JPS6153350B2 - - Google Patents
Info
- Publication number
- JPS6153350B2 JPS6153350B2 JP8519277A JP8519277A JPS6153350B2 JP S6153350 B2 JPS6153350 B2 JP S6153350B2 JP 8519277 A JP8519277 A JP 8519277A JP 8519277 A JP8519277 A JP 8519277A JP S6153350 B2 JPS6153350 B2 JP S6153350B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- pyridazinone
- compound
- acid
- 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 description 1
- JGSUNMCABQUBOY-UHFFFAOYSA-N 4-oxo-4-(pyridin-3-yl)butanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CN=C1 JGSUNMCABQUBOY-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- -1 alkylpyridyl ketone Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 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
- 230000000936 membranestabilizing effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003443 succinic acid derivatives Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8519277A JPS5419987A (en) | 1977-07-15 | 1977-07-15 | Pyridazinone derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8519277A JPS5419987A (en) | 1977-07-15 | 1977-07-15 | Pyridazinone derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5419987A JPS5419987A (en) | 1979-02-15 |
| JPS6153350B2 true JPS6153350B2 (enrdf_load_stackoverflow) | 1986-11-17 |
Family
ID=13851779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8519277A Granted JPS5419987A (en) | 1977-07-15 | 1977-07-15 | Pyridazinone derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5419987A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4486431A (en) * | 1981-01-14 | 1984-12-04 | Sterling Drug Inc. | Cardiotonic use of 4,5-dihydro-6-(4-pyridinyl)-3(2H)-pyridazinones |
| WO1983000863A1 (en) * | 1981-09-11 | 1983-03-17 | Diamond Shamrock Corp | Antiinflammatory and analgetic 4-pyridylpyridazin(2h)-3-ones |
| US4353905A (en) * | 1981-09-17 | 1982-10-12 | Warner-Lambert Company | Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones |
| US4590194A (en) * | 1981-10-05 | 1986-05-20 | Sterling Drug Inc. | 3-[methyl or dimethyl)amino]-6-(pyridinyl)pyridazines and their cardiotonic use |
-
1977
- 1977-07-15 JP JP8519277A patent/JPS5419987A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5419987A (en) | 1979-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3775422A (en) | Unsymmetrical 1,4-dihydro-4-aryl-nicotinate esters | |
| WO1988002365A1 (en) | Cyclic amine derivatives | |
| US3862161A (en) | 4-pyridyl substituted 1,4-dihydropyridines | |
| US3445473A (en) | 3-anilino-thiophene-4-carboxylic acids,esters,and amides | |
| JP4456765B2 (ja) | ピリダジン−３−オン誘導体及びこれを含有する医薬 | |
| HU193924B (en) | Process for preparing substituted indeno-pyridazines and pharmaceutics comprising the same | |
| NO840329L (no) | Fremgangsmaate for fremstilling av 4-cyanopyridazin-derivater. | |
| CA1248103A (en) | Substituted 5-phenyl-2- (1h)-pyridimidinone compounds | |
| JPS6153350B2 (enrdf_load_stackoverflow) | ||
| JPS6159626B2 (enrdf_load_stackoverflow) | ||
| JPH033669B2 (enrdf_load_stackoverflow) | ||
| JPS61106574A (ja) | オキサ（またはチア）ジアジン誘導体 | |
| JPS6055069B2 (ja) | １−フェニル−シクロペンタンカルボン酸のｎ−ピリジル−アミド、その製造法ならびにそれを有効成分とする消炎および鎮咳剤 | |
| CA1246573A (en) | .alpha.-ARYL-.alpha.-PYRIDYLALKANOIC ACID DERIVATIVES, PROCESS FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME | |
| CA2050875C (en) | 3-(1h-indazol-3-yl)-4-pyridinamines, a process and intermediates for their preparation and their use as medicaments | |
| JPS6245864B2 (enrdf_load_stackoverflow) | ||
| JPS6225661B2 (enrdf_load_stackoverflow) | ||
| JPS6028978A (ja) | １，８−ナフチリジン誘導体 | |
| JPS6317068B2 (enrdf_load_stackoverflow) | ||
| US4377586A (en) | Diuretic 2,6-diaryl-4-pyridine carboxylic acids | |
| JPS626553B2 (enrdf_load_stackoverflow) | ||
| JPS6334874B2 (enrdf_load_stackoverflow) | ||
| US4348395A (en) | 1,4-Dihydropyridazine compounds | |
| WO1983000863A1 (en) | Antiinflammatory and analgetic 4-pyridylpyridazin(2h)-3-ones | |
| JPH0544456B2 (enrdf_load_stackoverflow) |