NL8004630A - 1,2,4-triazool-3-thiolen. - Google Patents
1,2,4-triazool-3-thiolen. Download PDFInfo
- Publication number
- NL8004630A NL8004630A NL8004630A NL8004630A NL8004630A NL 8004630 A NL8004630 A NL 8004630A NL 8004630 A NL8004630 A NL 8004630A NL 8004630 A NL8004630 A NL 8004630A NL 8004630 A NL8004630 A NL 8004630A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- amino
- triazole
- compound
- thiol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 20
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- NHJQUZUFQOQBNE-UHFFFAOYSA-N 4-amino-3-ethyl-1h-1,2,4-triazole-5-thione Chemical compound CCC1=NNC(=S)N1N NHJQUZUFQOQBNE-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical class SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000005544 phthalimido group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- DNXIQMQGKSQHPC-UHFFFAOYSA-N 7-methoxy-3,4,5,6-tetrahydro-2h-azepine Chemical compound COC1=NCCCCC1 DNXIQMQGKSQHPC-UHFFFAOYSA-N 0.000 claims description 3
- 230000001262 anti-secretory effect Effects 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 230000028327 secretion Effects 0.000 claims description 2
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- -1 4-amino-5-propyl-4H-1,4,4-triazole-3-thiol Chemical compound 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229940100445 wheat starch Drugs 0.000 description 3
- GGUGNJFKCKKFHF-UHFFFAOYSA-N 4-amino-3-(2-aminoethyl)-1h-1,2,4-triazole-5-thione;hydrochloride Chemical compound Cl.NCCC1=NN=C(S)N1N GGUGNJFKCKKFHF-UHFFFAOYSA-N 0.000 description 2
- KBXICHKCUANJOH-UHFFFAOYSA-N 4-amino-3-(2-ethoxyethyl)-1h-1,2,4-triazole-5-thione Chemical compound CCOCCC1=NN=C(S)N1N KBXICHKCUANJOH-UHFFFAOYSA-N 0.000 description 2
- DSYVZXYIXGRKQV-UHFFFAOYSA-N 4-amino-3-(ethoxymethyl)-1h-1,2,4-triazole-5-thione Chemical compound CCOCC1=NN=C(S)N1N DSYVZXYIXGRKQV-UHFFFAOYSA-N 0.000 description 2
- MSDOJJSTMSPMNO-UHFFFAOYSA-N 4-amino-3-(hydroxymethyl)-1h-1,2,4-triazole-5-thione Chemical compound NN1C(CO)=NNC1=S MSDOJJSTMSPMNO-UHFFFAOYSA-N 0.000 description 2
- SEAKEZRPLBHURI-UHFFFAOYSA-N 4-amino-3-(methoxymethyl)-1h-1,2,4-triazole-5-thione Chemical compound COCC1=NNC(=S)N1N SEAKEZRPLBHURI-UHFFFAOYSA-N 0.000 description 2
- TVBCCWGVCZSXFD-UHFFFAOYSA-N 4-amino-3-butyl-1h-1,2,4-triazole-5-thione Chemical compound CCCCC1=NNC(=S)N1N TVBCCWGVCZSXFD-UHFFFAOYSA-N 0.000 description 2
- OKNHZPGPLNUEPC-UHFFFAOYSA-N 4-amino-3-phenyl-1h-1,2,4-triazole-5-thione Chemical compound NN1C(S)=NN=C1C1=CC=CC=C1 OKNHZPGPLNUEPC-UHFFFAOYSA-N 0.000 description 2
- QKCNMYZGZIKYHA-UHFFFAOYSA-N 5-ethyl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound CCC1=NC(=S)NN1 QKCNMYZGZIKYHA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229960004275 glycolic acid Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- MACMNSLOLFMQKL-UHFFFAOYSA-N 1-sulfanyltriazole Chemical compound SN1C=CN=N1 MACMNSLOLFMQKL-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
- MLRAJZNPKPVUDQ-UHFFFAOYSA-N 3-sulfanyl-1,2-dihydrotriazole Chemical compound SN1NNC=C1 MLRAJZNPKPVUDQ-UHFFFAOYSA-N 0.000 description 1
- MGXFOJVHRYIZTK-UHFFFAOYSA-N 4-amino-3-(5-aminopentyl)-1h-1,2,4-triazole-5-thione;hydrochloride Chemical compound Cl.NCCCCCC1=NN=C(S)N1N MGXFOJVHRYIZTK-UHFFFAOYSA-N 0.000 description 1
- KBKNKJFPVHUXCW-UHFFFAOYSA-N 4-amino-3-methyl-1h-1,2,4-triazole-5-thione Chemical compound CC1=NNC(=S)N1N KBKNKJFPVHUXCW-UHFFFAOYSA-N 0.000 description 1
- ROAXVRKEIASZAE-UHFFFAOYSA-N 4-amino-3-propyl-1h-1,2,4-triazole-5-thione Chemical compound CCCC1=NNC(=S)N1N ROAXVRKEIASZAE-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000001929 anti-hepatotoxic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000000273 goitrogenic effect Effects 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 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
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/071,814 US4230715A (en) | 1979-09-04 | 1979-09-04 | 1,2,4-Triazole-3-thiols as antisecretory agents |
| US7181479 | 1979-09-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8004630A true NL8004630A (nl) | 1981-03-06 |
Family
ID=22103760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8004630A NL8004630A (nl) | 1979-09-04 | 1980-08-15 | 1,2,4-triazool-3-thiolen. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4230715A (fr) |
| JP (1) | JPS5640672A (fr) |
| AU (1) | AU6108980A (fr) |
| BE (1) | BE885015A (fr) |
| DE (1) | DE3031320A1 (fr) |
| DK (1) | DK375480A (fr) |
| ES (1) | ES494226A0 (fr) |
| FR (1) | FR2464257A1 (fr) |
| GB (1) | GB2057446A (fr) |
| IL (1) | IL60763A0 (fr) |
| IT (1) | IT1145443B (fr) |
| NL (1) | NL8004630A (fr) |
| NO (1) | NO802592L (fr) |
| SE (1) | SE8006142L (fr) |
| ZA (1) | ZA804668B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0232382U (fr) * | 1988-08-22 | 1990-02-28 | ||
| US5489598A (en) * | 1994-06-08 | 1996-02-06 | Warner-Lambert Company | Cytoprotection utilizing aryltriazol-3-thiones |
| AU704798B2 (en) * | 1995-04-20 | 1999-05-06 | Hoechst Marion Roussel, Inc. | 3-phenyl-1,4-dialkyl-1,2,4-triazolium salts and their use as antidepressants |
| US20030125562A1 (en) * | 1999-08-21 | 2003-07-03 | Heindel Ned H. | Methods of producing 4-amino-3-mercapto-triazoles |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB928919A (en) * | 1960-08-16 | 1963-06-19 | Bellon Labor Sa Roger | Triazole derivatives and a process for their preparation |
| DE1620506A1 (de) * | 1965-07-07 | 1970-01-02 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen 1,2,4-Triazolin-Thionen-(5) |
| US3701784A (en) * | 1968-09-04 | 1972-10-31 | Rohm & Haas | 1,2,4-4h-triazole derivatives |
| US3818097A (en) * | 1969-10-29 | 1974-06-18 | Smith Kline French Lab | Method of inhibiting histamine activity with isothioureas |
| IL49200A0 (en) * | 1975-03-27 | 1976-05-31 | Pfizer | Novel heterocyclic thiols and their preparation |
-
1979
- 1979-09-04 US US06/071,814 patent/US4230715A/en not_active Expired - Lifetime
-
1980
- 1980-07-31 ZA ZA00804668A patent/ZA804668B/xx unknown
- 1980-08-05 IL IL60763A patent/IL60763A0/xx unknown
- 1980-08-05 AU AU61089/80A patent/AU6108980A/en not_active Abandoned
- 1980-08-13 ES ES494226A patent/ES494226A0/es active Granted
- 1980-08-15 NL NL8004630A patent/NL8004630A/nl not_active Application Discontinuation
