GB1264941A - - Google Patents
Info
- Publication number
- GB1264941A GB1264941A GB1264941DA GB1264941A GB 1264941 A GB1264941 A GB 1264941A GB 1264941D A GB1264941D A GB 1264941DA GB 1264941 A GB1264941 A GB 1264941A
- Authority
- GB
- United Kingdom
- Prior art keywords
- androstene
- prepared
- steroids
- diethylaminoethoxy
- androstan
- 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
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- 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
- 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
- C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Steroid Compounds (AREA)
Abstract
1,264,941. 2-Androstene 17-ethers. MERCK PATENT G.m.b.H. 19 March, 1970 [12 April, 1969], No. 13298/70. Heading C2U. Novel steroids of'the formula (wherein R<SP>1</SP> and R<SP>2</SP> are each C 1-3 alkyl, or -NR<SP>1</SP>R<SP>2</SP> is pyrrolidino, piperidino, hexamethyleneimino, 1-piperazinyl or morpholino, and n is 2, 3 or 4) and salts thereof are prepared (a) from corresponding 17#-X-steroids and amines Y-C n H 2n -NR<SP>1</SP>R<SP>2</SP>, where X and Y are OH or functional derivatives thereof, or one of them is a halogen; or (b) by N-alkylation of corresponding 17#-OC n H 2n NHR<SP>3</SP> steroids, where R<SP>3</SP> is H or C 1-3 alkyl; or (c) by condensation of corresponding 17#-OC n H 2n Z-steroids, where Z is as X or Y with an amine NHR<SP>1</SP>R<SP>2</SP>; or (d) by reacting corresponding 3#-Z-ring A-saturated steroids with a compound capable of splitting off HZ; or (e) by reducing corresponding steroids containing a carbonyl or thiocarbonyl group in the 17-side chain adjacent to the O or N atom, or by reducing corresponding steroids containing an episulphide group in the 2,3- position or a #<SP>2</SP>-3-thioenol ether grouping. 2-Androsten-17α-ol is prepared, together with the corresponding 17#-ol, from which it is separated chromatographically, by reduction of the corresponding 17-one, and is subsequently converted to its tosylate. 17α-Bromo-2-androstene is prepared by the action of KBr on the corresponding 17#-ol tosylate. 17#-(2-aminoethoxy)-2- androstene is prepared from the corresponding 17#-ol via 17#-(2-hydroxyethoxy)-2-androstene and 17# - (2 - chlorethoxy) - 2 - androstene 17(3- (3 - aminopropoxy) - 2 - androstene is prepared by cyanoethylation of the 17#-ol followed by reduction. 17# - (4 - aminobutoxy) - 2 - androstene is prepared by reacting the Na derivative of 2-androsten-17#-ol with 4-bromobutyric acid nitrite and then reducing. 17#-(2-ethylaminoethoxy)-2-androstene is prepared by reacting the 17#-ONa compound with bromoacetaldehyde diethyl acetal and hydrolysing to form 17#- formylmethoxy - 2 - androstene, reacting with ethylamine to form the Schiff's base, and reducing this. 17#-(2-chloroethoxy)-2-androstene is prepared from the 17#-ONa compound and 1 - bromo - 2 - chloro - ethane. 17#-pyrrolidinocarbonylmethoxy-2-androstene is prepared from the 17#-ol and chloroacetic acid pyrrolidide; 17# - diethylaminocarbonylmethory - 2 - androstene is prepared similarly. 