JPS6257628B2 - - Google Patents
Info
- Publication number
- JPS6257628B2 JPS6257628B2 JP15807978A JP15807978A JPS6257628B2 JP S6257628 B2 JPS6257628 B2 JP S6257628B2 JP 15807978 A JP15807978 A JP 15807978A JP 15807978 A JP15807978 A JP 15807978A JP S6257628 B2 JPS6257628 B2 JP S6257628B2
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- acid
- ethanol
- tetrahydroquinolin
- methyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- -1 methylpiperazinyl Chemical group 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 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 239000002775 capsule Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、一般式
〔式中R1、R2はそれぞれ低級アルキルを示すか、
またはR1とR2とが互いに結合して隣接する窒素
原子とともにピロリジニル、モルホリノまたはＮ
−メチルピペラジニルを形成する。R3、R4はそ
れぞれ水素、低級アルキルを、ｎは２または３の
整数を示す。〕
で表わされるピリダジノン誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula [In the formula, R 1 and R 2 each represent lower alkyl,
or R 1 and R 2 are bonded to each other and together with the adjacent nitrogen atom, pyrrolidinyl, morpholino or N
- forms methylpiperazinyl. R 3 and R 4 each represent hydrogen or lower alkyl, and n represents an integer of 2 or 3. ] This relates to a pyridazinone derivative represented by the following.
一般式（）の化合物は血小板凝集抑制作用、
降圧作用などの薬理作用を有し、抗血栓剤、降圧
剤などの医薬として有用である。 The compound of general formula () has platelet aggregation inhibiting action,
It has pharmacological effects such as antihypertensive action, and is useful as a medicine such as an antithrombotic agent and an antihypertensive agent.
一般式（）の記号の定義をより具体的に説明
すると、低級アルキルとはメチル、エチル、プロ
ピル、イソプロピルなどがあげられる。 To explain the definition of the symbols in the general formula () more specifically, lower alkyl includes methyl, ethyl, propyl, isopropyl, and the like.
一般式（）の化合物は、たとえば以下に示す
方法により製造することができる。 The compound of general formula () can be produced, for example, by the method shown below.
一般式
（式中、各記号は前記と同義である。）
で表わされる化合物またはその反応性誘導体（エ
ステル、酸無水物など）とヒドラジンまたはその
水和物と反応させる方法。 general formula (In the formula, each symbol has the same meaning as above.) A method of reacting a compound represented by the following or a reactive derivative thereof (ester, acid anhydride, etc.) with hydrazine or a hydrate thereof.
この反応は、無溶媒または適当な溶媒中、室温
ないし加熱下に行われる。溶媒としては本発明の
反応を妨げないものであればどのようなものでも
よく、たとえば水、メタノール、エタノール、プ
ロパノール、イソプロパノール、テトラヒドロフ
ラン、ジオキサン、ベンゼン、トルエン、ジメチ
ルホルムアミドなど、またはこれらの混合溶媒が
あげられる。 This reaction is carried out without a solvent or in a suitable solvent at room temperature or under heating. Any solvent may be used as long as it does not interfere with the reaction of the present invention, such as water, methanol, ethanol, propanol, isopropanol, tetrahydrofuran, dioxane, benzene, toluene, dimethylformamide, or a mixed solvent thereof. can give.
このようにして製造された本発明の化合物
（）は常法により無機酸（塩酸、臭化水素酸、
硫酸など）または有機酸（シユウ酸、マレイン
酸、コハク酸、フマール酸、メタンスルホン酸な
ど）と処理することにより、対応の酸付加塩とす
ることができる。 The compound () of the present invention thus produced can be prepared using an inorganic acid (hydrochloric acid, hydrobromic acid,
The corresponding acid addition salts can be obtained by treatment with sulfuric acid, etc.) or organic acids (oxalic acid, maleic acid, succinic acid, fumaric acid, methanesulfonic acid, etc.).
一般式（）の化合物は新規化合物であり、た
とえば以下に示すように、それ自体は公知の方法
で製造することができる。 The compound of general formula () is a new compound, and can be produced by a method known per se, for example, as shown below.
（式中、Ｘは塩素、臭素などのハロゲンを示し、
他の記号は前記と同義である。）
本発明の化合物（）を前述の医薬として用い
る場合、それ自体あるいは適宜の薬理的に許容さ
れる担体、賦形剤、希釈剤などと混合し、散剤、
顆粒剤、錠剤、カプセル剤、注射剤などの形態で
経口的または非経口的に投与できる。投与量は対
象疾患、症状、用いる化合物によつても異なる
が、経口投与の場合、通常成人１日あたり１〜
1000mg程度である。 (In the formula, X represents a halogen such as chlorine or bromine,
Other symbols have the same meanings as above. ) When the compound () of the present invention is used as the above-mentioned medicine, it can be used as such or mixed with an appropriate pharmacologically acceptable carrier, excipient, diluent, etc., and can be prepared as a powder,
It can be administered orally or parenterally in the form of granules, tablets, capsules, injections, etc. The dosage varies depending on the target disease, symptoms, and compound used, but in the case of oral administration, it is usually 1 to 1 per day for adults.
It is about 1000mg.
次に、本発明を実施例をあげて具体的に説明す
る。 Next, the present invention will be specifically explained with reference to Examples.
実施例 １
４−オキソ−４−〔１−（２−ジエチルアミノエ
チル）−２−オキソ−４・４−ジメチル−１・
２・３・４−テトラヒドロキノリン−６−イル〕
−３−メチルブタン酸５ｇ、85％ヒドラジン・水
和物３ｇおよびエタノール100mlの混合物を30分
間加熱還流する。溶媒を減圧留去し、残査をクロ
ロホルムに溶かし、水洗後、炭酸カリウムにて脱
水し、さらに溶媒を減圧留去する。残査をエタノ
ールに溶かし、エタノール−塩酸を加え、析出す
る結晶を取し、エタノールから再結晶すると、
融点240〜245℃（分解）の１−（２−ジエチルア
ミノエチル）−４・４−ジメチル−６−（５−メチ
ル−３−オキソ−２・３・４・５−テトラヒドロ
ピリダジン−６−イル）−１・２・３・４−テト
ラヒドロキノリン−２−オン・塩酸塩・1/2水和
物３ｇが得られる。Example 1 4-oxo-4-[1-(2-diethylaminoethyl)-2-oxo-4.4-dimethyl-1.
2,3,4-tetrahydroquinolin-6-yl]
A mixture of 5 g of -3-methylbutanoic acid, 3 g of 85% hydrazine hydrate and 100 ml of ethanol is heated under reflux for 30 minutes. The solvent was distilled off under reduced pressure, the residue was dissolved in chloroform, washed with water, dried over potassium carbonate, and the solvent was further distilled off under reduced pressure. Dissolve the residue in ethanol, add ethanol-hydrochloric acid, collect the precipitated crystals, and recrystallize from ethanol.
1-(2-diethylaminoethyl)-4,4-dimethyl-6-(5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl), melting point 240-245°C (decomposition) 3 g of -1,2,3,4-tetrahydroquinolin-2-one hydrochloride 1/2 hydrate is obtained.
実施例 ２
４−オキソ−４−〔１−（３−モルホリノプロピ
ル）−２−オキソ−１・２・３・４−テトラヒド
ロキノリン−６−イル〕−３−メチルブタン酸５
ｇ、85％ヒドラジン・水和物３ｇおよびエタノー
ル100mlの混合物を３時間加熱還流する。溶媒を
減圧留去し、残査を酢酸エチルに溶かし、水洗
後、炭酸カリウムにて脱水し、さらに溶媒を減圧
留去する。残査をエタノールに溶かし、エタノー
ル−塩酸を加え、析出する結晶を取し、エタノ
ールから再結晶すると、融点253〜255℃の１−
（３−モルホリノプロピル）−６−（５−メチル−
３−オキソ−２・３・４・５−テトラヒドロピリ
ダジン−６−イル）−１・２・３・４−テトラヒ
ドロキノリン−２−オン・塩酸塩・1/2水和物2.9
ｇが得られる。Example 2 4-oxo-4-[1-(3-morpholinopropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl]-3-methylbutanoic acid 5
A mixture of 3 g of 85% hydrazine hydrate and 100 ml of ethanol is heated under reflux for 3 hours. The solvent was distilled off under reduced pressure, the residue was dissolved in ethyl acetate, washed with water, dried over potassium carbonate, and the solvent was further distilled off under reduced pressure. Dissolve the residue in ethanol, add ethanol-hydrochloric acid, collect the precipitated crystals, and recrystallize from ethanol.
(3-morpholinopropyl)-6-(5-methyl-
3-Oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1,2,3,4-tetrahydroquinolin-2-one hydrochloride 1/2 hydrate 2.9
g is obtained.
上記実施例と同様にして、さらに、たとえば次
の化合物が製造される。 In the same manner as in the above examples, the following compounds are further produced, for example.
◎１−（２−ジメチルアミノエチル）−６−（５−
メチル−３−オキソ−２・３・４・５−テトラ
ヒドロピリダジン−６−イル）−１・２・３・
４−テトラヒドロキノリン−２−オン・塩酸
塩・1/2水和物、融点155〜157℃
◎１−〔３−（４−メチルピペラジン−１−イル）
プロピル〕−６−（５−メチル−３−オキソ−
２・３・４・５−テトラヒドロピリダジン−６
−イル）−１・２・３・４−テトラヒドロキノ
リン−２−オン・２塩酸塩・1/2水和物、融点
266〜267℃
◎１−〔３−（１−ピロリジニル）プロピル〕−６
−（５−メチル−３−オキソ−２・３・４・５
−テトラヒドロピリダジン−６−イル）−１・
２・３・４−テトラヒドロキノリン−２−オ
ン・塩酸塩・1/2水和物、融点249〜251℃
◎１−（２−モルホリノエチル）−４・４−ジメチ
ル−６−（５−メチル−３−オキソ−２・３・
４・５−テトラヒドロピリダジン−６−イル）
−１・２・３・４−テトラヒドロキノリン−２
−オン・塩酸塩、融点270〜273℃（分解）
◎１−（３−ジメチルアミノプロピル）−４・４−
ジメチル−６−（５−メチル−３−オキソ−
２・３・４・５−テトラヒドロピリダジン−６
−イル）−１・２・３・４−テトラヒドロキノ
リン−２−オン・塩酸塩、融点269〜271℃◎1-(2-dimethylaminoethyl)-6-(5-
Methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1,2,3.
4-tetrahydroquinolin-2-one hydrochloride 1/2 hydrate, melting point 155-157℃ ◎1-[3-(4-methylpiperazin-1-yl)
propyl]-6-(5-methyl-3-oxo-
2,3,4,5-tetrahydropyridazine-6
-yl)-1,2,3,4-tetrahydroquinolin-2-one dihydrochloride 1/2 hydrate, melting point
266-267℃ ◎1-[3-(1-pyrrolidinyl)propyl]-6
-(5-methyl-3-oxo-2,3,4,5
-tetrahydropyridazin-6-yl)-1.
2,3,4-tetrahydroquinolin-2-one hydrochloride, 1/2 hydrate, melting point 249-251℃ ◎1-(2-morpholinoethyl)-4,4-dimethyl-6-(5-methyl -3-oxo-2.3.
4,5-tetrahydropyridazin-6-yl)
-1,2,3,4-tetrahydroquinoline-2
-one hydrochloride, melting point 270-273℃ (decomposition) ◎1-(3-dimethylaminopropyl)-4・4-
Dimethyl-6-(5-methyl-3-oxo-
2,3,4,5-tetrahydropyridazine-6
-yl)-1,2,3,4-tetrahydroquinolin-2-one hydrochloride, melting point 269-271℃
Claims (1)
またはR1とR2とが互いに結合して隣接する窒素
原子とともにピロリジニル、モルホリノまたはＮ
−メチルピペラジニルを形成する。R3、R4はそ
れぞれ水素、低級アルキルを、ｎは２または３の
整数を示す。〕 で表わされるピリダジノン誘導体。[Claims] 1 [In the formula, R 1 and R 2 each represent lower alkyl,
or R 1 and R 2 are bonded to each other and together with the adjacent nitrogen atom, pyrrolidinyl, morpholino or N
- forms methylpiperazinyl. R 3 and R 4 each represent hydrogen or lower alkyl, and n represents an integer of 2 or 3. ] A pyridazinone derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15807978A JPS5583781A (en) | 1978-12-19 | 1978-12-19 | Pyridazinone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15807978A JPS5583781A (en) | 1978-12-19 | 1978-12-19 | Pyridazinone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5583781A JPS5583781A (en) | 1980-06-24 |
| JPS6257628B2 true JPS6257628B2 (en) | 1987-12-02 |
Family
ID=15663828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15807978A Granted JPS5583781A (en) | 1978-12-19 | 1978-12-19 | Pyridazinone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5583781A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5777676A (en) * | 1980-10-31 | 1982-05-15 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| CA2067475C (en) * | 1991-05-08 | 2000-10-10 | Yasuo Oshiro | Carbostyril derivatives and their use |
-
1978
- 1978-12-19 JP JP15807978A patent/JPS5583781A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5583781A (en) | 1980-06-24 |
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