- 1980-08-20 DE DE19803031320 patent/DE3031320A1/de not_active Withdrawn
- 1980-08-21 JP JP11411880A patent/JPS5640672A/ja active Pending
- 1980-08-22 IT IT49543/80A patent/IT1145443B/it active
- 1980-09-01 BE BE0/201936A patent/BE885015A/fr unknown
- 1980-09-02 GB GB8028289A patent/GB2057446A/en not_active Withdrawn
- 1980-09-03 DK DK375480A patent/DK375480A/da unknown
- 1980-09-03 NO NO802592A patent/NO802592L/no unknown
- 1980-09-03 SE SE8006142A patent/SE8006142L/xx not_active Application Discontinuation
- 1980-09-04 FR FR8019132A patent/FR2464257A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IL60763A0 (en) | 1980-10-26 |
| FR2464257A1 (fr) | 1981-03-06 |
| US4230715A (en) | 1980-10-28 |
| ES8106147A1 (es) | 1981-08-01 |
| ES494226A0 (es) | 1981-08-01 |
| NO802592L (no) | 1981-03-05 |
| GB2057446A (en) | 1981-04-01 |
| ZA804668B (en) | 1981-07-29 |
| IT8049543A0 (it) | 1980-08-22 |
| DE3031320A1 (de) | 1981-03-26 |
| JPS5640672A (en) | 1981-04-16 |
| SE8006142L (sv) | 1981-03-05 |
| DK375480A (da) | 1981-03-05 |
| IT1145443B (it) | 1986-11-05 |
| AU6108980A (en) | 1981-03-12 |
| BE885015A (fr) | 1980-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3541042B2 (ja) | 置換３，５―ジフェニル―１，２，４―トリアゾールおよび製薬的金属キレート化剤としてのその使用 | |
| SU1373318A3 (ru) | Способ получени производных пирролидинона или их кислотно-аддитивных солей | |
| HU224212B1 (hu) | 5-[4-[2-(N-metil-N-(2-piridil)amino)etoxi]benzil]tiazolidin-2,4-dion-maleát és ezt tartalmazó gyógyszerkészítmények | |
| US3910942A (en) | Anthelmintic (isothiocyanophenyl) oxadiazoles | |
| US3639477A (en) | Novel propoxyguanidine compounds and means of producing the same | |
| JPS5830314B2 (ja) | グアニジン化合物の製法 | |
| JPS6131099B2 (fr) | ||
| JPS5989671A (ja) | ２，５−ピペラジンジオン誘導体 | |
| EP0070084A2 (fr) | Dérivés d'imidazoline | |
| RU2039051C1 (ru) | Производные триазолилгидразида и их фармацевтически пригодные соли | |
| JPH01151517A (ja) | 抗けいれん薬、筋弛緩薬および抗不安薬としての３−アミノ−５−メチル−１ｈ−ピラゾール−４−カルボン酸類およびそれらのエステル | |
| JPS6155915B2 (fr) | ||
| JPS5839148B2 (ja) | Ｎ−置換２−ピロリジノンおよび同製造法 | |
| US4230715A (en) | 1,2,4-Triazole-3-thiols as antisecretory agents | |
| CS200543B2 (en) | Method of producing novel derivatives of pyrido-2,3-b-1,5-benzothiazepine | |
| US3953461A (en) | Amino derivatives of thiazolo[5,4-b]pyridine-6-carboxylic acids and esters | |
| US4411905A (en) | Antisecretory 1,2,4-triazole-3-thiols | |
| US3699116A (en) | 2,2'-azines of 2,4-thiazolidinediones | |
| US3499084A (en) | Substituted oxazolines,useful as pharmaceuticals | |
| SE444316B (sv) | 3,5-disubstituerade 1h-1,2,4-triazoler till anvendning som antifertilitetsmedel | |
| HU176328B (en) | Process for preparing isothiocarbamide derivatives | |
| HU197843B (en) | Process for producing pharmaceutical compositions comprising 2-alkoxy-n-(1-azabicyclo/2.2.2/oct-3-yl)-benzamide-n-oxide derivatives | |
| US3755306A (en) | 3-arylsulfony l-1,2,4-oxadiazoles | |
| US3720668A (en) | Nitrofuryl-oxadiazole amides | |
| SE447249B (sv) | Bensamidinderivat jemte terapeutisk komposition innefattande derivatet |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |