SU884569A3 - Method of preparing 20-methyl-13,14-didehydro-rg12-derivatives - Google Patents

Method of preparing 20-methyl-13,14-didehydro-rg12-derivatives Download PDF

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Publication number
SU884569A3
SU884569A3 SU792790905A SU2790905A SU884569A3 SU 884569 A3 SU884569 A3 SU 884569A3 SU 792790905 A SU792790905 A SU 792790905A SU 2790905 A SU2790905 A SU 2790905A SU 884569 A3 SU884569 A3 SU 884569A3
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SU
USSR - Soviet Union
Prior art keywords
methyl
derivatives
didehydro
hydrogen
pgl2
Prior art date
Application number
SU792790905A
Other languages
Russian (ru)
Inventor
Гандольфи Кармело
Андреони Алессандро
Сецерани Роберто
Original Assignee
Фирма Фармиталиа Карло Эрба С.П.А.(Фирма)
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Application filed by Фирма Фармиталиа Карло Эрба С.П.А.(Фирма) filed Critical Фирма Фармиталиа Карло Эрба С.П.А.(Фирма)
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Publication of SU884569A3 publication Critical patent/SU884569A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Furan Compounds (AREA)

Abstract

20-Methyl-13, 14-didehydro- PGl2 derivatives of formula: <IMAGE> where R is hydrogen or methyl and M is hydrogen or a pharmaceutically acceptable cation have a greater effect than PGl2 or 20-methyl-PGl2 in disaggregating platelets in the bloodstream and in vasodilating action. They can be prepared by dehydrohalogenation of dihalo compounds of formula (II> <IMAGE> where R and M have the meanings given above and X1 and X2 are independently bromine, chlorine or iodine. A sodium or potassium alkoxide is the preferred dehydrohalogenating agent.

Description

(5) СПОСОБ ПОЛУЧЕНИЯ 20-МЕТИЛ-13,U-ДИДЕГИДРО-РСIn-ПРОИЗВОДНЫХ(5) METHOD OF OBTAINING 20-METHIL-13, U-DIDEHYDRO-PCIn-DERIVATIVES

Изобретение относитс  в способу получени  не описанных в литературеThe invention relates to a method for obtaining not described in the literature.

20-метил-13,14-дидегидро-РС12-производных общей формулы20-methyl-13,14-didehydro-PC12 derivatives of the general formula

HClCH), СООМHClCH), SOOM

CHtCHt

о (about (

ЯаYa

II

- C C-CWCHCjHrt- C C-CWCHCjHrt

но|нbut | n

где R - водород или метил;where R is hydrogen or methyl;

М - Н или фармацевтически пригодный катион,M - N or pharmaceutically suitable cation,

обладающих фармакологической активностью .possessing pharmacological activity.

Известен способ получени  непредельных соединений, заключающийс  в дегидрогалоидировании органических галогенидов Г1 .A known method for the preparation of unsaturated compounds consists in the dehydrohalogenation of organic halides G1.

Цель изобретени  - использование известного способа дл  получени  ноИЛИ ИХ СОЛЕЙThe purpose of the invention is the use of a known method to obtain their OR SALTS

вых фармакологических активных простагландинов общей формулы 1.Pharmacologically active prostaglandins of general formula 1.

Эта цель достигаетс  тем, что согласно способу получвуи 20-метил5 -13,1 -дидегидро-РС1о производных общей формулы 1 соединение общей формулыThis goal is achieved in that, according to the method of preparing 20-methyl 5-13.1 dehydro-PC1 o derivatives of the general formula 1, a compound of the general formula

X, pHfCMJjCOOMX, pHfCMJjCOOM

снsn

toto

с with

(ff)(ff)

/П I/ P I

V-ULc«/V-ULc "/

С 1-СЩИнS 1-SCHCHIN

1515

оиoi

онhe

где R и М имеют вышеуказанные значени  , К и Хг независимо друг от другаwhere R and M have the above values, K and Xg independently of each other

- хлор,бром или йод, подвергают дегидрогалоидированию с последующим - chlorine, bromine or iodine is dehydrohalogenated, followed by

20 выделением целевого продукта в свобод ном виде или в виде солей.20 by isolating the desired product in free form or in the form of salts.

Как правило, в качестве дегидрогалоидирующуго агента используют соль диметилсульфинилкарбаниона с щелочнымAs a rule, as a dehydrohalogenating agent, dimethylsulfinylcarbanion salt with alkali is used.

2525

Claims (1)

Формула изобретенияClaim Способ получения 20-метил-13,14-дидегидро-РС1^-производных общей ФЬрмулы где R М ыусн^соон II с--.A method of obtaining 20-methyl-13,14-didehydro-PC1 ^ derivatives of the general formula where R M ssn ^ ion II s--. /? I C=C-CHCHCsHrt _ он ’/? IC = C-CHCHC s H rt _ he ' - водород или метил,- hydrogen or methyl, - водород или фармацевтически пригодный катион ичающийся о т л соединение общей формулы- hydrogen or a pharmaceutically suitable cation free compound of general formula Х< СН(СН2),С00М или их солей, тем, чтоX <CH (CH 2 ), C00M or their salts, so that R и М имеют вышеуказанные значегде ния , X 4 и X независимо друг от друга хлор, бром или иод, подвергают дегидрогалоидированию с последующим выделением продукта в свободном·виде или в виде солей.R and M have the above values, X 4 and X are independently chloro, bromo or iodo, are subjected to dehydrohalogenation, followed by isolation of the product in its free form or in the form of salts.
SU792790905A 1978-07-20 1979-07-19 Method of preparing 20-methyl-13,14-didehydro-rg12-derivatives SU884569A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT25903/78A IT1099575B (en) 1978-07-20 1978-07-20 20-METHYL-13,14-DEHYDRO-PGI2 'ITS SALTS AND ITS 16S- AND 16R-METHYL DERIVATIVES

Publications (1)

Publication Number Publication Date
SU884569A3 true SU884569A3 (en) 1981-11-23

Family

ID=11218084

Family Applications (1)

Application Number Title Priority Date Filing Date
SU792790905A SU884569A3 (en) 1978-07-20 1979-07-19 Method of preparing 20-methyl-13,14-didehydro-rg12-derivatives

Country Status (21)

Country Link
JP (1) JPS5517389A (en)
AT (1) AT367758B (en)
AU (1) AU520750B2 (en)
BE (1) BE877687A (en)
CA (1) CA1183531A (en)
CH (1) CH640522A5 (en)
CS (1) CS208668B2 (en)
DE (1) DE2922110A1 (en)
DK (1) DK304479A (en)
FR (1) FR2431492A1 (en)
GB (1) GB2025972B (en)
HU (1) HU182727B (en)
IE (1) IE48593B1 (en)
IL (1) IL57552A (en)
IT (1) IT1099575B (en)
NL (1) NL7905259A (en)
NO (1) NO792313L (en)
SE (1) SE446002B (en)
SU (1) SU884569A3 (en)
YU (1) YU152979A (en)
ZA (1) ZA793123B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3029984C2 (en) * 1980-08-08 1983-12-15 Grünenthal GmbH, 5190 Stolberg 2-Oxabicyclo [3.3.0] octane derivatives and medicinal products containing them

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL51189A (en) * 1976-02-04 1985-08-30 Upjohn Co Prostaglandin analogs
AU3583378A (en) * 1977-06-06 1979-11-08 Chicago The University Of Prostacyclin analogs

Also Published As

Publication number Publication date
AU520750B2 (en) 1982-02-25
GB2025972A (en) 1980-01-30
FR2431492A1 (en) 1980-02-15
IL57552A (en) 1983-02-23
FR2431492B1 (en) 1982-07-16
IE791360L (en) 1980-01-20
JPS5517389A (en) 1980-02-06
ATA435479A (en) 1981-12-15
BE877687A (en) 1980-01-14
DE2922110A1 (en) 1980-01-31
NO792313L (en) 1980-01-22
CA1183531A (en) 1985-03-05
AU4803479A (en) 1980-01-24
YU152979A (en) 1983-01-21
SE446002B (en) 1986-08-04
IT7825903A0 (en) 1978-07-20
CH640522A5 (en) 1984-01-13
HU182727B (en) 1984-03-28
CS208668B2 (en) 1981-09-15
DK304479A (en) 1980-01-21
IE48593B1 (en) 1985-03-20
AT367758B (en) 1982-07-26
NL7905259A (en) 1980-01-22
IT1099575B (en) 1985-09-18
ZA793123B (en) 1980-06-25
IL57552A0 (en) 1979-10-31
SE7906234L (en) 1980-01-21
GB2025972B (en) 1982-09-15

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