CH616160A5 - Process for the preparation of novel compounds which affect gastric acid secretion - Google Patents
Process for the preparation of novel compounds which affect gastric acid secretion Download PDFInfo
- Publication number
- CH616160A5 CH616160A5 CH182975A CH182975A CH616160A5 CH 616160 A5 CH616160 A5 CH 616160A5 CH 182975 A CH182975 A CH 182975A CH 182975 A CH182975 A CH 182975A CH 616160 A5 CH616160 A5 CH 616160A5
- Authority
- CH
- Switzerland
- Prior art keywords
- benzimidazole
- pyridylmethylthio
- hydrogen
- formula
- het
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000027119 gastric acid secretion Effects 0.000 title description 7
- -1 alkyl radicals Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001556 benzimidazoles Chemical class 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical compound [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 4
- LUYGPXKGASNPBJ-UHFFFAOYSA-N 1-[2-(pyridin-2-ylmethylsulfanyl)-3h-benzimidazol-5-yl]ethanone Chemical compound N1C2=CC(C(=O)C)=CC=C2N=C1SCC1=CC=CC=N1 LUYGPXKGASNPBJ-UHFFFAOYSA-N 0.000 claims 1
- NITVBBPJJSFMDC-UHFFFAOYSA-N 1-[2-(pyridin-2-ylmethylsulfanyl)benzimidazol-1-yl]ethanone Chemical compound N=1C2=CC=CC=C2N(C(=O)C)C=1SCC1=CC=CC=N1 NITVBBPJJSFMDC-UHFFFAOYSA-N 0.000 claims 1
- JQRFQTFEVIQCIB-UHFFFAOYSA-N 2-(1-pyridin-2-ylethylsulfanyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1SC(C)C1=CC=CC=N1 JQRFQTFEVIQCIB-UHFFFAOYSA-N 0.000 claims 1
- FIPBUIKUTXFUKH-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-3h-benzimidazol-5-ol Chemical compound N1C2=CC(O)=CC=C2N=C1SCC1=CC=CC=N1 FIPBUIKUTXFUKH-UHFFFAOYSA-N 0.000 claims 1
- LPAWGRXVTOHGDE-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-3h-benzimidazole-5-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2N=C1SCC1=CC=CC=N1 LPAWGRXVTOHGDE-UHFFFAOYSA-N 0.000 claims 1
- MFMAZRYFOISOOH-UHFFFAOYSA-N 4,6-dimethyl-2-(pyridin-2-ylmethylsulfanyl)-1h-benzimidazole Chemical compound N=1C2=CC(C)=CC(C)=C2NC=1SCC1=CC=CC=N1 MFMAZRYFOISOOH-UHFFFAOYSA-N 0.000 claims 1
- COETYDWSJDWTFB-UHFFFAOYSA-N 4-methyl-2-(pyridin-2-ylmethylsulfanyl)-1h-benzimidazole Chemical compound N1C=2C(C)=CC=CC=2N=C1SCC1=CC=CC=N1 COETYDWSJDWTFB-UHFFFAOYSA-N 0.000 claims 1
- DXOHZYSSDZZNQQ-UHFFFAOYSA-N 6-ethyl-2-(pyridin-2-ylmethylsulfanyl)-1h-benzimidazole Chemical compound N1C2=CC(CC)=CC=C2N=C1SCC1=CC=CC=N1 DXOHZYSSDZZNQQ-UHFFFAOYSA-N 0.000 claims 1
- ASVPNBDOVHTUEM-UHFFFAOYSA-N 6-methoxy-2-(pyridin-2-ylmethylsulfanyl)-1h-benzimidazole Chemical compound N1C2=CC(OC)=CC=C2N=C1SCC1=CC=CC=N1 ASVPNBDOVHTUEM-UHFFFAOYSA-N 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- MZCJTSYIUCXIGU-UHFFFAOYSA-N ethyl 2-(pyridin-2-ylmethylsulfanyl)-3h-benzimidazole-5-carboxylate Chemical compound N1C2=CC(C(=O)OCC)=CC=C2N=C1SCC1=CC=CC=N1 MZCJTSYIUCXIGU-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- 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
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- LNSCNEJNLACZPA-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(2-methylphenyl)butanedioic acid Chemical compound CC1=CC=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=CC=C1C LNSCNEJNLACZPA-UHFFFAOYSA-N 0.000 description 1
- SPMLMLQATWNZEE-UHFFFAOYSA-N 2-(chloromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(CCl)=NC2=C1 SPMLMLQATWNZEE-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-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
