JPS631304B2 - - Google Patents
Info
- Publication number
- JPS631304B2 JPS631304B2 JP53140801A JP14080178A JPS631304B2 JP S631304 B2 JPS631304 B2 JP S631304B2 JP 53140801 A JP53140801 A JP 53140801A JP 14080178 A JP14080178 A JP 14080178A JP S631304 B2 JPS631304 B2 JP S631304B2
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- melting point
- lower alkyl
- tetrahydroquinolin
- formula
- 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 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000007660 quinolones Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000008018 melting Effects 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- GVCMFAGYMNVFSA-UHFFFAOYSA-N 1,4,4-trimethyl-3h-quinolin-2-one Chemical compound C1=CC=C2N(C)C(=O)CC(C)(C)C2=C1 GVCMFAGYMNVFSA-UHFFFAOYSA-N 0.000 description 1
- CLRISZVRNLFZQT-UHFFFAOYSA-N 1,4,4-trimethyl-6-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)-3h-quinolin-2-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(N(C)C(=O)CC2(C)C)C2=C1 CLRISZVRNLFZQT-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- JFRLBDSCLAVUJC-UHFFFAOYSA-N 3-methyl-4-oxo-4-(1,4,4-trimethyl-2-oxo-3h-quinolin-6-yl)butanoic acid Chemical compound CN1C(=O)CC(C)(C)C2=CC(C(=O)C(CC(O)=O)C)=CC=C21 JFRLBDSCLAVUJC-UHFFFAOYSA-N 0.000 description 1
- HMOBRUPKXAKFHS-UHFFFAOYSA-N 4,4-dimethyl-1,3-dihydroquinolin-2-one Chemical compound C1=CC=C2C(C)(C)CC(=O)NC2=C1 HMOBRUPKXAKFHS-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003146 anticoagulant 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
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008187 granular material Substances 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
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 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
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
本発明は、一般式
〔式中、Ｒは水素、低級アルキルを示す。R1は
水素を示すか、またはR2とともに単結合を形成
する。R2、R3はそれぞれ水素、低級アルキルを
示す。ただし、R1、R2、R3はもとに水素ではな
い。R4は低級アルキル、−CH2CH2COOH、
The present invention is based on the general formula [In the formula, R represents hydrogen or lower alkyl. R 1 represents hydrogen or forms a single bond with R 2 . R 2 and R 3 represent hydrogen and lower alkyl, respectively. However, R 1 , R 2 , and R 3 are not originally hydrogen. R 4 is lower alkyl, −CH 2 CH 2 COOH,
【式】（R5は低級アルキルを示
す。）を示す。〕
で表わされるキノロン誘導体に関する。
一般式（）の化合物は、抗炎症作用、血小板
凝集抑制作用などの薬理作用を有し、抗炎症剤、
抗血栓剤などの医薬として有用であるとともに、
たとえば、強い血小板凝集抑制作用を持つ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・４・４
−トリメチル−１・２・３・４−テトラヒドロキ
ノリン−２−オン、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）−４−メチル−１・２・３・４−テト
ラヒドロキノリン−２−オンなどの合成中間体と
しても有用である。
一般式（）の各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、ブチル、イソブチルなど
を示す。
一般式（）の化合物は、たとえば、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と、一般式
（R6CO）nＸ （）
（式中、R6はメチル、エチル、プロピル、イソ
プロピル、ブチル、イソブチルなどの直鎖状また
は分枝状のアルキルを、Ｘはハロゲンまたは酸素
を示す。ｍは、Ｘがハロゲンのとき、１を、Ｘが
酸素のとき、２を示す。）
で表わされる化合物、または一般式
（式中、Ａは前記と同義である。）
で表わされる化合物とを、無溶媒中または溶媒中
で、触媒の存在下に０℃から還流下に反応させる
ことにより製造することができる。溶媒としては
反応を妨げない限りいかなるものでもよく、たと
えばメチレンクロライド、エチレンクロライド、
クロロホルム、四塩化炭酸、ニトロベンゼン、二
硫化炭素などがあげられる。触媒としては、塩化
アルミニウム、塩化亜鉛、塩化第二鉄、四塩化
錫、三フツ化ホウ素などのルイス酸があげられ
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。
次に本発明を実施例をあげて、具体的に説明す
る。
実施例 １
４・４−ジメチル−１・２・３・４−テトラヒ
ドロキノリン−２−オン70ｇ、プロピオニルクロ
ライド55.5ｇおよびエチレンクロライド400mlの
混合物に塩化アルミニウム177ｇを20℃以下にて
加える。この混合物を50〜60℃に３時間加熱撹拌
し、冷後、氷水に注ぎ、クロロホルムにて抽出す
る。有機層を水洗し、硫酸マグネシウムにて乾燥
後、溶媒を減圧留去する。残渣にイソプロピルエ
ーテルを入れ、析出する結晶を取し、イソプロ
ピルエーテルから再結晶すると、融点154〜158℃
の４・４−ジメチル−６−プロピオニル−１・
２・３・４−テトラヒドロキノリン−２−オン69
ｇが得られる。
実施例 ２
１・４・４−トリメチル−１・２・３・４−テ
トラヒドロキノリン−２−オン23.5ｇ、無水コハ
ク酸13ｇおよびエチレンクロライド150mlの混合
物に無水塩化アルミニウム50ｇを20℃以下にて加
える。この混合物を65〜75℃に７時間加熱撹拌
し、冷後、氷水に注ぐ。クロロホルムにて抽出
し、水洗する。この有機層を10％水酸化ナトリウ
ム水溶液にて抽出し、塩酸で酸性にすると、結晶