17#-(2-N-acetyl-N- ethylaminoethoxy) - 2 - androstene is prepared by acetylation of 17#-(2-ethylaminoethoxy)-2-androstene. Morpholinoacetic acid - (2 - androsten- 17#-yl)-ester is prepared from morpholinoacetic acid and 2-androsten-17#-ol. 17#-(2-diethylaminoethoxy) - androstan - 3# - ol 3 - tosylate is prepared by reacting androstane-3#,17#-diol 3-tetrahydropyranyl ether with 2-diethylaminoethyl chloride to form 17#-(2-diethylaminoethoxy) - androstan - 3# - ol 3 - tetrahydropyranyl ether, hydrolysing this to the free 3#-ol and esterifying this. 3α-Chloro-17#-(2-diethylaminoethoxy)-androstane is prepared from the corresponding 3#-ol tosylate and KCl. 17#-(2-diethylaminoethoxy) - androstan - 3α - ol is obtained as a by-product in the preparation of 17#-(2- diethylamino ethoxy)-2-androstane from 17#- (2 - diethylaminoethoxy) - androstan - 3# - ol mesylate; similarly 17#-(2-diethylaminoethoxy)- androstan-3α and 3#-ols are obtained from the benzenesulphonate of the 3#-ol. The novel steroids are stated to possess antihypercholesterolaemic, estrogenic, anti-estrogenic, contraceptive, fungicidal and bacteriocidal properties and they may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691918699 DE1918699A1 (en) | 1969-04-12 | 1969-04-12 | 2-Androstene-17-ether and process for their preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1264941A true GB1264941A (en) | 1972-02-23 |
Family
ID=5731050
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1264941D Expired GB1264941A (en) | 1969-04-12 | 1970-03-19 |
Country Status (14)
Country | Link |
---|---|
JP (1) | JPS4843903B1 (en) |
AT (2) | AT302546B (en) |
BE (1) | BE748720A (en) |
BR (1) | BR6915479D0 (en) |
CH (1) | CH533607A (en) |
CS (1) | CS149424B2 (en) |
DE (1) | DE1918699A1 (en) |
DK (1) | DK129989B (en) |
ES (1) | ES378469A1 (en) |
FR (1) | FR2042324B1 (en) |
GB (1) | GB1264941A (en) |
IL (1) | IL34217A (en) |
NL (1) | NL7004608A (en) |
SE (1) | SE349299B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2020108070A (en) | 2018-12-28 | 2020-07-09 | 株式会社東芝 | Communication control device and communication control system |
-
1969
- 1969-04-12 DE DE19691918699 patent/DE1918699A1/en active Pending
- 1969-12-19 BR BR215479/69A patent/BR6915479D0/en unknown
-
1970
- 1970-03-19 GB GB1264941D patent/GB1264941A/en not_active Expired
- 1970-03-31 CS CS368A patent/CS149424B2/cs unknown
- 1970-03-31 IL IL34217A patent/IL34217A/en unknown
- 1970-04-01 NL NL7004608A patent/NL7004608A/xx unknown
- 1970-04-03 DK DK169170AA patent/DK129989B/en unknown
- 1970-04-06 CH CH503170A patent/CH533607A/en not_active IP Right Cessation
- 1970-04-08 SE SE04771/70A patent/SE349299B/xx unknown
- 1970-04-08 AT AT1107570A patent/AT302546B/en not_active IP Right Cessation
- 1970-04-08 AT AT321970A patent/AT296515B/en not_active IP Right Cessation
- 1970-04-09 BE BE748720D patent/BE748720A/en unknown
- 1970-04-10 FR FR707012963A patent/FR2042324B1/fr not_active Expired
- 1970-04-11 JP JP45030709A patent/JPS4843903B1/ja active Pending
- 1970-04-11 ES ES378469A patent/ES378469A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
NL7004608A (en) | 1970-10-14 |
JPS4843903B1 (en) | 1973-12-21 |
ES378469A1 (en) | 1972-06-16 |
DK129989C (en) | 1975-05-20 |
AT302546B (en) | 1972-10-25 |
CS149424B2 (en) | 1973-07-05 |
SE349299B (en) | 1972-09-25 |
DE1918699A1 (en) | 1970-10-15 |
IL34217A0 (en) | 1970-05-21 |
BR6915479D0 (en) | 1973-01-25 |
BE748720A (en) | 1970-10-09 |
FR2042324B1 (en) | 1973-08-10 |
AT296515B (en) | 1972-02-25 |
IL34217A (en) | 1973-03-30 |
DK129989B (en) | 1974-12-09 |
CH533607A (en) | 1973-02-15 |
FR2042324A1 (en) | 1971-02-12 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PLNP | Patent lapsed through nonpayment of renewal fees |