GB1025906A - New amino-steroid compounds and processes for their preparation - Google Patents
New amino-steroid compounds and processes for their preparationInfo
- 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
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.
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)
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 |
-
0
- NL NL297135D patent/NL297135A/xx unknown
- BE BE636641D patent/BE636641A/xx unknown
- NL NL297131D patent/NL297131A/xx unknown
- NL NL123751D patent/NL123751C/xx active
- NL NL297133D patent/NL297133A/xx unknown
-
1962
- 1962-08-27 FR FR907856A patent/FR1421231A/en not_active Expired
- 1962-11-27 FR FR916749A patent/FR2374M/en not_active Expired
-
1963
- 1963-05-03 FR FR933624A patent/FR56F/en not_active Expired
- 1963-08-22 ES ES290991A patent/ES290991A1/en not_active Expired
- 1963-08-27 DE DER35992A patent/DE1212082B/en active Pending
- 1963-08-27 GB GB3393663A patent/GB1025906A/en not_active Expired
- 1963-08-27 DE DER35990A patent/DE1212080B/en active Pending
- 1963-08-27 GB GB3393863A patent/GB1025908A/en not_active Expired
- 1963-08-27 DE DER35993A patent/DE1212083B/en active Pending
- 1963-08-27 DE DER35991A patent/DE1212081B/en active Pending
- 1963-08-27 GB GB3393763A patent/GB1025907A/en not_active Expired
-
1965
- 1965-04-14 GB GB1601065A patent/GB1045644A/en not_active Expired
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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