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WO1986000311A1 - Derives de steroides de series d'androstane - Google Patents

Derives de steroides de series d'androstane Download PDF

Info

Publication number
WO1986000311A1
WO1986000311A1 PCT/SU1984/000033 SU8400033W WO8600311A1 WO 1986000311 A1 WO1986000311 A1 WO 1986000311A1 SU 8400033 W SU8400033 W SU 8400033W WO 8600311 A1 WO8600311 A1 WO 8600311A1
Authority
WO
WIPO (PCT)
Prior art keywords
chloroethyl
androstan
series
aminophenyl
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/SU1984/000033
Other languages
English (en)
Russian (ru)
Inventor
Zoya Petrovna Sofiina
Leonid Fedorovich Larionov
Nina Dmitrievna Lagova
Galina Nikolaevna Platonova
Irina Mikhailovna Valueva
Kira Nikolaevna Kurdjumova
Elizaveta Nikolaevna Shkodinskaya
Ljudmila Pavlovna Sushinina
Lev Natanovich Volovelsky
Irina Mikhailovna Kuznetsova
Vladislav Grigorievich Degtyar
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
KHARKOVSKY NAUCHNO-ISSLEDOVATELSKY INSTITUT ENDOKR
VSESOJUZNY ONKOLOGICHESKY NAUCHNY TSENTR AKADEMII
Original Assignee
KHARKOVSKY NAUCHNO-ISSLEDOVATELSKY INSTITUT ENDOKR
VSESOJUZNY ONKOLOGICHESKY NAUCHNY TSENTR AKADEMII
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by KHARKOVSKY NAUCHNO-ISSLEDOVATELSKY INSTITUT ENDOKR, VSESOJUZNY ONKOLOGICHESKY NAUCHNY TSENTR AKADEMII filed Critical KHARKOVSKY NAUCHNO-ISSLEDOVATELSKY INSTITUT ENDOKR
Priority to DE19843490728 priority Critical patent/DE3490728T1/de
Priority to DE19843490728 priority patent/DE3490728C2/de
Priority to GB08602936A priority patent/GB2169900B/en
Priority to PCT/SU1984/000033 priority patent/WO1986000311A1/fr
Priority to CH571/86A priority patent/CH666276A5/de
Priority to JP60500685A priority patent/JPS61502256A/ja
Publication of WO1986000311A1 publication Critical patent/WO1986000311A1/fr
Priority to SE8600828A priority patent/SE457535B/sv
Priority to FI860815A priority patent/FI84834C/fi
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • null derivatives are, for example, the complex esters of ⁇ -di (2-cholesterol)
  • chlorofenacyl 5 doses of chlorofenacyl are 1-1.5 mg / kg in mice after 5 days of administration, but in case of direct dehydrogenated (long-lasting). kusa introduction. One of the connections is well-behaved.
  • n 3 -sn 3 ; - ⁇ .
  • the offered facilities in the western and western part are, as a part of the hospital, equipped with a test facility.
  • their synthetic analogs and 10 are the complex erases of the 5-unit, replaced by 2,3 and 17 positions ..
  • the claimed compounds are amorphous or small-sized, simple substances of white or white with a yellow color, not inactive
  • connections 15 waterborne, consumable in the urban environment.
  • the connections are long-term stable when stored in the dark at temperatures of +5 to 0 ° C, in which case the light turns yellow.
  • 20 of the invention are: ⁇ 7 ⁇ - [ ⁇ -di (2-chloroethyl) aminophenylate] -5 ⁇ - ⁇ -androstan- ⁇ 7 ⁇ ⁇ -o- ⁇ - classroom ( ⁇ ); 17 ⁇ > - [a - -di (2-chloroethyl) aminophenylbutyric] -5 ° C.
  • DIEDI compounds were lively in oil in doses, calculated in mg per kg body weight, for 5-10 days, excluded from the study on the body-
  • ESTRACITE ⁇ D ⁇ LI is in the same way a method of 0.9 discharging ⁇ réelle ⁇ réelle ⁇ .
  • Sa-755 S. : -256: Sa-755: b- ⁇ 2 ⁇ 0: -, y -256
  • the “+” sign means the stimulation of relaxation.
  • therapeutic doses of the claimed compounds lie in the range from 5 to 150 mg / kg
  • connection I has little effect on the environment of the United States, while the connection and the connection to it cause a deep shock
  • mice and ⁇ ys 25 ⁇ e ⁇ ed izves ⁇ nym and ⁇ gen ⁇ m ⁇ es ⁇ s ⁇ e ⁇ n- ⁇ i ⁇ na ⁇ m in ⁇ and ⁇ ⁇ iv ⁇ u ⁇ lev ⁇ y a ⁇ ivn ⁇ s ⁇ i in ⁇ n ⁇ shenii induced tsi ⁇ vanny ⁇ and s ⁇ n ⁇ anny ⁇ ⁇ u ⁇ ley yaichni ⁇ v and m ⁇ l ⁇ ch- n ⁇ y glands of mice and ⁇ ys.
  • Table 2 The potent activity of industrial arrays of a series of pulses from the target arising from the target.
  • Table 3 The beneficial effects of industrial facilities for industrial and industrial vehicles, which are from targets.
