CN85107284A - 制备2-吡啶硫醇类衍生物和含有它们的药物配方的方法 - Google Patents
制备2-吡啶硫醇类衍生物和含有它们的药物配方的方法 Download PDFInfo
- Publication number
- CN85107284A CN85107284A CN198585107284A CN85107284A CN85107284A CN 85107284 A CN85107284 A CN 85107284A CN 198585107284 A CN198585107284 A CN 198585107284A CN 85107284 A CN85107284 A CN 85107284A CN 85107284 A CN85107284 A CN 85107284A
- Authority
- CN
- China
- Prior art keywords
- formula
- definition
- compound
- pyridine
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 46
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical class SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 67
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- -1 4-chloro-phenyl- Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 241001061127 Thione Species 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 12
- 230000002496 gastric effect Effects 0.000 abstract description 9
- 230000002633 protecting effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 31
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 210000002784 stomach Anatomy 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 8
- 208000025865 Ulcer Diseases 0.000 description 8
- 229960001138 acetylsalicylic acid Drugs 0.000 description 8
- 230000027119 gastric acid secretion Effects 0.000 description 8
- 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 8
- 231100000397 ulcer Toxicity 0.000 description 8
- LVWFHYWRBSIXMC-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-phenylmethanone Chemical compound NCCSC1=NC=CC=C1C(=O)C1=CC=CC=C1 LVWFHYWRBSIXMC-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 230000001120 cytoprotective effect Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 208000007107 Stomach Ulcer Diseases 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 201000005917 gastric ulcer Diseases 0.000 description 4
- 229960000905 indomethacin Drugs 0.000 description 4
- 239000007928 intraperitoneal injection Substances 0.000 description 4
- 229960003151 mercaptamine Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
- HPNCVUBDPCPUDK-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)-6-propylpyridin-4-yl]-phenylmethanone Chemical compound NCCSC1=NC(CCC)=CC(C(=O)C=2C=CC=CC=2)=C1 HPNCVUBDPCPUDK-UHFFFAOYSA-N 0.000 description 3
- KYYDUQIIPZUYPO-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-(2,5-dimethylphenyl)methanone Chemical compound CC1=CC=C(C)C(C(=O)C=2C(=NC=CC=2)SCCN)=C1 KYYDUQIIPZUYPO-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005303 weighing Methods 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
- NUNIXMWDTUKSTG-UHFFFAOYSA-N 2-methoxy-n-methyl-2-pyridin-2-ylethanethioamide Chemical compound CNC(=S)C(OC)C1=CC=CC=N1 NUNIXMWDTUKSTG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 206010022714 Intestinal ulcer Diseases 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 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
- ZBIDSILWMPPVTM-UHFFFAOYSA-N n-acetyl-n-[2-(3-benzoylpyridin-2-yl)sulfanylethyl]acetamide Chemical compound CC(=O)N(C(C)=O)CCSC1=NC=CC=C1C(=O)C1=CC=CC=C1 ZBIDSILWMPPVTM-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000007619 statistical method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- GEWMDEMMESBXBF-UHFFFAOYSA-N (2-chloro-6-propylpyridin-4-yl)-phenylmethanone Chemical compound ClC1=NC(CCC)=CC(C(=O)C=2C=CC=CC=2)=C1 GEWMDEMMESBXBF-UHFFFAOYSA-N 0.000 description 1
- 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
