SU483830A3 - Способ получени 7-ациламиноцефалоспоринов - Google Patents

Способ получени 7-ациламиноцефалоспоринов

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Publication number
SU483830A3
SU483830A3 SU691342468A SU1342468A SU483830A3 SU 483830 A3 SU483830 A3 SU 483830A3 SU 691342468 A SU691342468 A SU 691342468A SU 1342468 A SU1342468 A SU 1342468A SU 483830 A3 SU483830 A3 SU 483830A3
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USSR - Soviet Union
Prior art keywords
acid
added
lactam
ether
product
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SU691342468A
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English (en)
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Мартель Жак
Эймес Рене
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Руссель-Уклаф (Фирма)
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Priority claimed from FR6916944A external-priority patent/FR2043480A1/fr
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Publication of SU483830A3 publication Critical patent/SU483830A3/ru

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
    • H01H9/00—Details of switching devices, not covered by groups H01H1/00 - H01H7/00
    • H01H9/18—Distinguishing marks on switches, e.g. for indicating switch location in the dark; Adaptation of switches to receive distinguishing marks
    • A—HUMAN NECESSITIES
    • A41—WEARING APPAREL
    • A41H—APPLIANCES OR METHODS FOR MAKING CLOTHES, e.g. FOR DRESS-MAKING OR FOR TAILORING, NOT OTHERWISE PROVIDED FOR
    • A41H43/00—Other methods, machines or appliances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D207/36—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/02—Preparation
    • C07D501/08—Preparation by forming the ring or condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C07D501/42—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by an araliphatic carboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F21—LIGHTING
    • F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
    • F21V17/00—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages
    • F21V17/10—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages characterised by specific fastening means or way of fastening
    • F21V17/16—Fastening of component parts of lighting devices, e.g. shades, globes, refractors, reflectors, filters, screens, grids or protective cages characterised by specific fastening means or way of fastening by deformation of parts; Snap action mounting
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
    • H01H13/00—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch
    • H01H13/50—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch having a single operating member
    • H01H13/52—Switches having rectilinearly-movable operating part or parts adapted for pushing or pulling in one direction only, e.g. push-button switch having a single operating member the contact returning to its original state immediately upon removal of operating force, e.g. bell-push switch

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Theoretical Computer Science (AREA)
  • Epidemiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Biotechnology (AREA)
  • Textile Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Description

(54) СПОСОБ ПОЛУЧЕНИЯ 7-АЦИЛАМИНОЦЕФАЛОСПОРИНОВ
под разрежением, промывают водой, сушат и очищают продукт растворением в 1 мл диметилсульфоксида . Прибавив к фильтрату 1 мл метанола и затем 1 мл воды, фильтруют под разрежением, промывают осадок водным метанолом и эфиром и получают 120 мг (70%) продукта, т. пл. 260°С, в виде бесцветных кристаллов, растворимых в диметилформамиде и диметилсульфоксиде, а также в водных щелочах, но малорастворимых в обычных органических растворител х.
Вычислено, %: С 54,68; Н 4,05; N11,26; S 8,58.
CirHisOsNsS {мол. вес 373,37).
Найдено, %: С 54,9; Н 4,02; N 11,0; S 8,7.
В ИК-спектре, сн том в вазелиновом масле, обнаружены полосы поглощени , см-: 1767 (р-лактам); 1678, 1704, 1658 (7-лактам + + амид + кислота); 1532 (второй амид), и поглощение в области объединенных OH/NH- и ОН-групп ароматической кислоты.
Пример 2. Получение Y-лактама DL-6H,
7Н-цис-7- п - сульфонилфенилацетамидо-3-аминонометилцефалоспораповой-4 кислоты.
К суспензии 106 мг -лактама Z)L-6H, 7Нцис-амино - 3 - аминометилцефалоспорановой-4 кислоты в 1 мл диметилформамида прибавл ют 277 мг натриевой соли д-сульфонилфенилуксусной кислоты и 115 мг дициклогексилкарбодиимида . Реакционную смесь перемещивают 2 час при комнатной температуре, отдел ют при разрежении дициклогексилмочевину, прибавл ют 3 мл диоксана и отфильтровывают под разрежением образовавшийс  продукт, который перекристаллизовывают из смеси воды с диоксаном.
Получают 162 г (70%) продукта, сольватированного с двум  молекулами диоксана, который тер ет 18,6% своего веса при 100°С в вакууме.
Дапные микроанализа вычислены дл  молекулы , сольватированной с 1/2 молекулы диоксана .
Вычислено, %: С 45,44; Н 3,82; N 8,84; S 13,48.
CisHisOTNgSsNa (мол. вес 475,46).
Найдено, %: С 45,1; Н 4,0; N 8,8; S 13,2.
ИК-спектр в вазелиновом масле, 781 (р-лактам), 1698 и 1655 (С 0 амида) 1560 (второй амид) и поглощение в области объединенных OH/NH.
Пример 3. Получение -лактама DL-6H, 7Н - цис -7-/г-аминофенилацетамидо-3-аминометилцефалоспорановой-4 кислоты.
К 755 мг п-аминофенилуксусной кислоты в 13,5 мл 1 Н. водного раствора диэтиламина прибавл ют 2,25 г хлористого тритила и перемешивают 0,5 час. После декантации прибавл ют 10 мл этилацетата и 5 мл 1 н. сол ной кислоты и экстрагируют эфиром. Экстракты выпаривают досуха в вакууме, остаток сушат и раствор ют в этиладетате. Прибавл ют диэтиламин и затиранием начинают кристаллизацию . Добавив эфир, фильтруют под разрежением , выливают остаток в смесь воды с эфиром , прибавл ют уксусную кислоту до растворени  продукта, промывают водой, сушат, фильтруют и упаривают фильтрат досуха в вакууме . Продукт кристаллизуют в петролейном эфире и получают 1,15 г (60%) «-тритиламинофенилуксусной кислоты.
В атмосфере азота к 786 мг п-тритиламинофенилуксусной кислоты в 8 мл безводного метиленхлорида прибавл ют 250 мг карбодиимида и перемешивают в 1 час при охлаждении до 10°С. Отфильтровывают под разрежением мочевину , упаривают фильтрат досуха и раствор ют остаток, образованный из ангидрида
/г-тритиламинофенилуксусной кислоты, в 4 мл диметилформамида.
К полученному раствору прибавл ют 106 мг 7-лактама Z)L-6H, 7Н-г{ис-7-амино-3-аминометилцефалоспорановой-4 кислоты и перемешивают при комнатной температуре в течение ночи . Затем прибавл ют метиленхлорид, промывают водой, экстрагируют промывные воды эфиром, объедин ют органические слои, сушат и концентрируют до маленького объема в вакууме без нагревани . Осаждают эфиром, фильтруют под разрежением, промывают эфиром и получают 233 мг у-лактама Z)L-6H, 7Нцис-7-п - тритиламинофенилацетамидо-3-аминометилцефалоспорановой-4 кислоты.
Насыщают 10 мл нитрометана хлористым водородом, обрабатывают льдом и добавл ют 1,045 г полученного тритилированного производного . Перемешивают 5 мин при комнатной температуре, отгон ют избыток сол ной кислоты , фильтруют под разрежением и получают 570 мг продукта, т. пл. 250°С. Дл  очистки 210 мг полученного продукта добавл ют в разбавленный водный раствор сол ной кислоты, нейтрализуют триэтиламином, фильтруют под
разрежением, промывают метанолом, а затем эфиром. Получают 150 мг у-лактама DL-6H, 7Н-цис-7-п - аминофенилацетамидо-3-аминометилцефалоспорановой-4 кислоты. Продукт плавитс  при температуре 250°С и имеет вид
кристаллов соломенно-желтого цвета.
Вычислено, %: С 55,8; Н 4,7; N 16,26; S 9,3. С1бН1бОзЫ45 (мол. вес 344,39). Найдено, %: С 55,5; Н 4,9; N 16,1; S 9,1. Пример 4. Получение у-лактама L(-{-)6Н , 7Н-г «с-7-(2-тиенилацетамидо)-3-аминометилцефалоспорановой-4 кислоты.
К суспензии 50 мг Лактама L(-|-)-6H, 7Н-цис-7- амино-3 - аминометилцефалоспорановой-4 кислоты в 4 мл лед ной воды прибавл ют 0,5 мл 10%-ного водного раствора бикарбоната натри , затем 5 капель тиенилацетилхлорида . Реакционную смесь перемешивают 5 мин при комнатной температуре, прибавл ют то же количество раствора бикарбоната
натри  и перемешивают еще 15 мин.
Фильтруют под разрежением, промывают водой, превращают в тестообразную массу с метанолом, а затем с эфиром. Получают 57 мг (75%) продукта, чистота которого подтверждаетс  тонкослойной хроматографией (R/ 0,62,
SU691342468A 1968-06-27 1969-06-25 Способ получени 7-ациламиноцефалоспоринов SU483830A3 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR156898 1968-06-27
FR6916944A FR2043480A1 (en) 1969-05-23 1969-05-23 Cephalosporin derivs

Publications (1)

Publication Number Publication Date
SU483830A3 true SU483830A3 (ru) 1975-09-05

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Application Number Title Priority Date Filing Date
SU691342468A SU483830A3 (ru) 1968-06-27 1969-06-25 Способ получени 7-ациламиноцефалоспоринов

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JP (1) JPS4840360B1 (ru)
AT (1) AT301019B (ru)
BE (1) BE735128A (ru)
CH (2) CH536322A (ru)
GB (1) GB1271014A (ru)
IL (1) IL32383A (ru)
NL (1) NL6909858A (ru)
PL (1) PL82615B1 (ru)
SU (1) SU483830A3 (ru)

Also Published As

Publication number Publication date
AT301019B (de) 1972-08-25
NL6909858A (ru) 1969-12-30
IL32383A (en) 1973-10-25
GB1271014A (en) 1972-04-19
DE1932505B2 (de) 1977-01-13
PL82615B1 (en) 1975-10-31
CH536322A (fr) 1973-04-30
IL32383A0 (en) 1969-08-27
CH513921A (fr) 1971-10-15
BE735128A (ru) 1969-12-29
JPS4840360B1 (ru) 1973-11-30
DE1932505A1 (de) 1970-01-15

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