FI63756C - Foerfarande foer framstaellning av 2-(2-pyridylmetylsulfinyl)-bensimidazolderivat med magsyrasekretionsinhiberande verkan - Google Patents
Foerfarande foer framstaellning av 2-(2-pyridylmetylsulfinyl)-bensimidazolderivat med magsyrasekretionsinhiberande verkan Download PDFInfo
- Publication number
- FI63756C FI63756C FI752327A FI752327A FI63756C FI 63756 C FI63756 C FI 63756C FI 752327 A FI752327 A FI 752327A FI 752327 A FI752327 A FI 752327A FI 63756 C FI63756 C FI 63756C
- Authority
- FI
- Finland
- Prior art keywords
- pyridyl
- het
- alkyl
- methyl
- compound
- Prior art date
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- -1 2-PYRIDYLMETHYLSULPHINYL Chemical class 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
- 125000004076 pyridyl group Chemical group 0.000 description 30
- 239000000203 mixture Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 108010079943 Pentagastrin Proteins 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- ALXRNCVIQSDJAO-KRCBVYEFSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCNC(=O)OCC(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ALXRNCVIQSDJAO-KRCBVYEFSA-N 0.000 description 12
- 229960000444 pentagastrin Drugs 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 230000027119 gastric acid secretion Effects 0.000 description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 10
- 230000028327 secretion Effects 0.000 description 9
- PLITYYGQMDTHMM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1SCC1=CC=CC=N1 PLITYYGQMDTHMM-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 230000033228 biological regulation Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 241000277284 Salvelinus fontinalis Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 210000004211 gastric acid Anatomy 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000000638 stimulation Effects 0.000 description 4
- 241000282465 Canis Species 0.000 description 3
- 241000009328 Perro Species 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 206010061592 cardiac fibrillation Diseases 0.000 description 3
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000002600 fibrillogenic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000003248 secreting effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- SPMLMLQATWNZEE-UHFFFAOYSA-N 2-(chloromethyl)-1h-benzimidazole Chemical compound C1=CC=C2NC(CCl)=NC2=C1 SPMLMLQATWNZEE-UHFFFAOYSA-N 0.000 description 2
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 2
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 2
- YKWXFZQLRBOOCV-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)-1h-benzimidazole;hydrochloride Chemical compound Cl.N=1C2=CC=CC=C2NC=1SCC1=CC=CC=N1 YKWXFZQLRBOOCV-UHFFFAOYSA-N 0.000 description 2
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- UDQCDDZBBZNIFA-UHFFFAOYSA-N 4-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=CC2=C1NC(=S)N2 UDQCDDZBBZNIFA-UHFFFAOYSA-N 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical class [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229920003091 Methocel™ Polymers 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- RYXPMWYHEBGTRV-UHFFFAOYSA-N Omeprazole sodium Chemical compound [Na+].N=1C2=CC(OC)=CC=C2[N-]C=1S(=O)CC1=NC=C(C)C(OC)=C1C RYXPMWYHEBGTRV-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 2
- FVJIUYMDPPZODN-UHFFFAOYSA-N [Br].C1CC2C(=[N+]=[N-])CC1CC2 Chemical compound [Br].C1CC2C(=[N+]=[N-])CC1CC2 FVJIUYMDPPZODN-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 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 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-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
- 125000004178 (C1-C4) alkyl group Chemical group 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
- 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
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- TVQYQJPNAAFHDF-UHFFFAOYSA-N 1-methylsulfinylbenzimidazole Chemical compound C1=CC=C2N(S(=O)C)C=NC2=C1 TVQYQJPNAAFHDF-UHFFFAOYSA-N 0.000 description 1
- WGFGBWGHRDUSFJ-UHFFFAOYSA-N 2-(pyridin-3-ylmethylsulfanyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1SCC1=CC=CN=C1 WGFGBWGHRDUSFJ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
- 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
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 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
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 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
- UZHDGDDPOPDJGM-UHFFFAOYSA-N Stigmatellin A Natural products COC1=CC(OC)=C2C(=O)C(C)=C(CCC(C)C(OC)C(C)C(C=CC=CC(C)=CC)OC)OC2=C1O UZHDGDDPOPDJGM-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- NOJZFGZMTUAHLD-UHFFFAOYSA-N [Li].[Cl] Chemical compound [Li].[Cl] NOJZFGZMTUAHLD-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SPDVQSDBSYUSIC-UHFFFAOYSA-N n-methyl-2-(pyridin-2-ylmethylsulfanyl)-1h-benzimidazole-4-carboxamide Chemical compound N1C=2C(C(=O)NC)=CC=CC=2N=C1SCC1=CC=CC=N1 SPDVQSDBSYUSIC-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 150000007524 organic acids Chemical class 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
- 150000002976 peresters Chemical class 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 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
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- PEEXCRJDFUVJRT-UHFFFAOYSA-M potassium;methoxymethanedithioate Chemical compound [K+].COC([S-])=S PEEXCRJDFUVJRT-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 229960000953 salsalate Drugs 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
-
- 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
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7406513A SE416649B (sv) | 1974-05-16 | 1974-05-16 | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| NO75752851A NO143222C (no) | 1974-05-16 | 1975-08-15 | Analogifremgangsmaate for fremstilling av nye substituerte pyridylsulfinyl-benzimidazoler med terapeutisk aktivitet |
| FI752327A FI63756C (fi) | 1974-05-16 | 1975-08-15 | Foerfarande foer framstaellning av 2-(2-pyridylmetylsulfinyl)-bensimidazolderivat med magsyrasekretionsinhiberande verkan |
| DK372175AA DK140840B (da) | 1974-05-16 | 1975-08-18 | Analogifremgangsmåde til fremstilling af benzimidazolderivater eller syreadditionssalte deraf. |
| GB43039/75A GB1525958A (en) | 1974-05-16 | 1975-10-20 | 2-(heterocyclic substituted alkylsulphinyl)-benzimidazoles and their pharmaceutical compositions |
| CY1125A CY1125A (en) | 1974-05-16 | 1975-10-20 | 2-(heterocaclic asbstituted alkylsulphinyl)-benzinmidazoles and their pharmaceutical compositions |
| ZA00756600A ZA756600B (en) | 1974-05-16 | 1975-10-20 | Gastric acid secretion agents |
| IE2313/75A IE42451B1 (en) | 1974-05-16 | 1975-10-23 | 2-(heterocyclic substituted alkylsulphinyl)-benzimidazoles and their pharmaceutical compositions |
| DE19752548340 DE2548340A1 (de) | 1974-05-16 | 1975-10-29 | Benzimidazole, verfahren zu deren herstellung und sie enthaltende mittel |
| AT838075A AT337697B (de) | 1974-05-16 | 1975-11-04 | Verfahren zur herstellung von neuen benzimidazolderivaten und ihren salzen |
| CS757458A CS196289B2 (en) | 1974-05-16 | 1975-11-05 | Process for preparing new compounds |
| NL7513141A NL7513141A (nl) | 1974-05-16 | 1975-11-10 | Benzimidazoolderivaten en werkwijze voor het be- reiden daarvan alsmede preparaten voor het bein- vloeden van de maagzuursecretie. |
| US05/630,916 US4045563A (en) | 1974-05-16 | 1975-11-11 | Substituted 2-[pyridylalkylenesulfinyl]-benzimidazoles with gastric acid secretion inhibiting effects |
| HU75HE00000696A HU172653B (hu) | 1974-05-16 | 1975-11-12 | Sposob poluchenija zamehhennykh 2-skobka-2-piridil-metil-sul'finil-skobka zakryta-benzimidazolov |
| SU752189960A SU602118A3 (ru) | 1974-05-16 | 1975-11-13 | Способ получени производных бензимидазола или их солей |
| CA239,643A CA1055033A (en) | 1974-05-16 | 1975-11-14 | 2-(2-heterocyclic-methylsulphinyl)-benzimidazole compounds |
| CH1481475A CH623814A5 (en) | 1974-05-16 | 1975-11-14 | Process for the preparation of novel benzimidazoles |
| DD189463A DD122534A5 (ref) | 1974-05-16 | 1975-11-14 | |
| FR7534910A FR2331340A1 (fr) | 1974-05-16 | 1975-11-14 | Nouveaux derives du benzimidazole, procede pour leur obtention et compositions pharmaceutiques les contenant |
| JP50137712A JPS5262275A (en) | 1974-05-16 | 1975-11-15 | Production of organic compound |
| FR7616732A FR2392021A1 (fr) | 1974-05-16 | 1976-06-03 | Nouveaux derives du benzimidazole et procede pour leur obtention |
| AT752276A AT351524B (de) | 1974-05-16 | 1976-10-11 | Verfahren zur herstellung von neuen benzimida- zolderivaten, ihren salzen und optischen isomeren |
| DK783659A DK365978A (da) | 1974-05-16 | 1978-08-18 | Mellemprodukt til anvendelse ved fremstilling af benzimidazolderivater |
| CS786886A CS196290B2 (en) | 1974-05-16 | 1978-10-23 | Process for preparing new compounds |
| CH976079A CH623582A5 (en) | 1974-05-16 | 1979-10-31 | Process for the preparation of benzimidazoles |
| FI811747A FI65617C (fi) | 1974-05-16 | 1981-06-04 | Mellanprodukt foer framstaellning av magsyrasekretionsinhiberande 2-(2-pyridylmetylsulfinyl)-benzimidazolderivat |
| HK87/82A HK8782A (en) | 1974-05-16 | 1982-02-25 | 2-(heterocyclic substituted alkylsulphinyl)-benzimidazoles and their pharmaceutical compositions |
| MY159/82A MY8200159A (en) | 1974-05-16 | 1982-12-30 | 2-[heterocylic substituted alkylsulphinyl]-benzimidazoles and their pharmaceutical compositions |
Applications Claiming Priority (50)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7406513 | 1974-05-16 | ||
| SE7406513A SE416649B (sv) | 1974-05-16 | 1974-05-16 | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| NO752851 | 1975-08-15 | ||
| NO75752851A NO143222C (no) | 1974-05-16 | 1975-08-15 | Analogifremgangsmaate for fremstilling av nye substituerte pyridylsulfinyl-benzimidazoler med terapeutisk aktivitet |
| FI752327A FI63756C (fi) | 1974-05-16 | 1975-08-15 | Foerfarande foer framstaellning av 2-(2-pyridylmetylsulfinyl)-bensimidazolderivat med magsyrasekretionsinhiberande verkan |
| FI752327 | 1975-08-15 | ||
| DK372175 | 1975-08-18 | ||
| DK372175AA DK140840B (da) | 1974-05-16 | 1975-08-18 | Analogifremgangsmåde til fremstilling af benzimidazolderivater eller syreadditionssalte deraf. |
| GB43039/75A GB1525958A (en) | 1974-05-16 | 1975-10-20 | 2-(heterocyclic substituted alkylsulphinyl)-benzimidazoles and their pharmaceutical compositions |
| ZA7506600 | 1975-10-20 | ||
| GB4303975 | 1975-10-20 | ||
| ZA00756600A ZA756600B (en) | 1974-05-16 | 1975-10-20 | Gastric acid secretion agents |
| IE2313/75A IE42451B1 (en) | 1974-05-16 | 1975-10-23 | 2-(heterocyclic substituted alkylsulphinyl)-benzimidazoles and their pharmaceutical compositions |
| IE231375 | 1975-10-23 | ||
| DE2548340 | 1975-10-29 | ||
| DE19752548340 DE2548340A1 (de) | 1974-05-16 | 1975-10-29 | Benzimidazole, verfahren zu deren herstellung und sie enthaltende mittel |
| AT838075 | 1975-11-04 | ||
| AT838075A AT337697B (de) | 1974-05-16 | 1975-11-04 | Verfahren zur herstellung von neuen benzimidazolderivaten und ihren salzen |
| CS757458A CS196289B2 (en) | 1974-05-16 | 1975-11-05 | Process for preparing new compounds |
| CS745875 | 1975-11-05 | ||
| NL7513141A NL7513141A (nl) | 1974-05-16 | 1975-11-10 | Benzimidazoolderivaten en werkwijze voor het be- reiden daarvan alsmede preparaten voor het bein- vloeden van de maagzuursecretie. |
| NL7513141 | 1975-11-10 | ||
| US63091675 | 1975-11-11 | ||
| US05/630,916 US4045563A (en) | 1974-05-16 | 1975-11-11 | Substituted 2-[pyridylalkylenesulfinyl]-benzimidazoles with gastric acid secretion inhibiting effects |
| HUHE000696 | 1975-11-12 | ||
| HU75HE00000696A HU172653B (hu) | 1974-05-16 | 1975-11-12 | Sposob poluchenija zamehhennykh 2-skobka-2-piridil-metil-sul'finil-skobka zakryta-benzimidazolov |
| SU752189960A SU602118A3 (ru) | 1974-05-16 | 1975-11-13 | Способ получени производных бензимидазола или их солей |
| SU2189960 | 1975-11-13 | ||
| CA239643 | 1975-11-14 | ||
| CH1481475 | 1975-11-14 | ||
| DD189463A DD122534A5 (ref) | 1974-05-16 | 1975-11-14 | |
| CH1481475A CH623814A5 (en) | 1974-05-16 | 1975-11-14 | Process for the preparation of novel benzimidazoles |
| FR7534910 | 1975-11-14 | ||
| CA239,643A CA1055033A (en) | 1974-05-16 | 1975-11-14 | 2-(2-heterocyclic-methylsulphinyl)-benzimidazole compounds |
| FR7534910A FR2331340A1 (fr) | 1974-05-16 | 1975-11-14 | Nouveaux derives du benzimidazole, procede pour leur obtention et compositions pharmaceutiques les contenant |
| DD18946375 | 1975-11-14 | ||
| JP50137712A JPS5262275A (en) | 1974-05-16 | 1975-11-15 | Production of organic compound |
| JP13771275 | 1975-11-15 | ||
| FR7616732 | 1976-06-03 | ||
| FR7616732A FR2392021A1 (fr) | 1974-05-16 | 1976-06-03 | Nouveaux derives du benzimidazole et procede pour leur obtention |
| AT752276 | 1976-10-11 | ||
| AT752276A AT351524B (de) | 1974-05-16 | 1976-10-11 | Verfahren zur herstellung von neuen benzimida- zolderivaten, ihren salzen und optischen isomeren |
| DK783659A DK365978A (da) | 1974-05-16 | 1978-08-18 | Mellemprodukt til anvendelse ved fremstilling af benzimidazolderivater |
| DK365978 | 1978-08-18 | ||
| CS688678 | 1978-10-23 | ||
| CS786886A CS196290B2 (en) | 1974-05-16 | 1978-10-23 | Process for preparing new compounds |
| HU8782 | 1982-02-25 | ||
| HU8782 | 1982-02-25 | ||
| MY159/82A MY8200159A (en) | 1974-05-16 | 1982-12-30 | 2-[heterocylic substituted alkylsulphinyl]-benzimidazoles and their pharmaceutical compositions |
| MY8200159 | 1982-12-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI752327A7 FI752327A7 (ref) | 1977-02-16 |
| FI63756B FI63756B (fi) | 1983-04-29 |
| FI63756C true FI63756C (fi) | 1983-08-10 |
Family
ID=40486266
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI752327A FI63756C (fi) | 1974-05-16 | 1975-08-15 | Foerfarande foer framstaellning av 2-(2-pyridylmetylsulfinyl)-bensimidazolderivat med magsyrasekretionsinhiberande verkan |
