SU1579460A3 - Способ получени замещенных 7-амино-3-окси-1-карба(1-детиа)-3-цефем-4-карбоксилата в форме цис-энантиомера - Google Patents

Способ получени замещенных 7-амино-3-окси-1-карба(1-детиа)-3-цефем-4-карбоксилата в форме цис-энантиомера Download PDF

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SU1579460A3
SU1579460A3 SU874202676A SU4202676A SU1579460A3 SU 1579460 A3 SU1579460 A3 SU 1579460A3 SU 874202676 A SU874202676 A SU 874202676A SU 4202676 A SU4202676 A SU 4202676A SU 1579460 A3 SU1579460 A3 SU 1579460A3
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amino
carba
cephem
carboxylate
cis
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Алберт Эванс Дэвид
Брайан Съерген Эрик
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Президент Энд Феллоуз Оф Гарвард Калледж (Фирма)
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    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
    • C07D463/16—Nitrogen atoms
    • C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
    • C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Изобретение касаетс  гетероциклических веществ, в частности получени  замещенных 7-амино-3-окси-1-карба(1-детиа)-3-цефем-4-карбоксилатов (в форме цис-энантиомеров) общей ф-лы R 1C(O)-NH→CH-C(O)-N-C←CH 2-CH 2-C(OH)=C-C(O)-OR 2, где R 1 - C 1 - C 4-алкокси или феноксиметил
R 2 - трет-бутил или N-нитробензилгруппа, в качестве полупродуктов дл  синтеза β-лактамовых антибиотиков. Цель - создание новых полупродуктов указанного назначени . Синтез ведут реакцией гексаметилдисилазанлити  с соединением общей ф-лы R 1-C(O)-NH→CH-C(O)-N[CH 2-C(O)-OR 2-CH←CH 2-CH 2-C(O)-S-C 6H 5, где R 1 и R 2 - см.выше.

Description

Изобретение относитс  к получению новых замещенных 7-амино-3-окси-1-кар- ба (1-детиа)-3-цефем-4-карбоксилата общей формулы
RiCONH.,
COOR
где R4 С(-С43лкокси или феноксиметил;
RZ -трет.бутил- или пара-нитробен- зилгруппа, в форме цис-энантомера, которые могут быть использованы в качестве промежуточных продуктов в синтезе И -лактамовых антибиотиков.
Р
Целью изобретени   вл етс  разработка способа получени  новых соединений , использование которых в ка- честпе промежуточных продуктов позвол ет значительно упростить синтез -лактамовых антибиотиков.
П р им ер. Трет. GVTHTT- /3-трет.- бутилоксикарбониламино-3-окси-1-кар- ба()-3-цефем-4-карбоксилат.
К раствору 4,4 г (9,47 ммоль) 1- -трет-бутилоксикарбонил-метил-3 |3- -трет.бутилоксикарбониламнно-43-(2- -фенил иокарбонилэтил) азетидин-2-она в 100 -ш сухого тетрагидрофурана добавл ли в aTMorr iepe аргогга при -78 С 29,3 мл (3,12 ммоль) гeкcn leтилдиcисл
4j
ы
31
лазанлити . Примерно через 15 мин смесь выпивали в 750 мл водного раст вора хлористого аммони  (50% от насы щений) и устанавливали рН смеси равным 3 с помощью 1 н. сол ной кислоты Подкисленную смесь трижды подвергали экстракции хлористым метиленом порци  ми по 50 мл. Объединенные экстракты промывали рассолом, высушивали над сульфатом натри  и концентрировали путем упаривани . Концентраты подвер
гали хроматографии на двуокиси крем .
ни  с использованием в качестве элю- ента смеси гексана и этилацетата в объемном соотношении 1:1. Элюат упаривали досуха, получа  в ревультате целевое соединение.
Вычислено, %: С 57,61; Н 7,39; N 7,90.
CnHe6N4Oe
Найдено, %: N 7,69.
Масс-спектр:
ИК-спектр и-лактамкарбонил: 1768 .
Аналогично получен п-нитробензиль- ный эфир 7 и-феноксиацетиламино-3- -гидрокси-1-карба(детиа)-3-цефем-4- -карбоновой кислоты.
Вычислено, %: С 59,10; Н 4,53; N 8,99.
С 57,42; Н 7,18; М4 354.
СгэНг,Ы,08
Найдено, %: С 59,10; N 8,96.
Н 4,47;
579460
Масс-спектр (десорбци  полем): М-1 467.
УФ-спектр:у макс 275 нм; б 17,034;
,c269 нм; 6 .
ИК-спектр:А -лактамкарбонил:
1766 смЧ

Claims (1)

  1. Формула изобретени 
    Способ получени  замещенных 7-ами- но-3-окси-1-карба(1-детиа)-3-цефем- -4-карбоксилата общей формулы
    R,CONHv
    СООВг
    где R(- С(-С -алкокси или феноксиметил;
    R - трет-бутил- и пара-нитробен- зилгруппа, в форме цис-эн-антиомера, отличающийс  тем, что со- единение общей формулы
    RiCONH«. CH2CH2COS-(Q
    CH2-COORa
    |где R { и Kg. имеют указанные знач«- 1 ни ,
    подвергают взаимодействию с гексаметилдисилазанпитиеМо
    Редактор А. Долинич
    Составитель И. Бочарова
    Техред Л.Олийнык Корректор М. Самборска 
    Заказ 1925
    Тираж 317
    ВНИИПИ Государственного комитета по изобретени м и открыти м при ГКНТ СССР 113035, Москва, Ж-35, Раушска  наб., д. 4/5
    Подписное
SU874202676A 1985-07-17 1987-06-05 Способ получени замещенных 7-амино-3-окси-1-карба(1-детиа)-3-цефем-4-карбоксилата в форме цис-энантиомера SU1579460A3 (ru)

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US06/755,982 US4665171A (en) 1985-07-17 1985-07-17 Process and intermediates for β-lactam antibiotics

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IE58997B1 (en) 1993-12-15
DE3679002D1 (de) 1991-06-06
CA1310323C (en) 1992-11-17
EP0209352A2 (en) 1987-01-21
JPS6242985A (ja) 1987-02-24
EP0362902A3 (en) 1990-08-01
DK335686D0 (da) 1986-07-15
ES2000516A6 (es) 1988-03-01
AU6016686A (en) 1987-01-22
JPH0762015B2 (ja) 1995-07-05
IE861900L (en) 1987-01-17
AU4793490A (en) 1990-05-10
KR870001193A (ko) 1987-03-12
EP0362902B1 (en) 1996-01-17
JPH07300476A (ja) 1995-11-14
ATE63118T1 (de) 1991-05-15
KR900005257B1 (ko) 1990-07-21
CN1015178B (zh) 1991-12-25
AR243186A1 (es) 1993-07-30
GR861857B (en) 1986-11-18
PT82989B (pt) 1989-01-30
HU201931B (en) 1991-01-28
DK16096A (da) 1996-02-15
EP0209352A3 (en) 1988-04-20
HK1007140A1 (en) 1999-04-01
CN86104783A (zh) 1987-02-04
PT82989A (en) 1986-08-01
DK173456B1 (da) 2000-11-27
EP0362902A2 (en) 1990-04-11
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DE3650474T2 (de) 1996-06-13
JP2634775B2 (ja) 1997-07-30
DK335686A (da) 1987-02-25
DE3650474D1 (de) 1996-02-29
ZA865274B (en) 1988-02-24
AU619938B2 (en) 1992-02-06
EP0209352B1 (en) 1991-05-02
HU906465D0 (en) 1991-04-29
US4665171A (en) 1987-05-12
ATE133172T1 (de) 1996-02-15
AU595216B2 (en) 1990-03-29
RU1794079C (ru) 1993-02-07
HUT41786A (en) 1987-05-28
NZ216871A (en) 1989-10-27
IL79420A (en) 1992-01-15

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