が析出する。結晶を取し、メタノールから再結
晶すると、融点194〜197℃の４−オキソ−４−
（１・４・４−トリメチル−２−オキソ−１・
２・３・４−テトラヒドロキノリン−６−イル）
ブタン酸16.3ｇが得られる。
上記実施例と同様にして、さらに次の化合物が
製造される。
◎１・４・４−トリメチル−６−プロピオニル−
１・２・３・４−テトラヒドロキノリン−２−
オン、融点94〜97℃
◎１・４−ジメチル−６−プロピオニル−１・
２・３・４−テトラヒドロキノリン−２−オ
ン、融点103〜106℃
◎４−メチル−６−プロピオニル−１・２・３・
４−テトラヒドロキノリン−２−オン、融点
154〜155℃
◎６−アセチル−１・４−ジメチル−１・２−ジ
ヒドロキノリン−２−オン、融点154〜155℃
◎１・４−ジメチル−６−プロピオニル−１・２
−ジヒドロキノリン−２−オン、融点173〜174
℃
◎４−メチル−６−プロピオニル−１・２−ジヒ
ドロキノリン−２−オン、融点215〜218℃
◎４−オキソ−４−（１・４−ジメチル−２−オ
キソ−１・２・３・４−テトラヒドロキノリン
−６−イル）ブタン酸、融点170〜172℃
◎４−オキソ−４−（４−メチル−２−オキソ−
１・２・３・４−テトラヒドロキノリン−６−
イル）ブタン酸、融点206〜209℃
◎４−オキソ−４−（１・４−ジメチル−２−オ
キソ−１・２−ジヒドロキノリン−６−イル）
ブタン酸、融点240〜243℃（分解）
◎４−オキソ−４−（１・４・４−トリメチル−
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、融
点133〜135℃
◎４−オキソ−４−（４−メチル−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、融点172〜174℃[Formula] (R 5 represents lower alkyl) is shown. ] Regarding the quinolone derivative represented by. The compound of general formula () has pharmacological actions such as anti-inflammatory action and platelet aggregation inhibiting action, and is an anti-inflammatory agent.
It is useful as a medicine such as an antithrombotic agent, and
For example, 6-
(5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1,4,4
-Trimethyl-1,2,3,4-tetrahydroquinolin-2-one, 6-(5-methyl-3-oxo-2,3,4,5-tetrahydropyridazine-
It is also useful as a synthetic intermediate such as 6-yl)-4-methyl-1,2,3,4-tetrahydroquinolin-2-one. To explain the definition of each symbol in the general formula () more specifically, lower alkyl refers to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and the like. A compound of the general formula () is, for example, a compound of the general formula (In the formula, each symbol has the same meaning as above.) Compounds represented by the general formula (R 6 CO ) n a straight-chain or branched alkyl, X represents halogen or oxygen; m represents 1 when X is halogen; and 2 when X represents oxygen.) or a compound represented by formula (In the formula, A has the same meaning as above.) It can be produced by reacting the compound represented by the following in the absence of a solvent or in a solvent under reflux from 0° C. in the presence of a catalyst. Any solvent may be used as long as it does not interfere with the reaction, such as methylene chloride, ethylene chloride,
Examples include chloroform, carbon dioxide tetrachloride, nitrobenzene, and carbon disulfide. Examples of the catalyst include Lewis acids such as aluminum chloride, zinc chloride, ferric chloride, tin tetrachloride, and boron trifluoride. When the compound of the present invention is used as the above-mentioned medicine, it may be used by itself or mixed with appropriate pharmacologically acceptable carriers, excipients, diluents, etc., to form powders, granules, tablets, capsules, injections, etc. It can be administered orally or parenterally. The dosage varies depending on the target disease, symptoms, and compound used, but in the case of oral administration, it is usually about 1 to 1000 mg per day for adults. Next, the present invention will be specifically explained with reference to Examples. Example 1 177 g of aluminum chloride is added to a mixture of 70 g of 4,4-dimethyl-1,2,3,4-tetrahydroquinolin-2-one, 55.5 g of propionyl chloride and 400 ml of ethylene chloride at a temperature below 20°C. This mixture is heated and stirred at 50-60°C for 3 hours, cooled, poured into ice water, and extracted with chloroform. The organic layer was washed with water, dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. Add isopropyl ether to the residue, collect the precipitated crystals, and recrystallize from isopropyl ether to obtain a melting point of 154-158℃.