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- UDQCDDZBBZNIFA-UHFFFAOYSA-N 4-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=CC2=C1NC(=S)N2 UDQCDDZBBZNIFA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-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
- 239000005977 Ethylene Substances 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
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- 241000124008 Mammalia Species 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 108010079943 Pentagastrin Proteins 0.000 description 1
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- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
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- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 230000001399 anti-metabolic effect Effects 0.000 description 1
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- 150000002500 ions Chemical class 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
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- 238000002844 melting Methods 0.000 description 1
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- 229930182817 methionine Natural products 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 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
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- PEEXCRJDFUVJRT-UHFFFAOYSA-M potassium;methoxymethanedithioate Chemical compound [K+].COC([S-])=S PEEXCRJDFUVJRT-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001549 tubercolostatic effect Effects 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7402101A SE418966B (sv) | 1974-02-18 | 1974-02-18 | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616160A5 true CH616160A5 (en) | 1980-03-14 |
Family
ID=20320233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH182975A CH616160A5 (en) | 1974-02-18 | 1975-02-14 | Process for the preparation of novel compounds which affect gastric acid secretion |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5924157B2 (en, 2012) |
| AT (1) | AT343659B (en, 2012) |
| AU (1) | AU499639B2 (en, 2012) |
| BE (1) | BE825655A (en, 2012) |
| CA (1) | CA1060448A (en, 2012) |
| CH (1) | CH616160A5 (en, 2012) |
| CS (1) | CS194715B2 (en, 2012) |
| DD (1) | DD119422A5 (en, 2012) |
| DE (1) | DE2504252A1 (en, 2012) |
| DK (1) | DK141122B (en, 2012) |
| FI (1) | FI59590C (en, 2012) |
| FR (1) | FR2261007B1 (en, 2012) |
| GB (1) | GB1500043A (en, 2012) |
| HK (1) | HK67080A (en, 2012) |
| HU (1) | HU172141B (en, 2012) |
| IE (1) | IE40858B1 (en, 2012) |
| LU (1) | LU71872A1 (en, 2012) |
| MY (1) | MY8100208A (en, 2012) |
| NL (1) | NL7501917A (en, 2012) |
| NO (1) | NO142401C (en, 2012) |
| SE (1) | SE418966B (en, 2012) |
| SU (1) | SU795476A3 (en, 2012) |
| ZA (1) | ZA75558B (en, 2012) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE416649B (sv) * | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| JPS5364103A (en) * | 1976-09-24 | 1978-06-08 | Hitachi Ltd | Waste heat recovery boiler |
| IN148930B (en, 2012) | 1977-09-19 | 1981-07-25 | Hoffmann La Roche | |
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| US4343805A (en) * | 1978-12-16 | 1982-08-10 | John Wyeth & Brother Limited | Heterocyclic compounds |
