SU1052507A1 - Смесь 1,3- и 1,2-бис-/ди-н-пропилацетат/глицерина,обладающа противосудорожной активностью - Google Patents

Смесь 1,3- и 1,2-бис-/ди-н-пропилацетат/глицерина,обладающа противосудорожной активностью Download PDF

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SU1052507A1
SU1052507A1 SU813276796A SU3276796A SU1052507A1 SU 1052507 A1 SU1052507 A1 SU 1052507A1 SU 813276796 A SU813276796 A SU 813276796A SU 3276796 A SU3276796 A SU 3276796A SU 1052507 A1 SU1052507 A1 SU 1052507A1
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mixture
bis
glycerin
propylacetate
antispasmodic effect
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SU813276796A
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Шиняк Мишель
Грэн Клод
Жаммо Фернар
Пижероль Шарль
Эймар Пьер
Ферранде Бернар
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Санофи (Фирма)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Psychiatry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Смесь,3-й 1,2-бис-(ди-Н-пропилацетат )-глицерина формулы Н2-1 Н-€Н2 ( Н9 eee€ii(it-«sH,)2 CHa-iiH-CHj ()етС9 о он ШК{к-€ Щ)г :в отношении 1,43-1,54, обладающа  противосудорОжной активностью.

Description

Изобретение относитс  к новому соединению - смеси 1,3- и 1,2-бис- (ди-ч-пропилацетат)-глицерина,обладак цей противосудорожной активностью . S Известна 5-этил-5-феннлбарбитур ва  кислота .(фенобарбитал), формулы ,. 1ГИ-СО CjHj оОладаюшее противосудорожной актив ностыо OQ . Однако это соединение обладает также сильным снотворньм действием Цель изобретени  - расширеиие а сенала средств воздействи  на живо организм., Поставленна  цель достигаетс  новьм соединением - сжесью 1,3- и 1,2-бис-(ди-й-пропилацетат)-глицерина ( ) НО ве0Ш(«7С5Нг)г .. . - CRz-fH-CHe {«-(jH7)jeHeco j н еоснСк-СаН Ь : В отношении 1/43-1 54, обладающей противосудорожной активностью. Данное соединение получают в,заимодействием галоидного алкйла с на риевой солью карбоновой кислоты по способу 21, а именно, 1,3-дихлорпропанола-х с ди-н-пропилацетатом натри , в присутствии основани . Полученна  смесь обеспечивает постепенное и медленное выделение ди-Н-пропилуксуснрй кислоты (называемой также вальпроиновой кислотой котора  представл ет собой известное прйтивоэлилептическое средство Таким образом, данна  смесь  вл етс  пронар котиком ди-Н-пропилуксусной кислоты. Смесь Получают следукхцйм образом В двухлитровую колбу, снабженную обратным холодильникс 4, помещают 893 г (900 мл) 11,11-диметилформамида , 77,4 г (0,6 моль| 1,3-дихлорпропанола-2 и 206,4г (1,24 моль:) Ди-Ц-пропилацетата натри . При осторожном перемешивании в атмосфере азота смесь нагревают до , затем выдерживают при этой температуре 8 ч, после чего отгон ют при давлении 20 лм рт.ст. 893 г дистилл та. К остатку прибавл ют 300 мл дистилли|рованной водш и 537 г (620 мл) толуола , водную фазу отдел ют, органкч&ску npoMbmaioT последовательно 300 мл дистиллированной вод:рл,растворс и 30 г карбоната натри  в 400 мл воды и несколькими порци ми дистиллированной вода по 300 мл получени  нейтральной реакции (рН). Затем высушивают над сульфатом натри , отгон ют растворитель при Пониженном давлении в роторе, получают сырую смесь конечных Продуктов, 201 г, выход 97,3%, Смесь ректифицируют в вакуз , отбира  фракцию, имеющую (0,2 мм.рт.ст., Пр 1,4476, отношение 1еЗ-изомера к 1,2-бис-(ди м-пропилацетат) глицерину , равно 1,54, количество 1-ди-н-пропилацетата глицерина - 1%, три-(ди-Н-пропилацетата)глицерина не Обнаружено, исходного 1,3-дихлорпропанола-2 - 0,002%. При использовании полученной смеси (при оральной дозе 1000 мг) врем  полураспада выдел емой из нее ди-й-пропилуксусиой кислота составл ет 20   20 мии , что значительно вышег чем при использовани  натриевой сОли ди-Н-пропиЛуксусной кислоты - 11 ч 35 мин. Данна  смесь обладает повышенной противосудорожной активностью, так как приводит к более стабильжжу терапевтическому уррвню ди-н-ПРОПИЛуксусной кислоты в крови. Кроме того, она имеет низкую токсичность . 7ак, крыс при оральнс введении - 5000 мг/кг,при интраперитональном введении 2368 мг/кг; LD fo дл  мьаией - при оральном введении - 5597 мг/кг, при интраперитональном введении 1920 мг/кг.

Claims (1)

  1. Смесь1,3- и 1,2-бис-(ди-Н-пропилацетат)-глицерина формулы ен2-ен-сн2 не 0СО€н(«-еэн7)2 и СНо-СН-ОНв I 2 I I 2 (и-СэН7)2СН0<50 о ОН соон(к-еэн7)2 в отношении 1,43-1, 54, обладают противосудорожной активностью.
SU813276796A 1979-03-06 1981-05-04 Смесь 1,3- и 1,2-бис-/ди-н-пропилацетат/глицерина,обладающа противосудорожной активностью SU1052507A1 (ru)

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SU802891303A SU1195901A3 (ru) 1979-03-06 1980-03-05 Способ получени смесей производных глицерина
SU813276796A SU1052507A1 (ru) 1979-03-06 1981-05-04 Смесь 1,3- и 1,2-бис-/ди-н-пропилацетат/глицерина,обладающа противосудорожной активностью
SU833568904A SU1225481A3 (ru) 1979-03-06 1983-03-29 Способ получени смеси глицерил-1,2-и 1,3-бис/ди-н-пропилацетатов/,про вл ющей свойства депрессанта центральной нервной системы

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MY8500075A (en) 1985-12-31
HU188840B (en) 1986-05-28
ZA801081B (en) 1981-03-25
GR70703B (ru) 1983-01-04
ES8103015A1 (es) 1981-02-16
IL59407A0 (en) 1980-05-30
SU1195901A3 (ru) 1985-11-30
YU42064B (en) 1988-04-30
DE3061960D1 (en) 1983-03-24
PL124023B1 (en) 1982-12-31
NO800626L (no) 1980-09-08
OA06568A (fr) 1981-08-31
IN152492B (ru) 1984-01-28
SU1225481A3 (ru) 1986-04-15
DD151931A5 (de) 1981-11-11
CA1162928A (en) 1984-02-28
NZ192944A (en) 1984-07-06
FI800683A (fi) 1980-09-07
PT70904A (en) 1980-04-01
ES489250A0 (es) 1981-02-16
IE49539B1 (en) 1985-10-30
DK93880A (da) 1980-09-07
FI69449C (fi) 1986-02-10
NO152899C (no) 1985-12-11
CY1209A (en) 1983-12-31
NO152899B (no) 1985-09-02
YU41699B (en) 1987-12-31
AU5587280A (en) 1980-09-11
SG61583G (en) 1985-02-15
HU183072B (en) 1984-04-28
FI69449B (fi) 1985-10-31
US4423071A (en) 1983-12-27
HK22384A (en) 1984-03-23
IE800445L (en) 1980-09-06
CS216526B2 (en) 1982-11-26
IL59407A (en) 1983-12-30
JPS6315256B2 (ru) 1988-04-04
EP0018342B1 (fr) 1983-02-16
AU534007B2 (en) 1983-12-22
EP0018342A1 (fr) 1980-10-29
AR224394A1 (es) 1981-11-30
JPS55141436A (en) 1980-11-05
PL222446A1 (ru) 1981-01-30
YU292382A (en) 1983-09-30
DD158773A5 (de) 1983-02-02
YU61580A (en) 1983-04-30

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