GB1045644A - New amino-steroid compounds and processes for their preparation - Google Patents

New amino-steroid compounds and processes for their preparation

Info

Publication number
GB1045644A
GB1045644A GB1601065A GB1601065A GB1045644A GB 1045644 A GB1045644 A GB 1045644A GB 1601065 A GB1601065 A GB 1601065A GB 1601065 A GB1601065 A GB 1601065A GB 1045644 A GB1045644 A GB 1045644A
Authority
GB
United Kingdom
Prior art keywords
methyl
pregnane
ethyl
acid
acid addition
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
GB1601065A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1045644A publication Critical patent/GB1045644A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • 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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—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 no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
    • 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
    • C07J41/005—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 only two carbon atoms, e.g. pregnane 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 20-amino-pregnanes having the general formula <FORM:1045644/C2/1> (wherein R3 is an hydrogen atom or an acyl radical Ac derived from a substituted or unsubstituted lower organic carboxylic acid having 1-12 carbon atoms, and R4 is the methyl or ethyl group) and acid addition salts thereof; a 20-imino-pregnane having the structural formula <FORM:1045644/C2/2> and the methyl and ethyl halide salts thereof, and processes for the preparation thereof wherein 3a -hydroxy-5b -pregnan-20-one is reacted with methylamine or ethylamine to yield the corresponding 20-N-methyl or ethylimino pregnane, reacting the latter with an ethyl or methyl halide to form a 3a -hydroxy-20-N-methyl or ethyl-20-N-ethylimino-pregnane and reacting the latter with methyl magnesium halide so as to form the corresponding 20-amino pregnane or acid addition salt thereof. The pregnane base may be converted into an acid addition salt by treatment with an acid, e.g. hydrochloric or oxalic acid. Pharmaceutical compositions, having vasodilative and spasmolytic action and containing compounds having the first of the above formul\s A, are administered orally as solutions, syrups, suspensions, granules and tablets, by injection as sterile aqueous and non-aqueous solutions, or via the body cavities in the form of a suppository.
GB1601065A 1962-08-27 1965-04-14 New amino-steroid compounds and processes for their preparation Expired GB1045644A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR907856A FR1421231A (en) 1962-08-27 1962-08-27 New amino steroids and method of preparation

Publications (1)

Publication Number Publication Date
GB1045644A true GB1045644A (en) 1966-10-12

Family

ID=8785774

Family Applications (4)

Application Number Title Priority Date Filing Date
GB3393763A Expired GB1025907A (en) 1962-08-27 1963-08-27 New amino-steroid compounds and processes for their preparation
GB3393663A Expired GB1025906A (en) 1962-08-27 1963-08-27 New amino-steroid compounds and processes for their preparation
GB3393863A Expired GB1025908A (en) 1962-08-27 1963-08-27 New amino-steroid compounds and processes for their preparation
GB1601065A Expired GB1045644A (en) 1962-08-27 1965-04-14 New amino-steroid compounds and processes for their preparation

Family Applications Before (3)

Application Number Title Priority Date Filing Date
GB3393763A Expired GB1025907A (en) 1962-08-27 1963-08-27 New amino-steroid compounds and processes for their preparation
GB3393663A Expired GB1025906A (en) 1962-08-27 1963-08-27 New amino-steroid compounds and processes for their preparation
GB3393863A Expired GB1025908A (en) 1962-08-27 1963-08-27 New amino-steroid compounds and processes for their preparation

Country Status (6)

Country Link
BE (1) BE636641A (en)
DE (4) DE1212080B (en)
ES (1) ES290991A1 (en)
FR (3) FR1421231A (en)
GB (4) GB1025907A (en)
NL (4) NL123751C (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3013008A (en) * 1961-01-09 1961-12-12 Searle & Co N-substituted 20-aminopregnan-3-ols, esters thereof, and deta-derivatives corresponding

Also Published As

Publication number Publication date
DE1212081B (en) 1966-03-10
BE636641A (en)
GB1025906A (en) 1966-04-14
NL123751C (en)
FR56F (en) 1964-10-16
NL297135A (en)
GB1025908A (en) 1966-04-14
ES290991A1 (en) 1963-12-01
GB1025907A (en) 1966-04-14
DE1212082B (en) 1966-03-10
DE1212083B (en) 1966-03-10
NL297133A (en)
FR2374M (en) 1964-04-03
FR1421231A (en) 1965-12-17
NL297131A (en)
DE1212080B (en) 1966-03-10

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