HU192875B - Process for preparing 2-pyridinethiol derivatives - Google Patents
Process for preparing 2-pyridinethiol derivatives Download PDFInfo
- Publication number
- HU192875B HU192875B HU843775A HU377584A HU192875B HU 192875 B HU192875 B HU 192875B HU 843775 A HU843775 A HU 843775A HU 377584 A HU377584 A HU 377584A HU 192875 B HU192875 B HU 192875B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- acid addition
- acid
- pyridine
- addition salt
- Prior art date
Links
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- -1 thiol compound Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000005749 2-halopyridines Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 210000002784 stomach Anatomy 0.000 description 12
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 11
- 208000025865 Ulcer Diseases 0.000 description 11
- 229960000905 indomethacin Drugs 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 231100000397 ulcer Toxicity 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 230000002496 gastric effect Effects 0.000 description 8
- 125000004149 thio group Chemical group *S* 0.000 description 8
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 7
- 229960001138 acetylsalicylic acid Drugs 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 230000001120 cytoprotective effect Effects 0.000 description 5
- 230000027119 gastric acid secretion Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 206010022714 Intestinal ulcer Diseases 0.000 description 4
- 208000007107 Stomach Ulcer Diseases 0.000 description 4
- 208000010513 Stupor Diseases 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 229960003151 mercaptamine Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 101100352919 Caenorhabditis elegans ppm-2 gene Proteins 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 3
- 229960001380 cimetidine Drugs 0.000 description 3
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- KKJGMDXUAOTRBW-UHFFFAOYSA-N (2-chloropyridin-3-yl)-phenylmethanone Chemical compound ClC1=NC=CC=C1C(=O)C1=CC=CC=C1 KKJGMDXUAOTRBW-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 201000005917 gastric ulcer Diseases 0.000 description 2
- 230000000762 glandular Effects 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 238000010972 statistical evaluation Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YHQLGHPOXKUKSX-UHFFFAOYSA-N (2-chloropyridin-3-yl)-(2,5-dimethylphenyl)methanone Chemical compound CC1=CC=C(C)C(C(=O)C=2C(=NC=CC=2)Cl)=C1 YHQLGHPOXKUKSX-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- FOQYDURHXZVLFT-UHFFFAOYSA-N 2-phenyl-2-pyridin-2-ylethanethioamide Chemical compound C=1C=CC=NC=1C(C(=S)N)C1=CC=CC=C1 FOQYDURHXZVLFT-UHFFFAOYSA-N 0.000 description 1
- AIMIAJHGOMWBQG-UHFFFAOYSA-N 3-methyl-5,6,7,8-tetrahydroquinoline-8-carbothioamide Chemical compound NC(=S)C1CCCC2=CC(C)=CN=C21 AIMIAJHGOMWBQG-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010053155 Epigastric discomfort Diseases 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010029897 Obsessive thoughts Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 229940067131 aspirin 100 mg Drugs 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- OGLIEZKGUPAGHK-UHFFFAOYSA-N phenyl-(2-sulfanylidene-1h-pyridin-3-yl)methanone Chemical compound C=1C=CNC(=S)C=1C(=O)C1=CC=CC=C1 OGLIEZKGUPAGHK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
- 229960004633 pirenzepine Drugs 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU843775A HU192875B (en) | 1984-10-05 | 1984-10-05 | Process for preparing 2-pyridinethiol derivatives |
| PH32832A PH21435A (en) | 1984-10-05 | 1985-09-24 | 2-pyridine-thiol derivatives and pharmaceutical compositions containing them |
| US06/783,875 US4713388A (en) | 1984-10-05 | 1985-10-03 | Certain 3- or 4-benzoyl-2-[(2-aminoethyl)thio-pyridines] and their anti-ulcer properties |
| GR852409A GR852409B (enExample) | 1984-10-05 | 1985-10-04 | |