4,4-dimethyl-6-propionyl-1.
2,3,4-tetrahydroquinolin-2-one 69
g is obtained. Example 2 50 g of anhydrous aluminum chloride is added to a mixture of 23.5 g of 1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-2-one, 13 g of succinic anhydride, and 150 ml of ethylene chloride at a temperature below 20°C. . The mixture is heated and stirred at 65-75°C for 7 hours, cooled, and then poured into ice water. Extract with chloroform and wash with water. This organic layer is extracted with a 10% aqueous sodium hydroxide solution and acidified with hydrochloric acid to precipitate crystals. When the crystals are collected and recrystallized from methanol, 4-oxo-4- with a melting point of 194-197℃ is obtained.
(1,4,4-trimethyl-2-oxo-1.
2,3,4-tetrahydroquinolin-6-yl)
16.3 g of butanoic acid are obtained. The following compounds are further produced in the same manner as in the above examples. ◎1,4,4-trimethyl-6-propionyl-
1,2,3,4-tetrahydroquinoline-2-
Melting point: 94-97℃ ◎1,4-dimethyl-6-propionyl-1.
2,3,4-tetrahydroquinolin-2-one, melting point 103-106℃ ◎4-Methyl-6-propionyl-1,2,3.
4-tetrahydroquinolin-2-one, melting point
154-155℃ ◎6-acetyl-1,4-dimethyl-1,2-dihydroquinolin-2-one, melting point 154-155℃ ◎1,4-dimethyl-6-propionyl-1,2
-dihydroquinolin-2-one, melting point 173-174
℃ ◎4-Methyl-6-propionyl-1,2-dihydroquinolin-2-one, melting point 215-218℃ ◎4-oxo-4-(1,4-dimethyl-2-oxo-1,2,3, 4-Tetrahydroquinolin-6-yl)butanoic acid, melting point 170-172℃ ◎4-oxo-4-(4-methyl-2-oxo-
1,2,3,4-tetrahydroquinoline-6-
yl)butanoic acid, melting point 206-209℃ ◎4-oxo-4-(1,4-dimethyl-2-oxo-1,2-dihydroquinolin-6-yl)
Butanoic acid, melting point 240-243℃ (decomposed) ◎4-oxo-4-(1,4,4-trimethyl-
2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-3-methylbutanoic acid, melting point 133-135℃ ◎4-oxo-4-(4-methyl-2-oxo-
1,2,3,4-tetrahydroquinoline-6-
yl)-3-methylbutanoic acid, melting point 172-174℃
Claims (1)
水素を示すか、またはR2とともに単結合を形成
する。R2、R3はそれぞれ水素、低級アルキルを
示す。ただし、R1、R2、R3はともに水素ではな
い。R4は低級アルキル、−CH2CH2−COOH、
【式】（R5は低級アルキルを示 す。）を示す。〕 で表わされるキノロン誘導体。[Claims] 1. General formula [In the formula, R represents hydrogen or lower alkyl. R 1 represents hydrogen or forms a single bond with R 2 . R 2 and R 3 represent hydrogen and lower alkyl, respectively. However, R 1 , R 2 , and R 3 are not all hydrogen. R 4 is lower alkyl, −CH 2 CH 2 −COOH,
[Formula] (R 5 represents lower alkyl) is shown. ] A quinolone derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14080178A JPS5566560A (en) | 1978-11-14 | 1978-11-14 | Quinolone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14080178A JPS5566560A (en) | 1978-11-14 | 1978-11-14 | Quinolone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5566560A JPS5566560A (en) | 1980-05-20 |
| JPS631304B2 true JPS631304B2 (en) | 1988-01-12 |
Family
ID=15277047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14080178A Granted JPS5566560A (en) | 1978-11-14 | 1978-11-14 | Quinolone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5566560A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4850993A (en) * | 1986-12-22 | 1989-07-25 | Miles Laboratories, Inc. | Blood bag system incorporating quinolone carboxylic, acid derivatives |
| PL360677A1 (en) * | 2000-10-02 | 2004-09-20 | Janssen Pharmaceutica N.V. | Metabotropic glutamate receptor antagonists |
| MXPA04009435A (en) * | 2002-03-29 | 2005-01-25 | Janssen Pharmaceutica Nv | Radiolabelled quinoline and quinolinone derivatives and their use as metabotropic glutamate receptor ligands. |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5273867A (en) * | 1975-12-18 | 1977-06-21 | Otsuka Pharmaceut Co Ltd | Synthesis of acryl compounds |
| JPS5273866A (en) * | 1975-12-16 | 1977-06-21 | Otsuka Pharmaceut Co Ltd | Synthesis of derivatives of carbostyril or oxyindole |
| JPS5273873A (en) * | 1975-12-16 | 1977-06-21 | Otsuka Pharmaceut Co Ltd | Synthesis of carbostryl derivatives |
| JPS5315387A (en) * | 1976-07-26 | 1978-02-13 | Otsuka Pharmaceut Co Ltd | Novel 3,4-dihydrocarbostyryl derivatives |
-
1978
- 1978-11-14 JP JP14080178A patent/JPS5566560A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5273866A (en) * | 1975-12-16 | 1977-06-21 | Otsuka Pharmaceut Co Ltd | Synthesis of derivatives of carbostyril or oxyindole |
| JPS5273873A (en) * | 1975-12-16 | 1977-06-21 | Otsuka Pharmaceut Co Ltd | Synthesis of carbostryl derivatives |
| JPS5273867A (en) * | 1975-12-18 | 1977-06-21 | Otsuka Pharmaceut Co Ltd | Synthesis of acryl compounds |
| JPS5315387A (en) * | 1976-07-26 | 1978-02-13 | Otsuka Pharmaceut Co Ltd | Novel 3,4-dihydrocarbostyryl derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5566560A (en) | 1980-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0028834B1 (en) | Imidazole-5-acetic acid derivatives, their production and use | |
| JPS582935B2 (en) | 5↓-Production method of aroylpyrrole derivative | |
| GB1580113A (en) | Cycloalkane-substituted phenylacetic acid derivatives their use and preparation | |
| KR960010350B1 (en) | Novel cyclic anthranilic acid derivatives and process for their preparation | |
| US3445473A (en) | 3-anilino-thiophene-4-carboxylic acids,esters,and amides | |
| JPS631304B2 (en) | ||
| Chien et al. | Stereochemistry of Diphenyls. XXXV. 1 The Effect of 3'Substituents on the Rate of Racemization of 2-Nitro-6-carboxy-2'-methoxydiphenyl | |
| CA1211453A (en) | Benzopyran and chroman compounds and process for producing them | |
| US4282360A (en) | 7-Methylthio or methylsulfinyl-5-oxo-5H-thiazolo[2,3-b]quinazoline-2-carboxylic acid | |
| JPS5970681A (en) | 5-substituted 2,3-dihydrobenzofuran-2-carboxylic acids and their derivatives | |
| JPS623145B2 (en) | ||
| US3829446A (en) | Oxobenzofuran intermediates | |
| JP2834506B2 (en) | Novel thienyloxy-alkylamine derivatives, their preparation and medicaments containing this compound | |
| JPS5849369A (en) | Novel imidazole compound, manufacture and analgesic antipuretic antiinflammatory drug containing same as major component | |
| EP0083222A1 (en) | New quinolylacetic acid compounds and pharmaceutical compositions containing them | |
| US3865843A (en) | 4-Oxo-4H-benzo{8 4.5{9 cyclohepta{8 1,2-b{9 thiophene derivatives | |
| US3676463A (en) | Oxobenzofuran carboxamides | |
| US3466277A (en) | N-allylic cyclohexyl lower alkyl normorphines | |
| JPS62169780A (en) | Novel nitrogen arylmethoxy-thiophene derivative and acid addition salt, manufacture and pharmacological blend | |
| US3474112A (en) | Alpha-tetronic acid derivatives | |
| US3649634A (en) | 4-alkoxy-2 3-dihydro-1h-pyrrolo(2.3-b)quinoline compounds | |
| US3862214A (en) | 2-hydroxy-2-(methylsulfonyl)-acetophenone acetates and related compounds | |
| US4312862A (en) | Therapeutically active derivatives of benzamide | |
| US3275689A (en) | 3-alkylsulfonyl-5-(tertiaryaminopropylidene)-and 5-hydroxy-5-(tertiaryaminopropyl)-5h-dibenzo[a, d] cycloheptenes | |
| US3888988A (en) | Oxobenzofuran carboxamides in alleviating inflammation |