- PYUVIZLPIDWKMW-UHFFFAOYSA-N (4-chlorophenyl)-[2-[2-(dimethylamino)ethylsulfanyl]pyridin-3-yl]methanone Chemical compound CN(C)CCSC1=NC=CC=C1C(=O)C1=CC=C(Cl)C=C1 PYUVIZLPIDWKMW-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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- AEHRGSANGNTNOQ-UHFFFAOYSA-N 2-[2-(2-aminoethylsulfanyl)pyridin-3-yl]-4-chlorobenzaldehyde Chemical compound NCCSC1=NC=CC=C1C1=CC(Cl)=CC=C1C=O AEHRGSANGNTNOQ-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- FNTBXHXRHAFYJT-UHFFFAOYSA-N 2-ethylsulfanylpyridine Chemical class CCSC1=CC=CC=N1 FNTBXHXRHAFYJT-UHFFFAOYSA-N 0.000 description 1
- VKXCZEICJYQFIT-UHFFFAOYSA-N 2-pyridin-2-ylsulfanylethanol Chemical class OCCSC1=CC=CC=N1 VKXCZEICJYQFIT-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 229910014033 C-OH Inorganic materials 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
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 206010017982 Gastrointestinal necrosis Diseases 0.000 description 1
- 206010061459 Gastrointestinal ulcer Diseases 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
- 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 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- IHSWSXHAKQVPGD-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)-1-(1-phenylpropan-2-yl)-2h-pyridin-3-yl]-phenylmethanone Chemical compound C1=CC=C(C(=O)C=2C=CC=CC=2)C(SCCN)N1C(C)CC1=CC=CC=C1 IHSWSXHAKQVPGD-UHFFFAOYSA-N 0.000 description 1
- CVIGZBUHEDENIJ-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-(4-chlorophenyl)methanone Chemical compound NCCSC1=NC=CC=C1C(=O)C1=CC=C(Cl)C=C1 CVIGZBUHEDENIJ-UHFFFAOYSA-N 0.000 description 1
- XQSJHTPXIUFMEN-UHFFFAOYSA-N [2-(2-aminoethylsulfanyl)pyridin-3-yl]-phenylmethanone;hydrochloride Chemical compound Cl.NCCSC1=NC=CC=C1C(=O)C1=CC=CC=C1 XQSJHTPXIUFMEN-UHFFFAOYSA-N 0.000 description 1
- WMRFFFPVTDVNLH-UHFFFAOYSA-N [2-(2-hydroxyethylsulfanyl)pyridin-3-yl]-phenylmethanone Chemical compound OCCSC1=NC=CC=C1C(=O)C1=CC=CC=C1 WMRFFFPVTDVNLH-UHFFFAOYSA-N 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003354 anti-apomorphinic effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004083 gastrointestinal agent Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 208000037907 haemorrhagic injury Diseases 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000017074 necrotic cell death 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
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 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
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- MQDVUDAZJMZQMF-UHFFFAOYSA-N pyridin-2-ylurea Chemical class NC(=O)NC1=CC=CC=N1 MQDVUDAZJMZQMF-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 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
- 150000003335 secondary amines Chemical class 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
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000011272 standard treatment Methods 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
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229950005250 tiquinamide Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU843775A HU192875B (en) | 1984-10-05 | 1984-10-05 | Process for preparing 2-pyridinethiol derivatives |
| HU3775/84 | 1984-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN85107284A true CN85107284A (zh) | 1986-06-10 |
Family
ID=10965437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN198585107284A Pending 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 |
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) | FI853866L (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 |
| US7122542B2 (en) | 2003-07-30 | 2006-10-17 | Rigel Pharmaceuticals, Inc. | Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds |
| 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 PT PT81255A patent/PT81255B/pt unknown
- 1985-10-04 YU YU01583/85A patent/YU158385A/xx unknown
- 1985-10-04 ES ES547604A patent/ES8704460A1/es not_active Expired
- 1985-10-04 ZA ZA857676A patent/ZA857676B/xx unknown
- 1985-10-04 AU AU48328/85A patent/AU579665B2/en not_active Expired - Fee Related
- 1985-10-04 IN IN778/MAS/85A patent/IN162570B/en unknown
- 1985-10-04 AT AT85112599T patent/ATE34739T1/de not_active IP Right Cessation
- 1985-10-04 EP EP85112599A patent/EP0177907B1/de not_active Expired
- 1985-10-04 NO NO853935A patent/NO853935L/no unknown
- 1985-10-04 IL IL76577A patent/IL76577A0/xx unknown
- 1985-10-04 DD DD85281464A patent/DD238384A5/de unknown
- 1985-10-04 CN CN198585107284A patent/CN85107284A/zh active Pending
- 1985-10-04 JP JP60221714A patent/JPS6191172A/ja active Pending
- 1985-10-04 DE DE8585112599T patent/DE3563048D1/de not_active Expired
- 1985-10-04 GR GR852409A patent/GR852409B/el unknown
- 1985-10-04 PL PL1985255643A patent/PL146371B1/pl unknown
- 1985-10-04 SU SU853959903A patent/SU1346042A3/ru active
- 1985-10-04 FI FI853866A patent/FI853866L/fi not_active Application Discontinuation
- 1985-10-04 DK DK455285A patent/DK455285A/da not_active Application Discontinuation
- 1985-10-05 KR KR1019850007352A patent/KR860003212A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IN162570B (enExample) | 1988-06-11 |
| EP0177907B1 (de) | 1988-06-01 |
| HU192875B (en) | 1987-07-28 |
| PT81255B (en) | 1987-03-23 |
| SU1346042A3 (ru) | 1987-10-15 |
| FI853866A7 (fi) | 1986-04-06 |
| NO853935L (no) | 1986-04-07 |
| PL255643A1 (en) | 1987-01-12 |
| HUT38907A (en) | 1986-07-28 |
| DK455285D0 (da) | 1985-10-04 |
| US4713388A (en) | 1987-12-15 |
| DK455285A (da) | 1986-04-06 |
| ATE34739T1 (de) | 1988-06-15 |
| AU579665B2 (en) | 1988-12-01 |
| PT81255A (en) | 1985-11-01 |
| JPS6191172A (ja) | 1986-05-09 |
| DE3563048D1 (en) | 1988-07-07 |
| GR852409B (enExample) | 1986-02-04 |
| DD238384A5 (de) | 1986-08-20 |
| PH21435A (en) | 1987-10-15 |
| ES547604A0 (es) | 1987-04-01 |
| IL76577A0 (en) | 1986-02-28 |
| PL146371B1 (en) | 1989-01-31 |
| ES8704460A1 (es) | 1987-04-01 |
| KR860003212A (ko) | 1986-05-21 |
| ZA857676B (en) | 1986-06-25 |
| EP0177907A1 (de) | 1986-04-16 |
| FI853866A0 (fi) | 1985-10-04 |
| AU4832885A (en) | 1986-04-10 |
| FI853866L (fi) | 1986-04-06 |
| YU158385A (en) | 1988-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1045088C (zh) | 用作pnp抑制剂的嘌呤和鸟嘌呤化合物 | |
| CN1068314C (zh) | 三唑化合物的及其作为多巴胺d3配位体的应用 | |
| CN1198803C (zh) | 具有激活烟碱性乙酰胆碱α4β2受体作用的杂环化合物 | |
| CN88101642A (zh) | 哌嗪基-杂环化合物 | |
| CN1050187A (zh) | 新的喹啉化合物及其制备方法 | |
| CN1161328A (zh) | 氨烷基取代的苯并杂环化合物 | |
| CN1216982A (zh) | 含氮三环化合物和含有该化合物的药物 | |
| CN86102761A (zh) | N-吲哚基乙基-磺酰胺类其制备方法及用途 | |
| CN1051551C (zh) | 新型吡咯并咔唑衍生物 | |
| CN1068566A (zh) | 用作抗缺血剂的2-(4-羟基哌啶子基)-1-烷醇 | |
| CN1067892A (zh) | 新的吡咯并[2，3-b]吡啶衍生物的制备方法 | |
| CN1018644B (zh) | 二唑-烷基-嘌呤衍生物的制备方法 | |
| CN1030753A (zh) | 制备新的取代n-(3-羟基-4-哌啶基)苯甲酰胺的方法 | |
| CN85107284A (zh) | 制备2-吡啶硫醇类衍生物和含有它们的药物配方的方法 | |
| CN1922179A (zh) | 盐酸伐昔洛韦的结晶形式 | |
| CN1097006A (zh) | O-芳基吗啡喃的醚类化合物 | |
| CN1649843A (zh) | 新查耳酮衍生物及其应用 | |
| CN1015457B (zh) | 5-(3-烷基-5-叔丁基-4-羟基苯基)-2-氨基-6h-1，3，4-噻二嗪的制备方法 | |
| CN88101782A (zh) | 抗心律不齐药 | |
| CN1107843A (zh) | 二氢化茚衍生物和其制法及合成该衍生物的中间体 | |
| CN87103528A (zh) | 1，3-二取代的咪唑盐类 | |
| CN1195739C (zh) | 2－氨磺酰苯甲酸衍生物 | |
| CN1051173A (zh) | 新的三唑基酰肼衍生物及其制备方法 | |
| CN85107279A (zh) | 吡啶衍生物的制备方法及其组合物 | |
| CN1430602A (zh) | 芳基－和杂芳基磺酸酯类化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |