JPH0143750B2 - - Google Patents
Info
- Publication number
- JPH0143750B2 JPH0143750B2 JP7712481A JP7712481A JPH0143750B2 JP H0143750 B2 JPH0143750 B2 JP H0143750B2 JP 7712481 A JP7712481 A JP 7712481A JP 7712481 A JP7712481 A JP 7712481A JP H0143750 B2 JPH0143750 B2 JP H0143750B2
- Authority
- JP
- Japan
- Prior art keywords
- multiplet
- triplet
- phenyl
- reaction
- doublet
- 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 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 10
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000000862 absorption spectrum Methods 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- -1 3-oxo-6-phenyl-2-pyridazinyl Chemical group 0.000 description 4
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- LKXZODOBTHKFCY-UHFFFAOYSA-N 2-(2-aminoethoxymethyl)-6-phenylpyridazin-3-one Chemical compound C1=CC(=O)N(COCCN)N=C1C1=CC=CC=C1 LKXZODOBTHKFCY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000002541 isothioureas Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- PYFHZGBISZISIP-UHFFFAOYSA-N 1-cyano-2-methyl-3-[2-[(6-oxo-3-phenylpyridazin-1-yl)methoxy]ethyl]guanidine Chemical compound C1=CC(=O)N(COCCN/C(=N/C)NC#N)N=C1C1=CC=CC=C1 PYFHZGBISZISIP-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- BFOMTEBFEFQJHY-UHFFFAOYSA-N 2-phenylpyridazin-3-one Chemical compound O=C1C=CC=NN1C1=CC=CC=C1 BFOMTEBFEFQJHY-UHFFFAOYSA-N 0.000 description 1
- 206010020601 Hyperchlorhydria Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BUFQRIDSXBTSDH-UHFFFAOYSA-N methyl n-cyano-n'-ethylcarbamimidothioate Chemical compound CCN=C(SC)NC#N BUFQRIDSXBTSDH-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000028327 secretion Effects 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7712481A JPS584773A (ja) | 1981-05-20 | 1981-05-20 | ピリダジノン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7712481A JPS584773A (ja) | 1981-05-20 | 1981-05-20 | ピリダジノン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS584773A JPS584773A (ja) | 1983-01-11 |
| JPH0143750B2 true JPH0143750B2 (fi) | 1989-09-22 |
Family
ID=13625040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7712481A Granted JPS584773A (ja) | 1981-05-20 | 1981-05-20 | ピリダジノン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS584773A (fi) |
-
1981
- 1981-05-20 JP JP7712481A patent/JPS584773A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS584773A (ja) | 1983-01-11 |
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