| AU48328/85A AU579665B2 (en) | 1984-10-05 | 1985-10-04 | 2-pyridine-thiol derivatives |
| EP85112599A EP0177907B1 (de) | 1984-10-05 | 1985-10-04 | Neue 2-Pyridin-thiol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
| NO853935A NO853935L (no) | 1984-10-05 | 1985-10-04 | Fremgangsm¨te ved fremstilling av 2-pyridin-thiolderivater |
| YU01583/85A YU158385A (en) | 1984-10-05 | 1985-10-04 | Process for obtaining derivatives of 2-pyridine thioles |
| IL76577A IL76577A0 (en) | 1984-10-05 | 1985-10-04 | 2-pyridine-thiol derivatives,their preparation and pharmaceutical compositions containing them |
| CN198585107284A CN85107284A (zh) | 1984-10-05 | 1985-10-04 | 制备2-吡啶硫醇类衍生物和含有它们的药物配方的方法 |
| IN778/MAS/85A IN162570B (enExample) | 1984-10-05 | 1985-10-04 | |
| DE8585112599T DE3563048D1 (en) | 1984-10-05 | 1985-10-04 | 2-pyridine-thiol derivatives, processes for their preparation and pharmaceutical compositions containing them |
| AT85112599T ATE34739T1 (de) | 1984-10-05 | 1985-10-04 | Neue 2-pyridin-thiol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate. |
| DD85281464A DD238384A5 (de) | 1984-10-05 | 1985-10-04 | Verfahren zur herstellung von neuen 2-pyridin-thiol-derivaten |
| ZA857676A ZA857676B (en) | 1984-10-05 | 1985-10-04 | 2-pyridine-thiol derivatives,process for their preparation and pharmaceutical compositions containing them |
| DK455285A DK455285A (da) | 1984-10-05 | 1985-10-04 | 2-pyridin-thiolderivater |
| PT81255A PT81255B (en) | 1984-10-05 | 1985-10-04 | Process for the preparation of 2-pyridine-thiol derivatives and pharmaceutical compositions containing them |
| JP60221714A JPS6191172A (ja) | 1984-10-05 | 1985-10-04 | ２‐ピリジン‐チオール誘導体、その製造方法およびそれを含有する医薬組成物 |
| FI853866A FI853866A7 (fi) | 1984-10-05 | 1985-10-04 | 2-pyridiini-tioli-johdannaiset, menetelmäniiden valmistamiseksi ja niitä sisältävät farmaseuttiset yhdisteet. |
| ES547604A ES8704460A1 (es) | 1984-10-05 | 1985-10-04 | Un procedimiento para preparar derivados de 2-piridin-tiol |
| PL1985255643A PL146371B1 (en) | 1984-10-05 | 1985-10-04 | Method of obtaining 2-pyridinothiole derivatives |
| SU853959903A SU1346042A3 (ru) | 1984-10-05 | 1985-10-04 | Способ получени производных 2-пиридин-тиола или их кислотно-аддитивных солей (его варианты) |
| KR1019850007352A KR860003212A (ko) | 1984-10-05 | 1985-10-05 | 2-피리딘-티올 유도체 및 그의 산부가염의 제조 방법 |
| US06/912,999 US4691017A (en) | 1984-10-05 | 1986-09-26 | 2-hydroxy-and 2-halo-ethylthiopyridine intermediates for preparing antiulcer compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU843775A HU192875B (en) | 1984-10-05 | 1984-10-05 | Process for preparing 2-pyridinethiol derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT38907A HUT38907A (en) | 1986-07-28 |
| HU192875B true HU192875B (en) | 1987-07-28 |
Family
ID=10965437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU843775A HU192875B (en) | 1984-10-05 | 1984-10-05 | Process for preparing 2-pyridinethiol derivatives |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4713388A (enExample) |
| EP (1) | EP0177907B1 (enExample) |
| JP (1) | JPS6191172A (enExample) |
| KR (1) | KR860003212A (enExample) |
| CN (1) | CN85107284A (enExample) |
| AT (1) | ATE34739T1 (enExample) |
| AU (1) | AU579665B2 (enExample) |
| DD (1) | DD238384A5 (enExample) |
| DE (1) | DE3563048D1 (enExample) |
| DK (1) | DK455285A (enExample) |
| ES (1) | ES8704460A1 (enExample) |
| FI (1) | FI853866A7 (enExample) |
| GR (1) | GR852409B (enExample) |
| HU (1) | HU192875B (enExample) |
| IL (1) | IL76577A0 (enExample) |
| IN (1) | IN162570B (enExample) |
| NO (1) | NO853935L (enExample) |
| PH (1) | PH21435A (enExample) |
| PL (1) | PL146371B1 (enExample) |
| PT (1) | PT81255B (enExample) |
| SU (1) | SU1346042A3 (enExample) |
| YU (1) | YU158385A (enExample) |
| ZA (1) | ZA857676B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1339423C (en) * | 1988-09-14 | 1997-09-02 | Yuji Ono | Pyridine compounds and pharmaceutical use thereof |
