SU614746A3 - Method of obtaining prostaglandine analogue - Google Patents

Method of obtaining prostaglandine analogue

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Publication number
SU614746A3
SU614746A3 SU762334454A SU2334454A SU614746A3 SU 614746 A3 SU614746 A3 SU 614746A3 SU 762334454 A SU762334454 A SU 762334454A SU 2334454 A SU2334454 A SU 2334454A SU 614746 A3 SU614746 A3 SU 614746A3
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formula
ethyl
acid
methyl
solution
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SU762334454A
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Russian (ru)
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Жан Ален
Пижероль Шарль
Эймар Пьер
Симиан Жак
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Лябаз С.А., (Фирма)
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    • 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
    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—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 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
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    • C07D207/26—2-Pyrrolidones
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
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    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
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Description

(54) СПОСОБ ПОЛУЧЕНИЯ АНАЛОГА ПЬХЮТАГЛЛИДИИА(54) METHOD OF OBTAINING ANALOGUE PHUHUTAGLLIDIA

II

Иэобрегенне относитс  к способу получени  не описанного в литературе аналога простаглаидина формулыIobregenne does not relate to a method for producing a prostaglaidin analogue of the formula not described in literature.

Предлагаемый способ получени  aiianoi-,i простагландина заключаетс  в rovf, что (;лс жный эфир обшей формулы 1The proposed method for the preparation of aiianoi-, i prostaglandin consists in rovf that (; ester of the general formula 1

СООНCun

соонsoon

10ten

онhe

обладающего фармакологической активностью.with pharmacological activity.

Известен способ получени  карбоновых кислот с помощью щелочного гидролиза сложных эфиров ij.A known method for producing carboxylic acids by alkaline hydrolysis of esters ij.

Использование известной реакции позвол ет получать новое производное простаглаи-20 диИа, про вл ющее фармакологическую активность.The use of a known reaction allows the preparation of a new prostaglai-20 diIa derivative exhibiting pharmacological activity.

иель изобретени  - расщиреиие ассортимеита биологически активных соедииеинй. 25The invention of the invention is the expansion of the assortite of biologically active compounds. 25

в которой и представл ет собой линейшлй или разветвленный алкнльиый радикпл, содержащий 1-7 атомов углерода, пооверглюг взаимодействию с гидроокисью щелочно1Х металла в спиртовой среде при комнатной температуре с последующей обработкой сил ной кислотой.in which it represents a linear or branched alkali radikpl containing 1-7 carbon atoms, interacting with an alkali metal hydroxide in an alcohol medium at room temperature followed by treatment with strong acid.

Соединени  формулы Т, в которой Tt п|х.лставл ет ообой метил нли этил, могут быть получены восстанхжлением 3)L - uu-карбометокси- или карбэтокси-1-гексип-5-(3-(Ж(:о-1-октен- Еj-Bin )-2-пирролидинона обшей формулы ДCompounds of formula T in which Tt p | x. Represents methyl methyl or ethyl can be obtained by reduction 3) L - u-carbomethoxy or carbethoxy-1-hexyp-5- (3- (W (: o-1- octene-Ej-Bin) -2-pyrrolidinone of the general formula D

ClOORCloor

R которой Т -метил или атнл, с помощью подход щего восстановител , например бо(гидрида натри , в инертной среде, например диметокснэтане, при , предпочтительно 0°С.R of which T is methyl or atnl, using a suitable reducing agent, for example bo (sodium hydride, in an inert medium, for example dimethoxynethane, with, preferably 0 ° C.

