JPS62178586A - Quinoline-3-carboxylic acid derivative - Google Patents
Quinoline-3-carboxylic acid derivativeInfo
- Publication number
- JPS62178586A JPS62178586A JP1675886A JP1675886A JPS62178586A JP S62178586 A JPS62178586 A JP S62178586A JP 1675886 A JP1675886 A JP 1675886A JP 1675886 A JP1675886 A JP 1675886A JP S62178586 A JPS62178586 A JP S62178586A
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- quinoline
- acid
- acid derivative
- lower alkyl
- 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.)
- Pending
Links
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012320 chlorinating reagent Substances 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- ZFZDZXYWJALBDT-UHFFFAOYSA-N 7-(4-acetyl-3-methylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C(C)=O)C(C)C1 ZFZDZXYWJALBDT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- -1 butyroyl group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring 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
- MGJXIOXOKWLZFS-UHFFFAOYSA-N 1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=CC=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MGJXIOXOKWLZFS-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WWAICNVVDGLNFR-UHFFFAOYSA-N CCN1C=C(C(=O)C2=CC(=C(C(=C21)Cl)N3CCN(C(C3)C)C(=O)C)F)C(=O)O Chemical compound CCN1C=C(C(=O)C2=CC(=C(C(=C21)Cl)N3CCN(C(C3)C)C(=O)C)F)C(=O)O WWAICNVVDGLNFR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910001389 inorganic alkali salt Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
光１目と１狛一
本発明は優れた抗菌作用を有する新規なキノリン−３−
カルボン酸誘導体、及びその薬理学的に許容しつる塩に
関するものである。[Detailed description of the invention] The present invention is a novel quinoline-3-
This invention relates to carboxylic acid derivatives and pharmacologically acceptable salts thereof.
１肚へ１腹
更に詳しく言えば、本発明は一般式（Ｉ）（式中、Ｒ１
は低級アルキル基を、Ｒ２は水素原子又は低級アルカノ
イル基を％Ｒ３は低級アルキル基を表わす。）
で示される新規なキノリン−３−カルボン酸誘導体、及
びその薬理学的に許容しつる塩に関する。More specifically, the present invention relates to the general formula (I) (wherein R1
represents a lower alkyl group, R2 represents a hydrogen atom or a lower alkanoyl group, and %R3 represents a lower alkyl group. ) and a pharmacologically acceptable salt thereof.
本発明の前記一般式（Ｉ）中、Ｒ１及びＲ３で示される
低級アルキル基としては、たとえば、メチル基、エチル
基、プロピル基、ブチル基等が、又、Ｒ２で示される低
級アルカノイル基としては、たとえば、ホルミル基、ア
セチル基、プロパノイル基、ブチロイル基等が挙げられ
る。In the general formula (I) of the present invention, examples of the lower alkyl group represented by R1 and R3 include a methyl group, ethyl group, propyl group, butyl group, and examples of the lower alkanoyl group represented by R2. Examples include formyl group, acetyl group, propanoyl group, butyroyl group, and the like.
本発明の前記一般式（Ｉ）で示される化合物の薬理学的
に許容しろる塩としては、酸付加塩又はアルカリ付加塩
が挙げられ、酸付加塩としては、たとえば、塩酸、臭化
水素酸、ヨウ化水素酸、硝酸、硫酸、燐酸等の鉱酸塩、
あるいは、酢酸、マレイン酸、フマール酸、クエン酸、
シュウ酸、酒石酸等の有機酸塩が、アルカリ付加塩とし
ては、たとえば、ナトリウム、カリウム、カルシウム。Examples of the pharmacologically acceptable salts of the compound represented by the general formula (I) of the present invention include acid addition salts and alkali addition salts. Examples of the acid addition salts include hydrochloric acid, hydrobromic acid , mineral acid salts such as hydroiodic acid, nitric acid, sulfuric acid, phosphoric acid,
Alternatively, acetic acid, maleic acid, fumaric acid, citric acid,
Organic acid salts such as oxalic acid and tartaric acid are used as alkali addition salts such as sodium, potassium, and calcium.
アンモニウム等の無機アルカリ塩、あるいはエタノール
アミン、Ｎ、Ｎ−ジアルキルエタノールアミン等の有機
塩基の塩等が挙げられる。Examples include inorganic alkali salts such as ammonium, and salts of organic bases such as ethanolamine and N,N-dialkylethanolamine.
本発明の前記一般式（Ｉ）で示される新規なキノリン−
３−カルボン酸誘導体は、次の方法により製造すること
ができる。A novel quinoline represented by the general formula (I) of the present invention
The 3-carboxylic acid derivative can be produced by the following method.