  • Table 5 provides data on the android and anabolic activity of the claimed compounds. From table 5 it is visible that
  • 35 gene activity is also the largest for compounds I and S.
  • the same androgenic activity of compound I is significantly weaker than for testosterone (known) - 16 - androgen).
  • Compound I is associated with cytosolic plasmas of dihydrates with subsequent interactions with the relevant medicaments
  • Shsle ⁇ e ⁇ a ⁇ ev ⁇ iches- ⁇ g ⁇ ⁇ u ⁇ sa s ⁇ edineyayaya I have ⁇ ys ⁇ e ⁇ aschae ⁇ sya ⁇ a ⁇ a ⁇ - ⁇ e ⁇ yaaya for yaya ⁇ ⁇ s ⁇ yannaya ⁇ ech ⁇ a.
  • the compound I possesses also alkilizing properties. ⁇ n ⁇ na ⁇ ushae ⁇ ⁇ tsess ⁇ ans ⁇ - ⁇ i ⁇ tsii and ⁇ ans ⁇ a ⁇ , vyzyvae ⁇ de ⁇ e ⁇ y s ⁇ u ⁇ u ⁇ y D ⁇ , ⁇ ye, ⁇ dna ⁇ , bys ⁇ ee v ⁇ ss ⁇ anavlivayu ⁇ sya in n ⁇ malny ⁇ ⁇ le ⁇ a ⁇ (selezen ⁇ a) than ⁇ _ ⁇ ⁇ _zh_sh ⁇ 3-37 5 (sa ⁇ me 37). Last witnesses to the election of good deafness.
  • connection I In general, on the basis of the connection I, it is indicated that the large-sized and non-hazardous androids have a lot of mobility.
  • the resulting mixture is stirred at a temperature of 80 ° C for 24 hours and is separated by hydrochloric acid.
  • Bezolyayuyu of a rinsing place is washed by water in the ⁇ réelle, ⁇ ⁇ ⁇ and vaporizing. It can be disassembled in benzene; it will be removed from 0, eluting with amber. The benzene 15 eluate is evaporated, the residue left in the oil extract is crystallized from the ether. The product was obtained at 27.8 g (49.2% of the original product), and the temperature was melted at 99-101 ° ⁇ (ether).
  • ⁇ aydeya ⁇ % C 67.85; ⁇ 7.89; C ⁇ 12.96.
  • ⁇ aydeya ⁇ % C 67.85; ⁇ 7.89; C ⁇ 12.96.
  • the output of the product was $ 45.5, including for the dry house, the temperature for melting ⁇ 00- ⁇ 02 ° ⁇ . Found% ⁇ C 68.65; ⁇ 8.15; C ⁇ 11.98.
  • Example I the product is carried out in accordance with Example I.
  • the product is equipped with a silica gel, which is free of charge (1).
  • the output of the product was 14.5, based on the living room.
  • the product is packaged with a burnt gel, using benzene / etched solvent as an eluent (1: 1).
  • the output of the product was 35 30% as a result of the outgoing city. - 24 -
  • the product of the restoration of the unit is mounted on a ring with silica gel (benzene / ethyl acetate 4: 1),
  • the benzene product is mounted on a column with aluminum oxide and emits the target product in the form of oil, which is easily crystallized from the air. Melting point ⁇ 06- ⁇ 08 ° ⁇ . 15 The output of the product amounted to $ 54, calculated on the original connection.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Dérivés de stéroïdes de séries d'androstane constituant des composés de formule générale (I), où R1 = -OCOCH2C6H4N(CH2CH2Cl)2; -OH; -O-; R2 = -OCO(CH2)n C6H4N(CH2CH2X)2, where n = 1,3; X = Cl, Br, J; -OH; -O-; formule (II); R3 = -CH3; -H.
PCT/SU1984/000033 1984-06-27 1984-06-27 Derives de steroides de series d'androstane Ceased WO1986000311A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DE19843490728 DE3490728T1 (de) 1984-06-27 1984-06-27 Steroidderivate der Androstanreihe
DE19843490728 DE3490728C2 (de) 1984-06-27 1984-06-27 Androstan-Derivate
GB08602936A GB2169900B (en) 1984-06-27 1984-06-27 Derivatives of steroids of androstane series
PCT/SU1984/000033 WO1986000311A1 (fr) 1984-06-27 1984-06-27 Derives de steroides de series d'androstane
CH571/86A CH666276A5 (de) 1984-06-27 1984-06-27 Steroidderivate der androstanreihe.
JP60500685A JPS61502256A (ja) 1984-06-27 1984-06-27 アンドロスタン系ステロイド誘導体
SE8600828A SE457535B (sv) 1984-06-27 1986-02-24 Steroidderivat i androstanserien innehaallande aatminstone en klorfenacylestergrupp
FI860815A FI84834C (fi) 1984-06-27 1986-02-25 Foerfarande foer framstaellning av terapeutiskt anvaendbara steroidderivat av androstanserien.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/SU1984/000033 WO1986000311A1 (fr) 1984-06-27 1984-06-27 Derives de steroides de series d'androstane

Publications (1)

Publication Number Publication Date
WO1986000311A1 true WO1986000311A1 (fr) 1986-01-16

Family

ID=21616852

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SU1984/000033 Ceased WO1986000311A1 (fr) 1984-06-27 1984-06-27 Derives de steroides de series d'androstane

Country Status (7)

Country Link
JP (1) JPS61502256A (fr)
CH (1) CH666276A5 (fr)
DE (2) DE3490728T1 (fr)
FI (1) FI84834C (fr)
GB (1) GB2169900B (fr)
SE (1) SE457535B (fr)
WO (1) WO1986000311A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1001860A3 (ru) * 1978-08-14 1983-02-28 Куреха Кагаку Когио Кабусики Кайся (Фирма) Способ получени производных хлорамбуцила (его варианты)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1558472A (en) * 1976-01-22 1980-01-03 Leo Ab 17-esters of 17- hydroxy gestogens

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1001860A3 (ru) * 1978-08-14 1983-02-28 Куреха Кагаку Когио Кабусики Кайся (Фирма) Способ получени производных хлорамбуцила (его варианты)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Journal of Medicinal Chemistry, Vol. 15, No. 11, 1982, by the AMERICAN CHEMICAL SOCIETY, (Columbus, USA), F.I. CARROLL et al: "Antitumor and Antileukemic Effects of some steriods ad other biologically interesting compounds containing an alkylating agent", pages 1159 and 1160 *

Also Published As

Publication number Publication date
JPH0240079B2 (fr) 1990-09-10
SE8600828L (sv) 1986-02-24
GB2169900A (en) 1986-07-23
FI860815A0 (fi) 1986-02-25
CH666276A5 (de) 1988-07-15
GB8602936D0 (en) 1986-03-12
SE457535B (sv) 1989-01-09
JPS61502256A (ja) 1986-10-09
SE8600828D0 (sv) 1986-02-24
DE3490728T1 (de) 1986-06-05
FI84834C (fi) 1992-01-27
FI860815L (fi) 1986-02-25
FI84834B (fi) 1991-10-15
GB2169900B (en) 1988-02-17
DE3490728C2 (de) 1989-09-14

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