phenylimidazole - Google Patents
Neue amidinderivate 2-substituierter 4-phenylimidazole Download PDFInfo
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- DD232696A5 DD232696A5 DD84265319A DD26531984A DD232696A5 DD 232696 A5 DD232696 A5 DD 232696A5 DD 84265319 A DD84265319 A DD 84265319A DD 26531984 A DD26531984 A DD 26531984A DD 232696 A5 DD232696 A5 DD 232696A5
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- DD
- German Democratic Republic
- Prior art keywords
- group
- compound
- phenyl
- formamidine
- item
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- -1 2-SUBSTITUTED 4-PHENYLIMIDAZOLE Chemical class 0.000 title claims abstract description 30
- 150000001409 amidines Chemical class 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- 230000027119 gastric acid secretion Effects 0.000 claims abstract description 3
- 239000003699 antiulcer agent Substances 0.000 claims abstract 2
- 239000003485 histamine H2 receptor antagonist Substances 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims description 3
- 229960001380 cimetidine Drugs 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 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 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- 102000000543 Histamine Receptors Human genes 0.000 claims 1
- 108010002059 Histamine Receptors Proteins 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000001530 fumaric acid Chemical class 0.000 claims 1
- 239000011976 maleic acid Chemical class 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 abstract description 3
- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 description 39
- 239000000243 solution Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 18
- CAQZTSCRGMRSHX-ODZAUARKSA-N (z)-but-2-enedioic acid;ethanol Chemical compound CCO.OC(=O)\C=C/C(O)=O CAQZTSCRGMRSHX-ODZAUARKSA-N 0.000 description 17
- GTJARIVVVORARS-ODZAUARKSA-N (z)-but-2-enedioic acid;propan-2-one Chemical compound CC(C)=O.OC(=O)\C=C/C(O)=O GTJARIVVVORARS-ODZAUARKSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 229960001340 histamine Drugs 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- QMXJGQJISYVTAH-UHFFFAOYSA-N 4-(2-methyl-1h-imidazol-5-yl)aniline Chemical compound N1C(C)=NC(C=2C=CC(N)=CC=2)=C1 QMXJGQJISYVTAH-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XTEOJPUYZWEXFI-UHFFFAOYSA-N butyl n-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate Chemical compound S1C(CC(C)C)=CC(C=2C=CC(CN3C=NC=C3)=CC=2)=C1S(=O)(=O)NC(=O)OCCCC XTEOJPUYZWEXFI-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
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- 230000002496 gastric effect Effects 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 230000010412 perfusion Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- RHTZCENGEZSDDV-UHFFFAOYSA-N n'-(2-methoxyethyl)-n-[4-(2-methyl-1h-imidazol-5-yl)phenyl]methanimidamide Chemical compound C1=CC(N=CNCCOC)=CC=C1C1=CNC(C)=N1 RHTZCENGEZSDDV-UHFFFAOYSA-N 0.000 description 3
- IJKWGOAYHQINQO-UHFFFAOYSA-N n'-hexyl-n-[4-(2-methyl-1h-imidazol-5-yl)phenyl]methanimidamide Chemical compound C1=CC(/N=C/NCCCCCC)=CC=C1C1=CNC(C)=N1 IJKWGOAYHQINQO-UHFFFAOYSA-N 0.000 description 3
- HZKOXENVRZOZSI-UHFFFAOYSA-N n-[4-(2-methyl-1h-imidazol-5-yl)phenyl]-n'-(2-methylsulfanylethyl)methanimidamide Chemical compound C1=CC(NC=NCCSC)=CC=C1C1=CN=C(C)N1 HZKOXENVRZOZSI-UHFFFAOYSA-N 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