本発明に係わる化合物の製造方法の第一の様式によれば
、前記一般式（Ｉ）で示される化合物は、次の一般式（
ｎ）
わす。）
で示されるキノリン−３−カルボン酸誘導体の８位を直
接クロル化することにより製造することができる。According to the first mode of the method for producing a compound according to the present invention, the compound represented by the general formula (I) is produced by the following general formula (
n) Wasu. ) It can be produced by directly chlorinating the 8-position of the quinoline-3-carboxylic acid derivative shown in the formula.
本発明の方法において使用されるクロル化剤としては、
塩素、スルフリルクロライド等が挙げられる。The chlorinating agent used in the method of the present invention includes:
Examples include chlorine and sulfuryl chloride.
又、溶媒としては、たとえば、メタノール、エタノール
、プロパツール等のアルコール類、及ヒクロロホルム、
ジクロロメタン、酢酸等が挙げられ、反応は水冷下から
２００℃の範囲で行われる。In addition, as a solvent, for example, alcohols such as methanol, ethanol, propatool, and chloroform,
Examples include dichloromethane and acetic acid, and the reaction is carried out at a temperature ranging from water cooling to 200°C.
本発明に係わる化合物の製造方法の第二の様式によれば
、前記一般式（Ｉ）で示される化合物のうちＲ２が低級
アルカノイル基である次の一般式（式中、Ｒ１及びＲ３
は前述と同意義を表わす。）で示される低級アルカノイ
ル基を有するキノリン−３−カルボン酸誘導体を、加水
分解することにより製造することができる。According to the second mode of the method for producing a compound according to the present invention, the following general formula (wherein R1 and R3
represents the same meaning as above. ) can be produced by hydrolyzing a quinoline-3-carboxylic acid derivative having a lower alkanoyl group.
加水分解はそれ自体公知の方法で、酸又はアルカリを用
いて行われ、酸性加水分解には塩酸、硫酸等の酸を用い
、アルカリ性加水分解には水酸化ナトリウム、水酸化カ
リウム等のアルカリを用いこれら酸又はアルカリの水溶
液、もしくはエタノール、メタノール等の溶液として、
あるいは含水何機溶媒による溶液として反応に用いるこ
とができる。Hydrolysis is carried out using an acid or alkali using a method known per se. For acidic hydrolysis, an acid such as hydrochloric acid or sulfuric acid is used, and for alkaline hydrolysis, an alkali such as sodium hydroxide or potassium hydroxide is used. As an aqueous solution of these acids or alkalis, or a solution of ethanol, methanol, etc.
Alternatively, it can be used in the reaction as a solution in a water-containing solvent.
又、反応は室温から溶媒の加熱還流温度下において行わ
れる。Further, the reaction is carried out at a temperature ranging from room temperature to the temperature at which the solvent is heated to reflux.
１匪立肱ｌ
この様にして製造される前記一般式（Ｉ）で示される新
規なキノリン−３−カルボン酸誘導体、及びその薬理学
的に許容しうる塩は、ダラム陽性菌、ダラム陰性菌に対
し広い抗菌作用を有し、医薬として極めて有用である。1. The novel quinoline-3-carboxylic acid derivative represented by the general formula (I) and its pharmacologically acceptable salt produced in this manner can be used for Durum-positive bacteria and Durum-negative bacteria. It has a wide range of antibacterial effects and is extremely useful as a medicine.
この様にして製造される前記一般式（Ｉ）で示される新
規なキノリン−３−カルボン酸誘導体、及びその薬理学
的に許容しつる塩は、常法により、錠剤、散剤、カプセ
ル剤、注射剤又は外用剤等の製剤とすることができ、経
口又は非経口投与することにより臨床に供される。投与
量は治療すべき症状及び投与方法により左右されるが成
人に経口投与する場合で、通常１回５０〜１０００■ｇ
であ以下、本発明を実施例によって説明する。The novel quinoline-3-carboxylic acid derivative represented by the general formula (I) and its pharmacologically acceptable salts produced in this way can be prepared into tablets, powders, capsules, injections, etc. by conventional methods. It can be made into a preparation such as a drug or an external preparation, and is clinically administered by oral or parenteral administration. The dosage depends on the symptoms to be treated and the administration method, but when administered orally to adults, it is usually 50 to 1000 g at a time.
The present invention will now be explained by way of examples.
実施例１
７−（４−アセチル−３−メチル−１−ピペラジニル）
−８−１０ロー１−エチル−６−フルオロ−１，４−ジ
ヒドロ−４−オキソキノリン−３−カルボン酸
７−（４−アセチル−３−メチル−１−ピペラジニル）
−１−エチル−６−フルオロ−１，４−ジヒドロ−４−
オキソキノリン−３−カルボン酸２．５ｇのクロロホル
ム１５０１溶液を室温撹拌下スルフリルクロリド１．８
１を滴下する。同温で５分間撹拌した後、水３０■ｌを
加える。クロロホルムを分液し、水洗、脱水する。溶媒
を留去し、残渣にメタノールを加えて析出結晶をろ取し
、淡黄色結晶２．５ｇを得る。クロロホルム−メタノー
ルから再結晶して、融点２６２〜２８３′の淡黄色粉末
品を得る。Example 1 7-(4-acetyl-3-methyl-1-piperazinyl)
-8-10Rho 1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 7-(4-acetyl-3-methyl-1-piperazinyl)
-1-ethyl-6-fluoro-1,4-dihydro-4-
A solution of 2.5 g of oxoquinoline-3-carboxylic acid in 1501 chloroform was mixed with 1.8 g of sulfuryl chloride while stirring at room temperature.
Drip 1. After stirring for 5 minutes at the same temperature, 30 μl of water was added. Separate the chloroform, wash with water, and dehydrate. The solvent was distilled off, methanol was added to the residue, and the precipitated crystals were collected by filtration to obtain 2.5 g of pale yellow crystals. Recrystallization from chloroform-methanol gives a pale yellow powder with a melting point of 262-283'.
元素分析値 Ｃ１９Ｈ２□ＣＩＦＮ３０４理論値 Ｃ，
５５，６８ｉＨ，５，１１Ｎ、１０．２５実験値 Ｃ，
５５，７ＢｉＨ，５，４０； Ｎ、菫ｏ、ｉ。Elemental analysis value C19H2□CIFN304 theoretical value C,
55,68iH, 5,11N, 10.25 experimental value C,
55,7BiH,5,40; N, Sumio, i.
実施例２
７−（３−メチル−１−ピペラジニル）−８−クロロ−
１−エチル−〇−フルオロー１． ４−ジヒドロ−４−
オキソキノリン−３−カルボン酸７−（４−アセチル−
３−メチル−１−ピペラジニル）−８−クロロ−１−エ
チル−６−フルオロ−１，４−ジヒドロ−４−オキソキ
ノリン−３−カルボン酸２．０ｇ、３．８％ＮａＯＨ水
５０１の水金０１１５時間加熱還流する。冷機希塩酸で
中和し、析出沈殿物をろ去する。ろ液を希塩酸で酸性と
し、クロロホルムで洗浄する。水層をＮａＯＨ水で中和
し、クロロホルムで抽出する。Example 2 7-(3-methyl-1-piperazinyl)-8-chloro-
1-ethyl-〇-fluoro1. 4-dihydro-4-
Oxoquinoline-3-carboxylic acid 7-(4-acetyl-
3-Methyl-1-piperazinyl)-8-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 2.0 g, 3.8% NaOH water 501% water Heat to reflux for 0.115 hours. Neutralize with cold dilute hydrochloric acid and filter off the precipitate. The filtrate is acidified with dilute hydrochloric acid and washed with chloroform. The aqueous layer is neutralized with aqueous NaOH and extracted with chloroform.
クロロホルム層は留去し、残渣にメタノールを加えて析
出結晶をろ取し、淡黄色結晶を０．９５ｇ得る。クロロ
ホルム−エタノールから再結晶して、融点２１６〜２１
７° （分解）の淡黄色粉末品を得る。The chloroform layer was distilled off, methanol was added to the residue, and the precipitated crystals were collected by filtration to obtain 0.95 g of pale yellow crystals. Recrystallized from chloroform-ethanol, melting point 216-21
A pale yellow powder product of 7° (decomposition) is obtained.
Claims (1)
又は低級アルカノイル基を、Ｒ＿３は低級アルキル基を
表わす。） で示されるキノリン−３−カルボン酸誘導体、及びその
薬理学的に許容しうる塩。[Claims] Represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 represents a lower alkyl group, R_2 represents a hydrogen atom or a lower alkanoyl group, and R_3 represents a lower alkyl group.) quinoline-3-carboxylic acid derivatives and pharmacologically acceptable salts thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1675886A JPS62178586A (en) | 1986-01-30 | 1986-01-30 | Quinoline-3-carboxylic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1675886A JPS62178586A (en) | 1986-01-30 | 1986-01-30 | Quinoline-3-carboxylic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62178586A true JPS62178586A (en) | 1987-08-05 |
Family
ID=11925133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1675886A Pending JPS62178586A (en) | 1986-01-30 | 1986-01-30 | Quinoline-3-carboxylic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62178586A (en) |
-
1986
- 1986-01-30 JP JP1675886A patent/JPS62178586A/en active Pending
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