SU1470198A3 - Способ получени производных стероидов - Google Patents

Способ получени производных стероидов Download PDF

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SU1470198A3
SU1470198A3 SU3952445A SU3952445A SU1470198A3 SU 1470198 A3 SU1470198 A3 SU 1470198A3 SU 3952445 A SU3952445 A SU 3952445A SU 3952445 A SU3952445 A SU 3952445A SU 1470198 A3 SU1470198 A3 SU 1470198A3
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general formula
compounds
chi
alkyl
alk
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SU3952445A
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Торелли Весперто
Неделек Люсьен
Могилевский Мартин
Мура Анн-Мари
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Руссель-Юклаф (Фирма)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
    • C07J1/0044—Alkenyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/001—Lactones
    • C07J21/003—Lactones at position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005—Ketals
    • C07J21/006—Ketals at position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J33/005—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/006—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
    • C07J53/002—Carbocyclic rings fused
    • C07J53/004—3 membered carbocyclic rings
    • C07J53/007—3 membered carbocyclic rings in position 6-7

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Separation By Low-Temperature Treatments (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Abstract

Изобретение касаетс  стероидов, в частности способа получени  производных стероидов общей формулы с(х) (.. .Y) -г.н,-сн, -cH4:(RO-CHi:-CH C-CH-CH.-CH,-r.H-...-C(CbCRA)-CH7- -CHi-C(0)-CH, где Ri С,-Сэ-а/ алкил (он может быть замещен гидроксигруп- пой); К, - X и Y означают ради- - кал - О - С (0) ..., обладающих фармакологическими свойствами, что может быть использовано в медицине. Цель - создание новых фармацевтических активных соединений указанного класса. Синтез целевых веществ ведут реакцией соединени  общей формулы С(О)-СЕ7-СНг-GH-C(RО-СНг-СН... С ч:н-сн7-сн,-с(... .oH)-c(CECRi Ь . -cTtg-CH 7-CK-CHi, где R, и R указаны вьЕше, а имеющиес  оксигруппы защищены , К - кетальна  защитна  группа дл  кетонной функции, с реагентом общей формулы CH CH-CH -0-P(0)(Alk)5,, где Alk Ci-Сз-алкил, в присутствии сильного органического основани  с последующей обработкой кислотой. Новые соединени  обладают гипотензивной активностью, так как измен ют мембранную проницаемость сосудистых стенок к Na и К®, что способствует снижению их сократимости. Токсичность соединений ЛД jo 400 мг/кг. 1 табл. (У) 4:

Description

где R-, - С1-С j-ал кил, возможно замещенный гидроксигруп- пой;
.где А1К - С,-С -алкш1, в присутствии сильного органического основани  с последующей обработкой кислотой.
Продукты
Продукт по примеру 1
Продукт по примеру 5
Продукт X (10/i- -этинил-21-гидр- окси-19-нор-пре- гна-4,9(11)-дие- на-3,20-дион)
Эффлюкс in vitro Na при концентрации 10 М, % торможени . Антагонистический эффект
пассивный
100 28
100 60

Claims (1)

  1. Формула изобретения
    Способ получения производных стероидов общей формулы где R, - С,-Салкил, возможно замещенный гидроксигруппой;
    где R, и R2 имеют указанные значения, 20 а имеющиеся оксигруппы защищены;
    К - кетальная защитная группа для кетонной j функции, >.
    /обрабатывают реагентом общей формулы (ΑΙΚ)ζΝχθ . . /Р-°-СН2-СН-СН ? , зо(А1К)2К/ 2 .где А1К - С,-С3-алкил, в присутствии сильного органического основания с последующей обработкой кислотой.
    Продукты
    Эффлюкс in vitro 1lNa при концентрации 10‘8М, % торможения. Антагонистический эффект
    пассивный j насос Продукт по приме- РУ 1 Продукт по приме- 100 1.00 РУ 5 28 60 Продукт X (10^-этинил-21-гидрокси-1 9-нор-прегна-4,9(11)-дие- на-3,20-дион) 0 0
SU3952445A 1984-08-24 1985-08-23 Способ получени производных стероидов SU1470198A3 (ru)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8413189A FR2569408B1 (fr) 1984-08-24 1984-08-24 Nouveaux steroides substitues en position 10 par un radical comportant une double ou triple liaison, leur procede de preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant

Publications (1)

Publication Number Publication Date
SU1470198A3 true SU1470198A3 (ru) 1989-03-30

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ID=9307209

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SU3952445A SU1470198A3 (ru) 1984-08-24 1985-08-23 Способ получени производных стероидов

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Country Link
US (1) US4701449A (ru)
EP (2) EP0313960B1 (ru)
JP (1) JPH0649717B2 (ru)
KR (1) KR940008596B1 (ru)
CN (1) CN1029683C (ru)
AT (2) ATE78826T1 (ru)
AU (1) AU580086B2 (ru)
CA (1) CA1260459A (ru)
DE (2) DE3586427T2 (ru)
DK (1) DK168538B1 (ru)
ES (1) ES8604988A1 (ru)
FI (1) FI82699C (ru)
FR (1) FR2569408B1 (ru)
GR (1) GR852037B (ru)
HU (1) HU194276B (ru)
IE (1) IE64675B1 (ru)
IL (1) IL76096A (ru)
MX (1) MX159930A (ru)
PT (1) PT81020B (ru)
SU (1) SU1470198A3 (ru)
ZA (1) ZA856427B (ru)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2576025B1 (fr) * 1985-01-14 1987-01-23 Roussel Uclaf Nouveaux steroides substitues en position 10, leur procede et les intermediaires de preparation, leur application comme medicaments, les compositions pharmaceutiques les contenant
FR2594829B1 (fr) * 1986-02-24 1988-06-03 Roussel Uclaf Nouveaux steroides 9 (11) satures substitues en position 10 par un radical comportant une triple liaison, leur procede de preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant
WO1990002781A1 (en) * 1988-09-16 1990-03-22 Lithium Corporation Of America Thermally stable, reactive organometallic compositions containing copper
US5100575A (en) * 1989-09-08 1992-03-31 Fmc Corporation Thermally stable, reactive organometallic compositions containing copper
ATE473759T1 (de) 1998-05-22 2010-07-15 Univ Leland Stanford Junior Bifunktionelle moleküle sowie darauf basierende therapien.
EP2392258B1 (en) 2005-04-28 2014-10-08 Proteus Digital Health, Inc. Pharma-informatics system
US9062126B2 (en) 2005-09-16 2015-06-23 Raptor Pharmaceuticals Inc. Compositions comprising receptor-associated protein (RAP) variants specific for CR-containing proteins and uses thereof
FR2917975B1 (fr) * 2007-06-26 2009-10-16 Ceva Sante Animale Sa Compositions et traitement de l'insuffisance cardiaque chez les animaux mammiferes non humains
US20090270356A1 (en) * 2008-04-28 2009-10-29 Ceva Sante Animale Sa Compositions and treatments of heart failure in non-human mammal animals
AU2010216512B2 (en) 2009-02-20 2016-06-30 2-Bbb Medicines B.V. Glutathione-based drug delivery system
WO2010129819A2 (en) 2009-05-06 2010-11-11 Laboratory Skin Care, Inc. Dermal delivery compositions comprising active agent-calcium phosphate particle complexes and methods of using the same
CN103145785B (zh) * 2013-03-19 2016-03-02 浙江仙居仙乐药业有限公司 一种醋酸环丙孕酮脱氢物的合成方法

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US3102127A (en) * 1962-06-12 1963-08-27 Syntex Corp 19-methylene-androstane derivatives
US3218316A (en) * 1963-08-26 1965-11-16 Syntex Corp 10beta-ethynyl-19-norandrostane derivatives
US3275622A (en) * 1963-12-18 1966-09-27 Syntex Corp 19-alkylidene-delta4-3, 20-keto pregnanes
FR1519387A (fr) * 1966-04-20 1968-03-29 Hoffmann La Roche Procédé pour la préparation de 19-alcényl-stéroïdes
FR2344286A1 (fr) * 1976-03-16 1977-10-14 Roussel Uclaf Nouveaux derives 17-spirosultines, les g-hydroxy acides correspondants, leur procede de preparation et leur application comme medicament
FR2462445A1 (fr) * 1979-07-31 1981-02-13 Roussel Uclaf Nouveaux derives 17-/(hydroxymethyl) (formamido) methylene/steroides, leur procede de preparation et leur application a l'introduction de la chaine laterale hydroxyacetyle
HU179980B (en) * 1979-12-28 1983-01-28 Gyogyszerkutato Intezet Process for preparing substituted steroid-spiro-oxazolidinone derivatives
US4322416A (en) * 1980-06-27 1982-03-30 Merrell Dow Pharmaceuticals Inc. 10-Alkynyl steroids

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Title
Sturtz and laonang. Synthesis, 1980, с. 289. За вка ЕР №. 0023856, кл. G 06 F 11/12, 1981. *

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KR940008596B1 (ko) 1994-09-24
PT81020A (fr) 1985-09-01
ATE78826T1 (de) 1992-08-15
DK382185A (da) 1986-02-25
AU4662585A (en) 1986-02-27
CN85106995A (zh) 1987-04-01
US4701449A (en) 1987-10-20
FI82699B (fi) 1990-12-31
FI82699C (fi) 1991-04-10
DE3586427D1 (de) 1992-09-03
FI853254A0 (fi) 1985-08-23
EP0313960A1 (fr) 1989-05-03
EP0176399A1 (fr) 1986-04-02
ES546372A0 (es) 1986-03-01
PT81020B (pt) 1987-12-30
FI853254L (fi) 1986-02-25
DK382185D0 (da) 1985-08-23
MX159930A (es) 1989-10-06
CA1260459A (fr) 1989-09-26
GR852037B (ru) 1985-12-18
JPH0649717B2 (ja) 1994-06-29
CN1029683C (zh) 1995-09-06
DE3569739D1 (en) 1989-06-01
IL76096A (en) 1989-09-10
FR2569408A1 (fr) 1986-02-28
ATE42561T1 (de) 1989-05-15
FR2569408B1 (fr) 1986-10-03
EP0176399B1 (fr) 1989-04-26
HU194276B (en) 1988-01-28
HUT39461A (en) 1986-09-29
DE3586427T2 (de) 1993-01-07
DK168538B1 (da) 1994-04-18
IL76096A0 (en) 1985-12-31
IE852075L (en) 1986-02-24
AU580086B2 (en) 1988-12-22
KR860001824A (ko) 1986-03-22
ZA856427B (en) 1986-10-29
IE64675B1 (en) 1995-08-23
JPS6176499A (ja) 1986-04-18
ES8604988A1 (es) 1986-03-01
EP0313960B1 (fr) 1992-07-29

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