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- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- CAQZTSCRGMRSHX-TYYBGVCCSA-N (e)-but-2-enedioic acid;ethanol Chemical compound CCO.OC(=O)\C=C\C(O)=O CAQZTSCRGMRSHX-TYYBGVCCSA-N 0.000 description 2
- YCCMWLIBASVZGU-UHFFFAOYSA-N 2-amino-5-(2-methyl-1h-imidazol-5-yl)benzonitrile Chemical compound N1C(C)=NC(C=2C=C(C(N)=CC=2)C#N)=C1 YCCMWLIBASVZGU-UHFFFAOYSA-N 0.000 description 2
- MHYNVIKBHRUCNV-UHFFFAOYSA-N 2-bromo-4-(2-methyl-1h-imidazol-5-yl)aniline Chemical compound N1C(C)=NC(C=2C=C(Br)C(N)=CC=2)=C1 MHYNVIKBHRUCNV-UHFFFAOYSA-N 0.000 description 2
- NQQSSEWMXKVTJX-UHFFFAOYSA-N 2-methyl-5-(4-nitrophenyl)-1h-imidazole Chemical compound N1C(C)=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1 NQQSSEWMXKVTJX-UHFFFAOYSA-N 0.000 description 2
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- TXQMNSSQLHWDLB-UHFFFAOYSA-N 4-(4-nitrophenyl)-1,3-dihydroimidazol-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CNC(=O)N1 TXQMNSSQLHWDLB-UHFFFAOYSA-N 0.000 description 2
- VTJUTVFOBSHNSS-UHFFFAOYSA-N 4-(4-nitrophenyl)-1,3-dihydroimidazole-2-thione Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CNC(=S)N1 VTJUTVFOBSHNSS-UHFFFAOYSA-N 0.000 description 2
- BJZNYQMDYLRHPF-UHFFFAOYSA-N 5-(4-nitrophenyl)-1h-imidazol-2-amine Chemical compound N1C(N)=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1 BJZNYQMDYLRHPF-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
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- JJVJITSFINKBBU-UHFFFAOYSA-N n-cyano-n'-[4-(2-methylsulfinyl-1h-imidazol-5-yl)phenyl]methanimidamide Chemical compound N1C(S(=O)C)=NC=C1C1=CC=C(N=CNC#N)C=C1 JJVJITSFINKBBU-UHFFFAOYSA-N 0.000 description 1
- FMCSQEJOTWONLO-UHFFFAOYSA-N n-cyano-n'-[4-(2-phenyl-1h-imidazol-5-yl)phenyl]methanimidamide Chemical compound C1=CC(N=CNC#N)=CC=C1C1=CNC(C=2C=CC=CC=2)=N1 FMCSQEJOTWONLO-UHFFFAOYSA-N 0.000 description 1
- AOBFSFVQNBTZGP-UHFFFAOYSA-N n-cyano-n'-[4-(2-sulfamoyl-1h-imidazol-5-yl)phenyl]methanimidamide Chemical compound N1C(S(=O)(=O)N)=NC(C=2C=CC(=CC=2)N=CNC#N)=C1 AOBFSFVQNBTZGP-UHFFFAOYSA-N 0.000 description 1
- HWJRQTQRAADPIC-UHFFFAOYSA-N n-cyanoformamide Chemical compound O=CNC#N HWJRQTQRAADPIC-UHFFFAOYSA-N 0.000 description 1
- SDLAKRCBYGZJRW-UHFFFAOYSA-N n-tert-butylformamide Chemical compound CC(C)(C)NC=O SDLAKRCBYGZJRW-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000008023 pharmaceutical filler Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Treatment Of Sludge (AREA)
- Processing Of Solid Wastes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8322110A IT1206498B (it) | 1983-07-18 | 1983-07-18 | Derivati amidinici del4-fenilmidazolo 2-sostituto processi per la loro preparazione e loro uso farmaceutico. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD232696A5 true DD232696A5 (de) | 1986-02-05 |
Family
ID=11191639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84265319A DD232696A5 (de) | 1983-07-18 | 1984-07-16 | Neue amidinderivate 2-substituierter 4-phenylimidazole |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4649150A (pl) |
| EP (1) | EP0131973B1 (pl) |
| JP (1) | JPS6038367A (pl) |
| KR (1) | KR910000661B1 (pl) |
| AT (1) | ATE45149T1 (pl) |
| AU (1) | AU565292B2 (pl) |
| CA (1) | CA1257274A (pl) |
| CS (1) | CS244141B2 (pl) |
| DD (1) | DD232696A5 (pl) |
| DE (1) | DE3479212D1 (pl) |
| DK (1) | DK350084A (pl) |
| ES (2) | ES8601910A1 (pl) |
| FI (1) | FI842432A (pl) |
| GB (1) | GB2149395B (pl) |
| GR (1) | GR79981B (pl) |
