GB1025906A - New amino-steroid compounds and processes for their preparation - Google Patents

New amino-steroid compounds and processes for their preparation

Info

Publication number
GB1025906A
GB1025906A GB3393663A GB3393663A GB1025906A GB 1025906 A GB1025906 A GB 1025906A GB 3393663 A GB3393663 A GB 3393663A GB 3393663 A GB3393663 A GB 3393663A GB 1025906 A GB1025906 A GB 1025906A
Authority
GB
United Kingdom
Prior art keywords
acid addition
amino
pregnane
addition salt
acid
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
GB3393663A
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 GB1025906A publication Critical patent/GB1025906A/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:1025906/C2/1> wherein X is the oxygen atom of a keto group or is a group a -H(OR3), R3 being a hydrogen atom or an acyl radical Ac derived from a substituted or unsubstituted lower organic carboxylic acid having from 2-18 carbon atoms; R and R1 are the same or different, and each is alkyl, aryl or aralkyl group or together they form a heterocyclic ring system and R3 is a lower alkyl group having from 1-4 carbon atoms), and acid addition salts thereof and processes for the preparation thereof wherein an 11b -hydroxy-20-amino-pregnane of the partial general formula <FORM:1025906/C2/2> (wherein only the C and D rings of the pregnane nucleus are shown and R, R1 and R2 are as defined above) or an acid addition salt thereof, is reacted with a strong oxidizing agent so as to form the corresponding 11-keto-20-amino-pregnane or acid addition salt thereof. As oxidizing agent there may be used sulphochromic mixture. The preferred starting compound is 3a -acyloxy-11b -hydroxy-20-amino-5b -pregnane or an acid addition salt thereof and the product obtained therefrom may be saponified to obtain the corresponding 3a -hydroxy compound. Dehydrogenation of the products to form 3,11-diketo-20-amino-pregn-4-enes may be effected by sequential bromination and dehydrobromination. The pregnane base may be converted to an acid addition salt by treatment with an acid, e.g. hydrochloric or oxalic acid. Pharmaceutical compositions having vasodilative spasmolytic action and containing compounds of the first of the above formul\SA or acid addition salts thereof, are administered orally as tablets, powders, solutions or suspension, by injection in sterile aqueous and non-aqueous solutions, via the body cavities in the forms of suppositories or pessaries, or externally as a powder, lotion, cream or ointment.
GB3393663A 1962-08-27 1963-08-27 New amino-steroid compounds and processes for their preparation Expired GB1025906A (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
GB1025906A true GB1025906A (en) 1966-04-14

Family

ID=8785774

Family Applications (4)

Application Number Title Priority Date Filing Date
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
GB3393763A Expired GB1025907A (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 After (3)

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

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
ES290991A1 (en) 1963-12-01
NL297133A (en)
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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