Соединени  могут быть получены из DI -пироглутаминовЫ кислоты ф( мулыCompounds can be obtained from DI-pyroglutamic acids f (mules

(J(J

7«Н7 "H

Соон Soon

этерификацией последней этанолом в присутствии кислоты, например п олуолсуль- фоювой, получают этил-пироглутамат формулыby esterification of the latter with ethanol in the presence of an acid, for example, p-olusulfonic, ethyl pyroglutamate of the formula

ОABOUT

NHNH

ид.id

который затем восстанавливают б гидрндом натри  в растворвтело,. например метаноле, получа  (жсиметил-2-пирропидинон формулыwhich is then reduced with sodium hydrnd in solution, in body ,. for example, methanol to obtain (zsimethyl-2-pyrropidinone of the formula

IоIo

тшtsh

i-Li-l

СНгОНSNGON

Затем это соединение подвергают взаимо Действию с 2,3-дигндрс«тираном в инертной среде, например хлористом метилене, в присутствии кислоты, например ,п- олуолсуль- фоновой, и получают DU -5-(гвтрагидр пиранил-2-сжсиметил )-2-пирролидинон формулыThis compound is then reacted with a 2,3-diggers "tyrant in an inert medium, for example, methylene chloride, in the presence of an acid, for example, p-oluolsulfonic), to give DU-5- (pyrayl-2-ssimethyl) -2 -pyrrolidinone formula

ОABOUT

IXIx

«„о""about

который обрабатывают метил- или 9тил-7-бромгептаноатом обшей which is treated with methyl or 9-7-bromoheptanoate sheath

)4Вг,) 4Vg,

где R имеет те же значени , что и в формуле JT , в инертном растворителе,, предпочтительно толуоле, в присутствии амида натри , и выдел ют соединени  общей формулы jjwhere R has the same meaning as in formula JT, in an inert solvent, preferably toluene, in the presence of sodium amide, and compounds of the general formula jj are isolated

СООЕ Sooe

СИ, о-/ЛSI, o- / l

Ов которой т имеет те же значени , что и в формуле Н .Oh which t has the same meaning as in the formula.

3)Ь-и;-Карбометокси- или карбэтокси-1-гексил-51 тетрагндропйранил-2-сжсиметил)- -2-пирролидинон формулы Ц гидропиауют в кислой среде, например в сс п ной кислоте , в присутствии растворител , например метанола, и получают I)L -ч -карбометокси- или карбэтокси-i-гексил-б-оксиметил- -2-пирролидинон обивй формуль 3) L-and; -Carbomethoxy- or carbethoxy-1-hexyl-51 tetrahydropyranyl-2-ssimethyl) -2-pyrrolidinone of the formula C is hydropiated in an acidic medium, for example, with sulfuric acid, in the presence of a solvent, for example methanol, and get I) L-h -carbomethoxy- or carbethoxy-i-hexyl-b-hydroxymethyl -2 -2-pyrrolidinone obiv formul

эоeo

С ООНFrom the UN

3535

СНгОнSNGon

в которой т имеет те же значени , что и в формуле Я , затем первичный спирт, окисл ют до альдегида в инертной среде, например бензоле, при комбинированном воздействии диметилсульфоксида, дициклогексилкарбодиимида и дихлоруксусной кисS лоты, получаю т Ли-Ш-карбометокси- или карбэтокси-1-гексил-5-«арбоксальдегид-2-пирролидинон формулыwherein t has the same meaning as in formula I, then primary alcohol, is oxidized to the aldehyde in an inert medium, for example benzene, when combined with dimethyl sulfoxide, dicyclohexylcarbodiimide and dichloroacetic acid, get t-Li-Sh-carbomethoxy or carbethoxy -1-hexyl-5- "arboxaldehyde-2-pyrrolidinone of the formula

COORCOOR

СноSno

5Л В которой т имеет те же значени , что и в формуле Д . Альдегидную группу в синтезированном соединении подвергают реакции Виттига с 1-трифени/|фосфоранилиден-2-геитаноном формулы IV5L In which m has the same meanings as in formula D. The aldehyde group in the synthesized compound is subjected to the Wittig reaction with 1-tripheny / phosphoranylidene-2-geitanone of formula IV

Claims (1)

(CfcH«),P CHCOC,H . с тем, чтобы получить соответственно DL-Ш -карбом«гокси- или карбэтоксн-1-гексил- -5-(3-oкco-l-oктeн- EJ-ил)-2-пирролидинон формулы И . Метил- или этил-7-бромгептаноат можно получить из пробковой кислоты (октаидиоеой кислоты), которую перевод т в ме тилсжый или этиловый моноэфир, затем обр батывают эфир нитратом серебра, получают метил- или этилсуберат серебра и о рабатывают соль бромом в инертной среде, например четыреххлористом углероде. Фосфорсодержащее соединение формулы W может быть получено из дипентилкадми  (получают из пентилмагнийбромида и хлористого кадми ) и монохлорацетилхлорида. Полученный 1-хлор-2-гептан он обрабатывают трифенилфосфином, образующийс  трифенил-2-оксогептилфосфорийхлорид формулы ( t6H5)3PCH2 ioC5HiiCr с помощью водного раствора поташа перево д т в соединение формулы IV . Другие сложные эфиры формулы I могут быть получены по методике, приведенной выше дл  приготовлени  метилгжых и этиловых эфир ОБ формулы I . Пример. ПолученнеЭи - UU- арбсжси-1-гексил-5 (З-окси-1-октек )-2-пирролидинона или DL -8-аза-11-деокси-ПГЕ . В круглодонную трехгорлую колбу емкс стью 250 мл, снабженную кеханической мешалкой, валивают 1ОО мл метанола и 2,6 г Dl,-u -кapбoмeтoкcи-l-гeкcил-5-lЗrOкcи-l-oктeн- E -ил )-2-пиppoлидинoнa. Образовавшийс  раствор охла аают на бане с лед нсй водой до О С, затем медленно пр ливают 40 мл 0,5 н. раствора едкого натра оставл ют на 2,5 ч при комнатной температуре , добавл ют 20 мл воды, полученный водный раствор промывают 25%-ным раство ром сол нсй кислоты до рН 2 и несколько раз экстрагируют этилацетатом. Органические фазы соедин ют, промывают насыщенным раствором хлористого натри , сушат и удал ют растворитель, Пол чают 2,1 г Ш5%) целевого соединени  в виде частично o.iкристаллизсдаавшегос  гигроскопичного ix-nii. Хроматографи  в тонком слое силика1х ли с применением смеси бензол-аиоксап-уксусна  кислота (90:25:4) дает основное п тно Т f 0,3 и два п тна с Я О,39 и 1 соотетственно . ИК-спектр 1хлороформ), см , 1710 1С-0), 1665 (CO-N). Формула изобретений 1. Способ получени  аналога простагланина формулы отличающийс  тем, что сложный эфир обшвй формулы В которой т представл ет линейный или разветвленный алкильный радикал, содержащий 1-7 атомов углерода, подвергают взаимодействию с гидроокисью щелочного металла в спиртовой среде при комнатной температуре с последующей обработкой сильней . кислотой, после чего целевой продукт выдел ют. Источники информйции, прин тые во внимание при жсспертизе: 1. Вайганд-Хельгетаг.Методы эксперимента в органической химии, М., Хими ;, с. 366, 1968.(CfcH "), P CHCOC, H. so as to obtain, respectively, the DL-III-carb "goxy- or carbethox-1-hexyl-5- (3-occo-1-octen-EJ-yl) -2-pyrrolidinone of the formula I. Methyl or ethyl 7-bromoheptanoate can be obtained from corky acid (octaic acid), which is converted into methyl or ethyl monoether, then treated with ether with silver nitrate, silver methyl or ethyl suber is obtained and the salt is worked up with bromine in an inert medium, for example carbon tetrachloride. The phosphorus-containing compound of the formula W can be obtained from diphenylcadmi (obtained from pentylmagnesium bromide and cadmium chloride) and monochloroacetyl chloride. The resulting 1-chloro-2-heptane is treated with triphenylphosphine, which forms triphenyl-2-oxoheptylphosphoric chloride of the formula (t6H5) 3PCH2 ioC5HiiCr using an aqueous solution of potash to a compound of formula IV. Other esters of formula I can be prepared according to the procedure outlined above for the preparation of methyl ether and ethyl ester ABOUT formula I. Example. The resulting EE is UU-arbs-1-hexyl-5 (3-hydroxy-1-octec) -2-pyrrolidinone or DL-8-aza-11-deoxy-PGE. In a round-bottom three-neck flask with a capacity of 250 ml, equipped with a mechanical stirrer, 1OO ml of methanol and 2.6 g of Dl, -i-carbox-1-hexyl-5-3-oxy-1-pyropolydone are poured. The resulting solution is cooled in an ice-water bath to 0 ° C, then 40 ml 0.5N is slowly poured. sodium hydroxide solution is left for 2.5 hours at room temperature, 20 ml of water are added, the resulting aqueous solution is washed with a 25% solution of hydrochloric acid to pH 2 and extracted several times with ethyl acetate. The organic phases are combined, washed with a saturated solution of sodium chloride, dried and the solvent is removed. Obtain 2.1 g of the 5 5%) target compound as a partially o. Crystallization of the hygroscopic ix-nii given. Chromatography in a thin layer of silica gel using a mixture of benzene-aioxap-acetic acid (90: 25: 4) gives the main spot T f 0.3 and two spots with I O, 39 and 1 respectively. IR spectrum of 1 chloroform), cm, 1710 1C-0), 1665 (CO-N). Claims 1. A method for producing a prostaglanin analogue of a formula in which the general ester of formula B contains a linear or branched alkyl radical containing 1-7 carbon atoms and is reacted with an alkali metal hydroxide in an alcoholic medium at room temperature followed by treatment. is stronger. acid, after which the desired product is isolated. Sources of information taken into account when testing: 1. Vaigand-Helgetag. Experimental methods in organic chemistry, M., Himi;, p. 366, 1968.
SU762334454A 1975-03-21 1976-03-19 Method of obtaining prostaglandine analogue SU614746A3 (en)

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GB12034/75A GB1529852A (en) 1975-03-21 1975-03-21 8-azaprostaglandins and process for the preparation thereof

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SU614746A3 true SU614746A3 (en) 1978-07-05

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US4097489A (en) * 1977-06-17 1978-06-27 The Upjohn Company 9-Deoxy-9α,6-nitrilo or 6,9α-imino-PGF compounds
US5540618A (en) * 1994-10-28 1996-07-30 National University Of Singapore Passive attenuator for shelter protection against explosions
WO2003074483A1 (en) 2002-03-05 2003-09-12 Ono Pharmaceutical Co., Ltd. 8-azaprostaglandin derivative compounds and drugs containing the compounds as the active ingredient

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FR2304340A1 (en) 1976-10-15
FI760744A (en) 1976-09-22
GB1529852A (en) 1978-10-25
FI61692C (en) 1982-09-10
JPS51138671A (en) 1976-11-30
DE2612114A1 (en) 1976-10-07
ES446239A1 (en) 1977-07-01
DK140937C (en) 1980-05-19
FR2304340B1 (en) 1979-06-29
ATA195676A (en) 1978-06-15
DK88276A (en) 1976-09-22
PT64919A (en) 1976-04-01
CH611604A5 (en) 1979-06-15
OA05279A (en) 1981-02-28
HU173348B (en) 1979-04-28
ES458389A1 (en) 1978-02-16
IE42966B1 (en) 1980-11-19
BE839761A (en) 1976-09-20
CA1076587A (en) 1980-04-29
AU1189976A (en) 1977-09-15
IT1061011B (en) 1982-10-20
YU73876A (en) 1982-10-31
NO144147C (en) 1981-07-15
PT64919B (en) 1977-08-24
JPS607602B2 (en) 1985-02-26
NZ180251A (en) 1978-07-28
NO760994L (en) 1976-09-22
MX3301E (en) 1980-09-03
IE42966L (en) 1976-09-21
AU501105B2 (en) 1979-06-14
CH611881A5 (en) 1979-06-29
NL7602891A (en) 1976-09-23
AR213172A1 (en) 1978-12-29
SE7603400L (en) 1976-09-22
AT348163B (en) 1979-02-12
NO144147B (en) 1981-03-23
ZA761448B (en) 1977-03-30
FI61692B (en) 1982-05-31
DK140937B (en) 1979-12-10
SE418290B (en) 1981-05-18

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