| HK (1) | HK74287A (pl) |
| HU (1) | HU193292B (pl) |
| IL (1) | IL72417A (pl) |
| IT (1) | IT1206498B (pl) |
| NO (1) | NO162857C (pl) |
| NZ (1) | NZ208920A (pl) |
| PH (1) | PH21566A (pl) |
| PL (2) | PL143303B1 (pl) |
| PT (1) | PT78935B (pl) |
| SG (1) | SG48687G (pl) |
| SU (2) | SU1322979A3 (pl) |
| YU (2) | YU43367B (pl) |
| ZA (1) | ZA845490B (pl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4888348A (en) * | 1986-09-04 | 1989-12-19 | Ciba-Geigy Corporation | Substituted thioureas, isothioureas and carbodiimides |
| BR9810651A (pt) | 1997-07-03 | 2000-10-03 | Neurogen Corp | Certos derivados de diarilimidazol; uma nova classe de ligantes npy especìficos |
| US6887870B1 (en) | 1999-10-12 | 2005-05-03 | Bristol-Myers Squibb Company | Heterocyclic sodium/proton exchange inhibitors and method |
| NZ519272A (en) | 1999-12-16 | 2004-02-27 | Schering Corp | Substituted imidazole neuropeptide Y Y5 receptor antagonists |
| FR2917087B1 (fr) | 2007-06-05 | 2012-09-21 | Galderma Res & Dev | Nouveaux 4-phenyl-imidazole-2-thiones comme inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique. |
| 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1209431B (it) * | 1980-11-28 | 1989-07-16 | Angeli Inst Spa | Imidazolilfenil amidine, processi per la loro preparazione e loro impiego farmaceutico, ed intermedi di preparazione. |
-
1983
- 1983-07-18 IT IT8322110A patent/IT1206498B/it active
-
1984
- 1984-05-08 EP EP84200659A patent/EP0131973B1/en not_active Expired
- 1984-05-08 DE DE8484200659T patent/DE3479212D1/de not_active Expired
- 1984-05-08 AT AT84200659T patent/ATE45149T1/de not_active IP Right Cessation
- 1984-05-16 US US06/610,958 patent/US4649150A/en not_active Expired - Fee Related
- 1984-06-15 FI FI842432A patent/FI842432A/fi not_active Application Discontinuation
- 1984-07-02 YU YU1154/84A patent/YU43367B/xx unknown
- 1984-07-09 JP JP59142099A patent/JPS6038367A/ja active Pending
- 1984-07-11 PH PH30966A patent/PH21566A/en unknown
- 1984-07-16 KR KR1019840004177A patent/KR910000661B1/ko active IP Right Grant
- 1984-07-16 DD DD84265319A patent/DD232696A5/de unknown
- 1984-07-16 IL IL72417A patent/IL72417A/xx unknown
- 1984-07-16 PL PL1984248779A patent/PL143303B1/pl unknown
- 1984-07-16 PL PL1984254625A patent/PL143732B1/pl unknown
- 1984-07-17 ES ES534376A patent/ES8601910A1/es not_active Expired
- 1984-07-17 GR GR75327A patent/GR79981B/el unknown
- 1984-07-17 CA CA000459030A patent/CA1257274A/en not_active Expired
- 1984-07-17 ES ES534375A patent/ES534375A0/es active Granted
- 1984-07-17 HU HU842781A patent/HU193292B/hu not_active IP Right Cessation
- 1984-07-17 NZ NZ208920A patent/NZ208920A/en unknown
- 1984-07-17 DK DK350084A patent/DK350084A/da not_active Application Discontinuation
- 1984-07-17 SU SU843770847A patent/SU1322979A3/ru active
- 1984-07-17 GB GB08418149A patent/GB2149395B/en not_active Expired
- 1984-07-17 ZA ZA845490A patent/ZA845490B/xx unknown
- 1984-07-17 NO NO842921A patent/NO162857C/no unknown
- 1984-07-18 AU AU30800/84A patent/AU565292B2/en not_active Ceased
- 1984-07-18 PT PT78935A patent/PT78935B/pt unknown
- 1984-07-18 CS CS845542A patent/CS244141B2/cs unknown
-
1985
- 1985-01-29 SU SU853844125A patent/SU1313345A3/ru active
-
1986
- 1986-06-26 YU YU1126/86A patent/YU43701B/xx unknown
-
1987
- 1987-06-03 SG SG486/87A patent/SG48687G/en unknown
- 1987-10-15 HK HK742/87A patent/HK74287A/xx unknown
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