ES290991A1 - Procedure for the preparation of amino steroids (Machine-translation by Google Translate, not legally binding) - Google Patents

Procedure for the preparation of amino steroids (Machine-translation by Google Translate, not legally binding)

Info

Publication number
ES290991A1
ES290991A1 ES290991A ES290991A ES290991A1 ES 290991 A1 ES290991 A1 ES 290991A1 ES 290991 A ES290991 A ES 290991A ES 290991 A ES290991 A ES 290991A ES 290991 A1 ES290991 A1 ES 290991A1
Authority
ES
Spain
Prior art keywords
formula
alkyl
functions
double bond
salt
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
ES290991A
Other languages
Spanish (es)
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 ES290991A1 publication Critical patent/ES290991A1/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

Preparation process, of the amino-steroids of the general formula; ** (See formula) ** wherein R and R1 represent lower alkyl, aryl or aralkyl radicals, R2 represents tm alkyl radical having from 1 to 4 carbon atoms, (see formula), being OR3 of alpha or beta configuration and designating R3 hydrogen or a substituted lower acyl radical or not, Y = H2 0 (see formula) the hydroxyl being in alpha or in beta, these compounds can be saturated and belong to the series 5alfa, or 5beta-pregnanes or can even be unsaturated and have a double bond that starts from carbon 4, or a system of two double bonds in positions 1 and 4, as well as the salts of these compounds, characterized in that a primary omin of formula NH2R is reacted on a 20-oxo asteroid of the pragnano series, in which the other functions are previously protected Existing ketone in the form of a cyclic ketal, the resulting 20-imino derivative is transformed into the ternary imino salt by treatment with a lower alkyl, aryl or aralkyl halide of the formula hal.R1 (a halogen being halo), the salt obtained is reacted with an alkyl magnesium halide of the formula Hal.HgR2, a 20-alkyl-20-amino steroid is obtained from which the ketone functions are released by hydrolysis, and/or the functions are transformed sn 3 and/or 11 by reduction or oxidation, an existing double bond in position 5,5 is possibly reduced and/or a double bond in position 4,5 is introduced, or a system of two double bonds in position 1,2 and 4,5, and/or arrived at the case the hydroxyl function is acylated at 3 or the resulting compound is eventually converted to a salt of a mineral or organic acid. (Machine-translation by Google Translate, not legally binding)
ES290991A 1962-08-27 1963-08-22 Procedure for the preparation of amino steroids (Machine-translation by Google Translate, not legally binding) Expired ES290991A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR907856A FR1421231A (en) 1962-08-27 1962-08-27 New amino steroids and method of preparation
FR933624A FR56F (en) 1962-08-27 1963-05-03 New drug in particular for the treatment of spasms of coronary or vascular origin.

Publications (1)

Publication Number Publication Date
ES290991A1 true ES290991A1 (en) 1963-12-01

Family

ID=8785774

Family Applications (1)

Application Number Title Priority Date Filing Date
ES290991A Expired ES290991A1 (en) 1962-08-27 1963-08-22 Procedure for the preparation of amino steroids (Machine-translation by Google Translate, not legally binding)

Country Status (6)

Country Link
BE (1) BE636641A (en)
DE (4) DE1212082B (en)
ES (1) ES290991A1 (en)
FR (3) FR1421231A (en)
GB (4) GB1025906A (en)
NL (4) NL297133A (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
NL297133A (en)
GB1025906A (en) 1966-04-14
BE636641A (en)
DE1212081B (en) 1966-03-10
FR2374M (en) 1964-04-03
NL297131A (en)
FR1421231A (en) 1965-12-17
GB1025907A (en) 1966-04-14
NL123751C (en)
DE1212083B (en) 1966-03-10
DE1212082B (en) 1966-03-10
FR56F (en) 1964-10-16
GB1025908A (en) 1966-04-14
GB1045644A (en) 1966-10-12
NL297135A (en)
DE1212080B (en) 1966-03-10

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