| AT373888B (de) * | 1979-01-10 | 1984-02-27 | Janssen Pharmaceutica Nv | Verfahren zur herstellung von neuen 4-piperidinaminen und deren saeureadditionssalzen |
| CH644116A5 (de) * | 1980-08-21 | 1984-07-13 | Hoffmann La Roche | Imidazolderivate. |
| DE3047388A1 (de) * | 1980-12-16 | 1982-07-15 | Basf Ag, 6700 Ludwigshafen | Isatogenderivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| IL66340A (en) * | 1981-08-13 | 1986-08-31 | Haessle Ab | Pharmaceutical compositions comprising pyridylmethyl-thiobenzimidazole derivatives,certain such novel derivatives and their preparation |
| DE3216843C2 (de) * | 1982-05-05 | 1986-10-23 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | 3-Thiomethyl-pyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4552886A (en) * | 1982-06-07 | 1985-11-12 | Eli Lilly And Company | Fungicidal pyridylmethyl-amines |
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| GB8307865D0 (en) * | 1983-03-22 | 1983-04-27 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| US4503139A (en) * | 1983-05-09 | 1985-03-05 | Polaroid Corporation | Photographic products and processes and novel compounds |
| US4575554A (en) * | 1983-12-05 | 1986-03-11 | The Upjohn Company | Substituted 2-pyridylmethylthio- and sulfinyl-benzimidazoles as gastric antisecretory agents |
| US4767770A (en) * | 1984-06-18 | 1988-08-30 | Eli Lilly And Company | Method of inhibiting aromatase |
| SE8505112D0 (sv) * | 1985-10-29 | 1985-10-29 | Haessle Ab | Novel pharmacological compounds |
| FR2593178B1 (fr) * | 1986-01-20 | 1988-04-29 | Esteve Labor Dr | Derives de 2-benzimidazolylalkylthio (ou sulfinyle ou sulfonyle) leur preparation et leur application en tant que medicaments. |
| SE8600658D0 (sv) * | 1986-02-14 | 1986-02-14 | Haessle Ab | Novel composition of matter |
| SE8604566D0 (sv) * | 1986-10-27 | 1986-10-27 | Haessle Ab | Novel compunds |
| NZ234564A (en) | 1986-11-21 | 1991-04-26 | Haessle Ab | 1-substituted benzimidazoles and pharmaceutical compositions |
| SE8604998D0 (sv) | 1986-11-21 | 1986-11-21 | Haessle Ab | Novel pharmacological compounds |
| WO1989005643A1 (en) * | 1987-12-18 | 1989-06-29 | Pfizer Inc. | Heterocyclic-substituted quinoline-carboxylic acids |
| JPH021280U (en, 2012) * | 1988-06-14 | 1990-01-08 | ||
| EP0436025A4 (en) * | 1988-09-20 | 1991-09-11 | Hisamitsu Pharmaceutical Co. Inc. | Novel dibenz b,e)oxepin derivatives |
| IE64199B1 (en) * | 1988-12-22 | 1995-07-12 | Haessle Ab | Compound with gastric acid inhibitory effect and process for its preparation |
| SE8804628D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New compounds |
| SE8804629D0 (sv) | 1988-12-22 | 1988-12-22 | Ab Haessle | New therapeutically active compounds |
| JP2679745B2 (ja) * | 1989-06-29 | 1997-11-19 | 明治製菓株式会社 | アゾール誘導体及びそれらを有効成分とする抗潰瘍剤 |
| JPH0347053U (en, 2012) * | 1989-09-16 | 1991-04-30 | ||
| US5274099A (en) * | 1989-12-20 | 1993-12-28 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| US4965269A (en) * | 1989-12-20 | 1990-10-23 | Ab Hassle | Therapeutically active chloro substituted benzimidazoles |
| US5049674A (en) * | 1989-12-20 | 1991-09-17 | Aktiebolaget Hassle | Therapeutically active fluoro substituted benzimidazoles |
| SE9002206D0 (sv) | 1990-06-20 | 1990-06-20 | Haessle Ab | New compounds |
| RO117792B1 (ro) * | 1994-06-10 | 2002-07-30 | Byk Gulden Lomberg Chem Fab | Arilalchiltioalchil-tiopiridine substituite, utilizate pentru combaterea bacteriilor helicobacter |
| SI20974A (sl) * | 1999-08-26 | 2003-02-28 | Aaipharma, Inc. | Alkoksi substituirane benzimidazolne spojine, farmacevtski pripravki, ki jih vsebujejo ter metode za njihovo uporabo |
| WO2003080607A1 (en) * | 2002-03-27 | 2003-10-02 | Altana Pharma Ag | Novel alkoxypyridine-derivatives |
| HRP20050799A8 (en) * | 2003-02-25 | 2007-10-31 | Altana Pharma Ag | Imidazo[4,5-b]quinoline-derivatives and their use as no-synthase inhibitors |
| JP2007507466A (ja) | 2003-10-01 | 2007-03-29 | アルタナ ファルマ アクチエンゲゼルシャフト | 誘導性ｎｏシンターゼ阻害剤としてのイミダゾピリジン誘導体 |
| CA2540230A1 (en) * | 2003-10-01 | 2005-07-07 | Altana Pharma Ag | Aminopyridine-derivatives as inductible no-synthase inhibitors |
| WO2005030771A1 (en) * | 2003-10-01 | 2005-04-07 | Altana Pharma Ag | Imidazopyridine-derivatives as inductible no-synthase inhibitors |
| CA2540242A1 (en) * | 2003-10-01 | 2005-04-07 | Altana Pharma Ag | Imidazopyridine-derivatives as inducible no-synthase inhibitors |
| AU2004276012A1 (en) | 2003-10-01 | 2005-04-07 | Altana Pharma Ag | Imidazo(4,5-b)pyridine-derivatives as inducible no-synthase inhibitors |
| MX2008011594A (es) * | 2006-03-10 | 2008-09-22 | Arigen Pharmaceuticals Inc | Derivado de piridina novedoso que tiene actividad anti-helicobacter pylori. |
| EP2070923A1 (de) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Insektizide Iminoheterocyclen |
| NZ705135A (en) * | 2010-05-26 | 2017-10-27 | Sunovion Pharmaceuticals Inc | Heteroaryl compounds and methods of use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1234058A (en, 2012) * | 1968-10-21 | 1971-06-03 |
-
1974
- 1974-02-18 SE SE7402101A patent/SE418966B/xx not_active IP Right Cessation
-
1975
- 1975-01-27 ZA ZA00750558A patent/ZA75558B/xx unknown
- 1975-02-01 DE DE19752504252 patent/DE2504252A1/de active Granted
- 1975-02-14 AU AU78206/75A patent/AU499639B2/en not_active Expired
- 1975-02-14 SU SU752106386A patent/SU795476A3/ru active
- 1975-02-14 DD DD184221A patent/DD119422A5/xx unknown
- 1975-02-14 CS CS75987A patent/CS194715B2/cs unknown
- 1975-02-14 DK DK54075AA patent/DK141122B/da not_active IP Right Cessation
- 1975-02-14 CH CH182975A patent/CH616160A5/de not_active IP Right Cessation
- 1975-02-14 FI FI750421A patent/FI59590C/fi not_active IP Right Cessation
- 1975-02-17 FR FR7504888A patent/FR2261007B1/fr not_active Expired
- 1975-02-17 CA CA220,235A patent/CA1060448A/en not_active Expired
- 1975-02-17 IE IE307/75A patent/IE40858B1/xx unknown
- 1975-02-17 HU HU75HE00000679A patent/HU172141B/hu unknown
- 1975-02-17 AT AT113775A patent/AT343659B/de not_active IP Right Cessation
- 1975-02-18 BE BE153453A patent/BE825655A/xx not_active IP Right Cessation
- 1975-02-18 NL NL7501917A patent/NL7501917A/xx not_active Application Discontinuation
- 1975-02-18 NO NO750541A patent/NO142401C/no unknown
- 1975-02-18 JP JP50020284A patent/JPS5924157B2/ja not_active Expired
- 1975-02-18 LU LU71872A patent/LU71872A1/xx unknown
- 1975-02-18 GB GB6869/75A patent/GB1500043A/en not_active Expired
-
1980
- 1980-11-27 HK HK670/80A patent/HK67080A/xx unknown
-
1981
- 1981-12-30 MY MY208/81A patent/MY8100208A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |