GB1366175A - Antilarval azasteroids - Google Patents

Antilarval azasteroids

Info

Publication number
GB1366175A
GB1366175A GB3778873A GB3778873A GB1366175A GB 1366175 A GB1366175 A GB 1366175A GB 3778873 A GB3778873 A GB 3778873A GB 3778873 A GB3778873 A GB 3778873A GB 1366175 A GB1366175 A GB 1366175A
Authority
GB
United Kingdom
Prior art keywords
cycloalkyl
alkyl
acid
cyclopentanone
steroid
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.)
Expired
Application number
GB3778873A
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.)
GD Searle LLC
Original Assignee
GD Searle LLC
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 GD Searle LLC filed Critical GD Searle LLC
Publication of GB1366175A publication Critical patent/GB1366175A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
    • 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
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • 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
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • 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
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Steroid Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1366175 Steroids containing nitrogen in the 17-side chain G D SEARLE & CO 14 March 1972 [15 March 1971] 37788/73 Divided out of 1366174 Headings C2U and C2C Novel steroids of the formula and acid-addition salts thereof; wherein #<SP>5</SP> is optional and when it is absent the H atom in the 5-position can have alpha or beta configuration; the 3-substituent is in the α- or #-configuration; R 1 and R 2 are each C 1-8 alkyl; R 3 is H or C 1-8 alkyl; Alk is C 2-8 alkylene separating A and N by at least 2 C atoms; A is -CH- or -N-; and R 4 is C 3-7 cycloalkyl, C 4-19 cycloalkyl-alkyl or C 5-18 cycloalkyl-alkanoyl but can only be cycloalkyl-alkanoyl when A is -N-; are prepared (i) by direct formation of the 3-ethers or 3-acylates from the corresponding 3-ols, or by indirect formation, e.g. reaction of the 3-ol with a dimethyl- or diethyl-ketal of an appropriate ketone, e.g. cyclopentanone followed by hydrogenation of the cycloalkenyloxy or cycloalkylalkenyloxy ether thus-produced; or conversion of the 3-ol to a 3-(alkyl or aryl) sulphonyloxy steroid and then reaction of this with the appropriate alcohol R 4 OH; or (ii) by effecting the etherification and acylation processes of (i) on a 3-hydroxyandrostan-17-one or corresponding #<SP>5</SP>-steroid and then inserting the required 17-side chain, e.g. by condensing with an appropriate diamine to give a steroid of the formula and then reducing this to give a product wherein AR 3 is NH, which may then be alkylated, for example by reductive methylation or by N- acylation followed by reduction of the amide; or (iii) to obtain products wherein A is -CH-, by subjecting steroids containing a 17-side chain of the formula to hydrazide then azide formation, subjecting the azides to the Curtius rearrangement and hydrolysing the isocyanates thus-produced to the corresponding primary amines which are then dialkylated; or by reacting similar acid chlorides (from the acids and SOCl 2 ) with amines R 1 R 2 NH and then reducing the amides thus-produced. #<SP>5</SP>-Products may be hydrogenated to the corresponding 5α-androstanes. 3#-Methoxychol-5-en-24-ic acid methyl ester is prepared by esterifying 3#-hydroxychol-5-en- 24-ic acid to give the methyl ester and then converting this to the 3-methyl ether via the 3- tosylate. The diethyl ketal of cyclopentanone is prepared from cyclopentanone and triethylorthoformate. The novel steroids are used to inhibit the growth of larvae and nymphs of certain insects (see Specification 1,366,174).
GB3778873A 1971-03-15 1972-03-14 Antilarval azasteroids Expired GB1366175A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12449971A 1971-03-15 1971-03-15

Publications (1)

Publication Number Publication Date
GB1366175A true GB1366175A (en) 1974-09-11

Family

ID=22415232

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1183572A Expired GB1366174A (en) 1971-03-15 1972-03-14 Method of inhibiting the growth of larvae and nymphs with azasteroids
GB3778873A Expired GB1366175A (en) 1971-03-15 1972-03-14 Antilarval azasteroids

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1183572A Expired GB1366174A (en) 1971-03-15 1972-03-14 Method of inhibiting the growth of larvae and nymphs with azasteroids

Country Status (4)

Country Link
JP (1) JPS55102503A (en)
CA (1) CA978087A (en)
DE (1) DE2212197A1 (en)
GB (2) GB1366174A (en)

Also Published As

Publication number Publication date
GB1366174A (en) 1974-09-11
CA978087A (en) 1975-11-18
JPS55102503A (en) 1980-08-05
DE2212197A1 (en) 1972-09-21

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee