JPS6242900B2 - - Google Patents
Info
- Publication number
- JPS6242900B2 JPS6242900B2 JP15899679A JP15899679A JPS6242900B2 JP S6242900 B2 JPS6242900 B2 JP S6242900B2 JP 15899679 A JP15899679 A JP 15899679A JP 15899679 A JP15899679 A JP 15899679A JP S6242900 B2 JPS6242900 B2 JP S6242900B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- mol
- phenyl
- represented
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 11
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000013078 crystal Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- WDTNTQRNRCZODV-UHFFFAOYSA-N 1-cyano-2-methyl-3-[3-(6-oxo-3-phenylpyridazin-1-yl)propyl]guanidine Chemical compound C1=CC(=O)N(CCCN\C(=N/C)NC#N)N=C1C1=CC=CC=C1 WDTNTQRNRCZODV-UHFFFAOYSA-N 0.000 description 1
- WLCLKMPRHUHLMF-UHFFFAOYSA-N 2-(2-aminoethylsulfanylmethyl)-6-phenylpyridazin-3-one Chemical compound C1=CC(=O)N(CSCCN)N=C1C1=CC=CC=C1 WLCLKMPRHUHLMF-UHFFFAOYSA-N 0.000 description 1
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 206010020601 Hyperchlorhydria Diseases 0.000 description 1
- -1 N-cyano-S-methyl-N′-[4-(3- oxo-6-phenyl-2-pyridazinyl) Butyl]isothiourea 2-(4-aminobutyl)-6-phenyl-3 (2H) pyridazinone Chemical compound 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- UHGKYJXJYJWDAM-UHFFFAOYSA-N Propylthiourea Chemical compound CCCNC(N)=S UHGKYJXJYJWDAM-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- PVJKVIFOHYMVQP-UHFFFAOYSA-N methyl n-cyano-n'-[2-[(6-oxo-3-phenylpyridazin-1-yl)methylsulfanyl]ethyl]carbamimidothioate Chemical compound C1=CC(=O)N(CSCCN=C(NC#N)SC)N=C1C1=CC=CC=C1 PVJKVIFOHYMVQP-UHFFFAOYSA-N 0.000 description 1
- PFCBISFUCBFZMU-UHFFFAOYSA-N methyl n-cyano-n'-[3-(6-oxo-3-phenylpyridazin-1-yl)propyl]carbamimidothioate Chemical compound C1=CC(=O)N(CCCN=C(NC#N)SC)N=C1C1=CC=CC=C1 PFCBISFUCBFZMU-UHFFFAOYSA-N 0.000 description 1
- QWSHZFSGAVKJDX-UHFFFAOYSA-N methyl n-cyano-n'-[5-(6-oxo-3-phenylpyridazin-1-yl)pentyl]carbamimidothioate Chemical compound C1=CC(=O)N(CCCCCN=C(NC#N)SC)N=C1C1=CC=CC=C1 QWSHZFSGAVKJDX-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15899679A JPS5681568A (en) | 1979-12-05 | 1979-12-05 | Pyridazinone derivative |
| ZA00807209A ZA807209B (en) | 1979-12-05 | 1980-11-19 | Derivatives of 2-substituted-6-phenyl-3(2h)-pyridazinone |
| AT80304409T ATE3288T1 (de) | 1979-12-05 | 1980-12-05 | 2-substituierte-6-phenyl-3(2h)-pyridazinonderivate, ihre herstellung und sie enthaltende pharmazeutische zusammensetzungen. |
| EP19800304409 EP0030835B1 (en) | 1979-12-05 | 1980-12-05 | Derivatives of 2-substituted-6-phenyl-3(2h)pyridazinone, their production and pharmaceutical compositions containing them |
| ES498263A ES8201553A1 (es) | 1979-12-05 | 1980-12-05 | Procedimiento para la preparacion de derivados de la 6-fenil-3 (2h)-piridacinona 2-substituida |
| DE8080304409T DE3063196D1 (en) | 1979-12-05 | 1980-12-05 | Derivatives of 2-substituted-6-phenyl-3(2h)pyridazinone, their production and pharmaceutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15899679A JPS5681568A (en) | 1979-12-05 | 1979-12-05 | Pyridazinone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5681568A JPS5681568A (en) | 1981-07-03 |
| JPS6242900B2 true JPS6242900B2 (enrdf_load_stackoverflow) | 1987-09-10 |
Family
ID=15683939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15899679A Granted JPS5681568A (en) | 1979-12-05 | 1979-12-05 | Pyridazinone derivative |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5681568A (enrdf_load_stackoverflow) |
| ZA (1) | ZA807209B (enrdf_load_stackoverflow) |
-
1979
- 1979-12-05 JP JP15899679A patent/JPS5681568A/ja active Granted
-
1980
- 1980-11-19 ZA ZA00807209A patent/ZA807209B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5681568A (en) | 1981-07-03 |
| ZA807209B (en) | 1981-11-25 |
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