| FI811747A FI65617C (fi) | 1974-05-16 | 1981-06-04 | Mellanprodukt foer framstaellning av magsyrasekretionsinhiberande 2-(2-pyridylmetylsulfinyl)-benzimidazolderivat |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI811747A FI65617C (fi) | 1974-05-16 | 1981-06-04 | Mellanprodukt foer framstaellning av magsyrasekretionsinhiberande 2-(2-pyridylmetylsulfinyl)-benzimidazolderivat |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4045563A (ref) |
| JP (1) | JPS5262275A (ref) |
| AT (2) | AT337697B (ref) |
| CA (1) | CA1055033A (ref) |
| CH (2) | CH623814A5 (ref) |
| CS (2) | CS196289B2 (ref) |
| CY (1) | CY1125A (ref) |
| DD (1) | DD122534A5 (ref) |
| DE (1) | DE2548340A1 (ref) |
| DK (2) | DK140840B (ref) |
| FI (2) | FI63756C (ref) |
| FR (2) | FR2331340A1 (ref) |
| GB (1) | GB1525958A (ref) |
| HK (1) | HK8782A (ref) |
| HU (1) | HU172653B (ref) |
| IE (1) | IE42451B1 (ref) |
| MY (1) | MY8200159A (ref) |
| NL (1) | NL7513141A (ref) |
| NO (1) | NO143222C (ref) |
| SE (1) | SE416649B (ref) |
| SU (1) | SU602118A3 (ref) |
| ZA (1) | ZA756600B (ref) |
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| JP2025532389A (ja) | 2022-10-04 | 2025-09-29 | ザビリュク，アルセニー | 大動脈弁の石灰化の抑制 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1234058A (ref) * | 1968-10-21 | 1971-06-03 | ||
| DE1903755B2 (de) * | 1969-01-25 | 1971-04-22 | Th Goldschmidt AG, 4300 Essen | Verfahren zur herstellung von zinnhaltigen keramischen farbkoerpern |
| SE418966B (sv) * | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
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1974
- 1974-05-16 SE SE7406513A patent/SE416649B/xx not_active IP Right Cessation
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1975
- 1975-08-15 FI FI752327A patent/FI63756C/fi not_active IP Right Cessation
- 1975-08-15 NO NO75752851A patent/NO143222C/no unknown
- 1975-08-18 DK DK372175AA patent/DK140840B/da not_active IP Right Cessation
- 1975-10-20 ZA ZA00756600A patent/ZA756600B/xx unknown
- 1975-10-20 CY CY1125A patent/CY1125A/xx unknown
- 1975-10-20 GB GB43039/75A patent/GB1525958A/en not_active Expired
- 1975-10-23 IE IE2313/75A patent/IE42451B1/en unknown
- 1975-10-29 DE DE19752548340 patent/DE2548340A1/de active Granted
- 1975-11-04 AT AT838075A patent/AT337697B/de not_active IP Right Cessation
- 1975-11-05 CS CS757458A patent/CS196289B2/cs unknown
- 1975-11-10 NL NL7513141A patent/NL7513141A/xx not_active Application Discontinuation
- 1975-11-11 US US05/630,916 patent/US4045563A/en not_active Expired - Lifetime
- 1975-11-12 HU HU75HE00000696A patent/HU172653B/hu unknown
- 1975-11-13 SU SU752189960A patent/SU602118A3/ru active
- 1975-11-14 CA CA239,643A patent/CA1055033A/en not_active Expired
- 1975-11-14 DD DD189463A patent/DD122534A5/xx unknown
- 1975-11-14 FR FR7534910A patent/FR2331340A1/fr active Granted
- 1975-11-14 CH CH1481475A patent/CH623814A5/de not_active IP Right Cessation
- 1975-11-15 JP JP50137712A patent/JPS5262275A/ja active Granted
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1976
- 1976-06-03 FR FR7616732A patent/FR2392021A1/fr active Granted
- 1976-10-11 AT AT752276A patent/AT351524B/de not_active IP Right Cessation
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1978
- 1978-08-18 DK DK783659A patent/DK365978A/da unknown
- 1978-10-23 CS CS786886A patent/CS196290B2/cs unknown
-
1979
- 1979-10-31 CH CH976079A patent/CH623582A5/de not_active IP Right Cessation
-
1981
- 1981-06-04 FI FI811747A patent/FI65617C/fi not_active IP Right Cessation
-
1982
- 1982-02-25 HK HK87/82A patent/HK8782A/xx unknown
- 1982-12-30 MY MY159/82A patent/MY8200159A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: AB HAESSLE |