| DE69209576T4 (de) * | 1991-05-10 | 1997-01-30 | Takeda Chemical Industries Ltd | Pyridinderivate, deren Herstellung und Anwendung |
| JP4608140B2 (ja) * | 2000-07-05 | 2011-01-05 | 石原産業株式会社 | ベンゾイルピリジン誘導体またはその塩、それらを有効成分として含有する殺菌剤、それらの製造方法ならびにそれらを製造するための中間体 |
| AR029289A1 (es) | 2000-07-05 | 2003-06-18 | Ishihara Sangyo Kaisha | Derivado de benzoilpiridina o su sal, fungicida que lo contiene como un ingrediente activo, su proceso de produccion e intermediario para producirlo |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| JP4886511B2 (ja) | 2003-07-30 | 2012-02-29 | ライジェル ファーマシューティカルズ， インコーポレイテッド | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療または予防方法 |
| US7585883B2 (en) * | 2004-10-29 | 2009-09-08 | Rigel Pharmaceuticals, Inc. | Substituted pyridines and their uses |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT238200B (de) * | 1962-03-27 | 1965-01-25 | Degussa | Verfahren zur Herstellung von neuen Pyridinderivaten |
| JPS552920A (en) * | 1978-06-23 | 1980-01-10 | Natl Res Inst For Metals | Method of detecting surface dfect of non-magnetic material |
| US4304781A (en) * | 1978-11-30 | 1981-12-08 | John Wyeth & Brother Limited | Treatment of ulcers and hypertension |
| HU194830B (en) * | 1984-10-05 | 1988-03-28 | Richter Gedeon Vegyeszet | Process for the production of derivatives of piridine |
-
1984
- 1984-10-05 HU HU843775A patent/HU192875B/hu not_active IP Right Cessation
-
1985
- 1985-09-24 PH PH32832A patent/PH21435A/en unknown
- 1985-10-03 US US06/783,875 patent/US4713388A/en not_active Expired - Fee Related
- 1985-10-04 ES ES547604A patent/ES8704460A1/es not_active Expired
- 1985-10-04 AT AT85112599T patent/ATE34739T1/de not_active IP Right Cessation
- 1985-10-04 IN IN778/MAS/85A patent/IN162570B/en unknown
- 1985-10-04 PL PL1985255643A patent/PL146371B1/pl unknown
- 1985-10-04 SU SU853959903A patent/SU1346042A3/ru active
- 1985-10-04 EP EP85112599A patent/EP0177907B1/de not_active Expired
- 1985-10-04 IL IL76577A patent/IL76577A0/xx unknown
- 1985-10-04 PT PT81255A patent/PT81255B/pt unknown
- 1985-10-04 ZA ZA857676A patent/ZA857676B/xx unknown
- 1985-10-04 YU YU01583/85A patent/YU158385A/xx unknown
- 1985-10-04 NO NO853935A patent/NO853935L/no unknown
- 1985-10-04 CN CN198585107284A patent/CN85107284A/zh active Pending
- 1985-10-04 DE DE8585112599T patent/DE3563048D1/de not_active Expired
- 1985-10-04 JP JP60221714A patent/JPS6191172A/ja active Pending
- 1985-10-04 GR GR852409A patent/GR852409B/el unknown
- 1985-10-04 AU AU48328/85A patent/AU579665B2/en not_active Expired - Fee Related
- 1985-10-04 DK DK455285A patent/DK455285A/da not_active Application Discontinuation
- 1985-10-04 DD DD85281464A patent/DD238384A5/de unknown
- 1985-10-04 FI FI853866A patent/FI853866A7/fi not_active Application Discontinuation
- 1985-10-05 KR KR1019850007352A patent/KR860003212A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE3563048D1 (en) | 1988-07-07 |
| KR860003212A (ko) | 1986-05-21 |
| DD238384A5 (de) | 1986-08-20 |
| ES547604A0 (es) | 1987-04-01 |
| ES8704460A1 (es) | 1987-04-01 |
| PT81255A (en) | 1985-11-01 |
| US4713388A (en) | 1987-12-15 |
| PT81255B (en) | 1987-03-23 |
| AU4832885A (en) | 1986-04-10 |
| ATE34739T1 (de) | 1988-06-15 |
| ZA857676B (en) | 1986-06-25 |
| PH21435A (en) | 1987-10-15 |
| DK455285A (da) | 1986-04-06 |
| EP0177907A1 (de) | 1986-04-16 |
| IL76577A0 (en) | 1986-02-28 |
| GR852409B (enExample) | 1986-02-04 |
| PL255643A1 (en) | 1987-01-12 |
| HUT38907A (en) | 1986-07-28 |
| NO853935L (no) | 1986-04-07 |
| FI853866L (fi) | 1986-04-06 |
| FI853866A0 (fi) | 1985-10-04 |
| AU579665B2 (en) | 1988-12-01 |
| DK455285D0 (da) | 1985-10-04 |
| SU1346042A3 (ru) | 1987-10-15 |
| PL146371B1 (en) | 1989-01-31 |
| FI853866A7 (fi) | 1986-04-06 |
| IN162570B (enExample) | 1988-06-11 |
| JPS6191172A (ja) | 1986-05-09 |
| YU158385A (en) | 1988-04-30 |
| CN85107284A (zh) | 1986-06-10 |
| EP0177907B1 (de) | 1988-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |