SU1015827A3 - Process for preparing derivatives of quinoline carboxylic acid or their hydrates - Google Patents

Process for preparing derivatives of quinoline carboxylic acid or their hydrates Download PDF

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SU1015827A3
SU1015827A3 SU813254244A SU3254244A SU1015827A3 SU 1015827 A3 SU1015827 A3 SU 1015827A3 SU 813254244 A SU813254244 A SU 813254244A SU 3254244 A SU3254244 A SU 3254244A SU 1015827 A3 SU1015827 A3 SU 1015827A3
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carboxylic acid
quinoline carboxylic
hydrates
alkyl
compounds
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SU813254244A
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Ирикура Цутому
Кога Хироси
Муралма Сатоси
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Киорин Сейяку Кабусики Кайся (Фирма)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

Certain novel quinoline carboxylic acid derivatives, being the compounds of the general formula: <IMAGE> (wherein R2 is halogen; R3 is a 1- piperazinyl or 4-(C1-C5)alkyl- piperazinyl; and either R1 is (C1-C5) alkyl and R4 is halogen or (C1-C5) alkyl, or R1 and R4 are each alkylene and together form a 5 or 6 membered ring which may be substituted by a (C1-C5) alkyl radical) and the hydrates and salts thereof, possess good anti-bacterial activity against both gram-negative and gram-positive bacteria. They may be prepared by reacting a corresponding 7-halo quinoline carboxylic acid derivative with a compound of formula R3H. The 7-halo quinoline carboxylic acid derivatives employed as starting materials are novel compounds which may be prepared by processes analogous to known processes.

Description

Сосш.Sass.

В, AT,

(II)(Ii)

где R -Rа указаны выше, ;С формальдегидом в присутствии муравьиной кислоты с выделением целевого продукта в свободноч виде или IB виде гидратов.where R -Ra is indicated above; With formaldehyde in the presence of formic acid with the release of the target product in free form or IB form of hydrates.

Пример. 1-Этил-б,8-дифтор1 ,4-ДИГИДРО-4-ОКСО-7-(4-метилпиперазино )-хинолин-3-карбонова  кислота Example. 1-Ethyl-b, 8-difluoro1, 4-DIGIDRO-4-OXO-7- (4-methylpiperazino) -quinoline-3-carboxylic acid

Смешивают гидрохлорид 1-этил-б,8дифтор-1 ,4-дигидро-4-оксо-7-пиперазинохинолин-3-карбоновой кислоты (0,7.5 г), формиат натри  (0,27 г), 87%-ную мура1вьиную кислоту (4 мл) и 37%-ный раствор формальдегида (.4 мл) и смесь кип т т в течение 5 ч. Реакционную смесь выпаривают. К остатку добавл ют воду (10 мл), рН раствора довод т до 7 с помощью 10%-ного раствора едкого натра и экстрагируют дихлорметаном. Органический слой промывают водой, сушат безводным сульфатом натри  и выпаривают. Остаток перекристаллизовывают из смеси диметилформамида (ДМД) и этанола, в результате чего получают 6,45 г 1-этил-б,8-дифтор 1,4-ДИГИДРО-4-ОКСО-7-(4-метилпиперазино )-хинолин-3-к рбоновой кислоты в ви,це бесцветных кристаллов. Т.пл. 245-24бс.Hydrochloride 1-ethyl-b, 8-difluoro-1, 4-dihydro-4-oxo-7-piperazinoquinoline-3-carboxylic acid (0.7.5 g), sodium formate (0.27 g), 87% muravine acid are mixed (4 ml) and 37% formaldehyde solution (.4 ml) and the mixture is boiled for 5 hours. The reaction mixture is evaporated. Water (10 ml) is added to the residue, the pH of the solution is adjusted to 7 with 10% sodium hydroxide solution and extracted with dichloromethane. The organic layer is washed with water, dried with anhydrous sodium sulfate, and evaporated. The residue is recrystallized from a mixture of dimethylformamide (DMD) and ethanol, resulting in 6.45 g of 1-ethyl-b, 8-difluoro 1,4-DIGIDRO-4-OXO-7- (4-methylpiperazino) -quinoline-3- to carboxylic acid in vi, tse colorless crystals. M.p. 245-24bs.

Вычислено, % С 58,11; Н 5,.45; К 11,86Calculated,% C 58.11; H 5, .45; K 11.86

С,, H.C ,, H.

Найдено,%i С 57,57; Н5,48 12,02Found,% i C 57,57; H5.48 12.02

П р и м е р 2. 9-Фтор-6,7-дигидро-5-метил-1-оксо-8- (4-метилпиперазино )-1Н, 5Н-бензо (ij) хинолизин-2карбонова  кислота.EXAMPLE 2 9-Fluoro-6,7-dihydro-5-methyl-1-oxo-8- (4-methylpiperazino) -1H, 5H-benzo (ij) quinolizin-2carboxylic acid.

Смесь гидрохлорида 9-фтор-б,7-ди5 гидро-5-метил-1-оксо-8-пиперазино-1Н, 5Н-бензо (ij) хинолизин-2-карбоновой кислоты (0,9 г), формиата натри  (0,64 г), 87%-ной муравьиной кислоты (5 мл) и 37%-ного раствора формальдегида (5 мл) кип т т в течение 5 ч. Смесь выпаривают досуха и добавл ют водный раствор едкого натра, щелочной раствор нейтрализуют уксусной кислотой и экстрагируют дихлормета 5 ном. Органический слой промывают водой , сушат безводным сульфатом натри  и выпаривают. Твердый остаток перекристаллизовывают из смеси ДМФ и этанола и получают 0,70 г 9-фтор6 ,7-дигидро-5-метил-1-оксо-8-(4-метилпипераэино )-1Н,5Н-бензо (ij) хинолизин-2-карбоновой кислоты в виде бесцветных игольчатых кристаллов. Т.пл. 261-2бЗс.A mixture of 9-fluoro-b, 7-di5 hydro-5-methyl-1-oxo-8-piperazino-1H, 5H-benzo (ij) quinolizin-2-carboxylic acid hydrochloride (0.9 g), sodium formate (0 , 64 g), 87% formic acid (5 ml) and 37% formaldehyde solution (5 ml) are boiled for 5 hours. The mixture is evaporated to dryness and an aqueous solution of sodium hydroxide is added, the basic solution is neutralized with acetic acid and extracted with dichloromethane 5 Nom. The organic layer is washed with water, dried with anhydrous sodium sulfate, and evaporated. The solid residue is recrystallized from a mixture of DMF and ethanol to obtain 0.70 g of 9-fluoro 6, 7-dihydro-5-methyl-1-oxo-8- (4-methyl-piperaeno) -1H, 5H-benzo (ij) quinolizin-2- carboxylic acid in the form of colorless needles. M.p. 261-2bZs.

Вычислено, %: С 63,50; Н 6,17; N 11,69Calculated,%: C 63.50; H 6.17; N 11.69

C gHjaO NjFC gHjaO NjF

Найдено, %: С 63,45; Н 6,20; N 11,65Found,%: C 63.45; H 6.20; N 11.65

П р и м е р 3. 8-Хлор-1-этил-60 фтор-1,4-ДИГИДРО-4-ОКСО-7-(4-метилпиперазино )-хинолин-3-карбонова н кислота.Example 3: 8-Chloro-1-ethyl-60 fluoro-1,4-DIHIDRO-4-OXO-7- (4-methylpiperazino) -quinoline-3-carboxylic acid.

Гидрохлорид 8-хлор-1-этил-6-фтор1 ,4-дигидро-4-оксо-7-пиперазинохи5 нолин-3-карбоновой кислоты (0,25 г), формиат натри . (0,5 г), 87%-ную муравьиную кислоту (5 мл) и 37%-ный раствор формальдегида (5 мл) смешивают и кип т т в течение 6,5 ч. 0 Раствор упаривают и подщелачивают водным раствором едкого наТра. Щелочной раствор нейтрализуют уксусной кислотой, экстрагируют дихлорметаном и выпаривают. Остаток перекристалли зовывают из этанола, в результате чето получают 0,21 г 8-хлор-1-этил-6фтор-1 , 4-дигидро- 4-оксо-7- (4-метилпиперазино )хинолин-3-карбоновой кислоты в иде бесцветного порошка. Т.пл. 213-216С.Hydrochloride 8-chloro-1-ethyl-6-fluoro1, 4-dihydro-4-oxo-7-piperazinoch5 nolin-3-carboxylic acid (0.25 g), sodium formate. (0.5 g), 87% formic acid (5 ml) and 37% formaldehyde solution (5 ml) are mixed and boiled for 6.5 hours. 0 The solution is evaporated and basified with an aqueous solution of caustic hydrochloride. The alkaline solution is neutralized with acetic acid, extracted with dichloromethane and evaporated. The residue is recrystallized from ethanol, and as a result, 0.21 g of 8-chloro-1-ethyl-6fluoro-1, 4-dihydro-4-oxo-7- (4-methylpiperazino) quinoline-3-carboxylic acid is ideally colorless. powder. M.p. 213-216C.

0 Вычислено,%: С 54,84; Н 5,28; N 11,290 Calculated,%: C 54.84; H 5.28; N 11.29

С„ Н.,р О, N э F- С1 1/4 HjO Найдено, %: С 54,98; Н 5,20; N 11,14C „N., p O, N e F-C1 1/4 HjO Found,%: C 54.98; H 5.20; N 11.14

5 Эксперимент 1. Антибактериальное действие (in vitro).5 Experiment 1. Antibacterial action (in vitro).

Антибактериальное действие соединений данного изобретени  оценивают 0 с помощью стандартного метода агарового разбавлени  против грамположительных и грамотрицательных бактерий,The antibacterial effect of the compounds of this invention is assessed by 0 using a standard agar dilution method against gram-positive and gram-negative bacteria,

Полученные результаты в сравнении с данными дл  известных соединений 5 представлены в табл. 1.The results obtained in comparison with the data for known compounds 5 are presented in table. one.

3101582731015827

Антибактериальное действиеAntibacterial action

ТаблицаTable

Соединени  npHMejjoB 1,2 и 3 более активны/ чем налидиксинова  кислота и пипемидинова  кислота про тив грамположительных и грамотрицательных бактерий.Compounds npHMejjoB 1,2 and 3 are more active / than nalidixic acid and pimemidinic acid against gram-positive and gram-negative bacteria.

Эксперимеит 2. Антибактериальное действие (in vivo). Сравнительное действие соединений примеров NA, РРА и MZX против cHCTeMHiax пораженийExperiment 2. Antibacterial action (in vivo). Comparative effect of compounds of examples NA, PPA and MZX against cHCTeMHiax lesions

Антибактериальное действие соединений примеров 1 и 2 in vivo определ ют методом системных заражений.The antibacterial effect of the compounds of examples 1 and 2 in vivo is determined by the method of systemic infections.

Результаты испытаний представлены в табл. 2 в сравнении с данными дл  АМ-715, налидиксиновой кислоты (NA), пипемидиновой кислоты (РРА) И милоксацина (MZX). Таблица2 2,3 н 6 АМ-715, , The test results are presented in Table. 2 in comparison with those for AM-715, nalidixic acid (NA), pimemidinic acid (PPA), and myloxacin (MZX). Table2 2.3 n 6 AM-715,,

1-Этил-6-фтор-1,4-дигидро-7-пиперазиноСистемные заражени  провод т на мышиных мужских особ х (весом 20 ±) внутрибрюшинным способом с помощью суспензий следунщих испытуемых штаммов в 0,5 мл выт жкицентральной части мозга, содержащей 5% муцина: Pseudomonas aeruginosa GNU 187,3,Эх xlO кнеток, Staphylococcus aureus Smith 3,0x10 клеток. Serratia mar cescens GN 7577, 2, 2x10 клеток. Препараты ввод г мышам орально дважды в день, сразу и через 4 ч после заражени , терапевтическое действие препаратов оценивают по выживаемости Сравнение антибактериального действи  in vivo провод т на основе средней эффективной дозы (ЕДур), рассчитанной по данным анализа проб. Антибактериальное действие in vivo соединений примеров 2,3 и б значительно больше, чем активность соедидинений АМ-715, РРА и милоксацина против системных заражений мышей каждым типом бактерий. 4-рксохинолин-3-карбонова  кислота,1-Ethyl-6-fluoro-1,4-dihydro-7-piperazino System infections were carried out on mouse male individuals (weighing 20 ±) by the intraperitoneal method using suspensions of the following test strains in 0.5 ml of the brain’s central brain containing 5 % mucin: Pseudomonas aeruginosa GNU 187.3, Ex xlO knetok, Staphylococcus aureus Smith 3,0x10 cells. Serratia mar cescens GN 7577, 2, 2x10 cells. Drugs administered to mice orally twice a day, immediately and 4 hours after infection, the therapeutic effect of the drugs is evaluated by survival. Comparison of the antibacterial effect in vivo is based on the average effective dose (EDur) calculated according to sample analysis. The in vitro antibacterial action of the compounds of Examples 2.3 and B is significantly greater than the activity of AM-715, PPA and miloxacin compounds against systemic infection of mice with each type of bacteria. 4-rxoquinoline-3-carboxylic acid,

Claims (1)

Способ получения производных хинолинкарбоновой кислоты общей формулы о в» Κι где R-C2 Hg-, 'The method of obtaining derivatives of quinolinecarboxylic acid of the General formula o in "Κι where RC 2 Hg-, ' R-i-F, .R-i-F,. Rg-F или Cl или R^+Rз представляют собой -СНг-СН г-СН-СН3, или их гидратов,, отличающийся тем, что соединение общей формулы подвергают взаимодействию с формаль- с .дегидом в присутствии муравьиной ф кислоты с выделением целевого продук·] та в свободном виде или в виде его гидратов.Rg-F or Cl or R ^ + Rz are —CH g —CH g —CH — CH 3 , or hydrates thereof, characterized in that the compound of the general formula is reacted with formaldehyde in the presence of formic acid f with the selection of the target product ·] that in free form or in the form of its hydrates.
SU813254244A 1979-08-22 1981-03-03 Process for preparing derivatives of quinoline carboxylic acid or their hydrates SU1015827A3 (en)

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Application Number Priority Date Filing Date Title
JP10677679A JPS5630964A (en) 1979-08-22 1979-08-22 Novel substituted quinolinecarboxylic acid and its preparation
BE2/58706A BE884824A (en) 1979-08-22 1980-08-19 QUINOLEINE-CARBOXYLIC ACID DERIVATIVES AND PROCESS FOR THEIR PREPARATION
BE2059018 1981-02-19

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DE3031767C2 (en) 1994-04-14
HU184817B (en) 1984-10-29
AU6112280A (en) 1981-02-26
SE440353B (en) 1985-07-29
IT8024111A0 (en) 1980-08-11
SU978727A3 (en) 1982-11-30
ES8104233A1 (en) 1981-04-16
JPS5630964A (en) 1981-03-28
SG71386G (en) 1987-03-27
CA1159454A (en) 1983-12-27
HK98486A (en) 1986-12-24
MY8700155A (en) 1987-12-31
ES494352A0 (en) 1981-04-16
BE884824A (en) 1980-12-16
GB2057440B (en) 1983-10-12
AU533141B2 (en) 1983-11-03
IT1132392B (en) 1986-07-02
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GB2057440A (en) 1981-04-01
DE3031767C3 (en) 1994-04-14

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